An Ode to the Hidden Strength of the Underdog

“It was not the privileged and fortunate who took in the Jews in France. It was the marginal and the damaged, which should remind us that there are real limits to what evil and misfortune can accomplish. If you take away the gift of reading, you create the gift of listening. If you bomb a city, you leave behind death and destruction. But you create a community of remote misses. If you take away a mother or a father, you cause suffering and despair. But one time in ten, out of that despair rises an indomitable force. You see the giant and the shepherd in the Valley of Elah and your eye is drawn to the man with the sword and shield and the glittering armor. But so much of what is beautiful and valuable in the world comes from the shepherd, who has more strength and purpose that we ever imagine.”-Malcolm Gladwell, David and Goliath: Underdogs, Misfits, and the Art of Battling Giants

Malcolm Gladwell just wrote a new book. I’m sure you’ve heard of it. Everyone hears about it when Malcolm Gladwell writes a new book. Surely, you have to at least skim it to understand which new theories your sophisticated friends are spouting at cocktail parties. Perhaps, I am too harsh. After all, I had only read Tipping Point previous to this one. Regardless, I’m going to explain why you need to read his new book, David and Goliath.

I’ve been reading up on the benefits of smaller armies. One of the big examples that comes to mind is that of Napoleon. Through his radically different war tactics, he was able to conquer vast areas of Europe using fluidity and smaller regimes that are more easily able to react to changes. The parallel to our time that is usually produced is that of Google, always adapting, forever fluid.

Then, of course, there is the cultural narrative that we assign to the “underdog.” You’ve seen it in a million sports movies, and you’re always rooting for the underdog to come out on top. You want Rudy to win. Those kids in Coach Carter, you’re on their side. Disregarding sports films, you’re still rooting for the unexpected, the challenging. Part of the reason that I balled like a baby at the end of American History X was because I expected the underdog to change his ways and turn his life around; right as he was rising above his obstacle, he was taken away. (Maybe that’s a spoiler, but I’m sure it was vague enough for you too enjoy the movie still.

We root for these heroes because we think they need our support. We think that it is them against the world, and we assume their side has less artillery. David and Goliath peers behind that image, and instead, looks at the reasoning for so many underdog victories.

As it turns out, there is such a thing as a desirable difficultly. I’d always suspected it, but as he is famous for doing, Gladwell found an eloquent way to put it into words and back it up.

One thing that I’ve been doing for a while is reading Stoic philosophy (Aurelius, Seneca, etc.). Why? Because I’m a nerd and because it teaches simple, day-to-day lessons, usually involving our perceptions and reactions to obstacles.

“Our inward power, when it obeys nature, reacts to events by accommodating itself to what it faces – to what is possible. It needs no specific material. It pursues its own aims as circumstances allow; it turns obstacles into fuel. As a fire overwhelms what would have quenched a lamp. What’s thrown on top of the conflagration is absorbed, consumed by it – and makes it burn still higher.”-Marcus Aurelius

It’s important to view ‘obstacles as opportunities’, as Tucker Max would say. It’s also important to realize why a lot of these obstacles are opportunities, in the specific sense. Dyslexics like Richard Branson learn to compensate by listening and taking risks. Traumatic childhoods and lost parents produce a mental toughness and obstinate that facilitates ambition and goal reaching. The down and out, disheartened, and oppressed often resort to ‘trickster’ techniques; things that allow them a leg up on their oppressors. It’s this creativity that kills sacred cows and produces innovation.

These things happen on a daily basis. Let me show you:


-The ski racing company that I work for is smaller than Spyder. This, however, is an advantage in the fluidity of our marketing strategy and the personal impact we have with customers. Everything is personal and the loyalty for the brand is tremendous. Even without the massive marketing budget of competitors, we are forced to innovated on the fronts of social media and public relations, which are often times more effective than traditional advertising.


-Craft beer. A few weeks ago my academic adviser and I were talking about craft beer (What else? Classes? No, thanks.) He told me a story of one of his favorite bars in Milwaukee, Roman’s Pub, and how before the craft beer revolution, they had to stock the bar with craft beer. Why? Because the owner of the bar “didn’t get along with” a major distributor of macro beer, and allegedly told them to go to hell. From then on (1996), they stocked with local supply and specialty brews and became an early adopter of the upcoming trend in the beer world. Worked out pretty well for them, I’d say.

-I often lament the fact that I grew up in such a small town in the middle of nowhere. I’m not a fan of that fact. However, it did afford me opportunities that I couldn’t articulate before I read this book. Where my school was so small that it didn’t even have a soccer team (wtf, right?), this obstacle was also an opportunity. In the book, Gladwell talks about the benefits of being a big fish in a small pond. Certainly then, starting a band in such a small town made me a huge fish in a pond with no other musical fish. This was encouraging. Because of this, I had an identity I probably couldn’t have afforded growing up in New York City. Maybe. I mean, you can never say for sure. But, despite growing up in a small town in the middle of nowhere, I think I turned out alright and decently cultured, too. Maybe growing up there allowed me to appreciate exploration and other cultures more. I don’t know. But the obstacle part of the equation is overrated.

I know, if you tried, you could think of a million more examples of difficulties being used as benefits. This is a healthy way of viewing the world. Some circumstances are unavoidable. What you do with your circumstances is what matters. To end with another from Marcus Aurelius: “You have power over your mind – not outside events. Realize this, and you will find strength.”


Public Relations Lessons from the Late Great John F Kennedy

Politicians are excellent at a certain rhetoric device called “framing.” They know how to switch conversations to more favorable topics, they know how to avoid the ugly answers, and sometimes they can flip a public relations disaster into an underdog victory.

On the 50th anniversary of his assassination, I’m going to show you how JFK did just that, winning over the audience as an underdog even after some sharp criticisms from Harry Truman.

Background story:

In 1960, just before the Democratic National Convention, Harry Truman openly criticized his own party for favoring JFK’s presidential nomination. He attacked JFK on multiple fronts, including his age, lack of experience, his powerful political backing that “pressured” votes, among other things. This was the last Democrat president to hold office, not only contributing bad press to JFK’s political career, but asking him to step down from the Presidential race. Naturally, this was a public relations disaster

Kennedy now had a couple of options. What would you do if a leader in your industry attacked the very core of your business, of your character? Would ignoring it help you or hurt you? Is there a chance you could position yourself in a way that leverages the criticism as an advantage? You already know what I’m going to say.

Using some crazy form of PR Jujitsu, JFK took everything Truman said, and using the weight of Truman’s own words, came out on top. He presented his weaknesses as strengths. He did this on live television in the style of a Western showdown. It was dramatic. The end result was that JFK positioned himself as an underdog hero representing the emerging generation, his “new frontier.” And of course, he won the presidency.

So how did he do it? What lessons can we take away from his victory?

(The implicit 1st rule of his success here is that you must view your obstacles as opportunities. If the paradigm is always pointed to the positive and the possible advantageous outcomes, it is not difficult to turn a negative situation around.)

1. Pick Your Battles Wisely

The internet has made PR as confusing as it has ever been. At any time, from any angle, your image could be attacked. How do you deal with that kind of pressure?

Evidence suggests that often you can ignore it.

Ryan Holiday recently wrote a brilliant article about negative press. In it, he says that the first lesson is, “A significant portion of all criticism (especially online) is just trolling. It depends on and desires your participation. Opt out and you’ve robbed it of the oxygen it needs.” Smaller people bate larger people for a response. Don’t acknowledge it. You’re simply giving fuel to criticism that otherwise would not have taken off. Jay-Z never needs to acknowledge some loud mouthed no name, because nobody hears the dude. But if he does acknowledge, the position of the no name has suddenly been given a platform.

Look at it this way: you can save your energy for bigger battles. You can save your energy to make a better product.

However, JFK was criticized by the former president of the United States, the last Democrat to hold that office. That he chose to respond proves that Kennedy knew how to pick his battles wisely. John Hellman wrote that his response was so effective that his team was “grateful the attack had given them such a well-publicized opportunity to confront doubts about Kennedy’s qualifications.”

2. Play by the Rules of the Real World

There are about two schools of thought regarding public relations. Option A: all press is good press; Option B: positive press is good press. The real world is not so cut and dry. Wouldn’t it be nice if all of your press was positive? If everybody you knew said nice things about you all the time? Of course! But if the world is anything like the YouTube comments section (not the new boring one), it is filled with trolls, who are embittered and scornful people. The world is also filled with sneakier villains: competitive friends, friendly competitors, attention seeking (read: click baiting) journalists, and faulty team members. And sometimes, shit just happens. You’re going to want be able to respond when something does not go according to favor. It’s something that is really tough to plan for; I’m sure JFK didn’t expect Truman to fire into him with complaints. But bad news is something you should expect.

Sidenote: according to a study published in 2010 (Berger, Sorensen, Rasmussen), sometimes negative press can increase sales, especially when dealing with smaller brands. Here’s the link.

3. “Always Create Compelling Spectacles.”

Robert Greene’s 37th Rule of Power, “Always Create Compelling Spectacles,” comes in quite handy. Since we’ve already established that this is a necessary battle and that, in reality, there is no cut and dry way advice for a response, now we have a story to tell. And we’re going to make this story exciting. Ryan Holiday’s advice is perfect: “If you are to respond, remember this simple rule: The response must be more interesting than the initial salvo.”

John F. Kennedy baked compelling spectacles into all of his actions, which contributed to his public image as a young war hero, fighting for the new frontier for the next generation. This particular event was perfect for bolstering his image.

John Hellman said that Kennedy “chose not to downplay Truman’s remarks, but rather to heighten them into a dramatic crisis.” Furthermore, he said “Kennedy transformed the political problem into a dramatic crisis evoking the showdown toward which the western movies of the day invariably moved.”

Check out Truman’s initial speech:

Now watch Kennedy’s response:

Don’t have time to watch? Here’s what happened:

Kennedy confidently stated: “I do not intend to step aside at anyone’s request.” He then went on to say he had “encountered and survived every kind of opposition,” re-positioning himself as a bold war hero. Kennedy went point by point against Truman’s criticisms, and without emphasizing what Truman said, reasserted his own strengths. He expertly framed the situation in an exciting way. Which leads to the next tip:

4. Learn How to Frame Stories

“If we are to establish a test for the presidency, whereby 14 years in major elective office is insufficient experience, then all but 3 of the 10 possibilities mentioned by Mr. Truman last Saturday must be ruled out. All but a handful of our presidents, since the very founding of our nation, should be ruled out. And every president elevated to that office in the 20th century should have been ruled out, including the three great Democratic presidents, Woodrow Wilson, Franklin Roosevelt, and Harry Truman, himself.”-John F. Kennedy (source)

“Kennedy shaped the problem of Truman’s attack into a scenario pleasing to both himself and the public.”-John Hellman

At stake was Kennedy’s reputation and image, and he was vulnerable. Here he stood, directly preceding the nomination, being harshly criticized by the most able person to do so: the last Democratic president. Truman presumably was everything that Kennedy was not: experienced, tactful, and most importantly, organic.

See, Truman actually had a point in his critique. He described Kennedy as a “victim of circumstances,” and blamed “some of his overzealous backers.” He actually said that Kennedy demonstrated ability and energy, but then turned to ask if Kennedy was ready for the country, or if the country was truly ready for him. Truman then urged Kennedy to be patient with his ambition. He hoped that someone with “the greatest possible maturity and experience would be available at this time.”

Kennedy’s response: flawless. He demonstrated his energy and vigor by framing his lack of experience by comparing it to Truman’s own amount of experience. Kennedy’s point: if Truman criticizes Kennedy’s amount of experience, then he is hypocritical. Smarter still, Kennedy ignored what he couldn’t frame: his candidacy’s “overzealous backers.” Instead, he focused on his own battles and experiences and ended up sounded brave, conversely making Truman sound old and bitter. This certainly reflected on his campaign image of the youth leader bringing America into the “New Frontier.”

5. Stay Cool: Smile Through It.

“Just remember this: the cliche “all press is good press” is a cliche because it is true. In six months, no one will remember particulars of a news story you’re freaking out about right now–it probably won’t even make it on Wikipedia. Unless you make it worse by overreacting, saying something stupid or pissing the journalist off even more”-Ryan Holiday

It’s probably a smaller issue than you’re making it out to be. Even if it’s a big deal, put on your actor’s mask and play it cool. Don’t ignite the fire; the spark will die out if you let it. Let’s say a small fire has been kindled: calmly put it out. What does freaking out do? Even if you get the issue under control, you look like a disheveled fool doing so.

John F. Kennedy was the denotation of confident the day he called his July 4th press conference. John Hellman wrote, “Kennedy’s heavy-lidded, detached stare and slightly ironic smile also suggested the young rebel’s attitude.” Robert Greene echoed this, saying he resembled James Dean, “particularly in his air of cool detachment.” Hell, Kennedy was known for his coolness. During the famous 1st televised debate against Richard Nixon, he showed up tanned, toned, and relaxed. This contrasted with a sweaty, anxious Nixon. This leads to the lesson: whether it is a crisis or not, act like it is not. The way it tends to be, you decide the tone of the confrontation. If you’re unreasonably emotional, prepare for some more shitty backlash. Kennedy played it cool, he parlayed his weaknesses into strengths, and he won the crowd. Heed his lessons, protect your image, and master every public relations event, planned or not.

Why Musicians Make the Best Entrepreneurs

Take a moment to moment to reflect on some of your favorite bands. Chances are, at least one person in at least one of those bands is involved in a successful business venture aside from the band. Tom Delonge founded both Macbeth and Modlife while balancing two bands and a family (in addition to a few past ventures). Travis Barker started successful clothing company Famous Stars & Straps. Kanye West is yelling on rooftops about his creative agency. We all know Jay-Z’s Story. There are thousands of examples of these. 50 Cent, P. Diddy, Eminem. There’s also this list. There certainly seems to be a trend.

So, why do musicians consistently make successful entrepreneurs?

Musicians make good entrepreneurs because musicians are entrepreneurs. At a a very base level, the best musicians engage in idea conception, strategic planning, product design, internet marketing, sales, negotiation, self-education, investment, fundraising, and so many more activities strikingly similar to those we consider entrepreneurs.

When I was in a band, I was forced to learn a myriad of skills that helped me get where I’m at today. I learned basic graphic design and Photoshop skills. I learned how to negotiate pricing with venues. I learned leadership; it’s hard to find a good drummer, let alone run regular band practices and mediate problems between oh so sensitive musicians. I learned how to “create compelling spectacles” as Robert Greene says. Like P.T. Barnum says, “without promotion, something terrible happens…nothing!” My public relations jobs were easy after my time as a musician.


So, I’ve done a bit of research, and here’s what I find musicians have in common with entrepreneurs:

1. Self-Motivation

“Fortune always favors the brave, and never helps a man who does not help himself.”–P.T. Barnum

One thing the two have in common: a lack of a safety net. You don’t clock in and out of work until you hit 40 hours. You don’t stop working on the weekend. You’re a fucking hustler. I just talked to a friend of mine, a jazz musician, that says every other jazz musician he knows plays in at least 4 bands. How would you balance 4 different jobs? They don’t have to do it, either. It’s arguably easier to wake up every morning for a secure job that you know you have to be at, than it is to force yourself to wake up early enough to not only accomplish all of your tasks, but to conceptualize what those tasks are. Nobody gives you an instruction manual when you’re a musician or an entrepreneur. Business books can help inspire you or give you ideas, but they can’t put willpower in your life. Musicians and entrepreneurs both require innate motivation and independence in their pursuits.

2. They’re Disruptors

“The fishing is best where the fewest go and the collective insecurity of the world makes it easy for people to hit home runs while everyone is aiming for base hits.”-Tim Ferriss

There’s no need for a new start-up if there’s nothing to fix, right? True, but there’s always something to fix, right down to daily annoyances. Nest is a company that is reinventing things that annoy the shit out of me, like smoke detectors and thermostats. Similarly, music has a history of disruption. What’s cool about music, though, is the product itself isn’t what is to be fixed. It’s culture. The history is much deeper than this example, but Woodstock was a great example of this. Punk rock, both at its worst and at its best, seeks to reconstruct (or destroy) culture. Hip hop gave a voice to the voiceless. Entrepreneurs seek to simplify, they seek to make things better than they currently are. Musicians seek honesty, they seek a fundamental truth that will resonate with people. Both seek to do what has never been done or said before.


3. Public Relations and Branding

“There’s only one thing worse than being talked about, and that is not being talked about.”-Oscar Wilde

Say what you will, but Miley Cyrus is smarter than you. Or, whoever is marketing for her is. They know that, especially in today’s media landscape, if you’re not doing something interesting, you won’t be talked about. And if you’re not being talked about, you lose. Most musicians don’t have the massive platform that Miley Cyrus does. That’s okay. They still understand the power of branding. Take Travis Barker: Dude looks cool as fuck all the time. The mohawk, the tattoos, the sleeveless tees? They’re all assets that help build the brand of FS&S. Did you know Terry Richardson used to play bass in a band. His work, certainly controversial, is unique and well branded, and he carries himself with brand-consciousness as well. There’s a lot to the marketing mix that musicians, as well as entrepreneurs, don’t understand. But they tend to be damn good at crafting a brand.

4. Leadership and Group Cohesion

“The one quality that can be developed by studious reflection and practice is the leadership of men.”-Dwight D. Eisenhower

Not all who join bands are or will be great leaders, just as not everybody that works for a start-up will be. But the kid who, after practicing his instrument for hours a day, leaves the basement to phone his band members to organize weekly band practices will learn a lot about leadership. For starters, this musical CEO will learn the value of good co-workers. Everyone who’s played in a band has had the delightful experience of playing with a lazy bassist, an egotistical guitar player, or a drummer that skips practice. Leadership is when someone decides to cut the poison from the product. Good leaders in business and music surround themselves with amazing people, because that makes them do amazing things. As Tim Ferriss says, “you are the average of the five people you associate with most, so do not underestimate the effects of your pessimistic, unambitious, or disorganized friends. If someone isn’t making you stronger, they’re making you weaker.” A good band leader learns how to pick ‘em right and how to organize ‘em once they’re there. They develop a talent for delegation and for presenting clear and effective goals. They learn how to act on stage, to speak to a crowd, and how to carry the band through a performance. An early stage start-up founder that picks poisonous co-founders and employees is asking for a disaster. That same CEO needs to know how to lead her team using clear cut communication and effective goal setting. I cannot emphasize enough much a musician can learn about business leadership.