My guest today is Ronnie Fieg, founder and CEO of Kith. At age 13, Ronnie started working at David Z., an iconic New York shoe store, where he sold Timberland boots to Jay-Z and Wallabies to Wu-Tang Clan. He worked his way up from the stockroom and earned his first collaboration in 2007, when he worked with ASICS on new Gel-Lyte 3s. That collection sold out ... Show More
Oct 6
Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443]
My guest today is Jesse Zhang. Jesse is the co-founder and CEO of Decagon, one of the fastest-growing AI customer service companies. Decagon provides a centralized AI engine to auto-resolve issues at any time, in every language, and across every channel. Jesse shares his systemat ... Show More
1h 21m
Sep 26
Rolex: Timeless Excellence - (Invest Like the Best, CLASSICS)
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. This Business Breakdowns on Rolex is a long-time stand out. The founder and executive chairman of Hodinkee, Ben Cl ... Show More
1h 2m
Mar 2025
How Tommy Mello Became a Billionaire Painting Garage Doors (And How He Shares the Wealth)
What does it take to turn a blue-collar business into a billion-dollar empire?For Tommy Mello, the answer is simple: relentless competition, strategic investing, and an unwavering commitment to winning. From painting garage doors to building A1 Garage Doors into a massive industr ... Show More
30m 47s
Nov 2023
29: The largest developer in LA, Rick Caruso
Rick Caruso’s real estate projects have defined how a generation of LA residents live in and experience the city. When you truly collaborate with communities, Rick explains, you get more than reliable financial success — you get momentum behind your project, you get political cap ... Show More
41m 50s
Mar 2024
'The $150,000 Coach' Shannon Graham & Four Loko Founder, Chris Hunter 💸 E61
Shannon Graham, founder of Astranaut, has dedicated himself to empowering individuals to lead fulfilling lives for over 20 years. He has started projects to help with video game addiction and to empower Hispanic immigrants financially. Shannon's teamed up with leaders all over th ... Show More
1h 10m
Feb 2025
"I Fast-Forwarded My Life 10 Years”: How Geo-Arbitrage 3X’d My Wealth and Changed My Life
What if you could fast-forward your financial goals by ten years just by moving abroad?
That’s exactly what entrepreneur Rob Hoffman did when he relocated to Colombia, where his $3M net worth stretches as if it’s $9M.
Rob, a member of the Hampton community, shares how he built a ... Show More
32m 6s
Sep 23
I Chose Fun Over Profit…. And I Regret It
Thinking about selling your company? 24 founders told us what really happens after the wire hits. — https://www.joinhampton.com/exit-reportJordan Schlipf spent a decade building companies optimized for fun, freedom, and friendships. But with years of hindsight, he wonders if he l ... Show More
37m 5s
Oct 5
#402 Thomas Peterffy: The $80 Billion Founder Who Automates Everything
I didn’t know who Thomas Peterffy was. I was shocked to learn that he is 81 years old, worth $80 billion dollars, and has built his $120 billion company, Interactive Brokers, into one of the most efficient companies in the world. I discovered Peterffy by reading this incredible p ... Show More
31m 57s
Feb 2025
Elon Musk's Acquisition Made Me $50M, But Fatherhood Redefined My Life
What if the key to success wasn’t grinding harder—but learning to let go?
Chris Bakke made 10s of millions selling two companies, including one to Elon Musk’s Twitter. But after years of chasing big wins, something changed: he had kids. And suddenly, the drive that once defined h ... Show More
46m 31s
Sep 11
$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder)
Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for ... Show More
1h 37m
Jan 2025
#212 Alfred Lin: How to Think (and Work) Like a World-Class Investor
Alfred Lin shares strategies for navigating startup challenges, building resilient teams, and creating long-lasting value. Lin explores lessons from companies like Zappos, Airbnb, DoorDash, and Amazon, offering actionable insights on topics like hiring for potential, managing cri ... Show More
2h 19m