Sportonomics
Two sports marketers, Jake Kranz and Tyler Webb, interview unique people in sports, business, marketing, and technology to explore ideas shaping the future of the sports industry. The podcast covers insights from entrepreneurs, executives, and innovators, highlighting how they navigate the intersection of sports and commerce.
Episodes
They Weren’t Banned: The Real Story of the Nike MaxSight
Every year, photos of athletes in red contact lenses go viral, and every year the same rumor returns that they were banned for being too good. Tyler and Jake sit down with Dr. Alan Reichow, the vision scientist who helped build the Nike MaxSight and now runs its successor, to find out what those tints really do, why a footwear giant got into eyewear, and what actually happened to the original. The
The Cleat Startup That's Beating Nike Without Paying a Single Player
Jack Rasmussen couldn't read until he was 20, didn't play football until he was 23, and had zero background in footwear, yet somehow built the cleat technology now worn by 100 unpaid NFL players. Tyler and Jake dig into the wild origin story: a viral video, a 4 million-view overnight blowup, and a 13-hour drive to chase down his first investor. They also get into the harder questions, like
Why I Failed as a Content Creator for 14 Years
For the first time, Jake flips the mic around — putting Tyler in the guest chair to unpack the entire, occasionally chaotic story of how he became a full-time content creator. From basement Halloween-costume skits filmed straight into a webcam, to a scammy Wild West era of follow-for-follow growth hacks, to the exact 45-second video that finally broke through and changed everything, this is the or
Bond Almand Biked To All 30 NFL Stadiums. Next, He Wants To Bike The Whole Planet.
Bond Almand just biked to all 30 NFL stadiums — 11,000-plus miles in 65 days — and it's not even his craziest idea. This week, Tyler and Jake sit down with the ultra-endurance cyclist who broke the Alaska-to-Argentina record; they learn what it actually takes to build a sport from scratch with zero teams or leagues, and hear about the next audacious goal on his list: biking from Cape Town, Sou
What Happens When AI Can Get More Views Than You?
There's a 23-year-old who ran over a hundred YouTube channels staffed by $26-an-hour Fiverr actors reading AI-written scripts...and collectively, they pulled more views than the New York Times. Jake came back from the woods with a new term for this corner of the internet ("ghost creators") and a surprisingly optimistic case for them; Tyler came in with a Semaphore investigation and a
His First Brand Deal Was $50. The Rest Is History.
PeteTakes turned a fantasy football weatherman bit and a parody song into a career — but somewhere along the way, he learned the hard way that getting paid for something you love can quietly ruin why you loved it in the first place. Tyler sits down with the creator behind "Coop DeJean Is Not a Safety" to unpack the slow climb from 43 TikTok followers to a booming business, the brand deal
Austin Ekeler On Turning Fantasy Football Players Professional
Nine seasons in the NFL, one torn Achilles, and a newborn later, Austin Ekeler is rebuilding his career in real time — not on the field, but inside Claude Code. Tyler sits down with the former Chargers and Commanders running back to talk free agency at 31, the surprisingly firm rules around players and fantasy football, and Austin's bigger bet: turning fantasy sports into a legitimate professi
The Real Advice for Breaking Into Sports
Two guys who both dropped out of pre-med, stumbled into sports by accident and somehow built a business anyway are finally answering the one question that won't stop landing in their inboxes: how do you actually get a job in sports? Tyler and Jake trade origin stories, from a $30-an-episode podcast gig to a Photoshop tutorial learned in real time for a $100 graphic, before laying out the exact
Cullen Honohan Made College Sports History for Free
A local pizza-shop photo op with a coach's kid just rewrote the rules of college sports sponsorship. Cullen Honohan of All Hail BBall joins Tyler to break down how he became the first content creator with his own logo on a Division I jersey — without paying a single dollar upfront. From the wild backstory to the six-figure value he says social reach can deliver instead of cash, this is a first
Surviving Shark Tank & Disrupting a $1B Equipment Market
From tutoring pre-med students to making custom 3D-printed mouthguards for NFL and NHL stars, TrueFit Customs founder Matt Hall reveals how he disrupted a untapped billion-dollar sports market. This week Tyler and Jake break down his journey pitching on Shark Tank, how he leveraged advanced material science and AI, and secured game-changing investments directly from professional athletic trainers.
Inside the Times Square Glass Box: Did Fox’s Viral World Cup Campaign Work?
Out of 6,000 applicants, content creators Kevin and Austin were selected by Fox Sports and Indeed to receive $50,000 to sit in a glass box in Times Square and watch every single match of the FIFA World Cup. In this episode, the duo join Jake and Tyler to discuss their complete creative freedom, surviving 14-hour days inside the box, and whether they fear getting typecast in their careers moving fo
Inside the $80,000 World Cup Content Experiment with Jack Settleman
What does it take to pull off a month-and-a-half-long sports content marathon across three countries, and is the massive financial risk actually worth it? In this episode, Jake and Tyler bring back Snapback Sports founder, Jack Settleman, for a fourth time as he breaks down the chaotic logistics, daily YouTube vlogging stumbles, and financial reality of sending his brother to 33 World Cup matches
The Michael Jordan of Newsletters: Kendall Baker's Playbook for Daily Email
From a college kid running the SportsCenter teleprompter to the newsletter that reaches over a million inboxes every morning, Kendall Baker has lived the entire boom-bust-boom cycle of email media — and he's not holding back. He breaks down why he sent 50 different newsletter formats in his first three months, how he negotiated an acquisition without ever naming a price, and what it actually t
Frank Michael Smith Vibe-Coded a Game in a Weekend...Now 100K People Play Daily
Six years into building a content empire with 3.5 million followers, Frank Michael Smith accidentally built something bigger during a hungover Sunday afternoon. In just 14 hours of "vibe coding" with Claude, he created GeoSports — a map-tapping sports trivia game with no app, no tutorial, and no push notifications — and it's now pulling in 100,000 daily players. In this episode, Fran
AI vs. Authenticity: The Sports Creative Showdown
In this head-to-head debate, Jake and Tyler go toe-to-toe on whether AI belongs in sports creative work — arguing everything from copyright theft and job security to "cognitive debt" and the soul of what makes sports fandom human. Producer-turned-moderator, Gabby, keeps the conversation on track, lobbing sharp follow-up questions, stepping in to referee when things get heated, and ultima
The Missing Analyst: Why No One is Doing Sports Business Coverage Right
Two best friends who've known each other literally since before one of them was born — Sid Balaga and Suraj Peramanu of The 4th Quarter — join Tyler and Jake to talk about building a venture-backed sports business media company from a basement during knee surgery recovery. They break down what it actually looks like to raise capital as a content creator, why they believe sports business is the
Your 9-to-5 Isn't as Safe as You Think
NFL content creator Matt King sits down with Tyler and Jake to pull back the curtain on one of the most relatable decisions in the creator economy: when — and how — to quit your day job. Matt walks through the exact mindset, numbers, and support system that led him to go all-in on content creation in November 2025, including the specific financial threshold he set for himself before making the lea
Why the Best Sports Experience in America Might Be in a Colorado Ski Town
What started as a late-night FaceTime from a friend at a chaotic hockey game in Breckenridge, Colorado turned into one of the most unexpected sports business stories you'll hear. Rick Batenburg — venture capitalist, cannabis entrepreneur, and self-described "Jackie Moon of Breckenridge" — built the Breckenridge Vipers from scratch eleven years ago with 35 people in the stands, purely because he wa
What 6 Years as a Creator Actually Looks Like
Lawson McDonald, co-founder of The Hockey Guys, returns to Sportonomics for the first time since S1 E2.He pulls back the curtain on what six years in the creator economy actually looks like — plateauing views, compounding networks, and why brand deals keep coming even when the algorithm doesn't cooperate. The conversation takes a sharp turn into brand-building as Lawson breaks down how he'
The Author Who Played Semi-Pro in Iceland Says American Soccer Is Finally Ready
In this episode, Tyler and Jake sit down with Mark Franek — author of American Soccer Nation and semi-pro soccer veteran — to trace the remarkable and often overlooked 150-year history of soccer in the United States.Mark breaks down what makes MLS's single-entity, no-relegation structure both uniquely frustrating for soccer purists and genuinely necessary for survival in the American sports la
$50 a Month to 125 Million Followers: The Overtime Blueprint with Tom Weingarten
From skipping to page 50 of Google and earning $50 a month to helping build one of the most dominant sports media companies on the internet, Tom Weingarten's journey at Overtime is a masterclass in finding opportunity where no one else is looking. In this episode, Tom pulls back the curtain on how Overtime built a decentralized network of 1,000 filmers worldwide, cracked the code on covering h
Audience First, Business Second: Cole Nevins' 5 Predictions for the Sports Creator Economy
Cole Nevins has been in the sports media space since he was eight years old; from blogging on an iPod Touch to building a high school creator network, running a content agency, and now leading creator partnerships at Yahoo Sports. In this episode, Tyler and Cole dig into the evolution of the sports creator economy, how making money online has fundamentally changed who becomes a creator, and why &q
Why (Some) Athletes Shouldn’t Be Creators
Jake Miller, co-founder of Arvelo Media, joins Tyler to unpack what it actually takes to build a personal brand as an athlete or public figure in 2026. They dig into the "it factor" — why some people are natural content creators and others simply aren't — and how to tell the difference before wasting everyone's time. The conversation wraps with a grounded take on AI: not as a thr
The Kid Who Bet Everything on YouTube...And Finally Won
Justin Leusner started making YouTube videos at age 10, built a 100-person student media company at Penn State, and recently pulled off visiting all 30 NBA arenas in 30 days — raising over $100,000 for Make-A-Wish along the way. In this episode, Justin opens up about the mental health lows that almost ended his creator career, the faith journey that brought him back, and the meticulous behind-the-
The Most Iconic Two Minutes in Sports — On the Ground at Churchill Downs
Tyler and Jake are live in Louisville, Kentucky for the 152nd Kentucky Derby — and before the gates open, they're breaking down everything that makes this two-minute race a week-long American institution. From the fascinating origins of Churchill Downs and the "Run for the Roses" tradition to the mechanics of pari-mutuel betting and $5,000 mint julep cups, this episode covers the his
Johann Kroll's Guide to Not Going Broke
Tyler and Jake sit down with Johann Kroll — a former Ohio State and minor league hockey player turned CFA and CFP — who now runs Hockey Wealth, a firm dedicated entirely to financial planning for professional hockey players. Johann breaks down the most common financial mistakes he sees players make, from chasing crypto and flashy restaurant investments to neglecting the boring-but-powerful fundame
Justin Pugh + The Billion-Dollar Battle for the NFL's Global Future
Have you ever wondered why some NFL stars build lasting business empires while others end up broke just years after their final game? In this episode, 11-year NFL veteran Justin Pugh discusses his transition from an offensive lineman to the Commissioner of the Italian Football League, where he is working to "plant the flag" for American football in Europe. We dive deep into the hidden reality of $
The $100 Batting Glove: How Gas Money Created a Baseball Empire
Bear Mayer took a teenage need for gas money and turned it into Bruce Bolt, the premium brand that turned batting gloves from an afterthought into a high-end status symbol. This week, Tyler sits down with the founder to break down the grit required to prototype 18 versions of a single glove and the "hockey stick" growth that followed a viral media moment in a high school English class. T
Redefining Athlete Marketing: How Cullen Honohan is Becoming a Go-To Storyteller
Cullen Honohan has transformed a self-taught passion for graphic design into All Hail BBall, one of the most compelling sports media brands in the industry.This week, Jake and Tyler sit down with the former agency director turned creator to break down the transition from cold DMing for freelance gigs to filming with future NBA lottery picks. They discuss the grit required to "escape the algor
Jordan Rogers: Inside Nike, the Creator Economy & What Sports Marketing Actually Is
Jordan Rogers has worked inside one of the biggest brands in the world, and now helps others compete with it.This week, Jake and Tyler sit down with the former Nike brand leader turned creator and consultant to break down the shift from corporate marketing to the algorithm-driven era. They talk about why big companies struggle to adapt, how creators are building leverage faster than ever, and what
The Voice in the Ring: Big Mo's Rise to the Biggest Stage in Boxing
Most ring announcers spend decades waiting for their moment. Kody 'Big Mo' Mommaerts didn't wait for anything.Tyler and Jake sit down with Kody "Big Mo" Bigmo, one of combat sports' fastest-rising ring announcers, to unpack how a college football player from Colorado built a global career in the middle of the ring. They dig into how he speed-ran an industry where most ann
How 7-on-7 Took Over Football
7-on-7 started as an offseason drill. Now it's becoming its own sport.This week, Tyler and Jake sit down with Ty Thomas, founder of My7on7, to unpack how a Minnesota startup grew from 150 kids to nearly 8,000 players — and what that growth means for the future of football development. They talk about the real difference between 7-on-7 and flag football, why high school coaches are still split
What the Camera Caught — Breaking Down an 11-Hour Day Inside Youth Hockey Officiating
🔗 WATCH THE FULL VIDEO: https://youtu.be/pbThK_e-yjg?si=c6DjHXh1i0m0kY6u Tyler spent 11 hours mic'd up at a youth hockey rink — and the parent interviews changed everything.After spending a full day together at a youth hockey rink, Tyler and Brandon sit down to unpack what came out of the day — especially the parent interviews, the money stress that quietly fuels rink-side tension, and how it&
This YouTuber Just Spent $250K on Content, Was it Worth It?
Jack Settleman is nine years into building Snapback Sports — and it's starting to feel like a breakthrough moment.This week, Tyler and Jake sit down with the college football content creator to break down Season 2's numbers, unpack how he's approaching the newly-cleared NCAA jersey patch opportunity, and discuss what it looks like to scale a media brand while life gets more complicated. Plus, the
Why Turnover Chains Became the Hottest Trend in Sports
Turnover chains started as a sideline celebration. Now they’re becoming a new category in sports merchandising.This week, Jake and Tyler sit down with James Helms, founder of PopChains, to unpack how a Houston startup is turning bold, customizable chains into marketing tools, fan collectibles, and digital engagement platforms. They talk about building U.S.-based manufacturing, landing partners lik
How Two Childhood Friends Built Strictly B-Ball
Joe Doerrer and Nolan Newberg didn’t set out to build a company — they just couldn’t stop making basketball content.This week, Jake and Tyler sit down with the duo behind Strictly B-Ball to break down how a childhood friendship turned into a full-fledged sports media business. They talk about the Vine-era grind, finding their voice on TikTok, pioneering voiceover storytelling in high school basket
The Uncomfortable Middle of Broadcasting and Content with Max Browne
Max Browne is living in the overlap between two worlds that don’t fully trust each other yet: broadcasting and content creation.This week, Tyler sit down with the ACC Network analyst and former USC quarterback to talk about the “that’s cute” phase of being a creator, why digital fluency is becoming table stakes for on-air talent, and how owning your platform might be the most stable part of a noto
Meet the Strava of Fishing
A frustrating catch-and-release moment sparked an idea that turned into a full-fledged fishing tech company.This week, Jake and Tyler sit down with Lawrence, founder of Fishtechy and creator of the Proofball, to talk about measuring fish without harming them, turning a physical product into a data-driven platform, and why fishing might be the next sport to see a true social-tech revolution. They a
The Most Interesting Sports Creator You’re Not Following (Yet)
Jack Appleby has spent 15 years building brands on the internet, and then used that same playbook to build two of his own.This week, Jake and Tyler sit down with the creator behind How to Hoop Forever and Future Social to talk about treating content like a business, why perspective matters more than information, and how Jack turned rec league basketball, storytelling, and strategy into sustainable
How Sportsball Turned Data Into Art
Riley Martin doesn’t break news or argue hot takes — he explains sports so clearly that anyone can follow along.This week, Jake and Tyler sit down with the creator behind Sportsball to unpack how data visualization became his creative edge, why he designs content for casual fans first, and how focusing on a single fastball helped him build a durable, brand-friendly creator business without chasing
How a $65 Loan Became a $10M Football Glove Brand
Nathan Dorton started his football brand with a $65 loan, a Photoshop glove template, and a factory connection in Pakistan. Today, Phenom Elite is a $10M business redefining how football gear, culture, and IP intersect.This week, Jake and Tyler sat down with Nathan to talk about building an equipment brand without VC money, why licensing SpongeBob and Kool-Aid works better than superheroes, and ho
How Four College Students Solved Sports’ Most Taboo Problem
Most sports innovation focuses on what fans can see. Almost none of it considers what happens when you can’t.This week, Jake and Tyler sat down with the founding team behind OneCourt, a startup using real-time player and ball-tracking data to turn live sports into a tactile experience for blind and low-vision fans. They break down how the idea started in college, why accessibility has lagged behin
Meet the Athletic Trainer Who Invented the Arm Sleeve (Lenny Currier)
A lot of people dream about playing professional sports. Fewer think about the careers built behind the scenes that make those games possible.This week, Jake and Tyler sit down with longtime athletic trainer Lenny, whose 50-year career spans high schools, minor league baseball, the NBA, and the Philadelphia 76ers. They talk about breaking into pro sports, the importance of networking, life on the
How Youth Sports (Accidentally) Became a $40 Billion Industry
Youth sports used to be simple — show up, play, go home. Today, it’s a fully developed industry with travel requirements, hotel contracts, massive tournaments, and real money flowing through every weekend on the calendar.This week, Jake and Tyler sat down with John D’Orsay, CEO of EventConnect, to break down how the youth sports economy actually works — from the rise of elite travel teams to the h
Meet the Guy Solving the Oldest Problem in Sports: Standing in Line
Stadiums track everything. Tickets, fans, sponsors, on-field performance, but one problem has quietly resisted innovation for decades: lines.This week, Jake and Tyler sat down with Sam Porta, founder of Queues, to break down how he went from hacking together queue data at Georgia Tech to helping the Atlanta Braves cut wait times, increase throughput, and uncover hidden inefficiencies using compute
Why Does NFL Dominate Thanksgiving?
Thanksgiving and football feel like they’ve always gone together...but the story behind that tradition is way stranger than most fans realize.This week, Jake and Tyler break down the full history of Thanksgiving football, from Yale vs. Princeton in the 1800s to the Detroit Lions’ radio-fueled rise, the Cowboys volunteering their way into a national spotlight, and how the NFL turned a quiet holiday
From Fidget Spinners to Fox Sports: The Rise of Jordan Green
Jordan Green isn’t your typical 22-year-old founder.He’s built meme pages with millions of followers, brokered NIL deals for brands like Fox Sports and Gymshark, and launched his own agency — Glacier — from a college dorm room.This week, Jake and I sat down with Jordan to talk about the evolution of NIL, how athletes and brands can actually build trust instead of hype, and what the future of colle
Meet the NFL QB with a $1M Side Hustle (Kurt Benkert)
Kurt Benkert and Matt Blakely are redefining what a football brand can be.After Kurt’s NFL career, they launched DimeLab, a direct-to-consumer company making game-ready footballs that feel perfect right out of the box.This week, Jake and I sat down with them to talk about building a product from scratch, growing without burning out an audience, and turning 40,000+ bootstrapped orders into a retail
The Man Behind the Titleist Pro V1 Is Disrupting Golf Again
Dean Snell has built golf balls for Tiger Woods, Phil Mickelson, and thousands of weekend players, but his story is about craft, not fame.After decades at Titleist and TaylorMade, he launched Snell Golf to deliver premium performance without the price tag or tour hype.Jake and I sat down with Dean to unpack the creation of the Pro V1, why most golfers use the wrong ball, and how he’s quietly built
He Went From Making $11/Hour to a Nike Executive, Then He Quit (Brian Davison)
Brian Davison’s path into the sports industry wasn’t traditional—it was relentless.After leaving a college coaching job, he started selling sneakers at a Nike outlet for $11/hour. Over the next decade, he networked his way into corporate Nike, became one of the company’s elite EKINs, and eventually landed on the Nike basketball team, helping re-sign Giannis Antetokounmpo on a $240 million deal.Thi
How a JV Basketball Player Became the NBA's Youngest Broadcaster
Carlo Jiménez didn’t come from a broadcasting family. He didn’t play college ball. But at just 24, he’s already the radio voice of the LA Clippers—calling playoff games at Intuit Dome and growing a massive social media following along the way.This week, Jake and I sat down with Carlo to talk about how he went from JV benchwarmer to NBA broadcaster, the role content played in getting the job, and h
How a Flashing Mouthguard is Solving Sports' Concussion Problem
This week, Jake and I sat down with Drew Goodger, co-founder of Prevent Biometrics — the company behind those flashing red mouthguards you’ve seen all over rugby pitches and football fields.But Prevent isn’t just making gear — they’re building an infrastructure layer for head safety. Their tech tracks real-time head impacts with verified data, provides instant alerts, and is already shaping polici
Meet the Company Solving Guardian Caps’ Biggest Problem
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 a
Sports Content Is Getting Worse, Michael Gursha Is Trying to Fix It
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 explain
Why One Creator Just Turned Down a $100K+ Brand Deal to Bet on Himself
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 un
Glass Courts: A Peak Into the NBA's Next Big Experiment
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 player
The Truth Behind College Football's Latest $40K Viral Marketing Stunt
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 fan
Inside the Latest $325M Bet on Women’s Volleyball
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 c
Meet the YouTuber Taking a $250,000 Risk on College Football
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 i
Meet the Biomechanist Solving Baseball's Biggest Problem
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 patent
The NIL Bubble Is About to Pop - But What's Next?
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
How a Fired Ref Solved the NBA's Biggest Problem
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 hi
The $5B Rise of Rec Sports and the 28-Year-Old Behind It
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 system
The (Untold) Story of Derrick Brown - Full Interview
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
The (Untold) Story of Justin Pugh - Full Interview
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.
The (Untold) Story of Hollywood Brown - Full Interview
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 le
The Back-Up QB with a $1M+ Side Hustle: The (Untold) Story of Jordan Palmer
Full video: https://www.youtube.com/@tylermwebb/videos
How did Jordan Palmer go from receiving only one college offer and never starting a game in the NFL to becoming the league’s most popular quarterback coach?
Well, the answer lies in a weekly tradition with the Chicago Bears, a blind date with Blake Bortles, and a few million-dollar business ideas from three old high school teammates.
Chapter
He Was the #1 TE in the Country, Then He Disappeared - Adam Breneman Interview
Full video: https://www.youtube.com/@tylermwebb/videos
How did Adam Breneman go from the #1 tight end in the class of 2013 to retiring from football completely just two years later?
And how, after starting a successful career in politics at 21 years old, did Adam almost make it all the way back to the NFL?
Well, the answer lies in a national scandal, a meeting with an old high school teammate,
The Misunderstood History of Ricky Williams (Full Interview)
Full video: https://www.youtube.com/@tylermwebb
How did Ricky Williams go from the Heisman Trophy winner in 1998 to one of the most ridiculed players in football just 4 years later?
And why is he now beloved for the same thing that cost him $10M and 36 games in the prime of his career?
Well, the answer lies in a saying from his mom, a suggestion from a former roommate, and an invitation to Phoe
The Forgotten 5-Star QB: The Untold Story of Max Browne (Full Interview)
Full Video: https://www.youtube.com/@tylermwebb
How did Max Browne go from the No. 1 quarterback in the country in 2013 to sleeping on the floor of Gary V’s New York City office to becoming a rising star in college football once again?
Well, the answer lies in a QB battle with Sam Darnold, a career-ending injury, and dozens of YouTube videos from the kitchen counter.
How Coach RAC Accidentally Became a Savannah Banana (Full Interview)
YouTube Video: https://www.youtube.com/@tylermwebb
How did Robert Anthony Cruz (Coach RAC) go from living with his parents and failing to achieve his lifelong dream of playing in MLB to becoming one of the Savannah Bananas’ biggest stars?
Well, it wasn’t on purpose, and it might not last much longer.
But the answer lies in a 3 a.m. TikTok video, a $1,500 gamble, and a friend's suggestion that c
The Untold Story of How Jackson Olson Became a Savannah Banana (Full Interview)
Use code BANANAS15 for 15% off your next order from smackinsunflowerseeds.com - Dill Pickle is my favorite flavor.
How did Jackson Olson go from turning down the Arizona Diamondbacks to becoming one of the most popular baseball players in the world in less than four years?
The answer lies in his time as an Instacart driver, his decision to move to California for an ex-girlfriend, and one TikTo
How Austin Ekeler Plans to Become the Richest RB in the NFL
Use code TW15 for 15% off your first purchase at https://www.chillboys.com/ — it’s seriously my new favorite underwear (I just emptied my drawer to make room for more).
How did Austin Ekeler go from an unranked and undrafted DII running back to the Forbes 30 Under 30 List in less than 10 years?
The answer lies in his rugged upbringing, his (sometimes) delusional determination, and a financial s
The Untold Story of the NFL's Best Million Dollar Side Hustle (Ben DiNucci Full Interview)
Use code TW15 for 15% off your first purchase at ChillBoys.com
Full Video: COMING SOON
EPISODE DESCRIPTION
How did Ben DiNucci go from being a seventh-round backup quarterback to running one of the most successful brands in the NFL?
The answer is in his unlikely story, which includes a random DM, genius marketing, bad advice, and the most unlikely collaborations.
The Untold Story of the NFL's Most Viral QB (Kurt Benkert Full Interview)
Full Video: https://www.youtube.com/watch?v=MDcthTA9uVE&ab_channel=TylerWebb
In this episode, we explore Kurt Benkert's journey from an undrafted, three-star recruit to a well-liked NFL quarterback. We delve into his early life, football career, and his transition into gaming. Learn about his time with the Atlanta Falcons and Green Bay Packers, his struggles with his off-field hobbies, an
Reviewing 2023 Predictions and Forming Sports Business Predictions for 2024
Episode 27 | Jake and Tyler are back for the final episode of 2023, where they revisit predictions made at the beginning of the year and forecast what lies ahead in 2024 for the sports business world. The two begin by looking back at predictions on topics from TikTok getting banned to the legalization of sports betting, reflecting on whether their predictions hit or missed. After this, they make e
ESPN Bet Launch, Jimbo Fisher Finesses $76M, and Adam Faris
Episode 26 | In this episode, Jake and Tyler dive into the recent ESPN Bet launch, former Texas A&M football coach Jimbo Fisher’s contract buyout worth over $76M, creating short-form content for large companies, and a controversy about the ESPN Bet logo. First, Tyler leads a conversation about the ESPN Bet launch, discussing how this might impact the future of ESPN and sports betting. Followin
NFL in Europe, NBA In-Season Tournament, and Sports Connections
Episode 25 | Jake and Tyler kick this episode off by discussing the NFL’s European expansion plans and whether they see it happening in the future or not. Tyler dives into the details and makes a case for his opinion on the matter. Next, Jake explores several topics like the NBA In-Season Tournament, Black Bear Sports Group (a company that manages sports facilities), and predictions he made back i
Soccer Investing Trend, FaZe Clan’s Downfall, and Attending Every MNF Game
Episode 24 | Jake and Tyler begin this episode by delving into the trend of investment groups buying lower-tier clubs across lesser-known soccer leagues worldwide. Ryan Reynolds, Rob McElhenny, JJ Watt, and now Dude Perfect have all joined in on this emerging trend in the sports world. Next, Jake talks about the recent GameSquare Holdings acquisition of the eSports organization FaZe Clan. He dives
Baseball in Dubai, LIV Golf Check-In, and AI Athlete Tech
Episode 23 | In this episode, Jake and Tyler explore baseball’s newest league – Baseball United, a professional league based in Dubai – and whether MLB should be worried or not. Following this, Jake leads a discussion on LIV Golf. He dives into everything from the business and the players to the viewership and the merger with PGA, as well as what’s next for LIV. Next, Jeron Smith, co-founder of a
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