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This week, Jake and I sat down with Michael Gursha—co-founder of Rookie Road and CEO of Point Curve—to talk about what it means to own content in a world that’s being overtaken by AI.Mike’s team has quietly built a network of 13 media brands across niche verticals, powered by custom-built infrastructure and original content. In this episode, we unpack how Rookie Road scaled from a football explainer to a sports encyclopedia, why Mike thinks original content will become even more valuable in the GenAI era, and how his team is monetizing everything from ad revenue to commerce to potential tech licensing.Whether you’re a content creator, a media operator, or just curious about the future of publishing, this episode is for you.⏱️ TIMESTAMPS:00:00 — Intro00:45 — How Rookie Road started at Michigan03:43 — Early traction and what made it work06:14 — Growth through replication and SEO08:26 — The mechanics of viral web traffic11:18 — How Point Curve is evolving in the AI era15:19 — Why original content still matters24:45 — The shift from Rookie Road to Point Curve29:54 — Building 13 digital brands from scratch31:01 — Monetization: ads, affiliate, commerce, licensing34:43 — The potential to license their CMS and infrastructure38:22 — Checklist for launching a new content brand41:33 — Where the biggest growth opportunity lies44:31 — Outro + Recap with Jake and Tyler
Frank Michael Smith has built one of the biggest audiences in sports content—over 3 million followers, 2 billion views, and major partnerships with brands like Underdog and PointsBet. But this fall, he’s betting on something entirely new: Solo Survivor, a live, elimination-style fantasy game that blends sports, trivia, and real-time payouts.In this episode, Jake and Tyler sit down with Frank to unpack why he walked away from lucrative brand deals, how he’s using content to scale a real product, and what his leap into tech says about the next phase of the creator economy.Whether you're building in sports, media, or tech, this conversation is a blueprint for what creator-led businesses can look like at scale.00:00 – Intro00:39 – What is Solo Survivor?01:30 – Why Survivor Format?02:11 – Frank’s Fantasy Sports Start04:07 – Lessons from Brand Deals06:27 – Creator Value Gap07:05 – Launching Five Card Draw08:26 – Solo Survivor Business Model10:25 – Launch Surprises12:28 – Why Big Platforms Haven’t Done This14:47 – First-Mover Advantage17:30 – Content as Growth Engine18:50 – Viral Event Ideas20:51 – Balancing Brand and Business22:03 – Monetization as a Creator24:15 – Why Build Something Bigger25:28 – The 30K User Goal26:26 – What Has to Work27:37 – Exit Strategy28:55 – IP and Watch Parties31:51 – Recap
Basketball hasn’t changed its playing surface in over 100 years. ASB GlassFloor wants to change that.This week, Jake and Tyler talk with Chris Thornton, President of ASB GlassFloor Americas, about the rise of LED-powered glass courts and what they could mean for the future of the game.Already used at the NBA All-Star Game and in professional leagues across Europe, ASB’s surface is softer on players' joints, unlocks new digital revenue, and allows for full court customization at the push of a button.Chris explains how it works, why athletes are already preferring it over hardwood, and what it'll take to make glass floors the new standard in arenas across North America.00:00 – Intro00:42 – What ASB GlassFloor actually is03:22 – How it’s made and why it was developed06:30 – Why players prefer it over hardwood09:17 – Installation, cost, and durability12:23 – How the floor generates new revenue14:43 – The challenge of pricing new inventory17:25 – Sensors, ShotTracker, and performance data20:03 – What’s holding adoption back21:46 – Targeting different markets (pro, college, high school)24:13 – Customization and usability for coaches26:55 – Selling to multiple stakeholders28:20 – Will fans reject more in-game advertising?30:39 – Fan engagement potential and personalized courts32:13 – Adjusting brightness and visual distraction concerns34:48 – Feedback and crazy designs from players35:26 – Education and experiential learning use cases38:18 – Jake & Tyler recap: Will this replace hardwood?41:26 – Cost comparison and long-term value43:09 – Final thoughts on adoption and monetization strategy46:57 – Outro + Bottom of the Ninth plug
This week on Sportonomics, I sat down with Sam Berman, Head of Brand at Underdog, to unpack one of the boldest activations we’ve seen in the sports betting space.As sportsbooks fight for market share, Underdog is going a different route—ditching promos in favor of personality. Their latest stunt? Two 8.5-foot “Portals” dropped into Norman and Ann Arbor ahead of Oklahoma–Michigan, letting rival fans talk smack in real-time.We recorded this episode before the activation went live, so you'll hear us talk about it in future tense—but now that it’s happened, the strategy behind it is even more relevant.Sam breaks down how Underdog approaches culture-first marketing, how they think about creators, and why they want to be more like Red Bull than FanDuel.⏱️ TIMESTAMPS:00:00 – Intro01:05 – What the Portal is and why it matters02:25 – Building the installation and fan interaction03:33 – How long it took to pull off04:00 – Legal concerns and NSFW risks05:25 – Risk vs. reward: avoiding a flop06:41 – Why virality > conversion08:47 – How they’ll measure success09:39 – What other brands can learn from this11:47 – Defining Underdog’s target audience13:25 – Letting creators run with the idea14:42 – From CPA deals to brand lifts17:00 – Staying nimble as the company scales18:28 – Internal motto: “Give a sh*t”19:32 – The wildest ideas that didn’t get approved21:31 – Red Bull as a brand model22:41 – Planning for unplanned activations24:16 – The evolving focus: acquisition vs. retention26:17 – Brand awareness gaps and growth27:24 – Sam’s litmus test for good marketing ideas28:25 – Staying relevant as you age out29:46 – What happens if the Portal flops?31:44 – Why the activation had a high floor32:23 – Other stunts that worked33:08 – Final Portal pitch
Pro volleyball is booming—but the pro game hasn’t caught up.College matches are drawing millions of viewers, participation is surging, and cities like Omaha are packing stadiums. But until recently, the pro side of the sport was fractured and underfunded.That changed with the $325M merger between PVF and Major League Volleyball.This week, Jake and Tyler called up Abby Benton—a volleyball content creator and one of the sport’s most trusted voices—to break down the merger, the business model behind each league, and what needs to happen for pro volleyball to finally break through.⏱️ TIMESTAMPS00:00 – Intro01:02 – The 3-league pro volleyball landscape03:22 – Beach vs. indoor volleyball explained04:24 – Which league model has the most upside?06:07 – Why Omaha forced the merger09:36 – The truth about the PVF–MLV “merger”10:24 – Fan sentiment and why it’s a net positive12:39 – No men’s league = no direct comparison14:30 – Why pro hasn’t caught up with college15:32 – Which leagues are worth copying?17:06 – Building a fanbase around youth markets18:30 – Is expanding to 16 teams too fast?19:12 – What life is like for a pro volleyball player22:29 – Who’s funding the league?24:49 – Why volleyball has a media problem26:56 – How leagues can support creators28:08 – What has to happen by 202829:20 – Who’s volleyball’s Caitlin Clark?31:11 – What games to watch and where to follow Abby32:43 – Recap with Tyler and Jake
Jack Settleman isn’t just making content around college football—he’s investing in it.This fall, he’s spending $250,000 to embed Snapback Sports into the college football season, with creator-led partnerships, game-day content, and a bold $100,000 jersey patch offer.Jake and Tyler sat down with Jack to talk about the future of creator brands in sports, how schools are pricing attention, and what it takes to bet on yourself when there’s a deadline attached.⏱️ TIMESTAMPS00:00 – Intro00:02 – The $100K jersey patch pitch03:00 – Legal hurdles and NCAA approval04:10 – Valuing attention vs. media impressions06:00 – Alternate monetization ideas: helmet stickers, Player of the Game08:06 – Working with schools (and agencies) that “get it”10:12 – Why the jersey patch is just the start12:25 – Building relationships with schools and conferences14:45 – Why Snapback makes social-native content17:04 – DMing fans and listening without losing your vision19:27 – Snapback’s $250K fall content budget21:10 – No direct ROI, but a long-term vision24:48 – Why sustainable content matters26:45 – Building a team and letting go of control28:50 – The stress of staying in the game30:12 – Budgeting without guaranteed revenue32:34 – Runway pressure and April 2027 deadline35:18 – Creator identity, performance, and mental toll37:32 – YouTube monetization in real numbers39:19 – Why creators should be funded like startups40:26 – Snapback x Underdog: a long-term partnership44:11 – Understanding brand value and indirect ROI45:12 – Equity deals and what creators should know47:20 – Why transparency matters50:05 – The reality of creator equity: big upside, no liquidity51:04 – Recap with Jake and Tyler
Tommy John surgeries are up 170%. Pitchers are spending 2x more days on the IL than 15 years ago. And 50% of youth arms report pain during the season.This week, Jake and Tyler sit down with Jason Colleran, biomechanics expert and founder of Kinetic Arm, to break down the root causes of baseball’s injury epidemic—and why the coaching ecosystem isn’t equipped to stop it.Jason explains how his patented sleeve reduces elbow torque by ~30%, why most training programs are misguided, and how the next wave of performance gear can keep athletes healthy longer.⏱️ TIMESTAMPS00:00 — Intro00:52 — Why Jason built a product instead of training athletes03:50 — What Kinetic Arm is and how it works07:09 — Youth injuries and the travel ball incentive problem10:05 — Arm injury data and MLB’s negligence14:36 — Why common coaching practices are making things worse20:49 — Should Kinetic Arm be worn during games?22:27 — Is it a performance tool or just protective?26:54 — What Jason would change if he ran all of baseball30:01 — Simple ideas that work don’t sell—why the market is broken33:06 — How to win over old-school skeptics37:53 — Which MLB players are already wearing Kinetic Arm43:16 — Jason on proof, reviews, and public perception49:19 — Expanding beyond baseball and into other sports51:50 — Jason’s parting thoughts52:10 — Recap with Jake and Tyler
Jake and Tyler sit down with former NBA referee and inventor Mike Costabile, the founder of the Precision Time System—a game-changing piece of officiating tech that’s now used in every NBA and March Madness game.In this episode, Mike walks through the controversial 1990 Bucks-Sixers game that cost him his job, the fallout that pushed him to invent a new way to keep time, and how he bootstrapped his garage-built prototype into a global product.You’ll hear the full story behind the tech that changed how basketball is played—and how one bad call led to an idea the NBA couldn’t ignore.⏱️ TIMESTAMPS00:00 — Intro01:50 — Getting into Officiating04:30 — Politics of Refereeing06:55 — Breaking into the NBA09:20 — “Managing the Game”12:15 — The 1990 Blown Call15:00 — Fallout and Getting Fired18:20 — Inventing Precision Time21:10 — Early NBA Pushback24:30 — How the System Works27:10 — Bootstrapping the Business30:05 — Landing the NBA Deal33:00 — Lawsuits and Copycats36:20 — Why Other Leagues Lag38:40 — Human vs. Automated Refs42:00 — When Tech Goes Too Far45:00 — League Culture Differences48:15 — Selling the Company50:00 — Legacy and What’s Next52:30 — Recap with Jake and Tyler
Jake and Tyler sit down with Brodie League founder Connor Renton to break down how he turned adult rec sports into a scalable business. At just 28 years old, Connor has built Brodie into a 34-market operation with a full-time team, hundreds of part-timers, a custom app, and a brand that feels more like a lifestyle company than a local league. The three talk about scaling community, building systems that last, and why rec sports are way more serious than they look from the outside.⏱️ TIMESTAMPS(00:00) Intro(02:05) Connor’s background in rec sports(06:00) Why adults still join leagues(10:45) What makes Brodie feel different(14:20) Early wins: stats and content(18:30) Building a high-touch experience(23:20) Why Brodie built its own tech(30:45) Content as product(35:10) Expansion strategy(39:45) Ownership model and what’s next(45:20) Final thoughts
John Zeglinski was a two-sport athlete at Wake Forest back when concussions meant smelling salts and getting back in the game.Now, he's the CEO of SAFR—a spring-loaded helmet cover shown to reduce concussions by up to 48% in live play and 77% in lab testing.In this episode, Jake and Tyler talk to Ziggy about the business of head safety in football: how SAFR works, why aesthetics are critical for adoption, and what’s keeping it out of the NFL—for now.They also dig into the broader culture around football safety, the helmet refurbishing industry, and the surprising reasons schools haven’t made these devices mandatory.If you’ve ever wondered why more players don’t wear protective gear, this episode will change the way you look at the game.⏱️ TIMESTAMPS00:00 – Intro00:56 – What head safety was like when Ziggy played02:36 – How the concussion conversation evolved05:55 – New concussion data from Penn State & Mecklenburg County07:07 – How SAFR works and how it compares to Guardian Cap10:50 – Spring-loaded design and energy transfer explained13:32 – The physics and materials behind SAFR15:30 – Why aesthetics matter for player adoption17:15 – What it would take to get NFL approval20:18 – Helmet refurbishing and manufacturer incentives21:05 – Risk homeostasis and coaching culture23:13 – Technique vs. tech: what actually makes football safer24:03 – Buying the company and early momentum26:05 – Why Guardian Cap’s visibility helped everyone27:59 – Youth player demand and future adoption29:44 – Declining youth participation and the safety narrative30:39 – Can SAFR expand into other sports?31:21 – Recap with Jake and Tyler
Episode 6 | Jake and Tyler discuss the dramatic DraftKings vs. Fanatics battle for PointsBet’s US operations, followed up by Jake’s augmented reality predictions – specifically, how it might affect sports. This week’s guest interview is with Frank Michael Smith, joining Jake & Tyler to talk about what it’s like to post “talking head” style content on TikTok, as well as a falling out with one of sports media’s biggest aggregators and how it inevitably led to the rise of Juice Productions. To conclude this episode, the guys draft American sports leagues they would most like to get an expansion team in.
Episode 5 | Jake and Tyler discuss Netflix’s continuous failure to land the rights to live sports, followed by Jake jumping into the accessibility of adaptive sports and the role of the Paralympics TikTok account. The guys also interview Thomas Northcutt, a graphic designer for the Brooklyn Nets. Thomas shares the behind-the-scenes of being a graphic designer in the NBA and the direction he sees for the future of sports content. Wrapping it up, Jake and Tyler give us their sports predictions as Q2 of 2023 closes out.
Episode 4 - EMERGENCY EPISODE | Jake and Tyler discuss the breaking news of the PGA Tour, LIV Golf, and the European Tour merging and they break down who they think comes out as the real winner. Then Jake pitches everyone on his new multi-million dollar business idea and Tyler talks with Jordan Haber, the guy who found a loophole in the NBA's Collective Bargaining Agreement in order to make himself eligible for the draft without ever playing basketball. And finally, the guys end by debating whether or not the Astros went too far by taking jabs at Oakland A's fans.
For more on Uncle Charlie or to work with Jake and Tyler, visit unclecharlie.co
Episode 3 | Jake and Tyler discuss the recent ESPN turmoil around the controversial hiring of Pat McAfee amidst job cuts. They look under the hood and dissect MLB's secret $3 billion company, Tyler interviews Indiana Pacer's rookie Benedict Mathurin and Duke's Tyrese Proctor about their financial plans off the court, and at the end, Jake and Tyler introduce this week's "Biggest Loser."
For more on Uncle Charlie or to work with Jake and Tyler, visit unclecharlie.co
Episode 2 | Jake and Tyler analyze the XFL's branding and bleak future, followed by an exploration of Fanatics' rise as a data-driven powerhouse. Lawson McDonald, a co-founder of the Hockey Guys and the Fan Club Podcast, joins the show to discuss the NHL's branding challenges during the playoffs as well as his recent interview with Isaac Rochelle. And lastly, Tyler and Jake draft their top sports moments they wish social media had existed for.
For more on Uncle Charlie or to work with Jake and Tyler, visit unclecharlie.co
Episode 1 | Jake and Tyler discuss the downfall of Bally Sports and its impact on sports media, delve into the Kentucky Derby's highlights and missteps, and share insights from an exclusive interview with the creators of Wilson's Viral 3D-printed basketball. Plus, they uncover the amusing story behind Super Bowl 57's viewership numbers.
For more on Uncle Charlie or to work with Jake and Tyler, visit unclecharlie.co
Jack Adler is the founder of Out2Win, a data platform that ranks college athletes by their off-the-field marketability. With NIL projected to reach $2.55 billion by 2026 and 81% of payments still flowing through booster-led collectives, Jack joined us to explain why the current system is broken—and what’s coming next.In this episode, we unpack how brands can stop wasting money, why true influencer-athletes are winning, and how upcoming regulations like the House v. NCAA settlement could reshape college sports forever. Jack also shares how his scoring platform works, why Arch Manning’s $6.8M valuation is misleading, and why the smartest brands are already shifting away from highlight-reel athletes in favor of content creators.⏱️ TIMESTAMPS00:00 — Intro01:16 — Jack Adler's elevator pitch for Out2Win02:33 — The Out2Win Score and influencer valuation methodology04:41 — Why Arch Manning’s $6.8M valuation doesn’t add up06:32 — How to find “hidden gem” athletes like Bryson Webb08:49 — Is NIL broken? Jack’s take on the current landscape10:02 — Real NIL vs. pay-for-play: The two-tiered system13:31 — Why “fair market value” is a flawed concept15:55 — Booster fatigue and the unsustainability of collectives19:06 — Are athletic departments headed toward privatization?21:19 — What happens to non-revenue sports under new rules?23:26 — How athletes like Livvy Dunne complicate revenue sharing30:29 — The marketing value of athletes for universities31:36 — How influencer marketing survives the NIL reset33:04 — Why smarter NIL dollars will beat bigger ones35:14 — Jack’s playbook for fixing NIL as college sports commissioner36:30 — Could the federal government regulate this?39:25 — The future of pro athlete content and NIL crossover40:52 — Jack’s advice to athletes and brands42:27 — Outro42:38 — Recap with Jake and Tyler
Full video: https://www.youtube.com/watch?v=u1-qKU1Ro_A&t=1s&ab_channel=TylerWebbBefore the age of 21, Derrick Brown had already tried to quit football, he had his first child and had turned down over $10 million.So how did he become one of the NFL’s best young superstars, all while starting a $6M side hustle? Well, the answer lies in his working-class upbringing, a piece of advice from a veteran teammate, and a pandemic-era obsession with Zillow.
Full video: https://www.youtube.com/@tylermwebb/videos
How did Justin Pugh go from receiving just one D1 offer (from one of the worst schools in the country) to earning $54M in the NFL… and why is he now contemplating leaving it all behind to become a YouTuber?
The answer lies in a $250,000 mistake, a “secret society” business meeting, and a $70,000 NFL tour.
Full video: https://www.youtube.com/@tylermwebb/videos
In this episode, I sit down with Chiefs WR Marquise "Hollywood" Brown to uncover his incredible journey from humble beginnings to becoming a savvy real estate investor.
Hollywood shares how he went from racing kids for pocket change to co-founding a $57M luxury real estate fund. We discuss his early struggles, financial lessons learned in the NFL, and his bold vision to redefine athlete wealth and legacy.
0:00 – Introduction0:27 – Early Life and Relationship with Money1:40 – Football as the Path Out4:14 – First NFL Paycheck5:14 – Navigating Financial Advisors7:19 – Regrets with Rookie Contract8:20 – Developing a Hustler’s Mentality10:30 – Money in the NFL Locker Room12:49 – Switching Financial Advisors14:17 – Transitioning into Real Estate16:52 – Importance of Building a Team19:02 – Challenges in Pitching Real Estate to NFL Players21:05 – Raising Funds for the Platinum Pro Fund23:08 – Real Estate as a Lifestyle Investment25:16 – Investment Portfolio and Advice for Athletes26:24 – Aspiring to Own an NBA Team27:47 – Long-Term Vision and Legacy29:01 – Closing Remarks