Day of the Dead: Postmortems of Silicon Valley Failures

The most famous startup stories often have storybook endings: founders hatch daring and disruptive ideas, secure funding by venture capitalists, create billion dollar companies, and change the world. But for every big success, there are many more tech companies that fail.

Silicon Valley is unique in its toleration--and even celebration--of failure. Failure is not a badge of honor for its own sake, but an acceptable cost on the way to success: “Fail fast. Succeed Faster.”

Even entrepreneurs known for being winners go through failures of many stripes--fizzles, flops, false steps, even frauds. Some are permanent; others are hard-won lessons on the way to the next big thing.

What can we learn from some epic (and more quiet) failures? What differentiates between productive failure and fatal failure? What signs should entrepreneurs heed to declare a failed product, service, or start-up dead? In dark times, what are effective strategies to re-boot? How do the best failures yield valuable lessons and spawn something new?

Justin Kan is an internet entrepreneur and partner at seed fund Y Combinator. Justin has founded many companies including: Kiko, the first AJAX web calendar; Justin.tv, a live video streaming platform; Socialcam, a mobile video sharing app (acquired for $60mm by Autodesk in 2012); Twitch, a video game streaming platform (acquired by for $970mm by Amazon in 2014); and Exec, an on demand maid service (acquired by Handybook in 2014).

Kim Polese is a technology entrepreneur and business leader. She currently serves as Chairman of CrowdSmart, a collective intelligence platform that accelerates startup traction and funding and helps investors identify promising startups. Kim is also Chairman of ClearStreet, whose employer-sponsored financial wellness platform makes healthcare more affordable and helps people build longterm financial health.

Kim has an established history of working on ground-breaking technologies. She began her career at IntelliCorp helping Fortune 100 companies use AI expert systems, and later moved into product management at Sun Microsystems where she led the launch of Java in 1995. Kim then co-founded Internet software pioneer Marimba, serving as President, CEO and Chairman and leading the company to profitability, an IPO and a successful acquisition by BMC.


Bill Reichert is Managing Director of Garage Technology Ventures. Since 1998, Bill and Garage have helped many great companies get their start, including Pandora Media, LeftHand Networks, Kaboodle, WhiteHat Security, Tripwire, and D.light Design. Prior to co-founding Garage, Bill was a co-founder or senior executive in several venture-backed technology startups, including Trademark Software, The Learning Company, and Academic Systems.

Join us as Silicon Valley veterans Justin Kan, co-founder of Twitch, Kim Polese, Chairman of CrowdSmart, and Bill Reichert, managing director of Garage Technology Ventures, share postmortems of their industry successes and failures.