The Bad Boy Startup

Upon returning to work in my 90% male engineering organization post-baby, it became clear that my pre-baby employer and I were breaking up. I wasn't ready for it, never expected it.

As most of us do after a long-term relationship ends: next, I overcompensated. You see, my pre-baby employer was a gigantic blue chip, a steady ship providing infrastructure and solid benefits, the classic Nice Guy. SteadyCorp. So naturally, I went for corporate America's version of the Bad Boy: a startup.

Oh, the Bad Boy Startup had all the appeal that SteadyCorp did not. It was fun - nothing serious! There were unexpected perks, huge decisions, too much of everything except anything resembling the real, rational world. I was caught up - who wouldn't be! - with the amazing food, the email blasts about acupuncture appointments available in the wellness center, the literal rock stars who would play on a Tuesday afternoon in the cafeteria. Celebrities - business and 'real world' - would appear next to you in the folding seat at a quarterly meeting, just before your queue to jump up and participate in a superheroine flash mob. The corporate debauchery was proudly on display. It was too good to be true.

I joined pre-IPO, when the company was in full hubris, with very few checks and balances. Here are just a few questions I never thought I would ask before my relationship with the Bad Boy Startup:

  • Our 10am meeting is delayed because... Jello shots?
  • Recurring, full-scale Nerf wars are 'a thing' in open office spaces? 
  • Does the always whirring sound of a remote control helicopter still appear in *your* dreams?
  • Per our boss, our 90% male team had 'too much green' in our quarterly goals (on a scale of green/yellow/red). So why did he change only my quarterly results from green to yellow?
  • Regardless of personal interest or business role, the entire company is 'strongly encouraged' to play games as a percentage of their work time?
  • Wait, the CEO hired another CEO to replace himself, without telling anyone at the company?

Needless to say my dalliance with the Bad Boy Startup didn't last too long. I couldn't really take it home to meet the folks, my friends (even my friends at other startups) didn't really understand the phase. While we were together, it was mostly amazing and fun; a set of experiences I wouldn't trade, personally and professionally. It was a chance to take San Francisco out on the dance floor as well. The City is such a great place to live, in my opinion for a finite period of time. Remind me to tell you the story about the party we ran into, on a Tuesday at a local dog park on a sunny Spring afternoon…

The people and community formed through the Bad Boy Startup, and our adventures in The City, were just some of what I gained out of our time together. From the helpful peers in my open space workplace that modified my Nerf cannons, to the creative characters on the #19 bus I took through the Mission, they all have helped me be truer to myself.

Here's to every Bad Boy (real or startup) that helps get us where we need to be. The tribulations that come with creating startups that reflect our own values, are worth the trials!