Entrepreneurs, Don't Be Afraid to Fail | Vinod Khosla (Khosla Ventures)
Key ideas
Khosla separates smart failure from dumb failure and tells founders to hold a big vision, test their plan in small experiments, and engineer their team.
From a machine transcript of the audio. Quotes link to the moment they are said.
- 1
Fail small enough to try again
Khosla's smart failure means risks where the win far exceeds the loss, run as learning experiments costing perhaps 10% or 20% of burn rather than 80%. He argues that being unwilling to fail means taking no risks and doing what everyone else does. He also estimates founders control at most four of ten factors in success, with the rest down to competitors and luck.
- 2
Hold the vision, flex the tactics
Khosla advises planning only the next three to six months and testing every assumption you can in the market, taking steps that each garner resources for the next. His analogy is a base camp on the way to Everest: a stable place to learn, which he warns VCs may push you to set up off the path. He believes people who raise too much money grow overconfident in their plan.
- 3
Use domain experts without letting them decide
Khosla says experience brings bias about how a sector works, so experts belong around the table while founder instincts drive the decisions. He cites Jack Dorsey saying only four of Square's first 200 people had done payments before. He blames one of his own failures, an early laptop startup, partly on hiring a CEO from IBM with the right credentials and none of the entrepreneurial instincts.
- 4
Recruit like it is the main job
Khosla says recruiting takes more of his week than anything else, and tells founders to work out what matters most to each candidate and then sell on that. He attributes the difference between a small and a very large startup almost entirely to attitude, culture and the gene pool engineered into the company.
- 5
Boards should challenge, not decide
Khosla, speaking of private companies, says a board sees a company only every six or eight weeks, so it should make founders think from other angles rather than make their decisions. He sometimes argues positions he doesn't hold for that reason. He treats replacing a CEO as the exception, and calls it mostly a bad recipe.
In Vinod’s words
“I'd rather have a high probability of failure and a large consequence of success than reduce risk to the point where my probability of success is high and the consequences of success are inconsequential.”
Vinod Khosla·Entrepreneurs, Don't Be Afraid to Fail | Vinod Khosla (Khosla Ventures)·Watch at 9:03(opens the original in a new tab)“Be obstinate about your vision, but be really flexible about your tactics.”
Vinod Khosla·Entrepreneurs, Don't Be Afraid to Fail | Vinod Khosla (Khosla Ventures)·Watch at 11:19(opens the original in a new tab)“I've never ever voted in 30 years on a board against a founder, ever. Other than one issue, which is when you have to hire or fire a CEO.”
Vinod Khosla·Entrepreneurs, Don't Be Afraid to Fail | Vinod Khosla (Khosla Ventures)·Watch at 4:18(opens the original in a new tab)About this entry
- Published
- Feb 13, 2015
- Channel
- Startup Grind
- Type
- Video
- Length
- 49:27
- Language
- English
- Added
- Nov 2, 2026
- Source last checked
- Nov 2, 2026
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Draft. Written by us with AI from a machine transcript of the video’s audio (Whisper) and checked against it. Machine transcripts can mishear; each quote links to the moment so you can hear it. Not yet rights-reviewed.
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