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 profession with its own "pro card." It's part locker-room confession, part startup pitch, and a rare look at what an NFL career looks like the moment the cameras stop rolling.

⏱️ Timestamps

00:00 — Intro: Meet Austin Ekeler

00:29 — Life After the Cameras Leave: What actually happens post-injury

01:34 — Time to Move On

02:47 — The Adrian Peterson Effect: Why "back in nine months" became the norm

04:51 — The Bell Curve of a Career

05:35 — Social Currency: Why Austin's staying in the game even off the field

07:01 — Learning Claude Code

08:04 — The Shovel Analogy

09:41 — From Website to App: Fixing the login complaints that started it all

11:26 — Where Fantasy Meets the Law: The $250 rule for active NFL players

13:31 — Drafting Himself... and Losing: The celebrity league story

17:29 — The Missing Pro Card: Why fantasy sports has no industry-wide "legit" status

19:13 — What a Pro Card Actually Buys You: Benefits, credibility, and bragging rights

21:41 — Inside the $100K Leagues: Gamblers, owners, and friend groups with deep pockets

23:20 — Why casual players might lead the whole industry

25:07 — How to join Fantasy Royale before the season starts

26:29 — The Austin origin story Tyler never told

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 advice they wish someone had given them at 19. It's part confession, part career manual, and fully unfiltered about why "I'm passionate about sports" is the worst pitch you can make.

⏱️ Timestamps

00:00 — Intro

01:30 — Pre-Med Dropout, Round One: Jake's chemistry class ends a medical career

03:57 — The LLC That Did Nothing: Starting a business with zero business to run

06:06 — $30 an Episode: The first time getting paid felt like winning the lottery

06:59 — Meet the Gopher: How a sports lawyer's errand-runner became a career launchpad

09:15 — Enter Tyler: A COVID-season baseball league, a cold call, and a new partner

12:20 — Patch Adams Did This: Why two guys both wanted to be doctors for the wrong reasons

16:38 — The $100 Graphic: Googling "How to Photoshop" mid-freelance-job

21:02 — Skip the Job Hunt: Why the real advice is "go work at a pizza place"

23:36 — The Worst Pitch in Sports: Why "I'm passionate about sports" gets you nowhere

26:09 — Get Paid Without a Boss: The new path that skips the job application entirely

29:31 — The College Loophole: Why four years of low stakes is your biggest advantage

34:26 — The Story of the Story: How people talk about you when you're not in the room

41:02 — Six Paragraphs Is Too Many: What actually makes a cold DM worth answering

43:16 — Outro

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-hand look at a deal that could change how creators and college programs do business.

⏱️ Timestamps

00:00 — Intro

00:49 — Reunion Tour: Cullen's back, and he's got receipts

01:28 — A Photo, A DM, A Deal

03:33 — Why Cullen's paying zero dollars for a jersey patch

06:23 — Who's Really Winning Here?

09:05 — Butts in Seats: The real scoreboard Cullen's tracking for success

11:31 — Alumni reactions and a Miami Dolphins fan analogy

13:32 — Why the story might outshine the season itself

15:41 — Creative Freedom, No Committee: Cullen's non-negotiable

18:33 — Cullen's advice to creators

21:08 — Hiring His First Employee

26:31 — ESPN Vets Need Not... Actually, Apply

28:12 — Put a Price On It

30:23 — Outro

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. Discover how taking a player-first approach turned one of the most hated pieces of athletic gear into a high-tech equipment powerhouse.

⏱️ Timestamps

00:00 – Intro: Meet Matt Hall & TrueFit Customs

00:51 – From Pre-Med Tutor to "Tutor Pimp"

02:18 – Why 3D Printing Changes the Custom-Fit Game

04:44 – The Wild Early Days of Stone Models & Manual Labor

07:11 – Resins, Lasers, and Light: Modern 3D Tech Explained

08:20 – Spotting a $1B Untapped Sports Vertical

11:44 – The 1990 Japanese Dental Paper That Built TrueFit

14:56 – Surviving Shark Tank & Facing Mark Cuban

20:54 – Negotiating Valuations with Kevin O'Leary & Rashad Jennings

24:22 – Hacking the Pro Sports Distribution System

27:44 – Why Nike and Big Tech Missed the Mouthguard Loophole

32:07 – Securing Investments directly from Pro Athletic Trainers

38:05 – Scaling Custom Fit: AI, Material Science, & Scanners

41:00 – Protection vs. Fit: How Ultra-Thin Guards Work

44:09 – Outro: Key Takeaways on TrueFit's Category Dominance

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 forward. Afterward, Tyler and Jake break down the true marketing ROI of the viral campaign and address any pushback regarding monetizing creator content.

Timestamps

00:00 – Intro

00:53 – Pitching to Become Chief World Cup Watchers

03:32 – Long Leashes, Tattoos, and Total Creative Freedom

06:09 – Pure Joy vs. Expert Ball Knowledge

08:09 – Man-on-the-Street Marketing & Trial by Fire

11:08 – Seizing a Once-in-a-Lifetime Creator Opportunity

14:03 – Times Square as the Ultimate World Cup Cultural Hub

19:58 – Addressing the Fear of Getting "Typecast"

21:37 – Post-Interview Breakdown: The Hidden Costs of Viral Activations

28:20 – Did Fox’s $50,000 Bet Return Real Value?

34:11 – Shoulder Content vs. Main Broadcasts

41:41 – Outro: Pushing Back on "Intentionally Amateur" Content Creation

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 in 39 days. From scaling up content operations on the fly to walking away with a razor-thin profit margin of just $500, Jack offers an insanely transparent look at what it takes to build a modern sports media brand from the ground up.

⏱️ Timestamps

00:00 – Intro

00:36 – Clearing Up the Guest Record

01:19 – Why People Love Financial Transparency

02:20 – How the 33-Game World Cup Plan Was Born

03:30 – Selling a Mass-Scale Content Tour in Just 40 Days

08:38 – The SparkNotes Version: 33 Games, 39 Days, and $500 Profit

10:27 – Breaking Down the Return on Investment for a Media Brand

12:23 – Why Daily YouTube Vlogging Underperformed

23:36 – The $35,000 Ticket Problem and Missing Travel Sponsors

34:41 – Hotel Sharing, HR Violations, and Keeping Content "Hungry"

39:18 – Runway, Reinvesting Capital, and the Future of Underdog Deals

45:07 – Surviving "No Man's Land" as a Mid-Sized Creator Company

50:20 – The Annual Update: Seeking a College Football Jersey Patch Sponsor

55:35 – Outro

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 took to convince 100,000 subscribers to follow him from one company to the next. Along the way: the "secret weapon" RSS feed that powers his daily grind, why AI can aggregate news but can't replicate taste, and an honest look at why newsletter advertising is still years behind podcasts. If you've ever wondered what it takes to build (and keep) an audience that opens your work every single day, this one's a masterclass.

⏱️ Timestamps

00:00 — Intro

00:45 — The roundabout path into sports media

01:47 — Bleacher Report, ESPN, and finding his voice

03:31 — Trading TV glamour for newsletters

03:45 — The Skimm and the lightbulb moment

06:24 — Advice for starting a newsletter from scratch

08:59 — Newsletters vs. social media: the data problem

10:55 — Selling Sports Internet to Axios

13:56 — The power of a daily habit

16:22 — Kendall's process and his RSS "secret weapon"

19:45 — Standing out from AI aggregation

22:28 — Why newsletters are booming again

25:56 — What Yahoo actually is today

29:23 — Giving away ideas for free on Twitter

39:45 — Sharing competitors' work and building trust

42:11 — Why newsletter advertising is still so immature

46:50 — The newsletters Kendall actually reads

48:54 — Outro

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, Frank breaks down how a side project quietly cannibalized his company's flagship game, why removing the prize money actually supercharged the network effect, and what having a business that runs without him means for his future as a creator. It's a candid look at what happens when the thing you built for fun outperforms everything you spent years trying to force.

⏱️ Timestamps

00:00 – Intro to GeoSports

00:55 – Welcome Back, Frank

01:37 – The Hungover Sunday Build

04:36 – From Side Project to Sole Focus

07:34 – Why This One Actually Worked

12:55 – The Share Score Secret

16:24 – Claude Writes the Backstories

17:24 – Monetizing a Free Game

19:57 – Staying Off His Main Channels

22:21 – New Dad, Dry Spell

25:10 – Life Beyond Content Creation

30:36 – Frank's Challenge to Tyler

31:18 – Outro: Go Play Today

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 ultimately weighing in with her own verdict on who made the stronger case. It's a lively, surprisingly personal debate about where the line is between helpful tool and creative shortcut — and whether that line is already gone.

⏱️ Timestamps

00:00 — Intro: AI Takes the Field

00:34 — Gabby Sets the Rules

01:01 — Opening Statements Fly

04:37 — Ethics or Job Security?

11:09 — The Getty Images Lawsuit

18:37 — The Addiction Analogy

25:52 — Individual vs. Organization

33:16 — Ferrari vs. Ford

37:47 — Gabby Breaks Up the Heat

43:44 — The Cognitive Debt Study

49:14 — Closing Arguments

53:16 — Who Does Gabby Crown As The Winner?

56:19 — Outro

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 most under-analyzed asset class in media, and what a "CNBC for sports" could really mean. It's part business deep-dive, part mentorship session... Tyler and Jake don't hold back.

⏱️ Timestamps

00:00 — Intro
00:36 — Pre-Womb Best Friends: The Origin Story
08:22 — Why They Raised Venture Capital
11:16 — The White Space: Sports Business Without a Home
13:17 — How They Actually Landed Courtside Ventures
16:35 — The Future of VC-Backed Creators
20:53 — "You Are a Creator" — Jake Drops the Truth Bomb
35:13 — Measuring Success When the Big Numbers Don't Come
38:25 — What's Actually Missing From Sports Business Media
42:22 — Does a "Sports Business Newscast" Have Legs?
47:00 — When a World Surf League Video Goes Unexpectedly Viral
50:27 — The Law of Large Numbers: Why Casting Wide Nets Works
1:02:35 — How Tyler Actually Defines Success as a Creator
1:05:00 — Outro