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.

That’s a very important example to set, for an organization. It’s like going back to what I was saying about the jazz situation. We always want to bring in people who are individual and are bringing in unique ways of thinking and a unique style of playing. But those people have to be really humble. We never want people who think that they have all the answers. It’s pretty powerful, in an organization, when you have a senior leader who is able to say that and really be open to ideas coming from anywhere.

How would you look at Shopify versus Amazon, for example? Amazon have been the pioneer, as we said, in this decentralized structure and they constantly seem to be innovating, bringing new products, focusing relentlessly on the customer. How do you look at the parallels?

There are different stages, in terms of how long they’ve been around and how they’ve scaled. I will say this, Amazon – and I don’t think this would be a surprise to most people – the business is, and has been for quite a while, very much around operational efficiency. They’re trying to squeeze every last cent that they can out of the system. When I was at Shopify, I never saw that kind of thinking around the dollars and the cents. It was there, certainly, and there were people who are in finance, there and it is their job to think about that. But it was never really about that. It was always, much more, about identifying interesting problems and solving them, in a unique way and in a way that would be a really awesome experience for someone. But yes, they’ve been a huge financial success and I think that’s a telling thing.

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