🎙️They Met on Craigslist & Ended Up Acquiring 15 Businesses Together | Joe Van Deman and Colin King

Hello SMB Deal Hunters!

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)

It was 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, they had to fill in regularly. 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 instead of 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 are some interesting stories we tackle during the interview...

🔥 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

👉 Dive into the story with Joe and Colin

Here’s a sneak peek into how hectic things were during their first acquisition:

And for our audio-only listeners, jump in and listen on Spotify or Apple Podcasts!

Alumni Spotlight

For those who missed it, we also did an SMB Deal Hunter Pro case study breaking down Mary’s acquisition of a $1M medical billing company that we helped her find and acquire completely off-market.

She did all of that within 10 months of joining the program.

Before jumping into the world of business buying, Mary spent 12+ years in tech as a UX Researcher at major companies like Pinterest and LinkedIn.

She started off where a lot of you are right now.

In the case study, we dive into…

✅ The 3 due diligence hurdles we helped her overcome (including a silent partner she didn’t know about)

✅ The complicated deal structure that led to her keeping the seller on for 10% of the business (with a buyout clause)

✅ The reality of life in the first 90 days into an acquisition (and how she managed it)

And here’s what she had to say when we asked her about her experience:

So, if you want me and my team to work with you to find, finance, and acquire a million-dollar cash-flowing business in the next 6-12 months, you might be interested in the Pro program.

👉️ Learn more and book a call

P.S. We’re going to be raising prices on Jan. 1st. We’ve spent the last year…

• Helping our members close over $115MM in deals

• Doubling the number of M&A advisors every Pro member has 1:1 access to

• Building an off-market marketplace with hundreds of listings no one else can access (more added every week)

So, if you have been dragging your feet…

👉️ Book a call and lock in your rate (even if you don’t plan on starting till next year. We can hold your spot!)

COMMUNITY PERKS

• Ready to buy and operate a $1M+ business? Get expert help at every step.

• Want to invest passively in SMB acquisitions? Get access to investment opportunities.

• Get a personal introduction to my preferred SBA 7(a) lender, non-SBA lenders, Quality of Earnings providers, or legal counsel

• Raising capital for your deal? I’ll connect you with investors from the SMB Deal Hunter Community.

• Interested in selling your business? I’ll help you connect with buyers from the SMB Deal Hunter Community.

THAT’S A WRAP

Want me to interview you for my podcast? Hit reply.

See you next week with some new deals!

-Helen Guo
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Disclaimer

This publication is a newsletter only and the information provided herein is the opinion of our editors and writers only. Any transaction or opportunity of any kind is provided for information only; SMB Deal Hunter does not verify nor confirm information. SMB Deal Hunter is not making any offer to readers to participate in any transaction or opportunity described herein.