Why I Left a Top Position at a Rapidly Growing Startup
Doing anything part time is hard. This is probably my biggest, PhoneGap-inspired revelation. There is nothing like trying to piece together a native app, embedded in a web view, to remind you how hard it is to ship even simple software. So I put in my one month notice.
I’m recently 24, a self-taught developer with a business background, and I don’t have any side projects with traction. Startup lore is filled with stories of founders giving up nights and weekends building, before going full-time when the company starts to take off. Knowing that I’m far from the only twenty-something enamored with the startup world, I hope my process for deciding to go a different route will be useful to others in similar situations. But first some background.
I spent the last year and a half at a rocket ship of a Cincinnati startup (Roadtrippers), joining as the 13th member of a team on the heels of a Series A raise, and growing with it into the 40 person machine it is today. I went from being a novice web developer (official, on-my-business-card title: Development Squire) to being the sole person responsible for SEO, embedded growth mechanics, and briefly analytics, from early concepting through overseeing and participating in the implementation, as the Growth Team Lead (given the team was 2 people deep at its peak, ‘Lead’ might be a bit generous).
As much as I learned, working at a great company, in an autonomous, challenging role was never the goal, but rather a seductive intermediary that makes losing sight of the goal easy. Working with a bunch of kick ass people around my age, in a top position only a year removed from college, is both prestigious and just plain fun, and exactly the kind of job that makes it easy to spend 60+ weekly hours in the office, forgetting why I joined the startup world in the first place: to build a company from the ground up. Staying at Roadtrippers — no matter how great a place it is to work — would be a form of laziness.
The best argument I’ve heard for staying, is to do so for the learning experience. And that is a good argument; I originally joined Roadtrippers (and Venture For America) primarily for that reason. There is value in learning through apprenticeship, no matter how popular the Nike ‘Just Do It’ School of Entrepreneurship is. The personal growth I’ve achieved as a direct result of working in a well-run startup cannot be overstated, but at some point the returns on additional preparation pale in comparison to those that come from taking a shot, pulling in those who are strong where I am weak, and learning on the go. On top of that, not all lessons are equal, and working in a departmentalized company of 40 may not be the most effective way to learn how to start a two-person company.
There are, of course, other good reasons to stay (financial, social), and accepting that there is value in staying, the obvious path is to build a business on the side. At least that seems to be the conventional wisdom in the startup world. So I tried. I’ve spent the past several months living on a schedule intended to optimize for this type of work: I’m up and working by 6am to get a couple of my highest productivity hours of the day in, before heading into the office; weekend days are spent in coffee shops, and 50% of Friday/Saturday nights at home. (I think my 9th grade English teacher just puked somewhere.) But progress is slow, and I’m lucky if I get the equivalent of two full-time days a week in on side work. The stories of people working full-time+ jobs and then spending 40 hours a week on a budding business are, based on my experience, either greatly exaggerated, a symptom of not actually measuring time spent working, or based on an extremely loose definition of what counts as work. Plus — and maybe this is a sign of personal weakness — shutting off the outside world to this extent doesn’t seem sustainable. It can sure as shit suck, anyway.
Doing anything part time is hard. I am betting that going full-time before having any traction will engender faster progress, greater personal growth, and cost less — in time and emotional well-being — than delegating the work I care about most to the cracks in the calendar. If you are curious about how this experiment goes, follow me in this space. I’ll have an (hopefully big) update at the end of January. Until then, may your specs stay green and your projects top ProductHunt.
