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
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