Former Twitter employee describes what it was like to work with Jack Dorsey on early versions of the site

Scott Olson/Getty

Tony Stubblebine, early Twitter employee and CEO of Coach.me, originally published this post on Quora as an answer to the question, "What was it like to work with Jack Dorsey on the early versions of Twitter?"

Jack was great. I loved working with him. And he also taught me an important management lesson.

We worked together at Odeo, which is where Jack built the first version of Twitter [launched in 2006]. He was an engineer and I was his boss, the VP of engineering.

When I joined Odeo, most of the team was already in place, including Jack. There was a lot of confusion about whether I was there to help scale the team or whether we were wrong and needed to start pivoting.

I think we experimented with at least six different pivots.

One of the problems with not having clarity was that it was really hard to manage that team. Several of them weren't getting along and were acting out. But I didn't know enough about what we were doing to just fire any of them.

So I spent most of my time trying to massage people's egos.

However, during all of this Jack was perfect. He came in early, got his work done, volunteered for work that other people didn't want to do. He had a strong sense of duty and would work on messy code in any language.

There was a key piece of infrastructure written that was hacked together by one of the founders. It ran on a single desktop computer sitting in our server cage. This thing broke all the time and Jack was the only one willing to fix it.

Given that, I didn't really need to spend much time managing Jack. I supported a raise and voted him some bonuses. But mostly I was working with the other people because they were causing a lot of headaches.

I spent enough time with those trouble people that I consider several of them friends. But they were difficult anarchists back then. One of them sent me an apology note years later. He found a photo from one of our stand-up meetings where he'd refused to stand. That was his idea of anarchy.

And I think that's a big management lesson — it's easy to get sucked in to spending all your time with the hard cases. If I could do it over, I would have spent more time with Jack. It's not that he needed managing. But I think he could have had an even easier time getting his viewpoint across if I'd spent more time supporting him.Scott Olson/Getty

I do have a couple of anecdotes about Jack from those days.

He definitely had a sparse sense of design. You could tell he was already thinking about focus and simplicity, especially in his own life. He only owned a few things, but those things were all of the highest quality.

One day I asked him for advice about a gift. I wanted to get my mom something cashmere. Jack's eyes lit up and he got very excited telling me about a boutique that specialized in cashmere. So I went to this boutique. It was deep in some alley — I never would have found this myself. And it was the most expensive clothing store I'd ever been in. The cheapest thing there was a pair of $200 cashmere mittens. That was Jack.

The thing I don't remember is why we all thought Twitter was such a good idea. As I recall, we jumped on it really early, even before we had a prototype.

I think part of the issue was that most of us weren't yet on Facebook. So we didn't have a way to keep in touch with our friends.

So when we had a version that was friends and family only, we all had a magical experience of feeling connected to our friends.

My job during the very early days of Twitter was mostly to keep massaging the issues with the engineering team. Twitter was too small to have the whole team working on it. We also didn't know if Twitter was going to be a real thing on its own. So my job was mostly to keep Jack safe from distraction. Once I had to yell at someone who had kept trying to check in fixes to the code. But mostly, I was organizing the rest of the team to work on other Odeo projects.

A story that I've never seen told was about sailing.

Rabble, one of the other engineers, had bought a boat and needed to sail it down the delta to a dock he was renting in Berkeley. He asked for volunteers and said it was supposed to take half a day. Jack and Noah volunteered to help him on a Saturday.

When the three of them came to work on Monday they were beet red, dehydrated, and looked like they'd been stranded on a desert island.

They'd managed to run the boat aground.

Jack, who actually knows how to sail, was below deck getting changed. And he could hear Rabble and Noah speculating about the signs they were seeing on the delta. "Ten? What does 10 mean?" "Five? What does five mean?"

Boom. Five means five feet. The boat ran aground and they were stuck there for awhile. Everyone who came to help treated them like morons. But that was a great anecdote for that team. Noah and Rabble were up for winging it. Jack was up for adventure, but he never would have run aground because he was so detail oriented.

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