The Exchanges

Q Alright, so you go to work for Google. You become a Google employee because they acquired Blogger, which was a really big deal at the time. Did you, did you, was it clear to you soon after you arrived to Google that you were not fit to work in a big organization?

A Yeah, I felt like a stranger in a strange land. I, and I was like employee number 800 at Google, so it's laughable how, how small it was. Same size as the, as the high school I went to. Um, Uh, and it felt similar. It felt, well, it felt like a college, but yeah, I didn't know how to operate and I, and they didn't know what to do with me either because they'd not done any acquisitions. We were literally the first acquisition that involved people. They had bought some IP, but we're the first group of employees to come in who were Googlers, but not. And so we were just kind of plopped in there and, uh, You know, trying to figure out how to survive. And to their credit, a lot of, tons and tons of big companies bought these tiny internet things at the time, and then they would just die.

AI assessment note: “Yeah, I felt like a stranger in a strange land.”

Q you made some money from Blogger, and the, and the new idea would become, you started a podcast platform in 2004, called Odeo, which must have been, I mean, this is before Apple Podcasts, this is like gotta be one of the first Podcast. What, what, what, what even was a, did you call it podcasting? Did you say, hey, let's make an audio platform? Tell me about this idea.

A Yeah, it's funny how this came about. I had this neighbor named Noah Glass, who was a, um, fun, boisterous, entrepreneurial guy who invented a way to call a telephone number and leave a voicemail that would end up on the web. And then, Biz Stone, later co-founder of Twitter , he worked with me at Blogger, and we were driving home from Google one day, and just kind of brainstorming about it. It was one of those moments of, um, independent invention. Kind of to help Noah, because we're like, no one's, you know, it's cool you can record these, but no one's gonna listen to these things on their desktop computer. What if you get them on their iPad? And we were thinking about what the technical solution is to that. And then, we started looking into it, it was like, around the same time, people like Adam Curry and Dave Weiner had started talking about podcasting.

AI assessment note: “around the same time, people like Adam Curry and Dave Weiner had started talking about”

Q else, which you did. It would, it's no secret to people listening, it was, it was going to be medium, um, which is kind of amazing, because it's like the first, your first really, the thing that you first really had success in, which was blogging. You kind of go back to that. It's like a three 60 return. Tell me about what, what did you want it to do?

A Medium, the seeds of medium were really planted while I was still at Twitter, and the initial genesis is Biz and I, Biz who came over from Twitter, He and I were talking. One of the things we learned at Twitter, which we really believed in, was this idea of constraints. So we're like, listen, what if we create a writing platform that wasn't so short as Twitter, but still was, you know, not too short, not too long. And I, I walked up to the whiteboard and I wrote medium. I was like, I don't know what it is, but we should call it that. And then, um, the idea was essentially what we had learned from social networks was that The value was in the connectivity. Like, if Twitter just did what Blogger did and posted your tweet to a webpage and didn't fan it out, if there wasn't this follow mechanism, it wouldn't be very interesting. It would, it would essentially just be Blogger. So, it's the distribution system that created all the value, and this is why I call my company as obvious. It was obvious to me that that should exist.

AI assessment note: “what if we create a writing platform that wasn't so short as Twitter”

Q I mean, blogger eventually started to get, gain traction. What, what, Started to happen. I mean, you know, within a year, I mean, this is 2001. And of course we know what happens in 2001, September 11th. I wonder if that had something to do with more people using it and more people going to blogs. What happened?

A Yeah. So blogging was kind of growing the whole time, despite the dot com boom and bust. And that was part of the reason that I didn't want to give up. Like it was Um, the numbers were good. And then, yeah, nine 11 was actually a big moment for blogs, and it's, it's when, the way I would describe it, it's when journalists started taking them seriously. Actually, nine 11, the day nine 11 happened, I actually spent the day aggregating, um, because there wasn't really a real-time search, and of course there's no Twitter or anything, but people are writing about their experiences, including a lot of people in New York, And it was hard to find out, you know, hard to find this on the ground information. So I actually spent the day culling these posts as they're coming in from database and put up special pages about that. And some really big blogs emerged after that time that really covering the news. And then of course, newspapers and magazines started creating their own blogs around probably after that time. And then, yeah, we continued to see growth, for sure.

AI assessment note: “nine 11 was actually a big moment for blogs”

Q Um, I guess you did basically get close to going out of business, right? Because at a certain point, Pyra, um, you stopped, you stopped being able to pay employees.

A That was a very stressful time. Basically, I We didn't pivot to enterprise. We didn't get any customers. We still didn't have any revenue. And then eventually it just got to point. It was like, look guys, we're not going to be able to, um, I think there was even a payroll we missed. And then I sat everybody down and said, we don't have any money to pay you past this next pay period. So you're welcome to come back. I think this is on Friday. You're welcome to come back. I'm going to keep working. Um, if you come back and work, you know, we'll pay you when we make money, but we're out of money. And then the next Monday, I came back, and I was the only one there.

AI assessment note: “I sat everybody down and said, we don't have any money to pay you”

Q in retrospect helpful, but the rap on you was you're too slow to make decisions, and also you were prone to hiring people you knew, which is a big no-no for some people. Again, Not saying that's right or wrong. That was the criticism that's, you know, and the massive, you know, that millions of column inches have been written about Twitter. That's come out. Do you think that's fair?

A I think both are fair. I was not a great CEO by any stretch, and I think I was getting better at What I was very good at was product, and knowing, in my opinion, product and strategy, and knowing where to take the company, what we should build. But the company got to a size where lots and lots of other things were important for the CEO to do. Um, certainly management, finances, leadership, giving confidence to the entire team. But I think in a lot of cases I was slow to make decisions because I was, I was avoiding conflict. I didn't want to make decisions that other people disagree with. I didn't have my, if I felt something intuitively, but every, like the evidence or the data or the logic, everyone was arguing something else that I would just, I got frozen. Or if the decision was about a person and I, I, I was I was lacking the confidence to, um, really upset people, and that was a huge weakness, for sure.

AI assessment note: “I think both are fair. I was not a great CEO by any stretch”

Q Um, and you met this woman named Meg Horahan, this was in the late nineties, and I guess she was, A developer and designer living in San Francisco. Um, you meet her, and I, I guess by chance, and the two of you decide to start a business together. Tell me about, about that, what happened?

A Um, when, so I, when I left O'Reilly, actually, I'd gotten paid enough. By the way, when I got to O'Reilly, I was in debt To the IRS. Cause I didn't pay payroll taxes at my first company, but I made enough money to pay off the 10,000 dollars or whatever it is, which seemed insurmountable before that. And then, and I had learned enough more programming that they actually hired me as a contractor at O'Reilly after I quit as an employee in marketing. And so I, I rolled that into some other contract programming jobs. I ended up working through agencies and That's when I met Meg. I had already decided to start a new company. I knew what it was, and we started what we called Pyro Labs. We call that project management or productivity app that was web-based.

AI assessment note: “That's when I met Meg. I had already decided to start a new company.”

Q Even with the, the success that you had, and the, and the psychological Kind of, let's say, foundation of wealth that you had built? You still had that?

A For sure, for sure. That didn't really change anything, and I hadn't really done any work on myself at the time, and I think this is, like, for entrepreneurs, so, so important to realize, like, what is driving you, and where are your blind spots? I had no idea. So when I would hear, I got a little bit of feedback, and by the way, Somewhat ironically, the board of Twitter had a lot of conflict aversion. Because they never, never gave me that feedback to my face. I didn't know I was going to be fired at all, because no one ever told me I was doing a bad job. So there was a whole culture of conflict diversion, and my, my execs, who were complaining about me to the board, also weren't telling me. Everyone was avoiding conflict.

AI assessment note: “For sure, for sure. That didn't really change anything”