The SMB Deal Hunter Podcast

Join me as I interview Gretchen Roberts, an entrepreneur who acquired Red Bike Advisors, a remote-first accounting, tax, and advisory firm based in Wilmington, NC.What makes Gretchen’s story unique? She’s not a CPA and doesn’t come from an accounting background. Before buying the firm, she worked in marketing at a major public tech company. Now, she owns and operates a professional services business — without ever having prepared a tax return._______________________________👉 Sign Up For Free to the SMB Deal Hunter Newsletter: https://join.smbdealhunter.xyz🤝 Work With Me to Help You Find, Finance, and Acquire a Business in 6-12 Months: https://pro.smbdealhunter.xyz 

Savannah Rush, Managing Partner at Funded Ventures and former McKinsey consultant and HBS grad, left consulting to buy and operate home‑services firms. She describes sourcing two small acquisitions, turning a paper-based electrical company around, and raising prices without big churn. She also discusses community networking for proprietary deals, using tech and scorecards to stabilize ops, and a long-term buy-and-build hold strategy.

Michael Bourgeois, an Air Force veteran and former private equity analyst who cofounded Skyline Partnership. He explains buying two off‑market $5M+ businesses with no outside investors. Short takes on their off‑market sourcing playbook, why they contact thousands of companies to close one deal a year, their use of direct mail and a CRM habit to keep cold leads alive, and the long‑term holding company vision.

Alejandra Barrera, an M&A advisor who started in Miami and worked in Deloitte, explains how brokers sort 65 inquiries down to the serious buyers. Short takes on what brokers need in the first 48 hours. Tales of deals gone wrong and why speed, prep and the right documents win hot listings. Practical tips on follow-up, seller expectations and standing out in competitive processes.

Colin King, a finance-focused acquisition entrepreneur with accounting and PE experience, and Joe Van Deman, a serial acquirer who scales small businesses, share their unlikely Craigslist meeting and how they bought 15 companies together. They recount buying an overnight auto-parts delivery route, surviving brutal hands-on nights, hiring operators at odd hours, flipping to PE, and their repeatable sourcing, diligence, and operator-first scaling playbook.

What would you pay for a failing street sweeping business that was:Making $200k / Year in revenue (down from $1.1M) Barely breaking even on profit With trucks breaking down constantlyUnderpaid drivers (constant turnover) Brandon Dixon paid $0 down.100% seller financed with a 60-month term. He jumped head first into the turnaround with no experience and turned it into a $96K/month business in 14 months.We dove into a few big questions throughout the interview...❓️How did a professional baseball player buy a failing street sweeping company for $0 down and 5x revenue in 14 months?❓️Why did Brandon say he'll "never buy this small again" - and what would he do differently?❓️How is Brandon running a 35-40% margin business from 7 hours away with an offshore hire managing day-to-day operations?❓️What happened when 3 trucks broke down on his first day as a full-time operator - and what did it teach him about equipment businesses?_______________________________👉 Sign Up For Free to the SMB Deal Hunter Newsletter: https://join.smbdealhunter.xyz🤝 Work With Me to Help You Buy a Business: https://pro.smbdealhunter.xyz

Join me as I interview Brian Wolfe, a lawyer, small business investor, and PE and search fund professor. Brian founded Funded Ventures, which partners with builders to buy and build small businesses. Their first platform which was formed to acquire SaaS companies in the martech space successfully exited to Alpine Investors after 3 completed acquisitions in 20 months._______________________________👉 Sign Up For Free to the SMB Deal Hunter Newsletter: https://join.smbdealhunter.xyz🤝 Work With Me to Help You Find, Finance, and Acquire a Business in 6-12 Months: https://pro.smbdealhunter.xyz 

In this week’s episode, we're diving into the world of online business acquisitions with Jacky Chou. He's built a portfolio of 50+ online businesses over the last 10 years. And today, he runs ~20 revenue-generating assets doing around $200K/month.And he shares all of it publicly online…But here's what makes this episode fascinating: Jackie doesn't sugarcoat the risks and takes us through countless war stories.He bought a towing directory for $10K, grew it, and flipped it for $195K in 6 months. Sounds amazing, right?Except halfway through, he realized the people he was negotiating with on the East Coast were all connected. "I'm pretty sure they're affiliated with some sort of organized crime... they started making subtle threats."He got out fast.Then there's… The $300K bundle of affiliate sites that went to zero. The Amazon rate card that got yanked overnight with no notice. The revenue rollercoaster from $70K to $560K back down to $200K/month.When I asked him about the risks in the space, he said:"If you were to look back three years ago, the sites that are still remaining today would be like 5% max. They're all dead."Here’s a sneak peek into what we cover: 🔥 How Jackie runs diligence on online businesses in a few days (and red flags he's caught)🔥 Why he had to let go of 60% of his team after AI hit🔥 The "distribution engine" he plugs acquisitions into for immediate revenue🔥 His current thesis on buying vs. building (it's flipped)🔥 Why he keeps 30-40% of his net worth in cash and treasuriesWhether you're curious about online assets or just want to understand platform risk before it bites you, this one's a must-watch.-------------------------------👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

This week’s episode with Bill Haig is one of the most impressive absentee owner stories we’ve featured.Bill owns 4 gym locations in Northern Virginia…. But he’s never been inside any of them.That’s a lot of first time business buyers’ dream. A ‘passive business’. But how did he get here? Bill was an Army officer who bought his first gym with zero fitness experience right after his MBA. And after spending the first few years in the business, he was able to work himself completely out of the day-to-day.In the episode, we talk about that and…🔥 What he learned in his first year of being involved in the business. (And some serious skeletons in the closet) 🔥 How he fixed the gym’s broken business model to one that made it possible for him to scale to 4 locations. 🔥 The "fetal moment" he went through after taking over the business, where he was doubting whether he’d made the right call. -------------------------------👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz

Your first business acquisition wipes out your life savings.Your brother has to sell his house to cover the debt. You sell a property just to get back to zero.Most people would never touch a business deal again.Nathan Lenahan bought 4 more and built a $13M/year HVAC business.His story involves 5 acquisitions, 1 catastrophic failure, and 4 wins that took him from broke to $13M/year.Here's what makes it worth watching...🔥 He lost everything on his first $350K acquisition of a Diesel Repair business in 2018. (The seller stole from customers, violated non-competes, and falsified the lease)🔥 He was making so little on his first HVAC acquisition that he started a recruiting business that did $350K year one, $600K+ year two. He’s now working 3-4 hours per week on it.🔥 He grew his HVAC business from ~ $1M to $13M in revenue in ~3.5 years. And some of his most insightful lessons: ❓ The 5 deadly mistakes he made on his first deal ❓ His integration playbook after 4 HVAC acquisitions ❓ Why he's spent "more time on compensation plans than anything" (and how he's evolved pay structures every single year)And unforgettable moments like..."That was our life savings. All our money was gone…My brother had to sell his house to take care of the debt. I had to sell one of my properties as well to kind of get back to zero... The hard thing is, I would do it again."— Nathan-------------------------------👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz