Five Lessons I Learned Bootstrapping a Fantasy Sports Company

I was a bootstrapped founder before it was cool.

Back in 2013, when it was all about building a startup and jumping through the funding loops, I bootstrapped a fantasy sports company.

It was profitable from the first month.

I ran it for a few years before finally selling to a larger competitor. Along the way, I learned a ton of important lessons. Here are the main ones. If you’re thinking of bootstrapping a company, these insights can easily be the difference between success and failure.

Customer service allows the little guy to compete

Nobody likes dealing with customer service. Chatbots, automated email responses that ask you to write another email, customer service reps that refuse to think about what you’re saying to them, language barriers, impossible-to-navigate FAQ sections — we’ve all been there, and it’s a huge pain.

Particularly when dealing with big companies, talking to customer service is something most people dread (myself included). That’s why I made it a point to be different in my own business from day one.

I treated my users like long-lost friends who are getting in touch, not like customers. I had email notifications on my phone and I regularly interrupted other work to respond to users. Most founders will advise against this, but then again, most founders will never run a profitable business in their life. The popular mantra that you should delegate and automate everything you can instead of getting down and dirty yourself is the reason many businesses never get off the ground.

I did the opposite for as long as I could.

A user’s fantasy team has an error? Check the error, fix it, respond in five minutes.

A user wants a payment refund? Refund it (no questions asked), respond in five minutes.

A user has a feature idea? Respond immediately thanking them, discuss the idea with them, place it on the maybe pile and make a reminder to let the user know what you’ve decided down the line.

I cannot overstate the delight this generates among users, not to mention the accompanying trust and loyalty. If word-of-mouth growth is what you’re after (and you probably should be) this is the golden rule.

Avoid having a 3rd-party point of failure

I learned this the hard way — not once, but twice.

The first time, I was scraping statistics from a football website. When they made massive changes, I was suddenly forced to enter match statistics live, as they happened, throughout the weekend. Let me tell you, this is not a pleasant task.

The second time, I received an email from Stripe saying they can no longer support my type of business and that appealing the decision was pointless. Boom — subscriptions are no longer working. I had PayPal but it was only used for one-off payments.

The lesson here is to avoid having a single point of failure that you don’t control. Having a backup payment processor might seem like redundant work, but it can be a life-saver. Likewise, if your app is heavily data-driven, relying on a single data source can throw you into a tailspin.

I understand that these issues are often unavoidable, but you should prevent them whenever you can.

I failed to leverage the community

While I was eager to join the existing communities of fantasy sports fans (mainly through popular forums and blogs at the time) I completely failed to harness the power of my own user community.

I had a Facebook page but only posted sporadically and didn’t drive engagement. I didn’t see the point of Twitter at all. I didn’t have a blog on the game website. In retrospect, I missed out on an opportunity to build organic traffic for the games and increase user retention through community-building.

It is hard to estimate how much I lost through this failure, but based on my latter experiences my rough estimate is a lot. Cherish your community.

It usually makes sense to hire freelancers

As a bootstrapped founder, you may not want to take on a cofounder for every little thing you don’t know how to do. You can’t afford to pay someone a full-time salary, and your own time is limited.

The solution? Freelancers.

I hired freelancers for everything from market research to the design of player icons. It’s a very low-overhead way to get tasks (particularly one-off tasks) done efficiently.

Know when it’s time to quit

In 2017, I sold the games to a larger competitor.

Due to developments in the US, fantasy sports as an industry was about to become a lot more dangerous to navigate from a legal perspective.

I estimated that the potential costs of legal battles far outweighed the gains. It turned out I was right, since the buyer of the games struggled to stay afloat later on even with their lawyers and funding.

Tenacity is a good trait, but stubbornness isn’t. Know when to bow out. Despite what motivational speakers might tell you, some battles are best avoided.


The entire experience of building and running a company in an industry as exciting and dynamic as fantasy sports was exhilarating. The lessons I learned have proved themselves valuable repeatedly in my business and the businesses of my clients.

Building a startup with the help of VC funding has its own set of lessons for sure — but if you want to test yourself in a variety of challenges, there’s nothing like building a company from scratch with your own two hands.

Don't miss the next blog post!

I publish a new blog post every Wednesday. Join the newsletter to get:

  • One valuable email a week.
  • Zero spam.
  • Exclusive content not found in the blog.
  • Reply directly to me with questions or feedback.

Use the form at the bottom of this pageon the right to join the newsletter.

Read more: