Betting On Yourself

It turns out that betting on your own ability to be your imagined version of yourself is much harder in practice than in theory.

For as long as I have been in the fantasy football industry, the idea of being in charge of my own “thing” has been appealing. We joked about this quite a bit on the Swolecast and Ship Chasing after Pat Kerrane shipped two million and started Legendary Upside. I mean, that’s the dream!

I’ve largely had very comfortable jobs in fantasy and in sports betting that were also fulfilling to some degree or let me access side projects that were fulfilling, at least. As a lot of you know, my position at SportsGrid got eliminated last month and I was really at a crossroad. At first, I was sort of hoping to land in a similar full-time job with one of the big sites in fantasy football but as I went through the interview process and had very helpful conversations with Peter Overzet, Ben Gretch and JJ Zachariason in particular, I realized that wasn’t the optimal route.

On one hand, I could peace out of the fantasy industry entirely. The corporate world always needs a new professional emailer, the Great American Novel has not been written (though Infinite Jest comes close) or I could all the way back to my roots and go back to school to get a Creative Writing MFA. That definitely would be the simple path. Very little resistance, it would have come with a degree of financial security (and healthcare!) and wouldn’t have been questioned by the world at large.

On the other hand, that feels like a bit of a waste given the particular way I’ve spent my professional time. My entire adult life has revolved around speculating on sports and on top of that, I’m pretty good at it! Writing articles, podcasting, live streams, speaking off the cuff about sports is what all of my professional skills relate to. It would be a huge waste to toss all of that in the bin and start over from scratch, at least from my perspective. It’s true that it is never too late to reinvent yourself if you aren’t happy or aren’t maximizing yourself but that isn’t how I feel. In fact, I feel that I was not coming close to being maximized in my old role.

Which leads me to the bet. The bet that I am now making is absolutely terrifying to be frank. As a fantasy football “soloprenuer”, what you are effectively doing is betting that there are enough people who just like you enough to financially support you. Sure, I absolutely will help you win money playing fantasy football, of that I have no doubt but that is also true of several other fantasy football destinations that already exist.

And guess what? There is absolutely no guarantee that enough people are going to subscribe to the Davis Mattek YouTube channel or sign up for the premium fantasy football Patreon to sustain myself. All of this is taking place in front of 65,000 twitter followers and all of my decade-old peers in the industry and all of my friends and family who think that I have a “cool job”. What if that “cool job” turns into absolutely flaming the fuck out because no one cares? Pretty scary! The binary success/failure outcomes don’t feel that comfortable but taking risk is just part of the game.

That fear nagging at the back of the brain is not all that helpful in this spot. Not everyone needs to win $2,000,000 thanks to Austin Ekeler to start their own fantasy football website. In fact, if that was the case in the larger world, we would be living on a far worse planet. Bootstrapped creators have made some of my favorite art in the world precisely because it was their passion that was more important than the money. Don’t get me wrong, I absolutely create content for money and if there was no money in it, it would be time to learn corporate, buddy. However, there is definitely something to be said for the fact that I genuinely do love writing and talking about fantasy football.

That is a long way of saying: getting let go from a stale but comfortable job was probably for the best for me. It is possible that I fall flat on my face and have to start from scratch (again) which would be pretty god damn embarrassing! However, given that the return is that I feel more energized about the work that I’m doing, loving doing the marathon streams with all of you guys and I’ve never been more pumped for an upcoming NFL season, I am comfortable with the risk/reward calculus of failing.

So, I hope you all continue to enjoy these weekly (back on track now) newsletters, consider signing up for the Davis Mattek Patreon, or hanging out with me on the almost-daily Youtube Streams.