Hustlers and clowns

Hustlers and clowns are two types of business people I’ve found. Actually, they’re everywhere, not just business, but I’ll talk about them in a business context.


Hustlers do what it takes to do the job by learning and meeting people’s needs. I love working with hustlers, at least the type I mean. The student who sold an apple as a challenge for five dollars and made the buyer feel she was getting a discount in my post “How to make selling fun and effective” is a hustler. My friend offered him a job because when he told me what he was looking for in his start-up—to figure out how to sell the product, to learn about the market, to help develop the product, to prepare for growth, etc—I said, “You mean a hustler?” He said, “Exactly!”
The start-ups I’ve seen take off tend to have a hustler as a founder.
Many successful salespeople are hustlers, but not all hustlers work in sales, though they’re usually selling something, though for the hustlers I know sales doesn’t mean pawning off some junk. The hustlers I know want to leave people satisfied. The point is they work like crazy to make it happen.
I’m usually hustling on a few projects at any time.
Most of my big projects started with some hustling.
I hustled my way into business school: “I started at an Ivy League business school 23 days after deciding to apply. Here’s how.
Many of my coaching clients that were dissatisfied with some aspect of their lives learn with me to start hustling in some new area, which leads to new opportunities, passions, and so on.
Many of the colleagues who have become my friends became friends because they were hustlers. I sensed they cared so much about their work that working with them was personal—openly, genuinely, and authentically sharing important parts of their lives for mutual benefit.


Clowns talk big game but don’t deliver. They sound attractive to work with, but leave you empty. I’ve sadly worked with a few clowns. They sound like hustlers at the beginning. I tend to give people the benefit of the doubt at first, so I started working with them, giving some trust. Now some of them owe me money that I’ll probably never see. I’m sure you know the type.
Clowns are the opposite of genuine and authentic, though they’re often skilled at presenting themselves that way.
Related to the clown is the snake. A snake intends to harm you or win at your expense. The clown doesn’t even realize the harm they’re causing. You almost feel more respect for the snake since at least they’re honest with themselves, not oblivious, like a clown.
It’s a sad feeling when you start realizing someone is a clown. You realize the patterns and your opinion of them drops. “Oh man, I was working with a clown. I thought they were a serious person.”

Origins of hustlers and clowns

I don’t mean to imply that people are either hustlers or clowns or that anyone is purely one or the other. Most people are probably neither for most of their lives, but sometimes become one.
One person might get swept up by a passion they realize they’ll never let go of, realize what it takes to start it and bring it to success and become a hustler in that part of their life. It may infect the rest of their life and make them a hustler everywhere, but more likely in the rest of their life they’ll be a regular person.
What makes someone a clown is harder for me to understand. They just keep promising the stars and, when they don’t realize their goals, they move to the next thing. I think they lack compassion and empathy to see the damage they do to people who believe them because they develop more and more effective skills to fool and con them.
Eventually you learn how to unmask clowns—checking references, asking for genuine evidence of claims, and things like that. It sucks to have to do that since most people aren’t clowns, but that’s what clowns do to us. They waste our time and resources.

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