That's a really good question ...

In terms of product / tech-stack I don't think I would change anything.

In terms of marketing and word of mouth I think we should have given away hundreds of free accounts in the early years (2006-2010) rather than trying to chase them down as paying customers. I believe we had a lot of decent word of mouth but I don't think I appreciated the power of influencers and their ability to amplify a message.

As for business decisions, I continue to wonder how much business we miss due to not having a Canadian location and we have considered deploying in Montreal for years now but have not pulled the trigger. I don't know if a Canadian location (but still a US company) solves the regulatory requirements of Canadian customers.