Hard things about startups, pt. 1

Seeing the top of the hill

I was bad at bicycling when I was a child. There was this big hill in front of my house, and it scared me, so I hated bikes throughout my life. In college, however, I had a long walk to campus, and one day I literally found a bicycle in our backyard. (We also found a homeless man doing laundry back there once too.) So I started biking, and it wasn’t so bad.

My roommate at the time was an awesome biker, good enough to be on the Berkeley bicycling team, and got me into “real” cycling. Our first “real” ride was up Tunnel Road / Grizzly Peak.

It’s classified as a “beginner” route, but I don’t remember anything harder than the first time I rode the hill. Here’s an excerpt from the official description on http://cycling.berkeley.edu/routes/easy/grizzly-peak:

This is an easy beginners ride. It starts up Tunnel Rd. like most rides from Berkeley. Tunnel Rd. climbs steadily at an average 5% grade for about 4 miles…

The first time you ride this road, you don’t know where the top is. 4 miles of a steady climb can be heart-wrenchingly grueling. Two of the worst feelings: 1. Trying to downshift and making the horrifying realization you’re already in your lowest gear, and 2. Cresting an uphill turn and seeing nothing but more uphill.

I think the hard thing with startups is that you never know when you’re at the top of the hill. It just seems endless, and it’s crushing to give everything you got to just get to the next uphill turn, only to realize there’s potentially infinitely more uphill. Maybe you’ve already worn yourself out; who knows if you’re only 1% of the way there? You keep telling yourself it’s just a few more turns, but it’s easy to spiral into wondering if there are really five hundred or five million left.

That’s why the second time biking a hill is so much easier than the first. It’s all in your head, really.

We started out with four co-founders at FitStack. At each mile, we’ve lost people, and I’m sad to say starting next week I’m going to be working solo. I wish I had a map proving we’re just a turn or two away from hitting the top of the hill, but I don’t.

(The bright side of this is that if my metaphor is correct, and each co-founder symbolizes a different mile, I must only be a mile away. Logic, son.)

I hope the ride gets easier: a few months after my first tortuous ride up Grizzly Peak, I was jammin’ the 18 mile ride between classes. This led to another lesson from my roommate Spencer: the race doesn’t stop at the top of the hill. But we’ll save that for a future post.

For now, I’d just like to congratulate my co-founder and friend James on his new position: he starts Tuesday at Zenefits. I was lucky enough to meet a few of his future co-workers and loved their energy and enthusiasm. They’re solving a real problem that resonates with James’ soul. He’s always wanted to get into Operations/HR/Enterprise/Leadership, and now he’s … leading a team of operations people at a company that does HR for corporations. He’s the Shimano SH-R170 shoe to their Shimano Dura-Ace PD-9000 pedal.

James will only be a block away, so we’re going to go get lunch all the time and he’ll be abreast of FitStack as it takes over a company near you. James, I’ll keep the lights on at james@fitstack.co. Thanks for the awesome ride so far, buddy.