How Do You Know If Someone’s Ready to Be an Entrepreneur?

 Sean asked a great question recently:

"How can I tell if someone’s truly ready for the challenges of owning a business?" https://youtu.be/tJuCAlwidRE 

If you work with aspiring entrepreneurs whether they’re thinking about starting or buying a business this is one of the most important things to figure out early on. The hard truth is: not everyone is cut out for entrepreneurship, and diving in unprepared can lead to costly mistakes.

When I was a business broker, I saw this all the time. People would come to me with the dream of buying a business often leaving behind secure jobs with pensions and perks without fully grasping what they were walking into.

So how do you test their readiness?

Here are two simple but powerful filters I’ve used over the years to separate dreamers from doers:

1. The “Late-Night Credit Card Terror” Test 😱

Running a small business isn’t always glamorous. Sometimes, it's 3:30 a.m. and you’re lying awake trying to figure out how to make payroll because a client payment fell through and rent just cleared your account.

This happened to me. I realized at that moment that my only option was to take a cash advance on my personal credit card to pay my receptionist.

It felt awful — but it worked. That’s the gritty reality of small business ownership. It’s not just about vision boards and product launches. It’s about resilience, resourcefulness, and doing what it takes.

I now ask aspiring business owners:

“Have you ever had to take a cash advance to cover payroll?”

You’d be surprised how many seasoned owners nod their heads. If someone can’t even imagine that scenario or is clearly horrified by it it may be a sign they’re not mentally prepared.

2. Can They Sell? 

Sales is the oxygen of a business. No matter what kind of company you run, if the sales don’t happen, the business doesn’t survive.

Even if you hire salespeople, you are still the chief salesperson as the owner. That’s why I always ask:

“Have you ever worked in a commission-only sales role?”

If they say yes, great. They’ve already had to survive on performance. They know the pressure of “eat what you kill.” They’ve learned how to handle rejection, stay composed, and deliver value without coming off as desperate (what I call “commission breath”).

If they say no? That’s a yellow flag.

I often recommend:

• Try door-to-door fundraising for a nonprofit
  
  

• Do cold calls for a charity or community cause
  
  

• Practice telemarketing for something meaningful
  
  

The idea is to test their comfort with selling, especially when there’s no safety net. If they won’t try it even when their job and mortgage are safe, how will they perform when their livelihood is on the line?

Bottom Line

Entrepreneurship isn’t just about skills, it's about mindset, stress tolerance, and grit. Before someone takes the leap, they need to understand the true nature of the journey ahead.

✅ Are they ready to make tough calls in tough times?
✅ Can they sell without fear or desperation?
✅ Do they know what it’s like to live without a safety net?

If the answer is yes, they might just be ready.
If not better to find out now than 6 months (and $60,000) too late.

Got more questions like Sean’s? Keep them coming.
And if you’re looking to dig deeper into buying or selling a business, check out the free resources and videos at DavidCBarnett.com.

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