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2015 Chicago Marathon. Mile 13. I’m flying—feeling like I could run forever. Heart surgery, back surgery, barely able to stand a decade before, and here I am crushing it. Then I see the sign: NOT ALMOST THERE. Everything changed. Heavy legs. Cramping. Mental breakdown. I barely finished what started as my best race ever. That sign broke me, but it also built me. Southside Chicago kid who studied for 15 seconds between building cars on the assembly line. Graduated in 5 years. Built companies. Sold two. 800 employees. Young father at 20 who figured it out as I went. I’ve spent 50+ episodes of Not Almost There interviewing experts, and now my cohost and I are diving deeper into the conversations that matter most. We dig into what it really takes—in business, branding, health, life. No fluff. Real talk about building something that matters while the clock’s ticking. Whether you’re running your first mile or your hundredth company, we’re here to help you go the distance. Because almost there isn’t good enough.
Episodes
19 hours ago
19 hours ago
You've got the idea. You've done the research. So why are you still waiting? Multi-exit founder breaks down the psychology that keeps most people stuck in the "someday" phase - and the exact questions he asks himself before taking the leap.
From validating passion over market size to why your first-year budget is probably wrong, this episode tackles the gap between wanting to start and actually starting. Plus: the brutal reality of letting go early employees, why fighting business problems makes them worse, and how to know when you're ready to risk it all.
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