Successful founders have been mythologized in startup culture, but the reality of getting to a success is less glamorous, and much harder than it seems. Our guest today, Mike Silagadze, founder and now former CEO of TopHat, joins me to discuss his journey founding one of the largest EdTech companies, his decision to hand over the CEO role, and why he’s joining Ripple Ventures as a Venture Partner.

This is a fun, no-holds-barred look at what it takes to create a successful startup.

Mike’s Background:Mike founded Top Hat in 2009 with Mohsen Shahini who is now the Chief Academic Officer for the company. Noticing that the graduation rate for university students in North America is below fifty percent, Mike and Mohsen realized that there was a problem of student engagement in the classroom. Through Top Hat, Mike and his team have aimed to better the relationships between students and their instructors and make the university experience a positive one for all. Since its inception in 2009,the company has raised over $350 million dollars and Top Hat is on its way to being one of Canada’s next unicorns.

Prior to Top Hat, Mike was an early employee at Miovision Technologies in Waterloo, another great Canadian success story. Mike is a graduate of the University of Waterloo in Electrical Engineering. 

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In this episode:

03:37 Starting a business during the financial crisis of 2008

06:32 Raising his first capital and working with those early investors

09:39 The importance of storytelling and pitching in early startups

12:11 Would he invest in himself if he heard his original pitch

13:30 Finding product/market fit

19:35 Maintaining your dataroom in between raises

22:28 Benefits of having strong investors

23:45 The reasons to acquire a company when you’re a startup

31:04 Mike’s thoughts on investment bankers

34:13 Did he consider selling early

35:06 He he decided to join Ripple Ventures as Venture Partner

37:43 The biggest changes in the Canadian startup scene

39:06 Thoughts on remote-first versus in-person

41:33 The future of crypto and DeFi

Mike’s Book Recommendations:Antifragile: Things That Gain from Disorder by Nassim Taleb

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