How Jamie Alexander Went From Software to Creator of Clothing for Trans Girls
Many entrepreneurs will inform you that what they’re doing now shouldn’t be what they initially got down to do. Making main skilled adjustments—even mid- to late-career—can typically result in extra fulfilling and profitable outcomes. That’s what our collection The Pivot is all about. Each month, we communicate to founders, business leaders and entrepreneurs about how—and why—they modified course and located success in a wholly totally different business. Here, we communicate to Jamie Alexander, the founding father of Rubies, a line of form-fitting clothes for trans ladies.
Designing clothes for trans ladies might seem to be a far cry from creating pc software program, however for Toronto-based Jamie Alexander it couldn’t have been a extra pure transfer. His daughter, Ruby, socially transitioned at age 9 and Alexander discovered it tough to seek out attire for her actions like gymnastics and dance. At first, she wore saggy board shorts as a substitute of the standard leotards. But when Ruby started expressing curiosity in sporting the swimwear her mates had been sporting, Alexander realized they had been experiencing a worldwide drawback that he was uniquely poised to assist remedy.
“I looked at the solutions out there and lot of them were lacking,” he says. “They seemed to be designed for adults and sized down for kids. Some had a big pad in front, which my daughter said felt like a diaper. Others required tight compression. Often they came in garish colours and designs.”
In 2018, he launched Rubies, a group of snug, easy-to-wear form-fitting clothes for trans ladies, together with undergarments and bathing fits which can be accessible to be shipped around the globe.

A lifelong tech fanatic, Alexander started tinkering with computer systems when he was round 10 years outdated and ultimately enrolled on the University of Waterloo to review electrical engineering. He landed at IBM within the Nineties the place he pioneered nascent ecommerce merchandise for manufacturers like Victoria’s Secret and labored for the corporate’s consulting group on a revolving set of latest merchandise in quite a lot of industries like training, insurance coverage and finance.
“That gave me the skills to really quickly understand an area—I knew how to pull information from subject-matter experts and apply it,” he says. It’s a ability that got here in helpful when Alexander made the leap into clothes design, the place he constantly consults with an exterior roster of specialists that features R&D specialists and advertising and marketing professionals.
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Alexander left IBM in 2010 after being impressed by the potential of the iPod Touch to create apps associated to the intersection of artwork and music. He entered the start-up world the place he met with various levels of success by endeavours like creating an interactive music software and a receipt processing answer for giant banks. But after greater than 5 years within the notoriously cutthroat start-up world, he was prepared for an easier day-to-day life, one the place he might give attention to social enterprise with out the stress of managing a staff and the expectations of buyers.
When he was able to launch Rubies, Alexander used funds from a earlier start-up exit and took on a facet hustle as head of product for a drone firm. He additionally acquired funding from the National Research Council of Canada’s Industrial Research Assistance Program, which helps Canadian companies in growing their innovation capability and taking their concepts to market. He labored with garment engineer Olena Vivcharyuk, who he was paired with on the Fashion Zone, an interdisciplinary incubator primarily based out of Toronto Metropolitan University. He’s since been working with Cat Esiembre from Pigeons + Thread, the R&D accomplice for all of Rubies’ merchandise.
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Scaling Rubies meant hiring a third-party logistics firm to deal with choosing, packing and delivery, on the lookout for offshore suppliers that had been capable of uphold Rubies’ particular high quality requirements and creating a repeatable R&D course of. When Rubies grew to become worthwhile in March 2023, Alexander was capable of shift his focus completely to his firm.
Unlike your typical founder, whose objective is to chase exponential progress for an eventual payout, Alexander’s focus stays working Rubies as a very self-funded, mission-driven life-style business the place the objective of supporting trans kids is paramount.
To that finish, this summer time Rubies launched a Gender Journey AI Chatbot designed to assist dad and mom with trans or gender-creative children that’s accessible in all languages. “I have a mission to help as many families and trans people as I can and support myself,” he says. “If I can do both of those things, I’m good.”
