a16z's First Employee on the History of a16z, Venture Capital & Fixing the Government | Scott Kupor

Scott Kupor is the director of the U.S. Office of Personnel Management (OPM), which serves as the HR and talent agency for the federal government's roughly two million civilian employees. He worked with Marc Andreessen and Ben Horowitz at Loudcloud and Opsware, which sold to Hewlett-Packard in 2007. In 2009 he became the first employee of Andreessen Horowitz, where he spent 16 and a half years as managing partner, building the firm's operations and later investing in later-stage healthcare companies. Scott explains how a16z adapted Michael Ovitz's CAA model to venture capital, how the Skype deal and a willingness to market in an industry that considered it taboo accelerated the firm, and why he had to set his ego aside as the firm grew. He also shares why he left for government, why its incentive structure is "completely screwed up," how OPM is changing performance ratings and promotion rules, and how programs like Tech Force aim to bring young talent into government. He also tells the story of the underground mine in Boyers, Pennsylvania, where federal retirement paperwork was processed by hand for decades. Show notes: https://www.davidsenra.com/episode/scott-kupor Made possible by Ramp: https://ramp.com Deel: https://deel.com/senra AppLovin: https://applovin.com/senra David Senra X: https://x.com/davidsenra Instagram: https://www.instagram.com/davidsenra LinkedIn: https://www.linkedin.com/in/davidsenra Facebook: https://www.linkedin.com/company/senrashow Threads: https://www.threads.com/@davidsenra Spotify: https://spti.fi/TVrr557 Apple Podcasts: https://apple.co/4msoZtb Website: https://www.davidsenra.com Scott Kupor X: https://x.com/skupor LinkedIn: https://www.linkedin.com/in/scottkupor Chapters 00:00:00 Quitting HP mid-financial crisis to join a16z 00:01:37 His first day 00:04:00 How a16z copied Michael Ovitz's CAA playbook 00:10:18 After-hours bourbon in Marc Andreessen's office 00:13:31 The Skype deal that returned half the first fund 00:18:37 Why VCs thought marketing was beneath them 00:21:48 Swallowing his ego as a16z grew 00:27:12 Why he left a16z to run the government's HR 00:30:37 Why government is afraid to take any risk 00:33:24 Why 99.7% of federal employees get a passing grade 00:36:13 Recruiting 1,000 engineers into government 00:38:37 Only 7% of the federal workforce is under 30 00:40:31 Why "a job for life" is the wrong pitch 00:43:09 Why the government would never have hired Big Balls 00:46:39 Why DOGE had to be a big bang 00:48:56 The underground mine with 400 million pages of paper 00:55:28 Why government has to accept some failure 00:57:14 How young people can join

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