Head of Product
“The maturation plot — the plot about growing up — is one of those strongly optimistic plots. There are lessons to learn, and those lessons may be difficult, but in the end the character becomes (or will become) a better person for it.”
This story begins in the fall of 2016, when I was on the phone with one of my investors and closest mentors. We were talking about Hardbound’s progress and funding situation, and he made a suggestion that, I must admit, I was not a big fan of at the time:
“Have you considered applying to Techstars?”
I had not.
In my view, startup accelerators were not a smart choice. They take a large equity stake in your company (6%) for a minimal investment (20k) and justify their steep price by giving you lots of “advice” and plugging you into their “network.”
It wasn’t that I was greedy to keep the largest ownership stake as I possibly could. This is my first company, and I wanted to partner with the best people possible. I knew we had a lot to learn and couldn’t do it by ourselves. If that relationship was going to be truly aligned, I wanted them to have equity.
The problem, in my mind, was that we had all the advice we needed. Possibly even too much advice! We had a great crew of investors who had bet on us in our pre-seed round, and at this point we just needed to execute. I thought it would be a huge distraction to go through some kind of accelerator program.
But there was something else, too.
I’m a bit of a lone wolf. I’m not really a “group” person. Every time I used to see something like “Founder of _______, (YC S12)” on a founder’s Twitter bio, it made me think they had an emotional need to belong to some sort of group. To display that badge of honor as proof that their unknown startup is really actually quite special.
So when I was on the phone that day with our mentor, and he suggested that we apply to Techstars, I didn’t give it serious consideration.
“The protagonist of the maturation plot is usually a
sympathetic young person whose goals are either confused or not yet
quite formed. He floats on the sea of life without a rudder.”
Our app was doing pretty well, but growth wasn’t exactly explosive.
Apple featured us as a “best new app” and Fast Company named us one of the top 10 apps of 2016, so we were getting a pretty solid stream of downloads, but it all felt completely beyond our control. It was like we were dependent on lighting strikes from heaven, when someone with a big audience decided they liked us.
We were spending 90% of our time just executing, and not very much time on investigating the big questions. We didn’t believe that any kind of structured work process would make that much of a difference, so we just had ad-hoc conversations whenever one of us decided there was something to say.
Our bank account was slowly dwindling, and I knew we’d need to do something about that soon.
So I scheduled a wave of phone calls with potential seed round investors to take their temperature. Some people loved us, others thought our idea made no sense. I remember one meeting where a VC literally told me “this just isn’t an exciting opportunity.” Gotta give her points for honesty!
I was encouraged at first by some of the conversations, but the deeper I dug, the more clear it became that we were not quite ready for a seed round. They were rooting for us, but not even close to pulling the trigger.
Our plan just wasn’t crisp enough to invest in without off-the-charts growth.
I didn’t know what to do.
“He often vacillates, unsure of the proper path to take, the proper decision to
make. These inabilities are usually the result of a lack of experience
in life — naivete.”
At some point in this process, I reluctantly concluded that it was going to be very hard for us to raise a seed round.
Joe (my cofounder) and I were talking about it at work one day, and Techstars came up. They invest in companies at the earliest possible stage, so we figured we’d have a much better chance with that than raising a big seed round (something that many startups do after they go through an accelerator program).
We went to the Techstars website and started poking around, to try to learn more.
The application was due in two days. Shit.
We spent that whole afternoon gathering the data they asked for, crafting answers to their questions, and recording a quick video.
I still wasn’t sure I wanted to do it.
“Which brings us to the test. The catalytic event. Suddenly something comes along and smacks [him] square in the face. The event must be powerful enough to get the attention of the protagonist and literally shake up [his] belief systems.”
After a couple of weeks passed, we got some good news: our top 2 choices (Techstars NY and Techstars Boulder) both wanted to interview us.
We had the calls, and discovered that we got along really well with the Techstars Boulder crew, but we had slightly less chemistry with Techstars New York.
This was kind of a bummer to us, because our company was located in New York, and Joe and I were both reluctant to move to Boulder for 3 months and be apart from our girlfriends / lives.
Another week passed, and we got an email: we didn’t get into Techstars New York. Shit.
Side note: isn’t it funny how even when you’re not sure you want something, it hurts when you don’t get it?
Then we got another email: Techstars Boulder wanted to have a second phone call. I still wasn’t sure I wanted to do it, and was honestly kind of leaning against it. So I saw this call as our opportunity to talk through all our concerns with them. Based on our first call I knew I liked them a lot, and I wanted to give them a chance to change our minds.
We spilled our guts, basically. We said we weren’t sure about giving up 6%, we didn’t know how to value the “advice” and “network”, and we didn’t really want to leave New York. They gave us a list of alumni to talk to.
I got on the phone with some founders from previous cohorts, and they told me all about how big an impact Techstars had made on not just their company, but their lives. I pressed for details. It seemed to add up.
I was torn.
Will this really make us grow faster?
Don’t we already know what we’re doing?
We just need to execute a little better!
Nobody knows more about our challenges than us.
Maybe that’s true, but why aren’t we growing faster?
Why does it seem so hard for us to raise a seed round?
Maybe we don’t know what we don’t know…
A couple days later, we got an email.
“It may be, in fact, that your protagonist is actually trying to do the right thing, but doesn’t know what the right thing is. That means trial and error. Finding out what works and what doesn’t work. That is the process of growing up, the journey from innocence to experience.”
That night I went home and talked to Sonia (my fiancee) about it. I thought maybe we should do it, but I wasn’t sure. The only thing I was certain about was that it would really suck to be apart for 3 months. She told me that if I thought it was the right thing for Hardbound, that we should do it. That meant a lot to me.
The next day, Joe and I went on a walk.
It was hard for me to admit to him that I wanted to do it. Partly this was because I didn’t want to admit I was wrong. But also because I knew it was a lot to ask of him, to move to Boulder for 3 months.
I was nervous, but I said I thought it would be a good idea. I thought we could probably learn a lot from them. It might even be worth 6% of the company. Maybe.
“Yeah, I think you’re right. We should do it.”
I honestly wasn’t expecting that. But as we continued on our walk through Greenwich Village, and started to turn back towards the office, it became clear that we both knew it was time for us to level-up.
It was decided.
That was back in December.
It’s now Saturday, February 4th, and I’m sitting in our Airbnb at the kitchen table, reflecting on the two weeks that have passed since Techstars started.
If I’m being honest with myself, I have to admit that we’ve learned more in the past two weeks than we did in the previous six months. But the bulk of the learning hasn’t been specific to our product or market. Instead, we’ve been learning how to learn.
After going through the “foundational” lectures and exercises, doing team thought experiments, and talking to literally hundreds of smart, experienced people about our business, I think I realized what was holding us back before. The big mistake we were making actually turned out to be pretty simple:
We were sloppy.
Not with our product, but with our learning.
In my past I’ve operated mostly on intuition, and a lot of times I have been proven right. This has taught me the wrong lesson: just hack it together, ship it as quickly as possible, and everything will work out fine. You can always adjust from there if need be. Usually I just liked to charge forward.
In the words of Stephen Covey, I was investing all my time in Production and none of my time into Production Capacity. I was constantly chopping wood but never stopping to sharpen my axe.
I used to think that team meetings with whiteboards and post-it notes were “playing house” and scoffed at them. I used to think it wasn’t worth the time to have a weekly OKR meeting, or a daily standup. I’ve only seen extremely watered-down versions of these in my prior working experiences, so I just had no idea how powerful they can be if done well.
Turns out, they can be pretty damn powerful!
The bottom line is this: Techstars has taught us to be disciplined and focused. Not because they’ve said anything we haven’t heard before, but because they’ve shown us how to do it, and given us brutally honest feedback on our form.
It’s like the difference between reading a book about tennis and joining a full-time program where you dedicate 100% of your time to improving your tennis game, with constant feedback from multiple master coaches with various specialties. I don’t care how smart you are, you’re going to do significantly better if you put yourself this kind of environment.
Now that I think about it, I’m frankly a bit embarrassed we didn’t apply sooner!
But that’s life, right?
If you’re not embarrassed by how naïve you were six months ago, you’re not learning fast enough.
An infinite amount of thanks to Natty and Julie at Techstars, who brought us into the family and took a chance on us and our crazy idea. We are so grateful for everything you do! 🙏🏼
Create your free account to unlock your custom reading experience.