Building your C Level Team

team-justice-leagueBack when I was a seed stage VC I was always amazed to meet founding teams where every one of them had a C level title. CEO, CTO, etc. Now the beauty of having your own company is that you can call yourself whatever you want. But when dealing with institutional investors its important to be open and self aware enough to judge whether you truly have a C level team in their eyes.

I’ve been part of many startups now as either an investor or management team member. But FreshBooks is the biggest so far (Shopify is bigger but was much smaller when I was involved). We are at the growth stage, well beyond startup. And what we need in terms of leadership and management differs very much from what my past companies have needed.

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Founder to CEO: Tobias Lutke, Shopify

For my second installment of the Founder to CEO series, I’m very pleased to share my conversations with Tobi from Shopify.

I have had the pleasure of working with Tobi and the Shopify team in the past. They are building a truly special, market-leading company. Tobi comes to Canada from Germany. Before co-founding Shopify, Tobi was active in many open source projects. The best known of which is the Ruby on Rails framework where Tobi served as a core team member.

As you will learn from this post, Tobi is probably the most brilliant high school dropout you will ever meet.

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Founder to CEO: Mike McDerment

Last week I wrote about the interviews and research I did on how founders become great CEOs. Given that I just joined his company, it’s only fitting that I kick off this series of posts with some thoughts from Mike McDerment, co-founder and CEO of FreshBooks.

Mike & FreshBooks don’t need much of an introduction – especially here in Canada. FreshBooks is the leading cloud accounting specialist for small business owners and one of Canada’s premier startups.

Each interview I did followed the same high level, open-ended questions (below). But as you can imagine, each founder took the discussion somewhere special and personal. So, what follows is not an interview transcript, but my notes on key elements, learnings and insights. Enjoy.

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From Founder to CEO

When I decided to become a VC in 2010 I had lots of reservations. After all most VC funds don’t succeed. The Canadian VC industry in particular has not historically delivered returns (though there are some great new funds backing great companies – so hopefully that’s changing). In any event, history reveals that my tenure as a VC was short-lived. Still, during my brief time there, I began working on an investment thesis that I still believe can result in superior VC returns.

Some VCs, such as Foundry Group are theme-driven. Union Square also focuses more or less on a singular theme – large networks of engaged users. Other VCs look at markets more broadly and try and predict where they’re headed. Others still look at underlying technologies and invest in those waiting for a market use case to emerge.

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