Ben Gilbert: evaluation

Transcript context

…Yeah, seriously. Another really fortuitous thing happens in 2007 when they made that switch. A Toronto-based angel investor named John Phillips discovers the company and he invests $250,000 at a $3 million post-money valuation which was pretty rich for—I have to imagine—a small company based in Ottawa, Canada back in those days. I imagine everybody's pretty happy with that these days given the current market cap. But John was a lawyer based in Toronto. He had worked with a ton of companies and he becomes a really important mentor to Tobi, especially through what's about to happen in the next year in 2008. Scott gets the early-stage startup bug again and decides that “Hey, this company’s scaling. It's a SaaS company, I'm not sure if this is really what I want to do.” He leaves and Tobi ends up having to take over the CEO role. From a kid who is an apprentice programmer who loves playing video games and his parents thought, “Is there something wrong with him? He doesn't talk to people or other kids? He just sits at his computer all day,” all of a sudden now he's shoved into the role of being the CEO of this company that is growing pretty incredibly quickly with all these customers. As he becomes CEO of this company, he doesn't just do the job the same way that any other CEO would do it. He applies his engineering mindset to this. When you listen to Tobi in interviews, you can tell that he thinks about things in this extremely logical, extremely structured way, he's so low ego, he's all about measuring results and going back and revising past decisions, changing his mind when they're in the face of new data, being wildly structured about decision making. He basically becomes the engineer’s engineer. He's an amazing, amazing engineering leader and it really leads to them being able to attract incredible talent in that first set of employees because the set of really talented technical people, many of them who had been open source contributors to the Ruby on Rails project were dying to go and work with them. Yeah, totally. People are moving from Germany, from other places around the world to Ottawa to come and work at this company. We take a step back and we now have a fairly young CEO who was an engineer, has no management experience, in charge of a high-tech software company in Ottawa, Canada. This doesn't seem like a recipe for success. But Ottawa actually has some interesting features. There were plenty of old-school technology companies that were in Ottawa and Ottawa’s not far from Toronto and Toronto, of course, has great engineering universities and technology companies. Nortel was in Ottawa, there were a few chip companies in Ottawa, but there was nothing interesting happening on the software technology front there until Shopify came along. I think Nortel had fallen on hard times by this point. All of a sudden, here's this super interesting hot Web 2.0 software company based in Ottawa and they're able to recruit just incredible, incredible technical talent. He jokes about Tobi being the engineer’s engineer as a CEO. All this is happening and he was really wrestling with like, “What do we do about this? We're growing. Should I raise venture capital? I think the market opportunity for this is big and getting bigger. Should we take into being a growth company and put fuel on the fire?” He wasn't sure, so he decided, “You know what? I'm going to run a test.” The company has become cashflow positive in 2008 with about 10-ish employees. They made over a million dollars in revenue in 2008. They landed their first major customer that year which was Tesla Motors, which started selling the Roadster on Shopify. To this day all of Tesla’s online sales still run on Shopify which is pretty amazing.…

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