The “lifestyle business” paradox

When I was in college, everyone wanted to be a banker or consultant.

Then everyone wanted to be a venture-backed founder.

But is the real cheat code building a lifestyle business?

A business without investors and board meetings — where you choose freedom above everything else.

This week on The Examined Life Podcast, we’re joined by founder, CEO and gardener extraordinaire Kevin Espiritu.

We ask the question:

How do you build a lifestyle business?

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My top 3 takeaways

Seeing the game is a cheat code

When you’re building a business, it’s easy to get caught up with the latest trend. But identifying all the levers and strategically pulling them is the path to faster and more sustainable growth.

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Learn how the universe works

The Pareto Principle. Leverage. First Principles. Mental models have been all the rage. But once you get past the veneer and start to understand them, you begin to see that they apply everywhere. And you start to understand how the world works. It’s like living in the matrix.

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You can’t know the counterfactuals

In entrepreneurship (and in life), we make hard choices. It’s natural to look back and wonder what other choices would have looked like. To feel the pang of regret. But every choice has its downsides. Making hard choices and living with them is part of the game.

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My favorite quote: How to grow your perspective at scale

You're spitting your perspective into the void of the internet. And then on the other side of it, these platforms are incentivized to put your value in front of the people who would find it most valuable. And then what happens from that? A relationship develops and there's some sort of exchange of value at some point in time. And so that's really what's happening. It's just a scaled way to relate to people and the best way to do it will reap the most.

Why this episode matters to me

Ever since I left Wall Street, I have put my lifestyle front and center.

Brick by brick, I’ve designed every element from first principles.

No meetings.

Barely using Slack.

Not optimizing for profit growth.

It’s been deliberate and deeply rewarding.

Now, don’t get me wrong — the grass is always greener.

I look at those who grind and envy their revenue growth, follower count and press accolades.

But once the comparison fades, I’m deeply satisfied (and proud) of the life and business we’ve built.

And I wouldn’t trade my lifestyle business for a damn thing.

If you want to dig deeper

Lifestyle businesses can be brutal too — like the time mine was punched in the face. And while it hasn’t always been easy to leave money on the table, I’m basking in the glow of being a Post-Achievement professional.

Love letters from our fans

"Damn this was really relatable. I love how honest you are about things."

Hope you enjoy the episode,


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