My Most Successful Side Hustle
From making money to following dreams, our team’s collective work history is full of memorable side hustles.
Oh, the sweet sweet side hustle.
Sometimes it’s a way to stay afloat. Other times, it’s a way to pursue your passion. Sometimes it’s simply something to do while you’re bored, and other times? You’re just trying to get your parents to buy you a pet.
Regardless, our pasts are full of them. From creative to innovative to lucrative, our team shares some of their most memorable past — and present — side hustles.
“I don’t really hustle. I tend to mosey, TBH. That said, my only side hustle is photography. Since the early 90s, through three or four different careers, I’ve shot photography. When I lived in New York, I fell in love with street photography and amassed a pretty good set of images. I carried my camera with me nearly every day on my commute, so I was always ready when the light was right. Things happen so fast when you slow down to look.
Anyway, the only place my images lived was on my website and a friend of mine said, ‘Dude, these are great. Find a reason to print them out!’ So, after thinking of different ways to do that, I decided to make a ’zine. I found an online newsprint service, designed the whole thing myself and had them printed. It’s called Grit St.”
— Eric Anderson, developer
“WOTW actually started as a way to fuel our other business. We thought long and hard about a website solution that really worked for folks who were starting a business, and also folks who had been around but needed a simple site. There wasn't much out there that was between DIY and hiring an agency to custom-build something special. Simply put: we capitalized on the market, ran with an idea, and stayed flexible, using feedback from clients to power our growth.”
— Mallory Ulaszek, co-founder/lead project manager
“When I was a kid, my cousins and my sister and I would print out birthday, anniversary and get-well cards from that super old-school computer program, Print Shop, color them in with our smelly markers, and go door-to-door around our Minneapolis neighborhood and sell them for 50 cents. I’m still surprised at how many people actually bought something that they could have printed up themselves. I guess our coloring technique was pretty next level.”
— Molly Each, marketing editor
“When my husband and I were newly married, we Airbnb-ed the spare bedroom in our apartment. Although not ideal, we covered our rent and then some, which helped us save to buy a house. Worth it!”
— Katie Stipanovich, operations manager
“Not as much a side hustle, but I did have to give a presentation in order for my parents to adopt a cat for the family. We ended up getting the cat , which feels like the equivalent to a promotion.”
— Alex Lucke, developer
"I remember a time when I sat in a room for three hours to get paid $120. It was a mock jury for a trial case that was coming up soon, and they paid people to sit in and make a decision on the case. While it wasn't the most successful side hustle, it sure was interesting — but I'm glad I'm not still doing that!"
— Justin Mabee, developer
“When I was in 3rd grade, I started a hustle selling rubber band bracelets to my peers during lunch. One of the kindergarteners at the school, Lucky, was in a tragic accident where he was backed over by a lawnmower and he ended up losing his leg. So we called them Lucky Bracelets and donated all of the proceeds to his family when he came back to school. It ended up being almost $250, and I'm still pretty impressed 8-year-old me made that much off of $2 bracelets.”
— Shelly Morse, developer
"I’ve always been amazed by marketing. The genius behind it (when done right), the impact of it (especially when not done right), and the influence it has. I knew working in that world was what I wanted. So when a previous employer asked if I could pull together a website for them with ZERO experience, my answer was, ‘Absolutely.’ I knew it would be tons of work and a lot of pressure, but if I could pull it off, I’d have a chance to hop in with the marketing team and get my career started. Good news: no one died in the process, the website is still being used, and I’ve been working in marketing ever since — still doing sites even, thanks to my side hustle!"
— Jeannine Gallagher, project manager
