The Paperclip Hustle
How Creativity, Grit, and Bold Asks Unlock Real-World Lessons
Every semester, my favorite class activity is the Bigger, Better Challenge. I split my students into pairs and give each team one item: a paperclip. Their mission? Trade up for something bigger, better, and more valuable (in my opinion). The constraints? They have 20 minutes. And a few rules:
No trading with the same person twice.
No trading money (including foreign currency).
No using personal belongings.
Stay inside the McCombs building. Don’t disrupt any classes
There’s a small incentive—bonus points and the power to choose the team order of final presentations. Just enough juice to make them go for it.
I encourage them to be bold, creative, and scrappy. As long as they follow the rules, anything goes.
The exercise is inspired by the story in One Red Paperclip, where the author traded a single paperclip all the way up to a house.
And while my students don’t walk away with real estate, I’m always blown away by what they do bring back: iPads. MacBooks. Meta Ray-Ban smart glasses. Bluetooth speakers. Yeti tumblers. Even vintage typewriters.
But the real magic is in the lessons that emerge—every single time.
Don’t Oversaturate the Market
The first stop for most teams? The student atrium. It’s full of classmates eating, studying, and working on group projects.
It also becomes a crowded marketplace—fast.
Eventually, students get peppered with the same pitch over and over, and the value of each subsequent trade goes down.
The savviest teams? They skip the obvious and head to faculty offices, administrators, or even staff lounges. That’s where the real treasures hide.
The Lesson: Don’t chase the same market as everyone else. Look for overlooked niches. A smaller audience, in the right offer, can yield much bigger results.
Just Ask
One thing that always surprises my students?
How willing strangers are to help when they’re simply asked. I have another challenge earlier in the semester where students can get bonus points for asking for a discount for a cup of coffee. The worst that can happen is they say no. Best case, you get the discount. But the fear of rejection is typically stronger and holds us back from asking in the first place. This challenge is like the coffee challenge on steroids.
High-achieving students are often uncomfortable asking for help. They assume they have to do it all themselves.
But when you get out of your comfort zone and show a little vulnerability, people lean in. Everyone loves an underdog story.
And guess what? Your customers are people too. If they understand your mission—and your struggle—they’ll be more likely to support you early on.
The Lesson: Don’t hide your story. Share it. Ask boldly. Help will come.
Beg, Borrow, Be Resourceful (but don’t steal)
Many of the high-value trades aren’t permanent gifts—they’re borrowed. And that’s fair game.
There’s no rule against borrowing something impressive to boost your next trade. And in entrepreneurship, this is survival.
You won’t always have the capital to buy what you need. So borrow. Barter. Get creative.
The Lesson: Constraints fuel innovation. If you had money to throw at every problem, you’d miss the most efficient, elegant solutions.
Hustle Wins
This activity leads directly to my favorite end-of-semester challenge.
I can lecture all day, but unless students try things for themselves, they’ll never truly build their skills. Experience beats theory. Always. Most skill sets are developed from 10% education, 20% exposure, and 70% from experience.
So here’s the final challenge:
If you can hustle like that for 20 minutes…. What could you do in 30 days?
Each student starts with $25 of seed capital. Groups of four combine to start with $100.
The mission? Start a LEGAL business and try to 10x your money in one month. Generate at least $1,000 in revenue.
Write a one-page reflection on what you built, how you made money, and which class concepts you used.
Even if you don’t hit the goal, you’ll learn more from failing at this challenge than you will from most classroom wins.
The Lesson: Just start. Don’t wait for the perfect idea or timing. Momentum matters more than mastery.
Dollars From Dorm Rooms
There are countless businesses students can start:
Tutoring
Cleaning services
Baking
Photography
Pet care
Social media consulting
The idea isn’t to build the next unicorn—it’s to start something. Michael Dell built computers in his dorm room. Tiff’s Treats was founded right here on campus.
So why not you? This first taste of success, even $1,000 and spark enough motivation to keep going.
This is always my favorite activity of the semester because it starts with something seamingly impossible and ends with real-world insight.
Now if I can just figure out how to make Pro Formas this exciting…
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