What Is Your Startup CEO Superpower?

Woodcut style representation of George Washington crossing the Delaware river.

Maybe the best piece of art I’ve ever seen is the musical, Hamilton. Thanks to Blossom’s insistence, I was fortunate enough to see the original cast in New York, and then see the touring cast in San Francisco. Not surprisingly, the original cast was much, much better.

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The musical is the incredible story of Alexander Hamilton and the birth of the United States. The musical was created by Lin Manuel Miranda. What I’ll bet you didn’t know is that Miranda is a great business philosopher too. I’ll explain how in a minute.

My two favorite songs in Hamilton are both about George Washington. The first song I love, “One Last Time,” because Chris Jackson’s performance as George Washington is so powerful. Here’s a clip of Jackson and Miranda performing “One Last Time” at the White House for President Obama. It moves me to tears each time I watch it:


My second favorite song in Hamilton is called, “Right Hand Man.” I like Right Hand Man because I can envision the song in a totally different way (heavy rock) versus the rap it is done with in the show.

More important than my musical wannabe stuff, the lyrics tell the tale of a true startup (in this case, the United States of America):


We are outgunned
We gotta make an all out stand

Those lines could have spoken by any startup CEO because you are outgunned, outmanned, outnumbered, and outplanned. How do you win with all that going against you?


You Need Laser Like Focus To Win In The Startup Game.


I was talking with a CEO about his business the other day.   I asked him a very simple question, “What market are you targeting?”

“Oh, that’s the great thing,” he said. “We have so many markets we can go after.”

Then the CEO started listing off the markets.

Then I asked, “What market are you going to attack first?”

“All of them.”

That’s the wrong answer.   The entrepreneur was likely going to fail and he didn’t even know it.

Let’s go back and use some of the lyrics from “Right Hand Man”.


Remember, you’re outgunned.


There are larger competitors who are operating in your broad space. And they have a lot more guns (products, whatever that might be) than your small company does.

George Washington realized he couldn’t fight a conventional war against the British and win. He would have been crushed. Just like any good startup CEO, Washington used guerilla tactics to win.

The way to victory isn’t going head on versus your larger competitors. You usually get killed doing that. Instead you look for the areas of weakness and attack there.


Remember, you’re outmanned and outnumbered.

The larger competitors in your space have a lot more resources (people) they can put on any project. That makes competing against large competition such a challenge.

Washington preferred engaging the enemy on his terms because it was the only chance he had.   You need to do the same thing as a startup CEO. In fact, only engage your competitors when you know the odds are stacked in your favor.


Remember, you’re outplanned.


You’re large competitor is better at what they do than you are. That’s why you’re outplanned.

Sounds pretty bleak, doesn’t it?

You’re competing against companies with more resources than you have. You’re competing against companies with more products for your customers to choose from. And you’re competing against companies that are better at what they do than you are.

That’s the life of a startup. But there is an answer and Wee Willie Keeler has it.

Keeler is another great business philosopher. In fact, Keeler’s one piece of business advice is probably the single best advice for any startup CEO to follow. I’ll get to that in a bit.

Keeler was a professional baseball player from 1892 – 1910. Everything about Keeler reeks of a scrappy startup:

  • His height was 5’ 4.5”
  • His weight was 140 pounds

Keeler was one of the smallest players in the game.   Yet, he was such a great baseball player that he ended up in the baseball Hall of Fame.

How did Keeler do it? Keeler was just like a scrappy startup. Keeler originated the famous “Blue Ocean” strategy years prior to the popular 2005 book of the same name.

Keeler’s advice to hitters, "Keep your eye clear, and hit 'em where they ain't" is the Blue Ocean strategy that is ideal for startups to follow. Let’s break it down in a little more detail: 


Keep your eye clear.


The first part of Keeler’s advice is all about understanding the competitive landscape you are facing. To Keeler, his competition was the fielders and the pitcher he was facing.

You need to keep your eye clear about your competition too. What are they focused on? What do they care about? And, what are they trying to protect? Then… 


Hit ‘em where they ain’t.

Trying to beat established competitors at their own game is really tough to do. I always assume that I’m going up against the best and brightest the competition has because it keeps me sharp. You should too. However…

A much smarter approach is to Hit ‘em where they ain’t. In other words find something you can be unique and great at just like the Blue Ocean strategy.

You should still assume that you are going to have competition because success breeds competition. But you at least have a fighting chance by Hitting ‘em where they ain’t.

When you Hit ‘em where they ain’t, you can develop a true MVP that has flaws. In an established market, you can’t develop an MVP because you’ll need fully developed product(s). And that’s a tall order for any startup to pull off.


We gotta make an all out stand.


Let’s conclude by taking the last piece of Miranda’s advice. Miranda is really saying, emphatically, you need to focus when you’re starting your company if you’re going to win.

Remember, you’re outgunned, outmanned, outnumbered, and outplanned. Then by focusing your great team on this one object, you’ll hit ‘em where they ain’t and have the best chance of victory.


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