Growing a startup is a remarkable saga — here’s some insights two years in🎊

Jobs can be a source of immense joy and creativity, or stress and fear, and sometimes you’re just hanging out in the middle of that

Bacon, Burbon, Bean Bags, and Beginnings

Drawn by the allure of working with OpenSports at “The DMZ”, Toronto’s most praised tech startup incubator with free daily breakfast, an endless supply of coffee and sweets, hammocks in the middle of the large open co-working spaces, private phone pods, exposed beams, and other playground-esque amenities, I was curious about a position with this pickup sports company that my friend Tanya referred me to. All I knew was that OpenSports had not yet launched their app, worked out of a fabulous space, and needed some marketing help.

I met James and Chris, best friends and two of three of the original founders, at a downtown bar over a drink — I ordered the bacon infused burbon cocktail—followed by a tour of the DMZ. After a few drinks and what felt like a living room hang out on the oversized colourful bean bags in the DMZ games room, every part of 25 years old, energetic, playful, and open-minded me wanted this life and wanted this job.

Listening to even 30 seconds of their tech-jargon-infused conversations, I would have never guessed that I would find myself in my role —as the Co-founder and “Marketing Director” of a tech company. WTF? I had never even taken a business or comp sci course in my life. I was scared shitless and had to reassure myself that James and Chris seemed pretty excited about having me come aboard.

Once I grew some competence and confidence in myself and my ability to execute my role, which took several months (my personal rule of thumb is to give myself about two months to feel like I’m good at a job and subsequently start to genuinely enjoy it), the next big challenge for the months and years to come would be growing the app.

I want to commemorate that past two years since we launched OpenSports because although it has been very challenging, I have come to accept that there are so many setbacks before the momentum hits (and it has!), which is always followed by more setbacks! So, Happy Second Birthday OpenSports! Here’s a few of the core things I’ve learned over the past two years, arranged by theme/topic…

Leadership

In his inspirational book “Leaders Eat Last”, Simon Sinek talks about the importance of taking care of your people first and worrying about numbers and metrics last.

I recognized fairly early on that I work with someone that will lead people to build great companies, and his name is James Gibbons. James is a profound leader who buys you beer on a whim, sprints to the pharmacy to buy every type of throat lozenge and sleeping syrup when you’re sick on the road in Atlanta, ensures you take enough time off to get over a pretty intense period of burn out while checking in with frequent humour filled phone calls, sacrifices most weekends for work, celebrates everyone’s birthdays, patiently and compassionately guides you through highs and lows, never fails to ask how your evenings or weekends were, shows great value and appreciation for everything that you do, and goes beyond what I thought was humanly possible on this quest for success.

So, basically, OpenSports has a remarkable leader and if it wasn’t for James’ perseverance, ingenuity, and genuine kindness, OpenSports would be just another idea that died just as quickly as the initial excitement fades.

Growing fast vs Growing slow

Sometimes you can have a much slower growth model and still come out winning. — Adora Cheung

I am actually quite grateful for slower growth. When I go to bed at night, I think, “Thank you universe for not giving us any new groups today🙏!” Just kidding!

Seriously though, you don’t know anything until people start using you app, so you don’t want 10,000 people to start using your app on Day 1. An overhyped launch can be dangerous and in our case deadly because our app would have failed to deliver on its initial brand promise and would have had a lot of bugs, both of which lead to terrible reviews, which is very hard to recover from.

Granted, we are lucky that James has found every way possible to keep our company going while bootstrapped, and that has bought us the time and ability to grow slower and with quality, but honestly, if we had a huge launch out of the gates, we would have been absolutely f*&ked. We have a handful of “main” groups that we are in touch with on a weekly if not daily basis, and responding to their feature requests with a team of three is hard to keep up with. Growing slow has allowed our team to rally around core metrics that will contribute to long-term sustainable growth, so that we can eventually scale and grow.

Doing un-scaleable things

Success is just a series of little wins.

We have always celebrated the little “wins” — one pickup sports game or group at a time. We used to high five when Santiago from Toronto would post a pickup game on the platform, and cheer every time an additional user would join his game. When an organizer would tell us that people didn’t actually turn up to their game, we felt like we got punched in the gut. We ran our own games several mornings per week and learned all about the pains and rewards of being a sports organizer by experiencing it ourselves, and we now use those experiences as a foundation of understanding when we have conversations with experienced organizers. It’s really important to connect with your customers and although sometimes that on the ground grind was exhausting, it was worth it.

Mental Resilience

Don’t confuse temporary setbacks with permanent failure.

I have always been a pretty loyal employee/teammate/friend. When I like something, I stick with it for as long as I feel valued and I feel like I’m contributing in positive ways. But the ups and downs you go through with a startup can really test your mental fortitude (these can be associated with running out of funding, not growing your user base, having to fire people, managing upset customers, and generally feeling like you’re failing).

Whenever I’m going through a difficult time with OpenSports, whether it lasts 3 days or 3 weeks, I remind myself that nothing comes easy, and it is the journey that is important, not the end result. This mindset takes some time and experience to cultivate and eventually builds mental resilience which helps us all get through periods that feel like lulls (in growth, excitement, etc). When you stick out those periods enough times, you know they will eventually pass, and that in the end, it will be worth it to have gone through that challenge, but sometimes you really do just wonder if it’s time to give up (For us, it’s NOT! it’s SOOOOO not!).

Our Team

The importance of your TEAM. If James, myself, and Yi An did not value the s**t out of each other, we would not still be working together. We have laughed so, sooooo much together. And we have cried together. And then we have laughed together some more.

“Leaning” out our team

Ah, I really, really miss people that I used to work with here. Regardless of the reason that we could no longer work together, I value everything that everybody contributed, and I really, really miss you all. James and I used to be the worst at letting people go because we’re both really nice people, almost to a fault in this regard. Prolonging this process is absolutely torturous and painful for all parties involved. In any case, I feel forever grateful for everybody’s contribution.

Culture

“Finding your cofounder is setting the culture.” — Adora Cheung

We never wrote out our core values, but its pretty clear that who we are as a company reflects the core values that our founders hold as individuals. So I would say they are:

Empathy, Camaraderie, Trust, Loyalty, Food, Fun

I do believe that sharing food has really added to our dynamic as a team. James sometimes wakes up early to get our favourite almond and chocolate croissants before they sell out from the local bakery, Yi An comes back from lunch with cheese tarts from Uncle Tetsu’s bakery, I come in with a fresh pumpkin pie made by my mom and James goes to buy liquid whipping cream and a hand whipper. The food related experiences of generosity and sharing reminds me of my roots and makes us feel like family, and it adds elements of togetherness. #EatTogether

Our Customers ❤

We love our users. We cultivate relationships with them, and even went on a 3 week USA “road trip” this past spring to meet them, which was a truly amazing experience (I highly recommend doing something like this!) We refer to our customers by name in our workplace…they are as real as it gets, and we have different relationships with each of them.

Special thank you’s to Dan from Philadelphia Volleyball, Puchee from Toronto Soccer Connection, Court and Wedge from SOPFC, and Dan and Sam from Chicago Fire Recreational Soccer. Your support has validated our concept and given us the strength and hope that we have needed to push through times that have been difficult. You have all given us so much feedback, been patient with our lags in development time, been supportive, and ultimately pushed us to develop a better product.

Desperation Projects

When I look back at some of the promotional ideas we have had, I am like, “Why? Whyyyyyy?” or to put it more positively: “Ahhh, now I see why this didn’t work!”

• One time, within the first few months of launching, we gave out OpenSports post cards in front of the Air Canada Centre because “sporty people OBVIOUSLY go to watch Leafs games”. Literally everybody walked by us. Maybe we’re just positioning ourselves in the wrong place…Let’s split up and stand on different street corners to maximize our reach... Maybe we came too close to the start time of the game and everybody is just in a rush to get in. No, No, Nooo! This just isn’t our target customer!!!
• Our “OpenSports Bot” was applying for jobs, under the alias of Sheldon. I cant even remember why, but it was hilarious.

• “Watch me YC” — if you haven’t read about our hilarious 24 hour “hack” where we built a hilarious site to try to get into Y Combinator, read here!

Focus

The more you know what you are, the easier it is to make choices and prioritize during the day.

We used to experiment with everything, all the time. One week we thought that the Coaches Association of Ontario was feeling our product so we’re like “Let’s have coach specific features and connect coaches with players!!!”, the next month we thought we had a chance with the Pickleball Association of Ontario and we’re like “Let’s focus our APP launch on a sport that is predominately played by RETIRED people!” 🤦🏻‍

It’s clear that back in those days, we didn’t even know who we were yet. Now, when we are struggling to prioritize the development of features, its not because we don’t know which segment of the sports market to go after, its because our actual customers are requesting features that will make it better. For the first time, our development can’t keep up with the real demand! And that is so bloody empowering! Our customers tell us how much better OpenSports would be with a couple of important additions, so we do something about it. Every single day.

Hustle and Grind

When I had my first real bout of “burnout,” I became a believer that “hustle and grind is not a badge of honour.”

When I see a person that “does so much”, I don’t perceive them as having the natural capacity to do more than everybody else. I see someone who is probably struggling to find balance, who feels perpetually stressed, like there is never enough time, and like this cycle will never let up. I have lived a life of being super busy and receiving constant praise and validation about how cool and great “everything that I was doing” was, while I was actually completely suffering. It’s no fun, and I don’t recommend it!

I think that being a leader and doing cool shit is awesome, and I love being that person, but with success and leadership comes more and more people wanting your time and wanting a piece of you. I think it’s important to find one or maybe two things to really focus all of your energy on, and learning how to say no to everything else. Then you can really devote yourself to it.

What Will Year 3 Be About?

Making OpenSports AMAZING.

Fundamentally, we think the product is close to where it needs to be… we have a few obligations to get done on the development side for our key organizers (and all of the groups yet to come)but then we can zero in on making the platform itself amazing.

Thank you everybody who has supported us — friends, family, players, organizers, and former colleagues!! Let the journey continue!

Thank you for reading

❤ Alicia