Startup step-by-step: Why I’m doing another startup

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Mailbox founder Gentry Underwood on productivity, collective intelligence and building a $100M email app

The desire to create is a hard one to kill. I’ve had it all my life, from the comic books and music I made with my grade school friend Rick to the books I wrote and tried to write to the projects I built over the years. Now it’s become easier and, in a way, harder, to make something meaningful online, so after shutting down one startup last year, I’ve decided to work on another one, Jaywalk, with a new team.

My first startup was a deep learning experience. I learned about entrepreneurship firsthand, experienced the ups and downs (mostly downs) of building, raising and, ultimately, folding a company. I watched one friendship bend and another break under the unique pressures of dreaming something and watching the dream choke.

It sucked.

After all, I thought I was special. I’ve written about startups for a long time and I was flip and funny and ignorant of the pain people have to go through in order to make something real. Sure, I had an academic understanding of the topic  —  seed rounds, angels, development, media pushes  —  but I had no real idea what all that looked like in practice. I like to think that’s changed and at the very least I’ve been given a more sober vision of the future.

The tech media have made startups seem like a real blast. You hang with your friends, write a little code and cash a check. When you’re young you can survive on ramen and heavy metal and you walk away unscathed, the hero of an action movie walking away from an exploding helicopter.

But the truth is far more interesting. First the average and median age of most U.S. startup founders is 39. While we mostly hear of the young founder straddling the world, what you rarely hear about is the older founder with years under their belt with an idea that will change an industry that they understand implicitly. The best startup founders don’t “disrupt,” per se. They improve. The byproduct of that aggregated improvement is disruption.

Building things has also made me more compassionate. I used to run around the world yelling at people to quit their jobs, to get things done, to move fast and break things. No longer. I understand the value of a side hustle and the importance of research and planning. I also understand how rare startup success is and I try, in my own way, to assuage the grief of a new founder in a distant city who is finding out, as I did, that the world is cold and unfeeling and uninterested in your idea until, one morning, it isn’t. It’s the expectation of the breakthrough that has to sustain you through arguments, failures and deafening silence.

I understand the dangers and benefits of VC, the pride that some people have at bootstrapping, and the importance of the entrepreneurial spirit in small towns and cities. I understand why this process is seen as a ticket out. When I visit different places and meet startup founders, I try to be nicer and more helpful rather than dismissive. I’ve finally taken to heart the old adage, “Let us be kind to one another, for most of us are fighting a hard battle.”

I’m lucky that I’ve surrounded myself with smart people. Our latest startup, Jaywalk, brought me back together with my longtime college friend Rich, the guy with whom I worked on my first startup. We also have a solid team at an accelerator we joined in Boulder, Boomtown, and we’re slowly building out our dev and UX team in order to create an app that truly rewards you for walking around and discovering new things in your neighborhood. It’s something that’s very dear to me for a few reasons, namely because it’s almost impossible to get my kids to leave the house for a walk if I tell them we’re going to the park but far easier if I tell them we’ll get a cookie on the way back. We want to get people off their pocket computers and back into the world.

I gave a talk about a year ago about how I felt after my first startup failed. It was called “This is fine.” I based it on that comic of the dog in the fiery coffee house. I focused on this quote:

“Set your life on fire. Seek those who fan your flames.”
― Rumi

This quote really bothered me. It was some serious spiritual bullshit. In the doldrums of failure, I saw it as a warning: Set your life on fire and watch what happens, sucker. That’s what I did. I quit a great full-time job, put my family at risk, broke bonds I had with people I loved. And Rumi is here telling me to light the pyre higher. You’ll know your enemies by how they fan your flames is what I thought he was saying.

I was wrong.

I realized that this quote meant something entirely different. It meant that you had to find the right people to help you grow, to help you expand, to help you get the most out of your adventure. You had to find people to fan your flames. Those people helped you burn brighter, not burn up faster.

I found those people in my family, in my friends, in my online community. I found those people in the folks at the accelerator who placed early bets on us and in the folks I built stuff with.

I’ve spent the past two decades in my attic, writing. For me, building was always a solitary endeavor. Those friends helped me finally get out of my proverbial attic and I started building with others. And it’s that effort, the effort of creating in concert, that truly defines us as a species. My friends didn’t fan my flames to burn me out. They fanned them to help me light up the dark.

This is a long way of saying I’m building something new. I’ll keep you posted, and let me know if you need anything.