In this episode, I sit down with Dan Young, who went from juvenile detention to building multiple computer hardware empires and closing over $600 million in property deals. Dan shares his unconventional path from selling Ginsu knives at swap meets to founding PC Laptops and Xydax PCs, plus the investment strategies that built his wealth.

A deep dive into Tiliter, a computer vision startup that began by scanning produce in grocery stores and is now expanding globally. This article explores founder Marcel Hirsch's journey from welding steel prototypes in a garage to deploying systems in hundreds of stores worldwide, the technical and business challenges of hardware startups, why investors initially rejected retail hardware, and the company's vision for democratizing computer vision technology beyond groceries.

Brian Clayton built and sold a $10 million landscaping company, then bootstrapped GreenPal to over $20 million in annual revenue without venture capital. This is the story of two successful companies, the brutal first five years of building a marketplace, and why he locked away his exit money to force his second startup to succeed on its own.

Jason and Pili Yarusi went from bartending on a rusty barge in New York City to controlling over 1,000 apartment units worth approximately $75 million. This is the story of how they made that journey, the lessons they learned from every job they held, why they abandoned flipping and wholesaling despite making money, and how they convinced investors to trust them with millions of dollars despite having zero large multifamily experience. They break down the actual numbers behind buying apartment complexes, explain why bigger properties are actually less risky than small ones, and reveal how they manage a massive portfolio with just one employee.

In this episode, I sit down with Nathan Barry, founder and CEO of ConvertKit, to trace his journey from teenage web designer to running a $28M email marketing platform. Nathan shares the exact strategies that took ConvertKit from $2,000 to $500,000 in monthly revenue, why he deliberately chose not to raise venture capital, and how he's building a company optimized for the journey, not just the exit.

Professional poker player Jonathan Little turned $50 into $350,000 by age 21, then built a multi-7-figure coaching empire. His secret? Obsessive study, ruthless game selection, and treating poker like a business—not a gamble.

Elizabeth Yin spent a few days at Tony Hsieh's startup as a high schooler, sold her own company to BuySellAds, and now runs one of the earliest-stage VC funds in existence. Here's how she invests in companies before they have revenue—and why that's actually less risky than you think.

Jennifer Beck built a cannabis wholesale marketplace, sold it for seven figures during a penny stock IPO, and then launched a CBD skincare line—all while navigating an industry where you can't advertise, can't process payments, and can't even hire a courier. Here's how she did it.

Greg Smith quit a lucrative law career to build online courses in 2005—when nobody knew what that meant. Sixteen years later, his company Thinkific went public at a $1.36 billion valuation. This is the messy, unglamorous story of how he got there.

Chris Bakke has cracked the code on strategic exits. He's sold companies for 80-90x revenue—not because of massive growth, but because of who was already at the table. Here's how he turned investor relationships into eight-figure acquisitions.