The Inside Track with Michael Wildes

This episode dives into a question fans are asking more and more quietly in the stands and loudly online: when a private equity firm or hedge fund buys your hometown team, what are they really trying to win—championships or spreadsheets? For decades, owning a pro franchise was framed as the ultimate vanity purchase, a civic duty for rich locals who wanted a trophy and a skybox. Now, the numbers te...

This episode dives into a question creative teams have started asking out loud: “Is Adobe dead?” Not in the literal, balance-sheet sense—Adobe is still a giant—but in the sense that really matters now: default status, cultural relevance, and ownership of the everyday creative workflow. The conversation starts with that moment on a Canva call when a client bluntly asks whether Adobe is over, and us...

This episode explores a parallel healthcare system that most people never see—the world where high- and ultra-high-net-worth individuals quietly step outside traditional insurance and build their own bespoke medical infrastructure. Instead of battling networks, pre-approvals, and deductibles, they self-insure, pay cash, and treat healthcare like a strategic asset rather than a reactive expense. Th...

This episode explores one of the most profound shifts happening in marketing and media today — the collapse of traditional vanity metrics like likes, views, and impressions, and the rise of trust as the defining measure of influence. The discussion begins by unpacking the saturation of the digital world — endless content, AI-generated posts, and consumer fatigue leading to widespread skepticism. A...

YouTube just ate television—and it’s still hungry. In this episode, we unpack how the world’s largest video platform quietly became the most powerful media network on Earth. What started as cat videos and vlogs has evolved into a $100 billion creator economy—one that’s now rewriting the rules of sports, entertainment, and storytelling itself. You’ll hear how YouTube’s payout model is shifting weal...

This podcast first existed as a newsletter. Read it here. When 27-year-old Shayne Coplan sold his belongings to pay rent, no one imagined he’d one day be sitting across from the CEO of the New York Stock Exchange, closing a $9 billion deal. But that’s exactly what happened when ICE—the parent company of the NYSE—invested $2 billion into his company, Polymarket. In this episode, we unpack the real...

This podcast first existed as a newsletter. Read it here. More Americans need multiple jobs just to stay afloat. What used to be a “side hustle” has quietly become a second paycheck, a safety net, and for millions—a way to survive when one full-time income no longer covers the basics. In this episode, we break down how the old social contract—one job, one income, one safety net—has unraveled. We l...

Welcome to the Inside Track. My Name is Michael Wildes, Founder and CEO of Drive Phase Holding Co. I’m producing The Inside Track because I’m fascinated by how the world around us is shifting: how people work, live, and build the future. It's also the flagship show for Drive Phase. Drive Phase is a permanent‑capital firm dedicated to building the next generation of enduring companies across five c...