New Shoes

When I was a kid, every time I got a new pair of shoes, I would challenge my sister to a race. She’d inevitably beat me, and I’d wonder what happened, totally gobsmacked. My mom had just bought me a sweet pair of new kicks, right?

Every startup wants to run faster, but most first-time founders have no idea how. I certainly had no clue.

It’s embarrassing to admit, but when I first set out to raise money for iDoneThis, I was so fixated on what needed to be done to raise money that I had no earthly idea what I would do with the money, once we got it, to accelerate our growth.

In part, this is because the answers came pretty easily. I parroted what I heard from everyone else—”I’m hiring engineers.” The problem is that’s nearly as facile as thinking that new shoes will help you run faster.

You run faster by transforming yourself—and certainly not by buying the latest pair of Air Jordans. They’re basketball shoes, after all.

When we finished our raise, we felt tremendous pressure to deploy capital. Obviously—that’s why we raised.

We were in such a rush that we started by hiring contractors instead of full-time employees. The worst part is that part of our rationale for it was nearly tantamount to increasing our cash burn as an end itself. We (1) didn’t know where the product needed love to increase leverage in our key metrics and so we had contractors build random junk and (2) failed to build institutional knowledge, skills, and equity that comes with hiring a full-time employee.

My cluelessness reminds me of when my sister looked me in the eye after one of our races and asked, “You know that new shoes don’t make you run faster . . . right?”

After a few months of not seeing any results, we ended our contracts, reassessed and righted the ship. We’d taken our lumps, digested our learnings, and came out changed and ready to grow.

Eventually, too, I started running a lot faster. Much faster than my sister. I have puberty to thank for that.