The way-too-long journey of my small (but growing) startup
My team and I recently got accepted into the Launch Accelerator — an exciting, fairly new, accelerator in Silicon Valley led by Jason Calacanis. In a word, it’s been incredible. But not for the reasons I expected.
In the coming weeks and months I will be sharing my learnings from the program. My hope is that this exercise (1) helps me clarify my own thoughts and learnings around how to grow a company, and (2) helps others who are just starting out get a better picture of what the accelerator and building a startup is like.
Before I get into my learnings though, I want to give you some quick background on me and my journey to this point. Running a startup is really hard and not for everyone, but I find a lot of comfort knowing there are others out there just like me going through the same stuff. Hopefully you will too.
I was raised in a small town in Oregon. In my adolescent world, you grew up and either (1) worked a blue-collar job at a small business, or (2) owned a small business. Big office buildings with 1000s of employees running around were things I only saw in movies, and I hadn’t the faintest inkling of what went on inside those buildings.
When I went to college, my eyes started to open. I remember sitting in economics class one day listening to a lecture on demand and scarcity. In the lecture, the professor was auctioning off one Little Caesars pizza to 800+ students. The class was right before lunch, and the thought of a hot pepperoni pizza was widely appealing.
Despite our collective hunger, any college kid on a budget knew that the pizza was worth $5. Surely no one would be willing to pay more than market value for the pizza — right?
The bidding started. “3 dollars!” one student yelled, “4 dollars” said the next. The 5 dollar bid came next. “Auction’s over,” I whispered to my classmate, disappointed I hadn’t shouted my bid fast enough. The room paused. Then a lone voice from the back shouted “6 dollars!” and 800 confused economics students eyed the guy, perplexed at his obvious irrationality.
Then, suddenly, another voice bid 7. Then 8. Then 9. Within a few bids the pizza was going for $17, then $23, then $28. With each new bid my disbelief grew larger. The bidding landed at $35, seven times the market value.
I was astonished. What kind of insane hunger could have possessed a person to so severely overpay for a mediocre pizza?
It was in that moment that I realized what businesses do — they solve a problem for a person that was willing to pay for the solution. And if the problem was big enough and shared by enough people, the potential for that business was enormous.
With this sudden realization, my world was colored in a completely different light. I started seeing problems that needed to be solved. Hundreds of problems. How to reduce the cost of textbooks, how to make the school cafeteria more efficient, how to improve the quality of time in the classroom, how to find girls to date.
I couldn’t stop finding and thinking about problems — they were opportunities. Some potentially big opportunities. I became fascinated with the field of business, and I decided that I wanted to become an entrepreneur.
The next 6 years I spent exploring the world of business. I attempted multiple startups — my first was a gutter-cleaning business that was growing well, but I shut it down after falling off a 2-story roof, twice. My second was a ride-sharing platform called Skedaddle (Uber wasn’t around yet) that never really got past the design phase. My third was Groopies, an app that stored all your punch cards and helped small businesses with their loyalty programs that never quite made it to market.
Then I started Freeplay — an app that makes it easy to go exercise with your friends by giving you a universal gym membership to places in your area, and helping you bring others with the tap of a button.
We built the product with zero money, funded by my product management job at Domo. I spent every night and weekend I had calling partner prospects, designing our product, building the website, figuring out how to start a business. It was exhausting, but the day of our product launch finally came. We were ready.
I remember the first day our product hit the App Store; I was bracing for incredible adoption. “Will our servers hold up with all the people?” I remember asking our CTO. In my naïve mind, that’s how products worked. You built them, and then people bought them.
Aside from a few kind app reviews from my friends on Facebook that never actually used the product, it was crickets for the first 6 weeks. We had one person sign up for the trial and then cancel before the period ended. I remember feeling beat up. I had poured all this time and effort into my company and no one was even paying attention.
I went to lunch one day with Steve, the CEO of a company I had worked at previously and now a good friend. He could tell I was discouraged, despite my obligatory rosy response whenever someone asked how the startup was going. He had started his own companies before, so he knew how it worked.
We reminisced, swapped stories and at the end of lunch he shared his parting advice, “Aaron, the startup world you’ve entered is a wild one. Some days you’ll be at the very top one minute and rock bottom the next. It’s a roller coaster, but you’ll figure it out. Just keep going.” We paid for the meal and headed back to our respective jobs — his in a nice corner office at a large company and mine in my unfinished basement.
Just keep going — the words stuck in my head. They empowered me. I was going to figure it out. This is what entrepreneurs did; they get knocked down, then get back up, and try something else. Fall down, get up, repeat.
I continued to work tirelessly with my incredible team for another year and a half. Little by little we were growing the company — learning from our customers, adding to the product, iterating and improving. Those were long days, and the thought of quitting crossed all of our minds many times. But we persisted.
Things started to accelerate in August 2018 when we stumbled on a new group pricing model. Suddenly people started talking about us. We were getting text messages and emails from our friends saying they overheard someone talking about Freeplay. Many of our friends signed up (no bribes or peer pressure necessary 🤪). We started to grow rapidly, 7x’ing our subscriber base in just 4 months.
During this period of growth, we had gotten accepted into Launch. We were extremely excited at the prospect of learning from some of Silicon Valley’s best and brightest. I was a big fan of Jason Calacanis’ podcast and saw his ability to connect with founders in ways few VCs and angels could. He understood how it works and knew what founders go through.
We started the Accelerator at the end of January 2019. I was a mix of emotions: excited, eager, nervous. We were meeting with 7–8 investors every week as part of the program, pitching them on our business and doing rapid-fire Q&A sessions. I had learned early on that as an entrepreneur you had to be comfortable putting yourself out there, but this was a whole new level.
Now the program is officially underway. I’ve loved almost every minute of it — it’s an incredible opportunity to learn and grow as a founder alongside others at the same stage as you.
It’s been no small amount of work to get to this point, and we’re still at the beginning of this long adventure. But I would be remiss if I didn’t recognize the importance of the advice I got nearly a year and a half ago from Steve: just keep going.
Stay tuned for my upcoming posts about learnings at the Accelerator. They will be plentiful.
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The way-too-long journey of my small (but growing) startup
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