The Spirit of the Underdog

I love the underdog. Always have. Ever since a team of misfit little-leaguers coached by Walter Matthau made their way to the bright lights of the Astrodome. The sixteenth seed that beats a number one in the NCAA basketball tournament; the overlooked college quarterback who ends up winning six Super Bowl rings; the young woman reminded she was too muscular to be a ballerina only to become the first African-American principal dancer: Who doesn’t love the underdog? It’s no fun to watch big ole' Goliath beat up on lil' David. Goliath is supposed to win. But when the little guys occasionally pull off a victory, it’s as if their stories grant me the hope that I too have a shot against my Goliaths. But are there any tips to be gleaned from the underdog success stories?

There is a set of advantages that have to do with material resources, and there is a set that have to do with the absence of material resources—and the reason underdogs win as often as they do is that the latter is sometimes every bit the equal of the former. Malcolm Gladwell

I read that in military battles the underdog, the unit with fewer material resources, has, in more modern times, won approximately half the battles. It’s surprising that the results are closer to a coin-flip than a clear advantage for the better equipped, but as Mr. Gladwell points out above, more isn’t always better and, counterintuitively, there can be just as many advantages in having less. It’s like those sporting events where the underdog is about to pull out an upset win and an announcer yells, “They’re playing like they’ve got nothing to lose!” The implication? Freed from the burdens of expectation and pressure, the underdog can just focus on playing the game. While playing the game is much better than thinking (and thinking-squared’s pal, overthinking) about playing the game, nobody plays the game to lose, so the underdog does, technically, have something at risk. And while it might seem heroic to go out and just play with reckless abandon against a much stronger, superior-funded opponent, doing so, unless you're in a movie, often leads to overwhelming defeat. For the favorites, more material resources often mean more ways to beat the underdog. So can there really be an advantage in having fewer material resources?

The more constraints one imposes, the more one frees one’s self. And the arbitrariness of the constraint serves only to obtain precision of execution. --Igor Stravinsky

By definition, an underdog is constrained. The trick then is to see the freedom in those constraints like Mr. Stravinsky suggests. While constraints leave you with smaller margins for error, they also release you from F.O.M.O. and the paralysis that can sometimes stem from having to consider all those the options. Absolved from obsessing about whether or not you've made the perfect choice (because you probably don’t have the same range of choices, at least not compared to the resource flush Goliaths), you can then just focus on executing the strategies that you do have. Like the old Bruce Lee quote about being afraid of, not the person who has practiced ten-thousand different kicks, but rather the person who has practiced one kick ten-thousand times, as an underdog, you get the chance to practice precision in the execution of those more limited strategies.

The first underdog tip is to embrace your constraints. Instead of focusing on what you don't have, do what you can do with what you do have. Then get to executing the doing precisely.

So you have to figure out what your own aptitudes are. If you play games where other people have the aptitudes and you don’t, you’re going to lose… You have to figure out where you’ve got an edge. And you’ve got to play within your own circle of competence. Charlie Munger

When Bill Walsh, one of the greatest N.F.L. head coaches of all time, was an offensive coordinator with the Cincinnati Bengals, he had a quandary. The Bengals did not have a very good running game because their offensive line was much smaller than the defenses that they faced, so Coach Walsh realized they’d have to throw the ball more. Most teams had strong-armed quarterbacks that could chuck the ball deep down the field. Unfortunately, Coach Walsh had a quarterback, Virgil Carter, who was smart, quick on his feet, and calm under pressure, but with, ahem, a more modest arm. (Per coach Walsh, somebody told Mr. Carter, "Virgil, if you want to throw the football more than twenty yards you better fill it with helium." Ouch.) Nevertheless, Coach Walsh began to create plays that tried to make the best of Mr. Carter’s abilities: “I used all that width [of the playing field]… in designing plays, thus turning the approximately 15 yards of depth— Virgil’s most effective range — and 53.3 yards of width into a wide-open war zone being hit not by long bombs but short ones.” By doing so Coach Walsh kept within his team’s “circle of competence” and in the process created an offense that would change football for decades and help his 49er teams win a couple Super Bowls. All from, as Coach Walsh describes it, taking “a situation that had little going for it and trying to get something going.”

What’s more striking is how Coach Walsh ended up also changing the “playing field” in the process. The norm at the time was to attack the football field lengthwise, either running up the middle of the defense or deep passes, but he found that he could just as easily (and more capably with his team) attack it widthwise. I don’t want geek out on the concept of rethinking “space” too much, but Walsh’s reconceptualization of the playing field reminds me a little bit of how the fighter pilot John Boyd changed the rules of air combat. Like Coach Walsh, Mr. Boyd and the Americans were facing the more powerful and heavily armed MIG planes during the conflict in Korea. Had the Air Force stuck with the more traditional (more "linear") conceptualization of space, an approach that would have favored the bigger MIGs, the Americans might have suffered heavy losses. Mr. Boyd, however, wanted to leverage the agility of the American Sabre planes (with a full hydraulic system and 360 view bubble top compared to the partial hydraulics and narrower sight lines in the MIGs). With their planes, American pilots flew in atypical patterns (sometimes even improvising) in an effort to keeping "changing the playing field” and chip away at the MIGs' inherent strengths. The strategy worked. As both men learned, there is always a countermove.

The second tip of the underdog is that you can’t play Goliath’s game, at least not the way that Goliath does, so you might as well play yours. Better yet, flip the playing field (dimensions, space, time-horizon) so that Goliath has to play your game. Find those countermoves.

We know our revenue is a challenge and an obstacle to overcome, but you have to embrace the challenge, form your own identity and stay true to who you are. We know there are challenges we face financially, but we don’t let ourselves be limited by them. We use them to inspire us, to spur us to work harder and be more creative. Chaim Bloom, then Tampa Bay Rays Senior Vice President of Baseball Operations.

Over time, the underdogs that continuously have success can start to look like Goliaths in their own right. They get the big sponsorship deals, win primo television contracts, erect top notch facilities, as they start to become flush with the material resources that often accompany repeated successes. But what happens if the material resources don't come and you’re constantly having to, as 2Pac once said, make a dollar out of fifteen cents?  

Enter the Tampa Bay Rays. Historically, the Rays have had some of the lowest payrolls in baseball, total figures that look like a rounding error compared to other teams. Yet they’ve found ways to beat the New York and Boston Goliaths they face annually by pressing the edge of innovation. (As of this writing they're also in first place in the A.L. East. Holla!) Hate how managers used to bring in a pitcher to face a one batter and then bring in another pitcher to face the next batter? Rays. (Major League baseball hated that too and changed the rules last summer to “speed up” the game.) Start a game with an “opener” that throws maybe an inning or two and then sprinkle in pitchers the rest of the game instead of bringing out the old school starter that throws 9 innings and 140 pitchers? Rays. Funky infield formations where there’s such an extreme shift that it looks like a batter can just tap a single down a wide open third base line (but he doesn’t because he lives up to his statistical tendencies)? Rays. Tampa Bay has had to continue to innovate and be more creative in order to keep finding ways to beat their comparatively resource-rich competitors.

But the Rays didn't stop at changing how the game is played. They’re also changing the who's that are playing the game. A super fast center-fielder that can track down almost any ball but doesn't have the best of batting averages? Sign him up for the number of runs he’ll save by getting to those hard to reach balls. Mr. Utility Player who can play every position on the field? The Rays were finding those jacks of all trades long before the rest of the league caught up and were plugging them into the roster like some kind of physics formula. Cast off pitchers from other teams that have higher earned run averages but can throw a fastball that spins a certain way? Bring them in and put them through “the Rays system” of pitching recalibration. As Mr. Bloom notes, “We feel very strongly about our ability to get the best out of guys.” Ability might be an understatement as the Rays are like those M&A conglomerates that buy up companies left and right in order to apply some proprietary lean manufacturing wizardry that cranks out greater efficiencies (and productivity) from their acquisitions.

The third tip of the underdog is to keep innovating, continuously developing. Not only the what but also the who. Keep tapping into that creative spirit, a very renewable resource.

We pride ourselves on being as ahead of the game as we possibly can, but what gets lost in that is it’s not just about the ideas. It’s about who’s implementing them, how we work together and the trust that we have in each other. That’s not to say we do that perfectly, but hopefully if we are taking care of that culture in the right way, we’re creating an advantage that is not easily mimicked. Chaim Bloom

At some point the underdog can become so successful that they can’t be considered an underdog any longer. And winning seasons often draw the envy and attention of the Davids or Goliaths that are trying to find a way to find their own championship seasons. In today's information and knowledge economy, technical advantages don’t last as long as they used to. (And the timeframe keeps shrinking.) What was once an underdog's advantage can quickly become yet another way for the big guy to beat up on the little guy. And once everyone's doing it, the it is no longer an edge, but rather just another thing you have to do just to keep up with the benchmark. But as Mr. Bloom notes, one advantage that isn’t easily replicated or cloned is the advantage of taking care of the people. The people and the culture. The culture and the mindsets. Curate of all three and you can go pretty far. Rays pitching coach Kyle Snyder said it best in describing the Rays' formula:

It’s a combination of a lot of things. There is a lot of hard work and collaborative effort among our scouting and our player development, and [it's] really just building relationships....

And that's probably the final tip of the underdog. The people. Isn't it always the people? Finding your people and your tribe of fellow go-getters. Look, we can't do this alone as much as on occasion, as an introvert, I sometimes wish we could. We underdogs are going to need to find people who are going to challenge our thinking, help us see the freedom in our constraints, get together with us, and, like Vanilla Ice used to say, stop, collaborate, and listen. In return, we're going to need to be the type of people who can help other underdogs find their grooves, their circles of competence, their countermoves. Collectively, armed with creative energies and innovative spirits, the underdogs might just be able to band together and change the playing field. It's hard work, a kind of work that requires an investment in communities and cultures, people and mindsets. But the payoff can be so much sweeter than mere material resources.

The final tip of underdog: It's always the people. Find your tribe. Help your tribe. Repeat the virtuous cycle.

Please note that the opinions expressed herein are mine and mine alone and do not represent the opinions of and are definitely not endorsed by my employer Raymond James. At the end of the day, I'm just trying to learn as much as I can and share what I've been lucky enough to learn. Thanks!