How a 1990s eBay Side Hustle Sparked a Million-Dollar Flipping Empire You’ve Never Heard Of

Growing up in Milford, Massachusetts in the 1990s, Nick Bruni attended local coin shows with his father. Occasionally, Bruni would help his dad sell the collectibles online, back in the early days of eBay — listing items and packing orders. 

“ I was never hugely passionate about coins,” Bruni, 34, tells Entrepreneur. “But I liked the idea of being your own boss and selling your own stuff to make a living.” 

In high school, Bruni was cleaning out his room one day when he stumbled upon his Pokémon collection from the 1990s. He wondered what the cards were worth and asked his dad to help him list them on eBay to find out. They organized the cards, took pictures and put together the offering. 

I fell in love with the eBay process.

“ I fell in love with the eBay process,” Bruni recalls. “I would come home from school every day checking the view count, the number of watchers, what the bid was at and answer any questions. Seven days later, when the auction ended, we shipped the order out, and I was hooked on selling something.” 

After Bruni sold his first Pokémon collection online, he reinvested the earnings into another Pokémon collection, which he broke apart to sell as individual cards. 

For years, through high school and college, Bruni continued flipping Pokémon collectibles on eBay as a part-time hobby. 

From part-time hobby to full-time eBay resale business

When Bruni graduated from college in 2016, he began to take his online sales more seriously. Bruni was working in the Merchant Marine on a cargo ship, which meant three to four months on, followed by three to four months off. 

“ So that’s when I would focus on the eBay business,” Bruni explains. “I needed something to occupy my time, and I also really enjoyed Pokémon, so it was definitely a passion project and a secondary source of income.”

About five years later, at the beginning of 2021, Bruni decided to focus on flipping collectibles full-time — and his business, Old Skool Pokemon, has seen steady growth since. In 2022, Bruni pulled in $660,000 in annual sales. 

By October 2023, the business had taken off to such an extent that Bruni hired his first remote employee to keep up with demand. That year, annual sales surpassed $1 million, then increased to about $1.3 million the following year. 

Old Skool Pokemon achieved over $2 million in annual sales by 2025. What’s more, the business has already generated $1.5 million in 2026, so Bruni is eyeing the $3 million milestone this year. 

High-volume selling in a competitive collectibles market

Pokémon collectibles remain the business’s bread and butter. Bruni sells vintage collections going back to the 1990s and current sets released today, typically as single cards. 

The business relies on a significant volume of sales, with margins at about 15%, Bruni says. 

“Last year, when we did $2 million in sales, we sold 96,000 items,” he adds. “Average sale price $21. So it’s never a really high-value card, making a lot of money off one single item.”

Bruni sources his products from wholesale distributors Mad Al and Southern Hobby. He notes that as Pokémon has enjoyed a “massive resurgence” in recent years, getting his hands on the newest sets can be difficult. 

“A couple years ago, you could buy collections all day at 65%, 70%,” Bruni says. “Nowadays, you’re having to pay 80%, 85%. So you’re working on razor-thin margins and having to make up for that in the volume that you’re selling.” 

Pokémon only works with eight distributors in the U.S., and demand has increased to the point that those distributors primarily accept new applications from sellers who have brick-and-mortar stores, Bruni notes. 

Live streaming unlocks a new level of scale, first hire

One of the biggest recent changes — and boon for business — is Bruni’s commitment to live streaming, which allows him to open and sell packs to his audience in real time. 

“When eBay announced it was going to introduce a live streaming aspect [in June 2022], I knew I wanted to get on there,” Bruni says. “I liked the idea and knew that it could be a really big thing.” 

Bruni’s initial assessment has proven correct. Live streaming ramped the business up considerably in 2023, requiring that first hire, a fellow seller (KetchumAllCollectibles) in Chicago whom Bruni had met through the Pokémon community. The duo also co-hosts the PokeFlipz podcast on YouTube.

Soon after, Bruni relocated from Massachusetts to Chicago to be closer to his friend, then brought on a second employee to help manage the fast-growing business and make it possible to live stream every day. 

“It was tough to bring on additional help,” Bruni admits. “My business is my baby. I would have to give up some control. But hiring employees to help you scale your business is very beneficial. I’m at the point now where I would not be able to handle everything that’s going on by myself.” 

Nowadays, Bruni estimates that he spends about 10 hours a day working on the business, seven days a week, with the occasional days off. That includes live streaming seven nights a week; a stream can last anywhere from three to eight hours. 

“ It’s a tremendous amount of work, but it’s also a huge passion of mine,” Bruni says. “So it’s both my job and something that I really, really enjoy doing.” 

Expanding into physical retail and what comes next

Now, Bruni is preparing for an exciting next chapter for the business: opening his first brick-and-mortar store. He’s currently deciding between a few places in the Chicago area and hopes to open in September. 

However, a physical storefront doesn’t mean Bruni has any plans to leave eBay — in fact, he sees the expansion into brick-and-mortar as an opportunity to integrate in-person sales and virtual flips.

Opening the physical store will allow Bruni to purchase Pokémon products from people who stop by and provide an ideal live streaming set-up for his online customers. 

“I can be walking around the shop, showing people in the stream, ‘Hey, this is what we have available today. What do you guys want to bid on?’” Bruni says. “It will give a virtual card shop experience to the internet, the people that come into my streams.”

Growing up in Milford, Massachusetts in the 1990s, Nick Bruni attended local coin shows with his father. Occasionally, Bruni would help his dad sell the collectibles online, back in the early days of eBay — listing items and packing orders. 

“ I was never hugely passionate about coins,” Bruni, 34, tells Entrepreneur. “But I liked the idea of being your own boss and selling your own stuff to make a living.” 

In high school, Bruni was cleaning out his room one day when he stumbled upon his Pokémon collection from the 1990s. He wondered what the cards were worth and asked his dad to help him list them on eBay to find out. They organized the cards, took pictures and put together the offering.