Deep Dive with Chad Dickerson

Speaker 1: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, Co- founder and CEO of Bolster, and I'm here today with my friend Chad Dickerson. Chad is a CEO Coach, and he has a provocatively named firm, Strong Back Open Heart, which I'll ask about in a few minutes. Chad was the former CEO, and before that CTO, of Etsy as well. So Chad, welcome to the Daily Bolster.

Chad Dickerson: It's great to be here, Matt.

Matt Blumberg: So I love doing these Friday In Deep With interviews because we really get a chance to understand the arc of someone's career and things that they've learned along the way, which I just think puts the CEO job in great context for people. So when I think about your career, the point where I met you, you were CTO of Etsy, about to become CEO of Etsy, but you had actually been in technology for a while before that. And if I remember correctly, I think you were a reporter.

Chad Dickerson: I was a columnist.

Matt Blumberg: Ah, yeah.

Chad Dickerson: Yeah, I was.

Matt Blumberg: Before that, and then worked on the West Coast in a bunch of early technology companies around news and media. So would love to hear how you transitioned into engineering from journalism and the first couple of jobs you had in technology.

Chad Dickerson: In a lot of ways I got really lucky in being in the right place at the right time. So I grew up in North Carolina and as a kid, I always read the newspaper, starting at five years old. And the newspaper I read was The News& Observer, in Raleigh, North Carolina, which still exists. But in the nineties, it was one of the last family owned newspapers before all the consolidation in the newspaper industry. So in my child's mind, I thought, one day, if I'm successful in life, I'll get to work at The News& Observer. I'd seen All the President's Men and I loved this idea of the newsroom and people dashing around and all that kind of stuff. But the reality was a little different. I went to Duke and I got an undergraduate degree in English literature, focused on Shakespeare, and I graduated-

Matt Blumberg: Like every good CTO, by the way.

Chad Dickerson: Exactly, like every good CTO. And there weren't a lot of people beating down my door in 1993 to hire me as a English major. So actually, much to my parents' chagrin, after they had spent all this money for me to go to Duke and everything, I was actually delivering pizza to pay the rent. And I also had a second job and I got a clerical job at The News& Observer, which is my dream workplace. But where it connects to technology is I was doing clerical work, like data entry and filing, in a room where they were building some of the first websites on the internet. So The News& Observer was, I think either the first or the second daily newspaper on the web in the United States. The San Jose Mercury News might've been slightly ahead. And so I did what actually became a habit of mine later in my career, I did my job and I did it well and it delivered a high quality, but I just walked around and talked to people and asked questions, and before I knew it, one of the people I worked with in that room where I was filing said, " Hey, do you want to learn SQL?" And over about a year of me staying late in the office, they had an internet connection, which was really novel at that time, I taught myself how to do SQL and then they taught me how to write backend web applications. And I would say about a year and a half, it was almost like night school. I was like an amateur UNIX systems administrator and a programmer, and I was doing real programming work for the newspaper. And so that's how I got started. I didn't have permission to do most of the things I was doing, but the contacts I made there really led to everything else that came later.

Matt Blumberg: Is that what propelled you to the West Coast? " Hey, I'm in technology. It's the beginning of the internet."

Chad Dickerson: Well, I was coding probably late 1993, early 1994. I remember being at work when people were talking about Mosaic, the first browser, or the first usable browser coming out. One of my colleagues who taught me how to code interviewed for a job in Atlanta as the webmaster for the Atlanta newspaper, and he decided he didn't want to move to Atlanta and he told them they should talk to me. So I had a brief tour in Atlanta. I went down to The Atlanta Journal- Constitution, interviewed, and they hired me at age 23 with six or nine months of experience to run their web operation. And that was my first legitimate job where I entered as a real technologist. And then after nine months there, I got a call from CNN, which was just down the street, and that was my big dream job. I used to watch CNN a lot when I was a kid and loved news. So I worked there for probably three years and worked on cnn. com in the very earliest days, which was the largest news site on the web at the time. And then helped build CNN and Sports Illustrated, which was the first joint venture between Turner Broadcasting and Time Warner, and it's actually where I learned what a corporate merger looks like.

Matt Blumberg: What did it look like?

Chad Dickerson: It looked like me having, I think I had seven bosses in nine weeks, and comically, one of my last of the nine or seven bosses was an Anderson consultant. And in our first one- on- one, he asked me if I could help him get paid, he didn't know how to navigate the finance system. So it was like, I don't know if you've ever read Catch 22, the novel, it was a corporate version of the absurd feeling that you get about the military reading Catch 22. But then the thing that took me to the West Coast was I was a big reader of Salon, I was literary in my interest in that sort of thing, and I noticed they were hiring a VP of technology, CTO, and I remember I wrote a cover letter to them, this is like 1998, and I think the opening line to my cover letter was, " I am the only person who will apply for this job who has read all of Shakespeare's plays and sonnets," and I had an interview.

Matt Blumberg: You got to prove out the value of that English degree.

Chad Dickerson: And so I went there, and Salon was a really amazing, exciting place. We actually went public in 1999 as part of the . com boom, so I was right in the white- hot center of that. And just as a trivia point, our IPO is a Dutch auction, and the bank that took us public, WR Hambrecht, was testing out the Dutch auction because they had bigger ideas for it and the next company to go public under the Dutch auction and WR Hambrecht was Google.

Matt Blumberg: Google. Yeah.

Chad Dickerson: So I got to see the mechanics of that. Our IPO did not go as well as Google's IPO.

Matt Blumberg: Is Salon still independent?

Chad Dickerson: Salon is independent. I guess, what does independent mean? But I lost the lineage of it somewhere, but it still exists.

Matt Blumberg: Still exists.

Chad Dickerson: Yes.

Matt Blumberg: And then you did a tour of duty at Yahoo! for a few years?

Chad Dickerson: Yes.

Matt Blumberg: inaudible.

Chad Dickerson: Yeah. And just as a quick side note, just before Yahoo!, I was at InfoWorld, the IDG publication, and so I wrote a column. That's where I was a columnist for four and a half years. I wrote a weekly column called CTO Connection for CTOs. And four and a half years weekly column, I wrote 200 plus columns on deadline, just like everyone who worked there, and that was an amazing experience. But that was my last media job and the first one where I actually wrote.

Matt Blumberg: Were you also on the technology team there? And the writing was a side gig?

Chad Dickerson: I was the CTO. So the whole idea was that I would do the job and also write about the job, and it's a little bit harder than you think because one time I wrote about something that vaguely alluded to a performance issue on my team, and the whole team was upset with me. And one time I wrote something that was really vague about struggling with a particular vendor, without naming the vendor, and the CEO of the vendor wrote to me and said, " I know that was us, and we were really upset." So it was most of the time it worked, but people got really upset with me at times. I wrote a really critical thing about Lotus Notes, and we heard from IBM on that, they were a big advertiser, but we did have editorial independence and I didn't get too much coming down on me for all that.

Matt Blumberg: Yeah, that's interesting. I didn't realize you were doing both. So you were pursuing your original dream, while pursuing your current vocation.

Chad Dickerson: And it was fun. I remember once, 9/ 11 happened during that period, and so I had a ton, I knew a lot of Fortune 100 CTOs who were reading my column and New York needed help and so I helped organize, we had what we called a CTO network, and I helped organize some relief work and technology help post 9/ 11. So it was an amazing job and I got to network. That was one of my best networking jobs, honestly. I remember I was shooting pool and drinking beers with Tony Scott, who was the CTO of General Motors at the time, and even though InfoWorld was really influential, I was running a team of probably 20 and I'm hanging out with the CTO of General Motors just talking shop.

Matt Blumberg: What'd you learn from him?

Chad Dickerson: I learned that, and from Tony and many other people I worked with, is that in a technology organization, especially at scale, a lot of the problems are culture and people. And I still believe that to be true. I think we tend to overfocus on technology, especially in engineering circles, but the problems and challenges I've had with people have been really consistent regardless of how technology changes.

Matt Blumberg: So you were then at Yahoo! for a few years, and you must've had a pretty big team at Yahoo!. You were there at peak Yahoo! years, right?

Chad Dickerson: Yeah, I joined in 2005, and I was part of a wave that, at the time, I think some journalists called it the Flickrisation of Yahoo!, because Flickr had just been acquired, and for people out there who don't remember Flickr, maybe a few, it's a photo sharing site started by Stewart Butterfield, who later went on to start Slack, and Caterina Fake, his then wife, and Caterina and I were colleagues at Salon. And so both of them were like magnets for talent at that time and Flickr was one of the first social apps with tagging and sharing and commenting and all that sort of thing. So I was there from 2005 to 2008 and that spanned that era, but also the period where Microsoft came in and made a hostile offer to buy Yahoo, and I got to see all of that up close. But mostly what I was working on was what I would call the innovation teams at Yahoo!. So there was a group called Brickhouse where we had our own office in San Francisco, the main office down in Sunnyvale, and we had freedom to try to build new products without the constraints of the main Yahoo! organization. And I learned a ton about what it means to be an innovation team that works apart from the main line. Number one, we didn't make any revenue and the people who did make revenue running things like Yahoo! Mail, I think resented us in a lot of ways. And at the time, there was a little bit of a rivalry in that way but as I've gotten more mature as a business person, I totally understand why they resented us. Because we were getting a lot of-

Matt Blumberg: You were getting all the inaudible.

Chad Dickerson: Buzz. And we got to play around with Ruby on Rails, which was new at the time, and they had to continue with PHP and all the standard stuff. So I could talk a lot about that.

Matt Blumberg: Obviously much, much smaller scale, but we had a lab Steam at Return Path that was the midsize company version of that, and the thing that we tried to do, I'm not sure how successful we were, but we tried to rotate people through that team so that people felt like they'd have an opportunity to be on that team for a tour of duty if they wanted.

Chad Dickerson: Yeah. That's smart. I think in general what I learned is that, and I haven't seen it in action in other places, but I think if the core problem that a company's trying to solve is trying to innovate more, I think that if you put the innovation off to the side, then I think it hurts the company's ability to innovate at the core, because it's almost outsourced to someone else. And so my philosophy now is that you have to try to innovate around your core products. It doesn't mean that everyone can be working on innovation, but at some point you have to innovate in your core.

Matt Blumberg: So what brought you back to the East Coast to become Etsy's CTO?

Chad Dickerson: Yeah, part of it was honestly looking back like Yahoo!'s dysfunction. And I was a very loyal soldier and I had a really great experience at Yahoo!. I got to know Jerry and David, the founders, and one of my biggest memories is we had a top 150 people at Yahoo! met once, and Jerry had put that together, and it was like an offsite, and they brought in a special guest. This was in 2007, and we were all wondering who it was, and it turned out to be Steve Jobs. So I was sitting there amongst this top 150 people at Yahoo!, listening in a private setting to Jerry doing a fireside chat with Steve and asking him for advice, and Steve not holding back.

Matt Blumberg: He was not known for holding back.

Chad Dickerson: No, he was not holding back. He did it in I think a very Steve Jobs sort of way. He was very positive and talking about all the great things Yahoo! had done, but he said, " You're doing too many things, and Yahoo! means too many things, and you have to pick a smaller number of things and do them really well." So that was really exciting. But what brought me out to the East Coast, when Microsoft made that offer everything went haywire inside the company because there was a visceral reaction against the evil company from Redmond coming down and acquiring Yahoo!. And this is another big lesson I think I learned in business, I think Yahoo! overreacted. And instead of looking at the offer on its merits, they began fighting it off and put in a poison pill. And what happened with the poison pill specifically is basically, if a merger happened and your job was eliminated, then all of your stock would vest, no matter what the window on that vesting was. And you would get a big bonus. So there were people inside the company out of self- interest that was meant to make the deal more expensive. They were kind of like, " Hey, I can walk away." And so loyalists, I wasn't really one of them, but even the loyalists were starting to question why they should stick around. But Caterina Fake actually was an angel investor in Etsy, what a great thing to be. And we had been friends from Salon and working together at Yahoo!, and she told me that the Etsy engineering was not in good shape and it would be really helpful if I would talk to the founders. And so I put that off for weeks and months. I had a very busy life, and traveling to New York wasn't on my list of things to do. I was renovating a house in Berkeley, I'd just gotten married. And so it probably took three months to make that happen. And so I came out, and originally it wasn't about me interviewing for the CTO job, but by the time it happened, they asked me if I would interview for the CTO job. And so my wife Nancy and I went out, I still have an email that I sent to some friends that I said, " Hey, I'm going to Brooklyn and it's going to be a vacation interview. I'm just going to have a good time in New York and see what's up." And Nancy and I had this magical weekend in New York where we were walking through Central Park and we heard some music and it was not humid in July, and we walked in on a Bon Jovi show and everyone was having a good time and we had great food, and the city was just magical. So we interviewed at Etsy, I could really see how I could help. Everything was really clicking. And on the way back, on the flight back, we had been here maybe five days, we said, " If this comes through, let's do it." And so it did come through. I remember calling the contractors who were working in our house and telling them not to lay down the expensive style in the kitchen, to get cheaper tile, because we were going to make our house into a rental, and there's still a lot of work to be done, but we decided to move to New York.

Matt Blumberg: So you come to New York, you're CEO of Etsy, not very long, couple years, a year and a half.

Chad Dickerson: Almost three.

Matt Blumberg: Oh, three years. Okay.

Chad Dickerson: Yeah, it was long.

Matt Blumberg: And then you get tapped to replace Rob as the founder, as the CEO. How did that come about? What was your reaction to that?

Chad Dickerson: Yeah, well, Etsy has a complicated history for such a outwardly friendly company. So when I joined, Rob Kalin, the founder, was CEO, and Maria Thomas was COO. And so when it was announced that I was joining, Maria became CEO, and Rob became Chief Creative Officer, and this was all engineered by Rob as a founder. And so I worked for Maria, and I think it's safe to say even in a public setting, Maria and Rob are extremely different people. I think they would both agree. So Rob, insanely creative, brilliant. Maria, very business- like, has an MBA, and both with amazing qualities. And so I think Maria as CEO drove the company to break even, I think, which is an amazing thing to do for an early stage internet company. And I think Rob decided as the founder and someone selling the board, that he wanted to come back. And so Rob came back in late 2009 and Maria stepped aside, but I think Maria did a great job and deserves to be commended. And so Rob came back and the company had grown. When I joined Etsy, the whole company was 40 people, and by the time Rob had come back, it was about 175 people. And I had basically rebuilt the engineering team and taken the engineering team from one that wasn't functioning very well to a really talented team. I recruited some of the best people from the West Coast. The language that we used on the platform was PHP, actually recruited Rasmus Lerdorf who invented PHP as an advisor, and eventually got him to join as an engineer. So that kind of talent, and John Allspaw who I would say popularized and almost invented DevOps. And so we had this amazing team. And so I think Rob, as the company was getting better, Rob wasn't... Rob's first job was Etsy, and so I think Rob as a leader wasn't scaling, he maybe wasn't the right person at that scale. Which is something I learned later, which we could talk about about myself. And so the board appointed me as CEO in the summer of 2011. And so by then the company was, I would guess about, I don't know, 250 people maybe doing 30 million in revenue, 40 million revenue. And the thing I remember the most is how everything changed overnight. Because when you look at it, like in an org chart, going from CTO to CEO is like one step up. But what I started to understand is it was more like an order of magnitude step up, and running a functional team, while it's really valuable experience and has its own set of stresses, like being responsible for the whole ecosystem of the company, I started to understand that even though I think I was a very responsible CTO, I could always, in the back of my mind, say, " If marketing would just get their act together, or if BD would do the right deals," whatever. But to be sitting in the CEO seat, as you know, any problem in the company, you can blame yourself.

Matt Blumberg: That was interesting. That's not necessarily the normal transition that the board looks for, right? Placing the founder with a CEO at that scale, you'd think, oh, they're going to hire from the outside. Not hiring from the outside, you would think, oh, they're going to appoint the obvious number two person, not necessarily CTO, I would guess that's the minority of the internal CEO promotes.

Chad Dickerson: Yeah, without a doubt. And a lot of people probably don't know this story because I don't think it's probably been discussed publicly, but Adam Freed had come in as COO when Rob was CEO, and Adam had built early teams at Google, I think he was employee number two or 300 at Google, he spoke nine languages, Harvard MBA. Adam's just an amazing business person. He went on to be CEO of Teachers Pay Teachers. And there was this moment where I think the board wanted to make a change, and Adam was, without a doubt, the textbook. He was the COO, he had an MBA, he had scaled teams at Google, he checked all the boxes, but I'll never forget Adam, somewhere along the way, when the board approached him, and I think they did approach him, Adam said that he didn't want to do it, he didn't think he was the right person for Etsy, but that he would remain at COO and he would work for me. And he thought that I was the right person. And so I owe Adam a lot. I thought that that was, in a world of naked ambition and people positioning themselves, I was blown away by that. And so Adam and his partner eventually started a family not long after that, so I think Adam left about a year later. It was completely friendly and amicable. I'll never forget, he announced that he was leaving and he knew Kara Swisher, and Kara Swisher called, and I remember Kara Swisher was on speakerphone with Adam and me, and she was like, " Come on, Adam. Everyone says they're going to spend time with their family. You're not going to spend time with your family. What's the truth?" And we were like, " He's going to spend more time with his family. That's actually true." And that's actually what happened. So I think honestly, the board was surprised. I think they were surprised by Adam's reaction. But after that they said, " Okay, you're our guy," and I remember when Fred Wilson made the call and he said, " Good luck," so that was 2011.

Matt Blumberg: And then you had an amazing journey, scaling that company from probably a couple of hundred people to eight, 900 by the time you left?

Chad Dickerson: I think it was probably about 1100.

Matt Blumberg: 1100. Taking it public, first time CEO.

Chad Dickerson: Taking it public. And I think the GMV 10x, and revenue I think 14x, our take rate went up during that period, that's why the revenue outpaced the GMV.

Matt Blumberg: And scaled the brand too. Etsy, still, today, is a very distinct and beloved brand.

Chad Dickerson: Yeah, and I think it's got a very long future ahead of it. The nature of Etsy, there's nothing else like it, and you buy merchandise on Etsy that you can't find anywhere else. And that was always the number one reason, when we surveyed buyers, why do you shop on Etsy? And they say, " To find things I can't find anywhere else." And so even with Amazon coming after Etsy, so I also got to experience that, Amazon launching a direct competitor right before our IPO.

Matt Blumberg: No, I remember that because you and I were in the CEO forum together then, and that was the emergency session one day.

Chad Dickerson: Yeah, and I knew that was a possibility but when it happens to you, we're preparing for our IPO, you can imagine going into Wall Street investors and they're like, " Are you worried about Amazon?" And you can legitimately say no, and they're like, " Yeah, right." There's always like, we are worried about Amazon. So I saw that, and as you know, building an executive team as a company's growing is really hard. So I had to iterate a couple of times on the executive team and how that worked, but I learned a lot about it. And eventually, as you and I have talked about many times, my time was up. And so after two years as a public company, I was replaced. And what I was saying earlier about a CEO not scaling into a certain stage, I think looking back, in the benefit of hindsight, I wasn't right for that stage. So I learned a lot from that experience too.

Matt Blumberg: When you think back on the years of running Etsy, what are you most proud of and what's the do- over you wish you had?

Chad Dickerson: Yeah, I'm most proud of, I think it was just a good company on every level. So when I left, or when I was asked to leave, I remember thinking, and even now it's a little bit frustrating. We had a net promoter score for buyers, I think that was around 80, which was equal to Apple and Amazon, my Glassdoor rating was like 98%. Sellers loved us. Our retention rate was 90 plus percent. It was just really amazing. The only people I didn't make happy were investors. And so I'm really proud that the employee satisfaction was so high, the customer satisfaction was so high. But I think that relates to the second question, the do- over, I'll give you a few do- overs. I think that I really believed that the pricing in the marketplace was a feature and not a bug, so we charged 3. 5% per transaction, which was really, really low compared to other marketplaces. And looking back, I think that constrained our ability to spend money on marketing and to take risk on marketing, and so I think had we raised the fee from 3. 5% to 5%.

Matt Blumberg: Which still would've been low.

Chad Dickerson: It still would've been low, we would've had a lot more money to spend on marketing and experiment with. And so Josh Silverman who took over after me, that's one of the first things I think he did, was raise the prices. And so I think one of the things I do in my coaching, which we'll probably talk about, is lead people through various scenarios. And one of the exercises I've done with people is an exercise you've probably heard of called Fire Yourself. If you got fired today and a new person came in, what would they do? What opportunities would they see and what changes would they make? And it's a challenge to challenge yourself to make those yourself, so you don't have to get fired. So I think, I don't know if I did the Fire Yourself exercise, but I think, had I done that, it would've been raise the prices, like the SAT. Not to gouge, but I think it was 3. 5% to 5% was a really almost a simple, fair, even for just inflation and that sort of thing. And I think related to that, and this might be the most useful for people who are thinking about being a CEO more than CEOs, obviously I came from the technology and product side, so I was CEO for six years. I'd say the early part of my time as CEO, there was a lot of product development that needed to be done. And when I left, 50% of our revenue was from services that didn't exist when I started, so we built a lot of revenue producing products during that period. But I leaned really hard on product and engineering, which really worked during that time. But I think as our organic growth started to taper a little bit, it was still strong, what I could have done was instead of leaning into my area of strength and really focusing on product and engineering, which I knew really well, was to lean more into discomfort and spend a lot more time, not being a marketer, but learning about what good marketing is, and building up my skills there where I was weakest. So I think that I started doing that later on as CEO, but I wish I had started doing that from the very beginning. And from a practical standpoint, I think that would just mean meeting CMOs, just from a networking standpoint, having coffee, understanding what good is. And I could spot a good technologist from a mile away, but I was still learning how to evaluate marketing leaders, so I would've done that. I think leaning into, it's a little bit counter to Peter Drucker, focus on your strengths, but I think it's to be a little more nuanced about it, figuring out what your weakness is and focusing on, maybe not learning that skill, but really, really bolstering your talent around you in that area, and so that was marketing for me.

Matt Blumberg: Yeah, I think CEOs who get promoted out of a functional area always have a lot to learn and then always have, I think, an awkward relationship with the function they left.

Chad Dickerson: Yeah, I know. I'll never forget my first week as CEO, I had two back- to- back meetings, one with the engineering team, or the engineering leaders, and one with some business people in the company. And the engineering team came in and they said, " I feel like you've abandoned us," because the day I became CEO I unsubscribed from all the mailing lists, got out of all the Slack channels, and I was like, " You're running technology. I don't want to look like I'm meddling." So they told me that. And then the next meeting, a business person, maybe it was a BD person, said, " I feel like all you really think about is engineering," and I was just like, " Oh."

Matt Blumberg: Can't win.

Chad Dickerson: And I think, to a great extent, and I understand this, because I had been CTO, I had that identification the whole time, but I tried. It's funny, the engineering, some of the engineering leaders called me a suit after I became CEO. I don't know if they were joking or not, but probably doesn't matter.

Matt Blumberg: All right. So in your current world, you're a coach.

Chad Dickerson: Yeah.

Matt Blumberg: You coach CEOs. So after you left Etsy, you took a little downtime, you started coaching, you did some work with our mutual friend Jerry Colonna at Reboot.

Chad Dickerson: That's right.

Matt Blumberg: Jerry's also going to be on the show this season.

Chad Dickerson: Oh, awesome.

Matt Blumberg: It's his new book. He has a new book coming out called Reunion, which is very good. And then after a while, you started doing it on your own as well. So let's start with the name of your firm.

Chad Dickerson: Yeah. So the name Strong Back Open Heart, actually the concept, it's not, I guess I discovered it, it already existed. But working with Jerry Colonna as my coach and I was trying to articulate the kind of organization that I wanted to build at Etsy, the character of the organization. And the simple way to explain it, from a leadership standpoint, is the Strong Back is fiscal responsibility, planning, goal setting, giving feedback, all of the work of creating an operating cadence and an operating rhythm. And the Open Heart I think is the human side, and understanding people and motivation and culture and dealing with how people feel and that sort of thing. And so the idea is, I really thought, and still think, that the best organizations are the ones that have both of those in balance. I was thinking about this before I read Radical Candor, but the grid that Kim Scott has, I can't remember what the axes are, but basically if you're too overweighted on the Open Heart side, you have what Kim calls ruinous empathy, you're almost too understanding and you get caught up in others' dramas. But if you're too much on the Strong Back, it's all operations, no humanistic touch, then you lose the sense of purpose and connectedness that's required in a company. And so my coaching firm has named that because on a good day, I like to think that I can help people find that area of balance. We live in a world of binary dualistic thinking and I think holding those two concepts in your mind at the same time is where the real power is.

Matt Blumberg: Yeah, look, it's one of the things about the CEO job, you constantly have to hold two opposite things in your mind, whether it's those two things or any two others.

Chad Dickerson: Yeah. Even the simple idea of we're doing really well, but we're also not making any progress. And actually, I've always admired the way you've run your companies, and I think the way you run Return Path, I don't think I've ever said this to you before, but I think some of those principles of the Strong Back Open Heart, I see that really present in the work that you do.

Matt Blumberg: Well, hopefully true at Bolster as well.

Chad Dickerson: Yeah, definitely true at Bolster.

Matt Blumberg: It's a lot easier with 30 or 40 people on the team than it is with hundreds and hundreds.

Chad Dickerson: Yes, definitely.

Matt Blumberg: So what's your favorite part about coaching CEOs, and what's your least favorite part about coaching CEOs?

Chad Dickerson: Yeah, my favorite part is, I think more than any other constituent or person in the CEO's life, other than perhaps spouse or really close friends, I get to see the reality of what it's like to run a business. And so there are times that I read a media interview with the CEO I'm working with, and this person's saying, " This is going so well and this is so great," and I know that that's not the whole story. And so I'm really fascinated with people. I think when I majored in English lit and studied Shakespeare, I think it was like I'm just fascinated with human nature. And so to see and be a part of someone's struggles and triumphs, I think is like an honor because I get to see it up close in all its messiness and glory. So just getting to know the person as a person is probably the best part in that way. What is the worst part? I never thought about that too much. I think that this is not so much about... Well, I guess this would work. I also see some of the bad behavior that happens in companies and on boards. There's some great boards out there and some great investors and that kind of thing, but it's upsetting to me when I see people get treated in inhumane ways, or people not being honest and giving the hard message and instead backstabbing, I guess. And so seeing that ugly side, I think, can be kind of painful, and I can feel that through the client sometime when I think they're being treated unfairly.

Matt Blumberg: Yeah, I can see that. Look, it's bad when it happens to you, it's got to be frustrating when it happens to the person you're advising.

Chad Dickerson: Yeah, and I would also add that I didn't realize until I started coaching how much I had seen in a business, and I've probably coached in 40 or 50 companies now, and I feel like I've seen almost nothing that's totally surprising to me. And so sometimes you see with an inexperienced leader, the people around them almost prey on their naivete, whether it's investors or more senior executives. And so I try to help people navigate those things and spot problems and issues. But that's another thing that really bothers me, when I see an investor trying to tell a CEO that something is normal when it's not, or something like that.

Matt Blumberg: With asymmetric information, " Oh, this is normal, we do this all the time," you're saying that to a CEO that has an experience set of one.

Chad Dickerson: Exactly. But I don't want to sound like I'm down on investors because I think you and I have worked with some really great investors and the great ones are incredible in their personhood and ability to deliver returns, and so I'm really amazed by that.

Matt Blumberg: All right, last question. If you could give your younger self a piece of advice now, and let's say shortly after you became CEO of Etsy, so you don't have to go way, way back, but if you, knowing what you know now as a coach to a number of CEOs, could give your first time CEO self one piece of advice about scaling up as a leader, what would it be?

Chad Dickerson: Yeah, I would say take more breaks because I think that the whole time I was at Etsy, there was so much going on and it seemed like every year was a whole new set of challenges. And so I spent a lot of time thinking, " I'm going to take a vacation in six months or whatever." I didn't do a very good job of planning vacations. And I think looking back, I was there for nine years, and six years as CEO. I look back and I was way more exhausted than I thought I was at the time, I think I was psyching myself out. And I think it would've done me really good to just take a couple of weeks off, let the team run things, and just step away. But I was just holding on a little bit too tight.

Matt Blumberg: Yeah. Probably would've been better for you and would've been better for your team.

Chad Dickerson: Definitely. Definitely, definitely. And I'll never forget, I went to the doctor right post Etsy, a stressful time, I just left the company, and a lot of my numbers were all over the place and the doctor said, " Come back in a few weeks. This is odd." And I came back after de- stressing for a month and all of my physical characteristics and numbers were better. So I think the stress was just coursing through my veins. And a lot of the CEOs I speak with, I've gone through some transitions with some of my clients and I've heard similar things, but I think someone said to me, I didn't understand it at the time, they say, " Don't quit, just get rest." And then I didn't quit, but I think I needed to rest so that I would have more gas in the tank.

Matt Blumberg: All right. Great advice to end on. Chad Dickerson, thank you so much for being here.

Chad Dickerson: Thanks, Matt.