The Hidden Depths of Bootstrapped Startups

Many people bootstrap companies for a long time. Bootstrapping Oh Hey World (and now Horizon) has been a two plus year voyage. Without a doubt, there have been more downs than ups in my particular journey.

While in Asia hanging out with friends in February 2012, I realized I wanted to start my own startup connecting like minded people in person. Fortunately, Zillow stock enabled me to focus on the startup rather than finding consulting work to pay bills. I spent February until August 2012 looking for the right technical co-founder — and finally found Eric Roland.

We brought on Will Moyer to re-design the app (we used a different designer for the early iterations), and spent from September until April building the location sharing app. We released it into private beta in March. We did solve the pain point of updating a travel bloggers location on their blog with our WordPress plugin. Ultimately, we learned location sharing isn’t a pain point for the majority of travelers.

In April of 2013, our cash runway from Zillow stock came to an end and we were all forced to start contract work. I had spent a lot of my own money building a product that most people didn’t care about.

But we hadn’t solved the missed connections problem.

Fall of 2013, following a 3 month consulting contract with Eric, I was working solo validating new approaches to connecting like minded people in person. Eric ended up working on that project for a year before the funding was pulled about a month ago. Will was doing various freelance work while living in Thailand.

One thing that probably isn’t known to anyone, but me, is how close Oh Hey World (now Horizon) was to getting canned entirely.

Progress was slow. I spent months exploring building a “Tinder for Things to Do” and a mobile social email newsletter reader. I got sidetracked championing a social entrepreneurship concept in Seattle. There was little money in the bank, no solid concept that addressed a major pain point, and no team members. My mom even asked me what I was doing — and I didn’t have a good answer.

I wouldn’t go so far as to say I was depressed, but it was definitely one of my life lows.

The whole thing certainly would have been abandoned, had it not been for the support of some trusted friends/mentors. Eric Marcoullier and Seann Birkelund deserve particular credit for pushing me through the rut.

Eric believed in me throughout every iteration even if he didn’t buy into every product concept I ran by him. He even offered to help validate the mobile social email newsletter concept (one of the concepts I explored). Some may remember the end of Top Gun, when Tom Skerritt (“Viper”, best fighter pilot in the Navy) says to Tom Cruise, “You’ll get your rear when you get to the ship. If you don’t — give me a call. I’ll fly with you”. That’s essentially the same vote of confidence Eric gave me. Honestly, it’s the little things that matter when it comes to confidence.

Seann has been a friend for a long, long time — and cared enough to take time out of his busy schedule to meet in person every time I visited San Francisco. He asked the hard questions, and forced me to talk through the product and business strategy rather than just think through it by myself.

These types of relationships are what it takes to keep going. That’s why community is important in both business and life. When you’re in a rut, you need support from trusted allies. Without those allies pushing you, you’re likely to give up.

I think back to Steve Jobs’ quote:

People say you have passion for what you’re doing and it’s totally true. And the reason is because it’s so hard, that if you don’t, any rationale person would give up. It’s really hard. And you have to do it over a sustained period of time. If you don’t love it, you’re not having fun doing it, you don’t really love it, you’re going to give up.

Fortunately, I am extremely passionate about solving the missed connections (aka community) problem and have an awesome support network that wouldn’t let me quit. It’s that support network that forced me to keep going long enough to discover and validate the private hospitality exchange concept we are now building (Will and Eric are both back full time).

If you want to succeed building a startup, never stop believing. Grind away day in, day out for as long as it takes — and lean on those you trust when times get rough.

If you want to join us for the next journey, you can sign up for our upcoming Beta HERE.

Update: We’re now out of beta.

Download the iOS app: https://itunes.apple.com/us/app/horizon-travel-stay-people/id960391979?mt=8

Or log in to the web app: http://api.horizonapp.co (host side only currently)