Where Failure is an Option: San Diego’s Startup Culture as a Bay Area Annex

Not long ago, one of my Xconomy colleagues in Seattle posted a provocative piece about startup failures and suggested the startup culture in some cities—especially the San Francisco Bay Area—is far more tolerant of technology entrepreneurs who fail.

Greg found that many Seattle entrepreneurs say they feel stigmatized by startup failures in the Pacific Northwest (does all that winter drizzle make them more pessimistic?). Seattle VCs, on the other hand, take a milder view. In Boston, the startup culture apparently has an attitude, at least the way it’s described by Brad Feld, who has been investing nationally for the past 15 years (and who co-founded the TechStars seed-stage startup program and the Foundry Group in Boulder, CO). Feld says, “One of the reasons I think Boston has resurged as such an entrepreneurial community, in a good way, in the last couple of years, is it had a massive chip on its shoulder.”

In the Bay Area, the kingdom of heaven for venture capital, Greg heard (at least from outside) that failure is considered a badge of honor—which makes it sound like collecting an Eagle Scout badge for entrepreneurs.

San Diego’s startup culture, however, was largely unrepresented that day. So I conducted an informal survey of local VCs and entrepreneurs and discovered to my surprise that many view San Diego as a kind of venture annex of the Bay Area—especially as San Diego’s hometown venture firms have faded in recent years.

“I think San Diego is more like the Bay Area than Seattle,” says Jeanine Jacobson,” a San Diego-based partner of the Founder Institute’s startup incubator and mentoring program. “There is a quote that everyone can relate to: ‘Good judgment comes from experience, but experience comes from bad judgment’ and entrepreneurs are no exception to this rule. All one has to ask VCs is who would you rather invest in—a first time entrepreneur or an entrepreneur who has had a past failure?”

Marco Thompson, who founded Wind River Services (which was acquired earlier this year by Intel) and is managing director of San Diego-based Express Ventures, was among several who linked San Diego’s startup culture to the Bay Area. “Financing for San Diego technology companies comes principally from the Bay Area, and not at all from Seattle,” Thompson says. “So we are clearly infected with Bay Area attitudes, and are very tolerant of previous failures.” Thompson adds, “My attitude, and the attitude of many investors that I know, is that ‘an entrepreneur learns more in a failure than in a success.'”

Abi Barrow, who has years of experience with startup programs in both San Diego and Boston, says, “While I am not sure that failure was a badge of honor in San Diego, it was certainly accepted and not held against you if you

Author: Bruce V. Bigelow

In Memoriam: Our dear friend Bruce V. Bigelow passed away on June 29, 2018. He was the editor of Xconomy San Diego from 2008 to 2018. Read more about his life and work here. Bruce Bigelow joined Xconomy from the business desk of the San Diego Union-Tribune. He was a member of the team of reporters who were awarded the 2006 Pulitzer Prize in National Reporting for uncovering bribes paid to San Diego Republican Rep. Randy “Duke” Cunningham in exchange for special legislation earmarks. He also shared a 2006 award for enterprise reporting from the Society of Business Editors and Writers for “In Harm’s Way,” an article about the extraordinary casualty rate among employees working in Iraq for San Diego’s Titan Corp. He has written extensively about the 2002 corporate accounting scandal at software goliath Peregrine Systems. He also was a Gerald Loeb Award finalist and National Headline Award winner for “The Toymaker,” a 14-part chronicle of a San Diego start-up company. He takes special satisfaction, though, that the series was included in the library for nonfiction narrative journalism at the Nieman Foundation for Journalism at Harvard University. Bigelow graduated from U.C. Berkeley in 1977 with a degree in English Literature and from the Columbia University Graduate School of Journalism in 1979. Before joining the Union-Tribune in 1990, he worked for the Associated Press in Los Angeles and The Kansas City Times.