The Upside of Betting on Long Shots
Why rooting for the underdog and being an early adopter are the same instinct.
I’ve spent the last few weeks watching World Cup matches and highlights at ungodly hours while traveling the globe, and I noticed something about myself: I usually want the less popular team to win. Not because I have any allegiance to Cape Verde or Ivory Coast. I have no personal ties to them or most of the teams. I just can’t help rooting against the favorite.
Cape Verde is a country of about 525,000 people. They’d never been to a World Cup before this one. In their group opener, they bravely held Spain, a gold standard team, to a scoreless draw. Ivory Coast, also making their first trip to the knockout rounds, scored one of the best individual goals of the tournament and pushed Norway (with Erling Haaland, arguably the best striker alive right now) to the 86th minute before losing. And Paraguay, who got run over by the US in group play, beat four-time champion Germany on penalties. First shootout loss in German World Cup history. They also fouled like it was rugby for most of that match, so I only briefly rooted for them — and reluctantly.
None of these teams had anything close to a winning track record against these opponents. That’s exactly why I couldn’t look away.
I don’t think this is really about the teams, though. It’s about what picking them says about me.
⚡️ It’s driven by my sense of identity and emotional rewards.
Everyone else can have Spain, France, or Argentina. The second I’m rooting for the team nobody expected to matter past week one, I get to feel special. It’s a cheap, harmless way of confirming I’m not the guy who only shows up once something is obviously correct. And the emotional payoff is just better. Everyone assumes the favorite wins, so when they do, it’s a small buzz. When the longshot pulls it off, and even more so in the anticipatory build-up, the dopamine released is bonkers, and some part of my brain is running that calculation every single match.
Turns out this isn’t just a soccer thing for me. It’s related to why I’ve spent most of my adult life betting on things before anyone else thought they were worth betting on, and it’s paid off in ways that have nothing to do with money.
Books, before they need you
When my own book came out, each preorder meant more to me than orders after launch. People emailed just to say they’d grabbed a copy, and I responded to every single one of them. That attention window closes fast. Once a book, or an app, or a movie, is generating wider attention, the person behind it stops being reachable the same way.
I’ve felt this from the other side too. I bought preorders of a handful of other authors’ books, and more than once the author personally emailed me back within a day. That’s the trade: show up before the crowd, get a level of access the crowd never will.
A friend of mine produced an indie film that made it to theaters in the US and a few other countries. I followed the whole thing from development through its premiere in Taipei, and ended up being one of the first 100 people to review it. That was pretty damn cool: seeing some of the process along the way and going to the premiere. I have zero connections in Hollywood. That kind of access doesn’t happen often, unless you show up before there’s a reason for everyone else to.
The plane that was still being built
I got a rawer version of this lesson from being in the first cohort at both Boost VC and MOX, two startup accelerators that, at the time, had nothing to point to. No track record. No portfolio of wins. Their only credibility was that the people running them had some connection to some organization with a track record, but it wasn’t their own. They were building the plane while we were already in the air.
That comes with real downsides. There’s no fund-raising advantage to leading with “backed by a first-batch program you’ve never heard of.” You’re the guinea pig for whatever process hasn’t been ironed out yet. Resources get promised and then quietly scaled back once the org figures out what it can actually deliver.
But their was a hidden upside that I discovered, too. There was no playbook, which meant I had actual input into how the program ran, not a scripted experience built for cohort number fifty. I got real face time with the founders, not a rotating cast of program managers. The bar for getting in was lower and less rigid (hey, maybe that’s even why I got in), because they hadn’t built the demand or machinery yet to filter people out on paper. It was a more even playing field between a startup with no money and an accelerator with no track record, which is rare.
Thanks for the free lunch
I see the same pattern with early tech adoption. I was one of the first users of the food delivery apps that launched in SF over a decade ago, back when the teams running them were tiny and still figuring out unit economics. I got a ridiculous amount of free or heavily discounted meals, subsidized by VC money, some of it from firms that had rejected funding my own startup. So, fine, I’ll take the free lunch.
Compare that to using one of those apps today, like DoorDash or UberEats. You need to take out a damn mortgage to order a sandwich. These companies went public, and now squeeze margins out of restaurants, drivers, and customers all at once, because that’s what happens once growth has to answer to a stock price instead of early growth mode.
I think about this constantly with DOWN, the dating app I cofounded. Match Group owns Tinder, Hinge, OkCupid, and something like a hundred other dating apps at this point. Their business model, and Bumble’s too, still seemingly employs tricks like queuing up the most attractive profile right after you burn through your free likes for the day. We shaped DOWN around the opposite bet: grow revenue as a byproduct of people actually having good experiences and better matches, not despite it. It’s slower. It’s also the only version of this business I want to be running.
The quiet caveat
Said plainly: the absence of social proof isn’t evidence of absence of value. The best-known book, app, or restaurant may just mean that most people happen to know about it already. That’s a signal, not a guarantee. Sometimes the quiet thing is quiet because it’s new, not because it’s bad.
But that’s not the only reason I root for the new product or underdog. Supporting something before it’s proven feels good in a way that supporting the juggernaut never does. Watching Cape Verde hold Spain scoreless, getting an email back from an impressive person because I jumped on their project early, getting real opportunities to shape a startup accelerator because they didn’t have a system yet to keep me at arm’s length: that’s the actual payoff, and it’s more fun than being right about the safe pick.
⚡️ So try the smaller app before you default to the one everyone already uses. If someone you know launches something that isn’t yet the thing “everyone” has heard of, be one of the first ones in.
It will mean more to them than it ever will to a conglomerate that doesn’t notice you, and you’ll probably get more out of it than you expect.
Shameless plug, since we’re on the topic: my book hit the USA Today bestseller list and picked up endorsements I’m genuinely proud of, but it’s far from the de facto startup book on everyone’s shelf. Yet.
Grab it now to be earlier than most, and you get a level of access to the person who wrote it that’s hard to get later.