When to Exit the Business 🚪

Author

Damon Brown
May 30, 2025

In partnership with

This edition is also brought to you by the Decision Lab newsletter, the newsletter for ambitious founders 

Hi reader,

You know that one group that shouldn’t have done that last album?

Or the awesome series that would’ve ended perfectly - on its second to last book?

We all have our favorite moments spoiled because they were stretched.

The elements lingered too long.

Overextended.

Sometimes, it goes past its natural expiration date because of money.

“Hey, we’ll double your advance if you bring the characters back one more time!”

Sometimes, it is because of audience demand.

“We want them to last forever!”

And sometimes, it is because we as artists can’t face that the moment is done ⌛️

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I remember the moment when I looked at one of my co-founders in the eye and, almost in unison, we said it was time to wrap it up.

We sold our popular app Cuddlr later that year.

Checks hit our bank accounts.

We went separate ways.

As I share in The Bite-Sized Entrepreneur, selling ended up being more of an existential crisis than I could imagine.

The trifecta of being a new husband, a new father, and a new entrepreneur felt like my version of balance.

Now, I needed to find another piece of my identity.

But that didn’t mean it wasn’t time to sell 👏🏾

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The question isn’t if you should keep doing what you’re currently doing.

The question is if there is another reality calling you.

A better way to show up in the world.

A stronger path to serve.

Sometimes, we’re so busy defending what we believe is our identity

That we don’t recognize the increasing tightness of the armor.

Or that the reason we started isn’t there anymore.

Or that the objective has changed.

In our case, when we were on the cover of the Wall Street Journal 

We knew that we made our impact on culture.

And it was time to wrap it up.

But unlike a battlefield, there is no general telling you when to leave.

Only you can know when it is time to head back.

As the confused can mistake giving up because the battle is lost

With letting go now because the battle is already won 🏆

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Every Wednesday in May BringYourWorth.tv Live is helping you get your business off the ground:

Click on any of the videos and hit the Notification button to get a message when we are live and ready for your questions and feedback.

Miss the previous videos? You can watch them right now!

Time to exit your business?

On BringYourWorth.tv, we talk about selling your business, the different pathways to success, and when to know it is time.

Bring your questions, feedback, and retirement plan 👴🏾

Wednesday, May 28th

1:11 pm PT

👉🏾 Join us

Knowing when to leave is as important as knowing when to stay 💨

🙋🏾 I’m Damon! (http://www.damonbrown.net) I help side hustlers, solopreneurs & others like yourself bloom. As a bestselling author, 2x startup founder & 4x TEDTalker, I co-founded the popular connection app Cuddlr and led it to acquisition within a year while being a stay at home dad with my infant son.

🫱🏼‍🫲🏿 Today, my boutique coaching business Bring Your Worth supports hundreds through one-on-one virtual and in-person support, as well as behind-the-scenes services for TED, HEROIC, and other impactful organizations. You can catch this free weekly newsletter as well as the 18,000-subscriber strong television show BringYourWorth.tv.

🚀 Think coaching could help you get to the next level? Reach out and let’s chat.

📚 You can also grab my 27th book, The Complete Bring Your Worth Collection, everywhere books are read, heard, and sold.

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