What happens when your dream business nearly destroys you, and then teaches you everything you needed to know about money?
We don't usually talk about this. The early days. The subway rides hauling coffee beans across Chicago. The polar vortex brought us to the edge of bankruptcy. The moment we realized we'd been doing money completely wrong.
But Perry asked us to get real. So we did.
In Part 1 of this two-part conversation, we're pulling back the curtain on our entrepreneurial journey, from bootstrapping a coffee shop with zero financial backing to discovering the principles that would eventually reshape how we help business owners build wealth.
You'll hear:
- Why we delivered coffee beans on the subway before our shop even opened (and what that taught us about building a business with no money)
- The brutal wake-up call that came during a Chicago polar vortex—and the single lesson that saved everything
- What our financial planner told us contradicted everything we thought we knew about "saving for retirement."
- The three things every entrepreneur needs to survive (hint: passion isn't enough)
- Why we were told we were "too entrepreneurial" to get hired and how that rejection became our biggest opportunity
Key Quote: "We were naive about how hard it would be. But that naivety is also what kept us going when smarter people would have quit."
This isn't a polished success story. It's the real version—the good, the bad, and the ramen. If you've ever wondered whether you're cut out for this entrepreneur thing, or if you're doing money all wrong, this one's for you.
Coming next week: Part 2 dives into what's broken in the financial planning world and how we're using Profit First, Infinite Banking, and AI to help business owners build wealth differently.
Resources mentioned:
- Find Your Flow Quiz — 10 questions to discover your financial personality
- Financial Nervous System Diagnostic — A deeper 54-question assessment
- Get more info about Perry Marshall's Roundtable here.
- Profit Planning Network 2026 — Join our community of business owners building profitability and wealth
00:00 Introduction
00:45 The Coffee Shop Dream
03:20 Bootstrapping with Nothing
06:15 The Polar Vortex Wake-Up Call
09:30 Discovering Liquidity Over Retirement
11:45 The Three Things Every Entrepreneur Needs
13:00 Preview of Part 2
Watch on YouTube: https://youtu.be/bC5j2xh8y_g
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