The SMB Deal Hunter Podcast

Helen Guo
  • 5.0 (10)
  • ENTREPRENEURSHIP

Every week, Helen Guo interviews successful acquisition entrepreneurs, independent sponsors, and investors who have acquired businesses. Learn how to buy a business rather than starting one from scratch from those who have done it themselves.

  1. How He Bought a $1.37M Business WITHOUT Quitting His Job

    2D AGO

    How He Bought a $1.37M Business WITHOUT Quitting His Job

    Want help buying a business? https://smbdealhunter.link/pro-yt In this episode, John Manahan breaks down how he negotiated a yoga studio business down from $2.5M to $1.375M, the franchise bombshell that almost killed his deal three days before close, and how he's running 2 studios on a 1-hour weekly call with his district manager while still billing full hours at Deloitte. ◼️ How he got a business that had been sitting on the market over a year down to less than half its original asking price◼️ Why the SBA life insurance requirement nearly stopped him in his tracks (and the specialty agent who got him approved)◼️ The franchise amendment that dropped 3 days before close and how he kept the deal alive◼️ How a management consultant who'd never taken a yoga class evaluated and bought 2 high-end studios◼️ The exact structure that lets him run both studios on a 1-hour weekly call while keeping his W2 Subscribe to the SMB Deal Hunter newsletter (200,000+ subscribers): https://join.smbdealhunter.xyz/ Follow Helen:Twitter: https://x.com/HelenGuo_LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/

    53 min

  2. 5D AGO

    How He Bought a Tree Care Company (and Built an Empire)

    Want help buying a business? https://smbdealhunter.link/pro-yt In this episode, Brian Hartman breaks down the year-one cash crunch that nearly killed his first acquisition (despite 96% revenue growth), why he turned down private equity offers ten times a day before saying yes to one that let him keep control, and the operator playbook he's now using to roll up tree care companies across three states. ◼️ How he grew his first tree care business from $2.6M to $5.1M in year one and almost went broke doing it ◼️ Why long-term contracts hurt operators (and how transactional pricing let him raise prices through 9% inflation) ◼️ The minority investment structure that let him keep control of his business while joining a fund ◼️ What he learned from a 73-year-old tree climber in Jacksonville that changed how he runs his entire fleet ◼️ The first 5 minutes of an owner conversation that tells him whether to walk away from a deal regardless of price Subscribe to the SMB Deal Hunter newsletter (200,000+ subscribers): https://join.smbdealhunter.xyz/ Follow Helen: Twitter: https://x.com/HelenGuo_ LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/

    1h 6m
  3. He Bought His First Business at $17M and 2x'd It in 5 Years

    MAY 1

    He Bought His First Business at $17M and 2x'd It in 5 Years

    In this episode, Adam breaks down the unusual deal structure that pulled him off the fence, why running a $20M business was harder than running a $150M one, and the single biggest lever he pulled to double the profits. ◼️ The CEO-on-salary trial structure that let him run the business for 6 months before he committed to buying it ◼️ The construction-to-service flip that doubled EBITDA on a 50% revenue lift ◼️ Why running a $150M company was easier than running a $20M one ◼️ The year-one near-disaster that nearly cost him his largest equipment distributor ◼️ Why he managed to EBITDA, never to revenue, from day one Subscribe 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/

    52 min

  4. APR 24

    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 return His 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 f**k 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 cap Subscribe 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 4m

  5. APR 17

    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 one 10 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 collected Subscribe 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 1m
  6. His Business Is Boring, But It Returns 50% a Year

    APR 10

    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

  7. APR 3

    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 replicate Subscribe 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/

    52 min
  8. He Raised $125M on LinkedIn to Buy Boring Businesses (it worked...)

    APR 2

    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 LinkedIn In 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.xyz Work 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

    58 min
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5
out of 5
10 Ratings

About

Every week, Helen Guo interviews successful acquisition entrepreneurs, independent sponsors, and investors who have acquired businesses. Learn how to buy a business rather than starting one from scratch from those who have done it themselves.

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