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Kill them with candor



After failing to secure another round of funding and shutting down my startup, Katch, I’ve been thinking about candor. While failure isn’t a unique story in our industry, talking about it is. Of course, I don’t advocate dwelling on one’s failures as a key to success, but paradoxically I found the quickest path to moving forward from my startup’s demise was to talk openly about it.

As founders, we’re often asked to perform — to sell our vision to investors, the press, conference panels and employees. The role the startup founder is asked to inhabit is limited, often closer to an action figure than to reality. We portray a childlike image of power instead of the dynamic and sometimes flawed human beings we actually are.

Unfortunately, when we deny aspects of our humanity, we run the risk of compounding the stress, anxiety and burnout we often feel under a mask of bravado. I’ve lived under that mask, and am happy to be free from it.

After closing Katch, I was introduced to Reboot, a firm that coaches founders to be more authentic leaders. Reboot and groups like it have spawned a growing community of founders who are having honest conversations about leading venture-backed startups.

Open dialogue and community have made two things clear to me. First, all startups, including well-funded and outwardly successful startups, are emotionally challenging for their teams. The stakes are high, the risk and uncertainty is palpable and all of this creates intense pressure throughout the company. Second, being open and honest about our experiences as founders and team members leads to a healthier and more fulfilling life than the one prescribed by always sucking it up and grinding it out.

20/20 vision

What does openness look like? I think these two posts by Matt Munson, CEO of Twenty20, are great examples: How I Burned 10 Million Dollars So You Don’t Have To and The Secret Suffering of Today’s Leaders. They’re brave and candid because they share real numbers, emotions and details that are rarely discussed.

Becoming someone you’re not

Pressure to perform starts early in an entrepreneur’s journey, often from the moment we decide to fundraise. James Routledge does an incredible job of capturing the hall of mirrors founders enter in How “killing it” is killing Startups.

“The danger is that the startup landscape is telling founders (and people working in startups) that they must live to impress others. It implies that they must perform every single day and that they must put on a show to win the affection of others who will define their success,” wrote Routledge. “I moulded myself on what VCs and advisors said, not on who I actually was or what I actually wanted to do.”

The pressure of raising money is so daunting that it’s easy to fool ourselves into believing that closing a round will solve all our problems. It won’t. Afraid to displease our investors, we hold ourselves captive to the promises we made at an earlier time in our company’s history. Casey Neistat, co-founder of Beme, jumps off cliffs and hangs from helicopters on an average day, but acknowledges that none of his daring feats scared him as much as launching his startup. He talks earnestly about the self-inflicted terror he felt running Beme before selling it to CNN.