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 ownersâŠtwo 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...
đ„ The 11:30pm Denny's interviews that helped them find their first real operator
đ„ How they flipped that nightmare first business to a PE firm in 18 months
đ„ The "two filters" they now run every deal through before buying
đ„ A story involving train tracks that explains why they tell people to work in a small business before buying one
