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Introducing 'Confounded': Startup Stories From the Brink of Failure (Video)



"Move fast and break things" was a motto that worked for Facebook, at first. Mark Zuckerberg politely left it behind in 2014, ceding a piece of the company's early swagger to users' need for "stable infrastructure." At the time, he talked about the technical debt cost of going back to fix bugs. He didn't talk about the human cost of Facebook's famous early mantra, because few people ever talk about that.

Burnout, anxiety and depression are common among entrepreneurs. Few studies exist, but a UCSF professor's 2015 survey of 242 entrepreneurs found 30% of respondents said they have a lifetime history of depression, significantly more than comparison respondents. In the past four years, anecdotes have emerged as well, with high-profile entrepreneurs coming forward to talk about the issue.

Confounded is a series of video interviews with entrepreneurs that goes beyond the heroic postmortem.

"Failure has become OK--it's even a kind of street cred--as long as you can write the postmortem blog post about your heroic pivot," venture capital investor Brad Feld wrote in a 2013 post for Inc. in which he talked about his own bouts with depression.

"Confounded" is a series of video interviews with entrepreneurs that goes beyond the heroic pivot postmortem: Not the clear-sighted looks at what went wrong, but the recollections that are painful and don't cover anyone in glory. The first, a pilot, is an interview with Dave Balter.

Feld's post on depression followed the deaths by suicide of entrepreneurs Aaron Swartz and Jody Sherman, which brought new attention to the issue of depression and suicide among entrepreneurs. One of the best is Alexia Tsotsis' TechCrunch post, "'Killing It' Isn't Worth It." Other testimonials have come out since, including this one from Moz founder Rand Fishkin, penned just after he spoke at HubSpot's Inbound conference in Boston.

Many of the voices--and many of the victims, it seems--are men. But in a 2015 article for Quartz on depression and women CEOs, Jules Pieri, chief executive of Boston-based The Grommet, wrote about her own experience with depression. As she prepared for a recent surgery that required general anesthesia, "believe it or not, I genuinely looked forward to being knocked out because I knew that it would, at least for time, give me a break from my responsibilities."

There are many stories like these, and not just about depression, but always about the awkward, confounding moments that face any entrepreneur and are rarely the stuff of stories about breaking through walls. With those stories in mind, Keith Frankel, a serial startup executive in Boston, came up with the concept for "Confounded" and brought it to me at BostInno.

Balter is a serial entrepreneur based in Boston whose past successes (BzzAgent, Smarterer) have made him sought after among investors and peers here. In our pilot episode, below, Balter talks candidly about his retreat into a kind of depression--though he doesn't use the word--after hiring people more competent than he was, himself. (It's a topic he's addressed before.) He talks about raising VC, management skills and losing employees' trust with the way he handled layoffs. And he talks about selling the company and the compulsion to do it again, which he feels even in the very early stages of his new company, Mylestoned.

The entire interview is below, hosted on BostInno's YouTube channel. We'll also be releasing short takes from it on Facebook & Twitter, which you can find under the hashtag, #BostInnoConfounded.

The impact of these stories may be important not just for individuals who struggle privately with the same issues, but for venture-backed technology as a whole. As Fortune's Erin Griffith noted in a post last month, real attitudes about failure and success have seeded creeping fraud among Silicon Valley companies. “The whole ‘fake it till you make it,’ ‘move fast and break things’ attitude—all those sorts of battle cries are misinterpreted by some folks into making things up,” Jakub Kostecki, founder of due diligence consultancy StartupFactCheck, told Griffith.

So it seems tech in 2017, like Facebook in 2014, needs a new motto. "I think that 'back to technology' should be the motto for the next 10 years," wrote the initiator of a Hacker News thread on the topic of Jody Sherman that has 128 comments.

As we're entering a new year, "Confounded" will take a frank, and sometimes humorous, look at the very personal difficulties underlying the mottos founders have posted on the walls of startup workspaces. We hope that by examining these issues avoid a kind of human technical debt that can never be repaid.


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