What Are My Five-Year Plans?

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Timestamps

00:00 Intro

06:25 The night that changed everything (college brawl → jail)

12:48 “I saw scared racism for the first time”

19:40 I spent six months in jail — and then decided “I’m never coming back”

25:50 How the justice system traps you (and how he beat it)

35:47 200 job applications… and 200 rejections

40:12 “No one would hire me, so I hired myself”

46:33 The $3,000 house that changed his life

55:40 I lost $170,000 in Houston, it was a betrayal! (my blood was boiling!)

1:03:22 The birth of Goodies: How I turned a $1,000 truck into a $1M business

1:09:55 The SYSTEM that makes restaurants print money

1:22:58 How to find the hidden “opportunities” in any market

1:27:40 This 1 mindset made me successful

About the Guest / About the Episode

Dawon Matthews is the ultimate underdog, he went from being kicked out of college, jailed, and rejected from over 200 jobs to building a $1.2M food truck in 11 months. His story is a masterclass in resilience, reinvention, and building systems that scale This episode will shift how you think about adversity, opportunity, and what’s truly possible when you refuse to quit....Enjoy

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