7 min 31 sec

College Bartender Turns Online Shopping Into Accidental Side Hustle

In the prehistoric age before easy online shopping, a bartender discovers a way to supplement the tips she lost during a recession by reselling clothing to her friends.
Lessons Old School Reselling Retail

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What It's About

An accidental reselling side hustle helps a college bartender improve her credit score and earn extra cash.

Business Model
Skills Required
Creativity & Business Savvy
Profit Potential

Words of Wisdom

Dana had a couple of strategies that she used to maximize her profits while still passing on the online savings to her coworkers. First, she would only purchase clearance items. And second, she made sure to sell to the people who reliably showed up to work and would make sure to get them their items at the beginning of their shift.

Fun Fact

Dana did zero advertising and put in minimal effort for this accidental hustle. She simply offered to buy things for people if she heard them talking about needing new shoes or new clothes. Other than that, she just let the excitement of showing up with a new box of clothes and shoes speak for itself.

Notes from Chris

Episode 89

In the early days of a new industry, trend, or phenomenon, there are a lot of inefficiencies that allow creative people to make money in a way that might not work years later. This is the normal pattern of technological evolution. Something works really well for a while, but then you have to find something new.

Today’s story probably isn't something you can replicate in the same way now, but the lesson has other applications. It's about a college bartender who turns online shopping for friends and co-workers into an unexpected reselling side hustle. This hustle helped to supplement the tips she lost during a recession.

Remember that online shopping is a lot more efficient and common today than it was 15 years ago. This side hustle worked because the market of people Dana was reselling to was “unbanked,” meaning that most of them didn’t have credit cards. That was her competitive advantage.

How can you learn from the past and apply this lesson to the present?


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

Chris Guillebeau
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Quote of the Day
"I definitely learned a lot about risk. At first I thought risk was a bad thing, and I avoided it as much as possible. Then I realized that I could take calculated risks and get incremental gains."
—Dana Massaro #SideHustleSchool

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Chris Guillebeau