Flirtations with Entrepreneurship

Every since I started my professional career in technology - approximately 5 years ago - I’ve been consumed with the startup world. Angels, VC’s, pre-money, notes, runrates, ARPU, LTV. But I feel as though I’ve only ever flirted with entrepreneurship. And I’m not sure if that’s a good or bad thing. What follows are my thoughts about my experience in the technology sector.

Five years ago I decided I wanted to play in the startup space. I was fresh out of college, had no programming or business experience but I loved technology and solving problems with engineering. I landed an internship at a local development shop called StepChange Group that was trying to ride the Facebook wave by building web applications inside their new app ecosystem. It was a wonderful crash course in development, changing specs, and terrible API’s. And I made some of my best friends there. Greg Rau (founder) and Michael Jones (CTO) were great mentors. We had regular conversations about my growth as en employee, business strategy, client relations, development strategy, and finance. While I cemented my interest in growing companies, I was only ever an employee. I was always yearning to be part of larger conversations. The company was eventually acquired, people moved on, and I left in 2011 to scratch a startup itch.

That itch was a restaurant menu manager idea my fiance (@devonstclair) and I had while searching for a place to eat. We founded Menuish and sought help from the founders of the StepChange Group who had just started an incubator called Upstart Labs. We were naive, super excited, and the spreadsheets made it seem as though success was just a few hundred customers away. We built a prototype but the feedback from restaurants was disappointing - they wanted little to do with our product. Margins at restaurants are razor thin and what little money is invested back in the business is rarely put into tech/web. We pivoted to build a menu search app, which we eventually completed. But the initial blow to momentum caused the project to drag on for months.

For the first month while working on Menuish I was still employed full time. I worked from 8 to 5pm, walked across the street to the Upstart office and did another 4 hours of work, then another 4-6 hours at home. Devon was working full time at Puppet Labs and designing/coding Menuish at night. The hectic schedules prevented everyone from attending meetings simultaneously, which meant key decisions were made without input from all parties. On top of that, I was doing a piss-poor job of actually listening to Devon, choosing to defer to our mentors at Upstart. Lacking time, and having lost patience with me, Devon backed away from the project while I tried to finish it. After working on it off/on while I contracted for Upstart Labs, we finally launched the app in December 2012 and several thousand people downloaded the app. We toyed with monetization strategies but by this point I was burnt out on the project. Even though they might not have felt this way, I felt as though I disappointed everyone around me.

To this day I’m still relatively ashamed how Menuish played out, but wallowing solves nothing and reality has forced me to find a positive side to the story. I learned about early stage funding in the form of convertible notes, how to get customer feedback, search platforms, negotiating with data partners, product management, marketing, and PR. I also learned a great deal about myself. I’m optimistic to a fault, I dismiss opinions when I disagree and I defer to authority too easily. Being aware of those faults, I actively try to combat them and I believe I’m a better person today for having built Menuish.

I was eventually hired at Upstart to help incubate their startups. Towards the end of 2012 I crossed paths with the broker selling my parents’ boat and decided to build a boat classified network in my spare time. I did some light research and decided I could build something better. Without knowing anything about double sided markets, I built a light beta version and started trying to signup users.

For the first 9 months I was convinced I could sign up brokers by simply making the signup frictionless, forgetting that brokers were not Googling for “alternatives to yachtworld”. Having never done sales of any kind, I found myself unprepared and scared to pick up the phone and chat with brokers. It took me months to finally do so but last week I started making calls.

DockLister has been another great self-discovery project. Being the only employee at DockLister means I do everything. I write the code. I follow folks on Twitter. I craft the cold-emails. I wire up Mixpanel. And it has definitely tested my patience. Some weeks I’m wired and want nothing more than to hop on the phone to call brokers, or code up a new feature. Other weeks I struggled to work on it at all. Frustrated by inactivity I distract myself with a short side-project. The biggest take-away so far has been I haven’t done enough sales. A full time job prevents me from spending all day making sales calls during normal operating hours. But I am drumming up support and getting feedback from brokers. My goal for this year is to signup 10 users.

I’ve only been in this industry for 5 years. I’ve worked for 3 startups, StepChange Group, Upstart Labs, and most recently, Recurly. I’ve witnessed two acquisitions. I’ve built several side-projects including I’ve founded two startups, one that failed and one that has yet to do anything. And it’s important to keep that time frame in perspective. No one built a company overnight and only the idolized, statistically insignificant few knock it out of the park on their first step up to the plate. In the mean time I’ll keep on plugging away and soaking up experience here in San Francisco.

To friends and family who tolerate my never-ending list of ideas, I can’t thank you enough for putting up with me.