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
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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz
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
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🤝 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/
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."
So, 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:
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.
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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz
I’m very excited to share this week’s interview with Raj Kankaria.
It is an absolute roller coaster involving layoffs, divorce, rappers, a quarter life crisis, and Raj buying a $1.3M / year business with 100% seller financing.
Here’s a sneak peak:
Raj was a former army vet who had gotten a job at Citi Bank as an investment banker.
He had just been laid off.
He was in the middle of a messy divorce.
And one day, he opened the door to a process server who handed him his divorce papers.
Out of curiosity, Raj asked the man how much he made for every delivery.
The answer: Over $100 per delivery
So, Raj started digging in…and 18 months later, with a lot of twists and turns along the way, Raj ended up OWNING a company that did exactly that.
But it gets crazier:
💡Raj ended up negotiating a 100% seller financed deal (after his SBA loan fell through)
💡He ended up building the biggest litigation support company in Harris County. With $1.3M in revenue. 1000+ contractor network. And a recession-proof business model.
💡 And before all that, Raj actually spent over a year working as a process server himself. (And he shares advice on why this was pivotal to his success later on)
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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz
Join me as I interview Kofi Acheampong...
Kofi’s interview is unique because he actually went through our Pro program and bought a Home Restoration business cash-flowing $715k+ / year in a record 5 months.
But this interview goes a lot deeper into…
💡 How Kofi actually launched a software startup that got to #3 on Product Hunt - and how he walked away when his wife got pregnant and he had no health insurance.
💡 How he bought his $3.2M business with only 5% down and 8 months later, he’s already under LOI on a second deal with 67% seller financing.
💡 How he succeeded in buying the business after 6-7 other people had already tried and failed (including the current GM…who also happened to be the seller’s son-in-law)
👉 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
I’m very excited to share this week’s interview with Michael Loftus.
Michael really shows you how far you can go with a simple strategy. Here are just a few snippets from his interview…
🔥 He bought his first 3 companies with no banks involved…with upwards of 50% seller financing…
🔥 He’s acquired 7 landscaping businesses over the last five to six years (and talks about what makes them so recession resistant)
🔥 He was able to take a 3 week honeymoon last year without taking a single phone call.
And some of the juiciest lessons…
⁉️ How Michael is able to retain 90% of the customers from each acquisition…
⁉️ How he has built up to 80 full-time employees and $6M in revenue
⁉️ His secret for hiring high quality employees (and how acquisitions are a big apart of it)
👉 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
Join me as I interview Andres Martínez...
At some points his story is nearly unbelievable. Here are just a few snippets from his interview…
🔥 He bought a $1.3M auto body shop making about $500k in EBITDA with 1% down. Yes, you read that right. $15,000 down for a $1.3M deal.
🔥 He came from Mexico in 2021, with no house for collateral, no real job, and bought his first business at 25.
🔥 He had dropped out of college and had failed at multiple businesses, mainly food trucks, leading up to his first big acquisition.
And after all of those obstacles?…
🚀 He is already on his way to buying his 2nd and 3rd companies in the Auto Body and Automation niches.
👉 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
Join me as I interview JD Beck, an entrepreneur who is rolling up HVAC and plumbing companies in Colorado. He's made 3 acquisitions to-date, scaling the business from $1.1M to $4.6M in revenue.
👉 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
Join me as I sit down with Michael Kelker, a former corporate exec who spent 15 years in the aviation manufacturing industry before leaving to buy Timberline Pallet, a custom pallet and crating company in the Quad Cities.
With no prior experience in pallets, Michael stepped in as an owner-operator, doubled the business in five years, and grew the team from 15 to 27 employees.
Since then, he’s made two more acquisitions: an auto parts recycler and a manufacturing consultancy (which he exited).
We dive into what it’s really like to run a blue-collar business, team building, why he says he’s “not a good employee anymore," and how he’s building a legacy business for his daughters (GBR Riverdale is named after them).
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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz
Join me as I sit down with Nathan Gregory, a former talent agent in the entertainment industry who acquired Auto Body News, the leading trade publication in the collision repair industry.
Nathan’s journey into entrepreneurship began with flipping raw land and investing in commercial real estate. After building and selling an Amazon-based product business, he spent over a year searching for the right company to buy, ultimately landing on a 42-year-old B2B media company serving auto repair shops and vendors nationwide. He used SBA financing, creative seller notes, and deep industry experience to close the deal.
If you’re curious about how to buy your first business, why domain expertise gives you a competitive edge, or how to modernize a legacy business, you’ll love this episode.
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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz
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.
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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz
Join me as I sit down with Kaustubh Deo, an entrepreneur rolling up tree care businesses in Seattle, Washington.
After a few years in private equity, Kaustubh made the leap into small business acquisitions—starting with his first deal in 2022 using a combination of SBA 7(a) financing, seller financing, and investor capital. Since then, he’s added two more companies to his platform.
If you’re curious about how to transition from Wall Street to Main Street, use debt to buy businesses, or scale through add-on acquisitions, this one’s for you.
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🤝 Work with me and my team 1-on-1 to find, finance, and close your acquisition in 6–12 months: https://pro.smbdealhunter.xyz
Join me for a conversation with Nick Patrick, a former financial advisor turned acquisition entrepreneur. Nick bought a wedding venue and catering business, scaled it, and exited to a family office just 20 months later.
After taking a breather, he dove back in. Earlier this year, Nick closed on a residential and commercial solar company in Denver after a focused off-market search.
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👉 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
Join me as I sit down with Grant Hensel of Entrepreneurial Capital, a fund investing millions to back self-funded searchers buying cash-flowing small businesses.
Grant’s portfolio of 10+ investments includes an industrial fan motor distributor, a light manufacturing company, and a niche procurement consulting firm for schools.
Before launching the fund, Grant and his wife also acquired an SEO agency serving personal injury attorneys.
If you're curious about how capital is flowing into Main Street — and how investors like Grant are fueling the rise of entrepreneur-led acquisitions — this one’s for you.
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👉 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
Join me as I interview B.G. Lemmon from the Brynavon Group, a family office started by B.G.’s grandfather that focuses on management buyouts primarily in domestic manufacturing.
Brynavon currently owns 4 portfolio companies.
Their most recent acquisition in 2022, a stainless steel foundry, has grown from $1.25M EBITDA at the time of acquisition to $3.25M EBITDA today.
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🤝 Work With Me to Help You Find, Finance, and Acquire a Business in 6-12 Months: https://pro.smbdealhunter.xyz
Join me as I interview Sebastian Gast, a former gym franchisee who pivoted into online business acquisitions.
Sebastian acquired a fitness job board a year ago and just acquired an app-based SaaS platform a month ago.
He also previously joined a search-fund acquired company in the oil and gas services space that exited to PE.
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🤝 Work With Me to Help You Find, Finance, and Acquire a Business in 6-12 Months: https://pro.smbdealhunter.xyz
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.
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🤝 Work With Me to Help You Find, Finance, and Acquire a Business in 6-12 Months: https://pro.smbdealhunter.xyz
Join me as I interview Emmanuel Lopez, a former banker who took the leap into entrepreneurship by acquiring a fuel systems maintenance business with a partner and investors.
Nearly three years later, he was asked to leave.
While rare, this scenario can happen to any business buyer. In our conversation, Emmanuel shares the key lessons he learned—the red flags, the surprises, and what he’d do differently next time.
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🤝 Work With Me to Help You Find, Finance, and Acquire a Business in 6-12 Months: https://pro.smbdealhunter.xyz
Join me as I interview Michael Young, a former Director at PwC who left corporate after 10 years to buy an accounting firm.
After a 26 month search, Michael acquired Bay Biz, an outsourced accounting and finance firm based in Washington, DC.
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👉 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
Join me as I interview Dominick Blue, a U.S. Marine Corps veteran and former tech startup entrepreneur, who evaluated 2,500 deals before acquiring two businesses in 2024—an air duct cleaning company and an HVAC business.
In his first summer after taking over the businesses, Dominick increased the volume of work by an impressive 40%.
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👉 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