By playing, you agree to uListen's Terms and Privacy Policy and YouTube's Terms of Service.
My First MillionHow This Billionaire Founder Finds +$20B Business Ideas | Kevin Ryan Interview (#495)
Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.
EVERY SPOKEN WORD
65 min read · 12,950 words- 0:00 – 3:15
Intro
- SPSam Parr
You, you like violate this rule that I have for myself. And, uh, you, you do it so wonderfully, which is focus.
- KRKevin Ryan
Mm-hmm.
- SPSam Parr
Or at least it appears as, as you do. You like launch like, I don't know, how many companies a year do you launch?
- KRKevin Ryan
Eight.
- SPSam Parr
Eight? God damn. [upbeat music] All right. We're live. Kevin, do you... This is Kevin Ryan.
- KRKevin Ryan
[laughs]
- SPSam Parr
Do you remember me?
- KRKevin Ryan
I don't remember where we met. I know we've met, but I don't remember where.
- SPSam Parr
That's good. Okay. You don't have to remember. So basically, I'm gonna tell you why. This is funny. So basically, I've studied you for maybe 10 years. So you started, uh, you were the president of, uh, and CEO of DoubleClick, which had like a, a billion dollar plus exit. And then you have started like four or five companies that are... One's worth, I think, 28 billion today. One's worth, uh, uh, you have a couple billion dollar exits. But you started Business Insider, and I cold emailed you maybe 50 times. And one of those times, because I admired you so much, and we'll talk about your career, but I, I wanted to be like you. In one of those emails, you finally replied, and you just said like, "Thanks for the updates," whatever. And then I lied and I said, "I'm gonna be in New York tomorrow. Can I get 20 minutes of your time?" And you let me do that. And I came to your office for literally 20 or 30 minutes. We had such an impactful conversation. And then you did another follow-up call with me, and I have the notes from those calls, and this was in 2017. And you made a bunch of predictions about my life, as well as the media business and a few other things, that were 100% true. And I refer back to that note sheet on a consistent basis to help make some decisions.
- KRKevin Ryan
Oh, interesting. Well, I'm gl- I've, sometimes I get lucky and I get it right.
- SPSam Parr
And you wanna know what? Your c- your PR people cold emailed us-
- KRKevin Ryan
[laughs]
- SPSam Parr
... to get you on the pod. So the tables have turned, my friend. Welcome to my world.
- KRKevin Ryan
Exactly. [laughs]
- SPSam Parr
But I just wanna say, like I've admired you for a long time. You're, you're a really big deal to me, and so I'm so happy that we're able to like finally do this. This is awesome.
- SPShaan Puri
And Kevin, uh, you don't know me, but I, I did not stalk you. I did not cold email you.
- SPSam Parr
[laughs]
- SPShaan Puri
In fact, I was a little bit, uh, just jealous of you, 'cause I was at the time working in a, um, when Sam was telling me about you, I was working at a, uh, startup incubator studio. And so we were launching four or five companies a year. And, um, after three or four years, I was like, "I don't know if this model even works. I just feel like it's like, uh, this..." Uh, uh, 'cause there's something inorganic about the studio model versus like just a normal startup that, that comes from an entrepreneur solving their own itch. And he's like, "Well, I don't know. This guy Kevin Ryan seems to do it. He's cranked out four or five billion dollar companies out of this." And I was like, "Huh, I guess I should shut up and, uh, just, uh, you know, I guess it's not the model that's the problem, it's me." Uh, [laughs] so you know, I, I, I think not only is it cool that you built, built big media companies, it's cool that you made the stu- the studio model work when very few people have been able to do that.
- KRKevin Ryan
Yeah. No, no, I still enjoy it. Uh, it by and large is still working. You know, things go wrong. It's not, I wouldn't say it's easy, but we have a lot of companies that are doing really well in, in different sectors, and so that's what's so fun. And look, there, there are more things to be done. There, there are many problems in society that have not been solved.
- SPSam Parr
And basically,
- 3:15 – 5:20
Selling DoubleClick to Google for ~$3B
- SPSam Parr
the high level story of you is you, uh, you had like a normal corporate career, but then you kinda like worked your way into, uh, DoubleClick-
- KRKevin Ryan
Yeah
- SPSam Parr
... which eventually I think became Ad- AdWords at Google.
- KRKevin Ryan
Exactly.
- SPSam Parr
Is that right?
- KRKevin Ryan
Yeah. So Google bought it for about $3 billion in 2007. Uh, the company started in 1996. I was there for nine years. It was public for seven years. First four years went from 10 people when I joined to 2,000, it was so crazy, in 25 countries. So that's what I spent my early 30s doing. Um, then we spent three years bringing it back to 1,000 people as the internet collapsed, and 70% of our clients went bankrupt. So don't do that. Uh, then we, we had huge market share, controlled basically ad technology, and so then, uh, Google bought it. And then I started, uh, Business Insider, you know, Mongo and Gilt.
- SPShaan Puri
I wanna point one thing out in, in this journey, by the way. Your career starts at Prudential. Uh, so sh- shout out to all the listeners out there who are in boring companies right now.
- KRKevin Ryan
Yeah.
- SPShaan Puri
Boring, huge companies, consultants and bankers out there, there is hope for you yet. Um, so you did like-
- SPSam Parr
[laughs]
- SPShaan Puri
... Prudential, Euro Disney, blah, blah, blah, and then you joined DoubleClick as employee 20.
- KRKevin Ryan
Yeah.
- SPShaan Puri
But you, you, they brought you in, I guess, as like-
- KRKevin Ryan
Yeah
- SPShaan Puri
... a senior person at the time?
- KRKevin Ryan
Yeah, yeah. Uh, what happened is I had launched an internet website for EW Scripps, which is a media company, and I was the COO and CFO of a division of that company.
- SPSam Parr
Wasn't it basically just like Gilbert Comics, or was it-
- KRKevin Ryan
Exactly.
- SPSam Parr
Yeah.
- KRKevin Ryan
Yeah. Gilbert Comics, and, and we had other comics. We owned 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. Which I thought, you know, I actually believe that the internet's gonna be a huge, which is obvious now, but you know, a huge part of the next 25 years. I wanna go do this full time. So I was gonna go start a company. I ran across DoubleClick that was already in the ad tech space. They convinced me to join them instead of starting my own company. I became the, the C- the CFO, the president-
- SPSam Parr
That's insane
- KRKevin Ryan
... and then the CEO.
- SPSam Parr
And then when we met,
- 5:20 – 11:00
Starting Business Insider, MongoDB and Gilt
- SPSam Parr
you basically, you, you kind of outlined after selling DoubleClick, you said basically, "My partner Dwight and I, we came up with this thing where, we called it AlleyCorp. And we're like y- we get like two or three, maybe even one good idea a year. And then we find good people, and we give them $300,000. And we say, 'You have six months. Let's see if we can make this work together.'" And you did that with Insider, Business Insider, which I think had a $500 million exit. You did it with Zola, which is still running-
- KRKevin Ryan
Yeah
- SPSam Parr
... and it's kicking ass, I believe.
- KRKevin Ryan
Yeah.
- SPSam Parr
You did it with, with Gilt-
- KRKevin Ryan
Yeah
- SPSam Parr
... which I think got to like 500 million in sales.
- KRKevin Ryan
Yeah, yeah.
- SPSam Parr
But it, it didn't end up working out wonderfully-
- KRKevin Ryan
No, we, we-
- SPSam Parr
... I, I think you said
- KRKevin Ryan
... yeah, we, I mean, we sold for 250 million, which was less than we thought, but is still obviously a, a, you know, a real number.
- SPSam Parr
Good, yeah. Great And then you, you can go ahead and correct me, but you've done this with, like, four or five companies. I, I remember this meeting from 2018. I said 300,000. That was wrong, right?
- KRKevin Ryan
Yeah. So we started each company with a million dollars, so 500,000 from each one of us, and that was for Gilt, Business Insider, and Mongo. Uh, and then we d- I did ... A- after that, Dwight semi-retired, and so I did that with, uh, Nomad, I did that with Zola. Uh, and now, by now, I put about a million and a half dollars in each company when we start them.
- SPSam Parr
Which isn't a significant amount of money for how big ... I mean, I, uh, MongoDB right now is trading, I think at, I think its market cap is $26 billion today.
- KRKevin Ryan
Yep.
- SPSam Parr
I'm sure at its, at COVID peak it was, like, 40 or 50.
- KRKevin Ryan
Yep.
- SPSam Parr
That, that's not a lot of money for the outcomes.
- KRKevin Ryan
No, no. And, hey, look, we had to raise a lot of money. I mean, Mongo, between being a private and public company, raised and lost a billion dollars before they had a profitable quarter, and now already make $300 million a year in profits. So that's why it's so valuable is because it's a n- it's just an incredible company, growing quickly, enormous market share, and is gonna grow for the next 10 years. It'll be a $50 billion company.
- SPSam Parr
Well, you told me in our call, you said, one of my notes is basically, "If you're not hiring fast enough," and, and by the way, this is, like, turn- this is the VC route. But you said, "If you're not, if you're not hiring fast enough and losing money," AKA investing-
- KRKevin Ryan
Mm
- SPSam Parr
... "you either haven't figured it out or you don't believe that your idea is good enough. Um, and so you need to go- grow faster." [laughs]
- KRKevin Ryan
Well, and but you, you don't wanna grow fast just to grow fast. If you have a good idea, and if you're hiring a salesperson who costs 150,000 and they're selling $500,000 worth, you need to hire those people all day long, 'cause you have an opportunity. And if you have other products to create, you should hire these engineers to, to build it. So again, it's not spending money to spend money, but if you're building a big company, it's gonna take eventually 1,000 people or a few thousand people to do a billion dollars in revenue.
- SPSam Parr
Well, y- [laughs] and y- your analogy was, you go, "Look, if I bu- if my idea is good enough, I'm gonna build a machine that turns $1 into $2."
- KRKevin Ryan
Yep.
- SPSam Parr
"And if I have that machine, what are you gonna do? You're gonna go get as much money as you can and back that truck up into that machine and dump it in there."
- KRKevin Ryan
Exactly.
- SPSam Parr
[laughs]
- KRKevin Ryan
Now, there are times in various companies where it doesn't make sense to invest a lot more money because we're not getting the return. You know, you run out of market share, uh, it's not as big a market as you think, something's not working as well. And so then the right thing to do is to not invest, and I have companies right now that we've cut 30% of the people in the last year because given this market and what they were doing, we had too many people.
- 11:00 – 15:00
What led Kevin to start Business Insider
- KRKevin Ryan
You don't have time to wait.
- SPSam Parr
What insight ... Was Insider Business Insider? Was that ... So you sold DoubleClick. You, back then, when you and I met, you actually told me how much money you had made off the DoubleClick sale. I, I won't say it unless you wanna say it. But did you, um, which I thought it was amazing that you told me this. I was like, damn, this guy's helping me out so much [laughs] by telling me all this information. Did you, you and Dwight got together to start, I don't know if you call it an incubator or what- whatever you call AlleyCorp, but did you ... Was Insider the first idea that you had, and what led to that, what led to the insight to start that?
- KRKevin Ryan
Yeah, so the Insider idea was so simple that you can't even give us credit for it. So this is 2007. I love business publications and media publications. So I, I'm a sort of a compulsive reader of that, and I didn't have the publication I wanted. And it's so hard to f- to remember for j- people today that the Wall Street Journal and Business Week at the time did not, basically did not update their websites during the day.
- SPSam Parr
That's crazy.
- KRKevin Ryan
They thinking that's impossible. And the reason is that they were still on that schedule of the paper comes out the night, you know, the, the morning, articles have to be done late at night, and so at 10 in the a- 10:00 AM, no one's updating anything And so they just had not adapted. And don't forget, uh, your, we only got, uh, mobile phones in 2008. And so then all of a sudden, all day long you're in the taxi, of course you wanna get an update on what's happening. So we, the things we did are so obvious and done today, but they were, we were early, which is updating things continually, writing stories that were not complete in a way. We'd hear a rumor that X company was buying Y company. We'd say, "That's what we're hearing." And you know what happens when you write that? Someone from that company calls and says, "Yeah, actually it's true." Um, and so then you get more information, and so you maybe write four or five stories during the day as you get more and more information. And we also had a point of view. So you know, we'd write, uh, "So and so just overpaid for a company." It's more important that we have a smart point of view than that we're right in the long term. And so, and we did a great job of making sure we showed up in search results. So again, everyone does that today. At the time, no one cared about headlines because if you had Business Week magazine, does the headline result in more revenue for you? No. But when we, we would A/B test three headlines very quickly on a story and realize what was working. And so, you know, what I'm proudest of is that Business Insider is at 300 million uniques today, and never spent $1 in advertising.
- SPSam Parr
Yeah, you told me, well you said, you s- you, you said, "We were just, we were gonna just churn out these articles," which, um, is common now, but you go, you had this really [laughs] cool insight. You go, "It, it's kind of like Honda in 1985 versus General Motors. Americans laughed at the Honda, uh, car. They said, 'This is just too flimsy. This isn't good.' But they're gonna like capture some market share, and they're going to improve." And you said, "It's kind of like that with Business Insider." P- the, the, the quote, the critics or the, the real people in the industry, whatever you wanna call them, they laughed at you and they said, "This is just low quality. This is junk." And you're like, "But we're gonna get more traffic than you." And I think it took like five years or something, but we got more traffic than Wall Street Journal, and now they're looking at us like, "Holy crap, you surpassed us, and we could afford to have a more substantial journalism that maybe is taken more seriously," if, if that's even-
- KRKevin Ryan
Yeah
- SPSam Parr
... uh, something you cared about.
- KRKevin Ryan
No, no, by, I, I would guess by 2015 we had seven people covering military and defense. That's deep coverage. I mean, you, you, you have a lot, you're writing great stuff. In the beginning obviously we had, you know, five journalists covering the whole world. It's not gonna be amazing. But that, that is a good parallel, and we, uh, the product did get better over time. We started winning awards. Uh, but it always was intended to be a different positioning. It was punchier, it appealed to younger people. Uh, it was opinionated. You know, it's just a different product. Uh, but I think, I think the company,
- 15:00 – 16:45
Why Kevin hired Henry Blodget to run Business Insider
- KRKevin Ryan
you know, Henry Blodget, who's still the CEO, has done an extraordinary job in over 15 years, and a lot of these insights came from him. And he-
- SPSam Parr
You know, but-
- KRKevin Ryan
He was one of seven people I interviewed for that job, and he killed it.
- SPShaan Puri
Uh, what'd you see in him that, uh, made you pick him?
- KRKevin Ryan
Yeah, no, if you, if you remember it was a bold choice because Henry had, had some issues on Wall Street. Um, so you, some people felt like he was tainted. I knew that he-
- SPSam Parr
And, and the, the issues, by the way, were I think he got accused of, was it insider trading or he got banned-
- KRKevin Ryan
No, no, not ins-
- SPSam Parr
Yeah
- KRKevin Ryan
... not insider trading at all. What happened was at the time what was standard there was that, uh, the Wall Street analyst would come pitch the company that was gonna go public, and they would say, "Look, we're gonna great, write great things about you," which is potentially a conflict with their recommendations to their, uh, their, the companies, their investors. So, um, everyone did that. Henry actually wrote internal emails saying, "I feel really uncomfortable with this."
- SPSam Parr
Mm.
- KRKevin Ryan
Which then was used against him. You know, no one else did that, and so legally I don't think he did anything wrong. Uh, I, everything he wrote was approved by his superiors and, and order. But anyway, uh, you know, some people felt like he was tainted. I didn't at all. Um, what I did know is he was an incredible writer and he was a perceptive journalist. He was writing pieces for The Atlantic. I mean, he's just so good. I mean, he's so talented. And he also, he truly understood internet journalism. So the people I interviewed for the Wall Street Journal basically just wanted to redo the Wall Street Journal, and which we don't need. Uh, Henry had, was, was fresh. He had never really worked in a newsroom, which could be viewed as a weakness. I viewed it as a strength. And so he changed the rules, and we were willing to do that, and he did an incredible job.
- SPShaan Puri
You know, that same strategy
- 16:45 – 18:45
What did Buzzfeed get wrong?
- SPShaan Puri
of kind of like start with the content quickly that gets traffic.
- KRKevin Ryan
Mm-hmm.
- SPShaan Puri
Don't try to be-
- KRKevin Ryan
Mm-hmm.
- SPShaan Puri
Don't look for kind of like the peer acclaim in the industry.
- KRKevin Ryan
Mm-hmm.
- SPShaan Puri
Look for what the market wants, and then over time improve the quality. That was also Buzzfeed's strategy. But today I'm looking-
- KRKevin Ryan
Yeah
- SPShaan Puri
... at the Buzzfeed stock, it's 36 cents. It's a $50 million market cap. What do you think they got wrong, or what happened to Buzzfeed? 'Cause it seemed like they were-
- KRKevin Ryan
Oh
- SPShaan Puri
... they had that whole s- that same playbook, and Jonah Peretti, if you ever hear him talk, he seems like, you know, whip-smart in the same way.
- KRKevin Ryan
Y- for me, it's very clear, and I, I felt this from day one even when they were theoretically worth $2 billion. I rarely ran into someone who said, "I love reading Buzzfeed every day." I, I don't believe they built up a true brand. They showed up in search results, they got traffic. But there were, you know, many, many people that religiously read Business Insider every single day. So it just had a brand that I think was much stronger and more defined.
- SPShaan Puri
Mm.
- SPSam Parr
And you, [laughs] you, you guys have another, uh, funny part about you, which is I was telling my wife this 'cause we were talk- I was telling her I was gonna talk to you, and I was gonna, and, and I follow Dave Portnoy on, on Twitter from Barstool. Business Insider is the only one to get one up on him.
- KRKevin Ryan
[laughs]
- SPSam Parr
So you guys had this, you guys had this article-
- KRKevin Ryan
Yeah
- SPSam Parr
... about some s- some stuff that he had done, and he went ape shit.
- KRKevin Ryan
Mm-hmm.
- SPSam Parr
He went crazy.
- KRKevin Ryan
Yep.
- SPSam Parr
And Business [laughs] Insider had the best response, which was no response. You guys didn't reply to anything.
- KRKevin Ryan
[laughs]
- SPSam Parr
And it's the only time I've ever seen Dave Portnoy get one-upped.
- KRKevin Ryan
Yeah. Uh, I wasn't really involved with that whole exchange. That happened after- Uh, I, we sold the company, so
- SPSam Parr
Well, I thought it was pretty funny, and I, uh [laughs] I thought it was ... I thought Business Insider actually handled it wonderfully. A- and they were the first people that I saw that got one over on him.
- SPShaan Puri
You know, you know, Kevin, um, you, you guys have had so many hits come out of the studio. And, um, as somebody who ran
- 18:45 – 29:20
Why has AlleyCorp been such a success compared to other venture studios?
- SPShaan Puri
a studio for six years and, uh, did not have billion-dollar hits come out of it, I gotta know, what's the, uh, what's the secret? What, uh, 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?
- KRKevin Ryan
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, uh, we've had some good ideas. Uh, we do a lot of research. You know, at 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 DAC. 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 like watching, you know, I don't know, a good basketball player or 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.
- SPShaan Puri
Right.
- KRKevin Ryan
So I think we've executed well there. And, you know, we have a bunch of people, including myself, who have a lot of experience doing this. It's just a series of judgment calls. You know, I think, uh, 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 and make sure that they do as well as possible.
- SPShaan Puri
Walk, walk us through, like, one of those ideas. So-
- KRKevin Ryan
Okay, so here, for example, two and a half years ago ... So I'm, uh, I'm very interested in psychedelics for mental health. I'm the leading funder of the Yale Center for Psychedelic Research. You know, I'm involved with a bunch of things, nonprofit research for, you know, m- m- pushing psychedelics for- forward so they can be legalized either by, by the FDA or by state. So with that context, two and a half years ago, I said, "Let's do a deep dive and see if we come up with a for-profit idea." A person on my team works with me, interviews 50 people. You know, we're talking to everyone, and we come up with a solution that was partly influenced by some of the work that's been done at Yale, and we start a company called Transcend. The person on my team, actually, which is unusual, spins out to become the CEO, uh, Blake Mandel. Big article in, uh, The Wall Street Journal about five months ago about Transcend, because we, we started off with a million and a half dollars, but we raised $40 million about a year to a year and a half later in two tranches at 80 million pre. So big, big, big, big step up, big valuation. And we have a compound that you haven't heard of going through the FDA process. It's in phase two trials right now. Uh, and so people are obviously optimistic about the future, like the team, like the execution. Uh, we did some things very well there. We have been awarded patents. For example, if you follow this industry, you know that you can't patent MDMA or mushrooms 'cause those have been around for a long time, but we actually did get a patent for methylone, which is the compound that we're working on. Uh, so, so far, so good. Now, there's still risk, but that company is ... You know, we currently have a $50 million position based on our five million that we've invested so far, and we think it has a lot of potential.
- SPSam Parr
What about, um, like with MongoDB? So, um, that was started, I think, in 2007.
- KRKevin Ryan
Yeah.
- SPSam Parr
So AlleyCorp was, like, a little bit early.
- KRKevin Ryan
Yeah. Yeah.
- SPSam Parr
Did you have a team helping you research ideas back then?
- KRKevin Ryan
No, I didn't. That was purely Dwight, myself, and Elliot Horowitz, who was the most brilliant young engineer at DoubleClick. Now, out of 700 engineers, if you could pick out one person other than Dwight, you would have picked him. And so we started a company together in 2005 called ShopWiki, which is a search engine for shopping. Did okay, not great. We sold it in 2007, made a little bit of money, and then said, "What are we gonna do next?" And so came up with this idea, uh, started working on it. It was a very hard slog. It's very easy to feel good about it right now. For three years, we had zero revenue. So not easy to keep funding, going back to VCs with zero revenue. But we had a lot of people using it, so, you know, we broke through that. But we had some ugly financing rounds. You know, especially back in 2009, 2010, that was not a good time to be raising with z- no revenues. Uh, then finally Sequoia came in, and then we raised a lot of money, and now it does, getting close to a $2 billion run rate.
- SPSam Parr
Did that company make you a billionaire?
- KRKevin Ryan
So, yeah, I mean, look, for all of us, it definitely, uh, yeah, we all made lots of money on that, on that company, definitely.
- SPShaan Puri
Those three years with no revenue, uh, at the time, were you like-
- KRKevin Ryan
Yeah
- SPShaan Puri
... people just don't understand that this thing is, uh, like, others don't see it, but I see it? Or were you, like, in the fog of war, you're like, "I don't know if this is a thing, if this is gonna make it, but, um, you know, let's keep going"?
- KRKevin Ryan
Oh, no, no. I would say that all of us were nervous because, uh, you know, you like to have revenue, or you're gonna run out of money at some point. What helped us on the inside was that, uh, the utilization, the number of people using the product, it was free, was growing every single month all over the world. So there's, you know, probably 50,000 small companies using the product, and so, you know, there were hundreds of meetups about Mongo, and people were showing up. And so we could see in a way that the dogs liked the dog food. Uh, we just needed to then make it good enough that larger companies would pay money for it, and then we got there, and, and the rest is history.
- SPSam Parr
But what's crazy is, like, all right, Business Insider, I understand that well. That's media. I get it perfectly. Gilt, that's commerce. That's fairly easy to understand. Zola, kind of media-ish related, but like a fil-- Like, I understand that business. And then you have, like, psychedelics, which I don't have anything about. But then Mongo is, like, highly technical. I, I, I, I barely even... I don't, I, I don't even know the use case, to be honest. It's a database company, involves SQL. Like, I don't even... I'm so not technical. It's pretty amazing that... Like, are you, are you pretty... I mean, you are now, but were you well-versed on what this idea was, or did you just trust Eliot?
- KRKevin Ryan
So Eliot and Dwight, you know, were the brains and the technical chops. Like, the product could not have been built without them. I understood the high level problem, which I saw, which is that Oracle was not the right database for the future because we were going from structured data to unstructured data. So way to think of that is that if I... You know, you think of a spreadsheet, which is how we all thought about data. But if I told you I have ten thousand videos, can you put that into your spreadsheet? And you're like, "Well, no, actually, it's not built for that." But of course, data was moving that way. YouTube came out in two thousand and five. Video was gonna be enormous. Uh, so I knew that trend was happening. I knew that the Oracle product was extraordinarily expensive for us, and so there had to be a cheaper way. We had seen Linux come out, so that was an open source, you know, operating system that was enormously successful. And so we thought collectively that we needed an open source database that, uh, was, was structured for the future. And so that was the bet. So that I understood. If you said five levels down, do I understand the code? No. But, you know, I was working with... Anytime you start a company, you know, H- like, I'm not a particularly good writer. Henry is, uh, and he was in charge of that product. I knew the market well enough in both cases, high level, and then it's about assembling the team. You've gotta think of yourself as you are the coach, you are not the player. And if you're a coach, and if you manage to persuade, you know, LeBron James and Kevin Garnett and a bunch of people on your team, your team's gonna do well. That's actually the job.
- SPShaan Puri
You, um, y- y- you, like, with the, when you're talking about Transcend and you're like, "We're, we've got a drug going through FDA trials," I had the same reaction I think Sam's having, which is like, man, this guy's pretty fearless. Like, goes into totally different spaces with totally different business models and, um, with, with probably a whole bunch of, like, new things you gotta learn. Um, and even if you're the coach, you know, you're betting money and you need to be able to recruit the right players, and you need to steer the ship. Um, do you feel like fearlessness is something you have, and do you s- do you notice that, like... Do you feel... Like, sometimes I look at other entrepreneurs and I think, "Man, I can't believe they're, 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.
- KRKevin Ryan
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 seventy 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 ten-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 build infrastructure around it, but still most of it goes back to a good idea and, uh, a good team. And when we get that right, yes. And by the way, last one on, on psychedelics. I had done plenty of work. I mean, I- 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 then look, our, what I am thinking about all the time, and everyone here does, is where is the world gonna be in ten 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 'cause 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.
- SPSam Parr
What are you consuming on a daily basis to spot these trends?
- KRKevin Ryan
Yeah, so tons of things. No one thing. I'm on, you know, many, many, uh, newsletters that are industry-focused or general-focused or science-oriented. I, I read forty books a year. I'm in conversations with people all the time where you're, you know, there's a lot of learning. Uh, and then people on my team are more specialized than I am. So, you know, I have two MD MBAs who are head up our healthcare practice and then people below them that have worked in healthcare. So they're thinking of very specific issues that I probably wouldn't, wouldn't think of. And the same is true. I have a person on marketplaces, a person on semiconductors and material science, and a person on developer tools and enterprise software, and two people on social impact. So a lot of what we do is in those areas, and I'm a bigger and bigger believer now of industry focus.
- 29:20 – 39:00
What businesses Kevin’s excited about right now
- KRKevin Ryan
You know, it, it's a, you're, you know, you and I are not gonna think of something that applies to the chemical industry right now. But if that's all you did for six months and interviewed a hundred people, you'd probably come up with some ideas that make sense.
- SPSam Parr
And the industries that you care about right now are health-
- KRKevin Ryan
Healthcare
- SPSam Parr
Uh-
- KRKevin Ryan
Uh, definitely, uh, then the ones I mentioned, so semiconductors and material science, developer tools, uh, with some security, marketplaces, B2B marketplaces, uh, social impact, and robotics and automation.
- SPSam Parr
What's an example of a B2B marketplace that you're interested in?
- KRKevin Ryan
Yeah. So we invest... We have done a deep dive into the maritime industry, so shipping. No one thinks about it. Multi-hundred billion dollars. Very behind in technology. We invested in a company called Boxhub that's a marketplace for those containers that are on container ships. Based in Toronto. Uh, most people wouldn't have known about it. We led that round. We also have just started a company in maritime that's gonna be a e- a procurement marketplace. So you're a ship. Let's say you're arriving in Cartagena. Your boiler breaks. What are you gonna do? Yeah, we weren't, we weren't planning on that. And so having a site you can go to that becomes like sort of the Amazon of that and has delivery and can get you those parts, uh, everyone in the industry told us that that's needed. So we're literally just built a team two months ago, and there are probably four people right now, and so we're off and running.
- SPSam Parr
What's that company called?
- KRKevin Ryan
It's, uh, it doesn't have its official name yet.
- SPSam Parr
So all right, let's use that as an example.
- KRKevin Ryan
Yeah.
- SPSam Parr
So you basically did, uh, did you just go and somehow network your way into talking to 50-
- KRKevin Ryan
Yeah. Oh, yeah, so a woman on my team, uh, absolutely did that, and went to two, uh, maritime conferences. So which she said were fascinating. It's basically people from Venezuela, you know, the Middle East, Russia, you know, from all over the world, Greek, and so trying to understand the industry.
- SPSam Parr
Just, just a bunch of pirates.
- KRKevin Ryan
Yeah, it is. It-
- SPSam Parr
A bunch of pirates walking, hobble, h- hobbling around and a bunch of parrots and bird shit all over the place. [laughs]
- KRKevin Ryan
She said it did not look like her Princeton, uh, reunion at all.
- SPSam Parr
[laughs] Uh... [laughs]
- KRKevin Ryan
So yeah, and so and she met with the couple investors who invest in this space, you know, ship owners, uh, data providers, everyone. They're just trying to understand how does the industry work. And I think there's an advantage sometimes coming from outside because some people just say, "Oh, that's just how it works here." And the person on the outside will be like, "Wait a second, it doesn't have to work that way. You know, we can do better."
- SPSam Parr
Right.
- KRKevin Ryan
And that's why like, you know, Henry was the perfect person coming from outside. You know, when I started Gilt, none of my initial five people had worked in the fashion industry, but we understood the problem. It wasn't that complicated, and so we could create something that was, that was interesting and unusual. Uh, so that's the write-up. We just started a company in assisted fertility. I'm sure you guys know you have friends, you know, who are getting IVF.
- SPSam Parr
I did it.
- KRKevin Ryan
Yeah. My, my brother and his husband, you know, uh, had a child through surrogacy, freezing eggs. That's gonna grow for the next 10 years for all the reasons we know about people having children later, sperm counts are down, a bunch of things. So we d- we si- we started a company, what, uh, four months ago. We put in a, a million and a half dollars, and we just signed a term sheet to raise, you know, five and a half million dollars. Um, a lot of people wanted to do it. People are excited about the team. Uh, we have, you know, good set of people, uh, mostly from Stanford Business School on this team, and it's a big space. So, uh, I'm, I'm gonna bet on that team and that trend for a while.
- SPSam Parr
What does that deck look like? You said they, they do like a... or maybe I think a 50-page memo or deck, I'm not sure what you said. Do you have a structure for it?
- KRKevin Ryan
Yeah. It's generally one just talking about the industry, where are the problems, where are the pain points, and then where are the opportunities, what's the product idea. So one of the reasons I do almost nothing in e-commerce these days is 'cause I don't see the problem. We solved, the industry solved the problem. Meaning if you name anything on the planet Earth just about, you know, you can find a site, they'll have 10,000 of them. It'll be sent to your house by tomorrow. Man, I don't know how to do better. That problem is solved. Whereas when I, you know, when I started Gilt, you actually couldn't get Marc Jacobs at 50% off online. Uh, just no one offered it, and so we offered it, and people went crazy over that. Uh, so e- e-commerce is very mature. Frankly, media is pretty mature right now. There's a lot, you know-
- SPSam Parr
Right
- KRKevin Ryan
... not that many people say to me, "I just can't find what I wanna, wanna read." Uh, but even, you know, once in a while, we're working on one idea right now, the early stages in the media space, uh, but not, not sure yet. So we're looking for problems. The health... One of the reasons I like healthcare is because it, healthcare is not solved. You know, as you guys know, you, you have knee surgery, either you or your insurance company are gonna pay a crazy amount. One, there's too much knee surgery. It's gonna, someone's gonna pay 40,000, yet in France it's 20,000 and the results are better. So can it be done better? Yes, it can be done better. Do 20 times more Black women die in childbirth than in Sweden? Yes. Is that something that is just inherent and is always gonna happen? No. We don't do enough prevention. There are many structural issues in healthcare that have not been solved, and we're, we're solving some of them.
- SPSpeaker
[upbeat music] Our software is the worst. Have you heard of HubSpot? See, most CRMs are a cobbled-together mess, but HubSpot is easy to adopt and actually looks gorgeous. I think I love our new CRM. Our software is the best. HubSpot. Grow better.
- SPShaan Puri
It sounds to me like what you do is you l- think about what's the world gonna look like in 10 years. Um-
- KRKevin Ryan
Yeah
- 39:00 – 41:00
Thoughts on buy vs. build vs. bootstrap
- SPSam Parr
plugins, basically, that-
- SPShaan Puri
Basically bootstrapped a unicorn.
- KRKevin Ryan
Wow, amazing.
- SPSam Parr
And, well, of which he owns most of.
- KRKevin Ryan
Yeah.
- SPSam Parr
Um, and so w- we have a lot of, like... And, and, and I fall in this category as well. I, I bootstrap a lot of my things.
- KRKevin Ryan
Mm-hmm.
- SPSam Parr
Um, and then there's this other category. So there's this category of people who, like, bootstrap stuff and just use their cash flow, and then oftentimes that same group of people prefer to go and buy companies as opposed-
- KRKevin Ryan
Yeah
- SPSam Parr
... to build them from scratch. You're taking the opposite approach a little bit, where you're like, "Uh, I'm gonna fund it. It's not gonna make money at first-
- KRKevin Ryan
Mm
- SPSam Parr
... but I'm... And I might go and raise a, a, a shit ton more money-
- KRKevin Ryan
Mm
- SPSam Parr
... but this might be a huge idea-
- KRKevin Ryan
Yeah
- SPSam Parr
... and I'll own a small piece of it." What, um... Like, have you ever considered the bootstrapping model, or is your, is your... You just go big right away. And have you ever considered buying? What's your, like, buy vs. build kind of mindset?
- KRKevin Ryan
Yeah. So it really depends on the type of business. So if you're running an agency, you just don't need a lot of capital. You know, you hire five people who, uh, and then they, they... Agencies make money, and then you use that money to reinvest and grow. If you're building... What I'm building is closer to, like, a hotel. You know, you have to build the whole building before anyone comes and stays with you. So little different, 'cause, like, Mongo, you gotta take years to build a good enough product, and there's no way to bootstrap that. You know, it takes 20, 50, you know, there's $100 million generally for those types of companies to get there. So that's why it's, it's not an option for those things. Look, I would love to have companies that, you know, I could own all of. Um, for example, the, the agency that, that I have, I said those engineers. I basically have an outsourced engineering company. I own all of that, uh, because it has clients and it builds as it gets more clients. But those businesses are not as scalable. Profit margins are generally lower. Um, those are not the type of businesses I generally go after.
- SPSam Parr
Why, why is that? Is it just a matter of you just enjoy something more? Do you think that one is a better, better wealth creation? Are you mo- I mean, what, what's the motivation?
- KRKevin Ryan
I just prefer creating a product, a real
- 41:00 – 42:50
What business has been the easiest and most profitable?
- KRKevin Ryan
product that's hard, uh, and then, you know, making it more scalable and building it up over time. The vast majority of quite successful companies are in that category. The services-oriented companies, you know, it's harder, it's harder to get to be a unicorn. It can happen, but there aren't, there aren't that many.
- SPShaan Puri
Have you over time gotten more selective on the project selection? 'Cause I look at, you know, you did Business Insider. I think you were the C-
- KRKevin Ryan
Yeah
- SPShaan Puri
... were you the CEO for, like, a, a period of time there, nine years? Is that right? No.
- KRKevin Ryan
No, I was the chairman for all nine years. I did step in, I did step in to be the CEO of Gilt when we were growing really quickly. I just-
- SPShaan Puri
Right
- KRKevin Ryan
... decided that I was the right person at that point for probably two or three years. But otherwise, I've been chairman of many companies for 15 years. I stepped into Mongo. I changed CEOs about eight years ago, uh, and for three months I was de facto the CEO as I was doing this-
- SPShaan Puri
So you've, you've run these for a period of time, but mostly not. Um, but, but I guess, uh-
- KRKevin Ryan
Yeah
- SPShaan Puri
... when I think about businesses, I look at my career and it's like I look back and I think, okay, of these 10 things I did, two of them were, like, ate up all of my time and gave me a bunch of gray hair for, like, relatively less payoff, versus these other two, which was, like-
- KRKevin Ryan
Yeah
- SPShaan Puri
... I just kind of wrote the check. It was an obvious opportunity and it just paid me, and it was wonderful. Have you... Like, what's the best business that you've done in your portfolio that you look back on that has the combination of the value, the pain that it took to get there, you know, um, all, all of that? And then do you have a framework around that or do you think it's just luck of the draw?
- KRKevin Ryan
I think it's luck of the draw. I mean, Mongo is the one where, you know, I got the most return for the least amount of money. I mean, I, I essentially never worked there full time. Uh, so chairman for 13 years, um, and yet it's a super valuable and, you know, fascinating company that's gonna be around for the next 50 years. Uh- But you know, I, I'm intellectually curious,
- 42:50 – 44:50
Thoughts on AI
- KRKevin Ryan
so what I love about what I do is that, you know, in an hour I might be in a meeting on psychedelics, and then on, you know, semiconductors, and I have to try and keep up and learn something about these. Um, and that's what's so... You know, we have one in cardiology. Uh, there's so many different things. It's, that's what's amazing.
- SPShaan Puri
And for someone who's thinking about 10 years, I'm s- a little surprised I don't see AI all over this doc. Uh, you know, you're not saying, "AI, AI, AI."
- KRKevin Ryan
No.
- SPShaan Puri
It sounds like it might be embedded in some of these-
- KRKevin Ryan
No
- SPShaan Puri
... 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?
- KRKevin Ryan
No, I, I'd say two things. One, it, 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 $100 million 'cause we're gonna 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 gonna be much more mundane. It's optimizing customer support, you know, making your coding more efficient, the 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.
- SPShaan Puri
Shaan, Shaan did that, too.
- KRKevin Ryan
Yeah, I did the same thing. I shut down for a week. Yeah, just to get up to speed, 'cause it is a very important thing that we all need to be thinking about. And then came back, you know, compared notes, and made sure that our, our companies are thinking about it.
- SPShaan Puri
Did you do it, too, or just the engineers?
- KRKevin Ryan
I d- well, no, these are not engineers. This is the, the investment people on the, on the tech side. So I do it on a more continual basis. You know, I'm spread thinner than other people, so you know, I have 60 board meetings a year. I have a lot of things I have to... I can't shut down as easily, unless I'm at Burning Man or in Antarctica. [laughs]
- SPShaan Puri
[laughs] Yeah.
- KRKevin Ryan
Yeah.
- SPShaan Puri
As one does. [laughs]
- 44:50 – 47:40
Launching 8 companies a year
- SPSam Parr
Nice flex. I love that.
- SPShaan Puri
[laughs]
- KRKevin Ryan
Then I'm, then I'm, then I'm, then I'm off the grid, and I don't have a choice.
- SPShaan Puri
[laughs]
- SPSam Parr
[laughs]
- SPShaan Puri
I'm gonna change all of my, uh-
- SPSam Parr
Yeah, same
- SPShaan Puri
... my, my, uh, auto-reply things to I'm in Antarctica, even though I'm just actually in Tahoe.
- SPSam Parr
Yeah. [laughs]
- KRKevin Ryan
No, that's the only two times I'm truly off the grid.
- SPSam Parr
You, uh, [laughs] you, you, like, violate this rule that I have for myself, and, uh, you, you do it so wonderfully, which is focus.
- KRKevin Ryan
Mm-hmm.
- SPSam Parr
Or at least it appears as, as you do. You, like, launch, like, I don't know, how many companies a year do you launch?
- KRKevin Ryan
Eight.
- SPSam Parr
Eight? Goddamn. And you could do eight now, but I, I don't know how big your team was early on. But it seemed like you were still creating a lot of companies.
- KRKevin Ryan
I mean, generally it was one a year, one a year. Um, there was that one year where we did three between the two of us. Uh, but I would never be able to do eight on my own. I mean, they, they take real time.
- SPSam Parr
If we were, if the roles were reversed-
- KRKevin Ryan
Mm-hmm
- SPSam Parr
... you know, I look up to you, if you were a 23-year-old and, and you looked up to me, I would say, "Man, you gotta do one thing well-
- KRKevin Ryan
Yeah
- SPSam Parr
... and that will pay more dividends."
- KRKevin Ryan
I agree.
- SPSam Parr
Oh, well, great. So what's your, like, opinion on that, then?
- KRKevin Ryan
No, no, so I think that anyone... I, I, I, and people come to me all the time and say, "Look, I would like to have a studio like you," and I'd say, "Look, don't do that. Start by trying to s- start a successful company and end up not being the CEO." That's already not that easy. You know, if you have that, and six months later the company has raised its external round of financing, has a full management team in place, and you are the chairman, you can then decide to do another one. You know, you can't truly be CEO of multiple companies, but you can be chairman of multiple companies, but you gotta start with one. And if you try and do two or three at the same time on your own, it's not gonna work. It's not that easy. You know, I have 25 people.
- SPShaan Puri
What, what does a chairman actually do?
- KRKevin Ryan
So a chairman is one, the, in this case, is the ultimate person that's gonna be around 15 years from now. The CEO may change. This is a person that's gonna guide it and is a co-founder. You know, if along the way somehow Henry Blodget had quit, that's my problem. I need to find a CEO. I need to solve that for the board. So you're just the most active board member. We had other investors, but everyone knows, like, I have one company that is gonna have a tricky financing round, and, uh, we need to get the in- the, uh, the internal investors together. It's not gonna be easy. I need to do that. So I'm having calls with all of them. I need to wrangle everyone, encourage them, push them, come up with the right thing.
- SPSam Parr
Well, and what, what type of relationship do you have with your CEOs? Like, before it's, like-
- KRKevin Ryan
Yeah
- SPSam Parr
... uh, you know, in the first one, two, three, four years, how often are you working with them?
- KRKevin Ryan
Yeah so, I mean, there, uh, we're gonna have a call probably every week or every two weeks soon to, to touch base, and then they reach out if they need something. I mean, I love the relationship. I feel great about the relationship because, you know, I don't want their job. If I wanted their job, I would've, I would've taken their job. Um, I want them to succeed. I don't,
- 47:40 – 50:20
Why Kevin isn’t on social media
- KRKevin Ryan
you know, I don't wanna be CEO of one company, and hopefully I can stay out of the way 'cause they know much more about the company than I do. But there's certain things where I have either relationships, some experience, tricky issues, uh, uh, introduction to a VC firm, where I can add value. Uh, and so I, I love that relationship.
- SPSam Parr
Uh, I like you so much because you do things... Okay, so Shaan and I are in this, like, stupid Twitter world-
- KRKevin Ryan
Mm-hmm
- SPSam Parr
... where, like, a lot of our friends are popular on the internet.
- KRKevin Ryan
Yeah.
- SPSam Parr
And there's this whole thing that I don't buy into of, like, build in public, and, like, use your audience. But, like, it's people selling, like, $100 a month things or something like that, and you have these, like, really big ideas. But also, like, for how successful you are, we take pride in, like, finding interesting people who are, like, amazing but not incredibly well known. You are really good. You're, you're one of the higher people on this ratio of, like, pretty low-key, under the radar, but has had massive impact.
- KRKevin Ryan
Exactly what I want.
- SPSam Parr
And, like, you don't have an audience.
- KRKevin Ryan
Mm-hmm.
- SPSam Parr
Like, you, you violate all these, like, stupid rules that people talk about.
- KRKevin Ryan
Yeah. I do no social media.
- SPShaan Puri
Why is that?
- KRKevin Ryan
You know, it's, I... Look, I think other people use it very well, and they like doing it. I don't wanna spend the time. Uh, I don't wanna do it. I don't wanna, I don't need to be out there. Uh, I, that time should be used for thinking time and managing time. Uh, and so yeah, no, the people who are on my marketing team know that the goal is that we are very successful, and that when I walk into a restaurant, no one knows who I am.
- SPSam Parr
Yeah. I mean, I, I just think it's awesome. We're, uh, well, I, I... But you, you're on, like, CNBC and shit like that every once in a while. I'll, I'll see you there.
- KRKevin Ryan
Yeah.
- SPSam Parr
I think there was rumors that you're, you were gonna run for mayor. W- is that true?
- KRKevin Ryan
So, uh, two different things. One is you haven't seen me on TV in a long time.
- SPSam Parr
G- right. Yeah, that was y-
- KRKevin Ryan
Yeah
- SPSam Parr
... that was about four or five years ago.
- KRKevin Ryan
Yeah.
- SPSam Parr
When, when, I think I was, like, leaving your office or something like that-
- KRKevin Ryan
Yeah
- SPSam Parr
... in the Yahoo building, or maybe I was at a friend's.
- KRKevin Ryan
Yeah.
- SPSam Parr
I saw you on TV.
- KRKevin Ryan
Yeah, that'd be right. I don't think I've been on for at least five years, so yeah, I don't do that. You know, actually, podcasts are the only thing I do because it's sort of enjoyable. You don't need to prepare. You have a good conversation. Uh, so I've done that, but I, other than that, I do almost nothing. I did, uh, think about running for mayor, you know, eight years ago. I've been very involved in politics in many ways, um, representing tech community in, in every dimension. Um, all my life I thought I would wanna, that'd be the one other thing I'd wanna do, and then decided, you know, seven years ago that I didn't wanna do that. It's, it's a miserable process. You know, if you said to me, "You could be mayor tomorrow," I would actually do it. If you said to me, "No, no, what I mean is that you can be one of seven candidates."
- SPSam Parr
[laughs]
- KRKevin Ryan
You can spend eight months
- 50:20 – 54:20
Starting companies in the recruiting space
- KRKevin Ryan
getting the shit kicked out of you and being humiliated.
- SPSam Parr
You're like, "Uh, I'm gonna be in Antarctica that week."
- KRKevin Ryan
[laughs]
- SPSam Parr
"Sorry, guys."
- KRKevin Ryan
Yeah.
- SPSam Parr
It's like, "Can we do this next week?" [laughs]
- KRKevin Ryan
No, no, you're, you're telling me I can't go see my kids who are, you know, at various points all over the world, and I get to see them all the time. Uh, we do great things together. Uh, and so that's a big trade-off that I don't wanna make anymore.
- SPSam Parr
Mm.
- KRKevin Ryan
So I'm gonna keep doing what I'm doing for a long time.
- SPSam Parr
You were involved in one company, um, that I always, that I think could still work.
- KRKevin Ryan
Mm-hmm.
- SPSam Parr
And it didn't work, uh, but you almost had it. So you invested or were a board member. You were heavily involved in, I think, in HotJobs, which-
- KRKevin Ryan
Yeah
- SPSam Parr
... had an exit.
- KRKevin Ryan
Yeah.
- SPSam Parr
But you, you did this other one called, uh, The Ladder or Ladders-
- KRKevin Ryan
Yeah
- SPSam Parr
... where at the... This was in the mid-2000s where, like, $100,000 job was considered good.
- KRKevin Ryan
Yep.
- SPSam Parr
And it was like, I think if I remember correctly, I don't remember if the user paid or if the job company paid, but it was a job board. But it w- that's kind of dismissing it.
- KRKevin Ryan
Yeah.
- SPSam Parr
But it was a job site for $100,000 jobs.
- KRKevin Ryan
Yep.
- SPSam Parr
And I remember seeing that. I was like, "That's pretty cool." And I tried launching a company where the user would pay a subscription-
- KRKevin Ryan
Mm
- SPSam Parr
... and then the editorial person would try to survey and, uh, and effectively find out what it's like to work there, as opposed to the company-
- KRKevin Ryan
Yeah
- SPSam Parr
... uh, like, telling you the best, the best, um-
- KRKevin Ryan
Mm-hmm
- SPSam Parr
... like, you know, like, the, the best stuff. But I always, you're always in... You had a couple companies in, like, the job space.
- 54:20 – 56:20
The benefit of being emotionally stable
- KRKevin Ryan
where I'm not close to the companies, 'cause what I enjoy is when I'm close to the companies and the problems, and that's where I think I, I add value.
- SPSam Parr
Hm.
- KRKevin Ryan
I'm just trading off... I'm very old at this point in this industry, and so I'm, you know, r- 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.
- SPSam Parr
An- a- another thing that I like about you is that, um, you're very emotionally stable. Like, every time-
- KRKevin Ryan
Yeah
- SPSam Parr
... you know, I've only talked to you three times, but, like, you are quite logical, and, like, you seem like a guy who isn't rattled. And I read an article about Business Insider selling, and I think, uh, the article said, "Henry Blodget is a very emotional person," which is, makes sense 'cause he's a journalist.
- KRKevin Ryan
Yeah.
- SPSam Parr
He's, he's a great writer. And during the sale, I think someone was... I think he was like, "I'm not even talking to Axel Springer," or whoever bought it.
- KRKevin Ryan
Yeah.
- SPSam Parr
"Uh, Kevin has to do it."
- KRKevin Ryan
Yes.
- SPSam Parr
Like, I, I just, I can't even be in that room.
- KRKevin Ryan
Yeah.
- SPSam Parr
And, like, it was like, all right, Kevin steps in, and he's the reasonable one, or he's, like, the emotionally, uh, like-
- KRKevin Ryan
No, I, I negotiated, I negotiated the entire deal. Uh, and you know, and look, I could not be a bigger fan than I am of Henry's. But it would be like if, if someone kidnapped your daughter, uh, are you a good negotiator with the other side? And the answer is no, right? You're like, "Give them everything."
- SPSam Parr
[laughs]
- KRKevin Ryan
Uh, you know, "Just get her back." So we need someone else to do that. And so, um, it was better for me to do it. He was very nervous 'cause I was pushing to get a higher price. Uh, and but which we did. You know, we were doing 40 million at the time. We sold it for 11 times revenues, which is a big, big number for a media property.
- SPSam Parr
It's insane.
- KRKevin Ryan
Yeah.
- SPSam Parr
It's insane.
- KRKevin Ryan
Um-
- SPSam Parr
We're, we're good friends with, uh, one of our best friends is Austin Rief, the founder-
- KRKevin Ryan
Mm-hmm
- SPSam Parr
... of Morning Brew.
- KRKevin Ryan
Yeah.
- SPSam Parr
And, and they're, they're killing it for, for BI.
- KRKevin Ryan
Killing it.
- SPSam Parr
And, uh-
- KRKevin Ryan
Great. That happened after me, but great acquisition. Uh, I still get that product every day. I think they do a really nice job, have a great editorial tone. But you're right, I'm, I'm, don't, I mean, this... I think it's important to not get too emotional about any one company, and
- 56:20 – 1:00:10
Kevin’s investment portfolio
- KRKevin Ryan
that's one of the things I can bring to the table. And when you're CEO, you're just so close to it. You're, you're, you're in the forest. I can step back a little bit and sometimes say, "Look, you know, this is gonna be bigger than you think, and we should, you know, double down," or, "It's not working, and let's figure out a way to sell this."
- SPSam Parr
Right.
- KRKevin Ryan
It's easier for me.
- SPSam Parr
A, a question that we, uh, that we like to ask people is, like, what do you do with your money? So, like, if, if, you know, of your, of your pie chart, of your 100%-
- KRKevin Ryan
Yeah
- SPSam Parr
... portfolio, how do you, how do you allocate, uh, to different stuff? You know, do you have public equities and just normal bonds and stuff?
- KRKevin Ryan
No.
- SPSam Parr
Are you all in on private company? What are you doing?
- KRKevin Ryan
All in on private companies. So probably 90% of my net worth is just in my own firm in, in investing in various companies and things. Uh, I have a li- I have some in, in some VC and private equity firms, you know, as an LP. Uh, you know, and I do have some real estate. Uh, I bought a building, a commercial real estate building, uh, between, on Mott and Broome, in between Soho and Bowery. And so when you come visit in a year, that'll be the AlleyCorp headquarters. There'll be a restaurant in the, in the ma- in the, in the retail floor, five floors of commercial real estate, and an amazing roof deck with parties for 150 people and dinners for 30 people up there. So it's gonna be a real tech center. So we're re- It, it was a shell of a building, and construction starts in a week. We've designed it over the last, uh, nine months. It's a super fun project, but it's also a diversification for me in owning some real estate.
- SPSam Parr
But you don't have any public e- public equities-
- KRKevin Ryan
No
- SPSam Parr
... uh, other than, I imagine you still own stock in, uh, Mong- uh-
- KRKevin Ryan
Yes
- SPSam Parr
... Mongo-
- KRKevin Ryan
Yes
- SPSam Parr
... but, but, like, you don't o- you don't have any, uh, boring-
- KRKevin Ryan
Nope
- SPSam Parr
... uh, indexes.
- KRKevin Ryan
No.
- SPSam Parr
Really? Are you heavy on cash?
- KRKevin Ryan
Yes. I always keep a lot of cash. I need to keep a lot of cash because I don't have, you know, I don't have a salary, so, and I don't know when money's coming back.
- SPSam Parr
Where do you keep your cash? Just in a, in a, in-
- KRKevin Ryan
Yeah
- SPSam Parr
... as simple as a high yield savings account?
- KRKevin Ryan
Yep, yep, exactly. I need to be super liquid.
- SPSam Parr
Dude, that's so fascinating.
- KRKevin Ryan
This is awesome.
- SPSam Parr
This is awesome.
- SPShaan Puri
Kevin, thanks so much for coming on. We, uh, as you can tell, big fans, and what you've done is, is pretty incredible. Also, I think there's just, like, what you do about thinking about where the world is going, what ideas, what opportunities, what problems.
- KRKevin Ryan
Mm.
Episode duration: 1:00:10
In the uListen app, the transcript lights up word by word as you listen. Get uListen
Transcript of episode 0cLWUCE02KE
