People ask us how we ended up making underwear for a living, expecting some kind of market-research origin story. The real answer is dumber than that.
Sarah and I had been kicking around business ideas for a while - nothing serious, just the kind of conversation two entrepreneurial people have when they both know they want to build something together eventually.
We knew we wanted it to be creative, tangible, a little fun, and personal in some way. Sarah's always loved sewing and fabric. So when we heard about a printing convention in Dallas - printing on all kinds of materials, fabric included - we booked the trip.
We got excited about one idea in particular: personalized fabric for quilters. Custom prints, custom patterns, that whole world. We dug into it for a while before realizing someone else already did it, and did it well. Back to the drawing board.
Then, a while later, we were in the car. I let one rip - the kind you can't really pretend didn't happen - and we both started laughing. And I said something like, "wouldn't it be funny if there was a joke about that on my underwear?"
We looked at each other. That was it. That was the idea.
We drove home that night and spent hours online looking at what existed in the world of custom underwear. And pretty much nothing did. So the plan became: find really good, well-made blank underwear, and print funny, personal stuff on it. Jokes, faces, whatever people wanted. Simple enough.
Except it wasn't simple, because the next part of the plan fell apart almost immediately. We started sourcing blank underwear to print on, and every single pair we found was bad. Cheap seams, bad fit, fabric that felt like sandpaper compared to what we knew was possible.
We weren't going to build a business on top of something we weren't proud of, just to get to the funny part faster.
So we made the decision that actually built this company, about six months into the whole thing, and it had nothing to do with jokes anymore: we'd make our own underwear. From scratch. Not buy-and-decorate. Manufacture.
That decision is the whole reason do+dare looks the way it does today. It's why we spent weeks driving around the GTA finding sewing shops and elastic suppliers instead of just placing a print order. It's why we sank close to six figures into equipment and spent two and a half years building our own robotics and our own ink chemistry just to get a print to bond properly to bamboo fabric - chemistry that, funnily enough, we don't use anymore.
It's why Sarah personally trimmed and inspected every pair by hand in the early years, building the quality standards her team still runs by today.
And here's the part that still makes me laugh a little: the joke underwear actually worked, for a while. People loved the novelty pairs at markets and trade shows - you could see them get it in person, feel the fabric, hear the story, laugh at the print.
But online, a funny print on underwear reads as novelty, and novelty reads as cheap, disposable, one-and-done. Our underwear was the opposite of that! It just couldn't convey the high quality, along with the funny, through a screen.
So a few years in, we made the second big decision: we sold off all the printing equipment. All of it. We stopped trying to be the funny underwear company and leaned all the way into being the well-made one - which, if we're honest, is what the joke was always secretly about.
Good underwear that doesn't take itself too seriously, made by two people who very much DO take the "made well" part seriously.
We still think about that car ride a lot. Not because the joke itself matters - I promise you, it's not that good a joke - but because it's a decent reminder that you don't need a five-year plan to start something real.
You need an idea that makes you laugh, and then the stubbornness to actually persevere through all the ups and downs. AND - most of all - the willingness to pivot as needed.
And speaking of pivot: we've got underwear in the works with a soft fabric band, for everyone who's been asking. Still months away, but we're super excited!
-Rob(+Sarah)