The Exchanges

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: “we were all told you can't do it. You better hire some grownups.”

Q What are the most common reasons for blockage?

A I do think. It goes back to these qualities of a great manager or, or employee. And oftentimes there are people in positions of product power, product roadmap power, who either are not great at being the hub or the quarterback for the groups around them. So you're not able to get buy-in and give all the groups due process. I always say that once you get through that process, you know, again, cause I started as a product manager, essentially, um, You know, everybody should feel they've fed into that. So even when you, when you aren't doing what they wanted to do, they understand why you made the decision. And hopefully oftentimes they feel it was their idea. Even maybe it was their idea. Um, so that, that, that's a big part of it. Uh, and a lot of times people wind up with battlefield promotions or different reasons why they got to a position of, you know, power and product where they're not Great decision makers, or maybe the people above them, you know, I always say like, I wouldn't be great at being the CEO of different kinds of companies, but I've done consumer internet for 25 years. I know how to run this kind of company. Right. So it's easy for me to say, let's go for it and get things out of the way. It also helps. I came out of product management, which I think make. Not all the time, but usually, you know, it's, it's, it's best for a CEO of an internet company to have b…

AI assessment note: “oftentimes there are people in positions of product power... who either are not great”

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, I think, you know, moments of hardship can often shape you as a leader. When you think about really painful lessons learned, is there one really painful lesson you learned that you were actually, on reflection, pleased to have gone through, and what did you take from it?

A I am both fortunate and unfortunate enough to have been through a lot of really trying times and come out the other side in a really good spot almost every time, not the first startup, and that was super, super painful for everybody involved and We all felt, you know, I think we all felt really hurt by, by that not, not working, you know, the, the nineties startup. Um, but every other one, you know, I just think the trying times that we went through, you know, when I got to ask, there were, it was post nine, 11, there were rolling blackouts in California. People were taking sodas from the machine home at night. They had gone from, you know, a, a, a ten billion dollar valuation to a hundred million dollar valuation. It was, it was rough. So to come through the other side, I mean, that, that was, was just such a validating, you know, experience that gives you confidence. But then when I did the next startup, you know, and again, I had Bill Gurley behind me. I mean, very Jeff Yang, like the best investors, you know, I accepted money and the, and the, the crash of 2008 happened two weeks later. I offered to give the money back. Uh, and they said, no, just, just go ahead because some of the best companies can be created in times like this. And you and I know, Now that how, how true that was for, for the 2008 crash. Um, so to have landed that plane, yeah.

AI assessment note: “some of the best companies can be created in times like this.”

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, I think, you know, moments of hardship can often shape you as a leader. When you think about really painful lessons learned, is there one really painful lesson you learned that you were actually, on reflection, pleased to have gone through, and what did you take from it?

A I am both fortunate and unfortunate enough to have been through a lot of really trying times and come out the other side in a really good spot almost every time, not the first startup, and that was super, super painful for everybody involved and We all felt, you know, I think we all felt really hurt by, by that not, not working, you know, the, the nineties startup. Um, but every other one, you know, I just think the trying times that we went through, you know, when I got to ask, there were, it was post nine, 11, there were rolling blackouts in California. People were taking sodas from the machine home at night. They had gone from, you know, a, a, a ten billion dollar valuation to a hundred million dollar valuation. It was, it was rough. So to come through the other side, I mean, that, that was, was just such a validating, you know, experience that gives you confidence. But then when I did the next startup, you know, and again, I had Bill Gurley behind me. I mean, very Jeff Yang, like the best investors, you know, I accepted money and the, and the, the crash of 2008 happened two weeks later. I offered to give the money back. Uh, and they said, no, just, just go ahead because some of the best companies can be created in times like this. And you and I know, Now that how, how true that was for, for the 2008 crash. Um, so to have landed that plane, yeah.

AI assessment note: “to come through the other side, I mean, that, that was, was just such a validating”

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 wasn't technical. And I, you know, all on the way, I've had to learn”

Q What are the most common reasons for blockage?

A I do think. It goes back to these qualities of a great manager or, or employee. And oftentimes there are people in positions of product power, product roadmap power, who either are not great at being the hub or the quarterback for the groups around them. So you're not able to get buy-in and give all the groups due process. I always say that once you get through that process, you know, again, cause I started as a product manager, essentially, um, You know, everybody should feel they've fed into that. So even when you, when you aren't doing what they wanted to do, they understand why you made the decision. And hopefully oftentimes they feel it was their idea. Even maybe it was their idea. Um, so that, that, that's a big part of it. Uh, and a lot of times people wind up with battlefield promotions or different reasons why they got to a position of, you know, power and product where they're not Great decision makers, or maybe the people above them, you know, I always say like, I wouldn't be great at being the CEO of different kinds of companies, but I've done consumer internet for 25 years. I know how to run this kind of company. Right. So it's easy for me to say, let's go for it and get things out of the way. It also helps. I came out of product management, which I think make. Not all the time, but usually, you know, it's, it's, it's best for a CEO of an internet company to have b…

AI assessment note: “people in positions of product power, who either are not great at being the hub”

Q Do you believe the best CEO is the best resource allocators?

A Yeah, it's a fundamental around you. Again, I would, I will always point you back to the fact that I, I do think I am, you know, really good at certain things. Product is one of them. Um, you know, culture building has always been really important to me, but I, I, It is, it is a huge misnomer to say that anybody can, can be a great CEO by being a dictator. It just doesn't work that way. So dictator is resource allocator, roadmap, anything. You are a ringleader. Same team. They would say I didn't operate that like a dictator either. You know, I, I treated it like I was the ringleader, but, but you gotta do it as a team.

AI assessment note: “Yeah, it's a fundamental around you. Again, I would, I will always point you back”

Q Do you believe the best CEO is the best resource allocators?

A Yeah, it's a fundamental around you. Again, I would, I will always point you back to the fact that I, I do think I am, you know, really good at certain things. Product is one of them. Um, you know, culture building has always been really important to me, but I, I, It is, it is a huge misnomer to say that anybody can, can be a great CEO by being a dictator. It just doesn't work that way. So dictator is resource allocator, roadmap, anything. You are a ringleader. Same team. They would say I didn't operate that like a dictator either. You know, I, I treated it like I was the ringleader, but, but you gotta do it as a team.

AI assessment note: “dictator is resource allocator, roadmap, anything. You are a ringleader.”

Q What is the number one thing you need to fix in the org? And what's the number one thing you need to fix in the product?

A So, um, I don't think there's just one or two movers here. I think the, the thesis for both Apollo and for myself is that taking these assets, you'll take a lot of shots on goal, right? You have, you, you, you have a lot of assets that are generating a lot of cash and that allows you to invest all around the business. Some will be existing things. Some will be new things. We've, we've been looking at, at acquisitions already the, you know, the last nine months I've been here and playing offense that way. So, You know, I'm not sure if, if, if you've heard this yet, but, but Yahoo is already one of the fastest returning deals in Apollo history. We're already in the spot. We're already in a spot where we can focus on the upside and in a good way, we're greedy for that upside. So this is an investment opportunity, right? If Apollo and what you hear about private equity, if, if what they wanted to do was smelt this thing down for parts, they would have done it already. And they wouldn't have brought in a guy like me. He would have brought in a financial engineer, right? Not a consumer growth person. The objective here is growth. That can happen in many different ways. We're going to take a lot of shots on goal. We don't need them all to work. Um, but if we get great people, I think the majority of them can work. And, and so I do think that this is a potentially longer term play, esp…

AI assessment note: “I don't think there's just one or two movers here.”