the $5 challenge that changed everything

February 12, 2025

What would you do if you had to turn $5 into $25 in 24 hours? No asking for handouts. No magic tricks. Just hustle.

That’s the challenge I gave to the Business Club at my kids’ school. I handed each student a crisp $5 bill and told them they had two options:

Take the challenge—use the money to create more money.

Turn $5 into $25 in 24 hours by any (legal) means necessary.

OR

Keep the $5—spend it however they wanted. Buy a snack. Treat a friend. Do something nice for someone else.

Some students jumped in. Others looked at me like I’d just asked them to build a rocket ship.

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And here’s where it gets interesting…

One student, Clay, went to the next level.

He spent $4 on a box of trash bags and went door to door in his neighborhood. A storm had hit recently, leaving yards covered in debris. He charged homeowners to clean up their yards.

By the end of the day? He had turned that $5 into $78.

A few years later, Clay asked me to write him a college recommendation letter.

Instead of a standard “he’s a great student” letter, I told the dean:

"If Clay could take $5 and turn it into $78 using creativity and hustle, imagine what he could do with a degree from your fine business school."

You know what? They almost covered his entire college tuition. That’s the power of taking action.

Here's the deal…

  • Most People Avoid Discomfort – Given the choice, 75% of students took the path of least resistance. They missed the chance to push themselves. No risk, no reward.
  • Pressure Sparks Creativity – The students who stepped up found ways to make money fast. Some sold bottled water at soccer games. Some flipped thrift store finds online. And Clay? He built a mini business in a day.
  • Confidence Comes From Action – The ones who tried? They walked away feeling powerful. They realized they could create money anytime, anywhere. The ones who didn’t? They just ate their $5.

Here are your action steps:

  1. Act like your back is against the wall—even when it’s not. Urgency fuels success.
  2. Look for unmet needs. The best money-making ideas solve problems.
  3. Comfort is the enemy of growth. Stretch yourself. You’ll surprise yourself.

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