Sunday Conversation #7: Keith Rabois, Khosla Ventures

Keith Rabois

Welcome to the seventh “Sunday Conversation,” this week featuring Keith Rabois of Khosla Ventures. Many of you reading this will already know of Rabois and follow his tweets closely. Rabois is arguably one of the very best early-stage technology angel investors and holds deep operational experience at some of the Valley’s signature companies. Below is our seven-part discussion covering the transition from angel investing to venture capital, how he sources information and people at the edge of his network, his thoughts on Bitcoin and AngelList, the influences on his investing style, and much more. As always, Rabois is unflinchingly clear in his beliefs about technology and startups, and this conversation only underscores his reputation for being direct. ♦

Part I, Transition From Angel To Institutional Investor (3:24) — Rabois marks a line between amateur investing (amateur) versus professional investing (venture capital), and the various ways time becomes the ultimate scarce resource. ♦

Part II, Filtering Options in Venture Capital (1:43) — Rabois explains why traditional filters may often fail in venture capital, where outliers are the ones who historically create the breakout companies, contrasted with executive or operational recruiting, which relies more on a standardized set of qualifications. ♦

Part III, Investing In People Early, Even Pre-Product (2:20) — Rabois explains why he takes a different approach to investing in an efficient market, especially on evaluating people (which is more vague) versus evaluating metrics (which most people can understand). ♦

Part IV, How Founders Get Time With Rabois (3:25) — Rabois explains how he handles introductions and referrals, as well as how he takes cold pitches on email or even Twitter, as he keeps some time open to meet people who don’t have deep networks to him. ♦

Part V, Thoughts On AngelList (5:16) — Rabois has a nuanced view on AngelList. He was one of the first angels to adopt the platform, and shares his predictions on how the platform will play out in the U.S. and overseas. ♦

Part VI, On Bitcoin, A Currency And Protocol (5:47) — Rabois delineates between Bitcoin, the currency, and Bitcoin as a protocol. With respect to the currency, Rabois believes Bitcoin will not take off in the U.S. because of government intervention, whereas the currency will likely grow in importance in areas worldwide where the rule of law is weak. ♦

Part VII, On The Hype Cycle (4:01) — Rabois explains how the transition to mobile is still underhyped, why Instagram would’ve beat Facebook if they remained independent, how the iPad is going to relegate laptops to limited professional use cases, why some companies are potentially overvalued today, and other technology predictions. ♦

Audio Recording, Full Conversation via SoundCloud

A special thanks to the team at Scaffold Labs for sponsoring the Sunday Conversation series on Haywire. Scaffold Labs is a boutique technology advisory firm based in Silicon Valley which designs and builds scientific and predictable talent acquisition programs that helps technology startups hire great people. Scaffold Labs has previously partnered with companies such as Cloudera, Appirio, and Nimble Storage, among others. For more information, please visit