I developed an early (technical) following because I was one of the people behind Ruby on Rails. That lead to the first few customers because technical people are often asked for recommendations for software. Keep in mind this was in 2006, a very different time from today.

Awesome. If you had to do it all over again, do you think you could have been successful with Shopify if you'd started today?

Building companies is 90% luck (timing, competition, demand, macro trends, technology penetration, also health & passion of the team). So... I doubt it.