The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

Kevin Ryan no published score: only 6 usable exchanges on raw tape, and a fair score needs 8+ · coarse estimate ≈4.5/5 from 6 raw tape exchanges record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Wasn't it basically just like Gilbert comics or was it?

A Exactly. Yeah. Dilbert comics. And, and we had other comics. We own peanuts and a lot of other ones, but on a relative basis, it became very successful as a website. We sold, uh, advertising, uh, e-commerce. Uh, so things that were not that easy to do because we didn't have the vendors at the time. So I went to the parent company and said, look, we should build up an internet division. And they said, no. I thought, you know, I actually believe that the internet's going to be a huge, which is obvious now, but you know, a huge part of the next 25 years. I want to go do this full time. So I was going to go start a company. I ran across DoubleClick that was already in the ad tech space. They committed me to join them instead of starting my own company. I became the CFO, the president, and then the CEO.

AI assessment note: “Exactly. Yeah. Dilbert comics. And, and we had other comics.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q choices people make when, um, when it comes to a funeral. And this is like, that's a one chart business. You can look at nothing else and say, all right, I know there's, I know there's opportunity when I look at a chart like this. Um, is, is that, does that jive with your way of thinking or do you have anything you could add to our understanding of that?

A No, no, absolutely. I mean, I'll give you another one. The cost of labor is going to just keep going up. And so, you know, waiters were paid 15 dollars an hour. Now it's 20 to 25 dollars an hour in New York. Unless we change immigration or something fundamentally changes, that could be 30 dollars an hour. So you know what? Over time, that changes the calculus of automation. Whether it's making french fries, whether it's through this, we're all going to have to find ways to use less labor. And so when cost of tech goes down and the cost of labor goes up, what does that tell you? More automation is going to happen. Uh, so I'll bet on that trend all day long. You know, we're an investor in a company that gives robotic massages. There's 17,000 open positions for massage therapists in this country. And so, you know, there's hotels that just can't offer massages because they don't have the people. So, you know, we hope they're gonna offer a massage. So that is just one example, but I have 10 others.

AI assessment note: “No, no, absolutely. I mean, I'll give you another one.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I gotta know what's the, uh, what's the secret? What, you know, what, what was it that you guys were doing differently? And I'm sure you've talked to many other people. You've seen many entrepreneurs start these labs and you've probably seen the same results that I have, which is that very, very few. Come up with anything that works. What do you think you guys did differently than others?

A So it's not that, you know, detail wise we did anything differently. At the end of the day, this is a simple business, but hard to do. In other words, you need a good idea and you need a good team. Uh, so that's just, there's nothing else. Uh, so, you know, we've had some good ideas. Uh, we do a lot of research, you know, any one time we're doing deep dives. So someone will spend two and a half months interviewing, 50 people doing the same thing that I would do if I were an entrepreneur about to start a company. So we have a lot of knowledge. There's a 50 page deck. We've really gone into it and then we're committed and then we go hire a great team and we help that team. But again, it's a little bit like watching, you know, I don't know, a good basketball player, a good soccer player. We know what they do. We can see what they do. Can I do what they're doing? Not very easily. So I think we've executed well there. And, you know, we have a bunch of people, including myself, have a lot of experience doing this. It's just a series of judgment calls. You know, I think, ah, I'm able, because of the track record, able to convince some good people to be CEOs. Um, that's important too. And we, you know, we spend a lot of time helping them. So I chair 12 companies. So about half my time is spent focusing on those 12, which are 12 of our most valuable companies, uh, to really guide them a…

AI assessment note: “it's not that, you know, detail wise we did anything differently.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q And for someone who's thinking about 10 years, I'm a little surprised. I don't see AI all over this doc. Uh, you know, you're not saying AI, AI, AI. It sounds like it might be embedded in some of these things that you're doing. Uh, like might be a tool you use, but are you bearish on it for some reason? Or what's your thinking around AI?

A No, I'd say two things. One, it's coming down now, but if it were six months ago, you know, the pricing on AI was insane. You know, three people walk in and say we're worth a hundred million dollars because we're going to put together an AI company. Just didn't make sense. So we didn't make any direct investments there. Um, each, we're really encouraging each one of our companies to use AI. And I think the, you know, the real use of AI in the short term is going to be much more mundane. It's optimizing customer support, you know, making your coding more efficient, things like that. Uh, we're a long ways before, you know, true AI companies are coming, but it's, but it's, it's on its way. We did something unusual this summer. The, our entire technology team shut down for a week, went home, and their only assignment was to learn about AI the entire week. Read about it, think about it, talk to people.

AI assessment note: “So we didn't make any direct investments there. Um, each, we're really encouraging”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What are you looking to change or improve? So if we talk to you 10 years from now, what do you hope, what do you hope is different about you or your lifestyle or your businesses that versus today?

A So I'm doing most of the things I want to do now. So one, you know, it's going very well. Results have been great. I spend three to four months a year in Europe working from there. I grew up in Europe. My wife is French. Uh, I have one child there. Uh, and I, I enjoy that. So I'm planning on continuing that. I want to keep doing various, you know, athletic and interesting trips around that, that, you know, that, that, that I enjoy. So from a high level, I'm not planning on changing it dramatically. The, I, I actually love what I'm doing. I think we're having fun and we're going to continue to do this. I don't want to make it much bigger. You know, I don't want to have that many more people. That'll just make it more sort of system oriented where I'm not close to the companies. Because what I enjoy is when I'm close to the companies and the problems. And that's where I think I, I add value. I'm just trading off. I'm very old at this point in this industry. And so I'm, you know, hopefully reaping the benefits of the judgment that you get after dealing with these things and making lots of mistakes along the way, but a bunch of things going well.

AI assessment note: “from a high level, I'm not planning on changing it dramatically.”

Partly raw tape D 3 · C 3 · P 4 · Cm 4 3.40

Q fearlessness is something you have? And do you, do you notice that like, do you feel like sometimes I look at other entrepreneurs and I think, man, I can't believe that more of them are not doing X. Do you feel like that about the way you approach entrepreneurship? Like, I don't know. I feel like more people should be trying the thinking this way, but they don't seem to.

A I mean, look, what we do is just a, Slight variation of an entrepreneur. They just happen to have entrepreneurs working for me and we have a structure and, and don't forget, we also have, you know, I have 70 engineers who work for me. I have my own in-house outsourced engineering company, which helps us build product now very quickly, which we've had the last three years. Uh, I own a big chunk of a search firm, a 10 person executive search firm that we set up so that we can get some of the best talent working for us finding CEOs. So we built infrastructure around it, but still most of it goes back to a good idea and a good tea. And when we get that right, yes. And by the way, last one on psychedelics, I had done plenty of work. I mean, I'm not a scientist, but I've gone through the academic papers. I know the state of research in psychedelics. I know it's working. And look, what I am thinking about all the time and everyone here does is where is the world going to be in 10 years? That's the North Star for what we're doing. If something's gonna happen next year, it's too late. I need to bet on a ten-year trend. So, you know, we do a bunch of things in robotics and automation because I feel good about that trend. Psychedelics is a ten-year trend. MongoDB was a ten-year trend. Um, these are the things we're betting on.

AI assessment note: “what I am thinking about all the time and everyone here does is where is the world”

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