Should you buy a boring business?


Guess what's sexy these days?

Cargo pants.

Chunky sneakers.

And buying boring businesses.

Yup. Folks are ditching their fancy Wall Street and FANG careers to buy... wait for it...

Laundromats, pest control services and plastic bag manufacturers.

This week on The Examined Life Podcast, we’re joined by former hedge fund investor and small business owner Ben Jasper.

We ask the question:

Should you buy an unsexy business?

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My top 3 takeaways


Unsexy businesses will continue to thrive

Software is eating the world. AI is taking jobs. What isn’t getting offshored is getting "near shored." Except hyperlocal service businesses. And the best part? They have tons of upside.

Watch the clip

Small businesses don’t come with user manuals

When you start a new job, there’s usually an onboarding process full of training sessions and presentations (and hopefully free lunches). But not when you buy an unsexy business. Instead, you learn through printed emails and an a good old calculator.

Watch the clip

Money ain’t everything

We often think that the next promotion or a new car will solve our existential angst. It’s the classic when-then trap. But as Biggie said, Mo Money Mo problems. The good news? A rich life can be yours without being financially rich.

Watch the clip


My favorite quote: Hard things are not created equal

Literally, I've never faced these issues in my entire life, and I'm facing them for the first time in my 40 years. That's scary as hell. So that's hard, but you just have to be okay with doing hard things. Unlike hedge funds, where if your book's not working, you could lose pretty much your entire year P&L in a couple of weeks. But the good news about SMB, typically with time and a little bit of money, a problem will resolve itself. You're not getting fired.

Why this episode matters to me

Be careful what you wish for.

The hedge fund grind at a prestigious firm like Citadel is a total grind.

You don't own your time. Stress is through the roof. And you can't take a true vacation.

But is owning a small business better?

Yes, there's tons of leverage and the compounding of your equity can create real wealth.

But you own a plastic bag manufacturer.

(No shade intended to Ben.)

And you have all the head aches of manufacturing, lower-skilled labor and extreme sensitivity to the economy.

Is this a case of damned if you do, damned if you don't?

Or maybe it's just the challenge you've been waiting for.

If you want to dig deeper

What I wish people told me when I walked away from Wall Street. Workaholism has its (financial) rewards, but it also has its hidden costs. And sometimes the juice just ain’t always worth the squeeze.

Love letters from our fans

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Khe

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