Arguing for Prudence: Why I Wanted Cash Off the Table

Most people think failure is the end. I thought that too — until I got rejected from every Ivy League school, barely scraped into Arizona State, and watched my career implode over and over again. In this raw episode, I'm pulling back the curtain on every spectacular failure that built my empire: the boss who said I'd leave dead bodies behind to get ahead, the million-dollar payout to a bad partner, and the moment I almost lost everything with weeks of cash left.

From getting pushed out of companies to navigating a brutal divorce in front of my entire firm, these aren't just war stories — they're the blueprint for turning your biggest losses into your greatest wins. I share why the chip on your shoulder is worth more than a pat on the back, how to know when you're made of paper versus walls, and why your bank account is a direct reflection of the difficult conversations you're willing to have.

If you've ever felt like you're drowning while trying to look calm on the surface, or if you're tired of playing it safe while watching others win big, this episode will show you exactly why failure isn't just the entry price to success — it's the only currency that matters.

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00:00:00 Introduction 00:00:36 Welcome to the "Lowlight Reel" 00:00:59 College Rejection and the Arizona State Advantage 00:01:58 No Job Offers and the Vanguard Breakthrough 00:03:48 The Brutal Feedback at Vanguard 00:06:12 Breaking Into Goldman Sachs 00:07:50 Learning From Goldman's Elite 00:09:57 The State Street Hustle 00:11:52 First Time Firing Someone 00:15:52 Building a Billion Dollar Business 00:16:29 Divorce and Professional Attacks 00:18:18 Side Hustles During Corporate Drama 00:19:34 The CEO's Walking Warning 00:20:50 The Partnership Power Play 00:22:30 The Dinner Confrontation 00:25:27 Going Solo and Million Dollar Mistakes 00:28:06 Near Financial Collapse 00:30:49 Lessons on Failure and Growth

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