Interview Transcript

Is there anything that really sticks out to you, that was different about the behavior of Shopify, as an organization, versus IBM, in terms of culture and, as a business?

The main thing is really the openness to learning and building that in, from the beginning. Everybody in the organization, even the leadership, setting the example of, we don’t have all the answers; we’re figuring stuff out and we’re learning, just like everyone else. It’s also the willingness to make hard decisions, quickly. In a lot of organizations, there are things that just drag on, forever. In the meantime, there are detrimental effects, so being able to make those decisions is pretty critical.

One thing that was interesting was, even just seeing, just recently, at the beginning of the pandemic, Shopify announced that, even after the pandemic was over, they were going to continue working from home. They were going to be a fully remote company. They made that decision pretty early on.

Tobi always seems to be at the forefront of these decisions and taking the plunge much quicker than others, it seems?

I mentioned about that mindset of being very open to things. One of the things, for these younger companies and younger leaders, is that they have a strategy for where they want to go or, at least, they have a direction, they have a vision for where they want to go, but they fully admit that, exactly how they’re going to get there, they don’t know that. In business, we’ve always had this idea. Sometimes, you’d actually get asked, if you were looking for investors, what is your five-year plan? To say, we don’t have one, that might have been a bad thing at some point. But there’s the reality there now that, oh, it’s okay to say that because you could have one, but it’s BS. Who knew what was going to happen, with what’s happening now? Nobody knew this was going to happen and it’s changed the world. So you can say that now, but that doesn’t mean you can’t have a vision for what you want to achieve.

Old principles?

Yes, but you have to be open to how you’re going to get there. For sure, you probably know it’s not going to be a straight line. It’s going to deviate, here and there.

It almost seems as if he is empowered by being humble and not knowing; it’s quite paradoxical.

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