You gotta know when to fold ‘em

Caleb Simpson
2 min readSep 29, 2021

When to quit your business

Photo by Chris Liverani on Unsplash

There is one thing the entrepreneurial world doesn’t talk about enough. That is knowing when to QUIT.

There is no shortage of clever memes about perseverance and never giving up, but sometimes it’s just time to quit! Seriously.

If you’re over 40 you have probably heard the old Kenny Rogers Song, The Gambler.

“You’ve got to know when to hold ‘em

Know when to fold ‘em

Know when to walk away

And know when to run”

There is a lot of wisdom in these words.

To simply “inspire” entrepreneurs to never give up at all costs is just flat out dangerous.

Sometimes your idea actually sucks.

Other times you risk going into debt up to your eyeballs in order to keep the ship sailing.

Yes, there are times to persevere, but you should also consider when it’s time to fold ’em and walk away.

I faced this extremely tough decision with my first business.

The short version of the story is that we were growing. Growing so much we couldn’t afford to keep the lights on.

We had taken on so much debt in the name of “perseverance” that we hit a point we couldn’t stomach anymore.

That, coupled with business partner disagreements lead us to “close the doors.”

Thankfully for us though we had somebody interested in buying the company off our hands for pennies on the dollar.

Even if we hadn’t had a suitor our business had reached its peak. It was time to walk away. Or RUN rather.

Maybe you can relate. Perhaps you are in a position right now where you feel like it’s time to throw in the towel but everybody on Instagram is telling you, don’t stop, never give up.

Just know this. It’s okay to quit. Your business doesn’t define you, and there will always be other amazing opportunities.

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Caleb Simpson

Sr. Customer Success Manager at Klaviyo. Entrepreneur, and founder of Bearded Brothers. Outdor lover. Father, &husband of 3 kids. I love helping others succeed!