Rich Kleiman from bookie to power player in sports & media partnering with Kevin Durant| The Pivot

TL;DR

Rich Kleiman traces his path from college bookie to Kevin Durant's business partner, built on street hustle, music industry connections, and relationship-driven entrepreneurship.

Key Points

• 1.Kleiman's entrepreneurial instinct began in childhood chaos. Growing up in New York City with a mentally ill, substance-addicted mother and fighting parents, he sold toys and signed programs outside his building to earn validation and escape.
• 2.He became a bookie after one semester at Boston University. In 1995, he took bets on a Yankees-Mariners game, won when the Mariners covered, and quickly expanded his book to multiple colleges including Miami and Wisconsin.
• 3.Dropping out was survival, not strategy. He stayed in Boston running his book full-time after his father refused to keep paying tuition, telling him he didn't need a dollar — but he later called not finishing college one of his biggest regrets.
• 4.His music career launched accidentally through ESPN's 'The Life.' Hired as music supervisor because there was no producer role, he built an unsigned artist library, connected with Styles P and Pharrell, then managed DJ Mark Ronson, attending Tom Cruise's wedding and Calvin Klein shows.
• 5.Jay-Z and Fade to Black shaped his entire business philosophy. By connecting Jay-Z's manager John Manily to Radical Media, Kleiman produced the Fade to Black documentary and absorbed Jay-Z's lesson that every detail — including flyers — must reflect intentional taste.
• 6.He launched a hip-hop internet company in 1999 with a star-studded advisory board. Raising millions at age 21, he spent roughly half on a Hamptons launch party with Q-Tip and Mark Ronson DJing, and recruited Heavy D, Q-Tip, Robert De Niro, and Steve Stoute as advisors.
• 7.Meeting Kevin Durant was casual but immediately clicked. Mutual friend Wall introduced them when Durant was in New York for his Rookie of the Year trophy and wanted to attend a Jay-Z show; Kleiman says they simply 'fucked with each other' naturally.
• 8.Kleiman insisted Boardroom operate independently of Durant's name. He told KD he didn't want it to be 'Kevin Durant's media platform' — Durant should appear like gasoline when he wants to, not define the brand, so it could stand alone.
• 9.35 Ventures evolved from Silicon Valley investing to community real estate. After accessing world-changing startups in Silicon Valley, they shifted focus to real estate development throughout PG County, Maryland — where Durant grew up — which Kleiman calls purpose and legacy.
• 10.His mother's death last summer closed a lifelong wound. He took her to the ER roughly 15 times before 11th grade for overdoses, supported her financially through his career, and when she died felt a mix of sadness and relief — 'this is over' — because she never once got her life together.