The SMB Deal Hunter Podcast

Want help buying a business? https://smbdealhunter.link/pro-ytSubscribe to the SMB Deal Hunter newsletter (250,000+ subscribers): https://join.smbdealhunter.xyz/In this episode, Reid breaks down how he bought an $895k manufacturing business on Kauai, Hawaii without quitting the offshore job he'd worked for 15 years, and how he runs it from his home in Las Vegas.◼️ Why he almost skipped the listing, and the conversation at home that changed his mind◼️ Why the seller picked him over two other buyers who offered similar money◼️ The state filing quoted at 15 days that took 10 weeks and put the whole deal on hold◼️ The deal before this one, and what killed it after he'd already flown out to meet the seller◼️ Why the roofing side of the business never worried him, and what didFollow Helen:Twitter: https://x.com/HelenGuo_LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Kyle breaks down why he left a stable corporate career to buy his own company, how he funded the deal without an SBA loan or a bank, and what it took to close a deal that fell apart three times before it finally happened.◼️ How he found the company at a basketball game, from an owner who wasn't even looking to sell◼️ How he bought a business far bigger than he could afford, without an SBA loan or a bank, after pitching around 60 investors◼️ The $40,000 he paid out of his own pocket that exposed a problem big enough to change the entire price◼️ The night the deal collapsed at the signing table, and why he refused to walk away after it fell apart three times◼️ How the competitor he set out to beat ended up funding the deal and merging into his companySubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, I break down how Jay went from 25 years on Wall Street to owning a plant leasing business that's been running for nearly 40 years and pays him $650K a year.◼️ Why the biggest plants in a hotel lobby are rented and never sold, and how the same plant earns money at three different clients◼️ The 10% he put down on a $2M business, and where the other 90% came from◼️ Why a $500K business can be riskier to own than a $2M one◼️ How he beat six other buyers without offering the most money◼️ The profit hiding in the seller's books that the broker's numbers never showedSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Scott breaks down why he deliberately hunted businesses smaller than most searchers will touch, how he ran his entire search without leaving his job, and what it took to lift a decades-old repair company from single-digit margins to sixteen percent in his first year.◼️ The afternoon at his old job that made him accelerate a plan he had been sitting on for seven years◼️ How he ran a year-long search on nights and weekends, keeping his day job the whole time, with two kids under six at home◼️ Why every other buyer promised the sellers bigger numbers than he did, and how he won the deal anyway◼️ The employee situation two weeks after closing that ended with him needing a police escort to recover a company truck◼️ The two mistakes he says cost him most in year one, including the one he is still paying for every monthSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Christian breaks down how he bought a $1.2M-a-year business with only 5% down, what he found inside it that nobody disclosed, and how his first year as the owner actually went.◼️ How he got a $3.45M deal done with only 5% of the price in cash◼️ The six-figure Airbnb business he lost overnight, and why it pointed him straight at this deal◼️ The two things nobody told him about the company until after he already owned it◼️ The one question he'd ask every seller now, and why he never asked it◼️ The three-week vacation he took in his first year, and what his team did while he was goneSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Ryan breaks down how he bought a grant writing business in an industry he knew nothing about, got the seller to finance 80% of it, and doubled revenue a year later.◼️ Why the seller agreed to finance 80% of the price herself, and what she got in return◼️ The detail in the company's history that made him stop trying to talk himself out of the deal◼️ What happened two days before closing that nearly ended the whole thing◼️ How long it actually took him to feel competent in an industry he had never worked in◼️ The one thing he says he would do differently if he bought again this 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Ramsey breaks down why he bought a business he'd never shop in himself, how he got it financed after two banks turned him down, and what it takes to run it from another state.◼️ Why a business he would never walk into as a customer turned out to be the only one that cleared every number on his list◼️ How two banks turned him down over the category, and why he said no when the seller offered to finance the entire purchase◼️ The visit he made to the store as an ordinary customer before he ever bought it, and what he was watching for◼️ What running two stores from another state actually looks like, and why he says even when he's not there, he's there◼️ Why he still has not taken a single dollar out of the business, and the three-year plan that changes thatSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Mary breaks down how she went from a tech layoff to buying a $1.05 million medical billing business she knew nothing about, what her first year of ownership actually cost her, and how she has grown it 35% since taking over.◼️ Why she let the previous owner keep 10% of the company instead of buying him out completely◼️ The single client that made up too much of the revenue, and how she got a lender comfortable with it◼️ How the business went from signing three new clients a year to a dozen in fifteen months◼️ The one thing she skipped before closing that she would never skip again◼️ Whether AI is coming for medical billing, from someone who runs oneSubscribe to the SMB Deal Hunter newsletter (250,000+ subscribers): https://join.smbdealhunter.xyz/Follow Helen:Twitter: https://x.com/HelenGuo_LinkedIn: https://www.linkedin.com/in/helen-guo-06674523/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Jay breaks down why he walked away from a 25-year Wall Street career to buy a business that was already running, how he closed a $2M deal in about seven months, and what his first month as an owner actually taught him.◼️ Why he stopped building other people's wealth at a New York hedge fund and decided to own the whole thing himself◼️ How he found his business within a day of joining and beat six other buyers without hiring a lawyer to write his offer◼️ The add-backs he uncovered in diligence that pushed his multiple below 3x and lowered the price he paid◼️ How a deal that was 30% real estate cleared SBA financing and an environmental review without blowing the timeline◼️ What running a 40-year-old plant leasing business in 40 hours a week looks like with a 12-year manager on the day-to-daySubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Jay breaks down why he walked away from a 25-year Wall Street career to buy a business that was already running, how he closed a $2M deal in about seven months, and what his first month as an owner actually taught him.◼️ Why he stopped building other people's wealth at a New York hedge fund and decided to own the whole thing himself◼️ How he found his business within a day of joining and beat six other buyers without hiring a lawyer to write his offer◼️ The add-backs he uncovered in diligence that pushed his multiple below 3x and lowered the price he paid◼️ How a deal that was 30% real estate cleared SBA financing and an environmental review without blowing the timeline◼️ What running a 40-year-old plant leasing business in 40 hours a week looks like with a 12-year manager on the day-to-daySubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Evan Stewart breaks down how he searched for years without quitting his day job, bought a 30-year-old commercial printing business making $1.7M a year in profit, and grew it past $3M in an industry most people write off as dying.◼️ How he raised money from friends and family using a playbook from his political fundraising days (and the one question he used to cut his list)◼️ The last-minute demand from the bank that nearly killed the deal, and the move by the sellers that saved it◼️ Why he borrowed the absolute max the bank would give him for his first deal (he believes bigger is actually safer)◼️ What happened when he realized he was "the dumbest person in the building," and how working second shift won over his 70-person team◼️ The diligence mistake he regrets most: building model after model when he should have been studying the peopleSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Bailey breaks down why she stopped trusting Big Tech and bought a firm that's run since 1971, how she closed the $925K deal in six months without quitting her job, and what running it on 20 hours a week actually looks like.◼️ Why she stopped trusting "the tech billionaires" to keep her employed and bought a business instead◼️ How our team helped her kill the seller's balloon payment and land interest-only terms for the first two years◼️ The rival buyer she beat out, even though the seller thought he was too "spreadsheet focused"◼️ Why she drove her own car into a member's auto shop for an oil change, just to prove we weren't all "paid actors"◼️ What running a $450K-a-year business on 20 hours a week looks like when you still have a full-time jobSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Brian Seeling breaks down how he left a 15-year IT career, bought the very first business he ever looked at, and grew a boring commercial kitchen repair shop to almost $1.2M a quarter.◼️ Why the first business he ever saw on BizBuySell ended up being the one he bought◼️ The three separate times his deal fell apart before closing (and how he saved it each time)◼️ The fine print that doubled his down payment mid-deal◼️ How he's doubling revenue without chasing a single new customer◼️ The no-cap commission structure that keeps his techs from milking the clockSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, David breaks down why he left 15 years of VC-backed startups to buy a 28-year-old lawn care business, how he closed with $50K down and no bank after an SBA rule change killed his first deal, and what he's doing to grow a company that hadn't added a new client in a decade.◼️ Why a founder with an exit under his belt decided a lawn care business was the smarter bet◼️ How an SBA rule change killed his first deal 60 days into due diligence, and the pivot that got him to the closing table anyway◼️ The exact seller-financing structure behind a $179K close with $50K down and no bank or investors◼️ How he rode the routes and rebuilt the P&L by hand to make sure he wasn't buying "a complete wreck of a business"◼️ How a business that hadn't added a new client in 10 years is now adding 2 to 3 every weekSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Chris Edwards breaks down how he quit a comfy consultingjob in the middle of the pandemic, bought an overlooked flooring store withjust 10% down, and turned it into a 24x return in four years.◼️ How he turned just 10% down into a 24x return◼️ Why he bought a flooring store in an isolated mountain town that biggerbuyers wrote off◼️ The year-one "I thought I ruined my life" stretch, and what got him through it◼️ The unglamorous operator playbook that grew the bottom line, from rippingout a fax-and-paper system to bringing on offshore help◼️ Why he walked away at the top and is now building a flooring company from the ground up, funded by the proceeds and everything the first one taught himSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Alejandro Vega breaks down why he walked away from a six-figure tech sales career to buy a concrete coatings company, how he beat out more than 10 other buyers and got in for just 10% down, and what his first two months as an owner have actually looked like.◼️ Why his wife told him "you're the problem," and how that one conversation finally pushed him out of tech sales◼️ How he structured a seven-figure deal with a 15% seller note to get in for just 10% down◼️ The week-one mistake that nearly dried up his leads, and how he caught it before it cost him◼️ Why he chose concrete coatings over plumbing, HVAC, and even a crime scene cleanup business◼️ What his first two months actually looked like: installing the floors himself and door-knocking job sites for one-call closesSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn this episode, Ryan Murray breaks down how he left a corporate career to buy a $5.5 million blinds and shutters business, why he was confident enough to sign a nearly $5 million loan to do it, and the exact playbook he used to grow it more than 50% in three years.◼️ How he got comfortable putting everything he owned on the line for a nearly $5 million loan◼️ The way he reviewed the deal before signing that gave him the conviction to go all in◼️ Why he bought the building too, and ended up paying less than he would have in rent◼️ How a boring 30-year-old business hides a steady stream of repeat revenue most buyers walk right past◼️ The sales system he used to grow revenue from $3 million to $4.7 million without chasing new customersSubscribe 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/

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/

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/

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/

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/

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/

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/

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/

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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn 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 paymentSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn 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 teamSubscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn 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 W2Subscribe 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/

Want help buying a business? https://smbdealhunter.link/pro-ytIn 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 priceSubscribe 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/

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 oneSubscribe 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/

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/

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/

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.

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/

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

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

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 

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 

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 

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

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 

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 

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 

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

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

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

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

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

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 

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