Vol. 4, Issue 14: Betting Vs. Building
Ring Lardner and the Fallacy of the Gambler's Mentality When Building Teams
The NFL season is upon us — in case you couldn’t tell by the frenzy gripping every sports fan between the ages of 25 and 75, the endless barrage of fantasy football draft results filling your group chats, and the massive spike in ChatGPT traffic asking, “What’s the best way to avoid the punishment my fantasy league hands out for finishing last?”
And when the NFL season comes, the sports wagering season starts in earnest. Don’t get me wrong — we all mess around with silly prop bets throughout the year. “Will Aaron Judge hit a home run tonight?” “Will Anthony Volpe trip over his own feet on the way to shortstop?”* But the real action doesn’t start until the football players take the field, and Sunday mornings are filled with parlays, teasers, and same-game specials designed to make us believe we’ve found an edge that Vegas somehow missed.
*Probably and probably
There’s an old quote: “The race is not always to the swift, nor the battle to the strong.* Generally speaking, that’s not a bad way to live when your money is on the line. It’s the primary reason I bet against the New York Jets** most of the time — even though, as a fan, I desperately want them to win.
*Attributed to Ring Lardner, Jr.
**There’s another quote, “A fool and his money are soon to part.” That’s the other reason I bet against the Jets.
That quote captures a healthy pragmatism. It reminds you not to fall in love with the favorite, not to assume the fastest horse will win just because it should. It’s a reminder to bet with your head, not your heart. And that’s excellent advice: for DraftKings, for FanDuel, for your buddy’s office pool.
But if you’re trying to build something: a business, a team, a community, even a family - that mindset is dangerously incomplete. Because building is not about hedging against risk in the short-term. Building is about creating something resilient enough to withstand the long term.
Let’s stick with the horse race metaphor for a moment. In a race, all that matters is who crosses the finish line first. Everything else is irrelevant. Second place pays less, third place pays almost nothing, and if you’re the horse who finishes last … let’s just say you don’t want to be the horse that finishes last
That works fine when the objective is a singular outcome. You pick the winner, cash the ticket and walk away.* But in a society, a company, or a team, strength doesn’t come from one winner. It comes from the web of contributions that make the whole system function.
*And come home a hero with armloads of gifts for your adoring family, which treat you like a king when you walk through the door in a dream that you had about 1956
That makes the village metaphor is a better fit. A village doesn’t just need one fast runner; it needs all kinds of functions that provide objective value: farmers, teachers, nurses, caregivers, the people who keep the water clean and the power running. These aren’t glamorous roles, and they rarely make the highlight reel, but they are the difference between a functioning community and chaos.*
*I’m not gonna get political here, but I am going to say that too much of perceived value of how well society is doing is based on corporate shareholder value, which is antithetical to the village mentality and incentivizes things like rent seeking
You see this dynamic in sports too. Sure, the stars fill the highlight reels and sell the jerseys, but championships are usually won by the supporting cast: the reliable utility infielder who plays three positions, the bullpen arms who keep games close, the backup quarterback who keeps the season alive when the starter goes down.*
*I’m generally exhausted by the still remaining 1972 Dolphins celebrating their undefeated Super Bowl-winning season every year, but they’re a perfect example. Their star QB Bob Griese went down early in the season and didn’t come back until the AFC Championship game. Backup (and very old by 1970s football standards) Earl Morrell won the majority of the Dolphins games that season at QB
When organizations only “bet” on their stars, whether it’s a company overindexing on its top sellers or a sports team mortgaging its future for one superstar, they create fragility and leave themselves exposed to all kinds of common issues. What happens when that star gets hurt? Leaves for another team? Burns out?
I’ve seen this in our business over and over again. Teams that only reward the top performers often struggle with morale, retention, and culture. They churn through talent. They become brittle. The “glue people,”* the ones who keep the trains running, mentor new hires, and quietly solve problems, leave because they feel invisible, underappreciated or lost. And then leadership is shocked when results crater, because the very people who made success sustainable have been neglected.
*I’ve spoken before about how much I value people who “brown bag” it to whatever it is they do. These are the people worth focusing your time and energy in.
Compare that to organizations that celebrate contributions at all levels. Not just the sales leaderboard or the quarterly revenue hero, but the SDR who books the meeting and fosters the day to day relationships, the ops person who gets the campaign live and makes the optimization that changes the trajectory of the campaign, the account manager who keeps the customer happy. Those teams weather downturns, transitions, and even market shocks far more effectively.
The difference comes down to mindset. Betting is about optimizing for the short-term. You double down on the players or reps who have the best odds right now. You lean hard on the obvious markers of success: closed deals, touchdowns, home runs.
It works if all you care about is the immediate outcome.
Building, by contrast, is about designing for resilience. It’s not as sexy. It requires patience. It requires investing in depth, redundancy, and interdependence. And to finally beat this baseball analogy to death, it requires recognizing that the boring, unglamorous work of the farm system, the bench players, the infrastructure is what keeps you competitive year after year.
The San Antonio Spurs are a perfect case study in this philosophy. They weren’t just a “bet” on Tim Duncan — they were a system. A culture. They built around teamwork, player development, and selflessness. The result? A dynasty that lasted nearly two decades.
The same logic applies in business. The betting mindset says: “The top 10% of reps bring in 80% of the revenue, so let’s just back them and hope for the best.” The building mindset says: “Let’s support the SDRs, the operations team, the account managers, because they’re the ones who make that 80% possible in the first place.”
The key insight is this: the betting mentality is extractive. It asks, “How can I maximize what I get right now?” The building mentality is regenerative. It asks, “How can I create a system that keeps delivering value tomorrow, and the day after that?”
Because winning isn’t just about this quarter or this game. It’s about whether your team can sustain performance across seasons, market shifts, even generational transitions. And that requires investment in the less visible roles, the ones that don’t get the headlines but make the machine work.
So here’s the challenge: are you thinking like a bettor, always putting your chips on the fastest horse and hoping today’s edge pays off? Or are you thinking like a builder: investing in depth, cultivating resilience, designing for the long term?
Perhaps if we all started thinking a little more like builders, we’d create teams, companies, and communities that scale and last longer than the average NFL quarterback’s career.
Because while the race may go to the swift and the battle to the strong, the future belongs to those who build together.
OK, folks, we’ve got news this week:
The teaser for “Leadership In” featuring Greg MacDonald and me is live and can be found here - you can catch episode 1 with Ronan Shields of Digiday on Tuesday Sept. 16.
Additionally, I’m thrilled to announce that Stacy Bohrer and I will be going into production on “Beta Tested” - a podcast diving deep on the realities of being a woman in technology: the victories, the pivots, the invisible labor, the leadership leaps, and everything in between - very shortly. A 10-episode season will be coming later this fall.
If you’ve got thoughts about who might be a great guest for either of these, please reach out here for Leadership In and here for Beta Tested.
Finally, I’m looking to continue to scale OK, So … Media as a venture. Part of what I’m trying to do OK, So … is bring airtime to underserved or under heard voices, so if you’ve got an idea that you’ve been struggling to bring to life, let’s at least talk. I can’t promise that it’ll have a home here, but I can promise that I’ll listen.
That’s all for this week. Until next time, friends.