Manny Padda is an entrepreneur, angel investor and philanthropist who won the 2016 Canadian Angel of the Year Award. As an EO Vancouver member, he was the 2017 Entrepreneurs’ Organization Global Citizen of the Year Award. In this article, Manny shares his strategy for a smooth business exit plan. A version of this article appeared in Fast Company.

I’m not sure when I first knew the startup I invested in last year was doomed. Maybe it was when they stopped fundraising efforts a month out from their goal, overly confident that one big investor was going to come through in the clutch. Maybe it was when they came to me for more money when that didn’t work out. Or maybe it was because the founder left to go start a second company before the sale was complete. Whatever the final straw was, no one was surprised to see the company eventually declare bankruptcy.

Needless to say, this was not one of my more successful investments. I mention all this to prove that even with 23 exits under my belt—some as an entrepreneur, some as an investor—it’s never an exact science. For the last decade, I’ve invested and advised in everything from tech to sports, earning accolades as Canada’s Angel Investor of the Year in the process. Along the way, I’ve learned that a “successful exit” for a startup—that critical moment when the founding team and investors decide to get a return out of the business—will be different for everyone.

While there’s lots of advice out there on how investors can exit successfully, there’s less for entrepreneurs in the trenches. That’s a shame because how you exit as a first-time entrepreneur is going to define your career going forward, proving to onlookers that you can deliver (or, in a worst-case scenario, that you’re a flake). Having seen both frustrating losses and plenty of coveted 10-baggers (industry speak for 10-times return on investment), I’d like to pass on a few key factors that can make for smoother exits for new entrepreneurs. (more…)