Over his career, Daniel Debow has found himself through a combination of luck and skill in interesting situations with some high and mighty people. When he was a student at Stanford University, he met venture capitalist Peter Thiel, the early Facebook backer. Later on, Daniel would go on to found his own startup, which he sold to Tobi Lütke’s Shopify. And as someone who is comfortable with both corporate law and technology, he rubs shoulders with Galen Weston on the board of the Loblaw Companies. Daniel Debow may yet become a billionaire himself: he is both a serial entrepreneur and a prolific angel investor in startups, with many notable wins to date. Earlier this year, he left his VP job at Shopify, tweeting “I’m an entrepreneur. Time to do new, hard things.”
Raising money is a hard slog and Daniel Debow has been on both ends of the table. Angel investors are often bored wealthy people who like to lord over their professed “expertise.” A lot of business success can be explained by narrow specialization and some degree of luck. Daniel Debow is much more self-aware about this - and has some claim to be an all-around superstar from the earliest stages. While completing the combined JD/MBA program at the University of Toronto, he had internships at prestigious investment bank Goldman Sachs and Sullivan & Cromwell, the Goldman Sachs of law. And he achieved the highest GPA in the combined program. But upon graduation, he chose a less conventional path by joining fledgling startup Workbrain, where he was a "General Purpose Smart Guy." His rationale was simply that it seemed more fun.