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. From $18M AI Founder to a Cleaning Business (Working 15hr/week)

    2d ago

    From $18M AI Founder to a Cleaning Business (Working 15hr/week)

    Want help buying a business? https://smbdealhunter.link/pro-yt In this episode, Rob Carpenter breaks down why he walked away from an $18M AI company to buy residential cleaning businesses, how he closed his first deal in six weeks, and what running blue-collar companies actually taught him. ◼️ Why three of the most powerful people in AI convinced him to bet on blue collar instead of white collar◼️ How he closed his first acquisition in just six weeks, and the one holdout that almost blew the timeline◼️ The off-market deal he landed from a 72-year-old who'd owned his location for 40 years◼️ The expensive mistake he made in his first six months that made him reverse every single change he'd made◼️ What a 15-hour work week actually looks like when you're done by 11am and picking your kids up at 3 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/

    54 min
  2. How She Went From a Tech Layoff to a $1M+ Business

    6d ago

    How She Went From a Tech Layoff to a $1M+ Business

    Want help buying a business? https://smbdealhunter.link/pro-yt In this episode, we catch up with Hillary one year after her acquisition of a $1M+ children's book publisher. The last time we sat down with her, she had just closed. Eighteen months later, almost everything has changed. If you want to see our first video with Hillary, watch it here: https://youtu.be/Sf6vSOzQOWc ◼️ The same-day deadline that forced her to submit her offer by close of business (and how she beat 12 other LOIs to win) ◼️ The diligence period that nearly killed the deal multiple times (and how our team kept it alive all the way to close) ◼️ The surprise identical twins six months after close (and why her husband Scott walked away from his corporate job to join her full-time) ◼️ The Amazon diversification she was warned would be brutal (now Barnes & Noble, Books-A-Million, Walmart, and Target make up 30% of the business) ◼️ The 18-month playbook that took top-line revenue to nearly double what it was at acquisition 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 10m
  3. Why He Won't Sell The Business He Could Exit For $18M

    May 29

    Why He Won't Sell The Business He Could Exit For $18M

    Want help buying a business? https://smbdealhunter.link/pro-yt In this episode, Paul breaks down how he left corporate to buy his first business when his wife got pregnant with their second baby, why he's bought 12 businesses in 25 years and refuses to sell the cash cows, and how he's setting up all five of his kids to run the exact same play. ◼️ What he sold (and downsized to) so his pregnant wife could stay home and he could buy his first business ◼️ Why he still works just 5-10 hours a week at the first business he bought 25 years ago ◼️ The lighting store he closed on two weeks before the 2008 housing crash ◼️ The single property he kept after selling the business attached to it (now worth $2.5M and paying him $100K a year) ◼️ The business he built from zero that he could sell for up to $18M (and why he won't) 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 7m
  4. How She Bought A $3M Pet Food Business Making $500K/yr (For 10% Down)

    May 25

    How She Bought A $3M Pet Food Business Making $500K/yr (For 10% Down)

    In this episode, Chelsea breaks down how she bought a $1.7M raw pet food business after 12 years at Boeing and Amazon, the off-market deal that "broke up" and came back to life nearly a year later, and the performance-based seller's note that bridged a valuation gap when bird flu cratered 2025 sales. ◼️ The "Hail Mary" offer she sent the seller nine months after their first deal collapsed◼️ The one moment that killed the first deal a few months in (and how the seller's son ended up on her team anyway)◼️ The financing structure — 10% down, SBA loan through Climate First Bank, and a sales-tied performance note — that closed a $1.7M deal with no outside investors◼️ Why she spent her first year hunting virtual businesses before realizing she needed a local, physical operation◼️ How her corporate negotiation training saved the relationship with her biggest wholesale customer in month four 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/

    43 min
  5. How He Went From $0 to $1.8M/yr (While Living on His Wife’s Salary)

    May 22

    How He Went From $0 to $1.8M/yr (While Living on His Wife’s Salary)

    Want help buying a business? https://smbdealhunter.link/pro-yt In this episode, Robert breaks down how he bought a $7.3M home care business while living on his wife's salary, the financing structure that closed it without a single outside investor, and the year-one rebuild where he fired every employee he inherited. ◼️ The 24-month deal he made with his wife before launching the search ◼️ The one mistake that killed his only deal three months in, and the conversation that brought it back ◼️ The financing structure that closed a $7.3M business with zero outside investors ◼️ Why he fired every member of his inherited office team in year one, and what it took to rebuild ◼️ Why targeting $300K of cash flow and closing on something 3x bigger is what saved his first year 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 13m
  6. How He Bought a 51-Year-Old Business for ONLY 7% Down

    May 18

    How He Bought a 51-Year-Old Business for ONLY 7% Down

    Want help buying a business? https://smbdealhunter.link/pro-yt In this episode, Jonathan breaks down how he bought a 50-year-old electrical contractor for $7M with just $500K down, the seller financing structure that made it work, and the 4-month chaos he survived to close it. ◼️ Why he stopped starting businesses after 20 years and bought one instead ◼️ The 10-year seller note that let him close a $7M deal with just $500K down ◼️ How he beat a Texas family office trying to roll the company into a 10-office portfolio ◼️ The eight-word legal dispute that killed the deal, and the Waffle House breakfast that brought it back to life ◼️ The tax strategy he'd never heard of that put another five figures back in his pocket on the down payment 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/

    55 min
  7. How He Went From $0 to $1B/yr in ONLY 5 Years

    May 15

    How He Went From $0 to $1B/yr in ONLY 5 Years

    Want help buying a business? https://smbdealhunter.link/pro-yt In this episode, Steven Carroll breaks down how he turned his first HVAC acquisition into a $1B+ business in 5 years, the partnership model behind 32 more deals, and the $10 billion target he's chasing now. ◼️ Why three general managers in a row walked away from his very first attempt to buy a business ◼️ The $1.5 million hole on a $2 million profit business that nearly broke him in year one ◼️ The one seller who said yes after a year of pitches, and the model that unlocked 32 more deals ◼️ How he closes 8 to 10 acquisitions a year while processing 350 to 400 deals through his team 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 4m
  8. How He Bought a $1.37M Business WITHOUT Quitting His Job

    May 11

    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
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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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