How Upstarts Think (And Why You Should Care)

Upstarts think differently. They attack weaknesses, find unique angles, and pounce on opportunities—partly from necessity and partly for effectiveness.

How can the upstarts’ mentality contribute to your career and your business?

How Upstarts Challenge Goliaths

In 1915, two U.S. fruit companies sought to acquire the same five-thousand-acre parcel of land.

One company was the powerful conglomerate United Fruit. The other was an upstart company founded by Samuel Zemurray.

The problem? Two different local farmers claimed to own the no-man’s-land between Honduras and Guatemala.

United Fruit’s approach to the problem was what you’d expect from a bigger-is-better behemoth: They threw an endless stream of lawyers and accountants at the problem to unearth land deeds, written conveyances, and government documents.

What did Zemurray’s outmatched company do?

He couldn’t play their game. So he didn’t. Flexible, fluid, and defiant, he just met separately with both of the supposed owners and bought the land from each of them. He paid twice, sure, but it was over. The land was his. Forget the rule book, settle the issue.

There’s the “right” way and then there’s the way that works, says Ryan Holiday, self-proclaimed “media manipulator” and author of The Obstacle Is the Way, where this story comes from.

We do something similar in our personal lives and our careers. We often get tricked into trying to play the game on the same terms as the big boys.

We throw our time, our attention, our bodies at problems when the better solution is to take a moment to think about how we can get around, go over or under, or outright avoid certain confrontations.

United Fruit played the multinational corporation game and lost.

Zemurray played the common sense game and won.

This is the advantage of agility. Complex organizational hierarchies don’t know how to be nimble any more.

Whether you’re an employee working for one or an entrepreneur competing with one, confronting behemoths head-on plays right into their hands.

There is another way, the upstart way.

Upstarts Know Size Can Be a Weakness

In Malcolm Gladwell’s 2013 book, David and Goliath, the celebrated writer argues that the party we perceive as being at a disadvantage (the underdog) can, and often does, triumph over the superior foe (the goliath).

Gladwell even promotes the idea of “desirable difficulty,” the notion that certain disabilities like dyslexia can confer an advantage to individuals who learn how to compensate for and overcome them.

This stance has landed him in hot water with some disabilities advocates, not surprisingly.

I’m usually a fan of Gladwell’s work, but even I think he’s taking this line too far.

Instead of focusing on the (supposed) advantages of being the underdog, we should be looking at what’s really going on when David upstarts meet Goliath companies in real life.

That is, superior size and power can be a massive weakness as well as a strength.

Here’s Ryan Holiday in The Obstacle Is the Way once again (emphasis mine):

In fact, having the advantage of size or strength or power is often the birthing ground for true and fatal weakness. The inertia of success makes it much harder to truly develop good technique. People or companies who have that size advantage never really have to learn the process when they’ve been able to coast on brute force. And that works for them … until it doesn’t. Until they meet you and you make quick work of them with deft and oblique maneuvers, when you refuse to face them in the one setting they know: head-to-head.

Netflix refused to take on Blockbuster head-on i.e. with brick-and-mortar stores. Instead, Netflix started by mailing out DVD to its customers—remember those ubiquitous red envelopes? They’re practically synonymous with the mid- to late-2000’s.

In time, Netflix expanded to Internet streaming and original programming, all but leaving DVDs behind.

Blockbuster went bankrupt and got bought up by Dish Network.

Blockbuster could see the writing on the wall years ago, of course, but they were too tied to their then-profitable brick-and-mortar stores to do anything about it.

You can call it an advantage of the upstart, but it’s really a weakness of the goliath: When you have something to lose, you find excuses not to act.

When you don’t, you’re free.

The Percentage of Victories Resulting From Head-on Battles Will Surprise You

What percentage of decisive military victories were a result of direct confrontations?

Would you say 80%?



How about 2%?

In a study of some 30 conflicts comprising more than 280 campaigns from ancient to modern history, the brilliant strategist and historian B. H. Liddell Hart came to a stunning conclusion: In only 6 of the 280 campaigns was the decisive victory a result of a direct attack on the enemy’s main army.

Only six. That’s 2 percent.

If not from pitched battles, where do we find victory?

From everywhere else. From the flanks. From the unexpected. From the psychological. From drawing opponents out from their defenses. From the untraditional. From anything but

Liddell Hart’s counter-intuitive research, discussed here by Holiday in The Obstacle Is the Way, demonstrates that reality never conforms to the plan and why long-term planning is so often a joke.

Big-picture strategists plan for the head-on battle, the straightforward confrontation that never comes.

Upstarts take advantage of this tendency to over-plan for the contingencies you can see, instead of the ones that’ll actually get you in the end.

How you react to this information forms the crux of your strategy, whether its business, career, or personal. You can waste time preparing to fight on the enemy’s terms, or you can focus on making yourself emergent, resilient, and agile.

How to Serve as Guest Chef at a White House State Dinner

What an Upstart Chef Does to Cook at the White House

Photo Credit: The Photo Journey via Compfight cc

Author Frans Johansson tells this story in his book, The Click Moment.

Celebrity chef Marcus Samuelsson took part in a selection process to act as guest chef at a state dinner in honor of Indian prime minister, Mammohan Singh. As a part of the process, sixteen chefs were asked to submit a menu to be judged by President Barack Obama and the First Lady, Michelle Obama.

Every state dinner since 1874 has served French-American cuisine. The expectation was that Samuelsson would follow suit. French-American cuisine, as many of you know, emphasizes meat.

Before starting on his menu, Samuelsson learned a few things, including that the Indian PM was a vegetarian. Samuelsson also isn’t known for his French cuisine. He therefore tossed out French-American cuisine as an option, bucking tradition, and decided to go in a direction that played to his strengths.

In other words, he zigged where the other fifteen contenders zagged. French-American menu wouldn’t distinguish him from his other fifteen competitors, all top chefs in their own right. He needed to be different.

He needed to think like an upstart.

Samuelsson ultimately submitted an Indian-American inspired vegetarian menu with a fish option. He even included ingredients from Michelle Obama’s garden at the White House.

He won.

Like Samuel Zemurray facing down United Fruit, it was a combination of common sense (a vegetarian isn’t going to like a menu that emphasizes meat) and the willingness to do what works instead of what’s “right” (every state dinner in over a hundred years has served French-American cuisine) that won the day.

Your competitors seek out head-on engagements, partly due to a lack of creativity and partly due to their resources advantage.

Upstarts are selectively aggressive and act with deliberate speed where they have an advantage.

You can act like the incumbent, the big dog, the heavy when you are one. But until then, you have to think—and act—like an upstart to succeed.

The Disrupter vs. The Complacent CEO: Which Persona Runs Your Life?

Ryan Holiday in The Obstacle Is the Way nails why this all matters to you:

While overpaid CEOs take long vacations and hide behind e-mail autoresponders, some programmer is working eighteen-hour days coding the start-up that will destroy that CEO’s business. And if we were honest, we’re probably closer to the former than the latter when it comes to the problems we face (or don’t face).

While you’re sleeping, traveling, attending meetings, or messing around online, the same thing is happening to you. You’re going soft. You’re not aggressive enough. You’re not pressing ahead. You’ve got a million reasons why you can’t move at a faster pace. This all makes the obstacles in your life loom very large.

For some reason, these days we tend to downplay the importance of aggression, of taking risks, of barreling forward. It’s probably because it’s been negatively associated with certain notions of violence or masculinity … Be deliberate, of course, but you always need to be moving forward.

Time to confront the truth:

Are you aggressive enough in your life? Your career? Your business?

Are you the upstart or the complacent CEO?

Top Photo Credit: _Hadock_ via Compfight cc

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