$20 Million to Power Play · Dylan Robbins, Founder & CEO of Lucra

Ultra-Premium Hospitality Built on Sport · Gary Spitalnik on Marquis Jet, Wheels Up & REAL SLX

Gary Spitalnik has been to 26 consecutive Super Bowls. He co-wrote a song they still play at Madison Square Garden. He helped build Marquis Jet and Wheels Up, two brands that opened private aviation to a whole new market. Now he is building REAL. I sat down with Gary on site in New York to walk through the whole arc. We get into what the top of the market actually wants in 2026, why authenticity cannot be manufactured, and how REAL turns the Rao's and McSorley's popups at the Super Bowl, the Masters, and the Ryder Cup into a business. Gary also breaks down his read on AI and the rising premium on human intelligence, the Thrive Eternal bet on the San Francisco Giants, and the cross-country Amtrak saga that became one of his all-time stories. A masterclass in experiential hospitality from one of the best to ever do it. Listen on Spotify and Apple. Read the full breakdown on Substack. Chapters: 00:00 Why he has so many stories 00:36 On site in New York at REAL 01:05 The career arc, chapter by chapter 03:40 REAL as the culmination 06:50 The Rao's popup and a 130-year-old institution 11:07 McSorley's in Augusta and real authenticity 12:13 What a REAL build actually looks like 14:30 It is all about the people 14:57 What he learned from Jesse Itzler and Kenny Dichter 25:37 AI is here. The premium is on human intelligence26:35 Ari Emanuel, Mark Shapiro, and the MARI bet 27:50 26 Super Bowls and the ceiling on premium 28:48 The Wheels Up Super Saturday tailgate 30:43 What 25 years has changed about Super Bowl week 34:24 Marquis Jet, Wheels Up, and Real Jet 37:07 Thrive Eternal and the Giants 41:29 Advice for anyone starting a league or festival 44:17 Do not let them see you sweat 47:10 The Amtrak story 51:12 Build your life resume 51:39 The one event everyone should have on their list Subscribe to Under the Number: → Substack: https://underthenumber.substack.com/ → YouTube: https://youtu.be/6CFb_Fovzy0 → Spotify: https://open.spotify.com/episode/0i7avYEydRU3SataONB8C7?si=zgclKJ_QQKeiiyb0-h1AkA → Apple Podcasts: https://podcasts.apple.com/us/podcast/ultra-premium-hospitality-built-on-sport-gary-spitalnik/id1730764733?i=1000770792660 #UnderTheNumber #SportsBusiness #SportsHospitality #UnderTheNumber #REALSLX #ExperientialMarketing #PrivateAviation #SportsEconomy #TheMasters #SuperBowl

Why We Started Media Companies for the Sports Business Crowd · Sid Balaga & Suraj Peramanu | The 4th Quarter X Under The Number

Brent Peus joins Sid Balaga and Suraj Peramanu of The 4th Quarter at their studio in the Courtside VC office for a crossover conversation on building new media properties for the sports business crowd. The 4th Quarter (newsletter + newscast, backed by Courtside) and Under The Number (media property of Skybox) represent two complementary bets on what's next for sports business media. Recorded in New York City. The thesis: there are roughly 100 people in their 20s who are going to run the sports business industry, and they all know each other. This is a conversation between three of them about the opportunity for a new generation of operators. What's covered: → Why TBPN became the template for niche business media and what its acquisition signals → The "100 people" theory of who actually runs sports business → Why legacy sports media companies can't ship new products at startup speed → Substack vs. Beehiiv vs. building your own platform → Research grade vs. entertainment-driven content and how to balance both → The case for building in public and shipping imperfect product → Turpentine, Erik Torenberg, and the playbook for stacking niche shows into a network → Why the next wave of sports careers will come from builders and emerging leagues, not the traditional path → Shoutouts to Patrick O'Shaughnessy, Molly O'Shea, Market Bubble, and the broader new media ecosystem. Guests featured on Under The Number include the McCourty twins, Cooper Manning, Seth Wickersham (ESPN), Kyle Rudolph (NFL / Alltroo), CiCi Bellis (Pro tennis, Cartan Capital), Marques Colston (Champion), Jason Illian (Dude Perfect / Highmount Capital), Terrence Murphy (Synergy Sports Capital w/ Reggie Bush), Pete Wilson (Grass League), Ryan Girardot (Cerebro Sports), and Dylan Robbins (Lucra). Subscribe to Under The Number: → Substack: https://undertheumber.substack.com → Spotify: https://open.spotify.com/episode/33jZvtNEiXYo6tMgDwhHJx?si=1W4SlhodQCiywBqIf3ZIJw → Apple Podcasts: https://podcasts.apple.com/us/podcast/under-the-number/id1730764733?i=1000769663455 Subscribe to The 4th Quarter:→ https://www.thefourthquarter.co/ #SportsBusiness #NewMedia #SportsMedia #CreatorEconomy

"Mother Nature is the Main Character" · Natural Selection Tour CEO Carter Westfall on Brand Building

Get off the sidelines—subscribe to Under the Number on Substack: https://underthenumber.substack.com/ Carter Westfall is the Co-Founder and CEO of Natural Selection Tour (NST), the outdoor action sports platform he's building alongside snowboarding icon Travis Rice. Joined by guest co-host Matthew Jester (CNC Partners), Brent Peus unpacks how NST is counter-positioning against the X Games (now owned by MSP Sports Capital under CEO Jeremy Bloom), Shaun White's Snow League, and the World Surf League (Dirk Ziff) by building a brand-first platform rather than a league. Carter walks through his winding career from Wall Street to the Sacramento Kings, the NBA league office under David Stern and Adam Silver, the Beijing and London Olympics, and the PAC-12's China expansion with Joe Tsai, before partnering with Travis Rice to fill the void in elite, mountain-based snowboarding competition. → Why Mother Nature is the main character of the NST brand → The Teton Ridge / TWG Global comp and why NST is a platform, not a league → How Red Bull, Yeti (Matt Reintjes, Bill Neff), and GMC came on as anchor partners → The three-bucket business model: content, experiential, and commerce → Inside the events: Revelstoke, Jackson Hole, Queenstown, Micronesia, and a South Africa surf event on deck → The destination hospitality fund ($30-50M) targeting heli operations and boutique adventure lodges → Powder Mountain (Reed Hastings), Patience Capital Group in Myoko Japan, and Bald Face as the comp → The "Natty Selects" derivative brand and a surf-meets-Survivor episodic concept with Skydance/Paramount → $15M raised across convertibles and a Series Seed, Series A closing mid-June → Matthew Jester on cultural capital, Rick Hess's CAA-to-TPG track record, and why NST fits the thesisWatch on Spotify → Listen on Apple Podcasts → Check out Skybox → https://www.skyboxmedia.com#surf #ski #bike #actionsports #UnderTheNumber #SportsBusiness Watch on YouTube → https://youtu.be/BHthoUe-BvU Watch on Spotify → https://open.spotify.com/episode/4mtedvVZPoLeQJwT5WQMra?si=E_ersxSnQv6lQHHEQOXotg Listen on Apple Podcasts → https://podcasts.apple.com/us/podcast/mother-nature-is-the-main-character-natural-selection/id1730764733?i=1000768576107 Check out Skybox → https://www.skyboxmedia.com #surf #ski #bike #actionsports #UnderTheNumber #SportsBusiness

The McCourty Twins' Playbook for Life After the NFL · Devin & Jason McCourty

Devin McCourty is an analyst for NBC's Football Night in America and Westwood One. A 2009 first-round pick from Rutgers, he spent his entire 13-year career with the New England Patriots before retiring in March 2023 — winning three Super Bowls, starting 205 games, recording 35 interceptions, and serving as team captain for 12 of those 13 years. A four-time Walter Payton Man of the Year nominee, he co-founded the "Tackle Sickle Cell" campaign with his twin brother Jason, raising over $2.5 million. Jason McCourty also played 13 NFL seasons, retiring in May 2022 after winning a Super Bowl alongside Devin in 2018 — making them the first twins to win a championship together. Drafted out of Rutgers in 2009, he now serves as a game analyst for CBS Sports and Westwood One, and is a regular on NFL Network's Good Morning Football. He sits on the Boston Medical Center Philanthropic Trust and co-founded "Tackle Sickle Cell" with Devin.Recorded at the Pro Athlete Community (PAC) Accelerate Conference, this conversation goes deep on the operator playbook: how the McCourtys screen deals, build personal brands, advise young players, and navigate the identity shift that comes when the game ends. On this episode of Under the Number, we cover: → The "black trash bag" moment and how Jason and Devin each processed retirement differently → How the McCourty's screen inbound deals and use their network of funds, family offices, and advisors as multiple sets of eyes → Why young athletes underestimate how much founders and operators want to talk to them → The personal brand playbook: be yourself, own your voice, build everywhere → Legacy 25: connecting venture capital to college programs in the NIL era → The earners-to-owners shift inside NFL locker rooms — and how NIL changed the conversation → The operators they look up to: Curtis Martin, Larry Fitzgerald, Marshawn Lynch, Pat McAfee, Cortland Finnegan→ What they're each looking forward to between now and the start of the season Get off the sidelines—subscribe to Under the Number on Substack: https://underthenumber.substack.com/ Watch on YouTube → https://youtu.be/4WjVTRPdxF0 Watch on Spotify → https://open.spotify.com/episode/1n2EC9V6Qtv3AjJ3kGvgeA?si=4t-K932zQ9u3c5OmSKFNgwListen on Apple Podcasts → https://podcasts.apple.com/us/podcast/the-mccourty-twins-playbook-for-life-after-the-nfl/id1730764733?i=1000767419347Check out Skybox → https://www.skyboxmedia.com/

$20 Million to Power Play · Dylan Robbins, Founder & CEO of Lucra

Dylan Robbins is the Founder & CEO of Lucra, the software company powering interactive competition for brands like Dave & Buster's, Five Iron Golf, and Chess Kings. In April 2026, Lucra announced a $20M Series B led by ARK Invest — the firm's first-ever lead investment in a startup. On this episode of Under the Number, we cover: → Why ARK Invest led its first-ever startup round (and why it wasn't AI) → How Lucra is rebuilding corporate loyalty as friendly competition → The pitch process: getting grilled by Cathie Wood and Nick Grous → Overcoming ARK's Skillz reticence and the B2B pivot that unlocked conviction → Building the engagement layer for offline competition at scale → Customer playbook: Dave & Buster's, Five Iron Golf, Chess Kings → What this investment unlocks for Lucra's next chapter Get off the sidelines—subscribe to Under the Number on Substack: https://underthenumber.substack.com/Listen on YouTube → https://youtu.be/84dPJgIoqFE Spotify → https://open.spotify.com/episode/5qcAisOxsUKSNIanbNesV6?si=1dTTAPzRRua02GrQQnhrIg Listen on Apple Podcasts → https://podcasts.apple.com/us/podcast/%2420-million-to-power-play-dylan-robbins-founder-ceo-of-lucra/id1730764733?i=1000766213712 Check out Skybox → https://www.skyboxmedia.com/ #Lucra #ARKInvest #UnderTheNumber #SportsBusiness #SportsTech