Hiring, Communication and Investors: Takeaways from Jack Dorsey Interview at Oxford University (Video)

I recently watched a good Q&A with Jack Dorsey at Oxford University. The video is a bit long and includes some history about himself and founding of Square and Twitter. I scribbled down some key takeaways (starting from around 45 min into the video).

  • Instrumentation is important. Twitter didn't have any in the early days. It was a major problem, especially when things broke and the site went down. When they eventually added instrumentation (dashboards and better system monitoring), it made a huge difference. They could now point to the issues (instead of guessing) and actually fix them. Sure enough, when Jack started Square one of the first things he coded was a dashboard to track the system.

  • Twitter had some serious internal communication problems in the early days. Kind of ironic for a company that builds a communication platform. Apparently it was so bad that the Operations group and Engineering didn't speak to each other. As Jack puts it, "Any organizational difficulty eventually manifests in the service itself". In other words, users will pick up on it and the service will suffer. It's super important not to let this happen and a great product/service starts internally.

  • Hire great people who share the same purpose and vision. And let them go when they don't. Jack shares one of his mistakes/regrets from the early days of Twitter (he was CEO at the time). Twitter's technology lead at the time clearly had to go. He was a problem and a**hole to work with, yet Jack was in a pickle because he was the only guy that could bring the site up when it went down. After 6 months of deliberation, Jack finally made the tough call and let him go. He was crying. The team was crying (they were at 7 people at the time). But he said the most remarkable effect from making that decision, was that it allowed other leaders on the team to emerge in the absence of the problem guy that left.

  • At one point Jack says, "If you take money from someone, it's kind of like hiring someone you can NEVER fire." That really resonated with me. He says that when he looks for investors, he does not just look for the popular or well-known VC firms. He looks at the people in those firms and determines whether those are people he'd want to work with. In his case, he looks for people that have actually used his product or service (e.g. Square and Twitter). Interestingly, he added the almost always says "NO" to investors that go straight to a term sheet. The reason being that if they do not ask tough questions upfront or during the pitch, they are not going to ask the tough questions at the board meetings when it matters most. So next time you are thinking about taking money from someone, you have to think "I'm adding this person to my team."

  • When it comes to the product, Jack says "If we constantly react, we are building someone else's roadmap instead of our own vision." It's something to be mindful of especially from influential stakeholders like investors but also applies to customers and sales.

  • How did the brand 'Twitter' and the word 'Tweet' come about? Jack says originally a tweet was just called an 'update'. Also, the name was originally 'Twtrr' (see Jack's first tweet ever). The service was designed around the constraints of SMS (text messaging) so that it could be accessible to anyone in the world with the most basic device like a flip phone (a principle that still holds true to this day). When 'updates' would go out, it would make people's phones buzz. They wanted a name that exemplified this 'buzzing' behavior, so some of the ideas they came up with were 'jitter' and 'twitch'. But those had a negative connotation. One of the guys at Odeo (the incubator Twitter started at) looked in the dictionary and found the word 'Twitter' (defined as "to utter successive chirping noises", "to talk in a quick and informal way about unimportant things"). It was perfect! Later users came up with the phrase 'Tweet' and it stuck.

  • One final thought Jack adds is that there's a lot of effort these days to expand human kind to outer space and beyond. But he sees potential to go the opposite direction. As he puts it, technology provides a model for understanding the depths of the human consciousness. I agree with him on that.

What are your thoughts? Let me know in the comments or even better, on Twitter.

Full video below: