When Founders Leave

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They say that the co-founder relationship is like a marriage. Indeed, founders probably spend more of their waking hours together than with their spouses. So, it should come as no surprise, that just as many marriages fail, the same is true of founder relationships.

I have been part of many startups where one or more founders left (or was asked to leave). It was always disruptive when it was happening, but always better in the end.

The Founder Pre-Nup Continue reading When Founders Leave

Recharging the Batteries


My man Harley from Shopify perfectly summed up how I was feeling yesterday: completely pumped to be getting back to work.

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I’m not sure I have any revolutionary new insights to share in this post. But having taken almost 2 weeks off, I remember what it’s like to truly recharge the batteries.

I don’t believe in work/ life balance. The best possible situation is to fluidly go in and out of “work” and other things. But if you’re doing what you love it’s never actually “work”. Continue reading Recharging the Batteries

What should I stop doing?


I was on an advisory board call recently when fellow board member Mike Serbinis of League and Kobo fame (among others…) asked a zinger of a question to the management team. When talking about all the projects the team had on the go, Mike asked which projects and activities should be killed?

This simple question is one that companies, teams and even individuals should be asking regularly. It’s so easy to start things. And in our always hustling go-go mode, we often start things that may, over time, prove to be either no longer needed or simply not the best way to go.

I recommend that you have a regular discipline of reviewing all open projects, priorities, responsibilities, etc. Ask yourself which of these continue to be worthy of effort and focus. 

The fact that you may have already invested a lot in these initiatives is not relevant. Those are sunk costs. All that matters is, do they add value going forward?

In fact, this notion of future benefit vs. sunk costs brings up a key question I regularly ask CEOs struggling with an issue: Assume you have started something or hired someone and you’re not sure you made the right decision.

The question to ask yourself is: “knowing what I know today would I make the same decision”? If yes, then keep going. If not, then, no matter what, you know that you need to undo that prior decision. You need to stop doing that thing. Or you need to remove that team member that’s not working out.

So, ask yourself regularly: what should I stop doing? 

The importance of values

ValuesBack when I was a seed investor I encouraged the entrepreneurs I backed to just focus on the bare essentials. My favourite line was was telling people that we don’t even have a company yet. We have a project that will become a product and if the market likes it, then we will build a company around it.

Far too often you see seed stage folks running around with fancy titles, plotting complex long term strategies and doing a bunch of other things that are totally irrelevant at that early stage.

However, as soon as you start thinking about building a lasting company you need to bring in a lot of new elements to that company-building process. One of the most important is the values that you stand for as an organization.

Continue reading The importance of values