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- A short note on looking like hell
Hey folks,
Short one today.
A little while ago, a friend told me unprompted, “Man, you look like hell.”
That’s how you know you’re in deep.
So: a note on the wear and tear that comes with entrepreneurship.
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A little while ago, I’m on a Zoom call with several people, including a friend who is a fellow holdco operator.
As we’re wrapping up the call, my friend asks me to hang back for a minute. And that’s when he tells me I look like hell.
He’d noticed what I hadn’t recognized in the mirror: I looked beaten down. Skin tone off. Tired. Worn out.
It wasn’t a zinger. It was coming from a place of love. As another guy who operates multiple businesses, he knows how stressful the game can be. And I was grateful he said something, even if it stung a little in the moment.
Turns out, he was going through his own version of hell. Game recognizes game, I guess. (Though I hadn’t noticed. Maybe he’s a better friend than I am!)
Another time, I did notice a founder friend looking rough. I told him, “I don’t know how to help, but I’m pulling for you.”
His response: “We’re entrepreneurs. This is what we signed up for.”
It hit hard because he’s right.
—
The obvious caveat here is that these are first-world problems.
My buddy had been through the wringer, but he still has a family that loves him, he still has his health, he’s still solvent. These are all made-up problems compared to what some people in the world are going through.
But the stress is real. And it’s not just the business stuff. As you get older, the layers stack up—family, work, community, promises made. You carry all that. And it shows.
—
When people ask me if they should be an entrepreneur, I tell them this:
Don’t think of it as a career. It’s a lifestyle choice. You’re choosing a life where your capital is at risk, where you carry the stress, where even your skin starts to show the wear.
There’s nothing wrong with taking a W2 job. There’s also nothing wrong with this path. But you’ve got to know what you're choosing.
And if you decide to be an entrepreneur, I think there’s a mandate for each and every one of us to have empathy for everybody going through it. No two businesses are the same, but the ups and downs are universal.
So look out for your fellow builders!
3 things from this week
Appetizer: I’ve always dreamt of owning a bank. But why is this tiny one listed like a used car?
Main: I love when my friends dive into crazy projects. My friend Sieva just spent $23M on a 73-year-old hotel in Montauk. Here’s his deep dive. It’s a great read.
Dessert: One of my YouTube videos is blowing up right now (relatively speaking). It’s about why the Vegas Sphere is losing money. Turns out pronouncing “Nevada” like a Texan gets a lot of people mad!
That’s it for today.
If you’ve got a story on this, hit reply and send it my way!
Thanks for reading,
Michael
P.S. Don’t forget to RSVP for next Wednesday! If you’re considering buying a business, it’s worth your while to get smart about financing.
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