B-Schooled Podcast Episode #310: Josh Silverman on Evite, Skype, and Turning Around Etsy

This transcript has been lightly edited for clarity and length. Timestamps refer to the audio.

Stacy Blackman: Welcome to B-Schooled, the podcast by Stacy Blackman Consulting. I’m Stacy Blackman, and for more than 20 years, I’ve worked with ambitious, high-potential people navigating business school and everything that comes after. This series is called Paths Less Traveled. In it, I’m sitting down with MBA grads whose paths evolved over time in unexpected ways. These are conversations about optionality, reinvention, and what’s really possible when you stop thinking about the MBA as a first job and start thinking about it as a foundation. Let’s get into it.

Josh Silverman is Etsy’s Executive Chair and formerly served as Chief Executive Officer from May 2017 to December 2025, leading Etsy as it built a platform that empowers creative entrepreneurs around the world. He has been a member of Etsy’s Board of Directors since 2016. Josh’s two decades of leadership experience include growing consumer technology companies and scaling global marketplaces.

He previously served as President of Consumer Products and Services at American Express, CEO of Skype, and CEO of Shopping.com, and he held various executive roles at eBay. Earlier in his career, Josh co-founded Evite, Inc., where he also served as the company’s CEO. He is currently on the Board of Directors of Shake Shack, Instacart, and TechNet. Welcome, Josh Silverman.

Josh Silverman: Thank you. It’s great to be here.

Stacy: Thank you so much for taking the time to chat with me today. I’ve known you for quite a while and have really enjoyed seeing what your next move would be and how you’ve scaled the corporate ladder phenomenally well, so I’m excited to dig in. I’d like to rewind to the beginning, even before I knew you: end of college, pre-MBA. What were you doing at that time, and what made you decide to go back and get your MBA?

[02:20] Josh: It’s interesting when you say scaled the corporate ladder. I feel like I’ve done anything but that. My life has been a series of really non-obvious choices, and in hindsight it looks like that. I’m sure it can feel very daunting to young people, like there’s some clear path you should take, and my life was definitely not that. In fact, if there was a clear path, I made sure I was not on it. Whatever looked like the clear path to my colleagues, that was the one path I wasn’t on.

For example, I entered college as a theater major, and I spent my first several years trying to be an actor. I was really untalented at it and couldn’t get cast in anything good, and being at least self-aware, I realized, boy, this is probably not going to be a good profession for me. Along the way, I got really passionate about public policy, and I became a health care policy major. So it’s quite obvious how a health care policy major would have ended up in business doing everything I’ve done, right?

I graduated from college with no job. There was nothing in on-campus recruiting that felt interesting to me. One sense I had was, if every other student at Brown wanted a job, I definitely didn’t want that job. Why would I go compete against the smartest, most talented people in the world? I’m going to look for something that no one else at Brown is trying to do.

I really wanted to work in health care policy for a senator or a congressman in D.C. I graduated and just slept on couches in D.C. for weeks while I networked and talked my way into a job. I finally got hired in the mailroom of Senator Bill Bradley, a Democrat from New Jersey. My salary was $13,000 a year, and my portfolio was health and welfare, so I qualified for about a third of the welfare programs we were working on.

I spent the first 40 hours of every week answering mail, which is what I was paid to do, and I spent the next 40 hours doing work that nobody asked me to do: writing policy positions for the senator, helping to write speeches, doing public appearances. If he wasn’t available, I’d go meet with lobbyists or constituents on his behalf. I just kept raising my hand to do anything anyone needed, and I learned so much from that experience. It also let me distinguish myself among the staff.

One thing I observe is that a lot of the young people I talk to talk a lot about work-life balance, and I care a lot about work-life balance. But there was nothing I would rather have done at that age than be in the office, working with really interesting people on interesting things. So that was my early career launch.

[05:22] A few years in, the senator’s chief of staff called me into his office and said he was going to Booz Allen Hamilton to start a health care consulting practice for them, and I was coming with him, and he didn’t want to hear any back talk from me. That’s how I found myself a management consultant. At the time, I had never heard of the industry of management consulting. I’d never heard of McKinsey or Bain, much less Booz Allen. I didn’t know what an investment banker was. I thought they were the people who cashed my check when I went into a bank.

Stacy: Gosh, you’ve come a long way.

Josh: I’ve come a long way. So I spent two years working for Booz Allen doing management consulting, and when I looked up at the next job and the next job and the next job, there was no job at Booz Allen I admired. I didn’t want to be my boss or my boss’s boss. So I thought to myself, wow, I’d better go to business school as a way to replatform myself. I learned so much as a management consultant, and I was really happy I did it, but I knew it wasn’t the career for me. Business school was a way to pivot and replatform myself.

Stacy: So you decided to go to business school to take that time to transition, which I think is so common. I had a very clear goal, for instance, and I didn’t do anything remotely related to it. Even if we have a plan, we don’t always follow it, because B-school is so transformational. It kind of blows everything up, in my opinion. But you decide to apply, and you end up at Stanford. Tell me a little bit about those two years.

[07:19] Josh: Stanford was amazing. First, I knew I had a lot to learn about business. Unlike a lot of my classmates, who came in with a real grounding in finance and marketing and all those things, I’d studied none of that. I’d studied theater and acting. So I was really excited about the academics, and I actually worked really hard. The ethos of Stanford, in theory, is that no one’s working very hard; they’re just socializing.

But I really felt like the opportunity cost of two years was high. I was accumulating debt. I didn’t have any savings. I was living on very little and taking out loans to go to business school, and I felt like if I’m going to be here, I really want to make the most of it. So I studied really hard and learned a ton. I’m sure we’ll talk about that, but I still think so much today about the things I learned in business school that were so useful.

I also made a point of going to at least one meal with every classmate of mine. I think there’s one classmate I missed.

Stacy: That is amazing.

Josh: I really made a point. I typically had a breakfast, a lunch, and two dinners every single day, and when I look back at my calendar, it’s insane how scheduled I was. That would drive a lot of people crazy, but I just felt like, wow, I’ve got classmates who were in the military, classmates who worked in the auto industry, in finance, in the tech industry. I learned so much from meeting people from all over the world and from all sorts of different industries. It was a really vital part of my education, plus it was a ton of fun.

Stacy: That’s amazing. I love that. In all these years of working with so many MBA applicants, I have not heard anyone say that. That’s more doable at Stanford than at other schools.

Josh: Yes, we had 316 people in the class, so over the course of two years, if you want to, you can do that.

[09:31] Stacy: Love that. What did you think you’d get out of B-school compared to what you actually got out of it? Or maybe it was totally aligned. What are some of your takeaways, and were they what you thought they’d be?

Josh: I got a lot more out of it than I even thought I would, because I just had so far to go in terms of learning about business. But I’d say the main thing I got was understanding where there is science and where it’s just art. It turns out that in fields like finance and operations, there’s a lot of science. There is a right answer to many questions. In many other areas, there’s not a right answer. There are just judgment calls. Knowing when I could reach into my toolkit and get a right answer, and when I just had to use my best available judgment: business school gave me a really great grounding in that.

For example, in my first job after business school, I was working for a medical device technology company, and I was running field service. When these machines break, the folks who go fix them were reporting to me. They’re all working 100 hours a week, our customers are waiting days and days for a technician to arrive, it’s a mess, and it’s incredibly stressful for all of us.

Because of business school, I knew there’s an entire field called operations research, with a whole body of science called queuing theory, where you can run the math. For any particular service level agreement, say a tech will arrive within eight hours, and given the variability of calls coming in, you can run a formula and determine exactly how many technicians you need. By actually doing that math, I discovered that we were dramatically understaffed, and I was able to present a really data-driven case to the CEO. Had I not gone to business school, I wouldn’t have even known there was a right answer to the question.

Stacy: Right, that there was an analysis behind it. That makes sense.

Josh: There was PhD-level, physics-driven math around that, which interestingly comes out of the ATM industry: how many ATMs do you need in any given city so people don’t have to wait in line too long before withdrawing their cash? I think that’s the history of a lot of it. Anyway, that was just one example of knowing where there is a body of science and where there isn’t. It also gave me confidence in a lot of areas like marketing or HR to say, here are a lot of case studies I’ve read, but the truth is, there’s not a right answer. It’s a judgment call. Let me talk to a few people.

[12:30] Stacy: Right, and that was my next question. On the things that are more art, business school gave you the confidence to at least operate in uncertainty.

Josh: Business school is, to a large degree, the history of business. In a few classes, like accounting and finance, you’re learning a lot of science: what is the current state of knowledge around any given topic? In many of the other fields, what you’re reading are a lot of case studies about how other people have faced similar situations. So on the art side, at least I’ve got some basis in history: here are 10 examples of how other people handled a similar situation. That’s also a really useful toolkit.

Since graduating from business school, I’ve been a voracious reader of business biographies, because I’m constantly trying to expand my knowledge of how other people have dealt with similar situations. I find it incredibly useful. Business school is a really consolidated, compact version of that over the course of two years.

[13:43] Stacy: Definitely. So you go on. When I met you, you had just founded Evite. Did you have those entrepreneurial ideas when you were in business school?

Josh: When I entered business school, I had a sense that I wanted to run a company. By the time I graduated, I had conviction that I wanted to run a company. I also had conviction that I wouldn’t hire me to be the CEO of any company, because I had no experience managing people. I’d worked in a senator’s office, and then I’d worked in management consulting. With all due respect, managing management consultants is not like managing real people. Hyper-ambitious, hyper-educated people are one type of person you can manage, but typically in business, you need to manage a broad range of different kinds of people. So I looked for a company that was willing to give me an unreasonable amount of general management responsibility.

Again, I picked a very nontraditional path out of business school. There was a small-cap medical device company, publicly traded with a $600 million market cap, that no one had really ever heard of, called ADAC Laboratories. They made gamma cameras. Very random. But the CEO was really hard-charging, and they wanted to hire a top student from Stanford. I said, I want to run mergers and acquisitions for you. I want to go buy some companies on behalf of the business, and then I want to run whatever I bought. And they said, okay.

So I took a job that had no prestige or status. I had one of the lowest starting salaries of anyone in my class, but I had a really unreasonable amount of responsibility, and that worked out great. I learned a ton. The other thing I really liked about that company was that they were obsessed with winning something called the Malcolm Baldrige Award, which today we would call Six Sigma.

They had a business system that they executed with intensity, and I wanted to learn the system of how to manage a business well. I thought, that’s a place where I can really learn how to be a good general manager. So I spent a couple of years there, first running M&A and then running the businesses I’d just bought.

Stacy: That is a huge amount of responsibility for someone at your level.

Josh: Twelve months out of business school, I had 60 or 70 people reporting to me with maybe a $20 million P&L, so $20 million of revenue. The people who reported to me were almost all former military. They were people who had a high school education, went into the military, learned about electronics there, and then a lot of them went to DeVry University, where they learned more specific skills. Not the typical person you’re meeting at Stanford Business School, but super talented and super hardworking. I learned a ton working with those people, and I learned a ton about general management.

But I’m working 100 hours a week leading a team that fixes broken gamma cameras, and the internet is blowing up all around. This is now 1998. The internet has been born and is becoming a thing.

[17:37] So one of my business school classmates, one of my roommates from business school, and I decided we were going to start a business together. Every Saturday, he brings three ideas and I bring three ideas, and we tear each other’s ideas apart until we come up with an idea we both really love, which is a travel business for European vacation travel. He’s Spanish, so we’re going to build a business in Spain that’s about European travel.

One of the problems we were trying to solve was that in 1998, no one bought anything online. It didn’t feel safe giving a credit card number to something on the internet. There was just no infrastructure for it. So how would you get people comfortable actually buying something online? With European vacation travel, it’s a group of people. Someone goes and researches, and then the whole group needs to decide they’re going to go together. So I started thinking a lot about how you get the group to come to a decision and lock in: okay, it’s going to be Mallorca, it’s going to be this week, it’s going to be that hotel. We’ve all agreed. Click buy now.

And I thought, I need that all the time. I need it when I’m going to dinner. I need it when I’m trying to get a group of people to play basketball together. So I got really excited about what became Evite. I was calling it ToGather.com. It shouldn’t just be about travel; it should be about organizing all of your events, getting a group of people to agree on an event. I wanted to do that.

Stacy: By the way, ToGather is a good name too.

Josh: I thought it was okay. We were going to send “G-mails” to gather people together, and Gmail, the Google mail, wouldn’t be invented for another six or seven years. I would have had the Gmail domain first.

Stacy: Together, to gather. I like that.

Josh: Yeah, it was called ToGather. Anyway, my friend Javier ended up launching something called eDreams, which he built with another classmate, James Hare. When it went public, in 2016 or so, it was the biggest Spanish IPO ever. Javier and I are still very close friends. But he went off and did that.

I quit my job to begin writing the business plan for ToGather. I was working a hundred hours a week, so I had no time to find co-founders, raise money, or write a business plan. I had to quit and then go do all of that. And that felt incredibly scary. I had a good job, and I thought, oh my God, what are my classmates going to think?

[20:18] And this is where your husband, Uri, comes in. It’s Thanksgiving of 1998. I’ve quit my job, I’m doing my market research, and I come across a company called evite.com. They have this web-based calendar that seems to be about inviting people to events. It seems very similar to my business plan. So I write Uri, your husband, one of my best friends and also a classmate, an email with “F word, F word, F word” in the subject line, and then “F word, F word, F word” about a hundred times in the body of the email. I just found this company Evite. They seem to be doing the same thing I’m doing. Oh my God, my life is over. I can’t believe I quit my job.

Stacy: Oh, because you had already quit your job.

Josh: Oh, I’d already quit my job. I’m doing this.

Stacy: Yeah. I forgot about that.

Josh: I’ve quit my job. I’m four or five weeks into market research now, I’m writing the business plan, all the things. And Uri writes me back and says, ” Relax, for all you know, this is three people in a garage. Why don’t you reach out to them and meet them?” Which was sage advice, as I so often get from you and from Uri.

So I reached out and met them, and it turns out it was three people in a garage who were really passionate about something called Ootleworks. Ootle stood for object-oriented template language extractor. They were Stanford engineers, insanely smart and insanely talented, trying to build what today would be Mint.com, something that scrapes all your financial information and puts it in one place. They were doing odd jobs on the side, and someone wanted them to build a web-based calendar to organize their soccer league. So they built it to earn $20,000 on the side and then left it alone to go back to their Ootle thing.

I was really passionate about ToGather, but I actually thought Evite was a better brand than ToGather, and they were very talented engineers. So we met and started talking. The first thing we did was I joined them and said, “Let’s try to make Ootleworks work.” We spent a month on it, and it wasn’t going to work. And I said, I have this business plan, and I’m really excited about ToGather. I want to take Evite, rebuild it to be what the ToGather business plan is, and relaunch Evite as a way to invite people to organize events and activities.

[22:54] A huge advantage I had was that I had gone to Stanford business school. I knew people at all the different venture capital firms, and I knew how to write a business plan.

Stacy: Your former classmates were now at…

Josh: My former classmates were now two and a half years out of business school, and some had landed at venture capital firms. So I was able to write a business plan and raise some angel money, mostly from classmates of mine who just believed in me. Your reaction, Stacy, was the same as everyone else’s, which was that it sounded like the dumbest idea ever.

When I was trying to explain ToGather.com to people, I’d say, we’re going to invite you on the internet to this page, and you can see who else is coming. It’s going to be an electronic invitation. Everyone was like, I don’t understand. There was no offline corollary for it.

Stacy: The first one I got, I thought, okay, but they could have just sent an email. That’s what we did then. Send an email to 30 people and tell them about the party.

Josh: It was really hard to explain to people what this was going to be and why it was better than just sending an email. We just had to build it and prove it.

Stacy: That’s the art side, right? Just trusting your gut. You can’t quantify that.

[24:19] Josh: Yeah. And honestly, that’s another area where business school was really helpful. At the time, what was really in vogue were what were called stealth-mode startups. This goes in and out of vogue, but all my friends were starting their own companies in stealth mode. I’d ask, oh, what are you going to do? And they’d say, I won’t tell you.

I told everybody what I was doing. When I quit my job, I said, I’m starting this thing called ToGather.com. You’re going to send invites to people, and it’s going to bring them to a web page to organize the event. Because I thought to myself, no one else is crazy enough to quit their job to do this thing. If my idea is so fragile that when I tell someone about it, they’re just going to copy it and beat me, then it’s not a good idea anyway. And the benefit of talking to people, learning, and hearing their feedback makes it worth it to tell everyone what I’m doing.

I’m so happy I did that, for two reasons. One, I did learn a ton through those conversations. But also, there were many times when I wanted to quit, when I thought, oh my God, this is sure to fail. Almost everyone I talked to said, this is such a dumb idea, and I can’t believe you quit your job over this. But by that time, I’d told so many people I was doing it that the public humiliation of failure would have been so great. I thought, I have to succeed, because I can’t bear the humiliation of failure. And it was really motivating.

Stacy: I also don’t believe in stealth mode. You’re going to learn more, as you said, from the conversation. I love this. It’s so great to hear the details of the story, because I sort of know the broad strokes. You said you like to read business books. I think you have a book in you, but we can talk about that later. There are so many good nuggets. So Evite obviously was a success. I became a super user, and so did everyone we know, and the concept is still popular today. So how did that happen?

[26:40] Josh: It was a success-ish. I would say not really a success. If you were an investor in Evite, it really wasn’t a success. We raised money in what became the internet boom and the bubble, and then the bubble burst. Suddenly, if you had an internet company, nobody wanted it, you were an idiot, and the whole internet thing was a fad. By September and October of 2000, the internet was the dumbest idea ever, and anyone who had started an internet company was obviously a moron.

We ended up selling our company to Barry Diller for less than the capital we raised, so people who invested money in Evite did not get all their money back. That felt horrible to me. I also was broke. After selling Evite, I had no money, and I had just gotten married. I spent about a year trying to come up with another idea for something I wanted to start.

One of my investors was an early employee at eBay, and he kept trying to get me to join eBay. Finally, I was really out of money. It had been a year since we sold Evite, and I hadn’t started my next thing. He came to me with a really interesting job: help us get eBay into new countries. eBay had gone public by then but was a young, fast-growing company, and it was considered the perfect business model. It was going to win all of e-commerce. No one could compete with it. eBay at the time, by the way, was worth more than 10 times what Amazon was. Amazon was worth a tiny fraction of what eBay was.

Stacy: Amazon was just selling books then, pretty much.

Josh: Yes, just selling books. Everyone was like, how big can that company ever be?

Stacy: That’s a huge stamp of approval, that you lost this guy’s money and he still wanted to give you a job.

Josh: Yes. And I learned so much from being the CEO of Evite through the good days and the bad. There were great days when it was super exciting, and there were really, really rough days.

Stacy: But I say success because you built something that became really popular, and you built a brand that people knew. There is success in that.

Josh: I’m really proud. Twenty years later, 30 or 40 million people a month still use this product that a few of us built years ago. That’s pretty cool. But it didn’t feel like a success at the time. When the bubble burst and my company wasn’t valued at anything, it felt really hard. It felt really bad. But the experience of having been a CEO was so valuable to me. The idea was that no one should hire me to be the CEO of anything, so I just had to hire myself. I’m going to start my own company, hire myself as CEO, and prove to myself and then the rest of the world that I can be good at this.

[29:53] When I joined eBay, I had a really broad understanding of all the levers in business. Normally, when you join a bigger company, you’re in marketing or finance or HR, and you know your piece of the world. Developing the ability to think like a CEO and see how it all comes together is just tougher that way. I’d been a CEO and had real empathy for that role. Pretty quickly, I was able to distinguish myself at eBay, end up leading some acquisitions and then running the companies we acquired, and build a lot of value for eBay.

I joined with the job of helping launch eBay in new countries. They asked me to go to the Netherlands, where eBay Netherlands was a small and underperforming business. I identified that there was a local classifieds competitor to eBay called Marktplaats, which was like Craigslist for the Netherlands. eBay thought classifieds didn’t work. We’d faced classifieds competition in America many times, and the classifieds businesses had never succeeded. But I knew that in the Netherlands, Marktplaats was working.

I was able to convince the CEO of eBay that we should buy Marktplaats. I led the acquisition of Marktplaats, and then I ran and scaled it. Then I went and bought several other classifieds businesses, Gumtree in the UK and a few others. Even though Evite was a very small business compared to eBay, having that real CEO mindset let me speak to eBay’s senior executive team in a language they understood and actually go buy a company and run it. All of that came from the experience of having founded my own company. Running my own startup was so valuable to me.

Stacy: When I hear this, and you were very young at the time, I think, wow, you had a lot of self-confidence to have this idea, bring it to the leadership of a public company, lobby for it, lead it, and convince them you could do it. Do you think that’s innate confidence? Do you think your experience in business school helped spark that? Where does that come from?

[32:30] Josh: I definitely think the experience in business school was really helpful in giving me the toolkit. How does one pitch an idea? First, I had to pitch my idea to investors, getting people to want to fund Evite, which was really hard and really ego-busting. You go to VC after VC, and they say, I’ve heard a hundred pitches, and that was the worst pitch. You have to shake yourself off and go talk to the next one. I learned how to make a really data-driven case.

When I got to the Netherlands, my job was to give advice to the CEO of eBay Netherlands. I was sent there first as an advisor on how we could fix the business, which was going so badly. I get in a taxi at the airport in Amsterdam and start talking to the driver. He asks, why are you here? I say, I work for eBay. He says, I’ve never heard of that. I say, it’s a place where you buy and sell things on the internet. He goes, ah, like Marktplaats.

I show up at the office and ask, what is this Marktplaats company? And everyone in the office says, you’re not allowed to say that word. Management has told us that when we talk about Marktplaats, we’re just making excuses. Classifieds don’t work. You’re not allowed to say the name Marktplaats in this office. I said, okay, well, that’s nonsense. How are we going to prove to management that Marktplaats actually works?

I just did some very scrappy market research. Market research is one of the things you work on in business school, and ADAC Labs, the company I joined right out of business school, was super focused on scrappy market research. How can you very quickly get the voice of the customer? I learned so many tools at ADAC that were so useful. One of them was to use your own team for market research. I had 23 employees working for me at eBay Netherlands, and I told all of them, ” Bring three things to the office tomorrow. We’re going to sell those three things on eBay, and we’re going to sell them on Marktplaats.”

Stacy: Oh my gosh, I love that.

Josh: In one week, we had data showing that it was much faster and cheaper to sell on Marktplaats, and the items sold better. We did these really scrappy things, and in a matter of weeks, I had real data I could present to management: it takes this long on average to sell an item on eBay, and you only get this price. If you list it on Marktplaats, it takes less time and sells for more money. If you’re a customer in the Netherlands, you should use our competitor most of the time. That kind of data was very compelling to management.

[35:21] Stacy: I’m sure. And I remember you then went to the UK. Is that right?

Josh: What happened was I moved to the Netherlands. At first they sent me as an advisor, and then they said, okay, you should run the whole thing. We like your point of view. We want you to run eBay Netherlands. I said the way to fix the Netherlands is to buy Marktplaats and be in the classifieds business. They said, okay, go buy Marktplaats and then run it. And while you’re at it, buy all the other classifieds sites in Europe. Let’s win Europe.

Because my first job out of business school was buying a bunch of small companies, I had done M&A and knew how to buy companies. So I went and bought Gumtree, LoQUo, and Marktplaats, and then ran those three classifieds businesses. That ended up being really hard but really exciting. Meg Whitman was the CEO of eBay at the time, and she said, ” Buy Marktplaats. I don’t care about the price. We have to own it.”

Stacy: You did a good job convincing.

Josh: Meg is fantastic. Once she’s convinced, she’s convinced. At that point, she’s very competitive, and she wants to win. We paid a lot of money for Marktplaats.

The shareholders of the largest newspaper company in the Netherlands got really mad at them, because newspapers at the time made all their money on classifieds. The shareholders of this company, De Telegraaf, said, ” How could you let eBay buy Marktplaats? You should have bought Marktplaats.”

So De Telegraaf put all of its resources into building a competitor to Marktplaats. They made a better online classifieds site than ours, and they made it completely free, whereas Marktplaats charged money. They owned the biggest newspapers, radio stations, and television stations in the Netherlands, and they took all of their unsold advertising inventory and used it to promote their competitor, which was called Speurders. Every time you turned on the TV or the radio or opened a newspaper, all you saw were ads for Speurders, Speurders, Speurders.

[38:01] A year after we bought Marktplaats, Speurders had launched, and it was growing like crazy. I had to fly back to eBay headquarters in San Jose, California, and tell Meg, ” Remember that company we paid all that money for? Well, Speurders is growing much faster than Marktplaats, and they’re going to win if we’re not careful.” That was the worst meeting of my life. I felt so horrible.

I got on the plane to fly back to the Netherlands, thinking my whole career depends on this next year of my life. How are we going to beat Speurders? It was so stressful. I was so scared, but it was also so exciting. By the time I landed in Amsterdam, I’d decided there were six things we had to win at. We had to be better than Speurders at this, this, this, and this.

I called my team into the office and said, ” Everything we’ve talked about- career development, work-life- none of that matters. For the next year, the only thing that matters is beating Speurders. Martijn, you own this one.” I gave each of six people on the team ownership of one of those six things. “You have two weeks. Come back to me with a plan for how we’re going to win.”

The team came up with great plans, really exciting and really ambitious. Everyone had clear ownership of their thing. Over the next year and a half, we executed like crazy, and Speurders ended up exiting the market completely. Marktplaats grew a ton and got a lot bigger. What felt like the scariest moment of my life turned into the most exciting victory. That was really how I made my name within eBay. Buying the company was fine, but winning against tough competition was how I made my name.

Then eBay bought a company called Shopping.com. They’d spent $635 million buying it, and once they bought it, they realized it was a mess. They asked me to move back to California and take over Shopping.com. A year and a half into that, they’d also bought Skype, and Skype was a total mess. They asked me to move back to Europe and turn around Skype. So I did a Shopping.com turnaround, and then Skype, which they paid $3 billion for. Over time, I’m now running a company someone’s paid $3 billion for and doing a turnaround of that. That’s how I worked my way up.

[40:37] Stacy: I just envision you going into a $3 billion company, and it’s a mess. How do you navigate that? How do you untangle it? How do you get your arms around the team? What did you draw on to find your way through?

Josh: Bringing this back to business school, there’s a class at Stanford called Touchy Feely. I think the actual title is something like Human Interaction, but everyone calls it Touchy Feely. Most people take it, and most people say it was the most important class in business school. I would agree with that.

It’s a weird class. I forget if there were nine of us, but it’s a relatively small group. You meet twice a week for three hours per session, and there’s no agenda. You just go around the room and talk, and each person is supposed to be exceptionally honest about sharing what they’re actually thinking. I’ll never forget that in the very first session, someone said, I’ve come to the realization that I’m gay. It’s a big realization in my life. And the very next person said, I feel like you just said that for attention. That felt like a really attention-seeking thing. I thought, oh my God. I can’t believe that person just said that.

Stacy: I don’t think that would fly in 2025.

Josh: It barely flew then. I thought, holy cow, that is a form of honesty I’ve never experienced. The class was amazing at teaching me how other people perceive me, which can be very different from how I think of myself. I would say something, and then other people would share, ” Here’s how I perceived what you just said.” I realized the gap between what you say and how you’re heard can be so large. The class really helped me close that gap, and it also really helped me get better at asking good questions.

[42:39] There was another really important experience. I took a leadership development class while I was at eBay that was super helpful to me. The main thing I learned from it was that leadership requires followership. If you want to lead, people need to want to follow. People are rarely convinced by someone getting up and lecturing them about why something’s a good idea. They’re more convinced by someone asking thoughtful questions, deeply understanding the team’s point of view, reflecting it back, and then offering a thoughtful, clear direction of what success looks like.

When I arrived at Skype, for example, the strategy was unclear, the culture was very combative, and the structure was very messy. I spent my first weeks just asking the team a lot of questions about their points of view on the strategy, on the direction, and on roles, structure, and clarity. From that, I was able to say, I’ve heard a lot based on all of your input. Here’s what I think, and here’s where we’re going. People were excited to follow that, because I think they felt heard.

Stacy: That is amazing advice, and it’s so true. People want to feel heard and valued and part of it, not just spoken at. So good. I need to file that one away. You have so many great experiences, but let’s move through what happened with Skype, and then you went to American Express.

[44:36] Josh: With Skype, we pivoted the company. When I got there, it was free phone calls. Skype was a utility that let you make phone calls to other people for free, and growth had stalled. There was a set of options for what we could do, and the exciting next opportunity, it felt to me, was video: the idea that you could make a video call. Suddenly many people had broadband internet access, and computers were starting to ship with cameras on them.

We had four or five different options, and this one was certainly more art than science. It just felt like, let’s go all in on video calling and see if we can make it popular and mainstream. So we took Skype, an application that hundreds of millions of people used, but almost exclusively in Europe and Asia and almost exclusively for phone calls, and pivoted the company to make video calling front and center. In doing that, we got tens of millions of people excited about video calls.

We made Skype relevant in the U.S. In the U.S., people didn’t feel like they needed free phone calls. Calling people in the U.S. was already free, and most Americans didn’t know anyone outside the U.S. So Americans felt they didn’t need Skype until we pivoted to video calling. Then it was, that’s cool. Grandma wants to have a video call with her grandchild, and Skype is the way to do it. We got a lot of grandparents onto the internet who didn’t even need the internet before this.

The timeframe, by the way, is 2008 to 2010. That’s when I was leading Skype. So we pivoted Skype to be about video calling. There was this brand-new device called the iPhone that had just launched, and we launched Skype on the iPhone, and it was the second most popular app on the iPhone for some time. That was also really controversial inside Skype. Most people did not want to launch Skype on the iPhone, because they felt Skype is a communications app and the iPhone is a communications device, so why do you need a phone within a phone? But I really felt the iPhone was the platform of the future and we needed to be on it. The launch of the iPhone and Skype’s success on it turned out to be a really big unlock for us.

So, a very good experience at Skype. Then I joined American Express to run the U.S. business. They were looking for someone deeply rooted in the tech industry to help modernize American Express and make it a more tech-first company. For me, the opportunity to work at that kind of scale was exciting. I was running a $13 billion business, $13 billion of revenue, and it felt exciting to test myself at that scale. I spent four and a half years at American Express. It was great. I learned a ton. It was a really good experience.

[48:01] Stacy: That was probably a different experience than you’d had. Did you have to adjust your leadership style in that role, in what feels like a more corporate environment?

Josh: The culture was so different from anything I was used to. Most people at American Express joined straight out of undergrad or business school and then spent 30 years there. No one arrived at Amex thinking they were going to spend 30 years there. They arrived thinking, I’m going to spend three or four years here and then go do something else. But Amex did a great job of giving people career adventure. They moved people from marketing to finance to HR, so people felt they were getting a lot of diversity of experience.

I don’t want to make generalizations, and the team at Amex is so good. But one thing I observed in people who’d been there for some time, and one thing I would encourage people to do, is to keep a strong sense of agency, a sense that you can have good market value in a lot of different places. Once people got very, very senior at American Express, it felt like they were competing only for other jobs at American Express, and internal politics could become more of a focus than competing on the outside for customers. That was new for me. But it was a great experience at Amex. I learned a ton, and it was really valuable.

Then I joined the board of Etsy. It had gone public, but it was struggling. We had activists and takeover offers, and Etsy was in bad shape. It had stopped growing and wasn’t profitable. I got a phone call one day: the board had voted, behind my back and without telling me, and elected me CEO. I was starting on Tuesday, and they didn’t want to hear any back talk. I’d actually already told the board that I wasn’t interested in the CEO job and didn’t want it, but they elected me CEO anyway. That turned out to be an incredibly fulfilling experience, and I’m so happy the board did that. I spent nine years there.

Stacy: I’m sure they are too, because you did a good job.

Josh: We were able to unlock a ton of value and make Etsy much bigger and a household name.

[50:33] Stacy: How did you approach that? You said it was a mess, and they brought you in to rescue it. What was day one? What was your first order of business? I’m so fascinated, because I think about these companies as tangled messes. How do you decide which lever to pull first?

Josh: I think the most important thing is to first define success for the team. What does success look like? Until you’ve done that, you can’t really do anything. So define success, and then you can engage the team on how to get there. What does it look like to win the war? Once we say this is what winning looks like, then we can ask, what are the most important battles? What are the fewest battles we need to fight in order to win the war? And once we’ve agreed on those, then you can talk about org structure. If these are the battles we need to win, here’s the organizational structure. I need a leader on each of these.

At Etsy, I arrived knowing very few things. I’d only been on the board for six months. But I had conviction about two things, really. The first was that success was defined by growing gross merchandise sales. That’s Etsy’s term for how much our sellers sold. If our sellers are selling more, they’re happy. It means buyers are finding more things on Etsy to buy, so the size of the pie is growing. So the North Star was, how do we make gross merchandise sales grow, and grow much faster? Gross merchandise sales had stopped growing. If they grow, revenue will grow and profits will come, but that’s the measure of our customers winning.

So I said the metric that matters is gross merchandise sales; we’ve got to get it growing, and I want it to grow by more than 20% a year. That felt like a lot at the time. Gross merchandise sales were growing 3% or 4%. And I said, I think we can make Etsy $10 billion of gross merchandise sales annually someday. Etsy was selling about $2 billion at the time, and people thought that was kind of crazy.

[52:51] Then I challenged the team: what are the fewest things we need to do to get gross merchandise sales growing 20%? What are your best ideas? I didn’t have any ideas for how to do it, but the team had been working there for quite some time, and I was brand new. Bring me your best ideas. And by the way, if your idea isn’t going to add at least $20 million of annualized sales to Etsy, I don’t even want to hear it. I’m not saying I’ll do it if it does add $20 million. I’m saying I won’t even think about it if it doesn’t. As a result, we killed 90% of the projects we were working on.

Stacy: Oh, projects that were already in process?

Josh: Already in flight. We killed almost all of them and doubled down on a tiny handful that had the most potential to drive growth in the near term. Then we reorganized the company around those few things. What is the cleanest, leanest org structure to focus on these few initiatives? I want one owner for every initiative, and that owner needs to have all the levers they need to succeed, so I can hold that person accountable.

In my fifth week at the company, we did a massive reorg where we said, here are the few things that matter, and here’s the new org chart to support that strategy. We changed almost everybody’s job. It was very traumatic for the team, but almost immediately, within a very short time, we were starting to grow again. We were just moving so much faster. That was the start of unlocking a ton of growth.

Stacy: That’s amazing. How did you manage morale through that? You were this new guy coming in, traumatizing everyone. How did you get them to really believe and fall in line?

[55:55] Josh: Not everybody did, honestly. Etsy’s sense of itself at the time was that we’re doing okay. We’re not growing, and the stock price has fallen by 60 or 70 percent, but that’s okay because we’re doing other things we feel good about. The first step was defining success for the team: we are not serving our sellers.

I think the most important thing is that people want to be part of something much bigger than themselves. If you talk to people about stock price or whatever, it’s never motivating. What is the mission we’re on that’s uniquely important? When I joined Etsy, there were 2 million sellers. The first thing I said to the team was, “There are 2 million people who wake up every day counting on Etsy to succeed. You want to know why our politics are so fraught? It’s because it’s really hard for people out there.”

At the time, there were about 1,000 people working for Etsy. We had yoga breathing rooms, farm-to-table food, and 401(k) plans. The sellers don’t have any of that. They’re trying to put food on the table, and they’re counting on this team to bring our A game. We have a job to do that’s much bigger than ourselves, and we need to be prepared to make ourselves very uncomfortable in order to serve them. It’s not the reverse.

We’re going to do a lot of really hard things, and they’re going to feel really hard. If we succeed, we will cover ourselves in glory and feel great about it for the rest of our lives. We’ll tell our children about this moment. Everyone thinks we’re going to fail. The whole world thinks we’re going to fail. Maybe we will. But if we succeed, wow, it’s going to be amazing. In the meantime, I promise it’s going to be hard. And if you’re not up for it, I really need you to quit, because you’re in the way.

And tons of people quit. Every day I’d stand up with my executive team, and agenda item number one was who quit today. There’d be some engineer, and it was, Mary is the only person who knows this part of the code base. How are we going to get by without her? But it turns out we always found a way. What we were left with was missionaries, not mercenaries: people who genuinely believed in this bigger mission.

And for the people who stayed while we were changing everybody’s job and making a lot of changes, there was a real opportunity. We gave a lot of responsibility to people: what’s your idea to make this company grow a lot more? If you have a good idea, we’ll give you a chance to lead it, empower you, and then hold you accountable. That really worked.

[57:53] It was the same at Skype. When I came into Skype, there was so much talk about how eBay had overpaid for it, how it wasn’t really worth that much, how it was dysfunctional and wasn’t growing anymore. What I felt about Skype was that the brand was really powerful, because it allowed you to be with someone when you can’t be in the same room. That’s where the pivot to video came from: the best way to be with someone when you can’t be in the same room is to be on video together.

I held weekly staff meetings for everyone at Skype, and I would start every one by bringing in a customer to tell the story of why Skype was really important to them. I remember service members serving in the Iraq War would Skype in and talk about how they were able to maintain a relationship with their spouse and kids back home, even while serving in the desert in Iraq, because of Skype.

We had people who worked for the UN High Commissioner for Refugees, working in refugee camps in Darfur in really difficult circumstances, Skype in and talk about what Skype meant to them. That made the mission of Skype come to life for the team and made them realize there are people out there for whom we serve a really important role, and we’ve got to be willing to work hard and do the hard things in order to serve them. I think that higher purpose you’re in service of is what gets people truly motivated.

Stacy: Right, right. It’s not just a tech tool, a gadget.

Josh: Right. Here’s why the work you do matters.

Stacy: I love that.

Josh: Here’s why it’s worth coming in on a Saturday.

Stacy: Right. So good. I’m learning so much from this conversation. I’m going to watch it again and take notes. It’s interesting to me that Etsy and eBay are both marketplaces. Did you take lessons from eBay that you applied at Etsy?

Josh: So many. One of the most important was that at eBay, during my tenure, we told ourselves we were 50/50 focused on serving the seller and serving the buyer. We’d have roughly half our resources serving sellers and half serving buyers, because they’re both our customers. But in truth, we spent a lot more time and energy focused on our sellers, because they’re the ones who pay the bills. They pay the fees, and they’re deeply invested in the platform. If they’re unhappy, they’re going to call, they’re going to write, they’re going to make their voice heard, whereas buyers who aren’t happy just go away. They’re invisible in a lot of ways.

[01:00:41] But in fact, what our sellers really needed was buyers and sales. They’ve hired us to bring them buyers and sales. So the right thing to do is to focus a lot on buyers and on delivering a great buyer experience, which sometimes makes your sellers mad. For example, sellers like to have complete control over pricing and shipping, and for some of your sellers, that’s a business model. They’ll price the item very cheap, so when people look at a range of items, this is the really cheap one. They add it to their cart, and only then, in the cart, do they see that this particular seller makes all their profit on shipping and charges a ton for it. That’s a pricing strategy: I’m going to undercharge for the item.

Stacy: One dollar, and then shipping is 30.

Josh: Right. That can be a very successful strategy for a seller, but it’s a terrible buyer experience. And what that buyer rarely does is go back and look for a different item from a different seller. What they usually do is say, oh, eBay is terrible. They overcharge for shipping. So all of the other sellers have been damaged by this one seller’s pricing strategy.

Enforcing some rules of the road, deciding what your brand stands for with buyers and insisting that your sellers live up to that brand standard, makes you unpopular with different segments of your sellers. But it is in the collective interest of your sellers as a whole for the brand to stand for something and to have some basic brand standards. That requires courage as the CEO, because on any given day, a lot of sellers are going to say mean things about you. You’ve just got to have the conviction that it’s the right thing to do.

I took that lesson with me to Etsy, where I saw that most of our effort was going into building features our sellers had requested: very edge-case, minor features that weren’t making the buyer experience better. What we really needed was to invest in the buyer experience and enforce more brand standards for our sellers. In doing that, we made the Etsy marketplace a lot more accessible and a lot more popular, and we brought in a lot more buyers, which meant that over time we could serve a lot more sellers and help them sell more. But I was unpopular with segments of our sellers at many different stages along our growth trajectory in order to get there.

[01:03:27] Stacy: Amazing. So interesting. So here we are today. You’re chair of Etsy, so you’re not in the weeds day to day. When you look back, how do you define success today?

Josh: For me, it’s purpose and impact. I would say it’s always been, what can I do that my kids would be proud of me for? When I first started out of college, I didn’t have kids, but going to work for a senator in public policy was about, what can I do so that when my time on this planet is over, I’ve left a positive impact I can be proud of? That’s always been it. I’ve found that doing that in the private sector has turned out to be a very rewarding path for me. It’s just faster to get things done, and in my experience, it’s often more effective to do it in the private sector. But that’s how I’ve tended to measure success.

Stacy: Looking back on your path, what would you say are the biggest takeaways from your MBA? Maybe some served you in the beginning, along the way, and still now, or maybe you’ve pulled on different things during the journey.

Josh: I do think investing in getting to know my classmates was super valuable. Yes, they might someday end up in a place where that professional network is interesting. But more than that, it was learning what the different options in life are. There are so many options in life. Meeting people who’ve lived different lives in different places, doing different things, and who see the world in different ways was so valuable. Investing time in really getting to know this incredible collection of people, curated to be very diverse, was a really good experience.

And my career, in hindsight, you might look at it and say, oh, it all makes sense. But I promise you that at the time it didn’t. At almost every point in my career trajectory, I’ve made a very unconventional choice. When I took the job at Skype, everyone told me not to do it. They said it would be a terrible idea. In fact, the only reason I got offered the job was that they spent three or four months looking for a qualified CEO and couldn’t find a single one who would take it. The company looked like such a mess.

[01:06:13] I’ve applied a few rules when I’m thinking about career moves. Am I going to work with really interesting people from whom I can learn? Am I going to do something where, if we succeed, we’ve accomplished something really great together? And importantly, the third criterion: if we fail, am I no worse off than I was when I started? Will I have at least as many career options as I did when I started? Those three rules collectively have served me really well.

Stacy: I just love the way you break things down. I’ve obviously known you for a long time, and you’re a very calm, steady person. You’ve experienced a lot of stress professionally, but I’ve never sensed that from you. You talk more to Uri, my husband, about the business stuff. But talking to you now, I love the way you’re able to look at a big problem, break it down, think it through, and make a very clear structure out of it. I think it’s amazing, and I want that skill.

Josh: Thanks for saying that. I do think groupthink is a huge thing. It’s human nature: conventional wisdom is X, so everyone thinks X. Oftentimes conventional wisdom is what it is because it’s actually the right answer. But not always. Sometimes people are wrong, and that’s where the huge value unlock is. When most people think the right answer is this, but you have conviction that it’s that, there’s huge value in that, especially in business, in the private sector.

Stacy: And it just seems like at every turn, you were able to unlock that key thing. Maybe there were 100 opportunities, but you found at least one of them, believed in it, ran with it, and it made a huge difference. So, proud of you.

Josh: There have been a lot of opportunities presented to me where most people think it’s a bad opportunity, and I agree, right? The thing was picking the one where I thought people were missing something. I think Skype actually has tons of potential. I think Etsy really has tons. When I took over Etsy, most people thought it was as big as it was ever going to be. It was a really niche thing. Proving people wrong is part of the fun of it.

[01:08:50] Stacy: Great. Well, that is a perfect place to wrap, unless you have any final words of wisdom or anything you want to share. Otherwise, I’m just so appreciative.

Josh: Only that I’m a big Stacy Blackman fan, your firm does great things, and people will be smart to take your advice and hire your firm and all the things.

Stacy: Thank you, Josh. I appreciate that. I’m really grateful for your time today, and I loved hearing more about your story and the details. So thank you. Talk soon.