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

November 4, 2026 · 58 min

🎙️ Full episode

0:00 / 58:15

DEBRIEFWritten and voiced by AI from the episode's audio

Scott Kupor, former managing partner at Andreessen Horowitz and now director of the U.S. Office of Personnel Management, reflects on building a16z from scratch in 2009 during the financial crisis and shares how he's applying venture capital principles to fix the federal government. Starting as a16z's first employee with no job description, Kupor helped implement Michael Ovitz's CAA model—disaggregating the general partner role into specialized teams providing entrepreneurs with networks, talent, and business development support. This "platform" approach, combined with aggressive marketing in an industry that traditionally shunned it, enabled a16z to raise subsequent funds on the momentum of early wins like Skype. Today, Kupor is tackling systemic government problems: attracting young talent through merit-based hiring and two-year programs like TechForce, modernizing Byzantine processes (like digitizing 400 million retirement documents stored in a Pennsylvania mine), and creating performance incentives that reward risk-taking. His core thesis is that organizations—government or private—succeed when they have the right people, clear objectives, and incentives aligned to those objectives.

🎧 AI Debrief

0:00 / 5:49

Read the debrief

Show notes

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

Chapters

() Quitting HP mid-financial crisis to join a16z

() His first day

() How a16z copied Michael Ovitz's CAA playbook

() After-hours bourbon in Marc Andreessen's office

() The Skype deal that returned half the first fund

() Why VCs thought marketing was beneath them