What Are The 6 Reasons You Shouldn’t Be An Entrepreneur?

“Hi Brett, it’s Steve. I know it’s been a while since we spoke, but I’d love to catch up with you to bring you up to speed on what we’re doing.” Then the voice message ended.

“Well, Steve is persistent,” I said to myself, shaking my head. Steve was an entrepreneur I’d been introduced to over ten years ago.

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He’s been trying to get his startup off the ground, burning whatever is left of his savings, now for ten years. Ten years with no real success. Ouch.

I was dreading the phone call with Steve because I knew his company was going nowhere. And I felt bad for him because who I was I to tell him to stop?

But the reality is Steve should have never gotten started because Steve violated the first reason why you shouldn’t become an entrepreneur:

Reason Number One: You need more than persistence to be a successful entrepreneur.

You’ve likely read the story of the entrepreneur that was down to his last dollar. Then, seemingly out of nowhere, good fortune set in and the entrepreneur became unbelievably successful. The stories are true, but you never hear the story of the hundred other entrepreneurs that failed who were just as persistent.

Steve is one of the entrepreneurs that is going to fail, but he doesn’t know it yet. In fact, Steve will likely never realize that he is doomed to failure.

Yes, you do need persistence and grit to succeed, but those are just the entry fees for being a successful entrepreneur.

Reason Number Two: You shouldn’t become an entrepreneur if you can’t recruit a great team.

You can skip to rule number three if you’re a solopreneur. If you can’t recruit a great team around you, then the odds of your success go way, way down.

I have met some successful entrepreneurs that have built successful companies without having great teams around them. However, they are the exceptions, not the rule.

And even though these entrepreneurs have built successful companies, they eventually reach their limits without being able to recruit a great team. You can’t do everything yourself, so you can’t grow without a great team.

Reason Number Three: You shouldn’t become an entrepreneur if you can’t stay focused.

There’s someone I worked with years ago named, “Doogie.” Doogie was very smart, and Doogie was very creative. And Doogie wanted oh so much to be an entrepreneur.

But Doogie, for the life of him, just couldn’t stay focused on one thing. Doogie was, being nice about it, flighty.

So Doogie would start working on an idea for a few months. He’d be all in. Then, just as quickly, Doogie would lose interest and quit the venture.

Reason Number Four: You shouldn’t become an entrepreneur if you are afraid to sell.

I’ve worked with some unbelievably geeky engineers turned CEOs that you would never expect to be successful selling, yet they are very successful. And I’ve seen other geeky engineers that are too afraid to just get out there and sell.

You will always be the most successful sales person your company has because no one can replace your passion and knowledge of your company. That’s why it makes me so sad to see someone stop themselves before they get started.

It’s okay to be scared to sell. But you’ve got to overcome your fear and just get out there. Your confidence will build over time.

Reason Number Five: You shouldn’t become an entrepreneur if you can’t be a clear thinker.

It’s going to be very hard for you to succeed if you can’t clearly and quickly explain your company to others. There’s that new engineer you want to recruit. There’s the investor you need to convince to back you. There’s your existing team that you need to stick around.

Good luck convincing any of them if you can’t communicate with them effectively. Seriously, good luck because you’re not going to get very far if you can’t explain your business to others.

Reason Number Six: See Reason Number One.

“Brett, we’re getting really close to breaking through,” Steve said to me when I called him back. I cringed and felt sad for him.

Survivorship bias is real. Steve’s going to be chasing his dream until he dies or runs out of money. The ability to know when to give up on your dream is really, really hard. Believe me, I know this too well.

The best advice I can give you is just be intellectually honest with yourself. If you look at this list and realize that you are guilty of some the above rules, then maybe it’s time to move on.

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I work with startup CEOs to help them grow their businesses . I built several businesses from $0 to >$100M. Learn more at

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