Crafting Success

Interview with Chad Dickerson

April 27th, 2021   |    By: Sarah Lacy    |    Tags: Stories, Strategy

Editors Note: Earlier this month Etsy revealed in its  Q1 earnings report that the board is replacing Chad Dickerson, who has been CEO since 2011 and took the company public in 2015.

Josh Silverman, who joined Etsy’s board in November, will take over as CEO, while fellow board member Fred Wilson will be taking over Dickerson’s role as chairman of the board. Etsy is also losing CTO John Allspaw.

Dickerson said in a statement: “It has been an honor to lead Etsy as CEO for the past six years and the three years before that as CTO, the Board decided that it was time for new leadership to take Etsy forward and I support that decision.”

Here’s something you don’t hear in today’s unicorn “crushing it!” era of startups: “There’s something about losing that makes you better.”

That was Chad Dickerson, Etsy CEO in 2013, when I interviewed him about how he wound his way to the company. He lived an up and down career of almost accidental successes and failures that shouldn’t have been failures. From the former category: In the 1990s he was one of the first “Webmasters” of a daily newspaper in North Carolina making $16,000 a year. Within a few years, the dot com boom carried him to a job at a pre-IPO company in San Francisco. From the latter category: His valiant attempt with Valley heavyweights like Caterina Fake and Bradley Horowitz to make Yahoo innovative again.

Etsy itself has been a company you could characterize as having accidental successes. Like Twitter, it withstood an early revolving door of leadership when it’s founder CEO didn’t scale. Like Twitter, it had massive technical issues. And like Twitter, it was the uniqueness of the product and the impassioned community that always saved it.

Like Twitter, it has also had a rocky road as a public company.

Unlike Twitter, Dickerson has stayed the CEO the entire time. “No one’s going to applaud you if you come into an easy situation and make it marginally better,” he said of the technical mess he inherited back in 2008. The same could be said of the challenges in scaling Etsy’s business as a public company.

In the following interview, we talk about Dickerson’s unconventional journey. If you are hitting a nadir in your own career right now, I guarantee this story will make you feel better.

Sarah Lacy:  You came to Etsy as the CTO before you became the CEO. You were, by your own admission, a horrible coder. You took two math classes in college because it was the least you could take. You were an English major. You like Shakespeare way better than PHP.

Chad Dickerson: Yeah. When I was in high school or whatever, I did well in math and science. When I went off to college, much to my parents’ chagrin, I told them that I wanted to be a total liberal arts humanities person. My dad’s an engineer and my brother’s an engineer.

I enrolled in school and became an English major. Being an English major is still a joke. It was a joke 20 years ago. It’s still a joke now.

SL:  I was an English major, too. Just know everything you say also applies to me.

CD:  See? You can be an English major. I was always really excited about journalism, of all things, which was really exciting. I was telling Sarah earlier, I had this weird obsession, not because I liked him, but I had this weird obsession with Richard Nixon ‑‑ the character Richard Nixon ‑‑ and Watergate.

I’d read in high school all about Watergate. I saw the movie, “All the President’s Men,” with Dustin Hoffman and Robert Redford running around the newsroom, talking to Deep Throat and all that stuff. I really wanted to work in a newspaper.

When I graduated, I didn’t get one job, I got two jobs. The first job was a minimum‑wage job, working at the newspaper in Raleigh, North Carolina, “The News & Observer,” which happened to be the first daily newspaper on the Web in the United States.

My job there was to basically get a copy of the newspaper. There was copy inside their electronic system. The paper copy was considered the authoritative copy. I would compare the paper copy to the electronic copy and make sure that they were the same before the newspaper sent them off to LexisNexis, which licensed these things. I did that all day for…

SL:  It’s just like Watergate.

CD:  Just like Watergate. I remember I was making $6.50 an hour. I happened to be working around these people who were building the first websites. This is like 1993, 1994.

One of my jobs was to put TCP/IP software on all the Windows computers in the whole building. I don’t know how I got that job. That was one job. My other job that my parents were really excited about was Pizza Hut.

I’m not a school name name‑dropper, but I went to Duke, which is an expensive school. I was the first person in my family to go to a private school. This is going way back. To tell you how big it was to go to Duke in my family, my grandfather, who was a tobacco farmer in North Carolina, where I’m from, actually couldn’t read or write.

I was the kid going to Duke to major in English. I grew up reading my grandfather Hallmark cards that he couldn’t read. My parents were super‑excited that I went to Duke and was this golden child in the family. Then I went to work at Pizza Hut.

I was working at the newspaper to supplement my Pizza Hut income.

I have a feeling I’m going to hear this from my kid one day. I told my parents that I didn’t know what I wanted to do with my life, and there was no better way to figure it out than to drive a truck around, delivering pizza and thinking about it.

You can imagine me in 1993 driving a Pizza Hut truck with one of those things on this truck ‑‑ I had a pickup ‑‑ listening to Nirvana. It was Nirvana and not Pearl Jam, and I was thinking about the newspaper. It was actually a great job. They offered me a manager position.

SL:  God, you could’ve had a sweet life.

CD:  I turned it down. By the way, there were more English majors and biology PhDs working at that Pizza Hut than there are at a university.

At the newspaper, I was working with a group of people who were basically hand‑cranking HTML to post new stories to the site because there were no automated systems or content management systems.

One of my co‑workers pulled me aside, because I did my work really fast. He said, “If you learn how to code, you can write a program, and it’ll do all your work for the whole day, and then you can do other stuff.”

I started learning how to code. That was really fascinating. Basically, I got to a point where I would get 15 stories to hand‑crank HTML. I wrote a Perl script, and I’d run it. I would have nine hours to play around on the Internet.

I almost got fired from this job because, basically, in the early days of the Internet ‑‑ I’m saying this in my old man voice ‑‑ I mentioned that I was putting IP software on all the machines on the network.

As I learned more about networking, I realized that each of these machines had a public IP address on it. I basically built a website on my computer at my desk and started posting to newsgroups.

Courtney Love had come to town and was playing a show. I got some photos that were not published in the newspaper and created my own site and published to, like, “Hey, I work at the newspaper. These are all these photos they didn’t publish that you can come see on my website.”

A little while later, the network guys are standing at my desk because they’d noticed this huge spike in network traffic on my desktop.

I got pulled into the office of Frank Daniels, Jr., who was the publisher of the newspaper, sort of a big deal in North Carolina politics. His grandfather was Josephus Daniels, who was Secretary of State for Franklin Roosevelt. This guy was the president of the Democratic Party in North Carolina. There was a photo of Bill and Hillary behind him with their arms around him, and he said, “I about have half a mind to fire you, boy.”

But he said he was going to let me go [with a warning] and, basically, I got a raise shortly after that. They put me on the Web team. I learned to code. This newspaper was a pioneer in something that was called computer‑assisted reporting. In 1995, the group I worked in, I played a very minor role, but they won the Pulitzer Prize for a series on the environmental impact of hog farming, and they did it by analyzing data that they gathered from government agencies.

I was loading data in the databases, and looking at phone call records, and that kind of stuff. That’s where my fascination with technology came from. Before that, I was a guy who knew a lot about Shakespeare and how to make pizzas at Pizza Hut.

SL:  How did you wind up in Silicon Valley?

CD:  I worked at the newspaper for a while and growing up in North Carolina. This sounds so funny to say now, but Atlanta was the capital of the world.

I got a call from the newspaper in Atlanta to be their webmaster and I went. I was the first webmaster, and I’d stopped delivering pizza three months before. Then I was the webmaster of the 10th largest newspaper in the country.

SL:  This was what was so exciting about the web in that era. Literally, there was no one who knew anything about it. It’s almost like, “You’re fresh out of school. I bet you know about this.” It was this land grab of job opportunities for people who had no idea, but no one else did.

CD:  That was crazy. I’ll never forget. I was making like $16,000 in Raleigh, North Carolina. I actually qualified for a low‑income housing loan and bought a house. That’s how much I was making at the time. I went down to the newspaper and they liked me and they said, “What salary you need to make?” and I just tripled the number of what I was making in my head and they said, “OK,” and I was like, “Oh my god!”

It was only my third time on an airplane. It’s an hour of flight from Atlanta to Raleigh and I was like, “Two beers please.”

I went to work at the Atlanta paper. I’ve always been a news junkie. I was 10 years old watching “CNN Crossfire,” if anyone remembers that. I was a nerd. Remember the Nixon thing?

CNN called me and they were building a sports website, CNN Sports Illustrated. It’s a joint venture between Turner and Time Warner and they needed someone, and I had built a bunch of baseball sites at the Atlanta paper, so I went to work at CNN. Super intense. Ended up in the elevator with Ted Turner and Jane Fonda arguing sometimes.

It was fascinating. I was having the Atlanta dream. Then I went to a conference in San Francisco. Growing up in the South, San Francisco might as well be Jupiter or something. It’s not a place that people go to.

I went to San Francisco for this conference and fell in love with it very immediately. The head of, guy named Harry Motro, had just joined Infoseek as the CEO. I landed in Atlanta, I called Harry and said, “Can I get a job at Infoseek?” I went out and interview at Infoseek. Then I landed back in Atlanta, and I saw an advertisement on for a VP of Technology.

I wrote them a cover letter and I said, “This is the only VP of Technology resume you’re gonna get from a Shakespeare scholar,” and all this kind of stuff. I went to Salon and just some of the most fascinating total San Francisco characters. Guys who wrote for Rolling Stone and hung out with Hunter S. Thompson.

I was the guy who was a few years out of delivering pizza and had not left North Carolina much, and I’m sitting with these guys who were at Woodstock and Altamont, who hung out with Keith Richards. I was fascinated by that whole lefty media scene.

That was just the most amazing experience. I was out there for 10 years, and I would say the people I met at Salon are some of my best friends today. One of them is Caterina Fake who was an art director.

Caterina and I built Salon Shopping which is basically selling coffee mugs with Salon logos on it. Caterina designed it and my team built it. I was still coding a little bit at the time. That’s where I met Caterina. A bunch of stuff happened in between, but Caterina is basically what lead me to Etsy.

SL:  You guys also worked together at Yahoo. Right?

CD:  We did.

SL:  You were part of this whole gang at Yahoo. When Flickr got acquired by Yahoo, it was this moment in time…Flickr and Delicious were these really early sexy web 2.0 companies.

This was back when everyone was like, “There’ll never be another big consumer web company,” and all the Valley was super down on consumer web. These little companies came out of nowhere. When Yahoo bought Flickr for $30 million or something like that, people were shocked at the amount of money. Now we have Instagram today.

There was this one moment of hope in the last couple sad decades of Yahoo where it was like the Flickr people will find a way to make Yahoo cool. Flickr and Delicious will find a way to make Yahoo cool. Caterina tried her hardest. You guys had this whole Brickhouse thing. It was almost as if you were a startup.

I’m really interested in that, because that was sort of this one point where we thought Yahoo could turn around. What were some of the things you guys tried to do in‑house? What was some of the resistance in…Why did it, ultimately, not work?

CD:  Those are great questions. I joined Yahoo in summer 2005, working for Bradley Horowitz who’s now at Google. Brickhouse hadn’t started yet, but Bradley had started a group called the Technology Development Group, which he later changed the name of it to the Advanced Development Group because he liked the acronym ADD.

He started with the acronym and went backwards. That’s the way I remember it. The idea of the Tech Dev Group was to, basically ‑‑ this sounds almost silly when I describe it, ‑‑ it’s, basically, spread innovation throughout Yahoo.

I think, in retrospect, the idea of starting a team to spread innovation is the seeds of your destruction. It should be inherent. That’s what I learned. I think Bradley did a great job, and it was a great idea at the time, but you can’t force people to innovate. I had a little joke back then, when things started going bad, that Yahoo had this idea that you could point a gun at someone’s face and say, “Innovate!” and it would just happen.

The point I was trying to make is that you can’t demand innovation. You have to create an environment that creates innovation.

One of the first things that we did ‑‑ and all the Brickhouse, and Tech Dev, and Hack Days were all connected ‑‑ is we, in December of 2005, did the first hackathon at Yahoo. I think people talk about the origins of hackathons, but I think it’s one of the first, if not the first, large‑scale hackathon in a company. I was leading on that and working with Bradley.

We had no idea it was going to work. It’s weird to think about now, doing a hackathon and not sure if the hackathon is going to work, but it was hugely successful. We did them all over the world. I went to multiple continents and did them in India. They’re all the same, in a way, except for the food.

SL:  But you got in trouble for the first one, didn’t you?

CD:  Yeah. It’s amazing how many different people connect in the story. Jeff Weiner, who’s the CEO of LinkedIn, was the head of the search group, which was like 3,000 people. I think he’s one of the unsung heroes in getting hack days off the ground, because I told him that I’ve always studied hacker culture.

I was like, “Good things happen when developers are allowed to do what they want to.” Eric Raymond, the famous open‑source guy said, “Every good work of software starts by a developer scratching their own itch.” I talked to Jeff and said, “I really need complete lack of interference from the company to do this hack day.”

Jeff said, “I’ll send an email to all the senior management that they can’t bother you for a day.” We’re in this heated battle [with Google back then] and Jeff saw innovation as so important that he was able to shield me.

I think the challenge that we ultimately found with hack days is that building something in a day or two days is not necessarily a business or even a product.

The idea with Brickhouse, in my mind, was ‑‑ If you took these short bursts of energy, and you sustain them over a longer of time, and you actually built a startup out of these things inside the company, you could build these disruptive businesses, and so we did that. I was a tangential player, because I was working on hack days.

But, over time, management changed. When Bradley left to go to Google, I was put in charge of Brickhouse. We were able to ship some things ‑‑ Fire Eagle and other things that maybe forgotten at this point. I think the thing that I learned is that, personally, I will never again work inside a large company where my job is to build startups inside the large company.

Building startups is hard enough. I think, if you want to build a startup, if you’re working for a large company and you’re in a team that says, “We’re the startup inside the large company,” that just doesn’t work.

SL:  Why does it not work? You see over and over again, it doesn’t work, but there are still companies who always believe they can do it. Amazon has done this to a degree. They have their two‑pizza teams and some interests. There’s a lot of businesses within Amazon that have come out of that, but…

CD:  I may be too absolutist. I think it can work in some cases. In most cases, the classic text on this is “Innovator’s Dilemma,” Clayton Christensen, which, if you haven’t read it, it’s a must read.

I think what happens is that what is seen as an advantage, like the size of the company and the resources of the company, in most cases are actually a disadvantage. I’ll give you a very specific example that I learned very early at Etsy.

In the early days of Etsy, which were really tumultuous on the technology side, we were going into my first holiday season and we didn’t really have a very good capacity planning, and there were all sorts of problems. We realized that we needed two servers.

We literally needed to order the servers and have them in the rack the next day. It was two days before Thanksgiving. In Yahoo, if you needed two servers, there was literally a meeting every week called HRC, the Hardware Review Committee. You’d have to go talk to a group of executives and say, “I need two servers.”

Then they would say, “Why do you need two servers?” You’d have to explain it, and then it would go through the procurement system, and all this stuff. It was a matter of weeks. Fast forward to Etsy, we needed these two new servers. I pulled out my AmEx card. We charged the servers. We got them delivered to a FedEx facility in New Jersey where our data center is.

I went down to the Zipcar lot, got a Zipcar, drove over to New Jersey. It was a Scion, I remember it really clearly. We loaded servers into the car, drove across to Secaucus, New Jersey. We opened the trunk, the guys were at the loading dock, and we put the servers in the rack.

That’s a really small thing, but I think that the bureaucracy in a large company, in very small incremental ways, all adds up. Yahoo would’ve probably figured out a way if that was going to hurt Yahoo Mail, but I’ll just never forget how quickly you could solve problems once you’re in a real startup.

SL:  Evan Williams has said similar things. When he sold Blogger to Google, he thought he would…They always talk about these great resources you’ll have, but the hoops he had to go through to hire anyone. He couldn’t even hire friends of his because they didn’t have the GPA requirements that Google needed to make a hire. You wind up not having the resources promised and more problems.

CD:  I think that’s true. This is not to discount big companies. I would, in Yahoo’s defense, I feel like I learned so much at Yahoo that I’m applying day‑by‑day.

One last thing I want to say about Yahoo, my experience there. There was a study done. They basically figured out that there were more CEOs of successful startups now from Yahoo than there were from any other company. I learned a lot. I think the challenge at Yahoo was, as it is with managing any group of people, we had this massive array of raw talent and we weren’t able, as a company [to succeed].

I’ve talked to a lot of people who were there. We considered it a failure ourselves because we were there. We weren’t able to make it work.

SL:  There are so many who have left Yahoo and been more successful than they were at. Jeff Weiner’s a great example of that. When he took over at LinkedIn, I don’t think anyone was like, “Oh, this is going to be phenomenal,” because he was just another one of Terry Semel’s guys.

He’s turned out to be a great CEO. I think one reason there were good managers created at Yahoo is because people viewed all of these little parts of Yahoo like their own small business, but that’s also what made it really dysfunctional as one company.

CD:  Right. Yeah, I agree. I talked to a DC friend of mine who’s invested in a number of companies that are Yahoo or that were bought by Yahoo and that sort of thing. We were talking about how there’s something about losing that makes you better.

I think one of the reasons that a lot of great managers have come out of Yahoo ‑‑ people like Jeff Weiner, who I’ve learned a lot from and still learn a lot from ‑‑ is that it’s one thing to go to Google and work on AdWords, and success has many fathers. There are probably 500 people who’s played a key role in AdWords, but you can never really tell who’s really good or not.

SL:  Right. Google made a lot of people look good.

CD:  Google made a lot of people look good and a lot of people at Google are really good, but I think getting beaten down a little bit is actually good for your psyche. I felt that, when I came to Etsy, I had just come from Yahoo, things didn’t go in the direction I wanted.

I felt ‑‑ and this is what my friend said ‑‑ there’s like this hunger in former Yahoo people that I think you don’t really see as, I think, uniformly necessarily in former Google people.

SL:  I assume you came to Etsy in part because of that friendship with Catarina since she was involved in the company. What was the reputation of the company at that point, and how did you feel about moving to New York? New York, then, and the tech scene was certainly not where it is now.

CD:  I have to say, Catarina was trying to get me to meet with [Etsy founder] Rob Kalin for weeks. I was really busy at Yahoo trying to change Yahoo and running Brickhouse and that sort of thing. I remember it took a long time to get me to come out to New York.

I told my wife ‑‑ I had just gotten married a year earlier ‑‑ that, “New York’s really fun. Let’s go out and talk to Etsy and it’ll be like, what I call, a vacation interview.” I came out to Etsy. It was this weird thing, it was in July and it was 75 degrees and not humid, so there was some kind of special thing going on.

I had just gotten married a year earlier. There were contractors in my house in Berkley remodeling the kitchen. I had just gotten married. We landed in New York, met with Rob, and walked around Etsy. I had been learning about the community a lot.

After spending time in New York, a 75 degree July day, which was insane, my wife and I walked through Central Park and there’s a Bon Jovi concert.

I’m not a Bon Jovi fan, but…

SL:  Yes you are, come on.

CD:  OK, everybody’s a little bit of a Bon Jovi fan. There was this, I want to say, magic in the air. Rob is a very good salesperson and, I think, really compelling when you talk to him. Walking through Central Park hearing, “Living on prayer, good night.”

It’s like, “Man, this is New York. This is so great.” On the way back, my wife and I were talking. [We were on] the worst flight I’ve ever had. We were the last flight out of JFK and this huge black cloud with lightning. The pilot came on and said, “We’re the last plane cleared for lift‑off.” We flew into this death cloud.

I thought we were going to die. Once we reached cruising altitude, and we weren’t going to die, we were like, “Wow, that was really great. We just survived almost dying. Let’s move to New York.” Once you see your life flash before your eyes.

SL:  It’s this combination of weather, Bon Jovi, and a near death experience.

CD:  Yeah, totally.

SL:  If every New York company could just replicate that, you’d be able to recruit anyone from the Valley.

CD:  Exactly, Yeah. That JetBlue pilot had a lot to do with it. Literally, my wife was screaming. She gets mad at me to this day, because I was acting really calm. I was like, “If we’re going to die, I don’t want to freak out.”

So, we landed back in San Francisco and we decided. I remember I was 35 at the time people saying to us: “You’re supposed to live in New York in your 20s” We’re like, “What? Are we geriatric or something?” so we decided to do it and started packing our bags.

SL:  Did you have any idea what a mess Etsy was at the time?

CD:  No. You’ve probably heard the phrase, I think Woody Allen said, “Comedy equals tragedy plus time.” It’s been four years, so this is funny. Everything was working, but the site was really unstable. It was crashing all the time.

I think the seller community was restless and for a lot of good reasons. There was a blog that actually wrote an open letter to me. It was basically a list of demands.

The news was already out that I was joining, and the first thing I get is like a list of demands.

I remember the blog post said something like, “Take a Vicodin or your favorite pain killer and then read this list.” That’s what it said.

I joined and, my first week, the site went down and no one really knew it. There wasn’t a monitoring system in place. The monitoring system was someone calling somebody and saying, “Hey, did you know the site was down?”

The way I remember it is, the site went down. I was like, “OK, we gotta post that the site is down.” People were like, “We don’t have anywhere to post where the site is down.”

Then someone said, “Oh, yeah. We used to have a blog.” Someone’s like, “How do you login to” No one knew. I was actually recruiting a new engineer at a bar, actually doing the calm thing ‑‑ like I was doing on the plane when I thought I was going to die ‑‑ being like, “Yeah, we got some problems we need to fix them.”

I’m looking at my phone like, “Site is down. We have no way to communicate.”

I did what anyone else would do. I’m like, “I have to go to the bathroom,” and so I furiously texted. I posted on the blog. The blog post was something like…The headline I think was like, “An Honest Beginning from Etsy’s CTO.” It was basically a long apology with an appeal for time at the end. If you read it today, I think the last thing I wrote was like, “If you give me time, I’ll make you proud.”

I was grasping for something. All I had was hope for the future. To give you a sense of the timing, there was our stuff on a truck coming to Brooklyn. I was sleeping on an air mattress. And the day that I posted that blog post was the day that Lehman Brothers collapsed.

Those of you who are following the venture capital world at the time, there was the famous Sequoia deck, Good Times RIP. The end of the Good Times and people are using phrases like, “Nuclear winter for venture funding,” and all that kind of stuff, and Etsy wasn’t profitable yet. Here I was sleeping on an air mattress, writing apologies to the community. The entire financial industry was collapsing across the river and there were just lots and lots of problems.

SL:  Did you ever have a moment of feeling like, “What have I done?”

CD:  A couple months in. Remember, “Comedy equals tragedy plus time.” A couple months in I called someone back in the Bay Area, a good friend, and I said, “Man, I might have really blown this one.” I think what I told him was like, “Well, I’m in it. I don’t want [my career] to end this way.” At that point I realized I just had to dig in.

SL:  You felt like this could have been a career ending move?

CD:  I did. It’s funny. I remember one of the things we do in engineering is something called continuous deployment. We’d gotten to be well known for it. Someone sent a message to me saying, “Yeah, this must be easy. Like you’ve always done it this way.”

We deployed once every three weeks. Every time we deployed, the site broke at that period of time. It was definitely a difficult time. I felt like I just really had to dig in and make it right. To be totally fair ‑‑ I’m telling the technology side of the story ‑‑ the business was always showing really strong numbers.

We managed ‑‑ I think through the generosity of the community and commitment from the community ‑‑ to make it through those times.

When you come in as CTO, everyone’s like, “OK, great. Now we can start building whatever we want.” I remember a board call where one of the board members said, “I think the fact that you guys aren’t able to get things done is becoming a real cultural problem.” I’d been here like three months. They were basically saying, “Hurry up. We’re tired of hearing the site doesn’t work.”

Now I’m running the company.

I think what happened there ‑‑ this may be jumping ahead a little bit ‑‑ a lot of things happened between then and what I think you see Etsy now, where we’re in really good shape. I think what the board was able to see is that it was really dire. All startups have these dire moments, and I just had to dig in and fix it.

No matter whether it’s a technology problem at Etsy or any of the companies that you worked for, no one’s going to applaud you if you come into an easy situation and make it marginally better. I think it’s the really hard stuff where you really learn.

When I thought I’d made a career ending move, I said that because I was afraid. I was like, “Oh my God. I don’t know if I’m gonna be able to fix this.” I think, if you react to fear positively, then really good things can happen.

SL:  If you were the CEO of Etsy then, would you have hired you as the CTO? You’re describing a company that was really dysfunctional technically, and you’ve describe yourself as not the world’s best coder.

CD: That’s a really good point. A really good question.

I was being a little bit self‑deprecating because I think that sometimes one of the problems that startups have ‑‑ one day I’ll probably advise startups full‑time because I’ve learned so much in this world ‑‑ is they over‑engineer things. One of the benefits of not being a very good technologist is that you can only do simple things.

Etsy didn’t need sophisticated algorithms. I’ll give you an example. When I joined Etsy, every time you loaded the home page, you hit the live database for every item on the home page. If you’re an engineer, you’re probably horrified. I was like, “Hey guys, let’s cache the home page.” Suddenly performance went through the roof.

There’s a lot of interesting technical work that was very intricate, but the home page wasn’t loading fast and I know about caching. That’s one of the things you learn working at a place like Yahoo. I’m probably being a little self‑deprecating, because I’ve been through a lot of this stuff, but my lack of sophistication in that sense was probably a benefit.

I just instituted caching. We put in a content delivery network. We started using Akamai. Our performance increased 2 to 10 times over a couple months by doing really boring stuff.

SL:  Let’s talk about Rob a little bit because the  big thing that I know about Rob was that devastating “Inc” story that came out about him. It was really shocking to a lot of people who just knew the company.

I’ve seen a ton of founders in Silicon Valley and worked for one in the past where a lot of the good things about the company and the bad things are all wrapped up in that person. It’s really, really hard when you work for a company like that, because you’re well aware that the company wouldn’t be what it was if it wasn’t for that person’s vision and frequently sense of community and semi‑insanity.

That can also hold companies back. That’s always been my impression of what Rob was like. Do you think that’s a fair estimation?

CD:  The way I think about Rob is it was really Rob’s vision and Rob’s salesmanship that brought me to Etsy. That story I told was not one of those made up stories. I was literally sitting in Rob’s apartment in Red Hook, on the roof. It was that perfect 75 degree day.

Red Hook, if you didn’t know this, is the only place you can look into the Statue of Liberty’s face. Rob and I are sitting on this rooftop and he’s telling me about Etsy. I’m looking at the Statue of Liberty in the face, and it’s this beautiful in New York.

Fundamentally, no matter what happened with Rob, Rob started the company, and Rob sold me on the company. Rob recruited Caterina to the board by basically sending a fan letter to Flickr, saying, “I really love what you guys are doing,” and he had attracted investments.

SL:  What was so compelling about the way he sold the company?

CD:  I think many of the same things that you see in what’s compelling about the company today. I think Rob really saw a world where people are buying and selling from other people, and e‑Commerce is about relationships, just a world where craft was really respected. I think Rob totally got that right.

The challenges that Rob had are not really unique, I think, to any startup founder. It’s just that the company got bigger and bigger and more complex, [and] Rob’s not a career manager. I don’t think he ever really aspired to be one. Over time, I think that some of the scaling issues just made it difficult for him to be successful.

When you think about the name Etsy and you think about what Etsy became, it all came from Rob. The quirkiness in Etsy that I think remains comes from Rob. I have nothing but respect for Rob. I wouldn’t be here if Rob hadn’t started the company.

SL:  Do you think, under different circumstances, with a different co‑founder, with different coaching or mentorship, or whatever that Rob would still be the CEO of Etsy today?

CD:  That’s a really interesting question. I think Fred Wilson actually said this, and it might have been in that “Inc.” article, and I totally agree with him: He described Rob as an artist, not a businessman. Even that’s funny. Think about Rob was able to raise money in 2008 from Accel and get Jim Breyer on the board, who’s the number one VC in the world.

It’s almost unfair to say he’s an artist, not a businessman, although I agree with the general sentiment. That’s just really hard to speculate. I don’t actually know the answer.

SL:  What’s your relationship with Rob like now?

CD:  Rob’s not really working on Etsy anymore. Rob and I don’t really talk about this stuff. Rob’s off doing his thing in Hudson, in New York, Upstate.

SL:  A company that I always frequently compare you guys to is Twitter, because it’s usually a death knell when you have to go through a change and CEO. It can be really disastrous for companies.

They’re very few companies that I’ve covered in 15 years of covering entrepreneurs that have gone through three transitions in CEO over a short period of time and have not died.

Fred Wilson is an investor in both and refers to you both as “weeds” because it’s like nothing has been able to kill these products. The product and community on products have been so strong that all of the things that traditionally kill start‑ups have not killed the company.

I’m curious in your case, having seen it from the inside up close, what was it about Etsy that kept it from getting killed? Did it ever seem like, “This is just going to collapse”?

CD:  My whole first 18 months, it felt that way, but I think there are two different ways to look at it. There’s what was happening externally and what was happening internally. I said this earlier in a different way, and this is something that I think Rob really got right. Etsy is something that people really love and care about.

I think what allowed Etsy to continue going through a lot of the same problems that Twitter had with technical stability, and all that kind of stuff, is that the sellers on Etsy and the community on Etsy is really passionate and there was nothing else like it.

The other thing is ‑‑ and I still think about this a lot ‑‑ there have been a number of start‑ups that have popped up that people say like the Etsy of this, the Etsy of that. None of them have been able to capture that magic that Etsy has. I think the Etsy magic, and the devotion of the community, and the passion really kept it through. That’s externally.

Internally, I believed in what Rob sold me at the time and still believe in it. I was able to do two things. I was able to observe all the mistakes that led to the changes up close, and watch those really closely, and learn from those.

I was also, by the time I was asked to be CEO, I had a long list of things that I wanted to do at Etsy. I had respect for the people who worked at Etsy. I had respect for the culture of Etsy. It wasn’t like a new CEO who comes in, doesn’t understand the company. I had the benefit of all those things.

More than any company I’ve been involved in, I think through all the changes and what happened at Etsy, what Etsy really needed was someone who understood, not someone to come in from the outside and try optimize it, or say like, “Our strategy is social,” or whatever.

About the Author

Sarah Lacy

Sarah Lacy is the Founder and CEO of Chairman Mom and Pando Media. She's been covering technology for nearly 20 years, previously for BusinessWeek, TechCrunch and many other publications. She's the author of "Once You're Lucky; Twice You're Good: The Rebirth of Silicon Valley and the Rise of Web 2.0" (Gotham, 2008); "Brilliant, Crazy, Cocky: How the Top 1% of Entrepreneurs Profit from Global Chaos" (Wiley, 2011) and the forthcoming "A Uterus Is a Feature Not a Bug" (Harper Business, 2017). She lives in San Francisco.

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