The harder part?

Convincing a lender that you're the person who should own it.

That's where most acquisitions quietly fall apart.

In this episode, Jaryd is joined by Jared W. Johnson, the top individual SBA loan producer in the United States, who's helped fund more than $800 million worth of business acquisitions. But this isn't just another conversation about lending. Jared has been on both sides of the table.

He recently acquired a $600,000 eCommerce business himself.

What caught his attention wasn't perfect systems or polished financials. It was the opposite. A business with outdated processes, inventory tracked entirely from memory, and obvious operational gaps that most buyers would see as red flags.

He saw upside.

Together, Jaryd and Jared unpack how the deal came together, why the business was relocated across states, how a 3PL simplified operations, and why keeping one long-term employee became one of the smartest decisions they made after the acquisition.

They also pull back the curtain on how lenders really think.

Why do buyers with strong incomes still get declined? What makes someone trustworthy in the eyes of a bank? Does your personal spending matter? And when a business has valuable assets like an email list, loyal customers, strong SEO, or a large social following, how much weight do lenders actually give them?

Whether you're preparing to buy your first business or looking to finance your next acquisition, this episode gives you a clearer picture of what separates buyers who get approved from those who don't.

The best deals don't always go to the highest bidder.

They usually go to the buyer who's prepared.

🎧 Hit play and discover what lenders are really looking for before they ever approve a business acquisition loan.

Episode Highlights

04:14 - Inside Jared's $600K eCommerce Acquisition: Why He Bought a Business Most Buyers Would Walk Away From

12:36 - From California to Texas: How They Relocated the Business, Switched to a 3PL, and Kept Operations Running Smoothly

21:42 - The Top Reasons SBA Loans Get Declined - Even When the Business Looks Like a Great Deal

24:26 - How to Make Lenders Believe You're Ready to Buy Your First Business (Even Without Owning One Before)

27:45 - The "Leaky Bucket" Test: Why Your Personal Finances Can Make or Break an SBA Approval

31:09 - How Banks Really Value Email Lists, SEO, Social Media, and Other Intangible Business Assets

36:18 - The Simple Move That Can Turn a "Maybe" Into a Loan Approval When You're Short on Experience

Key Takeaways

➥ The best acquisitions often hide behind messy operations. What looks inefficient to most buyers can become an opportunity with the right systems and execution.

➥ Lenders don't just evaluate the business - they evaluate the buyer. Your experience, preparation, and financial discipline all influence loan approval.

➥ First-time buyers can still secure SBA financing by demonstrating industry knowledge, a clear plan, and the ability to operate the business successfully.

➥ Retaining experienced employees can be one of the smartest post-acquisition decisions. Institutional knowledge is often more valuable than documented processes.

➥ Your personal finances matter. Lenders view your spending habits, savings, and cash reserves as indicators of how you'll manage a business.

➥ Email lists, SEO, customer databases, and social media add value - but lenders focus on how they support consistent cash flow, not just their size.

➥ Buying the business is only the beginning. Long-term success comes from continuously improving operations, learning the business, and investing in the right people.

About Jared Johnson

Jared W. Johnson is the biggest individual SBA producers in the United States, having closed over $800 million in SBA loans across his 15+ year career, the majority being M&A and business acquisition deals. As VP and Senior Business Development Officer at First Internet Bank, he's a two-time Coleman Publishing SBA BDO of the Year. He's also a business owner himself, having personally acquired and exited a manufacturing company. He hosts the Before You Buy or Sell a Business podcast.

Connect with Jared Johnson

➥ https://www.linkedin.com/in/jaredwjohnson/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Can this survive AI?

Wrong lens. Wrong era. Wrong way to size up a deal.

Tony Xu ran product and engineering at Flippa for five years before taking over as CEO. He's sat behind the scenes of thousands of transactions, tracked which categories exploded and which quietly faded, and seen firsthand what happens once AI actually touches a working business. And he'll say something most of the doom content circulating right now won't.

AI isn't hunting your business down. It's clearing out the grunt work inside it.

Photo editing. Listing copy. Animation that used to demand a full production team. Rough drafts of ad creative. Tasks that used to consume a founder's entire week now take minutes. Treating that as a threat misses what it really is.

A head start.

But here's the part almost nobody admits out loud.

Nothing essential has changed. Who you reach. What people remember about your brand. Whether your customers stick around. Claude can write your listing copy. It can't earn you a decade-long relationship that gets your product onto a shelf. It's not handling your cash flow. It's not securing your credit line. It's not the reason someone buys from you twice. The businesses pulling ahead right now aren't the ones hiding from AI. They're run by people who know precisely where its usefulness ends and the real value begins.

In this episode, Jaryd talks with Tony about what's really moving inside Flippa's marketplace. Why $250K to $5M has become the sweet spot for the sharpest buyers. How specialist operators are walking into neglected businesses and multiplying category growth in a matter of months. The difference between a roll-up play and a specialist play. And why chasing "AI-proof" is precisely the wrong instinct to bring into diligence.

They also break down the two warning signs that should end a deal immediately. How a buyer's own comfort with AI can cut a year-long ramp-up down to half that. And why the businesses that seem the most behind the curve might actually be the cheapest assets on the whole platform.

The buyers nervous about AI aren't wrong to be paying attention.

They're just tracking the wrong risk.

Tony isn't.

🎧 Hit play. Straight from the person who built the platform. No hype, no scare tactics, just where the real opportunity is sitting.

Episode Highlights

02:55 - Inheriting the Throne: Taking Over as Flippa CEO After Eight Years of Blake's Leadership

04:05 - The Globalization of Flippa: Why 60% of European Businesses Are Now Being Bought by Americans

05:26 - Multi-Currency, AI Translation, and 158 Payment Options: The Infrastructure Behind Flippa's Cross-Border Boom

06:59 - From Sub-$10K Domains to $250K-$5M Deals: How the Sweet Spot of Flippa Acquisitions Has Shifted Over a Decade

08:49 - Why E-Commerce Remains the Gold Standard for First-Time Buyers and How to Pick the Right Vertical

11:30 - The 450,000-Buyer Marketplace: How AI Recommendations and Watchlists Make an Overwhelming Number of Listings Feel Personal

14:55 - From the Serbian DJ's 140-Business Roll-Up to Specialist Buyers Who Bring Their Own Distribution Network

22:10 - Tony's Contrarian Take on AI: Why It's Not a Strategy, Just an Operational Tool Everyone Will Eventually Use

26:40 - The K-Shaped Productivity Curve: Why AI Makes the Best Operators Two to Three Times More Effective

29:40 - What AI Still Can't Touch: Why Distribution, Brand, and Customer Trust Remain the Real Choke Points of Value

36:43 - Tony's First-Time Buyer Checklist: Distribution, Brand Personality, and Operational Soundness Before You Sign Anything

38:25 - The Two Dealbreakers: Regulatory Red Flags and Why You Need a Real Handover Plan With the Founder

40:49 - Flippa's New AI-Powered P&L Builder and Data Room: What's Coming Next for Sellers and Buyers

Key Takeaways

➥ AI isn't a strategy. It's just the next operational tool everyone adopts within months, the same way FBA and 3PLs did. Whatever edge it gives you today gets competed away fast.

➥ The best operators are now two to three times more productive than they were a year ago. AI doesn't replace the founder, it supercharges them. That turns a twelve-month turnaround into six.

➥ Nobody's handing Claude their ad budget and walking away. Distribution, customer trust, cash on the balance sheet, the real choke points of value are still completely untouched by AI. That gap is where the money is.

➥ Specialists beat generalists every time. Flippa's fastest-growing categories are led by people with niche expertise, not just capital. Find the vertical your skills can supercharge.

➥ You don't have to love the product to love the deal. Plenty of buyers acquire businesses they have zero personal interest in because they're hooked on the operations, the numbers, and the upside.

➥ Two things kill a deal fast: regulatory landmines and no handover plan. No license compliance or no founder transition period are both deal-breakers worth walking away from.

➥ AI is a tailwind for content, a wash for e-commerce, and a coin flip for SaaS. It all comes down to execution speed. Ship faster, cut churn, win. Sit still, and AI just made your competitor's job easier too.

About Tony Xu

Tony Xu is the CEO of Flippa - the world's #1 marketplace for buying and selling online businesses. With a background spanning economics, accounting, and a CPA qualification, Tony spent years as Flippa's Head of Product and Engineering, architecting the platform tools that have powered hundreds of thousands of digital business transactions. He's led the development of game-changing innovations including LaurenAI (Flippa's AI-powered deal sourcing engine), the Buyer Directory, and Flippa's AI-driven valuation tools - making institutional-grade M&A accessible to everyday entrepreneurs.

Connect with Tony Xu

➥ Flippa.com (affiliate link, not for Eden)

➥ https://www.linkedin.com/in/tony-x-62037498/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

How do I get my traffic back?

Wrong question. Wrong game. Wrong decade.

Steve Wiideman has thirty years in this industry. He's seen every update, every panic, every agency pivot. And he'll tell you something most people charging you monthly retainers will never admit.

The traffic isn't coming back.

AI overviews are eating clicks before you even show up. Agentic commerce means people are buying inside ChatGPT and YouTube without ever touching your website. Zero-click isn't coming. It's here. It's done. It's the new normal.

And most agencies are still selling you 2019 with a new logo.

But here's the thing nobody's saying out loud.

The fundamentals never broke. The shortcuts did.

Content farms. AI-generated blog factories. Link blasters. Agencies who promised more content meant more traffic. Google's March update didn't come out of nowhere. It was a warning that had been building for years. And it landed hard.

In this episode, Jaryd sits down with Steve to talk about what's actually happening. Why the businesses winning right now stopped chasing rankings entirely. How one sentence in a Google Maps review took a brand new burger joint to number one in two days. What agentic commerce means for your revenue model. And why single-source dependency on Google is the single biggest risk any online business is carrying right now.

They also get into why twenty real brand fans beat an entire link-building team. How to build content in a shrinking-click world. And the mindset shift separating businesses that are growing from the ones watching their dashboards collapse.

The agencies lying to you about AI aren't villains.

They just don't know what else to sell you.

Steve does.

🎧 Hit play. Thirty years of SEO truth. No fluff. No spin. Just the conversation your agency should have been having with you a long time ago.

Episode Highlights

03:01 - Why Google's Latest Updates Actually Confirm That Nothing Fundamental Has Changed About Great SEO

05:53 - The Zero-Click Reality: Why Your Lost Traffic Isn't Coming Back and What to Do Instead

07:49 - EEAT, AI Content, and the March Update: What Google Is Really Saying to Content Site Owners Right Now

08:53 - The Multimodal Content Approach: How Smart Brands Are Scaling Blogs Beyond Just Written Articles

13:21 - Why Blasting Your Brand Across Every Platform Is a Trap and the Two to Three Platform Rule That Actually Works

17:50 - The Hard Truth About Traffic: Why Chasing Old Click Numbers Is the Wrong Game Entirely

24:26 - Agentic Commerce and the Future of Google: How People Will Buy Without Ever Visiting Your Website Again

Key Takeaways

➥ The traffic isn't coming back. Full stop. The businesses winning right now accepted that early and stopped wasting energy trying to recapture something that no longer exists. They moved on. You should too.

➥ SEO was never about gaming Google. It was always about people. If ten results show up in a search, the brand that earns the click, delivers something real, and gets remembered wins. That hasn't changed. It never will.

➥ Seventy percent or more of your traffic from one source isn't a business. It's a bet. And right now that bet is paying out less than it ever has. Single-source dependency on Google is the biggest hidden risk sitting inside most content businesses today.

➥ One authentic sentence in a Google Maps review took a brand new restaurant to number one in two days. That's not luck. That's semantic triples working exactly as intended. What other platforms say about you in real conversations on real pages matters more than most people realize - to Google and to every LLM pulling citations.

➥ Publishing great content and moving on is the old game. The new game is lighting a fire around every piece you create. Get it in front of real people fast. The speed of early engagement signals more than most SEOs will ever tell you.

➥ People are already buying inside ChatGPT and YouTube without ever visiting a website. Agentic commerce isn't coming. It's here. And if your business isn't set up to sell where your customers already are, you're invisible at the moment that matters most.

➥ Traffic was never the point. Revenue was. Clicks don't pay bills. Customers do. The fastest mindset shift any online business owner can make right now is stopping the obsession with the dashboard and starting to measure what actually matters - people buying, returning, and telling others.

About Steve Wiideman

Steve Wiideman - known as "SEO Steve" - is the founder of Wiideman Consulting Group and co-author of SEO: Strategy & Skills, a college textbook used at universities across the US. With nearly 30 years in search, he's helped brands like Disney, Skechers, Public Storage, and Honda dominate organic traffic. A practitioner, scientist, and adjunct professor at UCSD and CSUF, Steve specialises in multi-location and e-commerce SEO and is one of the most trusted voices on navigating SEO in the era of AI search.

Connect with Steve Wiideman

➥ https://www.wiideman.com/

➥ https://www.stevewiideman.com/

➥ https://www.linkedin.com/in/seoexpert/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

The obvious growth.

The obvious profit.

The obvious opportunity.

That's exactly why they miss the best deals.

Kyle Brown spent years in investment banking and private equity evaluating acquisitions before ever buying a business himself.

And what he learned was simple: The businesses that look the safest aren't always the best investments. And the businesses that look broken aren't always broken.

When Kyle came across an ecommerce business that was barely breaking even, most buyers would have walked away.

Declining performance.

Frustrated owners.

Uncertain future.

On paper, it looked risky.

But Kyle wasn't looking at the same things everyone else was.

In this episode, Jaryd sits down with Kyle to unpack how investment bankers evaluate opportunities, how private equity investors think about risk, and how to value a business when traditional formulas stop working.

They discuss why so many buyers become obsessed with multiples, how distressed businesses can create outsized returns, and the operational changes that helped turn a struggling acquisition back into a profitable company.

But perhaps the biggest lesson is this: Buying a business isn't about finding perfection. It's about seeing something everyone else has missed.

Most buyers never learn how to do that. Kyle did.

🎧 Hit play to discover what investment bankers know about buying businesses that regular buyers will never figure out exists.

Episode Highlights

03:36 - How a Kid From an 800-Person Farming-Town High School Broke Into Investment Banking and Private Equity

07:03 - The $1M-$3M EBITDA Businesses His Family Office Targeted — And Why HVAC Became Their Favorite Acquisition Category

08:29 - The 25-Year-Old Who Took Over a Newly Acquired Ecommerce Business Just 30 Days After the Seller Walked Away

12:12 - How an 8-Year-Old Relationship Led to an Off-Market Acquisition Opportunity Nobody Else Saw

16:09 - The Break-Even Business Dilemma: How He Valued a 7-Figure Revenue Company When EBITDA Was Essentially Zero

20:14 - Why a Business That Once Generated $500K+ in Earnings Could Suddenly Be Worth Just 1x SDE

26:00 - The Turnaround Strategy: How Adding Customer Service, Sales Processes, and Accountability Took the Business Back to Profitability

30:14 - Why He Refuses to Build a Fund, Raise Millions, or Chase a Big Exit Despite Having the Background to Do It

Key Takeaways

➥ The best acquisition opportunities rarely look perfect. Kyle bought a business that was essentially breaking even because he focused on what it could become, not just what it looked like on closing day.

➥ Investment bankers don't just analyze numbers - they analyze risk. Revenue, profit, and multiples matter, but understanding why a business is struggling is often far more valuable than the financial statements themselves.

➥ A declining business gets discounted twice. First through lower earnings, and then through a lower valuation multiple. That's why turnarounds can create outsized returns for buyers who know how to fix the underlying problems.

➥ Relationships create opportunities that search never will. Kyle wasn't actively looking to buy a business when the deal appeared. An eight-year relationship and a consulting conversation led to an off-market acquisition most buyers would never have seen.

➥ You cannot improve a business you don't understand. Before hiring people or changing processes, Kyle answered customer calls himself, learned the products, and got into the weeds of the operation. The best operators understand the front lines before they build systems.

➥ Most struggling businesses don't need a miracle. They need execution. Answering the phone, following up with customers, building a sales process, improving accountability, and fixing neglected marketing channels can have a bigger impact than any growth hack.

➥ Buying a business can feel like buying yourself a job at first. The goal isn't to avoid work on day one. The goal is to build systems, people, and processes that eventually give you the freedom to work on the business instead of being trapped inside it.

➥ Not every acquisition needs to lead to a fund, a roll-up, or a massive exit. Sometimes the smartest strategy is to buy a good business, improve it, enjoy the cash flow, and let future opportunities emerge naturally rather than forcing the next deal.

About Kyle Brown

Kyle Brown is a Michigan State graduate who spent 5+ years in investment banking and private equity in Chicago before making the leap to operator. He ran an eCommerce HVAC distribution portfolio company from 2017–2020, discovered his passion for the business, and went on to acquire and exit industrial and eCommerce distribution businesses. Today he's the CEO of 1877ForParts.com — a niche HVAC parts eCommerce distributor with over 1 million parts in stock, applying institutional deal discipline to real-world small business ownership.

Connect with Kyle Brown

➥ 1877ForParts: https://www.1877forparts.com/ 

➥ LinkedIn: https://www.linkedin.com/in/msukylebrown/ 

➥ X: https://x.com/MSUKyleBrown 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

It's not.

It's signing an LOI you don't fully understand. Moving fast because someone on the internet told you speed wins. Then finding yourself thirty, forty thousand dollars deep into a deal that was never going to close the way you structured it.

Eric Hsu has seen it happen more times than he can count. Over 160 closed deals as an M&A attorney who exclusively represents buyers. And the pattern almost always starts at the LOI - that document most first-time buyers treat like a formality.

AI can hand you twenty questions to ask a seller. It can flag risk, validate numbers, model theory. It's genuinely useful. And genuinely dangerous when you don't know what you're actually looking at.

Because AI can't read why a seller gets vague about their Google Ads account in a way that means something. It can't tell you that annual subscription revenue the seller just collected isn't really theirs yet - and your client inherits every obligation to fulfil it. It doesn't understand deal psychology. It can't sit across from someone who built their business over thirty years and feel where the resistance is coming from.

That's pattern recognition. That's what 160 closed deals actually buys you.

In this episode, Jaryd and Eric pull apart exactly where AI helps, where it quietly misleads you, and where it has no business making the call.

You'll learn:

• Why the LOI is the single most expensive legal mistake first-time buyers make - and what stress-testing one actually looks like before you sign
• The working capital trap that kills deals mid-diligence and leaves buyers choosing between injecting $100K cash or walking away with nothing
• How SBA lending rules have shifted since mid-2025 - and why brokers now favour cash buyers who show up lender-ready from day one
• What AI genuinely cannot replicate: pattern recognition, human behaviour, and the deal empathy that holds negotiations together
• The holdco structure Eric recommends for portfolio buyers - when to set it up, why before your first SBA close, and what it actually costs
• Why integrity issues during diligence are non-negotiable walk-aways - and the dating analogy that explains exactly why

The glue of the deal is the relationship. The trust. The ability to get both sides on a call and actually work something out. AI can model the numbers. It can't do that.

🎧 Hit play - the most expensive legal mistake in your deal is the one you didn't know you were making.

Episode Highlights

03:32 - The Single Biggest Legal Mistake First-Time Buyers Make That Costs Them the Most Money

07:20 - The Working Capital Trap: How Buyers End Up $100K Apart From Sellers Halfway Through a Deal

13:43 - Why the Cheapest Time to Ask Questions Is Before the LOI - And How Most Buyers Get This Completely Backwards

19:50 - What AI Cannot Replicate in an M&A Deal: Pattern Recognition, Human Behaviour and Deal Empathy

23:30 - HoldCo Structures Explained: How to Set Up Your Portfolio the Right Way Before Your First SBA Close

35:39 - The Google Ads Red Flag: How a Seller Called Declining Traffic "Stable" and What It Really Meant

41:29 - Deal Psychology: Why the Glue of Every Deal Is the Relationship, Not the Data

Key Takeaways

➥ The LOI is not a formality - it's the foundation. Everything that goes wrong mid-deal or at closing can almost always be traced back to something that wasn't properly thought through before that document was signed.

➥ Speed without preparation isn't a competitive advantage. It's how you become the buyer who gets the door slammed in their face after wasting thirty thousand dollars in sunk costs.

➥ Working capital is not a detail to sort out later. If you don't align on it at LOI, you'll be renegotiating it under pressure - and that's when deals die or buyers get burned.

➥ AI is a tool, not a practitioner. It can hand you a checklist. It cannot tell you how this deal is going to play out, why the seller is hesitating, or what that vague answer about the Google Ads account actually means.

➥ Seller integrity during diligence is the single clearest signal you'll get. If they're not being straight with you when they want the money, they won't be straighter after they have it.

➥ Set up your HoldCo before your first SBA close if you plan to buy more than one business. Restructuring ownership after the fact means going back to the bank for permission. Getting it right once upfront costs less than fixing it later.

➥ The relationship is the deal. You cannot negotiate working capital, resolve diligence issues, or survive a hard conversation with data alone. Trust is built human to human - and no amount of AI can replace what happens when both sides get on a phone call and actually work it out together.

About Eric Hsu

Eric Hsu is a business acquisition attorney and the founder of Clear Focus Law and SMB Law Group, specializing in M&A for small and medium-sized businesses. Recognized as a Rising Star in Mergers & Acquisitions by Super Lawyers, Eric works exclusively on the buyer's side, helping self-funded entrepreneurs negotiate, structure, and close deals - including SBA-financed acquisitions. With clients across the US, he's known for transparent pricing, deep SBA expertise, and helping corporate professionals achieve freedom through acquisition.

Connect with Eric Hsu

➥ https://www.linkedin.com/in/lawyer4smbs/  

➥ https://lawyer4smbs.com/  

➥ https://buyersblackbook.com/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Not a little money. A lot. The kind of difference that turns a three-times multiple into a thirty-seven-times multiple. The kind of gap that separates someone who buys themselves a job from someone who builds a portfolio that works without them.

Brad Sugars has been on the right side of that gap for thirty years.

Founder of ActionCoach - the world's number one business coaching franchise across 80 countries. Over a million business owners coached. Sixteen books written. And a personal acquisition track record built on one thing most buyers never develop: a framework.

He once paid double what every other bidder offered. And still got the business for ten percent of what he knew it was actually worth. Because he could see value nobody else was looking at.

That's not luck. That's a system.

• In this episode, Jaryd sits down with Brad to unpack the acquisition philosophy that the top one percent use - and almost nobody at entry level even knows exists. You'll learn:
• The difference between a job buyer, financial buyer, and strategic buyer - and why most people are stuck in the wrong category their entire career
• Why 60% of businesses listed for sale never sell, and how to exploit that fact
• The 50-10-3-1 rule every serious buyer needs to understand before looking at a single listing
• How to use vendor financing, share swaps, and capital injection to acquire without a war chest
• Why Brad asks "are you looking for investors?" instead of "are you looking to sell?" - and why that one shift changes everything
• The three things to audit the moment you take ownership - and why missing one will bleed you dry
• The due diligence mistakes that kill deals, crater offers, and send serious buyers running

And the one line that should be on every buyer's wall:

The deal of the century comes along every week. Don't fall in love with the business. Fall in love with the deal.

Most buyers skip the process, buy the dream, and wonder why the numbers never add up.

This episode is the antidote.

🎧 Hit play - this is thirty years of buying, selling, and coaching condensed into one conversation that hands you the whole playbook.

Episode Highlights

05:40 - Why Strategic Acquisitions Beat Financial Ones 

09:07 - Goals Before Deals

13:21 - The Business Brad Paid Double For That Was Still Only 10% of What It Was Actually Worth

17:09 - The Japanese Coffee Company That Bought a Cleaning Business Just to Get to Its Customers

21:36 - How Brad Does Deals Nobody Else Is Bidding On 

30:13 - The Three Things to Audit the Moment You Take Over Any Business 

31:37 - The One Mistake That Kills Most Exits Before They Even Start 

37:42 - The Client Who Came In at an Eight-Times Multiple and Left With Thirty-Seven 

40:46 - How Brad Resets an Offer After Finding Skeletons in Due Diligence 

Key Takeaways

➥ Know your goals and your rules before you look at a single listing. Without them, every decision you make will be emotional. And emotional decisions in acquisitions are expensive ones.

➥ There are three types of buyers - job buyer, financial buyer, strategic buyer. Most people spend their whole career in the wrong one. The money lives in strategic, where your acquisition solves a problem your existing business already has.

➥ Don't just value the EBITDA. Trademarks, licenses, intellectual property, trading rights - these are assets most sellers never quantify and most buyers never ask about. That gap is where the real deals are made.

➥ Sixty percent of businesses listed for sale never sell. The person across the table from you is more motivated than they're letting on. Patience and preparation are your biggest negotiating tools - not tactics or pressure.

➥ Vendor financing, share swaps, and capital injection are how serious acquirers move without needing a pile of cash. A bank will lend you money to buy a profitable company. They won't lend you money to run a marketing campaign. Use that.

➥ The moment you find something in due diligence that doesn't match what you were told, go back immediately. Not as a ploy. Not as a tactic. Because the numbers you built your offer on are no longer real - and pretending otherwise only hurts you later.

➥ Fall in love with the deal, not the business. If you can't brag about the structure, the multiple, the terms - it's probably not the right transaction at this point in time. The deal of the century comes along every week. Wait for one worth bragging about.

About Brad Sugars

Brad Sugars is the founder, chairman, and president of ActionCOACH,  the world's number one business coaching franchise with 1,000+ offices in 80 countries. A self-made multi-millionaire from Brisbane, Australia, Brad started his first business at university, became known as "The Turnaround Kid," and has since coached over a million business owners worldwide. Author of 16 books including Billionaire in Training and Buying Customers, Brad's entire philosophy centres on one principle: a true business is a commercial, profitable enterprise that works without you.

Connect with Brad Sugars

➥ https://www.actioncoach.com/

➥https://www.linkedin.com/in/bradsugars/

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

That's not a marketing strategy. That's exactly what happened when 21-year-old Ovi Shekh posted Wisdomic AI on Acquire.com and watched his inbox fill up faster than he expected.

Ovi is a CS student from Dhaka, Bangladesh. He's already exited two businesses before most people his age have submitted a single job application. His first exit came almost by accident - a COVID-era grocery delivery startup, quietly acquired after the buyer tracked him down on Instagram. His second was Wisdomic AI. An AI-powered academic research tool he'd spent eight months building. Ten thousand signups. Nineteen hundred active users. Fifty-plus universities. And a product he genuinely didn't want to let go of.

But he listed it anyway. Just to see.

Fifty-two inquiries later, he had a signed LOI with his chosen buyer. And then a better offer showed up. More money. Different vision. And Ovi walked away from it.

Because here's the thing most first-time sellers never think to use as a dealbreaker - vision alignment. Not the highest number. Not the cleanest terms. Whether the buyer actually believes in what you built and will carry it forward the right way. That was the filter. That was the whole decision.

The buyer Ovi chose went on to raise $700,000 using the asset Ovi sold him. Let that sit for a second.

In this episode, Jaryd sits down with Ovi to unpack how a 21-year-old from Bangladesh navigated two exits, turned down a better offer on purpose, and figured out the rules of the acquisition game earlier than almost anyone around him. How he valued an eight-month-old SaaS with no ARR and a niche user base that didn't behave like typical consumers. Why he applied to Y Combinator eight times, got rejected every single time, and what that finally told him about where his leverage actually lived. And the one thing he says nobody tells you when you're building - that you don't get rich owning a startup. Only selling one.

Most founders fall in love with their product and never let go. Ovi fell in love with his, listed it just to see what would happen, and walked away with a lesson worth more than the exit itself.

🎧 Hit play - this is what acquisition-minded thinking looks like when it starts at 21.

Episode Highlights

00:55 - Why Ovi Listed Wisdomic AI And Got 52 Inquiries Almost Immediately

02:55 - The Moment a Better Offer Arrived After the LOI Was Signed - And Why He Turned It Down Anyway

06:43 - How You Value an Eight-Month-Old SaaS With No ARR and a Niche User Base That Doesn't Behave Like Normal Consumers

09:36 - The COVID Grocery Startup, the Hub and Spoke Model, and the Instagram DM That Turned a Shutdown Into His First Exit

12:33 - Eight YC Rejections, a Grant But No Funding, and the Moment He Realized Bangladesh Was the Ceiling

18:04 - What He Told His University Audience About Leverage, Product Market Fit, and Finding a Buyer With Complementary Skills

22:12 - The One Piece of Advice That Has Nothing to Do With Business - And Everything to Do With Why You're Building

Key Takeaways

➥ Vision alignment beats the highest offer. Price gets you to the table. The right buyer gets your product to where it was always supposed to go. Know the difference before you sign anything.

➥ Your unfair advantage is the thing you build from. Ovi could code. His co-founder could market. Know what you bring that nobody else in the room has - and build your exit strategy around it.

➥ A low churn rate is a valuation argument. Researchers don't bounce like casual app users. When your user base is sticky by nature, that's a story worth telling every buyer in the room.

➥ You don't get rich owning a startup. Only selling one. Building is how you create the asset. The exit is how you actually collect. Most founders confuse the two until it's too late.

➥ An MVP with product market fit is worth more than a perfect product nobody's using. Acquirers and investors are buying traction, not polish. Ship it, prove it sticks, then have the valuation conversation.

➥ Retaining a small equity slice post-exit is insurance, not greed. Five percent of something that raises $700K is a very different number than 100 percent of something you can no longer scale alone.

➥ Time is the one thing money cannot buy back. Twelve-hour days in Claude Code mean nothing if nobody's waiting for you when you close the laptop. Build the business. But don't lose the life funding it.

About Ovi Shekh

Ovi Shekh is a 21-year-old entrepreneur and CS student from Bangladesh who has already exited two businesses. He co-founded GetGroceryBD during COVID - an on-demand grocery delivery platform acquired by Bponi in 2023. He then built Wisdomic AI, an AI-powered academic research tool that grew to 1,900+ users and 50+ universities before attracting 50+ buyers on Acquire.com and successfully exiting. Now building Arklab AI and actively investing in small businesses, Ovi represents a new generation of acquisition-minded founders.

Connect with Ovi Shekh

➥ https://www.ovishekh.com/
➥ linkedin.com/in/ovishkh 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ FREE Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Online Business Due Diligence Services - https://buyingonlinebusinesses.com/duediligence

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Not the highlight reel. The chargebacks, the 95% traffic drops, the seller-financed deal you hand back four months in because you simply can't make it work. The slow, painful realization that passive income was never really the point - ownership was.

Brock Yates has been buying online businesses since 2012, starting with a $3,000 turtle website he found on Flippa with zero SEO knowledge and zero plan. By the time he quit his day job in Switzerland to go full-time, he had a portfolio of content sites generating more than his salary. Then the Google Helpful Content Update hit. And then ChatGPT changed everything.

In this episode, Brock doesn't just share what went wrong - he shares what he actually did to crawl back, adapt, and build something more resilient on the other side.

In this episode, you'll learn:

• Why Brock handed a $220K–$280K e-commerce acquisition back to the seller after four months - and what he'd do completely differently today
• The one thing every first-time buyer underestimates: the seller's institutional knowledge and what disappears the moment they walk out the door
• How a 95% traffic drop forced him to rethink content sites entirely - and why the turtle website outlasted everything else in his portfolio
• The WooCommerce vs. Shopify decision that's shaping his entire content-to-commerce strategy now
• How he used ChatGPT to build a free tool in 20 minutes that took a brand-new GM vehicle site from zero to 1,000 email subscribers - and counting
• Why buying a business to "own for 10 years" changes every decision you make from day one
• The niche-selection mistake that kills most content sites before they ever have a chance to grow

Whether you're sitting on a content site wondering what to do next, or you're a first-time buyer trying to avoid the mistakes most people only learn the hard way - this conversation is one of the most honest, practical accounts of what building an online portfolio actually looks like across a decade.

🎧 Hit play - this is what 10 acquisitions of real-world experience sounds like when someone's willing to tell you all of it.

Episode Highlights

03:29 - How a $3K Turtle Website Turned Into His First Online Business and Had Its Money Back Within 12 Months

08:24 - The Vegas Breakfast Deal: Why It Became His Most Expensive Education

11:49 - The Real Cost of Skipping Due Diligence on a $250K Acquisition

15:26 - Why Handing the Business Back to the Seller Was the Best Decision Available

17:43 - How the Google Helpful Content Update Wiped Out a Portfolio He'd Spent Years Building - Right After He Quit His Day Job

24:31 - Why the One Property He Built Survived the Crash While Every Listicle-Only Site Quietly Died

31:45 - The 20-Minute ChatGPT Tool That Beat Months of Pinterest Ad Spend

Key Takeaways

➥ The seller's knowledge is part of the asset - and it walks out with them. Before you close, map every decision that still lives inside the founder's head.

➥ Due diligence isn't verifying numbers - it's finding costs that aren't on the P&L yet. Chargebacks. Expiring inventory. Hidden fees. The surprises that break deals hide in the operational layer.

➥ Seller financing only works as well as the relationship behind it. When Brock couldn't make payments, a real relationship meant a clean exit, not a lawsuit.

➥ The sites you focus on survive. The ones you abandon don't. In a portfolio, attention is the most important thing you allocate.

➥ Thin content was never a business, it was a bet on Google never changing the rules. Build for the reader. The algorithm catches up eventually.

➥ If your content site has traffic, it has buying intent. Capture it. WooCommerce on the root domain. Google Merchant Center. Set it up before you think you need it.

➥ The best tool to build is the one you were frustrated you couldn't find yourself.

About Brock Yates

Brock Yates is an independent publisher behind GMT Central and AllTurtles, where he builds practical content brands for enthusiast audiences. His work focuses on SEO, content strategy, and adapting niche websites to major changes in search.

Connect with Brock Yates

➥https://gmtcentral.com/

➥https://www.allturtles.com/

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

While most buyers wait for the AI dust to settle, the ones who understand what’s happening are quietly buying assets at discounts that won’t exist a year from now.

The shift isn’t theoretical. Digital Trends lost 90% of its Google traffic - from 8.5M clicks to 65K. HubSpot lost nearly half its organic traffic in two months. Atlassian dropped 35% as enterprise usage declined. Salesforce fell 28%. And Monday.com replaced a 24-person sales team with AI in minutes.

This has already happened.

So the real question isn’t if AI is reshaping the market - it’s whether you know which businesses are still worth buying, how to price the risk, and when to walk away.

In this episode, Jaryd breaks down how to spot hidden value in “declining” assets, why some SaaS models are collapsing, and how AI risk can be used as leverage - not fear. Because the buyers winning right now aren’t panicking or waiting.

They’re moving with a strategy.

🎧 Hit play - this is your edge in an AI-disrupted market.

Episode Highlights

00:47 - A practical guide to which business models are winning vs. losing in the AI era.

04:06 - Can AI cheaply replace this business’s core value?

06:21 - Digital Trends (-90% traffic) and HubSpot (major drop) show the new reality for content sites.

09:19 - SaaS shake-up: Atlassian, Salesforce decline; Monday.com replaces sales with AI.

16:42 - Branded e-commerce with real equity is the most AI-resistant play.

21:31 - AI-hit businesses = best deals if you use risk to negotiate, not walk away.

26:52 - Klarna shows AI can replace support at scale -cutting costs post-acquisition.

Key Takeaways

➥ Always ask: Can AI replace this business cheaply? If yes, don’t walk - reprice and structure with earnouts.

➥ Single-source traffic (like Google) is now a dealbreaker. Value current performance and build growth outside SEO.

➥ Use AI risk as leverage - lower the price and tie payments to future performance.

➥ AI-resistant businesses have proprietary data, a strong brand, and real customer relationships.

➥ Distressed, AI-hit businesses are undervalued - but only if you have a clear turnaround plan.

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Ace Chapman has done 200+ acquisitions - and he'll tell you the numbers are almost never the point.

Ace has been in this game since the dot-com bubble. He almost sold a stock market simulator to a little Nebraska company called Omaha Securities - before it became Ameritrade. He got out of a real estate business right before 2008 hit. He's not lucky. He's built a framework for thinking about business ownership that most acquisition guys never arrive at, no matter how many deals they close.

But here's where it gets interesting.

Right now, while everyone else is hunting online businesses in the U.S., Ace is doing something completely different - buying offline deals in Latin America, where business brokers don't exist and most owners don't even know selling is an option. Hotels. Spas. Mental health clinics. Panama. Colombia. Argentina. He walked into a hotel recently and heard the front desk pitch his own spa to a guest checking in.

In this episode, Jaryd sits down with Ace to unpack why he thinks every business is just inventory - and why holding on too long is the real risk most buyers never talk about. How he structures equity deals so he never has to build anything from scratch. And what a real portfolio actually looks like when you stop confusing operating businesses with wealth.

Most buyers are waiting for the market to calm down before they make a move.

Ace just went and found a completely different market - one where nobody else is even looking.

🎧 Hit play - this is what 200 acquisitions of hard-won experience actually sounds like in practice.

Episode Highlights

[03:33] - Ace explains why retirement is the riskiest first-timer move most people ever make - and why most people don't realize it until it's too late.

[11:38] - The mindset shift that changed everything: why buying a business to grow it actually defeats the whole purpose of buying in the first place.

[15:45] - Ace reveals why he's moved almost entirely into offline, international deals - and why Latin America is where the real opportunity gap exists right now.

[26:00] - The tanning salon roll-up story: how Ace transferred managers between two businesses to fix operations and marketing - without hiring a single new person.

[31:00] - The "Chairman Strategy" explained: why Ace treats every business need as an acquisition problem, not a hiring problem.

[37:27] - Why every business is going to fail eventually - and why the most rational thing you can do is always be working toward the exit.

[39:09] - Ace's reframe that changes how you hold a portfolio: businesses aren't assets to protect. They're inventory.

Key Takeaways

➥ Every business will eventually go out of business - even the best ones. 99% of the original S&P 500 companies are gone. The only question is whether you exit on your terms or theirs.

➥ The real portfolio isn't operating businesses - it's what you build outside them. Royalties, equity positions, brokerage accounts. Ace took a group of royalties public. That's the game after the game.

➥ Stop hiring. Start acquiring. Ace transferred one manager between two tanning salons instead of hiring twice. When he needed marketing, he bought social media accounts in the niche. You don't build what you can buy.

➥ Timing the exit matters as much as building the business. Ace nearly missed the Ameritrade deal in 2001 and almost held through the 2008 real estate crash. After 200+ acquisitions, his rule is simple - you're always working toward the exit.

➥ Go where the buyers aren't. In the U.S., acquisition culture is loud and crowded. In Panama, Colombia, and Argentina, business brokers don't exist. Sellers don't know "multiples" is even a word. That gap is the opportunity.

About Ace Chapman

Ace Chapman has been in Micro Private Equity for decades! Buying his first business at 19 with just $3,000, leveraging it into a $70,000 acquisition. Over 25+ years he has personally completed 200+ acquisitions across online and offline businesses, and built a 6-figure monthly income from his portfolio. Founder of Partners Equity Fund and author of The Ace Formula, Ace now consults founders and investors on building wealth through strategic business acquisitions. He's based in South America and coaches clients globally.

Connect with Ace Chapman

➥https://www.linkedin.com/in/ace-chapman/

➥http://www.acechapman.com/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

That's not a rhetorical question. That's exactly how Karl Hughes bought his first agency.

While every other buyer was refreshing broker listings and fighting over the same tired deals, Karl built a spreadsheet, started cold DM-ing podcast production founders on LinkedIn, and had fifty conversations most people would've deleted without a second thought. No broker. No bidding war. No competing offers. Just Karl, a thesis, and the patience to work a room that nobody else had walked into yet.

One of those conversations turned into a sub-million-dollar acquisition at 2.7x SDE -a healthy, cash-flowing business with clients who'd been around for five-plus years. The seller had never seen a competitor's P&L in his life. Karl had seen twenty before he ever made the call.

But here's where it gets interesting.

That deal was just the beginning. Since then, Karl has been quietly building a portfolio of niche marketing agencies -the kind that are too small for private equity, too owner-dependent for most buyers, and too overlooked for anyone to notice the opportunity hiding inside them. Financing deals creatively. Targeting founders who are ready to move on. And figuring out in real time what it actually takes to merge two similar agencies without torching the clients that made them worth buying in the first place. 

In this episode, Jaryd sits down with Karl to unpack why small agencies rarely get a real exit -and why that's the opportunity. How Karl showed a seller the actual debt math before making an offer and closed with trust instead of pressure. And what he'd do completely differently if he had to start the integration process over again from day one.

Most buyers wait for a clean deal to fall into their lap.

Karl just built his own pipeline and went to find it.

🎧 Hit play - this is what a quiet, deliberate acquisition strategy actually looks like in practice.

Episode Highlights

03:30 -Why Small Agencies Never Get a Real Exit -And Why That's Your Opportunity

09:29 -The LinkedIn Cold DM Strategy That Found a Deal Nobody Else Was Looking At

17:00 -The P&L Advantage: How Karl Saw 20 Competitor Financials Before Making a Single Offer

21:20 -Showing the Seller the Debt Math: The Transparency Move That Closed the Deal

33:28 -Karl Flips the Script and Asks Jaryd the Question Every First-Time Buyer Is Afraid To Ask

37:00 -Debt vs Equity: What Structure Actually Makes Sense for Small Agency Deals

39:00 -Never Buy a Distressed Agency First -Unless This One Condition Is Already Met

Key Takeaways

➥ Being an operator is your unfair advantage. Karl didn't walk in as a finance guy with a briefcase. He walked in as someone already running a real agency. That credibility alone got doors open that cold outreach never could.

➥ Off-market deals aren't found -they're built. Karl spent months talking to founders who had no intention of selling. Some came back a year later. Patient relationship-building in one vertical is how you end up as the only offer on the table.

➥ See more P&Ls than anyone else in the room. Karl reviewed 20 competitor financials before making a single offer. The seller had seen zero. That knowledge gap isn't an edge you stumble into -it's one you build deliberately.

➥ Transparency closes deals faster than pressure ever will. Karl showed sellers the actual debt math behind his offer price. Not to impress them -to build enough trust to close without a broker, a bidding war, or months of back and forth.

➥ Shadow the team before you ever think about cutting it. The most valuable things a client-facing employee does are invisible until they're gone. Let both teams learn from each other first. The redundancies will surface on their own.

About Karl Hughes

Karl Hughes is a former CTO turned serial agency acquirer. He founded Draft.dev in 2020 -a technical content marketing agency -and scaled it to $2.5M in revenue before stepping back from day-to-day operations. In 2023, he partnered with a co-buyer to acquire The Podcast Consultant without a broker, sourcing the deal directly via LinkedIn outreach after reviewing 200+ agencies. He now hosts the Retained Trust podcast and is actively building a portfolio of niche digital service businesses in the $1M–$5M revenue range.

Connect with Karl Hughes

➥ https://www.karllhughes.com/  

➥https://www.linkedin.com/in/karllhughes/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

That's not luck. That's Qayyum Rajan.

In this episode, Jaryd sits down with Qayyum -founder, developer, and holdco builder -who turned a single LinkedIn cold message into a PE exit, watched that same PE firm quietly forget his business existed, bought it back for $100, and relisted it on MicroAcquire while two buyers bid against each other in real time.

But here's where it gets really interesting.

After the exit, while everyone else was running away from content sites -Google had just torched their traffic with the helpful content update -Qayyum was running toward them.

Buying burnt-out founders' blogs for $10K–$50K. Merging them. Building newsletters nobody had touched. Going faceless on YouTube. And quietly turning the whole thing into a cash-flowing media holdco that made back its entire investment in nine months.

You'll learn how he evaluates and closes acquisitions in under 24 hours, why "domain authority and love" are his two non-negotiables, what it actually looks like to consolidate three sites under one domain without destroying the traffic -and why he thinks the biggest opportunity in content right now is hiding inside the businesses everyone else already walked away from.

Most buyers wait for the perfect business.

Qayyum just knows how to read the ones everyone else missed.

🎧 Hit play -this is what building a holdco from the wreckage actually looks like.

Episode Highlights

02:56 The LinkedIn Cold Message That Started a PE Exit Nobody Saw Coming

05:35 The $2,000 Credit Card Lien That Almost Blew Up a Million-Dollar Deal

12:02 Bought Back for $100: How Qayyum Got His Own Business Returned to Him

14:45 The MicroAcquire Bidding War -Two Buyers, Five Days, Real-Time Updates to His Wife

18:32 Why He Started Buying Content Sites Right When Google Was Destroying Them

28:52 Wealth Awesome -Buying a Finance Blog for 1x Revenue and Making It Back in Nine Months

38:22 The $20K Deal He Walked Away From -and Built Himself in a Week Instead

Key Takeaways

➥ You don't need a perfect business -you need an underutilized one. The real opportunity is in channels the previous owner never touched: newsletters, YouTube, social. That's where the upside is hiding.

➥ Domain authority and founder love are the two things worth paying a premium for. Everything else can be built. Backlinks and brand equity take years -you can't manufacture them overnight.

➥ When Google cuts your traffic, don't fight it -diversify around it. Bing, newsletters, YouTube Shorts, and faceless video are quietly outperforming SEO for content operators right now.

➥ Moving fast is a competitive advantage in small acquisitions. Most sellers aren't just looking for the best price -they want certainty. Close in 24 hours and you win deals slower buyers never even get to.

➥ A holdco only works if you're ruthless about focus. Shelve what isn't winning so you can double down on what is -spreading thin is how good acquisitions quietly die.

➥ Face-brand content sites are one of the most underpriced assets in the market right now. Use the dependency as a negotiation lever to lower the price, then go faceless and build something that can actually be sold.

➥ The exit multiple is everything -and it's timing. Qayyum sold at 20x earnings at the peak of the market. One year later, that same business lists for 4–5x. Getting out at the right moment matters as much as building the right thing.

About Qayyum Rajan

Qayyum Rajan (known as 'Q') is a CFA Charterholder, former portfolio manager, and serial online business acquirer. He founded ESG Analytics in 2017 -sold it to PE, bought it back for next to nothing when the acquirer went under, and sold it again for six figures. He then built his own holdco, acquiring Wealth Awesome (a leading Canadian personal finance publication with 20,000+ readers) and Worqstrap, amalgamating two separate businesses into one. Based in British Columbia, he sits on the Fintech Advisory Committee for the BC Securities Commission.

Connect with Qayyum Rajan

➥ https://wealthawesome.com/

➥https://www.linkedin.com/in/qayyumrajan/

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Most first-time buyers obsess over finding the perfect business - but the ones who actually close deals? They obsess over reading the business correctly.

In this case study episode, Jaryd Krause sits down with Jan, a Buying Online Businesses graduate who went from consuming YouTube content and podcasts to acquiring a six-figure health and beauty e-commerce brand - and lived to tell the full, unfiltered story.

Jan brought something most buyers don't: seven-plus years of digital marketing and DTC experience. And she used every bit of it to spot the green flags hiding inside what most buyers would have walked away from.

You'll learn how Jan evaluated over 100 listings, deep-dived on 30 businesses before finding the one, negotiated inventory she didn't want out of the purchase price, and immediately unlocked growth through paid ads and an underutilized email list the previous owners barely touched.

You'll also hear why red flags aren't dealbreakers - they're filters - and how the right background can flip a liability into your biggest competitive edge.

If you're a first-time buyer trying to figure out what "good" actually looks like before you sign anything, hit the 🎧 Play button.

Episode Highlights

09:33 The Magic Number: How Many Businesses You Actually Need to Look at Before You Buy

12:22 Why Red Flags Are Just Green Flags in Disguise

15:40 The Inventory Negotiation Move That Saved Jan Thousands at Closing

19:16 The Untapped Email List That Was Sitting There Printing Money

22:00 Tariffs, Trouble, and Why Customer Diversity Saved This Business

28:31 The One Thing Jan Would Do Completely Differently on Her Next Acquisition

Key Takeaways

➥ Red flags aren't automatic dealbreakers - the right background turns someone else's liability into your biggest competitive advantage.

➥ An underutilized email list is cash sitting on the table - if the previous owner wasn't sending weekly, you're inheriting free revenue from day one.

➥ Negotiating out slow-moving inventory before closing isn't optional - it's one of the easiest ways to reduce your purchase price on the spot.

➥ Keeping previous owners involved beyond the handover isn't a weakness - it's the move experienced acquirers wish they'd made sooner.

➥ Waiting for the "perfect" market conditions before buying is the riskiest strategy of all - the real cost is the time, growth, and learning you never get back.

About Jan Patel

Jan is a BuyingOnlineBusinesses.com graduate who went from digital marketing for large scale ecom brands in her day job. To now acquiring, owning and scaling her own ecommerce business. 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Stuart Faught has done it 20 times. And he'll tell you - that's exactly the wrong way to think about it.

Because what most SaaS founders don't realize… is that the real money isn't in building forever.

It's in knowing exactly when to let go.

Like the business he built, took to 100K ARR… and sold in 30 days flat.

Or the deals where buyers showed up with zero-down offers and five-year payment plans… and got politely - but firmly - shown the door.

Or the biggest mistake first-time SaaS buyers make - falling in love with the tech… when the only thing that actually grows the business is sales.

In this episode, Jaryd Krause sits down with Stuart Faught - serial micro SaaS entrepreneur who has built and exited over 20 software businesses across verticals like dental, HVAC, med spas, and home care. All bootstrapped. All profitable. All sold.

And this one gets real.

Into why Stuart never scales past 100K ARR before selling - and why that's a feature, not a limitation. Into what he'd look for if he were buying a SaaS business tomorrow - and the red flags that would make him walk. Into why non-technical buyers are actually better positioned to grow software companies than most people think.

But more importantly…

Stuart breaks down the exact repeatable system behind 20 clean exits - what makes a deal close fast, what kills it dead, and why simplicity is the most powerful thing a seller can offer a buyer.

No fluff. No theory. No "someday I'll do it big."

Just 20 exits deep of hard proof - from someone who's figured out the game… and keeps winning it.

🎧 Hit play - this is what a real SaaS exit machine actually looks like.

Episode Highlights

02:40 The 50K–100K ARR Sweet Spot: Why Stuart Sells Before Most Founders Even Get Started

07:04 The 5X Formula: How Stuart Consistently Prices and Closes 20 SaaS Exits

10:54 The Deal Structure That Serious Buyers Use (And the One That Gets You Ghosted Immediately)

16:09 You Don't Need to Be Technical to Own a Tech Company - Here's What Actually Matters

18:51 How to Do Due Diligence on a SaaS Business Like Someone Who's Sold 20 of Them

21:04 The Secret to Growing Any Sub-$1M Business That Most Buyers Completely Overlook

23:08 Why First-Time Founders Make the Best Buyers - And How Stuart Finds Them Before Listing

Key Takeaways

➥ You don't need to be technical to build, grow, or buy a SaaS business - sales and marketing skills matter far more.

➥ Targeting a 50K–100K ARR sweet spot before exiting allows for faster, cleaner deals without burnout or over-scaling.

➥ A 5X multiple on top-line revenue is a realistic and repeatable benchmark for micro SaaS exits in today's market.

➥ Keeping deal structures simple - at least 50% cash upfront with the remainder collected within 90 days - attracts serious buyers and closes deals faster.

➥ Talking to 3–5 customers during due diligence reveals more about a business's true health than financials alone ever will.

➥ Being an easy, honest, and respectful buyer is one of the most underrated competitive advantages in any acquisition process.

➥ Niching into a vertical SaaS doesn't trap you - adjacent markets and close-cousin industries create natural expansion paths when growth plateaus.

About Stuart Faught

Stuart Faught is a serial SaaS entrepreneur who has built and sold 20+ micro-SaaS businesses across verticals including dental, orthodontics, HVAC, med spas, and home care. Known for his rapid exit strategy, Stuart closes most deals in 30-45 days by creating clean documentation and targeting niche markets. He's founded multiple companies including Praze, PatientSnap, Caddy, and Covington.ai. Stuart specializes in vertical SaaS solutions and teaches founders how to build for exits, not endless scaling.

Connect with Stuart Faught

➥ https://www.linkedin.com/in/stuart-faught-59a5a76b/

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Kevin Peterson has done over 50 acquisitions - and he’ll tell you that’s exactly how people lose money.

Because what brokers don’t tell you… 

is that the real risk isn’t the numbers?

It’s what’s missing behind them.

Like the SaaS deal that looked perfect on paper…

until the entire team walked out right after closing.

Or the “growth opportunity” that was actually just an audience no one had ever monetized.

Or the biggest trap of all - buying a business without a clear thesis… and hoping it works out later.

In this episode, Jaryd sits down with Kevin - founder of Webfolio Management - who’s spent the last 12+ years acquiring, operating, and scaling digital businesses across SaaS, content, and eCommerce.

And this one goes deep.

Into the real due diligence signals most buyers miss. Into how AI is quietly changing what businesses are worth buying - and which ones are becoming obsolete. Into the hidden risks inside “easy wins” like audience monetization and roll-ups.

But more importantly…

Kevin breaks down the exact thinking behind building a portfolio that doesn’t just grow - but actually survives.

No hype. No shortcuts. No theory.

Just hard-earned lessons from someone who’s done the deals, made the mistakes… and kept going anyway.

🎧 Hit play - this is what buying businesses really looks like.

Episode Highlights

02:27 The Career Pivot That Changed Everything – From 20 Years in Consulting to Buying Online Businesses

03:36 From $50K Deals to 7-Figure Acquisitions – How Kevin Built a 50+ Deal Track Record

06:08 The Hidden Value Most Buyers Miss – Untapped Audiences That Can Instantly Increase Revenue

09:22 The Deal That Looked Perfect… Until the Entire Team Walked Out After Closing

11:36 SaaS Due Diligence Simplified – The 4 Metrics That Actually Matter

17:01 The KPI That Signals It’s Time to Sell (Before the Business Declines)

22:14 What NOT to Buy in the Age of AI – And Where the Real Moats Still Exist

Key Takeaways

➥ The best deals aren’t found - they’re filtered. Without a clear acquisition thesis, you’ll chase instead of build.

➥ If the business can’t run without the founder, you didn’t buy an asset - you bought a job.

➥ The real cost isn’t the purchase price. It’s the capital required to grow the business after you own it.

➥ Conversion rate and churn will tell you the truth before revenue ever does - watch them closely.

➥ AI is lowering the barrier to entry. If your business can be easily copied, it’s already at risk.

➥ The biggest hidden upside in acquisitions is often an under-monetized audience.

➥ Most founders sell too late. The right time to exit is before growth starts getting harder.

About Kevin Peterson

Kevin Petersen is a serial entrepreneur and founder of WebFolio Management, a portfolio vehicle that acquires and operates small SaaS companies on behalf of investors and himself. 

Since getting started in the web-business market he has acquired dozens of internet businesses (including Picreel) and refined a deliberate, metrics-driven approach to sourcing, cleaning financials, and scaling recurring-revenue products. 

Kevin focuses on building investor-grade units with clean books and repeatable growth processes, then deciding whether to hold, scale, or exit. 

He frequently coaches other buyers and investors on building SaaS portfolios, and his playbook centers on deliberate deal selection, clean financial segmentation, and operational systems that allow multiple assets to be managed without chaos. 

Connect with Kevin Peterson

➥ https://www.linkedin.com/in/kevinpetersen1/

➥saastermind.net

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Nathan Gwilliam spent 30 years learning why that belief is exactly what destroys exits.

Three businesses built. Three exits are closed. And a front-row seat to some of the most painful – and profitable – lessons the entrepreneurial world rarely talks about out loud.

Like the time Disney came knocking... and his partner wouldn't even let them see the financials.

Or the earn-out that looked like a windfall on paper - until someone else was making all the decisions.

Or the phone call on a Sunday morning, right before church, that changed everything about why he sold Adoption.com.

In this episode, Jaryd sits down with Nathan – the founder behind the most visited adoption platform in the world – for one of the most honest, human, and genuinely surprising conversations we've had on this show. Because yes, you'll get the tactics. The roll-up acquisition strategy that turned his biggest competitor into his biggest asset. The 50/50 partnership trap that quietly kills deals before they ever start. The exact moment a founder should seriously consider selling – even if the timing feels wrong.

But this one goes somewhere most business podcasts are too scared to go.

Into the Sunday morning phone calls. Into making decisions from love instead of fear. Into what it actually costs – emotionally, financially, spiritually – to build something real and then let it go.

Nathan doesn't dress it up. He doesn't hide the mistakes. And he doesn't pretend the journey was clean.

And that's exactly what makes this one unmissable.

🎧 Hit play. This is the exit conversation nobody else is having.

BONUS: Get a free 30-day trial of Nathan's all-in-one podcasting platform at PodUp, or head to podallies.com to book a free 45-minute podcast strategy session – directly with Nathan himself.

Episode Highlights

07:08 The $100 Million Yahoo Offer That Got Turned Down – And the Company That Was Dead 12 Months Later

10:31 The Sunday Morning Phone Call That Changed Everything About Why He Sold Adoption.com

15:00 How Nathan Bought His Biggest Competitor Without a Single Dollar Down

18:21 Built From Scratch in 24 Months – Then Disney Tried to Buy It

23:06 The Earn-Out Trap: Why Nathan Would Walk Away From Millions Before He'd Ever Sign One Again

27:17 The 18x EBITDA Offer a Partner Killed Before Negotiations Even Started

27:52 Why a 50/50 Partnership Is Quietly the Most Dangerous Deal Structure in Business

34:00 Love-Based vs Fear-Based Decisions – The Framework That Changed How Nathan Runs Everything

37:02 How Nathan Turned His Biggest Competitor Into His Biggest Asset (Without Paying Upfront)

Key Takeaways

➥ When your business is worth more to someone else than it is to you - that's your signal to sell.

➥ Never sign an earn-out where the buyer makes all the decisions. You're handing them your money and your future in the same handshake.

➥ A 50/50 partnership sounds fair until you need to make a decision that actually matters.

➥ Your biggest competitor might be your best acquisition – buy them, absorb their traffic, and stop splitting the market.

➥ The best acquisitions don't require a big upfront payment – structure it right and the asset pays for itself.

➥ Businesses don't always go up. The founders who wait for the perfect moment often end up selling at the worst one.

➥ Brokers create competition. Competition creates leverage. Never negotiate a major exit one-on-one if you can avoid it.

➥ Lead with genuine value and build revenue around it – the freemium model is still one of the most powerful plays in digital business.

➥ The best business decisions aren't made from fear. They're made from love – for your partners, your customers, and the impact you're trying to create.

About Nathan Gwilliam

Nathan Gwilliam is a serial entrepreneur who has created and sold three digital ventures, including Adoption.com, the world’s most visited adoption platform. He grew major online communities and digital properties, and later sold Adoption.com to the Gladney Center for Adoption. Today he leads PodUp, an all-in-one podcasting platform that recently raised significant funding. Nathan’s unique journey – building, scaling, selling and reinventing digital businesses – gives him deep insight into acquisitions, growth strategy, and what it REALLY takes to exit for maximum value.

Connect with Nathan Gwilliam

➥ https://podup.com/ 

➥ https://podallies.com/   

➥ https://www.linkedin.com/in/nathangwilliam/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

No safety net. No backup plan. A full-time military career, seven kids at home, and a lender who pulled out mid-deal.

That's exactly where Michael Simpson found himself.

In this episode, Jaryd Krause sits down with Michael Simpson - a National Guard serviceman who bought an 18-year-old e-commerce business using SBA financing, survived a near-collapse due diligence process, and came out the other side with a real, running business.

But he's not here to tell you it was amazing. He's here to tell you the truth.

Here's what's covered:

🏦 How he lost his SBA lender mid-transaction - and saved the deal in 48 hours

💀 The post-closing liquidity trap that blindsides almost every first-time buyer

😬 Why buying slightly bigger might have changed everything

📈 The unglamorous growth playbook keeping a 20-year-old business moving forward

This isn't a success story wrapped in a bow. It's something far more valuable - an honest account of what buying a business really costs you. In money, stress, and lessons you can't learn anywhere else.

If you're thinking about buying your first business, this might be the most important episode you listen to all year.

🎧 Hit play. Real talk only.

Episode Highlights

13:32 The SBA Pre-Approval Myth That Almost Derailed the Deal

16:15 Lender Drops Out Mid-Deal - How Michael Scrambled and Saved It in 48 Hours

19:48 The $10,000 Non-Refundable Move That Kept the Seller at the Table

21:25 The 100-Hour Business Plan That Stunned Bankers on Million-Dollar Deals

27:58 The $30,000 Tech Migration Mistake That Still Haunts Him

33:45 The Post-Closing Liquidity Trap That Catches First-Time Buyers Off Guard

35:49 Why He Had to Stop Paying Himself -  And Go Back to Work Anyway

36:27 The Brutal Truth About Buying Too Small (And What He'd Do Differently)

Key Takeaways

➥ "SBA pre-approved" listings are a marketing tactic - the real approval depends on YOU as the buyer, not just the business.

➥ Losing a lender mid-deal isn't fatal - having two banks compete for your business can actually get you a better outcome.

➥ A non-refundable deposit signals serious intent and can keep a seller loyal to you when the deal gets rocky.

➥ Post-closing liquidity is the number most first-time buyers forget - 10% down is just the starting line, not the finish.

➥ Buying too small is a trap - if the business can't cover debt service, pay for growth, AND pay you, you'll end up working for free.

➥ A obsessively detailed business plan doesn't just impress lenders - it becomes your single biggest competitive advantage in a crowded deal.

➥ Technical debt is invisible until you own it - always pressure-test the tech stack before you sign, not after.

➥ Boring, stable, decades-old businesses with loyal customer bases consistently outperform shiny, high-growth ones for first-time buyers.

➥ The real cost of buying a business isn't the purchase price - it's everything that comes after the wire transfer hits.

About Michael Simpson

Michael Simpson is a business owner, acquisition entrepreneur, and National Guard serviceman who successfully bought a business using SBA financing while balancing a full-time military role and raising seven children. 

His acquisition journey included a near-deal-ending due diligence process and the challenge of replacing his SBA lender mid-transaction. Michael brings a rare, real-world perspective on resilience, risk management, and executing an acquisition under extreme personal and financial pressure.

Connect with Michael Simpson

➥ https://x.com/Michael_in_biz   

➥ https://www.discountcatholicproducts.com/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

A former respiratory therapist and a software developer – no entrepreneurial experience, no roadmap, no idea what they were doing – decided to bet on themselves anyway. And now? They're running a lean team of 11 VAs from wherever in the world they feel like being that week.

Guatemala last month. St. Kitts for their anniversary. Belize next. You get the picture.

In this episode, Jaryd Krause sits down with Alan and Mel, a husband-and-wife duo who tried every side hustle in the book – financial lending, credit repair, online teaching – before discovering that buying an existing online business was the shortcut they'd been exhausting themselves looking for.

They used SBA financing to acquire a $1.2M business with just $65K out of pocket. They inherited 2 VAs and a chaotic operation. They were working 60-hour weeks at the start. And then – systematically, strategically – they rebuilt it, scaled it, and sold it. Profitably.

Now they're already under LOI for their next deal.

Here's what makes their story different though. Neither of them had ever owned a business before. One was in healthcare. One was in tech but still didn't think you could buy something you couldn't physically touch. They were scared, skeptical, and figuring it out in real time.

Sound familiar?

If you've ever wondered whether someone like YOU could actually pull this off – this episode is your answer.

Hit play. You'll want to hear this one.🎧

Episode Highlights

06:09 The $0 Down Deal Structure Most Buyers Don't Even Know Is Possible

15:13 How They Bought a $1.2M Business With Just $65K Out of Pocket

18:26 Why Taking 6 Months to Close Was the Smartest Thing They Ever Did

24:09 From 60-Hour Weeks to 5: The Exact Strategy They Used to Replace Themselves

29:00 The Layoff That Forced Them All In – And Accidentally Changed Their Lives Forever

33:33 They Sold the Business… and Got Bored in Two Months. Here's Why They're Back

35:33 The Raw Truth About Mindset That Most Business Coaches Are Too Polished to Say

42:12 The Wealth Loop Nobody Talks About: How One Business Funded an Entire Real Estate Portfolio

Key Takeaways

➥ You don't need industry experience to acquire a business – the learning happens after you buy, not before.

➥ SBA financing can get you into a $1.2M business with as little as $0 down if you negotiate the deal structure right.

➥ The fastest way to scale an acquisition is to document every bottleneck, then hire to eliminate them one by one.

➥ A longer closing timeline isn't a red flag – it's free due diligence that lets you watch the business perform before you own it.

➥ The moment you stop working IN the business and start building a team around it, everything changes.

➥ Buying a business where the owner is burned out is a hidden goldmine – lower price, massive upside, ready to scale.

➥ Online businesses have no glass ceiling – unlike physical businesses, growth isn't limited by location, rooms, or geography.

➥ Business cash flow funds real estate. Real estate equity funds the next acquisition. That loop, repeated, builds serious wealth.

➥ Mindset isn't a buzzword here – it's the actual difference between people who pull the trigger and people who stay stuck researching forever.

➥ Freedom isn't something you find after you build the business. It's something you design into the business from the start.

About Alan & Mel

Alan and Mell are a husband-and-wife duo who’ve turned online business acquisitions into a lifestyle of freedom and adventure. Alan, with a background in education and technology, and Mel, a former respiratory therapist with an MBA from Ohio State’s Fisher College of Business, combined their skills to acquire three online businesses—recently exiting one successfully. Their profits helped them purchase two Airbnb properties and build a third in Belize. Thanks to the flexibility of their online ventures, they recently spent a month in Guatemala and El Salvador with their daughters for a World School program. Now, they’re under LOI for their next deal and on track to acquire three new deals within the next year.

Connect with Alan & Mel

➥ https://risingphoenixfund.org/home

➥ AI content creation platform: https://wordgenius.ai/

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode, Jaryd sits down with Haytham Allos, M&A strategist, AI specialist, and one of the minds behind one of the world's first AI-powered law firms, to pull back the curtain on what's actually happening right now at the intersection of artificial intelligence and buying businesses.

And it gets wild.

We're talking AI agents that evaluate deals. Smart contracts that close them. Fractionalised ownership that lets someone invest in a business for as little as $50. A future where your AI agent negotiates with the seller's AI agent, and a human just says yes or no at the end.

But before we get there? Haytham breaks down what's happening right now. Why most buyers are still flying blind, why AI without the right prompting is actually dangerous in a deal, and the one thing that kills more mergers than bad financials ever will.

You'll discover why prompt engineering is the most underrated skill in acquisitions today, how to use AI to get an unfair edge in due diligence without replacing your gut instinct, and exactly where the smart money is already moving.

This isn't theory. This is where M&A is heading, and the buyers who understand it now are going to own the next decade.

Hit play. Your competition probably already has. 🎧

Episode Highlights

05:45 The Chainsaw Analogy: Why AI Without Experience Is Genuinely Dangerous in a Deal

09:08 The Hallucination Problem: Why AI Can Lie to You During a Deal and How to Stop It

13:57 Where AI Creates the Biggest Unfair Advantage in the Acquisition Process Right Now

16:43 Prompt Engineering: The Most Underrated Skill Every Serious Buyer Needs to Master

19:44 The Rise of Agent-First Companies: What Cursor AI's $2 Billion Valuation Tells Us About the Future

22:31 The Mindset Shift Every Business Owner Must Make or Get Left Behind

28:16 AI Agents Buying From AI Agents: The Future of M&A Is Closer Than You Think

31:12 Smart Contracts, Crypto Wallets and the Death of Bureaucratic Deal Making

35:43 Fractionalised Business Ownership: How Anyone Could Invest in a Business for $50

Key Takeaways

➥ AI without experience is like handing a chainsaw to someone who's never cut down a tree. Powerful tool. Dangerous hands.

➥ AI will hallucinate during your due diligence. If you don't know how to configure it correctly, it will confidently lie to you about the business you're about to buy.

➥ Prompt engineering is the most underrated skill in acquisitions right now. The quality of your questions determines the quality of your deal.

➥ The number one reason mergers fail isn't bad financials. It's people, politics, and ego. AI is quietly removing all three from the equation.

➥ We are shifting from AI that answers questions to AI that takes actions. The buyers who understand that difference right now will have an unfair advantage for the next decade.

➥ Smart contracts, crypto wallets, and blockchain are about to collapse the layers of bureaucracy that slow every deal down. The merger process, as we know it is on borrowed time.

➥ Fractionalised ownership is coming to business acquisitions. You won't need six figures to get into a deal. You'll need the right agent and the right wallet.

➥ The future of M&A is two AI agents negotiating a deal, presenting it to their humans, and closing it on the blockchain before a bank even answers the phone.

About Haytham Allos

Haytham Allos is an M&A and AI strategist focused on how artificial intelligence is transforming the buy-side deal process. He works at the intersection of technology, data, and acquisitions, helping investors and acquirers use AI to enhance due diligence, identify hidden risks, and make better capital allocation decisions. 

Haytham specializes in applying AI tools across deal sourcing, financial analysis, operational review, and post-acquisition decision-making.

Connect with Haytham Allos

➥ https://vikk.ai/

➥ https://finance.yahoo.com/news/vikk-ai-selected-prestigious-aws-141700773.html?guccounter=1

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode, Jaryd Krause sits down with Emmet Kilduff, founder of The Fortia Group and former investment banker at Morgan Stanley, to unpack how serious online acquisitions actually get done in the $10M to $100M range.

After 25 years in M&A, Emmet pulls back the curtain on what separates institutional buyers from everyday acquirers, and why trying to “figure it out yourself” is one of the most expensive mistakes you can make.

You’ll learn:

• The 3-stage “Flirt, Date, Marry” framework elite dealmakers use to build acquisition relationships years before a deal closes
• Why the best buyers pitch sellers, and how to create a buyer deck that makes founders want you
• The real funding structures used by strategics, private equity, aggregators, and search funds
• What’s changed since the 2021 acquisition boom, and why 100% upfront deals are basically extinct
• The truth about earn-outs (and why most are designed for buyers, not sellers)
• Why recurring revenue businesses command premium multiples, and how valuation arbitrage actually works
• How to transition from operator to owner so you can think strategically and fund bigger moves

This is not theory. This is how real capital allocators think.

If you want to understand how serious acquirers finance deals, structure terms, protect downside, and build relationships that lead to eight- and nine-figure exits, this episode is your behind-the-scenes briefing.

If you’re planning to buy, sell, or scale an online business and want to understand how institutional-level M&A actually works, hit the “Play” button.

Episode Highlights

03:12 Why Even $10M Buyers Shouldn’t Go It Alone

05:08 The “Flirt, Date, Marry” Framework for Closing Bigger Deals

08:41 How Smart Buyers Pitch Sellers (And Win Trust Fast)

12:06 The Truth About Earn-Outs (And Why Sellers Should Be Careful)

18:47 The Three Types of Institutional Buyers in the $10M–$100M Range

23:55 Why Recurring Revenue Changes Everything in Valuation

28:36 The Strategic Conversations That Should Happen Before Price Is Discussed

35:44 From Operator to Owner: Making the Shift to Strategic Thinking

40:27 Building an Advisory Board That Actually Moves the Needle

Key Takeaways

➥ Buying a $10M–$100M online business is as much about relationships and strategy as it is about money.

➥ Use the “Flirt, Date, Marry” framework: build trust early, share information progressively, and finalize only when both sides are aligned.

➥ Strong buyers actively pitch sellers—your experience, vision, and team matter just as much as your capital.

➥ Typical deal structures include 60–80% upfront with the balance via earn-outs, equity rollover, or milestone-based deferred payments.

➥ Structuring earn-outs around revenue, not profit, reduces disputes and protects long-term relationships.

➥ Recurring revenue businesses (SaaS, subscriptions, memberships) command higher multiples and offer more predictable financing.

➥ Advisory panels and mentors accelerate decision-making, reduce risk, and boost credibility with sellers.

➥ Transitioning from operator to owner requires delegation, trust, and strategic focus over day-to-day management.

➥ Patience, preparation, and network-building are the hidden factors that make or break acquisition success.

About Emmet Kilduff

Emmet Kilduff is the Founder of The Fortia Group, an M&A advisory firm specializing in the sale of eCommerce brands and digital agencies. With a background at leading Wall Street investment banks including Morgan Stanley, Emmet brings institutional-level M&A, valuation, and deal-structuring expertise to small and mid-market online businesses. 

Through Fortia, he has advised founders, buyers, and investors on acquisitions across the UK, US, and international markets, helping them navigate financing, positioning, and exits with professional rigor. 

On this episode of the Buying Online Businesses Podcast, Emmet shares how sophisticated buyers think about funding acquisitions, structuring deals, and avoiding the common mistakes that derail first-time online business buyers.

Connect with Emmet Kilduff

➥ https://www.linkedin.com/in/emmettkilduff/

➥ https://thefortiagroup.com/  

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode of the BOB Podcast, Jaryd Krause sits down with Ryan Condik - serial entrepreneur, M&A advisor at Quiet Light, and founder of Let’s Buy a Business - to unpack what actually determines who wins (and who loses) in competitive acquisition processes.

Most buyers assume it all comes down to price. Just offer more and you win, right? Not exactly.

In real-world M&A, things like certainty, speed, positioning, and creativity often matter more than a bigger number. Ryan shares behind-the-scenes stories from competitive deals, including why some buyers lost over small term differences, how one buyer won simply by building a genuine relationship with the seller, and why “certainty of close” can be far more powerful than offering an extra 10%.

You’ll learn:

• Why sellers often choose lower offers - and what they’re really evaluating
• How certainty, speed, and clean deal structures give buyers a serious edge
• Why trust and relationships can outweigh valuation
• The common buyer mistakes that quietly kill deals
• How creative structuring (including equity rollovers) can change the outcome
• Why knowing your value-add before submitting an LOI shifts the entire negotiation

Whether you’re buying your first online business or competing for premium assets in a crowded market, this episode breaks down what separates serious acquirers from hopeful bidders.

In M&A, price gets attention - but certainty wins deals.

🎧 Hit play to learn how to position yourself as the buyer sellers actually want to choose.

Episode Highlights

02:53 Why Chasing Billions Is a Trap (And What Actually Builds Freedom)

12:42 The “Seasons of Life” Framework for Smarter Entrepreneurship

18:02 The Two-Way Door Rule: How Elite Entrepreneurs Make Fast, Confident Decisions

20:17 Why Most Aspiring Entrepreneurs Fail Before They Even Start

24:34 The #1 Mistake Buyers Make When Acquiring a Business

26:24 Why Most Buyers Lose Deals (And Don’t Even Know Why)

28:46 The $400 Move That Won a Multi-Million Dollar Deal

30:45 How Relationships Beat Higher Offers in Competitive M&A

32:04 The 10% Lower Offer That Still Won the Deal

35:45 SBA Buyers vs. Serious Buyers: What Sellers Actually Want

37:38 When Paying MORE Is the Smartest Financial Decision

40:01 How to Know When You’ve Found “The One” (And Go All In)

43:00 AI, Adaptation & Why Average Operators Will Get Left Behind

Key Takeaways

➥ Traditional SEO is still the foundation—AI and GEO optimization enhance it rather than replace it.

➥ Strong brand presence and mentions across multiple platforms are now more important than backlinks for AI visibility.

➥ Being associated with reputable brands or industry leaders boosts authority and trust in AI-driven results.

➥ Content hubs and semantically related pages improve AI discoverability more than focusing on keywords alone.

➥ Social media, forums, and niche communities (Reddit, Medium, Facebook Groups) contribute to AI recognition.

➥ Balance is key: optimize for AI while maintaining usability and experience for human visitors.

➥ AI content generators can efficiently create research-backed, brand-aligned, and contextually rich content.

About Ryan Condie

Ryan Condie is a serial entrepreneur, M&A advisor and founder behind Let’s Buy a Business. He has built, bought, and sold multiple digital ventures including RentLingo via a successful acquisition.

He now helps founders master deals, due diligence and exits. Ryan also serves as an advisor at Quiet Light Brokerage, where he guides buyers and sellers through evaluations, negotiations and growth opportunities that maximize exit value. His experience blends real-world deal execution with deep strategic insight. 

Connect with Ryan Condie

➥ https://ryancondie.com/

➥ https://www.letsbuyabusiness.com/

Other podcasts with Ryan;

https://buyingonlinebusinesses.com/ep-149-why-buy-a-profitable-online-business-instead-of-staring-one-with-ryan-condie-part-1/

https://buyingonlinebusinesses.com/ep-150-title-how-to-get-started-buying-profitable-online-business-with-ryan-condie-part-2/  

https://www.youtube.com/watch?v=hRv7UHDUjYA  

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode of the BOB Podcast, Jaryd Krause welcomes back Rad Paluszak to explore the transition from SEO to GEO (Generative Engine Optimization) and what it means for founders, operators, and investors navigating an AI-driven world.

Instead of ranking pages, AI answer engines are ranking entities, brands, and trust. Rad explains why traditional SEO playbooks are breaking down, how AI engines source and rotate answers, and why brand mentions across the web now matter more than links ever did.

You’ll learn:

• Why AI engines rarely repeat the same sources—and how that changes traffic forever
• How brand authority is built through mentions, associations, and personal brands
• Why being listed alongside established brands can instantly elevate visibility
• The growing role of Reddit, social platforms, and communities in AI discovery
• How to structure content for AI without sacrificing real users
• What businesses should stop obsessing over—and what actually moves the needle
  
  

Whether you run content-heavy sites, ecommerce brands, SaaS, or are evaluating businesses to buy, this episode offers a practical framework for adapting to AI without panic—or guesswork.

AI is coming either way.
The question is whether your brand will be visible when it does.

🎧 Hit play and learn how to stay visible before the rules change completely.

Episode Highlights

03:10 Pivoting from SEO to GEO: How AI is Changing the Search Landscape

06:00 The Growing Importance of Brand Mentions and Broad Visibility

10:00 Leveraging Listicles, Social Media, and Mentions for Authority

14:00 Optimizing Websites for AI Agents vs. Human Users

18:00 Content Strategy for AI: Hubs, Semantic Relevance, and Queries

22:00 Auditing Your Site and Competitors for AI Visibility

24:00 Using AI Tools: Visibility Reports and Content Generators

29:00 Incorporating Brand Voice, Contextual Images, and Internal Linking

32:57 Scaling Your Business with AI-Driven Content Strategies

Key Takeaways

➥ Traditional SEO is still the foundation—AI and GEO optimization enhance it rather than replace it.

➥ Strong brand presence and mentions across multiple platforms are now more important than backlinks for AI visibility.

➥ Being associated with reputable brands or industry leaders boosts authority and trust in AI-driven results.

➥ Content hubs and semantically related pages improve AI discoverability more than focusing on keywords alone.

➥ Social media, forums, and niche communities (Reddit, Medium, Facebook Groups) contribute to AI recognition.

➥ Balance is key: optimize for AI while maintaining usability and experience for human visitors.

➥ AI content generators can efficiently create research-backed, brand-aligned, and contextually rich content.

About Rad Paluszak

Rad Paluszak is a digital marketing and SEO strategist focused on AI search, Generative Engine Optimization (GEO), and brand visibility in an AI-first internet. He helps businesses adapt beyond traditional rankings by optimizing for brand authority, entity mentions, and AI discovery across Google, ChatGPT, and social platforms. Rad specializes in visibility audits, content strategy, and future-proofing brands for generative search

Resource Links

➥ Ordering PROMO content packages (1 Free + 10 articles with images, internal linking and brand voice included): https://order.non.agency/content?referral_code=Buying_Online_Businesses

➥ Free AI Visibility Report: https://non.agency/en/service/ai-search-optimization-aio/?referral_code=Buying_Online_Businesses#ai_visibility

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this special episode, Jaryd Krause speaks with Ciaran Burke, COO and co-founder of Swoop, a global SME funding marketplace helping buyers access debt, equity, and grant funding across the UK, Australia, the US, and Canada. Ciaran has helped thousands of businesses secure funding by unlocking options traditional banks often miss.

You’ll learn how buyers are funding ecommerce, SaaS, and media acquisitions, what lenders really care about beyond the numbers, and why acquisition finance is now easier to access in markets like Australia and the UK.

If you are planning to buy an online business and want to understand how deals are being funded right now, hit the “Play” button! 

BONUS: Explore Swoop’s free funding platform and see if your next acquisition qualifies.

Episode Highlights

06:00 Funding Options for Acquiring Online Businesses

09:02 Understanding Deposit Requirements for Acquisitions

12:05 Setting Up a Business Entity for Acquisition Financing

15:03 Navigating Interest Rates and Loan Terms

18:02 Refinancing and Its Importance for Business Owners

21:02 Key Requirements for Loan Approval

24:38 Navigating the Financing Landscape

30:00 Preparing for Acquisition: Key Documentation

36:03 Understanding the Acquisition Process

40:01 Exploring Financing Options and Strategies

43:53 The Importance of Credit and Sector Awareness

Key Takeaways

➥ The Australian market was targeted for expansion during COVID due to its strong SME financing landscape.

➥ Deposits for acquisitions can vary significantly based on the business type and trading history.

➥ New investors may need to provide a higher deposit compared to those with established businesses.

➥ A solid business plan and financial model are crucial for securing financing.

➥ Interest rates and loan terms can vary widely based on market conditions and business performance.

➥ Refinancing options can improve cash flow and reduce interest rates over time.

Understanding personal credit scores is essential for first-time investors.

About Ciaran Burke

Ciarán Burke is the COO & Co-Founder of Swoop, a global SME funding marketplace that helps businesses discover debt, equity, and grant options using integrated business data.

He co-founded Swoop after a career at KPMG and building the creative network Hiive, and now leads the product & operations work that matches businesses with suitable finance solutions across multiple territories. Swoop’s platform has helped hundreds of thousands of businesses access funding and simplify options that traditional banks often miss, making it a powerful route for buyers who need acquisition capital. Ciarán frequently speaks about debt, equity, and grants to fund acquisitions in the UK, Australia, and the US.

Join Swoop Funding for free;

➥ https://swoopfunding.com/au/buying_online_businesses

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

With nearly three decades of inner work and growth behind him, Jaryd shares what he typically teaches behind closed doors to paid clients. Lately, one theme has been impossible to ignore: the profound impact relationships have on wealth, confidence, and expansion.

He explores how most people have three to five close relationships: family, partners, friends, or colleagues that unintentionally stifle their growth.

Check out the full episode to uncover the relationship dynamics that may be quietly holding you back—and learn how to break free from them.

Episode Highlights

02:44 The Impact of Relationships on Wealth

05:41 Family Dynamics and Financial Mindsets

07:54 Navigating Friendships and Financial Advice

10:44 The Role of Intimate Relationships in Personal Growth

21:34 The Impact of Relationships on Personal Growth

26:46 Navigating Friendships and Family Dynamics

32:20 Auditing Relationships for Abundance

37:29 Re-engineering Identity Through Social Circles

42:21 Actionable Steps for Relationship Management

Key Takeaways

➥ Spiritual practices contribute significantly to business success.

➥ Relationships can unconsciously stifle personal growth and abundance.

➥ Family conditioning often instills a scarcity mindset.

➥ It's crucial to audit your relationships regularly.

➥ Intimate partners can influence your ambition and success.

➥ Friendships should be evaluated based on their alignment with your goals.

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode, Jaryd Krause sits down with SaaS M&A professional Guillaume Lussato for a behind-the-scenes look at how successful software acquisitions actually happen. Guillaume breaks down his unconventional path from software sales at a cybersecurity company to sourcing and closing deals at Constellation Software, one of the most disciplined acquirers in the SaaS world.

Guillaume reveals why the best SaaS acquisitions aren’t rushed deals but relationships built over years. He shares how patience, credibility, and consistent founder outreach led to his first acquisition at SaaS Group—a low-profile digital calendar tool called DacBoard—and why targeting under-the-radar SaaS companies can unlock outsized opportunities.

The conversation dives deep into today’s hyper-competitive M&A environment, including how to stand out when every founder is being pitched. Guillaume unpacks the red flags most buyers miss, from risky customer concentration to weak net dollar retention, and explains SaaS Group’s clear acquisition framework—capital-efficient, product-led growth businesses with strong fundamentals.

The episode wraps with a powerful discussion on how to balance organic growth with acquisitions, avoid overextension, and make smarter strategic decisions when scaling a portfolio of software companies.

If you’re serious about SaaS acquisitions, this episode is a must-watch. Click through and watch the full video to learn exactly how Guillaume evaluates, sources, and scales SaaS businesses.

Episode Highlights

02:52 Transition from Sales to M&A Origination

05:52 The Art of Deal Sourcing

09:04 Evaluating Founders and Their Businesses

11:47 Understanding Acquisition Criteria

15:10 Growth Strategies: M&A vs. Organic Growth

18:00 Identifying Red Flags in Due Diligence

21:06 Navigating Operational Complexity

23:57 AI Risks and Opportunities in Software

27:06 Balancing Capital Allocation and Diversification

Key Takeaways

➥ You need to build relationships, build trust, build credibility.

➥ It can take a really long time to acquire a business.

➥ We try to identify red flags as early as possible.

➥ We don't manage our portfolio through spreadsheets; we're not finance people.

➥ Should we buy it? Why? For how much?

About Guillaume Lussato

Guillaume Lussato is a senior business development and M&A professional at saas.group, where he helps identify, acquire and scale profitable B2B SaaS companies. He hosts discussions on SaaS M&A, growth, and founder transitions and frequently speaks at industry events about how to grow without VC and what makes SaaS acquisitions succeed or fail.

Guillaume focuses on sourcing deals, operational playbooks for scaling post-acquisition, and practical insights that matter to anyone buying online businesses to replace income, scale a portfolio, or prepare for exits.

Connect with Guillaume Lussato

➥ https://www.linkedin.com/in/guillaumelussato/

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode, we sit down with Julien Jacques, who made the bold transition from building a real estate portfolio to acquiring online businesses—uncovering both the opportunities and the unexpected mistakes along the way. Julien shares his transparent journey, including his non-traditional Canadian financing strategies, the specific digital business models he targets, and the hard-earned “humble realist” lessons that came from both successful acquisitions and costly missteps.

Whether you’re managing rental properties, exploring your first acquisition, or curious about “online real estate,” this conversation delivers a grounded, experience-driven look at what it truly takes to scale in the digital business landscape.

Ready to rethink how you build wealth beyond physical assets?  Watch the full episode now!

Episode Highlights

10:51 Lessons Learned in Acquisition

13:28 The Importance of Relationships in Business

16:16 Structuring the Deal

21:01 Navigating Business Financing and Debt

22:11 The Dangers of Overdue Diligence

25:25 Making Decisions with Incomplete Information

29:45 Lessons from a Business Acquisition Failure

36:12 The Importance of Leadership and Networking

40:41 The Journey of an Entrepreneur: Risks and Rewards

Key Takeaways

➥ Real estate can provide passive income but requires management.

➥ Buying an existing business can be less risky than starting from scratch.

➥ Due diligence is important but can be misleading if overanalyzed.

➥ Networking is crucial for entrepreneurial success.

➥ Entrepreneurship requires resilience and adaptability.

About Julien Jacques

Julien Jacques is a former real-estate investor and entrepreneur who pivoted into buying online businesses after a year-and-a-half of searching across franchises, retail, and other opportunities.

He now owns Rocket Powered Sound, a digital products e-commerce business selling sample packs to music producers, and has firsthand experience in financing, acquiring, and scaling an online company in Canada. 

Julien’s practical transition from physical assets to “online real estate” gives him a unique perspective on acquisition due diligence, margin dynamics in digital products, and how to turn acquisition opportunities into reliable income streams.

Connect with Julien Jacques

➥ https://www.linkedin.com/in/juljacques/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Not the obvious red flags.
Not the spreadsheets.
But the quiet mistakes buyers make the moment they think they’ve already won.

In this episode, Jaryd Krause sits down with John Martinka (aka The Escape Artist), who’s spent 25+ years advising buyers and sellers across 150+ real acquisitions. No theory. Just what actually happens in deals.

You’ll hear why first-time buyers fall in love too fast, how stopping your search early weakens your position, and why relationships matter more than price once negotiations get serious. John also reveals how “great on paper” deals quietly turn into long-term stress, and what to do instead.

Plus, what happens after the deal closes: how one small shift helped a buyer grow a business by 75% in under a year, and why growth often fixes problems faster than perfection ever will.

If you’re buying a business (or even thinking about it), this episode will change how you see deals before it’s too late.

👉 Watch the full video now and get tips most buyers only learn the hard way.

Episode Highlights

02:45 – Buyer fever explained: why first-time buyers knowingly overpay—and how emotional attachment kills financing and post-close cash flow.

04:10 – Why stopping your search early weakens leverage, increases emotional risk, and makes buyers over-commit before a deal is real.

05:58 – A real $6M deal case study: how choosing the highest offer over the right buyer led to 12+ months of post-close disputes and massive stress costs.

10:05 – Why most deals do close after LOI—and the specific conditions that still quietly cause failures during diligence.

11:20 – Add-backs red flags: why too many adjustments signal risk, credibility issues, and potential tax exposure.

18:10 – Seller priorities revealed: why 90%+ of sellers care more about employee outcomes and legacy than price alone.

21:40 – Earn-outs unpacked: why earn-outs fail when used to justify overpricing—and when they actually make sense.

28:30 – How one compensation change drove 75% revenue growth in under 12 months after acquisition.

Key Takeaways

➥ Don’t fall in love with a business before due diligence. Emotional attachment (“buyer fever”) can lead to overpaying and unrealistic expectations.

➥ Keep your options open. Continuing your search until closing strengthens negotiating power and reduces risk.

➥ Choose the right buyer or seller over the highest price. Alignment of values, motivation, and vision prevents long-term disputes and stress.

➥ Customer concentration risk: Businesses with 2 customers generating ~60% of revenue are extremely vulnerable—loss of one client can collapse cash flow and valuation.

➥ Owner dependency is a hidden risk: Owners working 30–40+ hours per week without robust systems increase acquisition risk; businesses are more valuable when the owner can step away without disruption.

➥ Employee incentives drive growth. Strategic compensation and bonuses can unlock rapid revenue growth without heavy structural changes.

➥ Seller priorities often extend beyond money: Over 90% of sellers care about employee outcomes and business legacy as much—or more—than the final sale price.

About John Martinka

John Martinka, known as The Escape Artist®, is a veteran M&A advisor and business strategist. As Co-Founder and Managing Member of Nokomis Advisory Services and Martinka Consulting, he’s guided over 150 business buy-sell transactions and analyzed more than 1,000 companies. 

With more than 25 years of experience, John helps executives “escape” the corporate grind by buying businesses the right way, and he also coaches business owners to exit their companies with style, grace, and maximum value. He’s a prolific author (four business books) and speaker, passionate about reducing owner dependency, building systems, and setting up companies to scale or exit profitably.

Connect with John Martinka

➥ https://www.linkedin.com/in/johnmartinka/ 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this solo episode of the BOB podcast, Jaryd Krause goes off-script and gets brutally honest about the real reasons people struggle to acquire online businesses, and why these same patterns show up in money, business, and life.

This isn’t a tactical “how-to” episode.
It’s a mindset reset.

Jaryd breaks down the five biggest reasons people fail at buying a business, drawing from his own journey, his work with buyers around the world, and the patterns he sees repeatedly derail otherwise capable people.

You’ll learn:

• Why you don’t need to know how to run or buy a business before acquiring one
• How “good” advice becomes dangerous when you treat general guidance as personal truth
• Why most people are mentally unprepared for the acquisition process—even when they have the money
• How impatience and unrealistic timelines quietly sabotage deals
• The uncomfortable truth about why wanting a business isn’t enough—and when change only happens out of necessity

Jaryd also dives into cultural differences, ambition, pain as a driver of success, and why some people push through every obstacle while others stall indefinitely.

This episode is raw, reflective, and unapologetically real.

🎧 Listen in—and ask yourself whether you’re setting yourself up for success… or failure.

Episode Highlights

01:00 – Why most people unknowingly set themselves up for failure before they even start

06:55 – Myth-busting: Why you don’t need to know how to run or buy a business before acquiring one

10:45 – The danger of “bad” advice and why most guidance is general, not personal

13:55 – Why copying someone else’s timeline almost guarantees failure

18:30 – How unrealistic goals quietly destroy confidence and momentum

20:45 – The mental reality of buying a business and why most people aren’t prepared

24:30 – Patience vs. pressure: why counting inputs matters more than counting time

28:20 – Want vs. necessity: the single biggest reason people fail to follow through

32:40 – How pain, fear, and discomfort actually drive ambition and success

Key Takeaways

➥ You don’t need experience to get started. Most successful buyers had never run or bought a business before their first acquisition. Skills are built during the process—not before it.

➥ General advice becomes dangerous when taken as personal truth. What worked for someone else may not work for you due to differences in time, resources, credit, life stage, and risk tolerance.

➥ Unrealistic timelines create avoidable failure. Comparing your progress to others—or forcing artificial deadlines—leads to disappointment, self-doubt, and unnecessary quitting.

➥ Mental readiness matters more than capital. Buying a business requires patience, resilience, and the ability to handle rejection, uncertainty, and long stretches without visible progress.

➥ Preparation is psychological, not just financial. Due diligence, deal flow, and negotiations are mentally taxing—especially at lower price points where fewer systems and advisors exist.

➥ Stop measuring success by time. Measure inputs instead. Track actions like deals reviewed, conversations held, and due diligence completed. Progress compounds through consistent inputs, not arbitrary deadlines.

➥ Setting the bar too high too early damages confidence.  Low, achievable goals build momentum. Repeated “missed” goals—even small ones—erode belief and motivation over time.

➥ Wanting a better life isn’t enough—necessity creates action. True follow-through happens when change becomes non-negotiable, not optional.

➥ Pain and discomfort are powerful drivers, not problems. Ambition is often fueled by frustration, fear, or dissatisfaction. Learning to harness that energy is key to long-term success.

 Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

One deal?
A small portfolio?
Or a scalable acquisition machine?

In this episode, Jaryd Krause sits down with SBA Business Development Officer Glenn Giro to break down the real math behind buying businesses with SBA financing, and why there’s technically no cap on how many businesses you can acquire, as long as you understand the rules that actually stop most buyers.

They unpack how entrepreneurs are using up to 90% SBA financing, long 10-year terms, and no prepayment penalties to build portfolios most people assume are out of reach.

You’ll discover:

• How $100,000 in cash can unlock a $1M+ acquisition
• The $5M SBA cap per NAICS code and how it impacts serial buyers
• Why banks love SBA loans (and why that matters to you)
• The real fees lenders don’t explain upfront
• How cash flow and debt service coverage are actually calculated
• What changes when you go from your first deal to your second, third, or fifth
• When 100% financing is possible and when it’s not
• Why do some high-multiple digital businesses get rejected
• The timeline lenders expect before approving your next acquisition
  
  

If you’re serious about buying your first digital business or turning one deal into a portfolio of cash-flowing assets, this episode will completely reframe how you think about capital, leverage, and scale.

Watch the full video to see the numbers, strategies, and acquisition pathways most buyers never learn about.

Episode Highlights

02:55 – Why a “simple” 10% down payment can still kill your SBA deal if you don’t understand total project costs.

05:08 – The harsh truth: why $100K is often not enough to safely buy a $1M business.

10:52 – How SBA’s 75% loan guarantee unlocks 90% financing—and why banks are eager to lend.

12:57 – The hidden cost most buyers miss: $20K–$30K in SBA fees on a $1M acquisition.

15:16 – The real reason most buyers can’t buy a second business right after their first.

23:59 – The quiet rule that caps portfolios at $5M per NAICS code—and how it blocks long-term scaling.

Key Takeaways

➥ SBA financing allows buyers to acquire businesses with as little as 10% down, but cash reserves and liquidity matter more than purchase price alone.

➥ The SBA’s 75% government guarantee reduces bank risk and unlocks long-term, high-leverage financing for profitable online businesses.

➥ Seller financing can help bridge equity gaps, but new rules requiring 10-year standby make it rare in competitive acquisitions.

➥ Most buyers need 6–12 months of successful operations before qualifying for a second SBA-backed acquisition—proof of execution accelerates approvals.

➥ Each business must support its own debt service; strong cash flow in one acquisition won’t compensate for a weak second deal.

➥ NAICS code limits quietly shape acquisition strategy—buyers who plan ahead can scale portfolios faster and avoid unexpected financing caps.

About Glenn Giro

Glenn Giro is a seasoned SBA business development officer and acquisition financing expert who helps entrepreneurs buy and grow businesses using strategic SBA-backed loans. He hosts “SBA University,” a training series for business owners and aspiring acquirers, and regularly speaks about acquisition financing and business ownership strategies.

Connect with Glenn Giro

➥ https://www.linkedin.com/in/glenn-giro/

➥ https://www.youtube.com/@SBAUniversity  

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

They dive into what most first-time buyers totally miss—like how a “simple” service business pulling in $300–400k a year can still hit you with $10k in unexpected repairs, or how a business that seems hands-off can take up way more mental energy than you expect.

You’ll hear things like:

💡 Why lifestyle buyers often crash and how to avoid turning your dream into a money trap
⚠️ Even with a manager, some problems are just going to end up on your desk
🔧 How one dry-cleaning shop kept a family afloat but still drained the owner mentally
😬 What constant staff turnover really means—and the mindset that separates the quitters from the winners
🧠 Why corporate experience doesn’t prepare you for small-business chaos
📈 Why flipping businesses usually fails, but holding one for 5–6 years can pay off big
🤝 Why you need real business friends, not just LinkedIn highlight reels

David shares stories from owners who were totally blindsided by the day-to-day reality—turning neglected businesses into assets, and surviving the crazy, unexpected stuff along the way.

🎧 If you want the raw truth about buying a business—no fluff, just lessons you actually need—this episode’s for you.

Episode Highlights

07:07 – How overpaying and operational surprises can sink a business deal.

11:22 – The danger of buying based on emotion, not strategy.

15:30 – How “time on your side” strengthens your acquisition position.

20:15 – Fixing the “leaky bucket” of household finances before buying.

35:56 – Understanding your emotional drivers: lifestyle vs. self-actualization.

43:34 – Buying dreams vs. buying businesses: the B&B cautionary tale.

47:01 – Why running a business is harder than it looks: expectations vs. reality.

51:15 – The real value of small businesses is in long-term ownership, not flipping.

55:04 – Lessons from real owners: hiring struggles and the mindset of persistence.

Key Takeaways

➥ Know your motivation. Buying a business without understanding your emotional drivers — lifestyle, status, or security — can lead to overpaying or making misaligned choices.

➥ Cashflow and leverage are critical. Overpaying or using high leverage without accounting for operational costs and capital expenditure can sink even profitable businesses.

➥ Time is your ally. Build financial strength and patience first. A strong savings habit and a clear understanding of deals over time make you a stronger, less impulsive buyer.

➥ Due diligence saves you. Verify revenue, costs, and seller claims. Skipping checks or relying on emotion leads to costly mistakes.

➥ Lifestyle vs. business reality. Owning a business provides freedom and income, but it always carries operational burdens. Expect hands-on involvement, even with managers in place.

➥ Start with experience. Before buying a business in a new industry, work in it part-time. Real exposure prevents costly surprises.

➥ Value is in ownership, not flipping. Profit comes from running a business over years, not quick resale. Systems, marketing, and management improve long-term returns.

➥ Network with real business owners. Observing how experienced owners handle hiring, challenges, and growth teaches lessons no podcast or post can convey.

About David Barnett

David C. Barnett is a seasoned business broker, advisor, and educator who has helped aspiring entrepreneurs buy and sell small-to mid-sized businesses since 2009. He is the founder of the Business Buyer Advantage program—a comprehensive training system that guides buyers through finding, analysing, offering on, financing, and integrating a business. David’s background includes business valuation, deal structuring, and a passion for helping people escape the 9-to-5 by owning cash-flowing businesses.

Connect with David Barnett

➥ https://www.businessbuyeradvantage.com

➥ https://www.linkedin.com/in/davidbarnettmoncton 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode of the BOB Podcast, Jaryd Krause sits down with Yury Byalik, a seasoned growth marketer, acquisitions strategist, and digital-business investor who has spent over 15 years building, buying, and scaling profitable online companies. Currently serving as Head of Strategy & Acquisitions at Onfolio Holdings, Yury has mastered the art of spotting opportunities, structuring deals, and growing digital businesses into high-performing assets.

But here’s the thing: acquisitions aren’t as simple as signing papers. Mistakes happen—and they can cost you time, money, and growth. Yury shares exactly what to avoid and what strategies actually work.

In this episode, you’ll learn:
💡 How Yury evaluates a digital business before buying
🔧 The most common mistakes first-time acquirers make—and how to sidestep them
📈 The growth strategies that turn a purchased business into a profitable, scalable asset
🧠 The mindset needed to build a successful acquisition portfolio
🤝 Practical tips on integration, operations, and making your acquisitions work together

Whether you’re considering your first digital business purchase or looking to scale an existing portfolio, this episode is packed with actionable insights and real-world lessons from someone who’s actually done it—15 times over.

🎧 Plug in and get ready to avoid costly mistakes while accelerating your acquisition journey.

Episode Highlights

07:07 – Why a strong team and legal safeguards can make or break a deal.

09:06 – A shocking story of hidden fraud and non-disclosure.

15:05 – Roll-Up vs. Independent Growth: Yuri shares his selective approach to merging acquisitions

19:00 – Why high‑volume acquisition strategies (e.g., Amazon roll‑ups) often fail.

20:54 – Why waiting 1–3 months can save millions before scaling.

29:41 – How AI commoditization is reshaping valuations across industries.

Key Takeaways

➥ Due diligence is non‑negotiable. Many sellers omit or misrepresent critical information (clients leaving, illegal kickbacks, contract terms). Without a strong legal and analysis team, even “profitable” businesses can become liabilities post-acquisition.

➥ Diversification of traffic and revenue matters. Businesses dependent on a single channel (SEO, ads, Amazon, Google Adsense) are exposed to high risk — a single algorithm or platform change can destroy value.

➥ AI has fundamentally changed valuations. With AI tools reducing the uniqueness of content, and enabling rapid replication of SaaS ideas, multiples on content- or software-based businesses have dropped significantly. That means both risk and opportunity for buyers.

➥ Patience and strategic focus beat volume-based roll-ups. Instead of snapping up every deal, it’s smarter to take time, understand what works inside the business, and selectively scale what’s already strong — especially if you plan to operate (not flip) long-term.

➥ Passion and niche alignment improve acquisition success. Businesses tied to hobbies, communities, or long-term interests tend to perform better when buyers are genuinely invested, because passion translates to better stewardship and resilience through ups and downs.

➥ In attractive niches, speed is everything. When a good business hits the market (clean model, diversified traffic, good margins), multiple buyers are often ready — meaning you need clear, fast decision-making if you want to win the deal.

About Yury Byalik

Yury Byalik is a seasoned growth marketer, acquisitions strategist, and digital-business investor with over 15 years of experience building, buying, and scaling profitable online businesses. Currently, he serves as Head of Strategy & Acquisitions at Onfolio Holdings, a public company that acquires and operates a diversified portfolio of digital assets. Before that, Yury worked across digital marketing, SEO, and business law, giving him a unique blend of operational, legal, and deal-sourcing expertise. He is a recognized speaker and contributor on topics such as deal sourcing, acquisition evaluation, and value creation in the online business space.

Connect with Yury Byalik

➥ https://levelfield.io/

➥https://bridgethegap.ai/

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Nick brings more than a decade of Private Equity experience to the conversation. Throughout his career, he has completed over 50 acquisitions, sold 26 businesses, created over $5 billion in value, and played key roles in three exits exceeding $1 billion each. His expertise offers a rare, behind-the-scenes look at what it truly takes to buy, integrate, grow, and exit companies at scale.

In this episode, listeners will learn:

💡 The criteria first-time acquirers should focus on

🔧 Nick’s Squared Management System—the four pillars and 40 essential elements that create a solid management foundation

🤝 How to merge two businesses, how long integration takes, and the steps involved in acquiring for growth

🧠 The mindset required for those building a portfolio through acquisition

📈 The characteristics of successful portfolio builders, including why “boring” businesses often become the most profitable

For anyone considering growth through acquisition or curious about how seasoned investors strategically scale companies, this episode provides the insights and frameworks needed to navigate the world of M&A with confidence.

Episode Highlights

02:10 –  Why Founders Struggle?

04:41 – Strategic vs. Financial Value: Understanding "The Buyer’s Math" 

07:00 – Build Your Business To Be Sellable

09:21 – What PE Firms Do Differently: Discipline, Detachment & Focus

Key Takeaways

➥ Most founders misunderstand what truly drives business value. They tend to focus on revenue or profit, but in reality, those are only about 40% of the valuation—60% comes from operational, strategic, and structural factors that founders often overlook.

➥ Sophisticated buyers play a different game. Private equity firms and large acquirers buy and sell companies constantly. They know the rules, the metrics, and the process far better than most founders who are going through a once-in-a-lifetime sale.

➥ Value is based on the buyer’s math, not the seller’s. Strategic buyers care about customer bases, distribution, systems, capability, geographies, and integration potential, not just financial performance. Founders must understand what their business is worth to the buyer.

➥ A business should always be built to be sellable—even if you never sell. A well-built business creates freedom, independence, and optionality. When a sale opportunity comes, you’ll be in the best position to maximize value.

➥ Private equity excels because of emotional detachment and absolute focus. PE firms operate with military-level discipline—no emotional decision-making, full clarity on end goals, and a strict focus on executing a plan that increases value fast. This contrasts with founders who are often emotionally attached to their business.

About Nick Bradley

Nick Bradley is a world-renowned author, speaker, and business growth expert who works with entrepreneurs, business leaders, and investors to build, scale, and sell high-value companies.

After spending a decade in Private Equity, Nick has seen the ups and downs of business growth and the key challenges that impact business performance. During that time, he completed over 50 acquisitions, sold 26 businesses, and created over $5bn in value. He has personally been involved in 3x exits valued at over $1bn each.

Nick believes that scaling and eventually selling your business isn’t a “game of chance”. With guidance and support, your business can navigate the complexities of markets, scale efficiently, attain business goals that match your vision, and achieve an outstanding exit that reflects the hard work you have invested in your journey.

He also believes in leveling the playing field with sophisticated buyers, such as Private Equity, equipping business owners with the strategies and tools to compete in the fierce world of M&A … and win the game.

Connect with Nick Bradley

➥Nick’s LinkedIn: linkedin.com/in/realnickbradley

➥ Exit Your Business For Millions - Download This Guide: https://go.highvalueexit.com/opt-in

 Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

The real barrier isn’t the price—it’s everything you don’t see coming before you even sign.

In this solo episode, Jaryd Krause pulls back the curtain on the part of buying a 7-figure business that almost nobody talks about—the real costs, the real timelines, the real competition, and the parts of the process that can quietly wreck your deal long before you ever get to the closing table.

Most people assume a $1M acquisition is simple math:
Find the business, put down the deposit, sign some papers, done.

But behind every one of those deals are fees, structures, advisors, lenders, deadlines, and expectations that—if you’re not prepared—will eat your budget and your sanity alive.

Here’s what Jaryd gets into:

📌 The actual line-item expenses of buying a 7-figure business (legal, advisors, due diligence,  escrow, lender fees—yes, all of it)

📌Why doing a smaller deal doesn’t necessarily make anything easier and why some “cheap” deals cost more in mistakes

📌How the right deal structure can turn upfront costs into credits that reduce what you owe at closing

📌 The role of buyer-side advisors —what they charge, what they’re worth, and when you shouldn’t hire one

📌 The hidden criteria lenders use to judge your deal that most buyers don’t even know they’re being evaluated on

📌 Why timelines are never linear and competition is always sharper at the top

📌 The mindset traps that sabotage buyers and how patience becomes the most profitable strategy you have

Jaryd doesn’t dress it up.

He walks you through the real picture—what it costs, what’s negotiable, what’s risky, and what will give you an edge when everyone else is rushing and guessing.

If you’ve ever wondered whether you can actually afford a million-dollar acquisition, consider this your roadmap—and your reality check.

🎧 Plug in. This one will change the way you look at buying a business.

Episode Highlights

01:15 – Differences between sub-$500K deals vs seven-figure acquisitions

02:24 – Key costs when buying a seven-figure business

04:52 – Why do you need a specialized M&A lawyer?

07:13 – How to structure legal packages for letters of intent, asset purchase agreements, and contract due diligence

16:56 – Why larger businesses can be easier to acquire despite higher costs, and how cash flow impacts returns

19:22 – How long it can take to close a seven-figure business deal and factors affecting timing

21:40 – Cash vs. financed deals: the impact on negotiation power and deal structure

23:55 – Setting realistic expectations and why compounding small wins builds confidence in acquisitions

26:17 –  Why do you need to work with experts?

Key Takeaways

➥ Legal fees for M&A lawyers usually run 1–2% of the deal, and using an experienced online business acquisition lawyer is essential.

➥ Finance broker fees range from $5K–$10K, with SBA or lender fees around 3.5–3.75% of the financed amount, often rolled into the loan.

➥ Buyer-side advisors (3–8% of deal size) can review due diligence, advise on deal structure, negotiate, and sometimes source pre-vetted businesses.

➥ Due diligence packages ($5K–$40K) and escrow (~1% of acquisition) are key costs, but many upfront fees can be credited toward your deposit.

➥ With smart planning, many upfront costs—legal, advisor, and broker fees—can be credited toward your deposit, allowing acquisition with just 10% cash down.

➥ The larger the business, the more leverage you have, and the more stable the cash flow. Entry costs scale, but ROI potential often increases with size.

➥ Acquisition timelines vary widely—sometimes months, years—depending on market availability, acquisition criteria, and competition. Patience is key.

➥ Set realistic expectations. Overly ambitious goals or standards can harm mindset and decision-making. Compounding small wins builds confidence and sustainable success.

 Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAm

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode, Jaryd Krause chats with Ray Drew—aka SBA Ray—host of The Art of SBA Lending, the #1 podcast that pulls back the curtain on how SBA loans really work.

Ray is the Managing Director at Truliant Federal Credit Union, a deal closer with hundreds of successful SBA-financed businesses under his belt, the man behind millions in SBA-backed deals, and the architect of SBA success stories nationwide.

He’s seen everything—the smooth wins, the total nightmares, and the deals that fell apart days before closing.

Most people think an SBA loan is simple: apply, get approved, buy the business, boom—you’re a CEO. 

But the truth? 

There are traps hidden in plain sight. And missing just one could cost you the deal—or tens of thousands in wasted time and fees.

Here’s what Ray and Jaryd dive into:

🔥 The hidden misconceptions that trip up first-time buyers (even the smart ones)
🔥 Why your “perfect” deal structure could actually kill your loan approval
🔥 The truth about interest rates, balloon payments, and seller financing nobody tells you
🔥 What really happens behind the scenes when lenders assess your deal
🔥 The surprising reason your loan might get rejected even if you’re qualified
🔥 How long does the process really take—and what delays can quietly blow up your timeline
🔥 Why the right M&A attorney can save your deal when everything’s on the line

Ray doesn’t sugarcoat it—he breaks down exactly what’s going wrong in the SBA space and what you need to know before you sign anything.

If you’ve ever dreamed of acquiring an online business but didn’t know how to fund it, this is your reality check and your roadmap.

Because when it comes to SBA lending, it’s not just about money… It’s about knowing the game before you play it.

🎧 Grab your headphones. This one could save your next deal.

Episode Highlights

01:12 – What SBA lending is and why it’s a game-changer for business buyers

06:40 – Why buying a business often beats starting from scratch

09:24 – The most common misconceptions about SBA loans

12:10 – Key factors lenders look for before approving a deal

15:32 – The #1 mistake buyers make during the SBA loan process

18:46 – How to choose the right lender and build a strong relationship

21:55 – Real stories from hundreds of SBA-financed deals—the smooth, the messy, and the ones that fell apart

25:08 – How does the deal structure and negotiation impact loan approval

28:26 – Why preparation is the real secret to fast, successful closings

31:47 – Ray’s process for evaluating if a business is truly financeable

34:15 – Lessons from deals that went wrong—and how to avoid the same pitfalls

37:28 – What every buyer should do 6–12 months before applying for an SBA loan

39:52 – Ray’s best advice for entrepreneurs who want to acquire a business in 2025

Key Takeaways

➥ SBA financing is one of the most powerful yet misunderstood tools for buying a business—it lets entrepreneurs acquire profitable companies with as little as 10% down.

➥ Preparation is everything. Clean financials, accurate tax returns, and a solid business plan can drastically increase your chances of getting approved.

➥ The right lender matters more than most realize. Experienced SBA lenders can structure deals creatively, solve problems quickly, and close with confidence.

➥ Not all deals are created equal—lenders look for stable cash flow, strong management transitions, and businesses with proven profitability.

➥ Expect surprises. Even well-structured deals can fall apart near closing, so patience, flexibility, and expert guidance are essential.

➥ Buying a business with SBA financing isn’t just about getting a loan—it’s about acquiring a long-term wealth vehicle that can transform your financial future.

➥ Execution beats theory. Ray’s track record proves that the best buyers are those who take action, learn from each deal, and build relationships with trusted lenders.

About Ray Drew

Ray Drew is the SBA Managing Director at Truliant Federal Credit Union, where he helps entrepreneurs buy businesses through SBA financing. With over a decade in the industry, Ray has closed hundreds of deals and is widely regarded as one of the leading voices in SBA lending today. He is also the host of the #1 podcast in the SBA lending industry, The Art of SBA Lending.

Connect with Ray Drew

➥ www.sbaray.com

➥ https://www.youtube.com/@SBA_Ray

 Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

In this episode, Jaryd Krause sits down with Andri Sadlik, a pro at scaling SaaS, AI, and e-commerce businesses.

Andri launched his first business and exited successfully. After that, he scaled multiple Amazon FBA brands from $100K a year up to $1M, and finally over $10M.

No gimmicks, no luck—just carefully built systems, a strategy that makes sense, and teams that execute like clockwork.

He’s also the co-founder of ProductPinion, a SaaS company he’s planning to exit, and has been featured in top media outlets for his expertise in scaling businesses.

In this conversation, you’ll hear how he:

🚀 Built and sold his first business—without repeating rookie mistakes

🚀 Survived a broker nightmare—and came out ahead

🚀 Took Amazon brands from $100K → $1M → $10M+

🚀 Created influencer programs that generate real ROI

🚀 Scales multiple businesses by connecting teams, systems, and plans

Andri shares the challenges, the wins, and the step-by-step strategies that helped him grow an impressive portfolio of businesses. If you want actionable insights on scaling, selling, or acquiring e-commerce businesses, this conversation is packed with value.

Tune in and learn how to take your business from 0 to 8-figures—and avoid the mistakes that can cost you big.

Episode Highlights

01:04 – How Andri sold his 3-year-old Amazon FBA business in 2020

03:07 – How to vet brokers carefully

07:30 – How to prep for business exit prep

12:58 – The post-acquisition success story

16:41 – How to bring new customers with minimal effort while complementing existing PPC spend.

23:06 – Secret hack for driving real conversions.

27:36 – Why experience matters

Key Takeaways

➥ Selling a business isn’t just about the exit—it’s about preparation. Optimizing operations, cleaning up books, and systemizing processes can dramatically increase value before you sell.

➥ Choosing the right broker is critical. Some may prioritize buyers over sellers, so triple-check their process and talk to previous clients to avoid surprises.

➥ Price smart: list slightly higher than you expect to sell. Buyers usually negotiate down, and a higher starting point protects your upside.

➥ Post-acquisition growth thrives on systems and expertise. Optimizing listings, ads, inventory, and operations can double revenue—even for a brand bought for “super small” amounts.

➥ Recurring purchase models are gold. Consumable products, repeat buyers, and brand loyalty can accelerate growth faster than flashy campaigns.

➥ Leveraging influencer programs strategically—segmenting creators, VIPs, and deal groups—can drive 11%+ of sales without heavy spend.

➥ Continuous experimentation, collaboration, and smart use of customer feedback unlock unexpected growth. Even small tweaks to processes or partnerships can massively scale results.

About Andri Sadlak

Andri Sadlak is the Head of Product & Strategy leader with a track record of building and scaling SaaS, AI, and e-commerce businesses. Scaled  8-figure portfolio, co-founded a Saas company called ProductPinion, and has featured in many media publications talking about scaling online businesses..

Connect with Andri Sadlak

➥ https://www.linkedin.com/in/sadlak/

 Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

That’s exactly what Chan Yuenenyi did.

In this episode, Jaryd Krause chats with the founder and CEO of EssayGrader AI—the world’s leading AI grading platform trusted by over 100,000 educators.

When Chan bought the business, it was generating only $5,000 per month. Fast-forward less than a year later, and he’d scaled it to $80,000/month, hitting $1M in annual recurring revenue.

But here’s the twist: Chan didn’t chase shiny tactics or massive ad budgets.
He used precision. Systems. Deep understanding of what users actually need.

Before founding EssayGrader AI, Chan managed a billion-dollar product line at OpenText. So, he knew one thing most first-time buyers miss—buying a business is easy. Growing one takes vision.

In this conversation, you’ll discover how he:

🔥 Spots red flags before closing a deal
🔥 Turns customer feedback into a growth engine
🔥 Shifted from “operator” to “owner”
🔥 Discovered the single most powerful strategy behind his $5K → $80K leap
🔥 Built what he calls “inside-out growth”—and why it changes everything

This isn’t just a story about scaling. It’s about clarity, focus, and designing a business that grows because it serves people better.

If you’re looking to buy your first SaaS—or scale the one you already own—don’t miss this one.
It’s packed with real lessons from someone who’s actually done it.

Episode Highlights

08:08 – Chan reveals his process of evaluating 25–30 businesses over 90 days, learning to identify patterns, red flags, and what truly matters when choosing the right acquisition.

13:56 – Why product-market fit and traction matter more than polished features or perfect design when evaluating early-stage SaaS.

15:51 – Chan breaks down the valuation and deal structure—he bought SAGrader.ai for $125K in cash at a 2x revenue multiple.

19:46 – Red flags to watch for when buying a business—no traction, unclear customer base, lack of competitors, or overbuilt products.

27:42 – How involving users in building new features turned customers into loyal advocates and multiplied sales through word of mouth.

28:27 – The impressive growth story—from $5K to $80K MRR in a year—by focusing on fundamentals and customer insights over flashy marketing tactics.

30:34 – Why execution beats information overload: Chan’s advice to stop chasing every online guru and start acting on core business principles.

Key Takeaways

➥ Acquiring an existing SaaS business offers a faster, lower-risk entry into entrepreneurship compared to starting from scratch, letting you focus on growth instead of setup.

➥ Evaluating dozens of deals before buying helps refine your investment instincts—each review teaches you how to spot red flags, assess traction, and recognize scalable opportunities.

➥ Product-market fit is the single most important factor in acquisition success; without genuine demand and active users, no amount of marketing can sustain growth.

➥ Direct customer communication—through live chat, feedback loops, or support channels—unlocks powerful insights that shape product improvements and retention.

➥ Growth doesn’t come from adding complexity but from deeply understanding your users and iterating based on their real-world needs.

➥ Cash deals can streamline acquisitions and build seller trust, though they require strong conviction in your due diligence and vision for growth.

➥ Listening, testing, and improving continuously can turn a modest $5K MRR business into an $80K MRR success—proof that fundamentals and focus outperform flashy tactics.

About Chanakya Yerneni

Chan Yerneni who is Founder & CEO of EssayGrader AI, the #1 AI grading platform trusted by 100,000+ educators to save 10+ hours every month grading student submissions. Former Senior Product Marketing Manager at OpenText ($1B+ product).

Connect with Chanakya Yerneni

➥ https://www.essaygrader.ai/

➥ https://www.linkedin.com/in/chanakya-yerneni-338869378/ 

 Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

➥ Hostinger (Website Hosting) - https://bit.ly/3HUqW0s

➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM

➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

Antoine shares his candid reflections on navigating acquisitions, from spotting undervalued opportunities to balancing multiple ventures and knowing when it’s time to sell. They explore how trust and transparency form the foundation of any successful deal, why valuation isn’t just about numbers, and how emotional awareness can be the difference between a smooth exit and a painful one.

Through Antoine’s firsthand experiences, this conversation provides a roadmap for entrepreneurs looking to grow not just through innovation but through strategic acquisition and authentic relationships.

Together, they explore:

✔️ Why buying an existing business can be less risky than starting from scratch
✔️ The emotional and relational side of business acquisitions most founders overlook
✔️ How to balance multiple ventures without losing clarity or momentum
✔️ The right way to approach valuation and negotiation in SaaS deals
✔️ Lessons learned from multiple exits—and why selling doesn’t always mean letting go

Whether you’re an aspiring acquirer, a seasoned founder, or somewhere in between, this episode will challenge how you think about growth, exits, and the role of trust in entrepreneurship.

🎧 Tune in to discover how Antoine Minoux built and exited multiple SaaS businesses by combining strategic thinking with human-centered design—and how you can too.

Episode Highlights

02:50 – Why acquisition can outperform starting from scratch: understanding risk reduction and leveraging proven systems for faster growth.

08:24 – Lessons from multiple exits: what Antoine learned about timing, valuation, and emotional readiness.

16:23 – Knowing when to sell: the strategic and personal factors that influence exit decisions.

19:26 – Balancing multiple ventures: how to manage creative energy, focus, and burnout when running several businesses.

22:02 – Smart valuation strategies: combining upfront cash flow with future performance for sustainable exits.

24:44 – Evolving as an entrepreneur: how experience shapes acquisition instincts and strategic clarity.

29:52 – Redefining the meaning of an exit: why selling a business doesn’t always mean walking away from your vision.

Key Takeaways

➥ Buying an existing business often offers a safer and faster path to success than starting from zero.

➥ Trust and transparency aren’t just values—they’re strategic advantages in high-stakes transactions.

➥ Emotional awareness is critical during acquisitions and exits; ego-driven decisions can destroy deals.

➥ A great valuation balances immediate returns with long-term performance and relationships.

➥ Experience in your industry dramatically improves your ability to identify and grow profitable opportunities.

➥ Exiting a business can be a transformation, not a goodbye—many founders stay involved in new, more strategic ways.

➥ Growth through acquisition requires both strategic thinking and emotional intelligence—one without the other leads to imbalance.

About Antoine Minoux

Antoine Minoux is a Principal Product Designer at Yelp and an Indiepreneur currently living and working in Hamburg. He successfully founded, designed, grew, and sold multiple bootstrapped SaaS companies like Voilanorbert.com and Improvmx.com. He is now working on Fernand, the ultimate custom messaging tool for modern SaaS.

Connect with Antoine Minoux

➥ https://www.linkedin.com/in/antoineminoux/ 

➥ ww.getfernand.com - Link to Ep 339 with Matthew Tse, the Acquirer of ImproxMX

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

➥ Cloud Ways (Website Hosting) - https://bit.ly/40tjyjG

➥ SEM Rush (SEO tool) - https://bit.ly/3lINGaV

➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

From their first steps into e-commerce to managing complex acquisitions, Brian and John share how having the right mentor, team, and financial structure can make or break a deal. They pull back the curtain on what it really takes to grow an online business—revealing how patience, education, and teamwork pave the way for long-term success in a fast-changing digital economy.

Together, they unpack:

✔️ The role of mentorship in accelerating business growth and confidence
✔️ How to build diverse revenue streams that stabilize your portfolio
✔️ Financial planning fundamentals every buyer needs before acquisition
✔️ Why a strong team and legal support system are non-negotiable
✔️ The mindset shift from “buying a job” to “owning a business”
✔️ How customer feedback fuels innovation and operational improvement
✔️ Building systems that scale—and keep your business sustainable

Through candid reflections and hard-won lessons, Brian and John offer a blueprint for entrepreneurs who want to expand strategically while avoiding the burnout and chaos that often follow growth. Whether you’re an aspiring buyer or already running multiple online ventures, this episode will equip you with the mindset and structure to scale with confidence.

🎧 Tune in to learn how to design your business for growth, master your numbers, and build a team that frees you to focus on your next big move.

Episode Highlights

05:31 – Navigating acquisitions: lessons learned from evaluating, negotiating, and structuring successful deals.

08:26 – Building your inner circle: why legal, financial, and operational support are essential for scaling.

11:23 – Overcoming acquisition hurdles: managing uncertainty, setbacks, and the emotional rollercoaster of business buying.

22:39 – Planning ahead: aligning goals, systems, and strategy for sustainable expansion.

34:30 – Systems thinking: creating repeatable processes that build resilience and scalability.

35:19 – The power of partnership: how trust and complementary skills strengthen business outcomes.

38:25 – Hard-won wisdom: advice for first-time buyers on patience, preparation, and perspective.

41:00 – Education as an edge: how continuous learning fuels smarter investments and growth.

48:12 – The road ahead: building a sustainable, diversified business portfolio with long-term impact.

Key Takeaways

➥ Mentorship accelerates mastery. The right guidance can save years of trial and error.

➥ Understand your numbers. Financial clarity is the foundation of every successful acquisition.

➥ Build systems, not chaos. A strong operational structure allows growth without burnout.

➥ Customer feedback is your compass. Listening to your audience drives smarter innovation.

➥ Teamwork scales success. A capable team frees you from the daily grind and fuels sustainable growth.

➥ Stay curious. A beginner’s mindset keeps you adaptable in an evolving e-commerce landscape.

About John & Brian

John & Brian are BuyingOnlineBusinesses.com graduates, online business owners, and acquisition entrepreneurs. They have a high 7-figure ecommerce business and also acquired another 7-figure online business with Jaryd Krause as their M&A advisor to add to their portfolio of businesses. They are achieving great things and have even bigger goals that they are well on their way to achieving through business acquisition and growth. 

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u

➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM

➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

With experience across investment banking, corporate development, and private equity, Matthew knows what it takes to turn good businesses into great ones. He’s the mind behind the Square Management System, a framework built to help entrepreneurs align culture, structure, and strategy so growth happens seamlessly—not chaotically.

In this episode, you’ll learn:

✔️ Why understanding customer lifetime value is more important than acquisition cost
✔️ How pricing and packaging decisions influence business scalability
✔️ What makes the Square Management System a powerful tool for growth
✔️ The critical role of cultural fit in M&A integration
✔️ How to manage different revenue types and their impact on valuation
✔️ Why boring businesses often yield the best returns
✔️ The common integration challenges—and how to plan for them
✔️ What successful portfolio builders do differently from the rest

Jaryd and Matthew break down the real drivers of business success, from understanding customer lifetime value and pricing strategy to building systems that make integration smooth and scalable. Whether you’re eyeing your first acquisition or managing a growing portfolio, this episode shows you how to scale smarter, not harder.

🎧 Tune in to learn how to build, buy, and scale businesses the smart way—through systems, strategy, and structure.

Episode Highlights

09:17 – The Square Management System: Matthew’s proven framework for scaling businesses through structure, culture, and alignment.

14:10 – Lessons from investment banking: insights on spotting hidden value and capturing upside in every deal.

18:52 – Smarter deal structures: balancing growth potential with risk mitigation to protect your investment.

21:15 – The magic of recurring revenue: how predictable income streams boost valuation and stability.

23:38 – The art of integration: navigating the human and operational challenges that make or break acquisitions.

29:05 – Culture as the glue: why cultural fit is essential for seamless post-acquisition success.

33:37 – Scaling through systems: how effective management systems create control, consistency, and scalability.

37:38 – Portfolio builders’ mindset: the habits and principles of investors who consistently grow thriving portfolios.

Key Takeaways

➥ Growth by acquisition starts with deep customer and market understanding, not spreadsheets.

➥ Retention drives profitability—a loyal customer base is the real engine of value.

➥ A clear pricing strategy can multiply growth potential without new customers.

➥ Culture eats strategy for breakfast—successful integrations start with people, not processes.

➥ Investment banking experience gives you the lens to structure smarter, safer deals.

➥ Different revenue types (recurring, transactional, hybrid) shape how your business is valued and scaled.

➥ The Square Management System offers a blueprint for scaling operations across multiple brands.

About Matt Person

Matt Person is a seasoned corporate strategist, investor, and M&A expert with over 25 years of experience helping companies build and capture enterprise value. Currently SVP of Corporate Development at Quickbase (a Vista Equity-backed SaaS platform), he also founded Town Square Advisors, where he created the Square Management System: a proprietary framework that drives high performance through alignment, culture, and organizational design built on constrained independence. 

Prior, he led global corporate development, deal execution, and growth strategy for enterprise SaaS firms like IDG and Green Street Advisors, as well as worked in investment banking and strategy consulting. Matt combines deep technical and financial expertise with operational leadership and a passion for building winning teams. On this episode of the Buying Online Businesses Podcast, he shares how you can not only buy and scale online businesses, but also structure them and your own mindset to replace your income and craft a life of freedom.

Connect with Matt Person 

➥ www.townsquare-advisors.com

Resource Links

➥ Connect with Jaryd here - https://www.linkedin.com/in/jarydkrause

➥ Sell your business to us here - https://buyingonlinebusinesses.com/sell-your-business/

➥ Buying Online Businesses Website - https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework - https://buyingonlinebusinesses.com/freeresources/

➥ Google Ads Service - https://buyingonlinebusinesses.com/ads-services/

➥ Site Ground (Website Hosting) - https://bit.ly/3JBEC1u

➥ Surfer SEO (SEO tool for content writing) - https://bit.ly/3WWMKjM

➥ Ezoic (Ad Network) - https://bit.ly/3NuVR5P

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers - https://bit.ly/3RtyMkE

➥ Flippa - https://bit.ly/3wGa8r5

➥ Motion Invest - https://bit.ly/3YmJAmO

➥ Investors Club - https://bit.ly/3ZpgioR

*This post may contain affiliate links, so we may earn a small commission when you make a purchase through links on our site/posts at no additional cost to you.

See omnystudio.com/listener for privacy information.

A former Israeli Special Forces operative, the youngest federal agent and air marshal in Israel’s history, and a Brazilian Jiu-Jitsu black belt, Itamar has coached hundreds of six to nine-figure entrepreneurs, executives, and elite athletes to break through mental barriers, eliminate self-sabotage, and operate at their peak under pressure. His clients have exited companies for nine figures, raised hundreds of millions in capital, and ranked among the top performers in their industries.

Together, Jaryd and Itamar dive deep into the psychology of performance, exploring:

✔️ The three biggest bottlenecks holding entrepreneurs back from success
✔️ How to identify the most direct path to your goals—and stay on it
✔️ The top three performance traps that stop business owners from scaling
✔️ Why even experienced buyers struggle after acquisition—and how to fix it

Through real-world examples from Itamar’s military and coaching experience, you’ll discover how to spot the patterns of self-sabotage that quietly derail deals, limit growth, and block financial freedom.

Whether you’re preparing to buy your first online business, scale an existing one, or build a portfolio, this episode reveals the mindset frameworks that separate high performers from those stuck in perpetual struggle.

🎧 Tune in to learn how to master your mental game, eliminate hidden obstacles, and finally unlock the success that’s been just one step away.

Episode Highlights

02:41 – The most direct path to success: identifying high-leverage actions instead of chasing complexity or distractions.

08:12 – Common success killers: self-sabotage, procrastination, and the subtle traps that derail high performers.

13:51 – The fear of not being ready: unpacking the mindset that stops many entrepreneurs from taking bold action.

24:26 – Balancing emotional comfort with the uncertainty of growth and why detachment is a key entrepreneurial skill.

30:08 – Performance traps: the myth of “working harder” and how the go-harder mentality leads to burnout.

37:41 – Strategic approaches to business growth: recognizing emotional bottlenecks that limit scale. 

48:08 – The mindset mastery framework: practical tools to overcome internal blocks and build resilience.

Key Takeaways

➥ The biggest limiting belief in business is the “I’ll be ready once…” mindset. You already have what you need to take the next step.

➥ Identify your most direct path to success by asking, “What would someone else—less skilled or experienced—need to do to achieve this goal?”

➥ Emotional detachment is a superpower; it helps you make clear decisions without fear or bias clouding judgment.

➥ Seeking approval is deeply human, but when unmanaged, it leads to poor negotiations, people-pleasing, and self-sabotage.

➥ Performance traps like “just push harder” often backfire. Sustainable success requires rest, recovery, and self-awareness.

➥ Self-sabotage isn’t a flaw—it’s a signal. The key is understanding which mental model or emotional loop is driving your decisions.

About Itimar Marani

Itamar Marani Itamar Marani is regarded as one of the top performance and mindset coaches in the world. He’s a former Israeli Special Forces operative, the youngest federal agent and air marshal in Israel’s history, a Brazilian Jiu-Jitsu black belt who’s competed at a world-class level, and a mentee of the Mossad’s chief psychologist. 

He has since coached hundreds of 6–9 figure entrepreneurs, executives, traders, and pro athletes to break through performance plateaus, eliminate mental drag, and operate at their highest level under pressure. His clients have exited companies for nine figures, raised hundreds of millions of dollars, and entered top ten rankings in the world, among other results.

Connect with Itamar Marani 

➥ https://itamarmarani.com

➥ https://itamarmarani.com/book

➥https://buyingonlinebusinesses.com/ep-240-how-emotional-intelligence-is-your-secret-weapon-to-unlocking-your-greatest-potential-in-business-with-itamar-marani/

 Resource Links

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