The Exchanges

Q You mentioned kind of having that contrarian view. I'm really interested because, you know, as you said, it was a tougher time when you, you Thinking of those tougher times, um, you know, famous saying, never let a good crisis go to waste. I'd love to hear your thoughts. How do you think about that? And, frankly, those times when it is tougher, quite frankly.

A Yeah, I mean, a phrase I use a lot, never let a good crisis go to waste. And many leaders get paralyzed in a time of crisis, but it's actually incredibly liberating. When the only alternative to success is abject failure, it focuses the mind, right? When staying the course results in the company, you know, not existing anymore, you're given tremendous permission. In many ways, the risk of change has dropped tremendously, and I think there's a couple of things that I've learned to really focus on. The main thing is keeping the main thing the main thing. So what does success look like, and what are the fewest things we need to do to succeed, and how do we then clear the path and get rid of all of the noise? In order to just do those few things. The other thing I've observed in companies that have achieved some level of success is they confuse that they've succeeded because of and the things they've succeeded in spite of. What the company has done has become lore, and we've got to keep doing that. And in fact, for any company, you've achieved success because of a certain set of things and in spite of a certain set of things. Many companies don't really stop to reflect deeply On parsing out the difference. And a time of crisis can give you a chance to really do that. An example is at Etsy. Etsy believed that because Etsy was about handmade, Etsy should make everything itself. So Et…

AI assessment note: “many leaders get paralyzed in a time of crisis, but it's actually incredibly liberating.”

Q not always going to be loved, you know. It's much easier being the happy-go-lucky, for me, you know, charismatic, good-looking English chap. That was self-proclaimed, by the way, sadly. But, like, you know, fundamentally, you do sometimes have to not be Mr. Nice Guy and not be afraid to be disliked. How do you think about getting comfortable with not being loved or liked by everyone? That's my biggest challenge.

A I'm an empathetic person. I think most of us who are leaders are empathetic people, and so we like to be liked. I like to be liked. I think if decisions are made transparently with the customer's interests leading first, people will respect those decisions even when those decisions are difficult. We've made a lot of very difficult decisions at Etsy, and I I'm sure that I was not well-liked in the beginning. You know, we had to lay off over 200 people, you know, within five weeks of joining the company, we'd laid off 20% of the staff, and of the remaining staff, probably 80% of them had new jobs, and we'd shut down over half of all the projects that the company was working on. It was tremendously disruptive to people's lives, and it was very difficult, and I'm sure that I wasn't winning a lot of popularity awards at the time, but I said from the beginning, this is about lifting up our sellers and serving them better, and we're going to have to go do a lot of hard things, but there are bigger things at stake than our own feelings. We can all feel happy and content with ourselves and fail our sellers, and we won't have served anyone, and we won't feel much satisfaction later in life looking back. So what I think we've done fairly well as a team is transfer Apparently share why did we make the decisions we made, and what did we consider in making those decisions? One thing I do a l…

AI assessment note: “there are bigger things at stake than our own feelings”

Q Yeah. Yeah. No, I agree with you in terms of the importance there on balance. The other was when you said about kind of the dogma and knowing when to disregard it, when dogmas worked for you or like a set of practices has worked for you in the past, how do you know when to shed versus when to keep them with that in mind moving forward?

A So there's often a lot of gold hiding under the sacred cow. One of the first things I've done when coming into a company is look at what their core beliefs are. And inspect whether that core belief is actually adding value or not. You know, earlier in my career, I had the privilege of running a company called Marktplatz in the Netherlands, which was sort of the Craigslist of the Netherlands, but bigger and more successful. And it had grown to be, you know, the dominant marketplace in the Netherlands. And so the team believed that everything they did made it that way. One of the things that they really believed was that super fast page load times mattered, which of course we all believe. And therefore, they only allowed three photos, and the photos had to be low-res thumbnails. And the reason is, and that sort of low-res thumbnail was like, was enshrined almost as though Moses had come down from the mountain with, thou shalt have low-res thumbnail, you know, inscribed on a tablet. And, you know, at the time that the company was founded, people connected to the internet through dial-up, largely. And by the time we bought the company, almost everyone in the Netherlands had broadband internet access. And, you know, so we, we tested what happens if you, you know, use high-res... Photos and a lot more of them, and of course, it drove conversion rate, but believe it or not, it was ver…

AI assessment note: “look at what their core beliefs are. And inspect whether that core belief is actually adding value”

Q And we say, oh, you learn so much from failure and actually, you know, success is great, but you don't actually have that many learnings from it. I always disagree quite strongly. I think people just don't spend the time doing post-mortems on some Yeah. How do you think about that? You learn more from failure than success, and what's your experience been with the two and the subsequent learning?

A Well, I mean, if you're not succeeding often enough, you don't have a right to continue, right? You could have a lot of learnings if all you do is fail, but at the end of the day, you're not going to have anything. I think your point about not doing postmortems on success is a fascinating one, and this notion, I think that gets back to that we succeeded in spite of the following, you know, because of the following things, but in spite of the following things. That's a great process to put in place to To try to unpack that. I think that setting up a system, the notion that it's great to fail, setting up a system where failure is affordable, and picking when you can fail are two important. If you're going to embrace failure, you've got to have those two things in place. So on the first one, you know, at Etsy, we do have a really agile software development system where, you know, in general, we can go from idea to live to site in a couple weeks. And we test it in front of You know, the old version, and if it doesn't work, we roll it back, and so the opportunity cost of failure for most things is quite low, so we can afford to fail and get learnings. Now, one of the things we do with every experiment that fails, and by the way, we do, you know, tens of experiments per week. For every experiment that fails, we ask ourselves, could we have learned this faster and cheaper? So often, w…

AI assessment note: “setting up a system where failure is affordable, and picking when you can fail”

Q You mentioned kind of having that contrarian view. I'm really interested because, you know, as you said, it was a tougher time when you, you Thinking of those tougher times, um, you know, famous saying, never let a good crisis go to waste. I'd love to hear your thoughts. How do you think about that? And, frankly, those times when it is tougher, quite frankly.

A Yeah, I mean, a phrase I use a lot, never let a good crisis go to waste. And many leaders get paralyzed in a time of crisis, but it's actually incredibly liberating. When the only alternative to success is abject failure, it focuses the mind, right? When staying the course results in the company, you know, not existing anymore, you're given tremendous permission. In many ways, the risk of change has dropped tremendously, and I think there's a couple of things that I've learned to really focus on. The main thing is keeping the main thing the main thing. So what does success look like, and what are the fewest things we need to do to succeed, and how do we then clear the path and get rid of all of the noise? In order to just do those few things. The other thing I've observed in companies that have achieved some level of success is they confuse that they've succeeded because of and the things they've succeeded in spite of. What the company has done has become lore, and we've got to keep doing that. And in fact, for any company, you've achieved success because of a certain set of things and in spite of a certain set of things. Many companies don't really stop to reflect deeply On parsing out the difference. And a time of crisis can give you a chance to really do that. An example is at Etsy. Etsy believed that because Etsy was about handmade, Etsy should make everything itself. So Et…

AI assessment note: “When the only alternative to success is abject failure, it focuses the mind”

Q transition from first act to second act, it's Do you have to ask, you said there about the kind of background and also the political elements. Danny Reimer said about your kind of innate curiosity across many different realms. And he said, like, did you always think that you'd be running a multi-billion dollar company? And how do you think those experiences prepared you to be the CEO you are?

A I certainly didn't. I mean, if you'd asked the young me, the Josh Silverman in high school, I was going to be a professional jazz musician. And then in college, I was going to be an actor. And I think I am where I am today. To some extent, because I was so untalented in the performing arts that I had to fall back on something else. But I think what has been true of me is I didn't have a plan that said, 20 years from now, I want to be this. I've tended to measure my life out in three to four year sprints. Over the next three to four years, what would be a great accomplishment I could be really proud of? And then I've poured myself in with no reservation and a tremendous amount of passion to get to that three to four year milestone. And in picking what those milestones would be, you know, mostly it's, do I think I would learn a ton? Would I work with amazing people? And would it give me skills that are transferable and useful that expand my optionality rather than contract, than constrain my optionality? And using that as a metric has been helpful. I think this notion that you've got to figure out what you're going to do for the next 20 years can be so overwhelming. And life has so much luck and Fate involved that if you hang everything on some twenty-year aspiration, the probability that something is going to derail you is great. Three to four years at a time, that's kind of an …

AI assessment note: “I certainly didn't. I mean, if you'd asked the young me”

Q a lot of what I do, and I'm like, shit, I really need to evolve here, and then some people go, no, no, Fuck that. You can hire someone to do that. Just focus on what you're great at. Just focus on that. And then other times I think, no, that's idealistic. How do you determine between fundamentally need to evolve versus not a core competency can delegate or hire?

A I think there's table stakes and there's your spikes or strengths, right? So whatever your job is, there's table stakes good enough. I'm not a project manager by nature. It's not What I'm great at. But to be an effective CEO, there's a table stakes level of project management that I need to have and be capable of, and I've worked hard to get to table stakes. I'm not saying I'm going to be great, and I surround myself with people who are much better at that than me, but if I don't have some level of orientation around operations, I won't have enough empathy for the people on my team who really need to do that and make that work. And then I do try, I've learned, try to learn more and more what are the things that I'm uniquely good at. And how can I leverage those more and bring those more into the company? But I think this notion that only focus on your strengths and sort of let yourself off the hook on all your weaknesses. I don't know. I don't love that. I know I always want to evolve. I always want to get better. I'm a continuous work in progress, and I just don't think I'm capable of that.

AI assessment note: “there's table stakes and there's your spikes or strengths”

Q transition from first act to second act, it's Do you have to ask, you said there about the kind of background and also the political elements. Danny Reimer said about your kind of innate curiosity across many different realms. And he said, like, did you always think that you'd be running a multi-billion dollar company? And how do you think those experiences prepared you to be the CEO you are?

A I certainly didn't. I mean, if you'd asked the young me, the Josh Silverman in high school, I was going to be a professional jazz musician. And then in college, I was going to be an actor. And I think I am where I am today. To some extent, because I was so untalented in the performing arts that I had to fall back on something else. But I think what has been true of me is I didn't have a plan that said, 20 years from now, I want to be this. I've tended to measure my life out in three to four year sprints. Over the next three to four years, what would be a great accomplishment I could be really proud of? And then I've poured myself in with no reservation and a tremendous amount of passion to get to that three to four year milestone. And in picking what those milestones would be, you know, mostly it's, do I think I would learn a ton? Would I work with amazing people? And would it give me skills that are transferable and useful that expand my optionality rather than contract, than constrain my optionality? And using that as a metric has been helpful. I think this notion that you've got to figure out what you're going to do for the next 20 years can be so overwhelming. And life has so much luck and Fate involved that if you hang everything on some twenty-year aspiration, the probability that something is going to derail you is great. Three to four years at a time, that's kind of an …

AI assessment note: “I certainly didn't. I mean, if you'd asked the young me”

Q a lot of what I do, and I'm like, shit, I really need to evolve here, and then some people go, no, no, Fuck that. You can hire someone to do that. Just focus on what you're great at. Just focus on that. And then other times I think, no, that's idealistic. How do you determine between fundamentally need to evolve versus not a core competency can delegate or hire?

A I think there's table stakes and there's your spikes or strengths, right? So whatever your job is, there's table stakes good enough. I'm not a project manager by nature. It's not What I'm great at. But to be an effective CEO, there's a table stakes level of project management that I need to have and be capable of, and I've worked hard to get to table stakes. I'm not saying I'm going to be great, and I surround myself with people who are much better at that than me, but if I don't have some level of orientation around operations, I won't have enough empathy for the people on my team who really need to do that and make that work. And then I do try, I've learned, try to learn more and more what are the things that I'm uniquely good at. And how can I leverage those more and bring those more into the company? But I think this notion that only focus on your strengths and sort of let yourself off the hook on all your weaknesses. I don't know. I don't love that. I know I always want to evolve. I always want to get better. I'm a continuous work in progress, and I just don't think I'm capable of that.

AI assessment note: “I think there's table stakes and there's your spikes or strengths”

Q you do when, and sorry, we have a schedule and we're just totally ignoring it, but this is too helpful. When you have two options in front of you, And you just don't know. As you said, the world is ever-changing. The complexities within each are often quite opaque, and it's not as transparent as one thinks. What do you do when you don't know, and you're weighing those two?

A My life has been punctuated by a series of inflection points where I've taken the job most people thought I shouldn't take, and so figuring out how to balance risk and opportunity is something I've spent a lot of time thinking about. In fact, I think every job I've ever had In the past 20 years, I've gotten because most other people wouldn't take it. You know, I mean, when they asked me to run Skype, I was at eBay. Honestly, they spent four months looking to find anyone else, and no one would take that job because, you know, it's in the telecommunications industry, which is highly regulated, and international phone calls were going to zero, you know, becoming free, and Skype was really built around the whole world can talk for free. Etsy, you know, was in a very challenging position. Uh, you know, on and on each of those jobs, you know, everyone I asked for their opinion said, oh, for God's sake, don't do that. But when I looked at Skype, when I looked at Etsy, what those companies do for their customers, what they do for the world is so important and so valuable that I felt like we could build something great. If it worked, my team and I would cover ourselves in glory. And so thinking about the upside and the downside path, I tend to be very deliberate about thinking, what if it goes well and what if it doesn't? And, you know, if it goes well, it needs to be really meaningful.…

AI assessment note: “I tend to be very deliberate about thinking, what if it goes well and what if it doesn't?”

Q Can I ask, when you then identify the vital few and you actually have real definition and focus around the Strategic pathway forward. And you think about the team around you. You know, you said before about the importance of delegating without abdicating. What did you mean specifically by that? And how do you think about effective delegation in particular?

A So I worked for Ken Chenault at American Express, and he taught me leadership is about defining success and defining constraints. And the more I've been on my journey, the more I realize it's those two things plus one. I would add one thing, which is making sure you have the right people on the team. But if a leader does only those things, define success, define constraints, and make sure you have the right people on the team, everything else takes care of itself. When I, when I was earlier in my career, I thought my job was to have good ideas and be a good problem solver. And it was something I was good at, and so I tended to lean on it. And, you know, I quickly scaled out of that. So it sounds easy, does hard. Define success and define constraints. There's an art and a science to it. But the better you can do as a leader of, Clearly defining what success and constraints look like, and then getting out of the way to allow your team to innovate to achieve that goal, the better you will do. I'll give you an example. When I took over at Skype, Meg Whitman was the CEO of eBay, which owned Skype at the time, and she had sort of talked a lot about Skype. Four dot O was this new platform Skype was going to launch that was going to, you know, change the trajectory and fortunes of Skype. Skype was sort of decelerating and declining rapidly, and so I was put in as the new CEO, and in th…

AI assessment note: “defining what success and constraints look like, and then getting out of the way”

Q Yeah. Yeah. No, I agree with you in terms of the importance there on balance. The other was when you said about kind of the dogma and knowing when to disregard it, when dogmas worked for you or like a set of practices has worked for you in the past, how do you know when to shed versus when to keep them with that in mind moving forward?

A So there's often a lot of gold hiding under the sacred cow. One of the first things I've done when coming into a company is look at what their core beliefs are. And inspect whether that core belief is actually adding value or not. You know, earlier in my career, I had the privilege of running a company called Marktplatz in the Netherlands, which was sort of the Craigslist of the Netherlands, but bigger and more successful. And it had grown to be, you know, the dominant marketplace in the Netherlands. And so the team believed that everything they did made it that way. One of the things that they really believed was that super fast page load times mattered, which of course we all believe. And therefore, they only allowed three photos, and the photos had to be low-res thumbnails. And the reason is, and that sort of low-res thumbnail was like, was enshrined almost as though Moses had come down from the mountain with, thou shalt have low-res thumbnail, you know, inscribed on a tablet. And, you know, at the time that the company was founded, people connected to the internet through dial-up, largely. And by the time we bought the company, almost everyone in the Netherlands had broadband internet access. And, you know, so we, we tested what happens if you, you know, use high-res... Photos and a lot more of them, and of course, it drove conversion rate, but believe it or not, it was ver…

AI assessment note: “inspect whether that core belief is actually adding value or not.”

Q not always going to be loved, you know. It's much easier being the happy-go-lucky, for me, you know, charismatic, good-looking English chap. That was self-proclaimed, by the way, sadly. But, like, you know, fundamentally, you do sometimes have to not be Mr. Nice Guy and not be afraid to be disliked. How do you think about getting comfortable with not being loved or liked by everyone? That's my biggest challenge.

A I'm an empathetic person. I think most of us who are leaders are empathetic people, and so we like to be liked. I like to be liked. I think if decisions are made transparently with the customer's interests leading first, people will respect those decisions even when those decisions are difficult. We've made a lot of very difficult decisions at Etsy, and I I'm sure that I was not well-liked in the beginning. You know, we had to lay off over 200 people, you know, within five weeks of joining the company, we'd laid off 20% of the staff, and of the remaining staff, probably 80% of them had new jobs, and we'd shut down over half of all the projects that the company was working on. It was tremendously disruptive to people's lives, and it was very difficult, and I'm sure that I wasn't winning a lot of popularity awards at the time, but I said from the beginning, this is about lifting up our sellers and serving them better, and we're going to have to go do a lot of hard things, but there are bigger things at stake than our own feelings. We can all feel happy and content with ourselves and fail our sellers, and we won't have served anyone, and we won't feel much satisfaction later in life looking back. So what I think we've done fairly well as a team is transfer Apparently share why did we make the decisions we made, and what did we consider in making those decisions? One thing I do a l…

AI assessment note: “there are bigger things at stake than our own feelings”

Q And we say, oh, you learn so much from failure and actually, you know, success is great, but you don't actually have that many learnings from it. I always disagree quite strongly. I think people just don't spend the time doing post-mortems on some Yeah. How do you think about that? You learn more from failure than success, and what's your experience been with the two and the subsequent learning?

A Well, I mean, if you're not succeeding often enough, you don't have a right to continue, right? You could have a lot of learnings if all you do is fail, but at the end of the day, you're not going to have anything. I think your point about not doing postmortems on success is a fascinating one, and this notion, I think that gets back to that we succeeded in spite of the following, you know, because of the following things, but in spite of the following things. That's a great process to put in place to To try to unpack that. I think that setting up a system, the notion that it's great to fail, setting up a system where failure is affordable, and picking when you can fail are two important. If you're going to embrace failure, you've got to have those two things in place. So on the first one, you know, at Etsy, we do have a really agile software development system where, you know, in general, we can go from idea to live to site in a couple weeks. And we test it in front of You know, the old version, and if it doesn't work, we roll it back, and so the opportunity cost of failure for most things is quite low, so we can afford to fail and get learnings. Now, one of the things we do with every experiment that fails, and by the way, we do, you know, tens of experiments per week. For every experiment that fails, we ask ourselves, could we have learned this faster and cheaper? So often, w…

AI assessment note: “setting up a system where failure is affordable, and picking when you can fail”

Q you do when, and sorry, we have a schedule and we're just totally ignoring it, but this is too helpful. When you have two options in front of you, And you just don't know. As you said, the world is ever-changing. The complexities within each are often quite opaque, and it's not as transparent as one thinks. What do you do when you don't know, and you're weighing those two?

A My life has been punctuated by a series of inflection points where I've taken the job most people thought I shouldn't take, and so figuring out how to balance risk and opportunity is something I've spent a lot of time thinking about. In fact, I think every job I've ever had In the past 20 years, I've gotten because most other people wouldn't take it. You know, I mean, when they asked me to run Skype, I was at eBay. Honestly, they spent four months looking to find anyone else, and no one would take that job because, you know, it's in the telecommunications industry, which is highly regulated, and international phone calls were going to zero, you know, becoming free, and Skype was really built around the whole world can talk for free. Etsy, you know, was in a very challenging position. Uh, you know, on and on each of those jobs, you know, everyone I asked for their opinion said, oh, for God's sake, don't do that. But when I looked at Skype, when I looked at Etsy, what those companies do for their customers, what they do for the world is so important and so valuable that I felt like we could build something great. If it worked, my team and I would cover ourselves in glory. And so thinking about the upside and the downside path, I tend to be very deliberate about thinking, what if it goes well and what if it doesn't? And, you know, if it goes well, it needs to be really meaningful.…

AI assessment note: “I tend to be very deliberate about thinking, what if it goes well and what if”

Q making. I love that kind of framework and matrix. Final question for the quick foreign. It's like, when you think about the frameworks and matrix like that, that you have now as a CEO that When you compare yourself to your former years as a CEO, you know, I'm sure you've changed immensely. How have you changed as a CEO, do you think, over the last 10 to 15 years?

A Oh, I think the poor folks who worked with me at Evite wouldn't recognize me, and I hope 10 or 15 years from now, I'll look back at my current self and say, oh my gosh, I'm so much better. I mean, I definitely see myself as a work in progress, and I think of myself as a craftsperson in the craft of leadership. I'm constantly trying to hone and refine my craft. And get better. And a couple of things. I'm a very active role modeler. I'm a voracious reader. I read biographies all the time, and I try to go meet all kinds of impressive leaders, and not just impressive leaders you read about in the paper. Every person I work with, I learn something from. The people who work with me at Etsy are amazing, incredible people. And every person I work with, there's some quality they have that I admire that they do better than me. And I'm constantly looking at what can I learn from this person and how they handle this situation or how they think about this craft or how they ask those questions and think, how can I start to incorporate that? The second thing that's been very helpful for me is times for real contemplation. I've had a couple of, of periods in my life where I've had, you know, three months off, five months off, and the chance to reflect back on my work and think, what would I have done differently with the most critical eye? Those have been incredibly valuable and painful, you k…

AI assessment note: “the poor folks who worked with me at Evite wouldn't recognize me”

Q Yeah, and then tell me, most excitingly, what's the next five years hold for you and for Etsy? Paint that picture for me, Josh.

A I think There's an implicit notion in the markets that there's going to be millions of individual places to buy things online. You know, if you're following the market cap of Shopify and Wix and Stripe and all of the other places out there, you know, the thesis must be that you're going to have millions of individual shops on the internet that are all trying to sell you stuff. I find that thesis exceptionally unlikely. The brain can only remember a couple of brands, and so I think the world is consolidating around Fewer and fewer places to buy things online. I mean, if you're a tiny independent shop, you're going to recount on Google or Facebook to drive all your traffic, and if you're downstream of Google and Facebook, they get all the economics, and you can't really survive. So I think there's going to be only a tiny handful of places to buy things online. I think Amazon will continue to be the default for everyone in the Western world, and the more the world has a default, the more it yearns for an antidote. To that default. And I think Etsy's incredibly well positioned to be the antidote to Amazon as the default.

AI assessment note: “Etsy's incredibly well positioned to be the antidote to Amazon as the default.”

Q making. I love that kind of framework and matrix. Final question for the quick foreign. It's like, when you think about the frameworks and matrix like that, that you have now as a CEO that When you compare yourself to your former years as a CEO, you know, I'm sure you've changed immensely. How have you changed as a CEO, do you think, over the last 10 to 15 years?

A Oh, I think the poor folks who worked with me at Evite wouldn't recognize me, and I hope 10 or 15 years from now, I'll look back at my current self and say, oh my gosh, I'm so much better. I mean, I definitely see myself as a work in progress, and I think of myself as a craftsperson in the craft of leadership. I'm constantly trying to hone and refine my craft. And get better. And a couple of things. I'm a very active role modeler. I'm a voracious reader. I read biographies all the time, and I try to go meet all kinds of impressive leaders, and not just impressive leaders you read about in the paper. Every person I work with, I learn something from. The people who work with me at Etsy are amazing, incredible people. And every person I work with, there's some quality they have that I admire that they do better than me. And I'm constantly looking at what can I learn from this person and how they handle this situation or how they think about this craft or how they ask those questions and think, how can I start to incorporate that? The second thing that's been very helpful for me is times for real contemplation. I've had a couple of, of periods in my life where I've had, you know, three months off, five months off, and the chance to reflect back on my work and think, what would I have done differently with the most critical eye? Those have been incredibly valuable and painful, you k…

AI assessment note: “I definitely see myself as a work in progress, and I think of myself”

Q Not at all, but I do want to start with some context. So tell me, how did you make your way into the world of startups that we both love so much, and most importantly, now come to be CEO at Etsy?

A Oh gosh, there certainly wasn't a plan. I started out as a public policy major in college with a Deep passion for fixing the healthcare system in the United States, and I went to work for a senator for a couple of years in Washington, D.C., answering mail and writing policy positions and sort of worked my way up from there, but I ended up as a management consultant, realized that isn't what I wanted to do, and really felt like the best way to have a positive impact on my community was to run a business. I think when you run a business, you're able to really move much more quickly than in policy, and I think do a lot of things that can positively impact Community. So

AI assessment note: “I started out as a public policy major in college”

Q Can I ask, as a leader, what's the right way to challenge dogma and ingrained principles? Is it to come in and say, hey, that was the past, this is the future? Is it gradual, hey, we should think about this? How do you think about that transition process and how binary it should be?

A I think the most important thing is to orient everyone around a mission that you all have shared belief in. If you're going to take the team through very hard times, which building any business over time, you're going to go through hard times together. You all have to have a shared belief in something bigger than yourselves, and something bigger than the stock price or the market cap. So what is it that we are doing for our community at large and our customers that is so important that we should spend the hours we do on it, Take the personal risk we do. You know, getting back to your question about happiness and risk, I don't want to spend a lot of time on any endeavor in life that I don't think will have a purpose greater than, than myself. So finding that key purpose is, is important. And then when you frame everything in terms of service to that purpose, it becomes a lot easier to stomach all of the change we're making and questioning our own beliefs. So at Etsy, worked hard to figure out what that purpose was. And it's keeping commerce human. That's our mission. It's keeping commerce human. And in a world that's becoming more commoditized and less human, we think that's, that's really important. And we frame everything in terms of service to our sellers. We have four million sellers right now. And, you know, you want to know why politics is so fraught. Life's not that easy …

AI assessment note: “when you frame everything in terms of service to that purpose, it becomes a lot easier”

Q Can I ask, when you then identify the vital few and you actually have real definition and focus around the Strategic pathway forward. And you think about the team around you. You know, you said before about the importance of delegating without abdicating. What did you mean specifically by that? And how do you think about effective delegation in particular?

A So I worked for Ken Chenault at American Express, and he taught me leadership is about defining success and defining constraints. And the more I've been on my journey, the more I realize it's those two things plus one. I would add one thing, which is making sure you have the right people on the team. But if a leader does only those things, define success, define constraints, and make sure you have the right people on the team, everything else takes care of itself. When I, when I was earlier in my career, I thought my job was to have good ideas and be a good problem solver. And it was something I was good at, and so I tended to lean on it. And, you know, I quickly scaled out of that. So it sounds easy, does hard. Define success and define constraints. There's an art and a science to it. But the better you can do as a leader of, Clearly defining what success and constraints look like, and then getting out of the way to allow your team to innovate to achieve that goal, the better you will do. I'll give you an example. When I took over at Skype, Meg Whitman was the CEO of eBay, which owned Skype at the time, and she had sort of talked a lot about Skype. Four dot O was this new platform Skype was going to launch that was going to, you know, change the trajectory and fortunes of Skype. Skype was sort of decelerating and declining rapidly, and so I was put in as the new CEO, and in th…

AI assessment note: “Clearly defining what success and constraints look like, and then getting out of the way”

Q Okay, so favorite book and why? What must I be reading?

A I read about 50 books a year, because Audible has changed my life, so I listen to books. Right now I'm listening to a biography of Ulysses Grant, and what I love about it is... He's someone who could fade into any background. I mean, he's the general who led the union to win the civil war in the United States. And we have this notion of generals being these larger than life, charismatic personalities. And he was the opposite of that. He was the wallpaper in which you'd fade into in any room. And two years prior to leading a million soldiers in the war, he was a shop clerk in a leather store and the junior shop clerk and not a good one at that. He had failed as a farmer. So in any other role, he was a total failure. But in the right place at the right time, he was one of the greatest generals in American, if not world history. And we all, you know, everyone in the U.S. owes an amazing debt of gratitude to him. It's incredibly lemming-like, very internally focused, a giant echo chamber. I really love not living in Silicon Valley so that I can maintain enough objectivity and external perspective.

AI assessment note: “Right now I'm listening to a biography of Ulysses Grant, and what I love about”

Q Not at all, but I do want to start with some context. So tell me, how did you make your way into the world of startups that we both love so much, and most importantly, now come to be CEO at Etsy?

A Oh gosh, there certainly wasn't a plan. I started out as a public policy major in college with a Deep passion for fixing the healthcare system in the United States, and I went to work for a senator for a couple of years in Washington, D.C., answering mail and writing policy positions and sort of worked my way up from there, but I ended up as a management consultant, realized that isn't what I wanted to do, and really felt like the best way to have a positive impact on my community was to run a business. I think when you run a business, you're able to really move much more quickly than in policy, and I think do a lot of things that can positively impact Community. So

AI assessment note: “I started out as a public policy major in college with a Deep passion”

Q Can I ask, as a leader, what's the right way to challenge dogma and ingrained principles? Is it to come in and say, hey, that was the past, this is the future? Is it gradual, hey, we should think about this? How do you think about that transition process and how binary it should be?

A I think the most important thing is to orient everyone around a mission that you all have shared belief in. If you're going to take the team through very hard times, which building any business over time, you're going to go through hard times together. You all have to have a shared belief in something bigger than yourselves, and something bigger than the stock price or the market cap. So what is it that we are doing for our community at large and our customers that is so important that we should spend the hours we do on it, Take the personal risk we do. You know, getting back to your question about happiness and risk, I don't want to spend a lot of time on any endeavor in life that I don't think will have a purpose greater than, than myself. So finding that key purpose is, is important. And then when you frame everything in terms of service to that purpose, it becomes a lot easier to stomach all of the change we're making and questioning our own beliefs. So at Etsy, worked hard to figure out what that purpose was. And it's keeping commerce human. That's our mission. It's keeping commerce human. And in a world that's becoming more commoditized and less human, we think that's, that's really important. And we frame everything in terms of service to our sellers. We have four million sellers right now. And, you know, you want to know why politics is so fraught. Life's not that easy …

AI assessment note: “when you frame everything in terms of service to that purpose, it becomes a lot easier”