First Entrepreneurial Experiences

Brian Zwerner
3 min readJul 26, 2021

This week I asked a group of founders about their first entrepreneurial experiences. I expected to get lots of stories of lemonade stands and such, and these founders did not disappoint. Almost all of the founders I spoke with on the topic related being entrepreneurial in middle school, generally around 12–14 years old. It was fun to hear their responses, and I think it says something about these people that they started early trying to figure out how to solve a problem and make a few bucks.

The majority of the founders shared stories of getting some type of products at a low cost (or free) and selling them to people willing to pay a higher price. My own middle school experience was bringing in the items to make bagels and cream cheese and to sell to my classmates. We bought bagels in bulk, got big containers of cream cheese, and the knives and napkins. I remember there being some portion of the sales going to some school club or activity, and a portion of the profits our crew was allowed to keep.

Andre Fluellen, my partner at Beyond The Game Network, had a similar experience. He bought candy in bulk and was selling it to his middle school classmates. However, he didn’t partner with a teacher, and he says he got “detention because the principal caught me pushing candy”. Darrel Frater of TheClub followed Andre’s lead. He said he and his older brother bought “cans of soda for about $0.40 before the bus came and sold them to students at school for $1”. The enterprising siblings eventually expanded their offering to candy and chips bought in bulk at Costco. They made enough money to buy their first Xbox, and they never got caught by the administration.

Evan Kirkham of Colorcast was one of the founders I spoke to that started young but filled a need outside the schoolyard. He described “sneaking onto the local golf course, collecting lost golf balls from the high grass, washing and repacking them, and reselling them in front of the clubhouse”. Young Evan didn’t have to watch out for teachers in his entrepreneurial endeavor, just the golf course manager.

Only one founder I spoke to had worked an actual paid job. When he was younger, he worked a paper route and then as a teen he worked in construction. I’m guessing if I spoke to a larger group of founders, these types of jobs would have been mentioned more often. Maybe I would have found a few people who mowed lawns, shoveled snow, or babysat neighborhood kids.

Either way, I saw a strong correlation between the entrepreneurial spirit and youthful efforts at the same. Not a big enough study to be statistically significant, but I’m guessing these results would hold with a large sample size. The drive to build something usually seems to manifest in the early teen years. If you’re a startup founder today, hopefully you can remember these early experiences that helped shape your approach to business.

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Brian Zwerner

Writing about Crypto and web3 for business executives