As a former technology reporter I’ve been in over my head more than once in trying to explain complicated subjects. I knew I had my work cut out for me recently when Wellesley’s Christos Papavassiliou, a rising senior at Buckingham Browne & Nichols School, asked if we’d be interested in learning about his sneaker bot flipping company, DemonIO, and the hypebeast industry.

Not one to back away from a challenge, I agreed. But where to even start?

How about with what the heck sneaker “bot flipping” and “hypebeast” are.

Papavassiliou explains that DemonIO “provides bot-flipping calls, so kind of like the stock market, but for sneaker bots.”

The bots are software that automate the checkout process when trying to buy a hot new pair of shoes.

“For example, it will try to add the shoe to your online shopping cart and then fill in all of your credit card and personal information,” the 17-year-old says. “Bot flipping calls are posts that I create telling users how much to buy a bot for, the reason why I think it will go up, and the price I think it will hit. This way people have a very clear understanding of why to invest in the bot.”

As for “hypebeast,” Papavassiliou says the term “has many different meanings, but in my mind I see it as anyone who has a joy for designer and hype items and buys and sells the items in order to make a profit.” The hypebeast industry is expanding into a multi-billion dollar one, he says.

OK, with all that out of the way, how did Papavassiliou get into this business 7 months ago, originally by himself and since then with a small staff?

He’s had an entrepreneurial spirit for about as long as he can remember. “When I was 12, I had come up with the idea and even sketched out a product I called SmartPark. It was a small circular device that would go under parking spaces in garages and connect to an LCD monitor. It would detect once a car went over and say how many spots were available. Obviously, we have something very similar nowadays, but not when I came up with the idea.”

The teen started reselling shoes about 2 years ago, initially trying to get hype shoes online without a bot. Once he earned enough money, he invested in his first bot (called Phantom). While the $800 bot he bought with a friend wasn’t very good, he says, it did get him invested in the whole process.

With DemonIO, Papavassiliou wanted to share his bot experiences with others and help them make money. The name DemonIO isn’t meant to sound evil. “One of the definitions of the word ‘Demon’ is ‘a person with great energy, drive, etc’ and I feel this really represents me,” he says.

Papavassiliou (AKA, “HyperVenomBoston” online) spends a couple of hours per day on the venture, and uses the Discord communications app to support it.

I asked about whether bot flipping is frowned upon in that those not skilled at it could be left out when it comes to snagging new merchandise. But Papavassiliou says if people have gripes, they probably should be directed at the shoe companies themselves. “The way these shoes are released by the company in the first place is not addressing the needs of the average person,” he says. “These products are primarily aiming at a specific clientele that is willing to pay a premium price in order to have something relatively unique. Bots are just taking advantage of the poor infrastructure and carelessness of the retailers. These big shoe companies like Nike and Adidas actually don’t care at all because there is a hype built around the shoe and will sell out. ”

DemonIO has 4,000-plus members on its Discord server, and 1,600-plus Twitter followers. Customers range from kids to adults trying to learn about the bot market, as well as the stock market and non-fungible tokens (NFTs).

“Overall, DemonIO is a modern version of a consulting company that tries to keep up with the needs and demands of customers in the twenty-first century,” Papavassiliou says.

As a high school senior this year, Papavassiliou will have his hands full getting ready for college. That means he’ll either find a co-owner to operate DemonIO with him or sell it entirely.

If he does get out of the business, Papavassiliou is sure to have a few keepsakes.

“I still collect sneakers,” he says. “I sell some for profit and others I keep for myself or my siblings.”