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The SMB Deal Hunter Podcast: Daily Summaries Delivered
by Helen Guo
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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The most recent episodes — sign up to get AI-powered summaries of each one.
- Yesterday32 min
How He Bought a $965k Business WITHOUT Quitting His Job
Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Mike breaks down why he bought a medical transportation company he'd never heard of, how he closed it with just 5% down after losing the deal once, and what running it remotely in 10 hours a week actually takes.◼️ Why he lost this deal to a bigger buyer, and the relationship move that brought it back a month later◼️ How a creative seller note got him to just 5% down on a $965K business◼️ His "freakout moment" when the bank quit 60 days into underwriting, and how he closed anyway◼️ Why an aging population gives non-emergency medical transportation built-in, growing demand◼️ What running a Michigan business from his home in Florida in 10 hours a week actually takesSubscribe 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/
- 4 days ago1h 3m
How 2 Friends Bought a Business That Prints $780K/yr
Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Sarah and Matthew break down why they left venture capital to buy the only auto shop in their hometown of Aspen, how they pulled off a $1.5M acquisition with almost no money of their own, and how one shop became the first piece of a $100M+ holding company built around a single small town.◼️ The financing structure that let two friends with almost no personal capital buy a $1.5M business and still keep 70% of the company◼️ Why the only auto shop in Aspen was a mini monopoly hiding in plain sight, and why nobody else was competing to buy it◼️ What happened six weeks after closing when the operator everyone thought owned the shop walked out, and how they survived running the front desk from 7:30am to 9pm for six months◼️ How a cold call to a stranger's assistant landed the backer who helped them buy out every investor at a 2x return in just 13 months◼️ The deal that almost became acquisition number two and died after four months, and what it taught them about which businesses to never chaseSubscribe 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/
- 1 weeks ago19 min
He Stopped Investing In Real Estate, This Is Why…
Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Jason breaks down why he walked away from flipping houses to buy a $1.3M landscaping business, how he found his deal in a single month after eight months of getting nowhere on his own, and how the years he spent running purchasing became his biggest edge as an owner.◼️ Why eight months of searching on his own got him nowhere, and the one thing that changed the month he stopped going it alone◼️ How he found his deal in a single month once every listing was in one place instead of scattered across a dozen different sites◼️ The $1.3M business he won in one of the wealthiest counties in Florida, where a single job can run $100K to $500K◼️ The supplier network from his old purchasing career that's about to cut his materials costs nearly in half◼️ The growth lever sitting untouched: the previous owner never spent a single dollar on marketingSubscribe 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/
- 1 weeks ago54 min
From $18M AI Founder to a Cleaning Business (Working 15hr/week)
Want help buying a business? https://smbdealhunter.link/pro-ytIn 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 3Subscribe 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/
- 2 weeks ago1h 10m
How She Went From a Tech Layoff to a $1M+ Business
Want help buying a business? https://smbdealhunter.link/pro-ytIn 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 acquisitionSubscribe 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/
- 2 weeks ago1h 7m
Why He Won't Sell The Business He Could Exit For $18M
Want help buying a business? https://smbdealhunter.link/pro-ytIn 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/
- 3 weeks ago42 min
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 fourSubscribe 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/
- 3 weeks ago1h 12m
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-ytIn 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 yearSubscribe 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/
About The SMB Deal Hunter Podcast
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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