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 tell a different story. Teams are being treated as highly leverageable assets and anchor tenants for much larger business machines built around arenas, real estate, and media rights.

From there, the episode maps out the new owner archetypes: tech and industry giants like Steve Ballmer running franchises like data-driven startups; hedge fund titans treating teams as unique, slow-moving assets inside much bigger portfolios; and pure private equity groups built to buy, restructure, lever up, and eventually exit.

Listeners get a guided tour through marquee examples—from the $6 billion sale of the Washington Commanders to Guggenheim’s LA Dodgers and the wave of U.S. PE money flooding into European soccer—showing how financial logic is reshaping decisions on and off the field.

The lens then shifts to performance, where the story gets uncomfortable. Big money sometimes delivers big winning: the Clippers’ sustained relevance under Ballmer, the Lightning’s back-to-back Stanley Cups, the Bucks’ title run, the Rams winning a Super Bowl in a $5 billion stadium, and Manchester City’s serial dominance. But right next to those cases are the strategic tanks and slow burns.

The Wizards’ historically bad 15–67 season is unpacked as a case study in “productive” losing—shedding contracts, loading up on youth, and aiming for a franchise-altering draft asset—alongside academic work showing PE-owned clubs abroad often cut into the very departments that support long-term success.

The episode then zooms out to the platform play: billion-dollar arena overhauls, team-controlled entertainment districts, and owners quietly buying or building the regional sports networks that broadcast their own games. Monumental’s simultaneous arena megaproject, RSN acquisition, and Wizards/Capitals split strategy becomes the clearest example of how one ownership group can tank with one asset while going all-in with another in the same building.

Listeners see how the real profit centers increasingly sit around the team—premium suites, naming rights, year-round events, media inventory, and land value—while the roster becomes one variable inside a much larger model.

The episode closes on the uncomfortable but honest diagnosis. Modern owners are wearing two hats at once: media/real estate mogul and traditional sports owner. Sometimes those roles align, and championships become the best way to maximize asset value. Other times, the balance sheet wins out over the scoreboard in the short term, and “failing” seasons look more like deliberate depreciation to secure a future star or a better financing deal.

The hard question the episode leaves you with is simple: in this new era, when your team bottoms out or builds a palace, are you watching bad management—or a very intentional strategy playing out on a longer timeline than the season schedule?

CHAPTERS
(00:00) From status symbol to financial asset
(02:00) Meet the new owners: tech, hedge funds, PE
(04:00) Global capital and changing league rules
(06:00) When big money actually buys winning
(08:00) Strategic losing and the Wizards tank
(10:00) PE playbooks and performance declines
(12:00) Arenas, real estate, and year-round revenue
(14:00) Owning the media and RSN safety nets
(16:00) Two strategies: tanking vs trophies
(20:00) Does the balance sheet now define “winning”?

Connect with Michael Wildes

⁠⁠mikewildes.com⁠⁠

LinkedIn: ⁠⁠Michael Wildes⁠⁠

X: ⁠⁠@Captainwildes⁠⁠

YouTube: ⁠⁠@MichaelMJWildes

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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 uses it as the entry point to dissect how the company that became a verb is increasingly the second choice.

From there, the episode breaks down the three big cuts that redefined the landscape: Canva, Figma, and Riverside.fm. Canva didn’t beat Photoshop and Illustrator on feature depth; it beat Adobe on distribution, friction, and templates. Figma didn’t just add collaboration as a feature; it rebuilt design as a multiplayer, browser-native, team sport—and forced Adobe into a $20B panic bid regulators eventually blocked. Riverside did to remote production what those tools did to design: it removed pain, automated the promo layer, and turned high-quality podcast and video workflows into something anyone could scale.

The lens then zooms out to show the broader siege: CapCut owning mobile-native, viral editing; Descript letting people edit video the way they edit documents; AI-native tools attacking After Effects-style work with text-to-video, instant rotoscoping, and automated compositing. What emerges is not a story of one rival crushing Adobe, but of dozens of specialized tools each stealing a slice of habit, budget, and mindshare—one workflow at a time.

The episode closes on the cultural diagnosis. Adobe’s business model and internal incentives still lean toward bundles, enterprise sales, and protecting legacy revenue, while the challengers build for the human first, procurement last. Listeners walk away with four hard lessons: product is marketing, speed beats legacy, workflow beats feature depth, and culture is code. The real long-term risk is not that people ask “Is Adobe dead?” It’s that an entire generation grows up asking “Adobe who?”

(02:25) Cut #1 – Canva and the end of design gatekeeping

(05:24) Templates, utility design, and browser-native distribution

(06:16) Cut #2 – Figma and the rise of multiplayer design

(08:40) Students, free tiers, and the generational shift in tools

(09:35) Adobe’s $20B Figma bid and regulatory block

(11:04) Cut #3 – Riverside and the remote studio in a browser

(13:47) Local recording, AI Magic Clips, and PLG in media workflows

(16:08) The wider siege: stock signals, CapCut, and mobile-native editing

(18:16) Descript and editing video like a Google Doc

(19:13) AI video tools vs. After Effects: 8 hours down to 8 seconds

(20:26) Pitch, Notion, and the erosion of InDesign’s territory

(21:17) Who Adobe really builds for: pros, procurement, and ARR

(22:43) The culture gap: lawyers and accountants vs. product and users

(23:46) Lesson 1–2: Product is marketing; speed beats legacy

(24:35) Lesson 3–4: Workflow wins; culture is code

(26:22) Adobe’s slow bleed and the risk of becoming “Adobe who?”

Connect with Michael Wildes

⁠mikewildes.com⁠

LinkedIn: ⁠Michael Wildes⁠

X: ⁠@Captainwildes⁠

YouTube: ⁠@MichaelMJWildes

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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.

The discussion begins with the core decision to self-insure and what it really means to “be your own insurance company.” The hosts break down why this is only rational once you can comfortably write a seven-figure medical check without blinking, why the true threshold often sits in the $50M–$100M liquid net worth range, and how family offices carve out dedicated healthcare funds and trusts so a $3M cancer protocol never disrupts the core portfolio.

From there, the episode maps out the service stack the wealthy build on top: concierge medicine and direct primary care as the access layer, high-deductible health plans as catastrophic stop-loss and discount engines, and aggressive negotiation of cash prices that can cut hospital bills by 10–50%. Listeners learn how HSAs, Section 105 plans, HRAs, and even captive insurance companies are used to convert healthcare from an after-tax personal cost into a pre-tax, tax-advantaged, or tax-deferred spend.

The conversation then zooms out to the operational reality: family offices acting as 24/7 “health command centers,” global medical Rolodexes, executive physicals at institutions like Mayo and Cleveland Clinic, telemedicine-driven global concierge services, medical evacuations, and even private physicians on payroll traveling with the family. The episode closes on the hard question: what does it mean for equity and the future of healthcare when the ability to bypass constraints and command global excellence on demand is increasingly a function of balance sheet size?

CHAPTERS

(00:00) Constraints of US healthcare

(02:20) Self-insuring when you’re rich

(05:15) Wealth thresholds for self-insurance

(07:20) Cash pay and negotiation power

(08:59) Concierge vs direct primary care

(15:18) Catastrophic HDHP strategy

(21:54) HSAs as wealth tools

(26:08) Section 105 and HRAs

(28:05) Captive insurance for families

(30:49) Trusts, HEMS, asset protection

(32:40) Family office as health HQ

(35:20) Executive checkups and clinics

(39:03) Philanthropy and access

(40:39) Doctors on private payroll

(42:25) When insurance math flips

(48:34) Parallel systems and equity

Connect with Michael Wildes

⁠mikewildes.com⁠

LinkedIn: ⁠Michael Wildes⁠

X: ⁠@Captainwildes⁠

YouTube: ⁠@MichaelMJWildes

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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. Audiences are overloaded, advertisers are frustrated, and the old playbook of counting followers or measuring reach no longer works. The hosts follow the data trail, revealing how metrics once treated as gold standards have lost credibility, and how brands are rewriting the rules to focus on authenticity, measurable trust, and real-world results.

Through research and case studies, the episode explains how marketing has evolved from a volume game to a value game. It outlines the collapse of engagement fraud — bots, purchased followers, and artificial likes — and details how brands now demand hard ROI metrics such as ROAS, CPA, LTV, and conversion per follower (CPF). The conversation highlights why smaller, trusted creators often outperform massive influencers and how transparency, credibility, and audience belief have become the ultimate differentiators.

Listeners also learn how the new “Modern Metrics Toolkit” works — analyzing comment authenticity, sentiment scores, saves, shares, brand lift, and Net Promoter Scores to quantify trust in action. The episode dives into how performance-based contracts, retention metrics, and brand sentiment tracking are redefining success across industries — from fast-moving DTC brands and fashion to long-cycle B2B deals.

CHAPTERS

00:00 The Economy of Attention

03:05 The Breakdown of Vanity Metrics

05:59 The Shift to Trust as a KPI

09:06 Measuring Trust and Influence

12:07 The Modern Metrics Toolkit

15:04 Engagement Quality and High-Intent Actions

18:00 Conversion Rates and Performance Metrics

21:09 Long-Term Relationships and Customer Loyalty

24:11 Brand Sentiment and Advocacy

27:03 Industry-Specific Metrics

30:06 The Future of Trust in Marketing

Connect with Michael Wildes

mikewildes.com

LinkedIn: Michael Wildes

X: @Captainwildes

YouTube: @MichaelMJWildes

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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 wealth from studios to individuals, how creators like MrBeast, Dhar Mann, and Kinigra Deon are building full-scale production studios from scratch, and why Hollywood’s last remaining stronghold—live sports—is falling next. We’ll also examine Netflix’s counter-move, its new partnership with Spotify, and what it says about a streaming war no longer fought over content, but over creators.

The real story isn’t about disruption—it’s about redistribution.

The episode breaks down the economics behind YouTube’s $36 billion in ad revenue, $32 billion in annual creator payouts, and the platform’s 13 percent share of all U.S. TV screen time. We explore how this money flow is turning creators into businesses, businesses into networks, and networks into the new studios of our time.

YouTube’s story is no longer about clicks or virality—it’s about the reindustrialization of storytelling, where anyone with a camera and conviction can compete with the biggest names in media. The creator economy isn’t a trend. It’s the new television.

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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 story behind Coplan’s rise—from FBI raids and regulatory shutdowns to becoming the youngest self-made billionaire in America. His story isn’t just about innovation; it’s about understanding how the modern wealth ladder actually works.

You’ll hear how Coplan turned academic theory into a market-moving platform, how he navigated compliance by recruiting former regulators, and how his network—spanning Wall Street, Silicon Valley, and Hollywood—became his ultimate moat.

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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 look at the data behind the shift, from rising 1099 filings to falling wage security, and hear the real stories behind the statistics: Maria in retail and rideshare, Jamal in security and IT, and Carla balancing office work with weekend catering.

We unpack how inflation, credit rates, and unstable schedules have made side income essential—and how this new class of workers has learned to treat time like money. They plan their weeks like businesses: tracking margins, protecting sleep, and managing taxes on every dollar.

The takeaway is clear: the side hustle isn’t on the side anymore. It’s the scaffolding holding the middle class together.

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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 core sectors—Business, Aviation, Media, and Philanthropy.

Rather than buying and flipping assets, we launch ventures in‑house, scale them with a shared operating system, and hold them indefinitely.

Strategic venture investments and precision bolt‑ons give each platform an extra surge when it counts, but the compounding value comes from the continuous momentum we create and maintain.

As for the show, we’re living in arguably the most exciting time in history. As Charles Dickens said, this is the best of times. It might be the worst, too—but I’m focused squarely on the upside.

It feels like we’re living through multiple industrial revolutions at once—technology, energy, space travel, media, entertainment, policy—you name it.

I launched Drive Phase to sit at the convergence of these trends, and I want to share what I’m seeing, hearing, and thinking—the headlines, the stories, the signals—the inside track on how we really work, live, and build what’s next.

For us, the most interesting things happen where industries collide because life doesn’t happen in silos, and neither will the future.

Dickens also said, “It was the age of wisdom, and it was the age of foolishness.” It’s easy to get it wrong. Amid all the signals, there is plenty of noise. We want to help you cut through that.

So, welcome to The Inside Track.

Brought to you by ⁠The Wave⁠ on ⁠The Frequency Network⁠.

More About Michael Wildes
Explore the work of ⁠Michael Wildes⁠—entrepreneur, strategist, pilot, and founder of Drive Phase, a permanent capital company operating at the intersection of media, aviation, business, and philanthropy.

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Produced by ⁠Massif Studio & Production⁠ and ⁠The Tallawah Group⁠.

⁠Massif Studio Website⁠

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For sponsorship inquiries, contact: ⁠[email protected]⁠

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