Buying a Business While Working Full-Time & Raising 7 Kids (No Margin for Error) with Michael Simpson

What does it actually look like to buy a business with zero margin for error?

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

 

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