The Exchanges

Q I mean, you're just teasing people who are listening on podcasts and not watching TikToks, but I want to start today with a little on your, I mean, 25 years plus now in the industry. How did you make your way first into the tech industry, and then kind of skipping a little bit, a little bit, how did you come to be CEO of Yahoo most recently?

A I'll give you the, um, the, the quick, uh, Wikipedia, you know, origin story. So I, I had never had a real job. I wound up in law school, uh, which worked. I met my wife. I hated it. I switched to business school and wound up. This is the middle of, of the internet and, uh, industry starting. I wound up as a product manager, as a summer job, got really cocky with a couple of classmates, started a company out of school. By the day we graduated, we already had a couple million in funding and a few million users of our website, you know, at the time, uh, and had the full web one point. Oh, right. Uh, we were, we raised fifty million dollars. We're going to go public. And then we crashed like you wouldn't believe with the crash. We sold what was left to ask Jeeves, uh, which is pretty much the only company that wanted us. Uh, I got really lucky and they hired me as the head of product there. And we went on, I think probably the best turnaround run of the 2000. We fit the X that stock. We became a leading innovator in the space with a brand that, you know, was, uh, not that, you know, popular and kind of the poster child of the crash. We sold it to IEC and I became CEO as part of that transition. I wound up working for Barry Diller for many years. Left and did another startup, uh, Bill Gurley and Jeff Yang were my investors. It was called Clicker. It was internet TV guide or search …

AI assessment note: “I'll give you the, um, the, the quick, uh, Wikipedia, you know, origin story.”

Q How many direct reports do you have, Jim?

A It'll come and go. So the proper amount for, for my job is probably somewhere between 10 to 12. And over time, these general managers, you'll wind up with some, what I, you know, refer to as, you know, nicknamed super GMs, where you'll have GMs who have multiple GMs reporting to them in groups or segments that make sense. Cause this is a portfolio play. It's a conglomerate play. And at CBS Interactive, when I inherited multiple former public companies and the CBS assets, my first thing, I was, I was like a pig in slop as a product guy, right? I was like, oh, I can't wait to dig in on fantasy football and on CNET and on CBS news and last FM and all these things, but the reality, and so I had 25 direct reports and I got just smacked in the face the first year trying to keep it all together. So what I really, what we, what we created was a model that we called federal and state. Where you create, you know, essentially governors of each of these businesses, sometimes in groups, and you, you give them the, the operational mandate to run their own business reporting into me. And my job is to, you know, hire and fire and manage them and work with them on their plans. And then at central or federal, you know, our job is to provide leverage Uh, you know, as cheaply as possible, right back into those businesses and let them run.

AI assessment note: “the proper amount for, for my job is probably somewhere between 10 to 12”

Q Would you ever like to take the name off and put on a new name?

A No. Well, look, one thing to remember is it was just put back on, um, you know, this company is also AOL. So we, we also own AOL, which is still very profitable and does a lot of free cash flow. So again, I look at this as, as, as what you've inherited. And, and I actually think putting the Yahoo name back on it on September first of last year, when Apollo closed the deal was one of the luckiest things I inherited. You you're speaking as somebody from the industry, right? And, and especially in VC or in Silicon Valley, they can be very cynical about Yahoo given the history. The average user of those nine hundred million users actually has a lot of brand preference for Yahoo. It's something we can really build off of, especially if we can do a much better job at product. There's something about it that people do love. And as you know, there's not always something about the big trillion dollar companies right now that everybody loves. So I actually think the first step here is, is fix the org and fix the product. But if we can do that, I think there's a lot of growth for the brand that's possible. And I think it's a strength, not a weakness, even though I understand why you're asking the question.

AI assessment note: “No. Well, look, one thing to remember is it was just put back on”

Q Now, on the turnaround side, the thing that's just striking bluntly when we look at your career is the amount of successful turnarounds you've had. I mean, it's very difficult to have one successful turnaround. You've had, you know, four now? Well, Yahoo will be your fourth, I think. Um, my question to you is, what are the commonalities in what you have done that's worked first?

A Yeah, you know, I've learned over time that, uh, you do have, uh, You know how they say a house has great bones, you know, for these shows where they renovate houses. You, you can't, you do have to start with, with good bones, uh, on the house. And for me, the first one of those, or the commonalities between, you know, the, these situations is you, you have a lot of traffic is, is one big thing that helps. Uh, you have a brand that's maybe seen better days, but you can do something with, or the very least is well known. Uh, you have underdeveloped, Products, maybe bad products, but for some reason they've been sticky in their own way. I can talk about those. And then you have organizations that, you know, probably have not been optimized, whether that's great people or they have the wrong structure in place. And again, I've seen all of those. They usually all exist at once, uh, in every one that I've been part of. But if I have traffic and I have a brand that's known and I have products that people are loyal to, even if they've, you know, it's been a while since they've been optimized properly. Then I can do the rest and, you know, bringing great people, getting the roadmap, going the right way. If you get those things, well, then the brand has a chance to do things again and you can build on that traffic. And, uh, you know, in every case that that's what I've inherited.

AI assessment note: “the commonalities between, you know, the, these situations is you, you have a lot of traffic”

Q specifically on your leadership, because, you know, it was Reid at Apollo who said, you are, I, I hope I'm allowed to say this, and he said, you're the best CEO he's ever worked with. That's quite a, that's quite a statement. Um, So let's talk about performance and leadership. When we think about high performance in business, what does high performance mean to you when I say those words?

A You know, I went to UCLA, uh, and there's a famous basketball coach in the U S who was the most famous basketball coach, I think in history named John Wooden. And he had the saying that was never mistake activity for achievement. And, you know, I think that High performance is understanding what achievement means. You know, what are you really trying to do? And, um, and really putting things in place to go make that happen. Um, the first thing always that starts with is a high performing team, right? You can't do everything yourself, especially at scale. And so for me, it really starts with people and putting a high performing team together, I think is one of my, has become one of my core competencies. Um, and And I really, when I'm hiring people, I really hire for four things. The first is I really want domain experts, right? I do not want people who are faking it till they make it. Uh, and if you are an expert, you tend to be able to understand what one looks like. Um, and it always starts there. The second is I want people with high EQ. Uh, high IQ is easy to get. People with high EQ who, you know, are good teammates. They, they, You know, they don't view things as a zero, zero sum game against the other people in the company. You know, they understand that life is dramatic enough. They don't need to create drama. Um, they understand why diversity is important. You don't hav…

AI assessment note: “High performance is understanding what achievement means. You know, what are you really trying to do”

Q Would you ever like to take the name off and put on a new name?

A No. Well, look, one thing to remember is it was just put back on, um, you know, this company is also AOL. So we, we also own AOL, which is still very profitable and does a lot of free cash flow. So again, I look at this as, as, as what you've inherited. And, and I actually think putting the Yahoo name back on it on September first of last year, when Apollo closed the deal was one of the luckiest things I inherited. You you're speaking as somebody from the industry, right? And, and especially in VC or in Silicon Valley, they can be very cynical about Yahoo given the history. The average user of those nine hundred million users actually has a lot of brand preference for Yahoo. It's something we can really build off of, especially if we can do a much better job at product. There's something about it that people do love. And as you know, there's not always something about the big trillion dollar companies right now that everybody loves. So I actually think the first step here is, is fix the org and fix the product. But if we can do that, I think there's a lot of growth for the brand that's possible. And I think it's a strength, not a weakness, even though I understand why you're asking the question.

AI assessment note: “No. Well, look, one thing to remember is it was just put back on”

Q specifically on your leadership, because, you know, it was Reid at Apollo who said, you are, I, I hope I'm allowed to say this, and he said, you're the best CEO he's ever worked with. That's quite a, that's quite a statement. Um, So let's talk about performance and leadership. When we think about high performance in business, what does high performance mean to you when I say those words?

A You know, I went to UCLA, uh, and there's a famous basketball coach in the U S who was the most famous basketball coach, I think in history named John Wooden. And he had the saying that was never mistake activity for achievement. And, you know, I think that High performance is understanding what achievement means. You know, what are you really trying to do? And, um, and really putting things in place to go make that happen. Um, the first thing always that starts with is a high performing team, right? You can't do everything yourself, especially at scale. And so for me, it really starts with people and putting a high performing team together, I think is one of my, has become one of my core competencies. Um, and And I really, when I'm hiring people, I really hire for four things. The first is I really want domain experts, right? I do not want people who are faking it till they make it. Uh, and if you are an expert, you tend to be able to understand what one looks like. Um, and it always starts there. The second is I want people with high EQ. Uh, high IQ is easy to get. People with high EQ who, you know, are good teammates. They, they, You know, they don't view things as a zero, zero sum game against the other people in the company. You know, they understand that life is dramatic enough. They don't need to create drama. Um, they understand why diversity is important. You don't hav…

AI assessment note: “High performance is understanding what achievement means. You know, what are you really trying to do”

Q Now, on the turnaround side, the thing that's just striking bluntly when we look at your career is the amount of successful turnarounds you've had. I mean, it's very difficult to have one successful turnaround. You've had, you know, four now? Well, Yahoo will be your fourth, I think. Um, my question to you is, what are the commonalities in what you have done that's worked first?

A Yeah, you know, I've learned over time that, uh, you do have, uh, You know how they say a house has great bones, you know, for these shows where they renovate houses. You, you can't, you do have to start with, with good bones, uh, on the house. And for me, the first one of those, or the commonalities between, you know, the, these situations is you, you have a lot of traffic is, is one big thing that helps. Uh, you have a brand that's maybe seen better days, but you can do something with, or the very least is well known. Uh, you have underdeveloped, Products, maybe bad products, but for some reason they've been sticky in their own way. I can talk about those. And then you have organizations that, you know, probably have not been optimized, whether that's great people or they have the wrong structure in place. And again, I've seen all of those. They usually all exist at once, uh, in every one that I've been part of. But if I have traffic and I have a brand that's known and I have products that people are loyal to, even if they've, you know, it's been a while since they've been optimized properly. Then I can do the rest and, you know, bringing great people, getting the roadmap, going the right way. If you get those things, well, then the brand has a chance to do things again and you can build on that traffic. And, uh, you know, in every case that that's what I've inherited.

AI assessment note: “the commonalities between, you know, the, these situations is you, you have a lot of traffic”

Q What, what three traits would you most like your children to adopt?

A Oh, wow. Um, well, I'd say sense of humor. I think my wife would kill me if I didn't say that one. She'd, she'd, she'd say they'd better be, they'd better be fricking funny. Uh, hunger, you know, have like a, not like a business hunger, but just always be hungry for the next experience or milestone or album to listen to or place to visit. You know, I, the last thing I ever want to hear is my kids saying that they're bored. Um, I, I, I, I look at this as we're, you know, We're stuck in this rock floating in space, you know, millions of light years from the next closest rock, which is why I don't understand why Elon wants to focus on Mars. It's like, where are you going to go next? There's not that many places. Uh, we got to fix this place. Uh, so then, so then the last was just, I just hope that they're joyful. You know, they find their bliss and that they enjoy their time on this, this floating rock here in space.

AI assessment note: “I'd say sense of humor... hunger... the last was just, I just hope that they're joyful.”

Q Can I ask you Jim, do you have a chip on your shoulder still?

A Yeah. And I think a lot of the great people do. I mean, I don't, I think I do in a, um, a negative way. You know, I, I think the chip is, is always, Um, wanted to prove myself, but also I, I've, I've just grown to like situations where we do things that surprise people, where we turn the tables and make our competitors jealous of us, uh, where we build great teams who love being there and the word gets out. Like, you know, that's where I should go work. I remember it ask, you know, we were in Oakland and Berkeley in the middle of the dot com, you know, the, The 2000, we went from, you know, layoffs and, and not being respected to people commuting across the bridge to come to Oakland to work for us because things are going so well and people respected us and that, you know, you talk about running towards something, you know, that, that, that innovation and growth from the ashes that we were able to do there. And I've done it now multiple places. Uh, you know, whether it's growing the business or innovating and leading the industry in innovation, like those are the things I just love doing and well, and it's addicting.

AI assessment note: “Yeah. And I think a lot of the great people do.”

Q What's the hardest element of your role with Yahoo today?

A Or just changing the mindset of people takes a lot of time that some of my team will laugh if they hear me say this, but I've, I've said a few times, I wish you could have been with me at prior companies to understand what this looks like and how it goes well and, and how you're going to feel and, and, and why we won and, and how great it was to be part of that team. You know, every time you do this, You're starting over. It's not as easy as 11 and Stranger Things being able to go back in the past and, and, you know, see, see back, you know, put your finger on someone's forehead and see what it was like. You know, you, they kind of have to live that experience and it's, it's hard to be patient all the time to, to bring a new team along to that. You just have to have faith. You'll get there.

AI assessment note: “changing the mindset of people takes a lot of time”

Q Hmm. You should be a love coach, Jim. There we go. We could, we could do a weekly session. Uh, a final one. What are the next five years for you and for Yahoo? If we have this conversation in 20, 27, where would you like to be?

A Well, I think the ideal is that we're public company again, that we've spent this time as a private company. And now with the market being very, very different than six months ago, let alone the last 13 years, that we have the ability to retrench Off, you know, off the, uh, off the radar a little bit and can build this thing up the right way and make the changes we need to make, you know, whether that's acquiring or selling or what, you know, whatever we're going to do and come out the other side of that as a company that, that really can think long-term about being a public company again, you know, not in that position where you're trying to make quarters and do unholy things to, to do it. Um, You know, that, that's the, that's the optimal for where we want to take Yahoo. But again, There's, there's so much coming up here. Right. And, uh, and, and again, it's, it's, it's, um, I think about this quarter by quarter right now. We can't, can't think that far ahead just yet.

AI assessment note: “the ideal is that we're public company again”

Q Can I ask you Jim, do you have a chip on your shoulder still?

A Yeah. And I think a lot of the great people do. I mean, I don't, I think I do in a, um, a negative way. You know, I, I think the chip is, is always, Um, wanted to prove myself, but also I, I've, I've just grown to like situations where we do things that surprise people, where we turn the tables and make our competitors jealous of us, uh, where we build great teams who love being there and the word gets out. Like, you know, that's where I should go work. I remember it ask, you know, we were in Oakland and Berkeley in the middle of the dot com, you know, the, The 2000, we went from, you know, layoffs and, and not being respected to people commuting across the bridge to come to Oakland to work for us because things are going so well and people respected us and that, you know, you talk about running towards something, you know, that, that, that innovation and growth from the ashes that we were able to do there. And I've done it now multiple places. Uh, you know, whether it's growing the business or innovating and leading the industry in innovation, like those are the things I just love doing and well, and it's addicting.

AI assessment note: “Yeah. And I think a lot of the great people do.”

Q What do you know now that you wish you'd known way back in 1999 with the first company? What would you tell yourself? When you were starting out in this business?

A Wow. Well, I'd go back further to in 1993 when I graduated UCLA and I would have just said, just go get a job at an internet company and just trust that you're gonna be good at it. Cause I, I didn't know what I wanted to do. You know, my dad was a small town lawyer, you know, not a big corporate lawyer. My mom was a teacher at my high school. I just didn't have any background in, in business. And, uh, so I went to law school and, you know, and I met my wife there, which is the best thing. We've been married for 25 years, which makes it even weirder that I ran Tinder for that period of time, because I was the last person who was ever going to use it. But, um, yeah, I would have, I would have just gone back to that point in time and just shoved me straight into Yahoo at the beginning instead of, you know, the way it turned out. But, you know, life, life finds a way, right?

AI assessment note: “I would have just said, just go get a job at an internet company”

Q I'm worried about, and I always advise founders against, is multiple cuts. You know, cut deep and do it once, but don't do multiple rounds of layoffs. That's really hard. How do you know how much to cut? Is it 20%? Is it 25%? Like, how would you advise a portfolio company if it was me saying, you've got 12 months, Do I literally cut 50%? How do I know?

A You know, I mean this very specifically, not to change the, the, the way to think about this. You cannot possibly know the answer to that unless you're in that specific company. And we can talk more about this when you think about how to fix a company or how to take one over. And, and mistakes people make when they do that, you know, coming in thinking they know everything from the outside. I truly believe a rule of thumb on this situation does not exist. And I also think that if you've built off, you know, uh, trust and credibility in an authentic way with your team, then, you know, the one cut versus different cuts. I mean, that, that isn't true either, right? Because you're getting different information at different times. I think you have to make the best decision you can at that time. Now, The thing you need to be careful of is not to underestimate because you've only lived through 13 years of growth and haven't been through all these crashes, uh, you know, underestimating how long this could last or estimating how harsh it could be. And, you know, I heard Brian Chesky speak recently on, on the cuts he made at Airbnb, uh, and, you know, during, you know, the initial, uh, COVID crash in 2020, And two things happened, right? One is they, they, they did what they needed to do balance sheet wise. The second was they actually discovered they were a better company when they were…

AI assessment note: “I truly believe a rule of thumb on this situation does not exist.”

Q of core traits. The thing that I find challenging is bluntly unpacking them and discovering them. Um, you said to me before the episode that you don't ask standard interview questions. I'm really, I actually didn't ask you before because I thought I'd save it for now. Um, what did you mean by that? And then how do you discover, unpack question to determine whether people have those four traits?

A So I think people hide behind standard interview questions if they don't really know what they're looking for. And maybe the more junior you are, the more you kind of have to rely on those, you know, but I always think about, you know, the reputations of some of the trillion dollar internet companies and the tricky questions that they're asking people. Even when they do tests, by the way, for engineers, you know, I've seen really smart people not make it through those tests too. Could have been great engineers if they'd been mentored the right way and people saw the raw materials there. So I think people miss everything between the lines when they're asking standard interview questions, you know, tell me about a challenging time that you overcame something. Tell me, you know, it's just, how about you just really get to know somebody and do that through a conversation. And I promise you that if you do that, what they really know about the things you need to know come out, whether they have EQ, And, and the characteristics I described about that, they come out. But the other part of that is I don't do it in one sitting. So I'll trick people out sometimes by saying it was so great to spend that hour with you. I'll circle back and now we'll go get lunch. And then I'll bring them back a third time. And then I'll have them interview with my core team who already represent a lot of th…

AI assessment note: “how about you just really get to know somebody and do that through a conversation”

Q the balance between the short term and the long term? You know, if the short term is like, bluntly, as soon as possible, increase, increase, increase, increase queries, um, that's the short term, which will allow you in the long term to have product expansion, market expansion, more resources for expansionary products, teams. How do you think about that balance between the short and the long term in your thinking?

A Well, I'll just say it's different every time. So it, at ask, you know, you're, you, um, I think you get this a lot, but you're probably too young to remember the original Ask Jeeves product. It was a question and answer product that was essentially manual. And it showed up at the top of the page, 90% of the time in how we looked at the data. It was only clicked on 25% of the time. And so it also became the butt of a joke from, as a brand that it didn't work. In an entirely different situation. At CBS Interactive, we ran a portfolio of brands, and we did it by turning around CNET, which was a public company acquired by CBS, and really goosing revenue on CNET to pay for the subscription opportunity that we saw in streaming. And again, this is 20 11, 1213, leading in the 14, and we launched five years before Disney+, an obvious investment, and so we had to self-fund for the long term. So again, you know, every company is going to be different in how you think about it, but that's the fun of the job. That's why I love doing it.

AI assessment note: “goosing revenue on CNET to pay for the subscription opportunity that we saw in streaming”

Q Can I ask you, and this is very un-British of me, um, Yahoo is a well-known brand for short, household name, but known, as you said with Ask Jeeves, is kind of an old school name, and it's not Stripe, where everyone wants to go and work, and it's not sexy. My question is, is it just awareness that's important, or does, like, attractiveness matter too?

A Okay, well, this, this is a, uh, A great question. I think one where the answers will probably surprise some people. So look, Ask Jeeves as a brand was never going to be fixed, to be blunt. It was too far down, even when we were killing it in growth and growth. I think we're the only search engine to gain market share. We're the only one of the 15 public company search engines that weren't the major portals to survive. But we were never going to turn that brand around and become, you know, everybody's favorite search engine in the heart of Google. You know, Yahoo is a very different situation. It legitimately has nine hundred million users a month. And those users are coming, you know, in email, we're number two to Gmail. In Yahoo Finance, we're number one by a mile. Yahoo Sports is number two to ESPN. You know, in search, yes, we're down, but it's very valuable. And, you know, I've been there before. I think there's some things we can do with that. In news, we're number one. And, and that's after what I think we would all agree is not really the best last 10 years. Right. And, and, you know, not for reasons that were always their fault, you know, being a standalone public company for 20 plus years, um, you know, not really fighting with the best weaponry at that time and into the heart of Google and then Facebook and others. I mean, that was tough. Um, you know, and, and then …

AI assessment note: “Yahoo is a very different situation. It legitimately has nine hundred million users a month.”

Q What's the hardest element of your role with Yahoo today?

A Or just changing the mindset of people takes a lot of time that some of my team will laugh if they hear me say this, but I've, I've said a few times, I wish you could have been with me at prior companies to understand what this looks like and how it goes well and, and how you're going to feel and, and, and why we won and, and how great it was to be part of that team. You know, every time you do this, You're starting over. It's not as easy as 11 and Stranger Things being able to go back in the past and, and, you know, see, see back, you know, put your finger on someone's forehead and see what it was like. You know, you, they kind of have to live that experience and it's, it's hard to be patient all the time to, to bring a new team along to that. You just have to have faith. You'll get there.

AI assessment note: “changing the mindset of people takes a lot of time”

Q demo of the videos that you wanted to bring to Tinder, and you showed it to the board, and then you made it happen within three months. My immediate question was, as a leader, how do you think about bringing real product velocity and real execution speed, and respectfully accompanying Tinder's size, and now Yahoo's size, where generally things become a lot slower? How do you retain speed with scale?

A Yeah. I don't, I don't believe they have to be slower in a big company. Um, Tinder, like, like ask was a one product company, right? Tinder was a one product company. And so really I was the chief product officer and it was really easy to, to push. And that example though, And I think this is something that I've gotten to be pretty good at is I unblock things that had been in the queue for a long time. We had some really talented product people on the Tinder team who had developed the majority of that video demo that we kind of called our dream board video with the future of Tinder to look like. I didn't make it. I didn't direct them to. I heard about it and I said, hell yeah, let's go for that. Let's see what that looks like. I saw it. I helped them tweak it with my opinion, which is usually what I do. You know, it's not just me. I, I feedback and, and have good product, you know, sensibility too. And I let them go. And, and that, that video was really compelling. You know, Tinder hadn't evolved in quite a long time on the consumer front. They'd done a lot on the business model front. Uh, but they had not, you know, you being a big subscriber, but on the, on the consumer feature side, not a ton. And that video just showed all these possibilities, not all of which are going to make it to market, but everybody who saw that video was like, when can we have that internally for the…

AI assessment note: “once you have that, it's really easy to get the company unblocked”

Q of core traits. The thing that I find challenging is bluntly unpacking them and discovering them. Um, you said to me before the episode that you don't ask standard interview questions. I'm really, I actually didn't ask you before because I thought I'd save it for now. Um, what did you mean by that? And then how do you discover, unpack question to determine whether people have those four traits?

A So I think people hide behind standard interview questions if they don't really know what they're looking for. And maybe the more junior you are, the more you kind of have to rely on those, you know, but I always think about, you know, the reputations of some of the trillion dollar internet companies and the tricky questions that they're asking people. Even when they do tests, by the way, for engineers, you know, I've seen really smart people not make it through those tests too. Could have been great engineers if they'd been mentored the right way and people saw the raw materials there. So I think people miss everything between the lines when they're asking standard interview questions, you know, tell me about a challenging time that you overcame something. Tell me, you know, it's just, how about you just really get to know somebody and do that through a conversation. And I promise you that if you do that, what they really know about the things you need to know come out, whether they have EQ, And, and the characteristics I described about that, they come out. But the other part of that is I don't do it in one sitting. So I'll trick people out sometimes by saying it was so great to spend that hour with you. I'll circle back and now we'll go get lunch. And then I'll bring them back a third time. And then I'll have them interview with my core team who already represent a lot of th…

AI assessment note: “how about you just really get to know somebody and do that through a conversation”

Q I'm worried about, and I always advise founders against, is multiple cuts. You know, cut deep and do it once, but don't do multiple rounds of layoffs. That's really hard. How do you know how much to cut? Is it 20%? Is it 25%? Like, how would you advise a portfolio company if it was me saying, you've got 12 months, Do I literally cut 50%? How do I know?

A You know, I mean this very specifically, not to change the, the, the way to think about this. You cannot possibly know the answer to that unless you're in that specific company. And we can talk more about this when you think about how to fix a company or how to take one over. And, and mistakes people make when they do that, you know, coming in thinking they know everything from the outside. I truly believe a rule of thumb on this situation does not exist. And I also think that if you've built off, you know, uh, trust and credibility in an authentic way with your team, then, you know, the one cut versus different cuts. I mean, that, that isn't true either, right? Because you're getting different information at different times. I think you have to make the best decision you can at that time. Now, The thing you need to be careful of is not to underestimate because you've only lived through 13 years of growth and haven't been through all these crashes, uh, you know, underestimating how long this could last or estimating how harsh it could be. And, you know, I heard Brian Chesky speak recently on, on the cuts he made at Airbnb, uh, and, you know, during, you know, the initial, uh, COVID crash in 2020, And two things happened, right? One is they, they, they did what they needed to do balance sheet wise. The second was they actually discovered they were a better company when they were…

AI assessment note: “I truly believe a rule of thumb on this situation does not exist.”

Q Can I ask you, Jim, when I listen to you, you're so assured in your leadership. Everyone says what a brilliant leader you are. You know yourself better than anyone. Where do you think your biggest holes in your leadership are?

A Oh, you know, it, it, it's probably changed over time is what I would say. So, um, you know, In the old days, it was, is, you know, when I started, I came out of grad school. I, I wasn't an engineer. I wasn't technical. And I, you know, all on the way, I've had to learn the job from that side of things, right? Not from the engineering side of things. I'm also, by the way, not a CFO, right? I could, I could pretty much drop down to do most people's jobs in the company, but, you know, in some ways, even the CTO at this point, although engineers were laughing at me, I'm not, I'm not saying I'm not technical, but. Any means. I just mean operationally with the lever pulling is for that job. CFO is not one where you would put me. Um, again, I've had CFOs now for 20 plus years and, uh, you know, I'm really lucky with Monica. My current CFO is amazing. And you know, my, my CFOs at all my last companies have just really been great. I need that person to be a really strong partner to me. Uh, so You know, yeah, I know what you're good at and what you're not, where you add value and where the team can balance you out.

AI assessment note: “I'm also, by the way, not a CFO... CFO is not one where you would put me.”

Q And so how long do you give people who aren't performing? It's a big question. I always have.

A It depends if the more junior it is, I think the more quickly that typically moves through, I think the more senior the role is, you know, the kind of, there's more reasoning and more, you know, work that went into putting them there and you're probably giving them much more of a chance. So I've never, Put someone in a very senior role and then realize it was wrong and off them within, you know, the first few months. I mean, you really, you really do give a due process to see and, and, and a couple, you know, turns to, to see how they react. Um, again, I wouldn't say there's a hard, fast rule for that, but, you know, another way of looking at it is it's, it's not that long, right? I mean, if it's not working, it's not working, uh, which means they're probably, they're probably miserable too.

AI assessment note: “I wouldn't say there's a hard, fast rule for that, but... it's not that long”

Q When you're getting to know them in that way, can I ask, are there commonalities in the areas where you focus? Is it childhood? Is it insecurities? Is it young entrepreneurship activities? Is it parental relationships? Are there areas where you find revealing in terms of getting to know people? If it's not the standard, respectfully, what is it?

A I don't, I honestly, Harry, don't think there's a standard for that. I think it's a conversation. I am trying to eventually get to what they know, how they operate, right? There are a million companies at the bottom of the ocean that had perfect sounding mission statement or had, you know, I truly believe your company values are the people you hire. Like that is 90% of it. It's also, you know, what you accept and condone, what you criticize and don't allow it's, it is. And so I think those values come out in, in, in these conversations as you're getting to know people. And again, let's go back to why I'm doing this. It really is an interview. Um, but I'd say it's different for every person, and yeah, getting to know their origin story, and sometimes I'll just ask that, um, is part of it.

AI assessment note: “I honestly, Harry, don't think there's a standard for that. I think it's a conversation.”

Q Can we unpack growth? And I mean that respectfully, but it's like growth of growth of user base, like growth of retentive users, growth of monetization on a monthly basis. Like how do you determine growth? Cause more users doesn't necessarily mean more growth. Do you know what I mean?

A A hundred percent. We, yeah, I mean, Again, and let's just say this is consumer internet from my point of view. So to your point, you, you can't have one without the other. They all have to come along. And so in a search engine, that's very easy. You have to have query growth, right? And your monetization is pretty linear off of that in search, because you know what the The revenue per thousand searches is you really just have to, to, uh, to increase the number of searches. As long as you have that monetization imbalance with a, uh, you know, a, an ad supported, you know, model and display, of course you need the user experience. You need growth at X percent, uh, to be able to, to monetize if you over monetize. And I do think there's an inflection point, which is why I always say you want to optimize, not maximize. You know, either one of these things, right? Revenue or the user experience. They need to be at this point of optimization where they're both growing at a healthy rate. And look, you can say this is rocket science and try to make it more complicated than it is. I don't think so. You know, it's, it's, it's pretty easy to look at the data and understand where you're, um, under optimized and where the focus needs to be. And over the long term, they all need to come along. So that's why I say short, medium, and long term. Now that can apply to your quarterly product road…

AI assessment note: “you can't have one without the other. They all have to come along.”

Q And so how long do you give people who aren't performing? It's a big question. I always have.

A It depends if the more junior it is, I think the more quickly that typically moves through, I think the more senior the role is, you know, the kind of, there's more reasoning and more, you know, work that went into putting them there and you're probably giving them much more of a chance. So I've never, Put someone in a very senior role and then realize it was wrong and off them within, you know, the first few months. I mean, you really, you really do give a due process to see and, and, and a couple, you know, turns to, to see how they react. Um, again, I wouldn't say there's a hard, fast rule for that, but, you know, another way of looking at it is it's, it's not that long, right? I mean, if it's not working, it's not working, uh, which means they're probably, they're probably miserable too.

AI assessment note: “It depends if the more junior it is, I think the more quickly that typically”

Q How many direct reports do you have, Jim?

A It'll come and go. So the proper amount for, for my job is probably somewhere between 10 to 12. And over time, these general managers, you'll wind up with some, what I, you know, refer to as, you know, nicknamed super GMs, where you'll have GMs who have multiple GMs reporting to them in groups or segments that make sense. Cause this is a portfolio play. It's a conglomerate play. And at CBS Interactive, when I inherited multiple former public companies and the CBS assets, my first thing, I was, I was like a pig in slop as a product guy, right? I was like, oh, I can't wait to dig in on fantasy football and on CNET and on CBS news and last FM and all these things, but the reality, and so I had 25 direct reports and I got just smacked in the face the first year trying to keep it all together. So what I really, what we, what we created was a model that we called federal and state. Where you create, you know, essentially governors of each of these businesses, sometimes in groups, and you, you give them the, the operational mandate to run their own business reporting into me. And my job is to, you know, hire and fire and manage them and work with them on their plans. And then at central or federal, you know, our job is to provide leverage Uh, you know, as cheaply as possible, right back into those businesses and let them run.

AI assessment note: “proper amount for, for my job is probably somewhere between 10 to 12”

Q You said point number three, optimism and trust. If you are optimistic in the times of Winston Churchill style, where everything is going to shit, and you are still saying we'll be fine, your team will lose trust. How do you think about the balance between being eternally optimistic and retaining trust when everything is not okay?

A Yeah. I mean, two things. One is you can't be an ideologue, right? And same thing. You have to fight, fight the battle that exists on the ground. And in their case, they were fighting back. I don't want to get too much in the history here, but they were fighting back and having some success with that. It just was tough. And that's what going through a crash period can be like, you know, and the days are long, but the years are short and, and. Uh, but those days, you know, those long days can really be rough. Uh, and so you don't want to be an ideologue and, and part of it is just being honest and unscripted and, uh, and direct and, and having a team of people around you if you've hired that the right way where their teams trust them. And, and I, so I, you know, I think of these companies as ecosystems, so I don't, I wouldn't again, put it on one person, but hopefully you, hopefully you've created that Uh, that, that ecosystem. The other part of not being an ideologue is adjusting your business model, right? Go back to Airbnb. They cut down to the core old Airbnb. Just at the right time when it turned out, that's exactly what people wanted in the summer of 2020 was they wanted to go rent houses, right? They couldn't travel. They couldn't fly. Um, How do you need to adjust your business model? How do you need to adjust your valuation expectations? Right? I, I, we just came throug…

AI assessment note: “part of it is just being honest and unscripted and, uh, and direct”

Q Can I ask, what's been your biggest hiring fuck-ups? You learn from mistakes. You've been doing this for 25 years. Respectfully, there must be some.

A Yeah. Well, in the old days, I'd say I was, you know, what happened after the web one point oh crash, or even during that time, it was, You know, later on, 19 year olds were CEOs of companies and that was cool. But in the nineties, we were all told you can't do it. You better hire some grownups. And they usually came from consulting or P or P and G. Right. And that led to success, uh, over excellence process over, you know, how you, and I fell into that trap. You know, I remember eBay had a lot of people during the time, but they, they lacked EQ. They lacked, uh, knowing what good looks like. They lacked that right brain. Uh, like a band, not like a symphony, right? You're not writing sheet music and chucking it over the wall for someone to play. The best product development happens when you're all working together. And that goes back for me to how I built my first product in the nineties. Um, and so I think, you know, not, not trusting that, not really knowing what I was looking for in the early days. And then the second would be up here and, and, and maybe this won't work. I tell you when I have that intuition, you know, I've, I've, I've made the wrong high.

AI assessment note: “not really knowing what I was looking for in the early days”