I had the idea for 20Skaters for a good five years before acting on it. While I’d never run a weekly pickup hockey game, I subbed and played in them a lot. I noticed the attendance at these games being all over the map. Some weeks 9, some weeks 23. I’d rented ice myself so I knew the costs to rent icetime. Everytime I played, I would do the math in my head and the numbers clearly meant the person running it was losing cash.

I also witnessed the weekly frustrations of the players in the room when you only had 9 skaters and 1 goalie, or worse 23 skaters and 3 goalies.

It was clear that you had a lone person spending a ton of their personal cash to organize a weekly game for friends. They were losing money, while having those same friends bitch and moan about attendance.

I remember one specific case where a friend decided to run two pickup games. I didn’t attend but I asked him a few weeks later how it went. Sarcastically he said, “great, I had 20 skaters committed for both skates. We had 9 skaters show up at one, 14 at the other, I lost $245 on them and I’m never doing that again.”

I sat on the idea for 20Skaters for years because I didn’t think it was the right time for hockey players to pay for pickup hockey online, ahead of time. It was too soon, not enough people had purchased items online yet.

Eventually it started to feel closer, the majority of people I knew were starting to make online purchases and use more online services. To prove the market was ready, I ran some tests. I purchased a few icetimes from the city. I built a very basic webpage that showed the game details along with the players who were committed to playing. I added a Paypal ‘buy now’ button to allow players to buy spots online for the game, directly from the game page.

Next, I emailed the link for the webpage around to some friends to invite them. The webpage was a static webpage. To make it ‘dynamic’, when I received an email from Paypal telling me that I had a sale, I would change the webpage on my laptop to include the person’s name into the ‘players attending’ list. I’d then ftp that new webpage up to the website. Boom, a dynamic gamepage.

I had the occasional keener who would email me right after purchasing to say “hey, I just paid for hockey but I don’t see my name on the site, maybe I did something wrong?” I would change the webpage, ftp it up, then email them saying “Sorry about that, issues on my side, have a look now, should be good”.

While the manual work to make the site appear dynamic was a pain, that was a solvable problem. The magic proof of those early tests was that I sold those games out and players grabbed spots without talking to me. They shared and invited players I didn’t know well. I had all my money collected before heading to the rink. I’d proven to myself that hockey doods would pay for pickup hockey online ahead of time.

I recall one particular evening where I was going to be without internet access for several hours the day before a game. I still had 5 spots open and was worried I’d be short. When I returned to having internet access, I had 4 purchase emails sitting in my inbox and was down to one spot left. It was that experience that sold me. The fact that my game was working, and filling itself, while I was completely offline, that was the magic!

At the time we started there were a lot of early sites built to help you run your team in a league. There didn’t seem to be anyone building for the unique use case of running a weekly drop-in style hockey game. After the successful experiments, I started to share what we were building publicly more. I got some other good folks involved, who have been pivotal in getting to where we are today, namely my cofounders Bill and Eric. Our early name was NoReferees Hockey, which we eventually changed to 20Skaters Hockey.

The final straw in getting our first working product launched was one of our now long standing organizers. I had pitched him the product in person at an event. Since that time he’d been emailing me asking questions about it. Jamie is a startup founder himself so he understood the journey. He phoned me the week before labour day and gave me a final kick in the arse. He basically pitched my product back to me, told me he’s tried everything, event sites don’t work for him, the team sites are built for leagues but are a pain for pickup hockey, email lists aren’t enough, he wanted our product and didn’t want to start his upcoming season without it. His season started in 3 days.

I spent most of that labour day weekend locked in my office building. I don’t think I pulled any full all nighters but they were long days and late nights. I managed to build enough of a beta to get Jamie’s game launched with us and we’ve been organizing his game ever since.

We’ve now run thousands of games and are heading into a growth season. While that’s the story of how we got to here, we’re hoping this is just the beginning so stay tuned!