Narrator:
Hey BK with Ofer Cohen
Chad Dickerson:
I was recruiting an engineer and he was making a choice between Apple, obviously in Cupertino, California and Etsy, you know, it's hard to recruit against Apple. So I got to know him and I was starting to understand what he was into and he was really into music and hip hop and my closing line that got him over the line to come to Etsy was how much hip hop are you going to see in Cupertino, like run to Brooklyn.
Ofer Cohen:
On today's episode of Hey BK I talk to Chad Dickerson, former CEO of Etsy, the ecommerce site of handcrafted goods that started in Brooklyn and became a multibillion dollar success. Chad now has an executive coaching career and he's teaching at Cornell Tech, he got his start in silicon valley but grew up in North Carolina. In our conversation you'll hear that after just 11 years, Chad has found, his place in Brooklyn and considers it a real home.
Chad Dickerson:
I lived in the south until I was 23. So like that was pretty much all I knew. And, I didn't visit New York until I was 26. So, you know, I grew up in eastern North Carolina in a place called Greenville and my kind of early childhood, still very farm and oriented. Um, both sets of my grandparents were tobacco farmers, like livestock, pig farmers. And so that was kind of the world that I was used to. And, my maternal grandfather, was unable to read or write, you know, my grandfather would get his birthday card and I at, you know, from age five until much later, like I would read his birthday card
Ofer Cohen:
That's incredible
Chad Dickerson:
That really made an impression on me. And eventually, you know, I ended up going to Duke, scholarship kid and I actually, I majored in English and graduated with honors focused on Shakespeare. So I just never forgot just how important reading is. And it also, I think, growing up in that environment, really gave me kind of a deep appreciation for, can't think of a better term than just like regular people. And so since then, obviously, I mean you know, the guy, I rung the bell at Nasdaq and like took a company public and you know, met famous people and all that stuff. But you know, I'll never forget kind of where I came from. And you know, when I left at Etsy, one of the things that I was proudest of is that, you know, the people who cleaned the toilets and the security guards, and those people, you know, told me as I was leaving that they really appreciated, you know, how I related to them.
Ofer Cohen:
So you spent 10 years in California? In between, the south and Brooklyn
Chad Dickerson:
Yeah at that time in the bay area from 98 to 2008, I went through the whole ".com" boom and bust. I would say what's in some ways, like the most formative time of my life, like I was 3000 miles away from where I grew up in California in great ways and negative ways. It's like living in a different country and, I just learned a lot there.
Ofer Cohen:
You worked for Yahoo.
Chad Dickerson:
I worked for Yahoo. I went out there in 98 to be the CTO at salon.com, which was really an online innovator at the time. And, you know, I went, you know, this kid who grew up in the south, I went from that to, you know, being in a newsroom with people who worked at rolling stone in the 70s and you know, just sort of crazy lefty San Francisco. I say that with a lot of affection.
Ofer Cohen:
And then again, your name was Chad so they, kind of embraced you.
Chad Dickerson:
Well, they thought that, a really close friend of mine out there said, when I joined, you know, I had just worked at CNN, I'd like graduated from Duke. My name was Chad and I came from the south. He said he thought that I'd come from some kind of aristocratic southern family and we laugh about it because as he got to know me he got to know what kind of mind and personal stories I had.
Ofer Cohen:
Though Chad had a successful career at Yahoo and was living the good life on the west coast. A friend who had invested in Etsy convinced him to interview at the Funky Brooklyn based startup.
Chad Dickerson:
So I finally went out to Brooklyn in July, 2008 and I emailed a couple of my friends and said, you know, I'm going out to Brooklyn to talk to Etsy. I'm never going to move to Brooklyn. I'm like a California guy now. So I totally fell in love with Etsy. I met Rob Kalin, the founder. I went from kind of not being that interested in it, just totally entranced. And a big part of it was Brooklyn. Brooklyn in 2008 was a really exciting time. And so my wife and I came back to California and we'd just been married for like a year and we decided to move to New York.
Ofer Cohen:
That's incredible. You know, you took a shot and look this interview that he didn't even think.
Chad Dickerson:
Yeah. And like, I mean it's easy to sit here in 2019 and Etsy is probably, I haven't looked lately, but probably like an $8 billion company, right? It was not an $8 billion company. You know, Etsy was all about handmade and the office was handmade. I mean Rob the founder, uh, I think he actually did the plumbing and the office. Um, cause I remember one day early in my tenure there, like there was like a clog in the sink and rob the founder went and got his tools and said, okay, like I know how to fix this because I put it together. So the office itself was handmade and uh, and very, I mean people talk about startups being scrappy. Like there was not much going on in Downtown Brooklyn at that time. You know, there was one bathroom for the whole company, like one toilet. Um, and so if anyone had to go, like, you just had to wait and there was a sign on the toilet paper that said, you know, if the toilet paper runs out, go buy some. So if you're the lucky soul to go in there and you know, the toilet paper runs out, you had to go, you know, somewhere in that area in Downtown Brooklyn, you could probably buy toilet paper in a hundred places around there now. But you had to go like on a trip just to like find a place.
Ofer Cohen:
Yeah. so when you, when you came, how many employees?
Chad Dickerson:
I think it was about 40 employees. Um, it was like a really small office and you know, companies, startups have lunches and such. And when we had, our weekly lunch, everyone could sit around a table. So, you know, when I joined it was three years old, but it was still incredibly, incredibly small. And, it's one of those things you learn in life. I remember walking in and feeling like I was joining late because I was like employee number, I don't know, 45.
Ofer Cohen:
Chad to help build Etsy for nine years and felt like a founder. Eventually Etsy became the biggest success story for tech in Brooklyn. He started as a CTO and in 2011 became CEO until his departure two years ago. At the beginning he faced typical startup challenges, like faulty technology. Not to mention this was the midst of the great recession.
Chad Dickerson:
That technology was in really rough shape. Like a lot of startups, like the company was scaling, and the team was building as fast as they could, but you know, you don't always build perfect software in that case.
Ofer Cohen:
Was it harder to at that point and to recruit tech talent, you know, to work in that space in Brooklyn
Chad Dickerson:
It was somewhat difficult. So, you know, I had a couple of former CTO's come in and do some consulting work for me, the kind of Silicon Valley folks to kind of look at the tech stack and everything. And one of the things that they wrote up in their report was that they believed it would be extremely difficult, if not impossible to build a first rate technology team in New York. Right. And so Brooklyn at the time, especially if you know the geography of Brooklyn, that space was in that neighborhood was not, you know, full of coffee shops. We had terrible Internet service. Like the Internet was going out constantly when I was there. And I think part of it was, you know, there were two high rises being built, one on either side. And just so the building for my first year, the building was shaking pretty much the whole time we were there and there were two pile drivers just like boom, boom. And so it's kind of an unstable building. There are two huge skyscrapers there now, but the Internet went out all the time. And one of my first task, a CTO, you think you're going to come in and be like really strategic and all this stuff is, I think I went down to the Verizon store and bought a bunch of, you know, wireless Internet cards so that developers could keep working. You know, I had just come over from the west coast where I had to fine career and you know, could have done a lot of things there. I stepped into Etsy, the technology was in worse shape than I thought. I honestly, I call it a couple of friends back on the west coast and it's like, oh, I think I might've made a career ending mistake by joining Etsy. It turned out to be the opposite. But, um, yeah, Lehman brothers crashed. Like I really felt like I had come, to the east coast in general, absolutely the wrong time. And fortunately I think this is kind of an under appreciated aspect of Etsy. Etsy is not, and never has been a hugely capital intensive business. So Etsy even in 2008 was running pretty close to break even, especially by today's standards. And I think in 2009 or so we did break even during one period. So it's like a very good business and, there was no need during that period to raise venture capital. Um, in 2008 and, you know, it turns out that a downturn is also a great time to build a company.
Ofer Cohen:
Chad describes what felt like an uphill battle trying to recruit talent to build a major tech company in Brooklyn. So he got creative.
Chad Dickerson:
What I learned is I learned how to pitch Etsy really well. I hired some of my former colleagues on the west coast and convinced them to move to New York.
Ofer Cohen:
How did you do that? You're not even sure if you made the right choice?
Chad Dickerson:
Well, interestingly, and it took me a little while to learn this. I ask myself like, why, why did I come and obviously Etsy, a great company to work for, really interesting, but I would say a huge, huge part of it was New York. Like I wanted to live a more exciting life and you know, like I said, I got a degree in English with a focus on Shakespeare. So I was interested in things like theater and art. And even in, in 2008 you could see the bay area in San Francisco started to become like too tech focused and you know, the arts getting squeezed out and that kind of thing. So, um, it was really as much a lifestyle decision as anything. And so I'll give you an example of like I was recruiting an engineer who, um, was graduating from Carnegie Mellon and he was uh, making a choice between Apple obviously in Cupertino, California and Etsy. And uh, you know, it's hard to recruit against Apple, like everyone's using Apple products and everything. So I got to know him and I was starting to understand what he was into and he was really into music and hip hop and my closing line that got him over the line to come to Etsy was how much hip hop are you going to see in Cupertino, like run to Brooklyn? And that was it. And I use some version of that pitch 100,000 times later I'd find out what someone liked and New York has everything.
Ofer Cohen:
That's amazing. From my experience, there's a component of if you're a real entrepreneur and if the bay area is already established to do a tech company in Brooklyn feels like even more entrepreneurial.
Chad Dickerson:
Absolutely. And that really kind of counterintuitive thing about New York tech is that like New York is, you know, 8 million people, largest city in the United States. But the tech community is incredibly intimate and you know, everyone knows each other. And it's also really, diverse in terms of industries. So right when I was in the bay area, I knew a lot of engineers, a lot of product managers, a lot of people who worked at tech companies. But in in New York, I know a lot of journalists, a lot of attorneys, a lot of artists, a lot of business people of all stripes. And so it's a much like broader view of business and I think it's much more connected to reality. And I think it's also much more connected to just just sort of the global world that we live in because New York in some ways is almost like a physical representation of the Internet. Like you have this grid of streets and you know, you can practically go to different countries like every day just walking in different neighborhoods, going to different restaurants. My name is Chad. I got into a lyft once and the driver was like smiling and laughing and he said, Chad, I am from the country of Chad. And, uh, we just had a great conversation.
Ofer Cohen:
But I think the overall notion in our industry that it's still, we still need to pitch the idea of tech, especially big tech to establish their headquarters offices, you know, studios, whatever in Brooklyn. Why is that?
Chad Dickerson:
I actually think there's less need to pitch it every day. And I would say five years ago I felt more that way, but a few things have happened. I think, you know, one is a number of companies that were started in New York have gone public and hit the public markets. And I think that's a big moment because it creates liquidity for people who live here and it also creates kind of the next generation of investors. And so there was a time when, you know, the DoubleClick folks were kind of the big story, but now you could say like Etsy and Mongo DB and Yext and like all sorts of companies. So that happened. Um, you know, something I'm involved in Cornell Tech. Um, the University on Roosevelt Island is now been established and I think really amazing tech focused academic institutions are a big part of the equation. This sounds crazy if you live in New York, but I would, five or so years ago you could start to pitch people that it's less expensive to live in New York than it is in San Francisco. Like those, the monthly rent lines crossed at some point. Um, and I think, there's also been a backlash against, uh, the tech industry and I think there is a desire to kind of, you know, kind of do something that's more connected to the world and isn't kind of in the kind of ivory tower of Silicon Valley. And I think New York is kind of the perfect place for that. So I think New York has become, you know, really easy to pitch. If there was ever any question that this cycle was going to happen in a very Broadway in New York, I think that question is already answered. And these things have a way of just snowballing and continuing. So I think, uh, what I like to say is New York is not the next silicon valley. New York is the next New York, right? The tech ecosystem I think is, is very much maturing right now.
Ofer Cohen:
I'm assuming there's a notion of, you know, Brooklyn, as part of New York City, but Brooklyn enables you to have different kinds of neighborhoods and different kinds of experiences and the pricing points and lifestyles and which could be very attractive for different people and different kinds of sides of the tech spectrum.
Chad Dickerson:
Absolutely. And I think, you know, I think that in some ways our eras and really every era has defined by kind of like a search for meaning and connection. And one of the things that I've noticed in the tech community in New York is it's very, connected to the civic life of the city. And so just using me as an example, when I was CEO at Etsy, Etsy was obviously a big international company, public company based in Dumbo, but I was also on the Dumbo Business Improvement District Board. And that was really important to me to be, you know, Etsy was a business, but also front street pizza was a business and, there are businesses all around us and so I spent time with the local business owners, in that context because I was one of their peers and I'm still on the board at Saint Anne's warehouse.
Ofer Cohen:
Chad is working closely with founders and chief executives as a coach. He received the same kind coaching when he became CEO of Etsy and is sharing his experience going from a small startup to a public company. Meanwhile, Chad is finding himself immerse in a lifestyle of Brooklyn. He and his family have made at home in Carroll Gardens where a CEO of a major company, just another regular guy.
Chad Dickerson:
One of the things that I really love about New York is that no matter how big you are in any industry, the capacity for people not to care is really high. When I was running at Etsy, obviously, you know a big company here in New York. And when people cared about, like my, one of my neighbors a long time a New Yorker and native came to me and said, so, uh, like you work on the Internet? And I was like, yeah. He's like, can you help me fix my Wifi? So like it's like I don't care.
Ofer Cohen:
Did you?
Chad Dickerson:
I did. Yeah, I know how to, if anyone out there needs Wifi help, I'm your man. Something that was surprising to me now, having lived in New York for 11 years is New York is fast and people talk quickly and like all those things. But um, it is the friendliest city in the world as far as I'm concerned
Ofer Cohen:
Because you could actually talk, you can start a conversation with anyone anywhere.
Chad Dickerson:
Yeah. The thing I liked the most about it too is you get to know the various merchants around the neighborhood too. So my son who's seven years old, takes piano lessons at the place called rock school on Smith Street. It used to be called musicians general store. And, uh, you know, Mingo, the owner is been in the neighborhood since like the late fifties. And so when my son is in his piano lesson, I talked to Mingo about music and the neighborhood and you know, when he used to play in battle of the bands, those places are really kind of, not just kind of service providers or stores, but they're also social institutions. And, you know, I like it so much. I actually started taking piano lessons about a month ago. Almost like, you know, my, my son's grandparents are in North Carolina, but he's got several grandparents on the block and that's just really, really nice. And so, yeah, I feel like, um, he, and we have a community that, uh, in this big city of 8 million people that's really, really, really intimate. You would see this maybe a little in San Francisco, but not, not as much in New York. Like I'm walking around anywhere and I just like run into people because there's very much a walking culture in New York. And so I feel like it's so much easier to kind of stay in touch with people. Like most of us don't spend much time in cars and, that kind of like street life in the civic life of New York, really encourages a lot of chance interactions. I'm still all 11 years in incredibly surprised at how intimate a city of 8 million people can be. You know, my wife and I kind of have a joke, like sometimes we want to go out to a bar and have a drink and talk to each other, but we kind of say how long before we run into someone that, you know, and that's a beautiful thing.
Ofer Cohen:
But that is cool, and it's been only in 11 years.
Chad Dickerson:
I mean, yeah, it's just such a social environment. And a friend of mine who lived here for a while before I moved here said, you know, one of the great things about New York is like you'd go to a bar or something, like the person next to you to start starts talking to you. Right. And you know, I haven't spent a lot of time in the bay area recently, but if you go to a bar in San Francisco, you kind of, everybody sits and looks at their phones until they're friends arrive and then they socialize. But it's all very like, yeah.
Ofer Cohen:
So it sounds to me like you, you, you actually wouldn't want to do it anywhere else, but in Brooklyn, right?
Chad Dickerson:
Definitely not, I mean, I was talking to a friend who's been in New York for probably 30 years and we were talking about like New York has kind of, almost like an addictive quality, like the things that you like are things that you just can't get anywhere else. And so I find even on the kind of a basic level, you know, I like track my steps like everyone else. And I find that when I go to another city, like my step count goes way, way down. And in New York, you, you're walking like five, six miles a day and without even noticing, right. And while you're walking, you're running into your neighbors and you know, walking into shops. And that kind of thing. And so I think that social network and that social environment, um, is something that you just really can't replicate anywhere else or I haven't seen anywhere else you can do that. And maybe one day I'll start a company again. Uh, but, I'm really enjoying this and as I mentioned, I'm, taking piano lessons and so I decided to carve out a little time to do something creative. And, uh, as a CEO, you can't take piano lessons.
Ofer Cohen:
You already told us about the piano lessons, but I do ask at the end of every show, uh, to tell me something that nobody knows about you.
Chad Dickerson:
Oh Gosh. Now I'm worried
Ofer Cohen:
Yeah, the piano was like a perfect one.
Chad Dickerson:
I'm gonna have to think for a moment on this. Gosh, I guess I would just talk too much about myself in public. Um, well, one thing that may be surprising, I'm a person who's like very pro gun control and that sort of thing. But I grew up in the south and grew up in a culture where you were taught to like to shoot weapons. And I'm, if you were to like give me a rifle and a target, I'm like a really good shot. I don't own any guns. I'm very much pro gun control, I know guns well. And you know, I've shot a variety of them and that's just part of the part of the culture that I grew up in. And you know, at heart I'm basically a pacifist. So the idea that like, I'm a good, a good shot, at a target with a weapon is probably a little surprising.
Ofer Cohen:
I can totally see that. Thank you Chad.
Chad Dickerson:
Thank you Ofer