"Blue babies" like Jacobson have holes in their hearts that prevent blood from flowing properly - the medical term for this disorder is methemoglobinemia. The poor circulation results in blue lips.
In Jacobson's case, his pulmonary valve needed to be replaced. So surgeons cut into his heart and gave him a new one when he was 3 years old. Doctors said the valve would last 10 to 15 years.
The heart defect didn't prevent Jacobson from doing many things, except contact sports. Instead of hockey, which many of his friends in Canada played, Jacobson opted for competitive gymnastics and acting. During the summers he was a camp counselor.
In 2008 he went to college just down the street from University of Waterloo, at a tiny business school called Wilfrid Laurier University.
There, he joined Alpha Epsilon Pi and met Garrett Gottlieb, another pledge. Jacobson would later become the president of their fraternity.
Gottlieb was a computer science major who was also a fitness buff. He built numerous tools that helped him customize workouts, including a website called "iPumpIt." It didn't get much traffic, but it did get the attention of Jacobson, who had been interested in startups as well as staying fit, with the latter interest largely influenced by his heart defect.
When Jacobson was 19, during his freshman year exams, he was told he needed another open-heart surgery. It took him a month to recover, but the experience drew him to projects like Gottlieb's. Jacobson had been working on a textbook-trading website with another friend that never launched.
The heart defect "never held me back much, but it did keep me focused on living a healthier lifestyle," Jacobson tells Business Insider. "I thought, 'Wouldn't it be really cool if tens or hundreds of people used a product that could help prevent health challenges in the future?' That was inspiring for me and that's what got me interested" in working with Gottlieb.
Jacobson messaged Gottlieb to see whether he could help build iPumpIt. The pair spent the next several hours discussing startup ideas.
Jacobson had interned with Unilever and Pepsi's marketing teams, and he felt confident he could handle the business side of the startup if Gottlieb focused on the coding. So they began marketing their fitness product to other students and building new versions of it based on the features people were using.
PumpUp
Gottlieb and Jacobson entered a Waterloo pitch contest and were awarded $25,000 without having to give up equity, which gave them a little runway to get off the ground. They later raised a $200,000 seed round to continue their work on PumpUp after Jacobson graduated (Gottlieb didn't complete his degree).
While few students used the initial fitness product, the founders noticed photos were the most popular feature. People enjoyed posting and viewing workout images, and they would occasionally email the pictures to themselves. This behavior led the founders to build a mobile app and the current version of PumpUp, which launched in May.
PumpUp is now a mobile "thinspiration" app. It's like a photo-heavy social network for fitness buffs, where users post workout selfies and progress pics, get fitness tips, and leave encouraging comments.
Since the relaunch, PumpUp has grown from 1 million installs to over 2 million registered users. More than 10,000 photos are uploaded to the app each day. Jacobson and Gottlieb also raised a $2 million round of financing from prominent venture capital firms like General Catalyst.
PumpUp now has nine employees, and its Toronto office is strategically located a few feet away from a gym (every employee gets a free membership).
"We're building a team and a culture and it's all new to us," Jacobson says. "We're first-time entrepreneurs. But it's been awesome. It's fun to rally around a healthy vision."
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