Fail Week: Max Levchin’s ‘Doomed’ College Startup That Maxed Out His Credit Cards (And Got Him Dumped)

The road to big, shiny success is often paved with quite a few failures. But for whatever reason, we in the tech press concentrate much more on stories about the big wins in the industry, and we tend to ignore the many losses incurred along the way. This is something that needs to change — people going through tough times in building a business should know that they’re not alone.

So TechCrunch TV decided to declare this week “Fail Week,” and run a five day long video series in which we talk to some of tech’s most famously successful people about the darkest days in their careers when everything seemed to be going wrong.

This final episode features Max Levchin, who is of course known for co-founding such blockbuster businesses as PayPal and Slide and serving on the boards of companies including Yelp and Yahoo. But it turns out that not all of Levchin’s companies have turned into slam-dunk successes.

Watch the video above to hear about the “doomed” startup Levchin co-founded in college that left him with several maxed out credit cards and thousands of dollars in debt. The company’s drawn-out failure came with some humiliating moments — a road trip from hell, a painful rejection from a potential investor, and an ugly breakup with a girlfriend who determined that Max cared more about his servers than about her.

You can watch all of our Fail Week stories here.