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He Bought His First Business at $17M and 2x'd It in 5 Years
May 1, 2026
52m 24s
Why He'd Rather Hold 6 Businesses for 40 Years Than Flip Them
Apr 24, 2026
1h 04m 27s
He Put $0 Down and Sold It for $35 Million
Apr 17, 2026
1h 01m 05s
His Business Is Boring, But It Returns 50% a Year
Apr 10, 2026
1h 22m 26s
Why He's Buying "Dead" Bowling Alleys Nobody Wants
Apr 3, 2026
51m 37s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 5/1/26 |  He Bought His First Business at $17M and 2x'd It in 5 Years✨ | business acquisitionprofit doubling+4 | Adam | SMB Deal HunterTwitter+1 | — | business acquisitionEBITDA+4 | — | 52m 24s | |
| 4/24/26 | Why He'd Rather Hold 6 Businesses for 40 Years Than Flip Them | Ryan spent 30 years in corporate America running businesses for other people. Then he got fired twice — never for performance, always for politics. He decided to never build for someone else again.He co-founded North Park Group with his partner Greg Topol and built a holding company designed around one rule: never exit. Since 2022, he's bought 6 businesses in manufacturing and industrial distribution. He plans to own them until he's 85.❌ No 5-year flip❌ No PE-style fund timeline❌ No 7-year wait for investors to see a returnHis investors got their first distribution checks in 2022 — the same year he closed his first deal. He pays them twice a year. Today, 8 out of 10 people he pitches say yes.In this episode, Ryan breaks down why he'd rather hold a business for 40 years than flip it every 5, how he wins deals without being the highest bidder, and why his year-one operating playbook at every company he buys is "don't fuck it up."◼️ Why holding for 40 years can make you just as much money — if not more — than flipping every 5◼️ The "distributions as proof points" model that converts 8 out of 10 investors◼️ How he wins deals without being the highest bidder (one was 10% below the top offer)◼️ The pre-LOI diligence inversion that lets him walk away before lawyers get involved◼️ The $250K he lost on the one deal that broke — and what it taught him◼️ The SBA-stacked operator model he uses to scale past his personal $5M lending capSubscribe to the SMB Deal Hunter newsletter (200,000+ subscribers): https://join.smbdealhunter.xyz/Want help buying a business?Learn about SMB Deal Hunter Pro: https://pro.smbdealhunter.xyz/Follow Helen:Twitter: https://x.com/HelenGuo_LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/ | 1h 04m 27s | ||||||
| 4/17/26 | He Put $0 Down and Sold It for $35 Million | Jake spent 12 years selling data analytics software at SAP, MicroStrategy, and Informatica. Then SAP reassigned him from federal government sales to retail. He decided to take his career into his own hands.He acquired a money-losing, 7-person government data analytics firm with 100% seller financing. Zero cash out of pocket.❌ No playbook for buying a business❌ No community or infrastructure around acquisitions❌ Business was unprofitable on day one10 years later, he sold it for $35 million at 11x EBITDA.In this episode, Jake breaks down how he negotiated 100% seller financing on a deal nobody wanted, how he went from 54% customer retention to 95%, and why the hustle that saved the business early on was the same thing holding it back from growing.◼️ The two-valuation trick that got both sides to agree on the price◼️ Why the sellers financed the whole deal (and how to find sellers like this)◼️ How he went from stuck at 5% growth to hitting 35-40% growth rates◼️ The $35M exit and why his financial advisor told him to take it◼️ The PE earn out nightmare — and how he eventually collectedSubscribe to the SMB Deal Hunter newsletter (200,000+ subscribers): https://join.smbdealhunter.xyz/Want help buying a business?Learn about SMB Deal Hunter Pro: https://pro.smbdealhunter.xyz/Follow Helen:Twitter: https://x.com/HelenGuo_LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/ | 1h 01m 05s | ||||||
| 4/10/26 |  His Business Is Boring, But It Returns 50% a Year | Greg Geronemus went from Goldman Sachs to Harvard Business School, where he stumbled into the idea of buying a small business instead of starting one. He and his partner David Rosner raised $550K in search capital, built a database of 30,000 companies, and spent nearly two years searching for the right deal.They signed one LOI. It was for a business that checked none of the boxes: an old-fashioned B2C tour operator sending baby boomers on group trips around the world. He bought it for $29 million at under 5x with a 50% seller note at 4%.Four years later, he sold to a private equity firm. Nearly 50% annualized returns. Almost 5x net to investors. Today, he runs Footbridge Partners, investing in the next generation of searchers. | 1h 22m 26s | ||||||
| 4/3/26 | Why He's Buying "Dead" Bowling Alleys Nobody Wants | Mike Fagan is a former professional bowler who spent 13 seasons on the PBA tour before getting his MBA at UC Berkeley Haas and working in management consulting. In April 2025, he acquired Ten Pins and More, a bowling alley in Rio Rancho, New Mexico, for $2.05 million including real estate via SBA 7A financing. The bank classified the deal as a turnaround. Today, he owns two locations with a third on the way, operates remotely from Dallas 600 miles away, and is scaling toward $8-10 million in revenue across 3-5 locations.He explains:◼️ Why bowling alleys are undervalued, below replacement cost, and have almost no competing buyers◼️ How he got SBA financing on a deal the bank said wasn't cash flowing enough to cover the payments◼️ The zero-COGS economics behind bowling and why the business fills itself four days a week without marketing◼️ How he went from flying in every week for nine months to running the business fully remote from 600 miles away◼️ Why his pro bowling background gives him an acquisition advantage that no other buyer in the space can replicateSubscribe to the SMB Deal Hunter newsletter (200,000+ subscribers): Join for free here Want help buying a business? Learn about SMB Deal Hunter ProFollow Helen:Twitter: https://x.com/HelenGuo_LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/ | 51m 37s | ||||||
| 4/2/26 |  He Raised $125M on LinkedIn to Buy Boring Businesses (it worked...) | Sam Silverman raised $125 million in investor capital almost entirely through LinkedIn cold outreach solo, no team, no fund behind him. He deployed that capital into a paving company roll-up with four acquisitions in 18 months, an accounting firm he built from scratch, and a private credit fund. He started as an SDR making $37,000 a year.❌ No finance degree❌ No Wall Street background❌ No inherited deal flow — 95% of his capital came from LinkedInIn this episode, Sam breaks down exactly how he went from cold messaging strangers on LinkedIn to managing a portfolio of boring businesses backed by $125 million in investor capital.Sign Up For Free to the SMB Deal Hunter Newsletter: https://join.smbdealhunter.xyzWork With Me to Help You Buy a Business: https://pro.smbdealhunter.xyz/🔥 WHAT YOU'LL LEARN:✅ How he raised his first $20-30 million entirely through LinkedIn cold outreach by targeting people in his own industry, and the peer-to-peer approach that made strangers trust him with six-figure checks✅ The specific LinkedIn Sales Navigator tactic he uses to find investors at the exact moment they can deploy capital — people who switched jobs in the last 90 days and can roll their 401k into a self-directed IRA✅ Why he chose paving over HVAC, landscaping, or any other blue-collar roll-up — and how one concrete acquisition would add $2 million EBITDA to the bottom line on day one✅ How he structures deals so sellers stay on and actually enjoy working post-acquisition, and why every new LOI in his pipeline came as a referral from a previous seller✅ The 1.5-2x equity step-up structure he recommends for first-time buyers who want to acquire a business with little or no capital of their own✅ Why he says go bigger on your first deal — and the specific risk he sees in buying anything under $1 million in EBITDA✅ Where to find investors if you have no track record, no credibility, and no network — and why he says industry conferences are the worst place to look | 57m 44s | ||||||
| 3/20/26 |  Why This Startup Founder Bought an Electrical Contracting Business | Fred McGill of Bray Electrical | Join me as I sit down with Fred McGill from Atlanta, Georgia–a former startup founder who made the leap into small business acquisition.Exactly one year ago, Fred acquired Bray Electrical Services, an electrical contracting business. In just 12 months, he’s grown the top line by $650,000, while still running his real estate brokerage on the side.If you’re thinking about buying a business in the trades or want a real look at what it takes to scale one, don’t miss this story._______________________________👉 Subscribe to the SMB Deal Hunter Newsletter — free weekly deals & insights: https://join.smbdealhunter.xyz🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz | 57m 46s | ||||||
| 3/13/26 |  How He Went From English Teacher To 40 Business Acquisitions | Join me as I interview Dominic Wells, the CEO of Onfolio, a publicly traded portfolio of around 20 internet businesses ($ONFO).Dom went from making $1-$2K/month teaching English in Taiwan 10 years ago to acquiring about 40 online businesses over the past decade._______________________________👉 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 | 56m 18s | ||||||
| 3/6/26 |  How He Makes $100k+/mo With 800 ATMs | Mitchell Sorkin | Join me as I interview successful acquisition entrepreneur Mitchell Sorkin.Mitchell left the startup world after bootstrapping his business Stack Influence to $1M. He then got into acquisition entrepreneurship by buying ATM routes. Mitchell first bought 3 ATMs in Oct. '21 and now owns 800+ ATMs. _______________________________👉 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 | 33m 50s | ||||||
| 2/27/26 | He's done 200+ QofEs. Here's what sellers don't want you to know | Mubarak Shah | Here's a number that should make you uncomfortable.98% of the time, when a CPA digs into a business's financials, the real EBITDA comes back different from what the seller claimed.And we're not talking about rounding errors. The real EBITDA is a different number entirely.Sometimes it's 5% off. Sometimes it's 50% off. And in about a third of cases, the deal dies right there.That number comes from a CPA who's done over 200 quality of earnings reports, on both the buy side and the sell side.This week, I sat down with Mubarak Shah, a CPA, M&A advisor, and QoE specialist who also works with our members inside the Pro program.Mubarak started his career in audit, became VP of Finance at a startup that raised a $10M Series A, and cut his teeth doing QoEs at firms that served private equity clients. He's now completed over 200 of them.He's seen every trick in the book. And in this episode, he walks through exactly what sellers do to make their businesses look more profitable than they are.Here are some of the highlights from the deep dive:🔥 The seller accounting trick that sails right past SBA underwriting and can cost you millions (it's shockingly simple)🔥 Why your bank's underwriting isn't designed to protect you, and what it's actually designed to do instead🔥 The one M&A concept that nobody actually understands that led to a seven-figure lawsuit🔥 A breakdown of exactly what happens during a QoE, what it costs, how long it takes, and why the biggest bottleneck has nothing to do with the accountant_______________________________👉 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 | 57m 47s | ||||||
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| 2/20/26 | This CPA made all the MAJOR mistakes so you don't have to | Rushi Amin | You'd think a CPA with six years at a Big Four firm and four years in investment banking would catch every red flag in a small business acquisition, right? Wrong. Rushi missed three big ones on his first deal. He overpaid on the franchise.He didn’t realize 25% of the franchise’s global locations were packed into his backyard. And the business had to close for four months a year, which sounds great until your GM quits because they can’t afford to go all winter without a paycheck.That was just deal #1. He was crazy enough to go back for round 2…Here's what makes this episode worth watching...🔥 How his second deal ended up being a one-man business with 90% margins (and how he grew it 20% in the first year)🔥 How he brought his first acquisition to break even (after a disastrous start)🔥 Why he’s going all in on business acquisition (and his third acquisition target)_______________________________👉 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 | 1h 03m 26s | ||||||
| 2/13/26 | ![How This Entrepreneur Bought a $1.3M Home Service Biz and Sold it to PE for $5.8M a Few MONTHS Later [Greatest Hits] episode artwork](https://img.transistorcdn.com/X2kt_USl8_njrfpH0RGj4Jg-lak_CyL78q8nbLkUi9w/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8zY2Vh/YzExMGJjMWIzNTkx/ZGI0OTQzNTU5ZTY0/ODVlYi5wbmc.jpg) How This Entrepreneur Bought a $1.3M Home Service Biz and Sold it to PE for $5.8M a Few MONTHS Later [Greatest Hits] | Join me as I interview successful acquisition entrepreneur Steve Keller.We discuss how Steve went from being a cameraman with zero business background to buying and selling two crime scene cleanup 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 | 52m 55s | ||||||
| 2/6/26 |  How This Serial Acquisition Entrepreneur Left His Corporate Career and Bought 10 Businesses | Join me as I interview serial acquisition entrepreneur Ujwal Velagapudi.Ujwal left his corporate career working in supply chain management to buy small businesses. His experience spans a variety of industries, from buying a local sports bar and gym (among others) to now focusing on amusement vending machines. _______________________________👉 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 | 57m 13s | ||||||
| 1/30/26 | ![[Greatest Hits] Buying an Accounting Firm Without Being a CPA? She Did It. episode artwork](https://img.transistorcdn.com/ZsMNeUM_Kgv4VBREjNsgJrIMFQjI47_BaqZ1NzZ1xJ8/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8wYjgw/MzJlMzA1MjczMDE3/ZTBmMGNiMTQwZDgw/ZGMxYi5wbmc.jpg) [Greatest Hits] Buying an Accounting Firm Without Being a CPA? She Did It. | 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 | 49m 00s | ||||||
| 1/23/26 | McKinsey Consultant -> Two $1M+ Businesses in 2 years | Savanna Rush | This week, I sat down with Savannah Rush, Managing Partner at Funded Ventures.Savannah went from McKinsey consultant to owner-operator of Midway Electric in Columbia, Missouri. She and her partner Brian Wolf (who I interviewed previously) have closed two home services deals and are laser focused on building a long-term holding company.She's not aiming to flip or exit. Her goal is to build a compounding machine. Here are some of the highlights from the deep dive:🔥 How she went from "ETA skeptic" to running an electrical company in a market where she doesn't exactly look like the typical president🔥 The state of the business when they bought it (everything was on paper, hourly rates were 40% below market, and the owners were barely holding on)🔥 How they turned it around in months, including the pricing conversation with the team that actually got buy-in🔥 Why they're willing to go "super, super small" on acquisitions when everyone else says to go biggerHere's her must-watch breakdown...She also shared some things I don't hear enough people admit out loud:❓ Why she was nervous about stepping into the role ❓ The one thing her McKinsey background didn't prepare her for ❓ Why "being involved in the community" has become one of their biggest unlocks for finding proprietary deals | 58m 52s | ||||||
| 1/16/26 | He bought two $5M+ companies in 2 years (completely off market and with no investors) | Michael and his partner, Ashish, only buy businesses that are $5M+ in EBITDA (way above the SBA limit).He aims to buy a new one every year. And the last two he bought, were completely off market. To that point, 90% of his sourcing is off-market.No BizBuySell. No broker bidding wars. Just relationships built over time at conferences, through colleagues, and by doing a lot of outreach. But we’ll get to that. First, a little bit of background…Michael is an Air Force veteran and former private equity analyst. He and his partner run Skyline Partnership, a holding company with two acquisitions: a cybersecurity software developer and an HVAC company doing $13-15M in revenue.They’re aiming to build a holding company that they can pass off to their children. One that’s built to last. And they’re just getting started. And in today’s interview, we dive into a few topics: 🔥 The off-market sourcing playbook that's landed both of their deals (no brokers involved)🔥 How many companies you actually have to reach to close one deal a year at their scale (the number might surprise you)🔥 Why they send direct mail to business owners in target geographies (and what actually gets through)🔥 The CRM habit that keeps cold leads alive until they're readyHere's his must-watch breakdown...He also shared some tactical advice I don't hear often:❓ Why he thinks most searchers are "too agreeable" with brokers (and how to push back)❓ What to do when a seller says "not interested" (hint: don't delete them)❓ The industries he's most bullish on right now (they’re not the ones you usually hear)And moments like this..."We bought an HVAC company from a private equity firm. The old GM showed up, gave us a tour, handed us the keys, and said 'good luck.' No transition. No documentation. Nothing. The first two weeks is the first time in my life I've actually lost hair."— Michael_______________________________👉 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 | 54m 10s | ||||||
| 1/9/26 | How to stand out with brokers and win competitive deals with Alejandra Barrera | You've probably done this…You found a listing you liked. You sent the NDA. Maybe you even fired off a quick note about your background and the things you’d like to learn.Then... nothing.A week later, the deal’s under LOI. No call back, no response to your request. Here's what you didn't see:That listing probably got 65 inquiries in the first few days. Of those, 10 of them came in prepared.The rest never got a serious look. Not because they weren't qualified but because they didn’t understand how to cut through the noise and get the broker’s attention. This week I sat down with a broker who's going to show you exactly what happens on the other side of a business acquisition.Alejandra has been doing this for years. She started in Miami, sold her first business in 4 months, got recruited into Deloitte's M&A practice, and recently joined our team as an M&A advisor inside the Pro program.She's seen hundreds of deals and dealt with countless buyers. Most of them make the same mistakes.Here’s are some of the highlights from the deep dive: 🔥 Alejandra goes through what the first 48 hours look like from the broker’s perspective when a hot listing goes up🔥 She shares the three documents she needs before she'll present you to a seller. (Most buyers only send one)🔥 She shares loads of war stories on deals that went bad and what you can learn form them🔥 And she pulls back the curtain on why brokers often don’t return calls, why ‘cash offers only’ listings are usually not serious, and how you can stand out from the crowd when competing for a popular business._______________________________👉 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 | 1h 06m 49s | ||||||
| 12/19/25 | How These 2 Partners Met on Craigslist & Ended Up Buying 15 Companies Together | Joe Van Deman and Colin King | This week's episode starts with a horror story.Joe and Colin from Circle City Capital Group bought their first business together in 2018. After meeting on Craigslist (yes, seriously)They bought an overnight delivery route business specializing in auto parts. They started with 5 routes and put in less than $100k to acquire the business.But on their first night as owners…two drivers didn't show up.So Joe and Colin got in the trucks themselves. And for the next few months, that became the routine. Driving 400 miles a night. Colin doing it while still working a full-time job.The business ran their lives.So why did they go on to buy 14 more?Because somewhere in that chaos, they figured out how to work on the business vs in it. Hiring an operator. Getting out of the day-to-day. And beginning to scale. Today they've done 15 acquisitions across consumer brands, e-commerce, and financial services. Every business in their current portfolio has a GM or CEO in place. And they're closing three more deals in Q1 of 2026.Here's are some highlights worth watching...🔥 The 11:30pm Denny's interviews that helped them find their first real operator🔥 How they flipped that nightmare first business to a PE firm in 18 months🔥 The "two filters" they now run every deal through before buying 🔥 A story involving train tracks that explains why they tell people to work in a small business before buying one | 1h 05m 54s | ||||||
| 12/12/25 |  This MLB Player Acquired A Street Sweeping Company With $0 Down And Grew It By 5x In 13 Months | 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 | 40m 12s | ||||||
| 12/5/25 | ![[Greatest Hits] How This Big Law Partner Rolled Up 3 MarTech SaaS Companies In 20 Months And Sold to PE episode artwork](https://img.transistorcdn.com/m7jFL6GrgNmEQPtGEGX4njL5JUPgjgp-CuSzU4etfjM/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9kOTlj/YTUyNDZjZTAxNmRk/OGQ2YzMxMzUyNjE3/OWEwZC5wbmc.jpg) [Greatest Hits] How This Big Law Partner Rolled Up 3 MarTech SaaS Companies In 20 Months And Sold to PE | 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 | 1h 05m 10s | ||||||
| 11/28/25 |  He's acquired 50+ online businesses making $200k+ / month. (Here's how he does it) | Jacky Chou | 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 | 40m 33s | ||||||
| 11/21/25 | ![[Greatest Hits] He owns 4 gyms but he's never been to any of them. (Here's How) | Bill Haig episode artwork](https://img.transistorcdn.com/fTLrMVgJnGl3UJhE8H3Y-8xPj1utwj6kyZWQbTXH_ro/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8xZjdh/NGE1YTE5OTYyODhm/NGU4ODA5M2U3MGZh/M2VkNy5wbmc.jpg) [Greatest Hits] He owns 4 gyms but he's never been to any of them. (Here's How) | Bill Haig | 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 | 55m 29s | ||||||
| 11/14/25 |  -$350k → $13M/Yr: From failed acquisition to HVAC rollup | Nathan Lenahan | 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 | 53m 57s | ||||||
| 11/7/25 |  $50k → $5M buying declining healthcare businesses (here's how) | Devin Fitzgerald | Devin Fitzgerald acquired 2 declining home healthcare businesses in the Boston area over the last few years and successfully turned them around. He did it with some of the most creative financing we’ve seen on the show. And he’s already working on acquisition #3 (which is 4x bigger than all of his current businesses combined). At some points his story is nearly unbelievable. Here are just a few snippets from his interview...🔥 He bought his first two healthcare businesses making ~$5M in Revenue with only $50k down (and says he shouldn't have put down anything at all)🔥 He was negotiating six-figure deals while delivering pizzas—literally putting bankers on hold to hand off a pepperoni pizza for a $3 tip🔥 He bought a business declining 21.5% per year with zero healthcare experience (and turned it around in year one). Then did it again with business #2 (declining ~6% a year).And some of his insightful lessons: ❓ Why he bought declining businesses (one falling 21.5% annually) when most buyers would run away❓ The book that completely changed his integration strategy (hint: it's about Warren Buffett and John Malone)❓ How he's differentiating in healthcare where rates are often capped and everyone competes on the same playing field-------------------------------👉 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💼 Connect with me on LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/ | 51m 27s | ||||||
| 10/16/25 |  He broke ALL the rules of acquisition and still succeeded | Walker Yarbrough | I’m very excited to share this week’s interview with Walker Yarbrough. He started off with long hours in Investment Banking until he looked up at his bosses and he realized he didn’t want their job (at all). "Even once they'd climbed the ladder, they still just didn't have a lot of control of their own time…They were doing great by a lot of standards, but in the office super late and working on weekends and traveling all the time. It was just a future I didn't see for myself."WalkerSo, Walker did what a lot of us do who want to get into ‘business’. They do literally everything under the sun, hoping something will work:$35,000 on an Amazon automation store. Started great—days with $1,000+ in sales selling Calvin Klein cologne. Then Amazon banned the store. Money gone.Print-on-demand t-shirts. His girlfriend had a successful Etsy shop, so why not? Too competitive. Went nowhere.Options trading. Sometimes worked. Mostly stressful. Never consistent.Sports betting analytics site. Got CLOSE. Almost signed the deal. Then Walker realized: "If something breaks, I don't think I'm gonna be able to fix it."Then, he decided to simplify and buy a business he could understand. A vending machine company with 7 locations in Atlanta. Fully owner-operated by a 75 year old who wanted to retire. But here’s where things get interesting: 💡 Walker had to beat out an experienced vending machine company competing for the same deal. 💡 The deal got held up for 2 MONTHS over a $200 bill. 💡 And when it DID close, Walker made a classic first-timers mistake. He hired an operator to run the business and went off on vacation. Aiming for a ‘passive’ investment. Until the operator quit 3 months later. The full story involves a panicked craiglist job hunt, Walker losing one of his biggest customers, and realizing that the business was practically run out of the previous owner’s car. It’s a wild ride. And at the end, Walker not only succeeded but excelled. So much so, that he’s one of our new M&A advisors. -------------------------------👉 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 | 1h 06m 11s | ||||||
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