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For entrepreneurs: A story about risk and reward from Broadway

Being in the right place, at the right time is not something that a VC can model or that an algorithm can calculate

(CACAROOT / ADOBE STOCK)
(CACAROOT / ADOBE STOCK)
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Normally I try to explore the puzzle of entrepreneurship writ large. But sometimes, you just have to go with the flow and wonder at the unknowable world.  

My bride and I went to New York City for a week. You know museums, theater, old friends, some deals and some meals.

When I was much younger and in Hollywood, I spent a few months working with Billy Wilder, the film director, on one of his films, so given the chance to see “Sunset Boulevard” (arguably his greatest movie) reimagined as a musical on Broadway, starring Nicole Scherzinger, well we were not going to miss that.

Seats toward the back on the aisle, all good. Open the program, and we see that the male lead, the Joe Gillis character, is going to be replaced that night by the understudy, somebody named Diego Andres Rodriguez. Well, you don’t win them all, at least we get Nicole.

After the first big song, the couple next to us, stand up and hoot and holler, along with two young women behind them. Enthusiastic is an understatement. Clearly these folks are from some small town, in the big city for the first time, and don’t know how to act in the theater.

Intermission. We have a chat with these neighbors.  

The man asks me how did I like the show, but before I could offer my own appropriately erudite opinion, he adds one more sentence. “The understudy, well, that is our son, and this show is his Broadway debut.”  

I am always astounded at the magic of the world and how it spins. What were the chances? (“Of all the gin ts, in all the towns in all the world, she walks into mine,” Bogart in “Casablanca.”)

The father is a pharmacist, and the family is from McAllen, Texas. And the reason that Rodriguez is singing tonight is the other actor has a bad case of laryngitis, out for two weeks. While I it to knowing nothing, the kid was fantastic, charismatic and will clearly be a star. This is the stuff that dreams are made of.

I am going to suggest that this is also the stuff of entrepreneurship, of startup fantasy and the random spin of the dice.

I have this little AI company. We need to hire a salesperson. We have no clear plan, not sure how to find or even what we need (this is standard for startups), and then someone just shows up, sent by a friend, and is perfect. We didn’t know what we were looking for until it arrived.  

These stories are not unique. They happen all the time. The key is you have to be available, you have to be standing on the platform, so when the train comes through, get on it, even if you don’t know the final destination. Just get a seat.

You can’t be sure another train is coming.

I was recently coaching a successful fellow who was at a crossroad. Take a new job, start something on his own, go back to teaching or consulting or whatever. Not sure what the next five years will look like – or even what he wants them to look like.

Here was the killer sentence. “I have made a lot of other people a lot of money with my skills. I wish I had made more for myself, I wish I had taken a bit more risk.”

I was sad. I have heard this sentence before. Think about Diego Rodriguez. Graduates from Michigan in May, tells his parents he is going to New York to be an actor. Goes to his first audition, gets turned down. Goes to only his second audition for a part. Gets a small walk-on role and understudies the lead, and then the top dog loses his voice.  

That makes no sense. That is not something that a VC can model or that an algorithm can calculate.  

Think about decision-making and risk in your company. How much do you rely on consensus, the wisdom of your crowd? And how big is that crowd?

Herewith a story from Amazon lore. Their model for the correct size of a decision-making team is “two pizzas.” If the team is still hungry after eating two pizzas, then the team is too big.

Rule No. 786: “A prize in every box.” — Cracker Jacks

Senturia is a serial entrepreneur who invests in startups. Please email ideas to [email protected].

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