The last time I saw Ryan Holmes in person was a lifetime ago.
It was September 2019, and we were on the main stage at Elevate Tech Fest talking about lessons in leadership from running large companies, making time for his newborn daughter, and whether or not he was planning to stay on as Hootsuite’s CEO, which was going through a rocky patch.
“League of Innovators is trying to solve this problem of how we identify and accelerate young entrepreneurs.”
At that time he told me there were “no imminent plans.” Fast forward two months later, and Holmes was no longer the CEO of the company he had founded 11 years prior.
Now, a lot has changed since then.
Holmes has two daughters now (whom you’ll hear a bit from on this podcast) and a new fund, LOI Venture, tied to his League of Innovators charity. LOI is focused on developing young entrepreneurs, and the fund is his and New Avenue Capital’s Manny Paddy’s bet that the kids are all right.
Holmes’ interest in youth entrepreneurship started at an early age, and we get into why on this podcast. But we also trace how much has changed since Holmes’ transition from hustling quarters, to head Hootsuite honcho, to institutional VC excited about Web3.
It’s as much a conversation about how much the Canadian tech ecosystem has changed, as it is how much he has. So let’s check in with Ryan Holmes on his next act.
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The BetaKit Podcast is hosted by Douglas Soltys & Rob Kenedi. Edited by Kattie Laur. Sponsored by the University of Toronto and Venture for Canada.