Episode #33
Inside The Mind of a Serial Entrepreneur | Jeremy Ostermiller | Episode 33 of The Racket House Podcast
SPIN Magazine board advisor and serial entrepreneur Jeremy Ostermiller on turning a $500 investment into a quarter billion dollar ad tech business, why he thinks artists still need press and PR in 2026, and why his CEO says AI will never break the next Nirvana. In this episode of The Racket House Podcast, Jon sits down with Jeremy Ostermiller, founder of Altitude Digital, co-founder of Edison Interactive, and Ernst & Young Entrepreneur of the Year for the Mountain Desert region. Before any of that, Jeremy spent his twenties as an independent concert promoter, throwing over 400 shows with everyone from Two Live Crew and Wu-Tang Clan to Snoop Dogg, Public Enemy, and more recently Shaquille O'Neal and Sublime. These days he sits on the board of advisors at SPIN Magazine, where he's helping lead a fundraise, acquisition strategy, and the brand's next generation, alongside running his coffee company Death Before Decaf and clothing brand Steeltown Garage. We get into the do's and don'ts of entrepreneurship, what it actually takes to start a business from nothing, where press and PR really fit into an artist's career today, how SPIN decides what to cover, where a limited marketing budget should actually go, and whether AI is something musicians should be excited about or scared of. If you've ever wondered what it takes to build, lose, and rebuild in business, or whether press still matters in 2026, this one is for you. Subscribe for more conversations with artists, operators, and industry professionals. Instagram: @therackethouse and @racketclubbb Work with me: https://www.therackethouse.com Newsletter: https://the-racket-house.kit.com/newsletter Join my Skool community: https://www.skool.com/music-careers-messy-middle My own tracks: https://open.spotify.com/artist/3hbZuTiNFxMjhgrt9AJKzT Free downloads & live sets: https://soundcloud.com/racket-club More on Racket Club: https://www.therackethouse.com/racket-club Chapters: 00:00 Intro 01:18 Jeremy joins, fresh off a Broncos loss 02:15 How Jon and Jeremy met three days earlier at a Lettuce show 02:44 College days in Fort Collins, throwing parties and getting evicted twice 03:34 Over 400 concerts thrown in the last decade 04:07 Booking Two Live Crew and breaking into hip hop promotion 05:50 Being a chameleon, staying authentic in a world that wasn't his own 07:23 The dirtiest show of his career and the fire marshal shutdown 09:23 MySpace Music, celebrity events, and Levitt Pavilion family shows 10:44 Picking artists off instinct before the data existed 12:41 Pitching Gannett on a video ad exchange and quitting the next day 13:40 Building Altitude Digital from zero to a quarter billion in revenue 15:56 Why advertising runs the world 17:04 From selling gum in elementary school to Steeltown Garage's 100,000th order 19:40 What they don't teach you about business in school 20:42 Knowing your weaknesses, going from micromanager to coach 22:09 The do's and don'ts of entrepreneurship 23:26 The first thing to do when starting a business 24:39 Why Jeremy skips market research and leans on pain tolerance 26:50 The biggest financial hit of his career 27:40 His honest advice for anyone starting a business in music 30:11 What Bob Guccione Jr. says made SPIN authentic 32:19 The superpowers exercise every creator should run 34:33 Why being a face in the place still beats chasing algorithms 35:49 The real meaning behind the band name Lettuce 36:18 What Twenty One Pilots taught him about fans vs. followers 38:35 Why humility separates artists with staying power 39:46 How he ended up on SPIN's board of advisors 40:44 What SPIN is building next, including the Live For Live Music acquisition 42:09 Why artists in 2026 are still asking about press and PR 45:04 How SPIN actually decides who gets covered 46:57 Whether a SPIN article can still be an artist's big break 49:41 Treating every show like it's the big show, the Shaquille O'Neal story 50:49 Where to put a limited marketing budget 52:28 Breaking it down to people, product, and process 54:08 Using AI for research without letting it write for you 57:04 Jeremy's favorite artists and go-to music 57:51 Would the music industry miss SPIN if it disappeared tomorrow 58:55 Would he start a media company in print today 1:00:26 Final thoughts and where to find Jeremy Jeremy Ostermiller, SPIN Magazine, Altitude Digital, Edison Interactive, entrepreneurship, music industry podcast, artist development, press and PR, music marketing, AI in music, concert promoter, independent artist, music business advice, dance music podcast, house music, founder interview, Death Before Decaf, Steeltown Garage #MusicPodcast #JeremyOstermiller #SPINMagazine #Entrepreneurship #ArtistDevelopment #TheRacketHousePodcast #MusicIndustry #MusicBusiness #AIinMusic #PressAndPR
