The Steve Weiss Journey

His parents thought he'd lost his mind. Zach Goldstein had spent six years building a career in finance — the safe path, the one his family understood — when he quit to sell sweatpants. He had zero apparel experience, zero manufacturing contacts, and exactly one conviction: that men deserved pants that actually fit. He spent 18 months perfecting a single product before launching a Kickstarter...

Rafael Vivas's dad told him the internet was a fad. Then kicked him out of the house for believing otherwise. Rafael was 18 years old — no degree, no safety net, no plan B — when he walked into a startup nobody had heard of and took a bet most people wouldn't have taken at twice the age. He told himself he would die before he let it fail. That startup was AppLovin. Today it's worth ove...

He was running a nightclub empire when 2008 hit. Checked himself into rehab. Nearly filed for personal bankruptcy. Then he co-founded a juice company in a San Diego kitchen — and scaled it to nearly $100M in revenue. But the real story starts after that. Coca-Cola and Goldman Sachs bought 49% of Suja Juice with a promise to acquire the rest. They met the employees. They started transition plans. T...

Most business owners think they understand how private equity works. They don't. A $1M EBITDA business sells at a 2x multiple. A $10M EBITDA business sells at a 10x multiple. That gap isn't random — it's the system. And if you don't know how it works before you walk into a deal, you're already losing. In this episode, Chapin Newhard — founder of 48 North Partners and a former P...

Blake Mycoskie built TOMS Shoes from a vacation idea into a global movement — 100 million pairs of shoes given away, a company worth hundreds of millions, and a name that redefined what business could be. Then he sold it. And nearly lost everything inside. For almost seven years after the exit, Blake quietly fell apart. No company. No community. No identity. What looked like freedom was actually e...

O'Shea Jackson Jr. had one shot to play his father, Ice Cube, in Straight Outta Compton. In this episode, O'Shea opens up about the crushing pressure of the "Legacy," the moment he thought it was all over, and what his dad never actually asked him to do. What you'll hear: The grueling audition process for Straight Outta Compton Why he felt like he was "ruining his life&q...

Most entrepreneurs talk about the "win." Lauren Kleinman talks about the trade-offs. From her early days in import-export to leading marketing at Ritual and Scopely, Lauren has been at the center of some of the fastest-growing brands in the world. Now, she's the co-founder of Dreamday and Quality Media, where she’s pioneered a new category: Performance PR. In this episode, we go beyo...

From the streets to a prison cell, Quan Huynh's life took a dramatic turn at just 17 when he was convicted for conspiracy to commit a crime. But that was just the beginning of a darker path that led him to a 15-years-to-life sentence for second-degree murder. For over two decades, Quan navigated the brutal realities of California's toughest prisons, initially embracing a life of crime behind bars....

Is SEO dead? John Zacharias, founder of Grow Marketing, believes the future is "GEO"—Generative Engine Optimization. In this deep dive, we explore how marketing is shifting from Google to ChatGPT and why your old strategies won't work in the AI era. But this isn't just about business; John opens up about his journey from rehab to building a massive agency, and the "emptiness...

Most financial advisors are salespeople in disguise. Gabriel Shaheen, CEO of Falcon Wealth Planning, breaks down the massive difference between "Fee-Based" and "Fee-Only" advisors and why that distinction could save your retirement. We dive deep into tax planning strategies, why he often advises against standard diversification, and the psychological struggle entrepreneurs face when selling their...

While I was away, my house manager Juan stayed behind in the middle of the Palisades firestorm to protect my home and our neighbors. With no water in the hydrants and firefighters overwhelmed, Juan used pool water, buckets, and sheer grit to fight off the flames.