8 min 17 sec

Teacher Flips Sports Gear For $8,000/Month

A teacher uses his love for sports memorabilia to bridge the financial gap between his teaching contracts—then goes on to create a highly profitable business.
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What It's About

How a $500 investment turns into $8,000/month.

Business Model
Skills Required
Sourcing & Coordination
Profit Potential

Words of Wisdom

To anybody looking to start a similar venture, with their own $500 investment, Matt recommends choosing a topic you’re interested in and knowledgeable about and finding items which you feel an emotional connection towards. You also shouldn’t be worried about getting it right every time. Sometimes, you’ll buy items which don’t sell, and that’s just the nature of the business. But if you get it right even 50% of the time, you could be profitable!

Fun Fact

Babe Ruth memorabilia is no joke! The 1920 Yankees jersey is the earliest known jersey worn by The Great Bambino. The jersey was originally a part of the Babe Ruth Birthplace Museum in Baltimore but was bought at an auction by rare sports memorabilia mogul Joshua Leland Evans for a cool $4.145 million!

Notes from Chris

Episode 727
Matt Myers knew the coming months were going to be financially tight. His yearly contract as a PE teacher was coming to an end and he needed money to bridge the indefinite gap between school years.

Back when Matt was a child, his dad had made extra money for the family by buying and reselling items he’d pick up from estate and garage sales. So, naturally, Matt figured it would be the perfect way for him to make some money too.

Taking $500 from his savings account, he decided he would head out to a couple of thrift stores, buy some stuff, and try to sell whatever he found on eBay. If he was lucky, he could make some money. And, if it didn’t work, well ... nothing ventured, nothing gained, right? In the worst case scenario, he felt confident that he wouldn’t lose money.

To guide his purchasing decisions, Matt focused only on items he’d once owned or had a strong emotional connection to. If he’d bought it or wanted it, there was a good chance other people out there would have as well.

Matt picked up a few electrical items on his first outing, but he felt really drawn to any sports memorabilia he came across; jerseys, jackets, caps and cards and anything else with a sports motif on it just felt like a good buy. And, after visiting a few stores, Matt came home with around 75 small items for his $500 investment.

Over the course of the next few days, Matt took pictures of the items on his phone and uploaded them to eBay. He set his prices by looking at previously sold listings on eBay and choosing a competitive price based on what he’d personally paid for the item. Matt always set a “Buy Now” price, so people could purchase the item right away, but he also allowed eBay users to pitch a price with the “best offer” feature if they wanted to.

Over the course of the next two years, Matt was able to make enough money from flipping to bridge the gaps in his teaching contract and make a little extra money where it was needed. But, he still mostly saw it is as a hobby. He attended the occasional garage sale and thrift store, but nothing major. That is until he flipped an item which showed him the real potential of his business.

Since starting the business, Matt has made $62,000 from flipping items on eBay, and now averages around $8,000 a month in profit. He invests a lot of this back into the business to buy new items.

Looking to the future, Matt is creating a standalone Kevin's Clubhouse website and will spend the next year or so looking at how to optimize traffic to get more sales.



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

Yours in the revolution,


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Quote of the Day
"As long as you have your phone with you and a site or way to look up how much an item previously sold for, you're already ahead of the game."
—Matt Myers #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau