Thursday, December 31, 2015

Permission to Fail

[ed. At least the title is accurate. Jeezus. I don't mean to take it out on poor Michelle here because there are so many, many, other posts like this on the internet (*cough*, Medium), she just happened to have the unfortunate luck of popping up on my screen today. I have to say, if I see one more angst-ridden, pseudo-motivational article about some young person wrestling with a new career or business (oh, sorry... "startup") I'm going to scream. Just STFU! Please. Do your job, learn what you can and leave it at that. None of this hand-holding and "be brave" posturing will get you anywhere, except maybe with your co-workers who now have a better idea about your insecurities and can act accordingly. Do you think the heavy rollers at Sequoia Capital have time for this, or even care?]

People write a lot about the emotional rollercoaster of startups. Turns out, that roller coaster doesn’t slow down after year 1, 2, or 3. I know firsthand that the metaphor doesn’t go away after you hit 100 or 500 paying customers, after you’ve been backed by Sequoia Capital, or after you’ve captured millions of dollars in revenue. The roller coaster climbs higher, making the drops all the more terrifying. Slack’s CEO sums it up pretty precisely:

“Now that we’re on this crazy success trajectory, the degree of stress and the degree of doubt and the degree of second-guessing hasn’t been reduced at all,” he said. “In many respects, it’s actually worse now because there’s more at stake. […] I think I wake up every day and look in the mirror and say, ‘We’ve almost certainly fucked this up completely.‘” - Stewart Butterfield, CEO, Slack

One thing I’ve noticed is that it’s easy to write and to be transparent when things are going great. It’s harder when the roller coaster dips downward, when your stomach feels like it’s in freefall. Way back in January, our team experienced one of those dips. Up until this point, for 24 straight months, Keen IO’s business had grown 5-15% - every month! We were embarrassingly confident, and we felt unstoppable. It was coming off of this incredible rise that reality hit and we got to experience a little more of that roller coaster everyone was talking about.

I wrote the following company-wide memo during that time, when we got to learn what it was like to fall a little bit.

On Tue, Feb 24, 2015 at 5:55 PM, Michelle Wetzler wrote:

Hey everybody - I hope you don’t mind me sharing a relatively raw piece of writing. It started out as a sort-of blog post, but then I realized it’s really a letter to you all. Feeling a bit brave right now and clicking send. Hope it’s helpful.

by Michelle Wetzler, Keen |  Read more:
Image: Imgur