The SMB Deal Hunter Podcast

Helen Guo
  • 5.0 (7)
  • 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. 2D AGO

    This CPA made all the MAJOR mistakes so you don't have to | Rushi Amin

    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

    1h 3m
  2. How This Entrepreneur Bought a $1.3M Home Service Biz and Sold it to PE for $5.8M a Few MONTHS Later [Greatest Hits]

    FEB 13

    How This Entrepreneur Bought a $1.3M Home Service Biz and Sold it to PE for $5.8M a Few MONTHS Later [Greatest Hits]

    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

    53 min
  3. How This Serial Acquisition Entrepreneur Left His Corporate Career and Bought 10 Businesses

    FEB 6

    How This Serial Acquisition Entrepreneur Left His Corporate Career and Bought 10 Businesses

    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

    57 min
  4. [Greatest Hits] Buying an Accounting Firm Without Being a CPA? She Did It.

    JAN 30

    [Greatest Hits] Buying an Accounting Firm Without Being a CPA? She Did It.

    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

    49 min

  5. JAN 23

    McKinsey Consultant -> Two $1M+ Businesses in 2 years | Savanna Rush

    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 bigger Here'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

    59 min

  6. JAN 16

    He bought two $5M+ companies in 2 years (completely off market and with no investors)

    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 ready Here'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

    54 min

  7. JAN 9

    How to stand out with brokers and win competitive deals with Alejandra Barrera

    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

    1h 7m

  8. 12/19/2025

    How These 2 Partners Met on Craigslist & Ended Up Buying 15 Companies Together | Joe Van Deman and Colin King

    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

    1h 6m
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5
out of 5
7 Ratings

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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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