EPISODE · Jul 24, 2026 · 39 MIN
How I Learned How To Win
from The Michael James Way · host Michael James
Michael hit rock bottom, no house, no money, living in a basement apartment with his kids, and bought a one-way ticket to San Francisco with no plan to get back except riding a bicycle across the country.In this episode, he breaks down the ice-fishing detour, the coach's warning about the five times you'll want to quit, and the cyclocross race that taught him how to actually win, and how every one of those lessons ended up rebuilding his business after 2008 nearly took it all.In this episode: why "burning the boat" (a $150 one-way ticket) forced a real commitment, the rule that got him through day 3 of a cross-country ride ("don't act on your emotions"), how studying a competitor's weaknesses won a race he'd already lost, and why knowing your numbers is the difference between planning for hard times and getting blindsided by them.
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How I Learned How To Win
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