About TossUp

My love affair with tennis started at a young age.

I picked up my first racket when I was 10 years old and used to hit against the wall at a local school until it was too dark to see the ball.

A few years later I started playing junior league and throughout the 90s whenever a Grand Slam was on you would always find me glued to the TV for hours watching the legends I grew up with. At the time, some big names on the men's side were Agassi, Becker, Chang, Courier, Edberg, Lendl and Sampras. And on the women's side: Capriati, Graf, Hingis, Navratilova, Sabatini, Seles and of course the Williams sisters. And obviously....yes, I used my hard-earned cashola as a teenager stuffing souvlaki skewers in a Greek restaurant to buy ALL the 90s tennis outfits - does anyone else miss their OG Reebok Pumps or Nike Air Tech Challenge "Hot Lava"?? 🔥.

At 16 I was a league team captain at a local tennis club (Coquitlam Tennis Club - for those of you fellow Canadians in Metro Vancouver) and was playing on my high school tennis team. A year later I got my first taste at becoming a tennis organizer - I created my school's very first tennis tournament which ended up having a 64-player draw 🏆 (this was before email so it was basically me hijacking the PA system in the morning and then walking around hassling people all day to sign up lol).

After high school I went on to get my Computing Science degree and was promptly bitten by the entrepreneurial bug. I started my first business at the ripe old age of 21 doing custom web development with exactly zero knowledge of how business worked. It went OK but it was really just a way of making some money until I could come up with a product idea. A couple years later that opportunity came... I partnered up with a few other guys and we started a software company that invented the technology to sync files between 2 computers over the Internet using only the Windows file manager (yep in 2002, no one was doing that yet, Dropbox showed up about 6 years later 💡). Microsoft eventually bought our patent, which was my first small taste of success with a software product.

OK wait...this page is supposed to be "About TossUp" and somehow it's turning into my personal LinkedIn page 🤦🏻‍🤷🏻‍

Oh well, we already got this far, might as well keep going 😅

So after the file sharing thing, I launched an e-commerce software company called Elastic Path with some other friends. Once we started signing Fortune 500 clients things really took off and I spent the next 6 years helping to build it into a successful 8-figure business. At one point we were ranked #23 fastest growing company in Canada by Profit Magazine. I left in 2008 and the company has since gone on to raise over $144 million in VC funding.

After Elastic Path, I felt a strong pull to combine my experience building web apps and software with my passion for tennis. I eventually got the idea for TossUp League after discovering that most tennis flex leagues were based on the old "box league" model which, ironically, was not very "flexible" (if you signed up 1 day after the registration deadline, you had to wait 3 months until the next season started, etc). We needed something better!

Fast forward to Spring 2015: TossUp League was launched in Vancouver to share my vision of a modern tennis flex league.

I'll be honest: for the first few years, TossUp was mostly my "side hustle" and I didn't have the resources to spend on it. I signed up around 500 players locally and then tried to expand to other cities but was struggling with the time and cost required. I learned a tough lesson that launching something in another city can be quite a different beast than launching it in your own backyard. Anyway, for various reasons, TossUp League didn't get much traction outside Vancouver.

In the summer of 2020 I was finally in a position where I could commit more time to TossUp. At first, it seemed a bit strange to be putting more time and effort into building a tennis business when many cities were dealing with pandemic restrictions and lockdowns. But since tennis was one of the few sports people could still play safely, the timing felt right.

In the fall of 2020 I added a new service called TossUp Clubhouse. The idea was to offer a more social experience that would attract players who were looking for casual hitting, practice sessions, tennis meetups, etc. Basically TossUp League was the place to go for competition and TossUp Clubhouse was where you went to meet and chat and hit with other players.

In 2021 I completed tennis coaching certifications with the 2 main US coaching organizations - USPTA and PTR - and in late 2022, TossUp Training was launched to make it easier for beginners to learn how to play tennis. We pioneered a new method of step-by-step video tennis lessons where, for the first time ever, two beginner players could take entire 1 hour lessons together from their phone or tablet while they were on the court, without needing a local coach.

Of course, some people still prefer to take traditional lessons, and so we've also started rolling out a series of local tennis lesson directories that make it much easier to find those local coaches, lessons and programs. It's still early days but our plan is to eventually reach every metro area in the US and Canada and then expand the directories overseas to become the Yahoo of Tennis (...wait, Yahoo is still a thing, right? 🤔).

At the end of the day, what it really comes down to is that I'm always on the lookout for ways to "serve" you better. (Oh nooo, I thought I'd managed to write this whole page without inflicting you with any terrible tennis puns but alas, the temptation was just too strong 🙈).

Alright, that’s all for now :) Hope you enjoy what we have to offer and feel free to reach out to me anytime!

-- Dave Koo