I’ve been away the past month and I wish I could say it was due to vacation. Alas, the Euro summer will have to wait, as I’ve been doing 637289129 other things that didn’t allow for the self-indulgence of writing with the expectation that someone might actually read it. Tragic!

Have no fear, dear readers, the thought-haver has emerged from thinklessness and it’s time to put fingers to keyboard once more. 

Fair warning: the next couple pieces will most likely be sports-related and this current piece is 100% sports-related, so if that is a snooze fest for you, I advise you read no further. Welcome to my fall thoughts. 

It’s yet to be decided on whether football signals the start of fall or fall signals the start of football. “Football” in this context being American football and “fall” being the first Thursday in September. 

Regardless, the false fall that is the first week in September is a fun one for me. I grew up in the south and there is little that holds a candle to Friday Night Lights and the start of the season naivete that the Cowboys will be conference champs. The intensity, and arguably obsession, that fans hold for their teams is unmatched. Sundays are for worship and the place of worship is any given living room or local bar that has the game on. 

This year, I did something I have never done before: I joined a fantasy football league. I’ll admit, I never understood the appeal of “fantasy” until about a year ago when I caught myself asking questions about the logistics of being in a league. “How does the waiver wire work?” “Is there a punishment for last place?” “Just how committed does one have to be to operate a fantasy team?”

Turns out a few of my other friends had secretly been thinking of joining a league, and a few of their friends were also curious about how fantasy works, and then three of their friends actually downloaded the app.

Before I knew it, I was in a group chat with eleven other fantasy-curious types, participating in a 9pm draft the day before the 2025 NFL season, officially joining the inaugural season of the “Girls 4 Analytics” fantasy football league. 

As we were going through our draft, some auto drafting while others quickly texted screenshots to their more football-inclined partners, my mind drifted and began connecting fantasy football to startups.

Venture has a weird way of creeping into every single detail of your life, whether intentional or not. On this intrusive occasion, I found myself thinking about it for an absurd amount of time. 

It sounds silly, but doesn’t the first step of fantasy football (the draft) kind of feel like investing in pre-seed startups? To state the most obvious, it’s all about the player. You’re coming into a draft having ideally done your research, some may call it “diligence,” on various players.

For the risk lovers, there are new players out there trying to make a name for themselves, but the more risk-averse have the option of going with a proven vet, a player that has a track record of putting up great stats.

Each player brings a unique skill set to the table and there are a finite amount of players to choose from. Not everyone can get a piece of Saquon (Barkley, Eagles stud) and you can’t draft only running backs. You need strength across a variety of player positions to have any chance at accumulating points…diversification, if you will. The similarities do not end at the conclusion of the draft.

Once you have your team *cough* portfolio, then the real game begins. You’re immediately matched up against someone in your league and are inundated with data. You’re given statistics such as the likelihood you win that week’s matchup, the start percentage of the player you chose, and the projected points for your team that week. It’s equally impressive and intimidating.

Most startups have little to no data, but the similarity here is that startups are always competing. Companies are using every bit of information they have to make decisions that will give them an edge over their competition. And so are their investors. The details matter, and even a single percentage point can make all the difference. 

A fantasy team quickly starts to reveal which players are consistent point-producers and which ones may need extra time to find their fit. It’s not instantaneous, but I’m a few weeks in and I can already start to see which players on my team (portfolio) stand out, which might plateau, or be underperformers. Similar to an investor’s partnership with a startup, there is a chance to intervene. You can swap players out and try a different strategy for the week.

This is an art not a science, but there is something to say about a pivot. You can trade players with others in your league which requires advanced negotiation skills and valuing what is a “fair” trade. After all, secondaries can be a very tricky business. It’s a long season and remaining attentive to your team and knowing how to best support your lineup is a crucial part of the fantasy commitment. 

If you aren’t following my train of thought, well, you’re not the first but let me share my last connection to what I believe is very similar to my line of work: Both fantasy football and investing in startups have long feedback loops. The choices you make in September are not fully celebrated or criticized until February. The choices you make to invest in a startup are not fully deemed a success or a failure until year seven or ten. How do you know if your choice at that moment was the right one? That the player you picked is going to be the returner, the one that gives you all the points? Does anyone really know? Not in the beginning, at least.

So why do people keep coming back to fantasy football when their odds to win are slim, there is constant competition, and the season is full of uncertainty? And is the strategy based more on luck or skill? These same questions can be posed to investing in startups, especially startups at the earliest stages.

I think the answer lies in the desire to be a part of something great (dramatic for fantasy football, but stick with me). People draft players they believe in and people back companies at the earliest stages that they see extreme potential in. Each draft, or check wire, is a bet in itself and one worth waiting to watch unfold over the course of six months or seven years. 

Lastly, I would be remiss not to mention the role of luck in both fantasy football and startups. There is skill in choosing the right player or the right company to back, but there is also luck in a player staying healthy all season and a company building at the right time. People will keep playing fantasy and investors will keep investing in startups, and whether the end results reflect luck or skill is still an open question.

I do think about this a lot, probably too much, the balance between luck and skill. It’s too soon to say which of the two will influence the rankings most in the Girls 4 Analytics league, but all I can say is that I got super lucky to land the #1 pick for our draft and I’m also 0-4 for the year.