00:00

You you, like, violate this rule that I have for myself. And, you you do it so wonderfully, which is focus, or at least it appears as as you do. You, like, launch, like, don't know how many companies a year do you launch?

You you, like, violate this rule that I have for myself. And, you you do it so wonderfully, which is focus, or at least it appears as as you do. You, like, launch, like, don't know how many companies a year do you launch?

00:12

Eight.

Eight.

00:13

Eight. Goddamn.

Eight. Goddamn.

00:22

Alright. We're live, Kevin. Do you this is Kevin Ryan. Do you remember me?

Alright. We're live, Kevin. Do you this is Kevin Ryan. Do you remember me?

00:27

I don't remember where we met. I know we've met, but I don't remember where. That's good. Okay. You don't have to remember. So, basically, I'm gonna tell you why. This is funny. So, basically,

I don't remember where we met. I know we've met, but I don't remember where. That's good. Okay. You don't have to remember. So, basically, I'm gonna tell you why. This is funny. So, basically,

00:37

I've studied you for maybe ten years. So you started, you were the president of,

I've studied you for maybe ten years. So you started, you were the president of,

00:42

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 four I think, twenty eight billion today. One's worth,

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 four I think, twenty eight billion today. One's worth,

00:51

you have a couple of billion dollar exits, but you started business insider. And I cold emailed you maybe fifty times

you have a couple of billion dollar exits, but you started business insider. And I cold emailed you maybe fifty times

00:58

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. And one of those emails, you finally replied,

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. And one of those emails, you finally replied,

01:07

And you just said, like, thanks for the updates, whatever.

And you just said, like, thanks for the updates, whatever.

01:10

And then

And then

01:11

I lied, and I said, I'm gonna be in New York tomorrow. Can I get twenty minutes of your time? And you let me do that. And I came to your office for literally twenty or thirty minutes. We had such an impactful conversation, and then you did another follow-up call with me. And I have the note from those calls. And this was in two thousand seventeen,

I lied, and I said, I'm gonna be in New York tomorrow. Can I get twenty minutes of your time? And you let me do that. And I came to your office for literally twenty or thirty minutes. We had such an impactful conversation, and then you did another follow-up call with me. And I have the note from those calls. And this was in two thousand seventeen,

01:28

and you made a bunch of predictions about my life as well as the media business and a few other things that were one hundred percent true,

and you made a bunch of predictions about my life as well as the media business and a few other things that were one hundred percent true,

01:36

and I refer back to that note sheet on a consistent basis to help make some decisions. Oh, Interesting. So I'm glad I've sometimes I get lucky and I get it right. And you wanna know what? Your your PR people cold emailed us to get you on the pod. The tables have turned, my friend. Welcome to my world. Exactly.

and I refer back to that note sheet on a consistent basis to help make some decisions. Oh, Interesting. So I'm glad I've sometimes I get lucky and I get it right. And you wanna know what? Your your PR people cold emailed us to get you on the pod. The tables have turned, my friend. Welcome to my world. Exactly.

01:55

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. And, Kevin,

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. And, Kevin,

02:05

you don't know me, but I I did not stock you. I did not cold email you. In fact, I was a little bit,

you don't know me, but I I did not stock you. I did not cold email you. In fact, I was a little bit,

02:11

just jealous of you because I was, at the time, working in a, when Sam was telling me about you, was working at a startup incubator studio. And so we were launching four or five companies a year. And,

just jealous of you because I was, at the time, working in a, when Sam was telling me about you, was working at a startup incubator studio. And so we were launching four or five companies a year. And,

02:23

after three, four years, I was I don't know if this model even works. I just feel like it's like this because there's something inorganic about the studio model versus, like, just a normal startup that that comes from an entrepreneur solving their own 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, I guess I should shut up and,

after three, four years, I was I don't know if this model even works. I just feel like it's like this because there's something inorganic about the studio model versus, like, just a normal startup that that comes from an entrepreneur solving their own 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, I guess I should shut up and,

02:43

just, you know, not the model. That's the problem. It's me.

just, you know, not the model. That's the problem. It's me.

02:46

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 stuff the studio model work when very few people have been able to do that. Yeah.

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 stuff the studio model work when very few people have been able to do that. Yeah.

02:56

No. No. I still enjoy it.

No. No. I still enjoy it.

02:59

By and large, it's 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.

By and large, it's 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.

03:11

There are many problems in society that have not been solved. And, basically, the high level story of you is you,

There are many problems in society that have not been solved. And, basically, the high level story of you is you,

03:17

you have, like, a normal corporate career, but then you kinda, like, worked your way into, double click -- Yeah. -- which eventually I think became ad AdWords at Google. Exactly. Yeah. So Google bought it for about three billion dollars in two thousand seven. The company started in nineteen ninety six. I was there for nine years. It was public for seven years. First four years went from ten people when I joined to two thousand,

you have, like, a normal corporate career, but then you kinda, like, worked your way into, double click -- Yeah. -- which eventually I think became ad AdWords at Google. Exactly. Yeah. So Google bought it for about three billion dollars in two thousand seven. The company started in nineteen ninety six. I was there for nine years. It was public for seven years. First four years went from ten people when I joined to two thousand,

03:38

we're so crazy in twenty five countries. So that's why I said my early thirties doing.

we're so crazy in twenty five countries. So that's why I said my early thirties doing.

03:43

Then we spend three years bringing back to a thousand people as the internet collapsed and seventy percent of our clients went bankrupt. So don't do that.

Then we spend three years bringing back to a thousand people as the internet collapsed and seventy percent of our clients went bankrupt. So don't do that.

03:52

Then we we had huge market share controlled

Then we we had huge market share controlled

03:55

basically add technology. And so then, Google bought it. And then I started,

basically add technology. And so then, Google bought it. And then I started,

04:00

businessider,

businessider,

04:01

Yamongo, and guilt. I wanna point one thing out of it in this journey, by the way.

Yamongo, and guilt. I wanna point one thing out of it in this journey, by the way.

04:06

Your career starts at provincial.

Your career starts at provincial.

04:08

So shout out to all the listeners out there who are in boring companies right now, boring huge companies, consultants, and bankers out there. There is hope for you yet

So shout out to all the listeners out there who are in boring companies right now, boring huge companies, consultants, and bankers out there. There is hope for you yet

04:16

So you did, like, prudential

So you did, like, prudential

04:19

Euro Disney blah blah blah. And then you joined doubleclick as employee twenty, but you you they brought you in, I guess, as a senior person at the time. Yeah. Yeah. What happened is I had launched an internet website for E.W. Scripps, which is a media company, and I was a COO and CFO of a division of that Wasn't it basically just, like, Dilbert comics? Or it was I think. Yeah. Dilbert comics. And and as 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,

Euro Disney blah blah blah. And then you joined doubleclick as employee twenty, but you you they brought you in, I guess, as a senior person at the time. Yeah. Yeah. What happened is I had launched an internet website for E.W. Scripps, which is a media company, and I was a COO and CFO of a division of that Wasn't it basically just, like, Dilbert comics? Or it was I think. Yeah. Dilbert comics. And and as 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,

04:46

advertising,

advertising,

04:48

e-commerce, so things that were not that easy to do because we didn't have the vendors at the time. I went to the parent company and said, look, we should build up an internet division. And they said, no. And so I thought, you know, I actually believe that the internet's gonna be a huge, which is obvious now, but a huge part of the next twenty five 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 within starting

e-commerce, so things that were not that easy to do because we didn't have the vendors at the time. I went to the parent company and said, look, we should build up an internet division. And they said, no. And so I thought, you know, I actually believe that the internet's gonna be a huge, which is obvious now, but a huge part of the next twenty five 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 within starting

05:13

my own company. I became the the c the CFO, the president, and then the CEO. And then when we met, you basically

my own company. I became the the c the CFO, the president, and then the CEO. And then when we met, you basically

05:21

you you kind of outlined after selling Doubleclick, you said basically my partner, Dwight and I,

you you kind of outlined after selling Doubleclick, you said basically my partner, Dwight and I,

05:27

we came up with this thing where we called it Alley Corp, and we're like, you we get, like, two or three, maybe even one good idea a year, and then we find good people and we give them three hundred thousand dollars.

we came up with this thing where we called it Alley Corp, and we're like, you we get, like, two or three, maybe even one good idea a year, and then we find good people and we give them three hundred thousand dollars.

05:39

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 five hundred million dollar exit. You did it with Zola, which is still running and kicking ass, I believe. You did it with with guilt -- Yeah. -- which I think got to, like, five hundred million in sales, but it didn't end up working out wonderfully. I think you said Yeah. We when we sold for two hundred and fifty million, which was less than we thought, but it's still, obviously, you know, a real number. 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 two thousand eighteen. I said three hundred thousand, and that was wrong. Right? Yeah. So we started each company with a million dollars. So five hundred thousand from each one of us, and that was for guilt, business insider, and Mongo.

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 five hundred million dollar exit. You did it with Zola, which is still running and kicking ass, I believe. You did it with with guilt -- Yeah. -- which I think got to, like, five hundred million in sales, but it didn't end up working out wonderfully. I think you said Yeah. We when we sold for two hundred and fifty million, which was less than we thought, but it's still, obviously, you know, a real number. 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 two thousand eighteen. I said three hundred thousand, and that was wrong. Right? Yeah. So we started each company with a million dollars. So five hundred thousand from each one of us, and that was for guilt, business insider, and Mongo.

06:21

And then we'd I did after that, Dwight semire retired, and so I did that with,

And then we'd I did after that, Dwight semire retired, and so I did that with,

06:28

nomad. I did that with Zola.

nomad. I did that with Zola.

06:30

And now by now, I put about a million and a half dollars in each company when we start them. Which isn't a significant amount of money for how big I mean, I MongoDB right now trading. I think it I think its market cap is twenty six billion dollars today. I'm sure at at COVID peak, it was, like, forty or fifty. That that's not a lot of money for the outcomes. No. No. And, you know, look, we had to raise a lot of money. I mean, Mongo between being a private and public company

And now by now, I put about a million and a half dollars in each company when we start them. Which isn't a significant amount of money for how big I mean, I MongoDB right now trading. I think it I think its market cap is twenty six billion dollars today. I'm sure at at COVID peak, it was, like, forty or fifty. That that's not a lot of money for the outcomes. No. No. And, you know, look, we had to raise a lot of money. I mean, Mongo between being a private and public company

06:53

raised and lost a billion dollars

raised and lost a billion dollars

06:56

before they had a profitable quarter.

before they had a profitable quarter.

06:58

And now already make three hundred million dollars a year in profits.

And now already make three hundred million dollars a year in profits.

07:03

So that's why it's so valuable is because it's an it's just an incredible company growing quickly enormous market share and is gonna grow for the next ten years. It'll be a fifty billion dollar Well, you told me in our call, you said,

So that's why it's so valuable is because it's an it's just an incredible company growing quickly enormous market share and is gonna grow for the next ten years. It'll be a fifty billion dollar Well, you told me in our call, you said,

07:15

one of my notes is, basically,

one of my notes is, basically,

07:17

if you're not hiring

if you're not hiring

07:18

fast enough, And and by the way, this is, like, this is the VC route. But you said if you're not if you're not hiring fast enough and losing money, AKA investing,

fast enough, And and by the way, this is, like, this is the VC route. But you said if you're not if you're not hiring fast enough and losing money, AKA investing,

07:29

you either haven't figured it out or you don't believe that your idea is good enough.

you either haven't figured it out or you don't believe that your idea is good enough.

07:35

And so you need to grow grow fast sir. Well, and but you you don't wanna grow fast just to grow fast.

And so you need to grow grow fast sir. Well, and but you you don't wanna grow fast just to grow fast.

07:41

If you have a good idea and if you're hiring a salesperson who costs hundred fifty thousand, and they're selling five hundred thousand dollars worth, you need to hire those people all day long because 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 a thousand people or a few thousand people

If you have a good idea and if you're hiring a salesperson who costs hundred fifty thousand, and they're selling five hundred thousand dollars worth, you need to hire those people all day long because 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 a thousand people or a few thousand people

08:02

to do a billion dollars in revenue.

to do a billion dollars in revenue.

08:04

Well, you and you your analogy was, you go, look, if I if my idea is good enough, I'm gonna build a machine that turns one dollar into two dollars. Yep. 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. Exactly.

Well, you and you your analogy was, you go, look, if I if my idea is good enough, I'm gonna build a machine that turns one dollar into two dollars. Yep. 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. Exactly.

08:20

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, 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 thirty percent of the people in the last year,

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, 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 thirty percent of the people in the last year,

08:38

Because given this market and what they were doing, we had too many people. So there's also a note in that call that I thought was really useful. So I'm looking at Sam's notes from your call, like, back in twenty sixteen. Sam's building the hustle. He's trying to figure out what to do next. I I assume you were considering raising money because you wrote this down, and I thought it was

Because given this market and what they were doing, we had too many people. So there's also a note in that call that I thought was really useful. So I'm looking at Sam's notes from your call, like, back in twenty sixteen. Sam's building the hustle. He's trying to figure out what to do next. I I assume you were considering raising money because you wrote this down, and I thought it was

08:56

It's obvious when you hear it, but I I most entrepreneurs, I don't think think this way, which is you said, let's say you're gonna raise two million dollars at a twenty million dollar value So you're gonna dilute ten percent.

It's obvious when you hear it, but I I most entrepreneurs, I don't think think this way, which is you said, let's say you're gonna raise two million dollars at a twenty million dollar value So you're gonna dilute ten percent.

09:08

And you're saying you just have to ask yourself, if I took that two million dollars and I invested it into growth, people, whatever,

And you're saying you just have to ask yourself, if I took that two million dollars and I invested it into growth, people, whatever,

09:14

over the next eighteen months, is our company gonna be worth more than ten percent versus if we do not? And if it is, then I need to do that. I should do that trade. And if it's not, I should not. And,

over the next eighteen months, is our company gonna be worth more than ten percent versus if we do not? And if it is, then I need to do that. I should do that trade. And if it's not, I should not. And,

09:24

Did I capture the the logic properly there? Yeah. No. Exactly. That's what you have to look at. And, you know, you don't you don't wanna raise too much in that round because you sold ten million

Did I capture the the logic properly there? Yeah. No. Exactly. That's what you have to look at. And, you know, you don't you don't wanna raise too much in that round because you sold ten million

09:34

then that's very expensive capital. If you think it's gonna be worth a hundred million dollars someday or two hundred million dollars, you should raise that money later.

then that's very expensive capital. If you think it's gonna be worth a hundred million dollars someday or two hundred million dollars, you should raise that money later.

09:42

But you do need to get moving, and time is never on your side. You know, any good idea I've come up with Eventually, even at six months later, three other people are gonna come up with the same idea. So you need to move quickly. People tend to they most people understand the the risk of doing something.

But you do need to get moving, and time is never on your side. You know, any good idea I've come up with Eventually, even at six months later, three other people are gonna come up with the same idea. So you need to move quickly. People tend to they most people understand the the risk of doing something.

10:01

They understate the risk of not doing something. Can you tell us a story where moving fast, either benefited you or cost you big in one of these races that you ran? Absolutely. So double g is the perfect example. We expanded to twenty five countries before our first country was profitable.

They understate the risk of not doing something. Can you tell us a story where moving fast, either benefited you or cost you big in one of these races that you ran? Absolutely. So double g is the perfect example. We expanded to twenty five countries before our first country was profitable.

10:17

So if we were a big company, everyone would have said, look, let's wait and see and make sure our model works.

So if we were a big company, everyone would have said, look, let's wait and see and make sure our model works.

10:22

But the result was if you were Procter and Gamble or Caterpillar or IBM,

But the result was if you were Procter and Gamble or Caterpillar or IBM,

10:27

who did you work with? You worked with that. Because we had operations in twenty five countries, and you have off offices in those countries. You didn't work with our competitor who had offices in six countries.

who did you work with? You worked with that. Because we had operations in twenty five countries, and you have off offices in those countries. You didn't work with our competitor who had offices in six countries.

10:37

As a result,

As a result,

10:38

we swept the market. We lost a bunch of money, but we're able to fund it. And that is the reason today, twenty five years later, that, you know,

we swept the market. We lost a bunch of money, but we're able to fund it. And that is the reason today, twenty five years later, that, you know,

10:47

Google still has a commanding share. So we got it early on, and it's never been given up. But you're taking a chance. I mean, There are there are times when you invest in something and it it doesn't work that well. And you're like, wow. Who should have waited? You don't have time to wait.

Google still has a commanding share. So we got it early on, and it's never been given up. But you're taking a chance. I mean, There are there are times when you invest in something and it it doesn't work that well. And you're like, wow. Who should have waited? You don't have time to wait.

11:01

What insight

What insight

11:02

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 made. Off the DoubleClick sale. I I won't say it unless you wanna say it. But did you,

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 made. Off the DoubleClick sale. I I won't say it unless you wanna say it. But did you,

11:15

which I thought it was amazing that you told me this. I was like, damn, this guy's helping me out so much tell me all this information,

which I thought it was amazing that you told me this. I was like, damn, this guy's helping me out so much tell me all this information,

11:20

did you

did you

11:22

you and Dwight got together to start I don't know if you call it an incubator or what whatever you call Alley Corp, but did you

you and Dwight got together to start I don't know if you call it an incubator or what whatever you call Alley Corp, but did you

11:28

Was insider the first idea that you had and what led to that what led to the insight to start that? Yeah. So the insight idea was so simple that you can't even give us credit for it. So this is two thousand seven.

Was insider the first idea that you had and what led to that what led to the insight to start that? Yeah. So the insight idea was so simple that you can't even give us credit for it. So this is two thousand seven.

11:39

I love business publications and media publications. So I I'm sort of a compulsive reader of that, and I didn't have the publication I wanted. And it's so hard to to remember for people today that the Wall Street Journal and Business Week at the time did not basically, did not update their websites during the day. That's crazy. I was 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. Article have to be done late at night. And so at ten AM ten AM, no one's updating.

I love business publications and media publications. So I I'm sort of a compulsive reader of that, and I didn't have the publication I wanted. And it's so hard to to remember for people today that the Wall Street Journal and Business Week at the time did not basically, did not update their websites during the day. That's crazy. I was 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. Article have to be done late at night. And so at ten AM ten AM, no one's updating.

12:11

And so they just had not adapted and don't forget, you're really got mobile phones in two thousand eight.

And so they just had not adapted and don't forget, you're really got mobile phones in two thousand eight.

12:18

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.

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.

12:32

Writing stories that were not complete in a way. We'd hear a rumor that x company was buying a 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 this, yeah, actually, it's true.

Writing stories that were not complete in a way. We'd hear a rumor that x company was buying a 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 this, yeah, actually, it's true.

12:44

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, yeah, we'd write, so and so just overpaid for a company.

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, yeah, we'd write, so and so just overpaid for a company.

12:57

It's more important that we have a smart point of view than that we're right in the long term.

It's more important that we have a smart point of view than that we're right in the long term.

13:02

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. Nolan cared about headlines because if you had business week magazine, does the headline result in more revenue for you? No.

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. Nolan cared about headlines because if you had business week magazine, does the headline result in more revenue for you? No.

13:18

But when we, we would AB test three headlines very quickly on a story and realize what was working. And so you know, what I'm proud of is that business insider is at three hundred million unique today and never spent one dollar in advertising.

But when we, we would AB test three headlines very quickly on a story and realize what was working. And so you know, what I'm proud of is that business insider is at three hundred million unique today and never spent one dollar in advertising.

13:33

Yeah. You told me well, you said you you you said we were just we were gonna just churn out these articles, which

Yeah. You told me well, you said you you you said we were just we were gonna just churn out these articles, which

13:40

is common now, but you go

is common now, but you go

13:43

you had this really cool insight. You go it it's kind of like Honda in nineteen eighty five versus General Motors. Americans

you had this really cool insight. You go it it's kind of like Honda in nineteen eighty five versus General Motors. Americans

13:50

laughed at the Honda

laughed at the Honda

13:51

car. They said this is just too flimsy. This isn't good,

car. They said this is just too flimsy. This isn't good,

13:55

but they're gonna, like, cap some market share and they're going to improve. And you said it's kinda like that with business insider.

but they're gonna, like, cap some market share and they're going to improve. And you said it's kinda like that with business insider.

14:02

The the the quote, the critics or the the real people in the industry, whatever you wanna 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 something, but we got more traffic than Wall Street Journal. And now they're looking at us that, like, holy crap, you surpass us, and we could afford to have a more substantial journalism that maybe is taken more seriously if if that's even, something you care about. I I would guess by twenty fifteen, we had seven people covering military and defense.

The the the quote, the critics or the the real people in the industry, whatever you wanna 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 something, but we got more traffic than Wall Street Journal. And now they're looking at us that, like, holy crap, you surpass us, and we could afford to have a more substantial journalism that maybe is taken more seriously if if that's even, something you care about. I I would guess by twenty fifteen, we had seven people covering military and defense.

14:33

That's deep coverage.

That's deep coverage.

14:35

I mean, you you you have a lot. You're writing great 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 the product didn't get better over time. We started winning awards.

I mean, you you you have a lot. You're writing great 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 the product didn't get better over time. We started winning awards.

14:48

But it always was intended to be a different positioning. It was punchier.

But it always was intended to be a different positioning. It was punchier.

14:52

It appealed to younger people.

It appealed to younger people.

14:54

It was opinionated.

It was opinionated.

14:55

You know, it's just a different product.

You know, it's just a different product.

14:58

But I think I think the company, you know, we Henry Blodget who's still the CEO has done an extraordinary job in over fifteen years.

But I think I think the company, you know, we Henry Blodget who's still the CEO has done an extraordinary job in over fifteen years.

15:06

And a lot of these insights came from him. And he he was one of seven people. I interviewed for that job, and he killed it. What'd you see in him that, made you pick him I know, if you remember, it was a bold choice because Henry had had some issues on Wall Street.

And a lot of these insights came from him. And he he was one of seven people. I interviewed for that job, and he killed it. What'd you see in him that, made you pick him I know, if you remember, it was a bold choice because Henry had had some issues on Wall Street.

15:20

So you some people felt like he was tainted.

So you some people felt like he was tainted.

15:23

I knew that he And the the issues, by the way, were I think he got accused of was it insider trading? No. No. Not inside trading at all. What happened was At the time, what was standard there was that, 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

I knew that he And the the issues, by the way, were I think he got accused of was it insider trading? No. No. Not inside trading at all. What happened was At the time, what was standard there was that, 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

15:45

to their, their, their companies, their investors.

to their, their, their companies, their investors.

15:48

Everyone did that? Henry actually wrote

Everyone did that? Henry actually wrote

15:51

internal emails saying I feel really uncomfortable with this.

internal emails saying I feel really uncomfortable with this.

15:55

Which then was used against him. You know, no one else did that. And so legally, I don't think he did anything wrong.

Which then was used against him. You know, no one else did that. And so legally, I don't think he did anything wrong.

16:01

Everything he wrote was approved by his superiors and and order. But, anyway,

Everything he wrote was approved by his superiors and and order. But, anyway,

16:07

you know, some people felt like he was tainted. I didn't at all what I did know is he was an incredible writer. And he was a perceptive

you know, some people felt like he was tainted. I didn't at all what I did know is he was an incredible writer. And he was a perceptive

16:15

journalist. He was writing pieces for the Atlantic,

journalist. He was writing pieces for the Atlantic,

16:18

I mean, he's just so good. I mean, he's so talented. And he also he truly understood

I mean, he's just so good. I mean, he's so talented. And he also he truly understood

16:24

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.

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.

16:32

Henry, had was was fresh he had never really worked in a newsroom, which Kimbie viewed as a weakness. I viewed it as a strength. And so he changed the rules.

Henry, had was was fresh he had never really worked in a newsroom, which Kimbie viewed as a weakness. I viewed it as a strength. And so he changed the rules.

16:41

And we were willing to do that, and he did an incredible job. You know, that same strategy of kind of, like, start with the content quickly that gets traffic. Don't try to be don't look for kind of like the pure acclaim in the industry, look for what the market wants, and then over time improve the quality. That was also Buzzfeed's strategy.

And we were willing to do that, and he did an incredible job. You know, that same strategy of kind of, like, start with the content quickly that gets traffic. Don't try to be don't look for kind of like the pure acclaim in the industry, look for what the market wants, and then over time improve the quality. That was also Buzzfeed's strategy.

17:00

But today, I'm looking at the Buzzfeed stock. It's thirty six cents. It's a fifty million dollar market cap. What do you think they got wrong? What happened to Buzzfeed? Because it seemed like they were they had that whole that same playbook. And Jona Preddy, if you ever hear him talk, he seems like, you know, whip smart in the same way.

But today, I'm looking at the Buzzfeed stock. It's thirty six cents. It's a fifty million dollar market cap. What do you think they got wrong? What happened to Buzzfeed? Because it seemed like they were they had that whole that same playbook. And Jona Preddy, if you ever hear him talk, he seems like, you know, whip smart in the same way.

17:15

For me, it's very clear, and I've I felt this from day one, even when they were theoretically worth two billion dollars.

For me, it's very clear, and I've I felt this from day one, even when they were theoretically worth two billion dollars.

17:21

I rarely ran into someone who said, I love reading Buzzfeed every day. I I don't believe they built up a true brain.

I rarely ran into someone who said, I love reading Buzzfeed every day. I I don't believe they built up a true brain.

17:30

They showed up in search results. They got traffic,

They showed up in search results. They got traffic,

17:33

but there were, you know, many, many people that religiously read business insider every single day. So it it just had a brand that I think was much stronger and more defined.

but there were, you know, many, many people that religiously read business insider every single day. So it it just had a brand that I think was much stronger and more defined.

17:44

And you you you guys have another

And you you you guys have another

17:47

funny part about you, which is I was telling my wife this because we were talk I was telling her I was gonna talk to you and I was gonna and and I followed Dave Portnoy on on Twitter from Barstool.

funny part about you, which is I was telling my wife this because we were talk I was telling her I was gonna talk to you and I was gonna and and I followed Dave Portnoy on on Twitter from Barstool.

17:57

Business insider is the only one to get one up on him. So you guys had this you guys had this article

Business insider is the only one to get one up on him. So you guys had this you guys had this article

18:04

about some some stuff that he had done

about some some stuff that he had done

18:06

and he went apeshit and he went crazy. Yep. And business insider had the best response, which was no response. You guys didn't reply to anything. And it's the only time I've ever seen Day Portnoy get one up. I wasn't really involved with that whole exchange that happened after

and he went apeshit and he went crazy. Yep. And business insider had the best response, which was no response. You guys didn't reply to anything. And it's the only time I've ever seen Day Portnoy get one up. I wasn't really involved with that whole exchange that happened after

18:24

I we sold the company. So Well, I thought it was pretty funny. And I,

I we sold the company. So Well, I thought it was pretty funny. And I,

18:29

I thought it was I thought the systems that are actually handled it wonderfully. And they were the first people that I've saw that got one over onto him. You know, you know, Kevin,

I thought it was I thought the systems that are actually handled it wonderfully. And they were the first people that I've saw that got one over onto him. You know, you know, Kevin,

18:39

you you guys have had so many hits come out of the studio. And,

you you guys have had so many hits come out of the studio. And,

18:44

as somebody who ran a studio for six years and, did not have billion dollar hits come out of it.

as somebody who ran a studio for six years and, did not have billion dollar hits come out of it.

18:50

I gotta know. What's the, 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 probably seen the same results that I have, which is that very, very few

I gotta know. What's the, 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 probably seen the same results that I have, which is that very, very few

19:02

come up with anything that works. What do you think you guys did differently than others? So it's not that, you know, detail wise or 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.

come up with anything that works. What do you think you guys did differently than others? So it's not that, you know, detail wise or 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.

19:17

So that's just there's nothing else.

So that's just there's nothing else.

19:20

So,

So,

19:21

you know, we've had some good ideas.

you know, we've had some good ideas.

19:23

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 fifty 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 fifty 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.

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 fifty 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 fifty 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.

19:43

But again, it's a little bit like watching, you know, I 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 who have a lot of experience doing this. It's just a series of judgment calls. You know, I think

But again, it's a little bit like watching, you know, I 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 who have a lot of experience doing this. It's just a series of judgment calls. You know, I think

20:01

I'm able because of the track record able to convince some good people to be CEOs.

I'm able because of the track record able to convince some good people to be CEOs.

20:06

That's important too. And we, you know, we spend a lot of time helping them. So I chair twelve companies.

That's important too. And we, you know, we spend a lot of time helping them. So I chair twelve companies.

20:11

So about half of my time is spent focusing on those twelve, which are twelve of our most valuable companies.

So about half of my time is spent focusing on those twelve, which are twelve of our most valuable companies.

20:16

To really guide them and make sure that they do as well as possible. Walk us through, like, one of those ideas. So Okay. So here for example, two and a half years ago. So I

To really guide them and make sure that they do as well as possible. Walk us through, like, one of those ideas. So Okay. So here for example, two and a half years ago. So I

20:26

I'm very interested in psychedelics

I'm very interested in psychedelics

20:29

or mental health. I'm the leading funder of the Yale Center for Cyclic Research. You know, I'm involved with a bunch of things

or mental health. I'm the leading funder of the Yale Center for Cyclic Research. You know, I'm involved with a bunch of things

20:36

in non profit research for, you know, pushing psychedelics for forward so they can be legalized either by by the FDA or by state.

in non profit research for, you know, pushing psychedelics for forward so they can be legalized either by by the FDA or by state.

20:45

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. The person my team works with me interviews, fifty people. Yeah. We're talking to everyone. And we come up with a solution that was partly influenced by some of the work that had been done at Yale And we started a company called Transcend.

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. The person my team works with me interviews, fifty people. Yeah. We're talking to everyone. And we come up with a solution that was partly influenced by some of the work that had been done at Yale And we started a company called Transcend.

21:03

The person on my team, actually, which is unusual, spins out to become the CEO.

The person on my team, actually, which is unusual, spins out to become the CEO.

21:08

Blake Mandell,

Blake Mandell,

21:09

Big article in,

Big article in,

21:11

the Wall Street Journal about five months ago about transcend

the Wall Street Journal about five months ago about transcend

21:14

because we we start off with a million and a half dollars. But we raised forty million dollars about a year to a year and a half later in two tranches at eighty million free

because we we start off with a million and a half dollars. But we raised forty million dollars about a year to a year and a half later in two tranches at eighty million free

21:25

So big, big, big, big step up, big valuation.

So big, big, big, big step up, big valuation.

21:28

And we have a compound that you haven't heard of going through the FDA process that's in phase two trials right now.

And we have a compound that you haven't heard of going through the FDA process that's in phase two trials right now.

21:35

And so people are obviously optimistic about the future, like the team, like the execution.

And so people are obviously optimistic about the future, like the team, like the execution.

21:40

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

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

21:48

or mushrooms because those have been around for a long time, but we actually did get a patent for meth alone,

or mushrooms because those have been around for a long time, but we actually did get a patent for meth alone,

21:53

which is the compound that we're working on.

which is the compound that we're working on.

21:56

So so far, so good. Now there's still risk, but that company is, you know, we currently have a fifty million dollar position

So so far, so good. Now there's still risk, but that company is, you know, we currently have a fifty million dollar position

22:02

based on our five million that we've invested so far. And we think it has a lot of potential.

based on our five million that we've invested so far. And we think it has a lot of potential.

22:07

What about, like, with MongoDB. So

What about, like, with MongoDB. So

22:10

that was started. I think in two thousand seven, so Ali Corp was, like, a little bit early. Yeah. Did you have a team helping you research ideas back then? I didn't. That was purely Dwight,

that was started. I think in two thousand seven, so Ali Corp was, like, a little bit early. Yeah. Did you have a team helping you research ideas back then? I didn't. That was purely Dwight,

22:21

myself,

myself,

22:22

and Elliot Horowitz,

and Elliot Horowitz,

22:23

who was the most brilliant young engineer at DoubleClick. Out of seven hundred engineers, if you could pick out one person, other than Dwight, you would have picked him. And so we started a company together in two thousand five called Shop Whitkey, which is a search engine for shopping.

who was the most brilliant young engineer at DoubleClick. Out of seven hundred engineers, if you could pick out one person, other than Dwight, you would have picked him. And so we started a company together in two thousand five called Shop Whitkey, which is a search engine for shopping.

22:38

Did okay. Not great. We sold it in two thousand seven. Made a little bit of money. And then said, what are we gonna do next? And so I came up with this idea,

Did okay. Not great. We sold it in two thousand seven. Made a little bit of money. And then said, what are we gonna do next? And so I came up with this idea,

22:46

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.

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.

22:55

So not easy to keep funding going back to DCs with zero revenue.

So not easy to keep funding going back to DCs with zero revenue.

23:00

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 two thousand nine, two thousand ten, was not a good time to be raising with no revenues.

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 two thousand nine, two thousand ten, was not a good time to be raising with no revenues.

23:13

Then finally Sequoia came in, and then we raised a lot of money. And now it does

Then finally Sequoia came in, and then we raised a lot of money. And now it does

23:18

getting close to a two billion dollar run rate. Did that company make you a billionaire?

getting close to a two billion dollar run rate. Did that company make you a billionaire?

23:23

So, yeah, I mean, look, for all of us, it definitely,

So, yeah, I mean, look, for all of us, it definitely,

23:26

yeah, we all made lots of money on that on that company. Definitely. Those three years with no revenue,

yeah, we all made lots of money on that on that company. Definitely. Those three years with no revenue,

23:32

at the time where you, like, people just don't understand that this thing is, like, Others don't see it, but I see it, or where you're, 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 you know, let's keep going. No. No. I would say that all of us were nervous

at the time where you, like, people just don't understand that this thing is, like, Others don't see it, but I see it, or where you're, 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 you know, let's keep going. No. No. I would say that all of us were nervous

23:47

because, you know, you like to have revenue when you're gonna run out of money at some point. What helped us on the inside was that, the utilization, the number of really using the product was free,

because, you know, you like to have revenue when you're gonna run out of money at some point. What helped us on the inside was that, the utilization, the number of really using the product was free,

23:58

was growing every single month. All over the world. So there's, you know, probably fifty thousand small companies using the product. And so, you know, there were

was growing every single month. All over the world. So there's, you know, probably fifty thousand small companies using the product. And so, you know, there were

24:06

hundreds of meetups about Mongo and people were showing up. And we can see in a way that the dogs liked the dog food.

hundreds of meetups about Mongo and people were showing up. And we can see in a way that the dogs liked the dog food.

24:14

We just needed to then make it good enough that larger companies would pay money

We just needed to then make it good enough that larger companies would pay money

24:19

for it. And now we got there and and the rest is history.

for it. And now we got there and and the rest is history.

24:22

But what's crazy is, like, alright, business insider, I understand that well. That's media. I get it perfectly.

But what's crazy is, like, alright, business insider, I understand that well. That's media. I get it perfectly.

24:28

Gil, that's commerce. That's fairly easy to understand.

Gil, that's commerce. That's fairly easy to understand.

24:32

Zola,

Zola,

24:33

kind of media ish related, but, like, I feel like, I understand that business.

kind of media ish related, but, like, I feel like, I understand that business.

24:37

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 I don't 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.

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 I don't 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.

24:49

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 Elliot?

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 Elliot?

24:58

So Elliott and Dwight, you know, were the brains and the technical jobs. Like, the product could not have been built without them.

So Elliott and Dwight, you know, were the brains and the technical jobs. Like, the product could not have been built without them.

25:06

Annie 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 the 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, stop built for that. But, of course, data was moving that way. YouTube came out in two thousand five. Video is gonna be enormous.

Annie 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 the 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, stop built for that. But, of course, data was moving that way. YouTube came out in two thousand five. Video is gonna be enormous.

25:35

So I knew that trend was happening. I knew that the Oracle product was extraordinarily expensive.

So I knew that trend was happening. I knew that the Oracle product was extraordinarily expensive.

25:40

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.

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.

25:51

And so we thought collectively that we needed an open source database

And so we thought collectively that we needed an open source database

25:56

that, was was structured for the future. And so that was the bet. So with that, I understand. If you said five levels down, do I understand the code? No. But, you know, I was worried you could anytime you start a company, you know, like, I'm not a particularly good writer. Henry is,

that, was was structured for the future. And so that was the bet. So with that, I understand. If you said five levels down, do I understand the code? No. But, you know, I was worried you could anytime you start a company, you know, like, I'm not a particularly good writer. Henry is,

26:12

and he was in charge of that product. I knew the market well enough in both cases,

and he was in charge of that product. I knew the market well enough in both cases,

26:16

high level.

high level.

26:17

And then it's about assembling the team. You gotta think of yourself as you are the coach.

And then it's about assembling the team. You gotta think of yourself as you are the coach.

26:22

You are not the player.

You are not the player.

26:24

And if you were a coach and if you managed 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. You,

And if you were a coach and if you managed 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. You,

26:34

you've, like, with the when you're talking about transcend,

you've, like, with the when you're talking about transcend,

26:36

and you're like, we're we've got a drug going through FDA trials. I had the same reaction that 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 you're like, we're we've got a drug going through FDA trials. I had the same reaction that 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.

26:47

And,

And,

26:48

with with probably a whole bunch of, like, new things you gotta learn,

with with probably a whole bunch of, like, new things you gotta learn,

26:51

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,

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,

26:58

do you feel like 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 there 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. 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 over again, we also have, you know, I have seventy engineers

do you feel like 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 there 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. 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 over again, we also have, you know, I have seventy engineers

27:25

who work from me. I have my own in house outsource engineering company, which helps us build product now very quickly, which we've had the last three years.

who work from me. I have my own in house outsource engineering company, which helps us build product now very quickly, which we've had the last three years.

27:33

I own a big chunk of a search firm, ten person executive search firm that we set up so that we can get some of the best talent working for us, finding CEOs.

I own a big chunk of a search firm, ten person executive search firm that we set up so that we can get some of the best talent working for us, finding CEOs.

27:44

So we build infrastructure around it, but still most of it goes back to a good idea

So we build infrastructure around it, but still most of it goes back to a good idea

27:49

and,

and,

27:50

a good tee. And when we get that right, yes. And by the way, last one on on psych hills, yeah, 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.

a good tee. And when we get that right, yes. And by the way, last one on on psych hills, yeah, 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.

28:04

And then look, are 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.

And then look, are 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.

28:16

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. Psychedels is a ten year trend. MongoDB was a ten year trend.

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. Psychedels is a ten year trend. MongoDB was a ten year trend.

28:26

These are the things we are betting on. What are you consuming on a daily basis to spot these trends? Yeah. So

These are the things we are betting on. What are you consuming on a daily basis to spot these trends? Yeah. So

28:32

tons of things. No one thing. I'm on, you know, many, many

tons of things. No one thing. I'm on, you know, many, many

28:36

newsletters that are industry focused or general focused or science or 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.

newsletters that are industry focused or general focused or science or 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.

28:48

And then people in my team are more specialized than I am. So, you know, I have two MD MBAs

And then people in my team are more specialized than I am. So, you know, I have two MD MBAs

28:53

who are head up our health care practice

who are head up our health care practice

28:56

and then people below them that have worked in health care. So they were thinking of very specific issues that I probably wouldn't wouldn't think of.

and then people below them that have worked in health care. So they were thinking of very specific issues that I probably wouldn't wouldn't think of.

29:03

And the same is drive a person on marketplaces, a person on semiconductors

And the same is drive a person on marketplaces, a person on semiconductors

29:07

and material science, and a person on developer tools and enterprise software and two people on social impact.

and material science, and a person on developer tools and enterprise software and two people on social impact.

29:13

So a lot of what we do is in those areas, and I'm bigger and bigger believer now of industry focus.

So a lot of what we do is in those areas, and I'm bigger and bigger believer now of industry focus.

29:20

You know, it's a you 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

You know, it's a you 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

29:28

and interviewed a hundred people, you'd probably come up with some ideas that make sense. And the industries that you care about right now are health, health care.

and interviewed a hundred people, you'd probably come up with some ideas that make sense. And the industries that you care about right now are health, health care.

29:37

Definitely, then the ones I mentioned. So semiconductors

Definitely, then the ones I mentioned. So semiconductors

29:40

and material science,

and material science,

29:41

developer tools,

developer tools,

29:43

with some security,

with some security,

29:45

marketplaces,

marketplaces,

29:46

b to b marketplaces,

b to b marketplaces,

29:48

social impact, and robotics and automation.

social impact, and robotics and automation.

29:51

What's an example of a b to b marketplace?

What's an example of a b to b marketplace?

29:53

That you're interested in. Yeah. So we invest we have done a deep dive into the maritime industry.

That you're interested in. Yeah. So we invest we have done a deep dive into the maritime industry.

30:00

So shipping, no one thinks about it. Multi hundred billion dollars. Very behind in technology.

So shipping, no one thinks about it. Multi hundred billion dollars. Very behind in technology.

30:07

We invested in a company called BoxHub.

We invested in a company called BoxHub.

30:09

That's a marketplace for those containers.

That's a marketplace for those containers.

30:12

That are on container ships.

That are on container ships.

30:13

Based in Toronto,

Based in Toronto,

30:15

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

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

30:23

marketplace.

marketplace.

30:24

So you're a ship, let's say you're arriving in Cartagena.

So you're a ship, let's say you're arriving in Cartagena.

30:27

Your boiler

Your boiler

30:28

breaks.

breaks.

30:29

What are you gonna do? Now you weren't you weren't planning on that. And so having a site you can go to that becomes, like, sort of, the Amazon of that and as delivery and can get you those parts.

What are you gonna do? Now you weren't you weren't planning on that. And so having a site you can go to that becomes, like, sort of, the Amazon of that and as delivery and can get you those parts.

30:40

Everyone in the industry told us that that's needed. So we're literally just built a team two months ago, there are probably four people right now, and so we're off and running. What's that company called? It's it doesn't have its official name yet.

Everyone in the industry told us that that's needed. So we're literally just built a team two months ago, there are probably four people right now, and so we're off and running. What's that company called? It's it doesn't have its official name yet.

30:53

So, alright, let's use that as an example. Yeah. So you basically did,

So, alright, let's use that as an example. Yeah. So you basically did,

30:57

did you just go and somehow network your way into talking to fifty yeah. So a woman on my team,

did you just go and somehow network your way into talking to fifty yeah. So a woman on my team,

31:04

absolutely did that and went to two,

absolutely did that and went to two,

31:07

maritime conferences.

maritime conferences.

31:09

So which she said were fascinating.

So which she said were fascinating.

31:12

It's basically people from Venezuela,

It's basically people from Venezuela,

31:14

you know, the Middle East, Russia,

you know, the Middle East, Russia,

31:16

you know, from all over the world, Greek, And so I'm trying to understand the history. Just just about the pirates, but the pirates, but hobble hobble hobble it around and a bunch of parrots and bird shit all over the place. She said it did not look like her Princeton reunion

you know, from all over the world, Greek, And so I'm trying to understand the history. Just just about the pirates, but the pirates, but hobble hobble hobble it around and a bunch of parrots and bird shit all over the place. She said it did not look like her Princeton reunion

31:29

at all.

at all.

31:32

So yeah. And so and she met with the couple investors who invest in this space, you know, ship owners,

So yeah. And so and she met with the couple investors who invest in this space, you know, ship owners,

31:38

data providers, everyone. You're just trying to understand how does the industry work And I think there's an advantage sometimes coming from outside.

data providers, everyone. You're just trying to understand how does the industry work And I think there's an advantage sometimes coming from outside.

31:46

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. Right. And that's why, like, you know, Henry was the perfect person 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. Right. And that's why, like, you know, Henry was the perfect person coming from outside.

31:59

You know, when I started guilt,

You know, when I started guilt,

32:01

none of my initial five people had worked in the fashion industry,

none of my initial five people had worked in the fashion industry,

32:05

but we understood the problem. It wasn't that complicated. So we could create something that was that was interesting and unusual.

but we understood the problem. It wasn't that complicated. So we could create something that was that was interesting and unusual.

32:12

So that's the right approach. We just started a company in assisted fertility. So I'm sure you guys know you have friends, you know, who are getting IVF?

So that's the right approach. We just started a company in assisted fertility. So I'm sure you guys know you have friends, you know, who are getting IVF?

32:20

I did it. Yeah. My my brother and his husband, you know, had a child through surrogacy,

I did it. Yeah. My my brother and his husband, you know, had a child through surrogacy,

32:27

freezing eggs, that's gonna grow for the next ten years. For all the reasons we know about, people having children later, sperm counts are down, bunch of things. So we do we start we started a company, but, 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.

freezing eggs, that's gonna grow for the next ten years. For all the reasons we know about, people having children later, sperm counts are down, bunch of things. So we do we start we started a company, but, 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.

32:46

A lot of people wanted to do it. People are excited about the team.

A lot of people wanted to do it. People are excited about the team.

32:49

You know,

You know,

32:50

good set of people,

good set of people,

32:52

mostly from Stanford Business School on this team, and it's a big space.

mostly from Stanford Business School on this team, and it's a big space.

32:56

So,

So,

32:57

I'm I'm gonna bet on that team and that trend for a while.

I'm I'm gonna bet on that team and that trend for a while.

33:01

What does that deck look like? You said they they do like a or maybe I think a fifty page memo or deck. I'm not sure what you said. Do you have a structure for it? Yeah. It's generally one just talking about the industry, where are the problems, where are the pain points,

What does that deck look like? You said they they do like a or maybe I think a fifty page memo or deck. I'm not sure what you said. Do you have a structure for it? Yeah. It's generally one just talking about the industry, where are the problems, where are the pain points,

33:13

and then where are the opportunities? What's the product idea? One of the reasons I do almost nothing in e commerce these days is because I don't see the problem.

and then where are the opportunities? What's the product idea? One of the reasons I do almost nothing in e commerce these days is because I don't see the problem.

33:23

We solve the industry solve the problem. I mean, If you need anything on the planet Earth, just about, you know, you can find a site. They'll have ten thousand of them. It'll be sent to your house by tomorrow.

We solve the industry solve the problem. I mean, If you need anything on the planet Earth, just about, you know, you can find a site. They'll have ten thousand of them. It'll be sent to your house by tomorrow.

33:33

Man, I don't know how to do better. That problem is solved.

Man, I don't know how to do better. That problem is solved.

33:37

Whereas, when I, you know, when I started guilt, you actually couldn't get Mark Jacobs at fifty percent off online,

Whereas, when I, you know, when I started guilt, you actually couldn't get Mark Jacobs at fifty percent off online,

33:44

just no one offered it. And so we offered it, and people went crazy over that.

just no one offered it. And so we offered it, and people went crazy over that.

33:49

So e commerce is very mature. Frankly, media is pretty mature right now. There's a lot, you know, not that many people say to me, I just can't find what I wanna wanna read.

So e commerce is very mature. Frankly, media is pretty mature right now. There's a lot, you know, not that many people say to me, I just can't find what I wanna wanna read.

33:58

But even, you know, once in a while, we're working on one idea right now, the early stages in the media space,

But even, you know, once in a while, we're working on one idea right now, the early stages in the media space,

34:03

but not not sure yet.

but not not sure yet.

34:05

So we're looking for problems. The health one of the reason I like health care

So we're looking for problems. The health one of the reason I like health care

34:09

is because

is because

34:10

it health care is not solved.

it health care is not solved.

34:12

You know, as you guys know, you know, you have knee surgery.

You know, as you guys know, you know, you have knee surgery.

34:16

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 forty thousand. Yet in France, it's twenty thousand, and the results are better.

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 forty thousand. Yet in France, it's twenty thousand, and the results are better.

34:27

So can it be done better? Yes. It can be done better. New twenty times more black women die in childbirth

So can it be done better? Yes. It can be done better. New twenty times more black women die in childbirth

34:34

than in Sweden? Yes.

than in Sweden? Yes.

34:36

Is that something that is just inherited is always gonna happen? No. We don't do enough prevention. There are many structural issues in health care that have not been solved, and we're we're solving some of

Is that something that is just inherited is always gonna happen? No. We don't do enough prevention. There are many structural issues in health care that have not been solved, and we're we're solving some of

34:50

Our software is the worst. Have you heard of HubSpot?

Our software is the worst. Have you heard of HubSpot?

34:53

See, most CRMs are a cobbled together mess, but HubSpot easy to adopt and actually looks gorgeous. I think I love our new CRM. Our software is the best. HubSpot,

See, most CRMs are a cobbled together mess, but HubSpot easy to adopt and actually looks gorgeous. I think I love our new CRM. Our software is the best. HubSpot,

35:03

grow better.

grow better.

35:05

It sounds to me, like, what you do is you look think about what's the world gonna look like in ten years.

It sounds to me, like, what you do is you look think about what's the world gonna look like in ten years.

35:10

You know, either what's a problem that just if somebody could solve it, that would be a major major unlock or, hey, the the puck is going this way.

You know, either what's a problem that just if somebody could solve it, that would be a major major unlock or, hey, the the puck is going this way.

35:17

And then then it sounds like you say,

And then then it sounds like you say,

35:20

Cool. Let's go find out everything we can learn about that space. We we go in kind of, open minded about what problem we're gonna solve. We try to figure out, where all the pain points are. And then it sounds like you're looking for what I'll call the big obvious problem.

Cool. Let's go find out everything we can learn about that space. We we go in kind of, open minded about what problem we're gonna solve. We try to figure out, where all the pain points are. And then it sounds like you're looking for what I'll call the big obvious problem.

35:35

Which is

Which is

35:36

if it's too complicated and nuanced, it doesn't sound like you're that interested. It's like,

if it's too complicated and nuanced, it doesn't sound like you're that interested. It's like,

35:41

hey, you can't find luxury fashion online for fifty percent off. Right? Okay. That's like a big obvious problem. It doesn't take that much explaining or expertise to even understand the problem. Maybe the solution might be might take some expertise but the problem should be in your face.

hey, you can't find luxury fashion online for fifty percent off. Right? Okay. That's like a big obvious problem. It doesn't take that much explaining or expertise to even understand the problem. Maybe the solution might be might take some expertise but the problem should be in your face.

35:55

Once once you're looking in that industry.

Once once you're looking in that industry.

35:59

We,

We,

36:00

we have this thing we say on the podcast, which is that there are businesses that that there are business plans that are what I call one chart businesses. You could just look at one chart, and it just tells you, oh, that's Yep. That's so obvious. Like, we were looking at one that was around,

we have this thing we say on the podcast, which is that there are businesses that that there are business plans that are what I call one chart businesses. You could just look at one chart, and it just tells you, oh, that's Yep. That's so obvious. Like, we were looking at one that was around,

36:14

in the death space, around cremation. It was like cremation went from, I don't know, seven percent of all things to, like, fifty percent. It's now the majority of,

in the death space, around cremation. It was like cremation went from, I don't know, seven percent of all things to, like, fifty percent. It's now the majority of,

36:23

of of of of what choices people make when

of of of of what choices people make when

36:26

when it comes to a funeral.

when it comes to a funeral.

36:28

And this is, like, that's a one chart business. You can look at nothing else and say, alright. I know there's I know there's opportunity when I look at a chart like this.

And this is, like, that's a one chart business. You can look at nothing else and say, alright. I know there's I know there's opportunity when I look at a chart like this.

36:35

Is is is that does that jive with your way of thinking, or do you have any anything you could add to to our understanding of that? No. Absolutely. I mean, I'll give you another one. The cost of labor

Is is is that does that jive with your way of thinking, or do you have any anything you could add to to our understanding of that? No. Absolutely. I mean, I'll give you another one. The cost of labor

36:45

is gonna just keep going up. And so, you know, waiters were paid fifteen dollars an hour. Now it's twenty to twenty five dollars an hour in New York, unless we change immigration or something fundamentally change, is that could be thirty dollars an hour. So you know what? Over time, that changes the calculus of automation,

is gonna just keep going up. And so, you know, waiters were paid fifteen dollars an hour. Now it's twenty to twenty five dollars an hour in New York, unless we change immigration or something fundamentally change, is that could be thirty dollars an hour. So you know what? Over time, that changes the calculus of automation,

37:03

whether it's making French fries, whether it's through this, you know, we're all gonna have to find ways to use less labor.

whether it's making French fries, whether it's through this, you know, we're all gonna have to find ways to use less labor.

37:09

And so when cost of tech goes down and the cost of labor goes up, what does that tell you? More automation is gonna happen.

And so when cost of tech goes down and the cost of labor goes up, what does that tell you? More automation is gonna happen.

37:16

It's all bet on that trend all day long. Now we're an investor in a company that gives robotic massages. There's seventeen thousand

It's all bet on that trend all day long. Now we're an investor in a company that gives robotic massages. There's seventeen thousand

37:24

open positions for massage therapists in this country.

open positions for massage therapists in this country.

37:28

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 that's just one example, but I have ten others.

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 that's just one example, but I have ten others.

37:39

We,

We,

37:40

Well, what are those ten others? Of just of just automation or or other idea? No. Just I'll give you one other example. Another company we invested in is, so driverless cars is, as you know, not legal in most countries, in most states.

Well, what are those ten others? Of just of just automation or or other idea? No. Just I'll give you one other example. Another company we invested in is, so driverless cars is, as you know, not legal in most countries, in most states.

37:53

But having a remote driver is

But having a remote driver is

37:56

So would you if you're in New York City, would you pay money to have a car

So would you if you're in New York City, would you pay money to have a car

38:01

a a rental car brought to your apartment? As opposed to you having to take your seven suitcases and two kids and go to the rental car. Of course, you would.

a a rental car brought to your apartment? As opposed to you having to take your seven suitcases and two kids and go to the rental car. Of course, you would.

38:10

And yet we can have someone in the Philippines or in you know, Arizona

And yet we can have someone in the Philippines or in you know, Arizona

38:14

drives the car because we put software and hardware in the in the car, they can see everything that's legal in many states.

drives the car because we put software and hardware in the in the car, they can see everything that's legal in many states.

38:21

Airports are already talking to us,

Airports are already talking to us,

38:24

about,

about,

38:25

the vans that they have to drive around to bring people to the rental car lots at two in the morning. Hardly anyone on there. You gotta pay someone double time, forty bucks an hour. That should be done by someone remotely.

the vans that they have to drive around to bring people to the rental car lots at two in the morning. Hardly anyone on there. You gotta pay someone double time, forty bucks an hour. That should be done by someone remotely.

38:37

So things like that are gonna be automated.

So things like that are gonna be automated.

38:40

So Sean and I,

So Sean and I,

38:42

we've had a bunch of cool people on this podcast. So one of our great friends is this guy named Andrew Wilkinson. He owns maybe forty companies a lot of agencies and and web stuff,

we've had a bunch of cool people on this podcast. So one of our great friends is this guy named Andrew Wilkinson. He owns maybe forty companies a lot of agencies and and web stuff,

38:51

mostly bootstrapped. It's publicly traded now. And then we had this other guy named Saeed, who's, like, thirty two years old who owns,

mostly bootstrapped. It's publicly traded now. And then we had this other guy named Saeed, who's, like, thirty two years old who owns,

38:59

a bunch of WordPress plugins, basically, that It's the bootstrapped to Unicorn.

a bunch of WordPress plugins, basically, that It's the bootstrapped to Unicorn.

39:03

Wow. Amazing. And, well, what she owns most of And so we we have a lot of, like and and and I fall in this category as well. I I bootstrap a lot of my things.

Wow. Amazing. And, well, what she owns most of And so we we have a lot of, like and and and I fall in this category as well. I I bootstrap a lot of my things.

39:13

And then there's this other category. So there's category of people who, like, bootstrap stuff and the sheets are cash flow. And then oftentimes that same group of people prefer to go and buy companies as opposed to to build them from scratch, you're taking the opposite approach a little bit where you're, like, I'm gonna fund it. It's not gonna make money at first, but I and I might go and raise a a a shit ton more money, but this might be a huge idea, and I'll own a small piece of it.

And then there's this other category. So there's category of people who, like, bootstrap stuff and the sheets are cash flow. And then oftentimes that same group of people prefer to go and buy companies as opposed to to build them from scratch, you're taking the opposite approach a little bit where you're, like, I'm gonna fund it. It's not gonna make money at first, but I and I might go and raise a a a shit ton more money, but this might be a huge idea, and I'll own a small piece of it.

39:39

What, 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 versus build kind of mindset? Yeah. So it really depends on the type of business. So if you're running an agency,

What, 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 versus build kind of mindset? Yeah. So it really depends on the type of business. So if you're running an agency,

39:52

You just don't need a lot of capital. You know, you hire

You just don't need a lot of capital. You know, you hire

39:55

five people who, and then

five people who, and then

39:58

they that agencies make money, and then you use that money to reinvest in growth.

they that agencies make money, and then you use that money to reinvest in growth.

40:02

If you're building what I'm building is closer to like a hotel,

If you're building what I'm building is closer to like a hotel,

40:05

you know, you have to build the whole building before anyone comes and stays with you. So little different because, like, Mongo, you gotta take years to build a good enough product. And there's no way to bootstrap that. You know, it takes

you know, you have to build the whole building before anyone comes and stays with you. So little different because, like, Mongo, you gotta take years to build a good enough product. And there's no way to bootstrap that. You know, it takes

40:18

twenty, fifty, you know, there's a hundred million dollars generally for those types of companies

twenty, fifty, you know, there's a hundred million dollars generally for those types of companies

40:23

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 those. For example, the the agency that that I have, I said those engineers. I just have an outsourced engineering company. I own all of that,

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 those. For example, the the agency that that I have, I said those engineers. I just have an outsourced engineering company. I own all of that,

40:38

because it has clients and it bills as it gets more clients.

because it has clients and it bills as it gets more clients.

40:42

But those businesses are not a scalable profit margins are generally lower.

But those businesses are not a scalable profit margins are generally lower.

40:47

Those other knots had missed, I generally go after.

Those other knots had missed, I generally go after.

40:50

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 I mean, what what's the motivation? I just prefer creating a product, a real product that's hard,

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 I mean, what what's the motivation? I just prefer creating a product, a real product that's hard,

41:01

and then, you know, making more scalable and building it up over time. The vast majority of quite successful companies are in that category.

and then, you know, making more scalable and building it up over time. The vast majority of quite successful companies are in that category.

41:09

The services oriented companies, you know, it's harder it's harder to get to be a corn. It can happen, but there aren't there aren't that many. You over time got more selective on the project selection because I look at, you know, you did business insider. I think you were the see were you the CEO for, like, a a period of time there? Nine years. Is that right? No. No. I was the chairman for all nine years.

The services oriented companies, you know, it's harder it's harder to get to be a corn. It can happen, but there aren't there aren't that many. You over time got more selective on the project selection because I look at, you know, you did business insider. I think you were the see were you the CEO for, like, a a period of time there? Nine years. Is that right? No. No. I was the chairman for all nine years.

41:29

I did step in I did step in to be the CEO of guilt when we were growing really quickly. I just 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 fifteen years.

I did step in I did step in to be the CEO of guilt when we were growing really quickly. I just 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 fifteen years.

41:42

I stepped into Mongo. I changed CEOs about eight years ago.

I stepped into Mongo. I changed CEOs about eight years ago.

41:47

And for three months, I was de facto the CEO as I was doing it. So you've you've run these for a period of time, but mostly not. But but I guess,

And for three months, I was de facto the CEO as I was doing it. So you've you've run these for a period of time, but mostly not. But but I guess,

41:54

I think about businesses, I look at my career, and it's like, I look back and I think, okay. I have these ten things I did.

I think about businesses, I look at my career, and it's like, I look back and I think, okay. I have these ten things I did.

42:00

Two of them, were, like, ate up all of my time and gave me a bunch of gray hair for, like, relatively less payoff

Two of them, were, like, ate up all of my time and gave me a bunch of gray hair for, like, relatively less payoff

42:08

versus these other two, which was, like, I just kinda wrote the check. It was a obvious opportunity,

versus these other two, which was, like, I just kinda wrote the check. It was a obvious opportunity,

42:12

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

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

42:20

combination of the value, the pain that it took to get there, you know, all all of that. And then

combination of the value, the pain that it took to get there, you know, all all of that. And then

42:25

do you have a framework around there, or do you think it's just luck of the draw? I think it's like 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.

do you have a framework around there, or do you think it's just luck of the draw? I think it's like 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.

42:38

So, you know, chairman for thirteen years,

So, you know, chairman for thirteen years,

42:41

and yet it's a super valuable and, you know, fascinating company that's gonna be around for the next fifty years.

and yet it's a super valuable and, you know, fascinating company that's gonna be around for the next fifty years.

42:48

But, you know, I I'm intellectually curious. 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,

But, you know, I I'm intellectually curious. 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,

42:58

and I have to try and keep up and learn something about these.

and I have to try and keep up and learn something about these.

43:02

And that's what's so, you know, we have one in cardiology

And that's what's so, you know, we have one in cardiology

43:05

There's so many different things. It's that's what's amazing. And for someone who's thinking about ten years, I'm

There's so many different things. It's that's what's amazing. And for someone who's thinking about ten years, I'm

43:12

a little surprised. I don't see AI all over this doc. You know, you're not saying, aye aye aye aye. Yeah. It sounds like it might be embedded in some of these things that you're doing. Like, might be a tool you use, but Are you

a little surprised. I don't see AI all over this doc. You know, you're not saying, aye aye aye aye. Yeah. It sounds like it might be embedded in some of these things that you're doing. Like, might be a tool you use, but Are you

43:22

bearish on it for some reason, or what's your thinking around AI?

bearish on it for some reason, or what's your thinking around AI?

43:26

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.

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.

43:33

Now three people walk in and say, we're worth a hundred million dollars because we're gonna put together an AI company. Just didn't make sense. So we didn't make any direct investments there.

Now three people walk in and say, we're worth a hundred million dollars because we're gonna put together an AI company. Just didn't make sense. So we didn't make any direct investments there.

43:42

Each we're really encouraging each one of our companies to use

Each we're really encouraging each one of our companies to use

43:46

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, things like that.

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, things like that.

43:56

We're long ways before, you know, true AI companies are coming, but it's, but it's on its way. We need something unusual this summer. The our entire technology team shut down for a week,

We're long ways before, you know, true AI companies are coming, but it's, but it's on its way. We need something unusual this summer. The our entire technology team shut down for a week,

44:07

went home, and their only assignment was to learn about AI the entire week. Read about it think about it, talk to people. John Sean did that too. Yeah. I did the same thing. I shut down for a week. Yeah. Just to get up. Just feed because it is a very important thing that we all need to be thinking about. And then came back, you know, compare notes and make sure that our our companies are thinking about it. Did you do it too or just the engineers?

went home, and their only assignment was to learn about AI the entire week. Read about it think about it, talk to people. John Sean did that too. Yeah. I did the same thing. I shut down for a week. Yeah. Just to get up. Just feed because it is a very important thing that we all need to be thinking about. And then came back, you know, compare notes and make sure that our our companies are thinking about it. Did you do it too or just the engineers?

44:28

I and what no. These are not engineers. This is the the investment people on on the tech side.

I and what no. These are not engineers. This is the the investment people on on the tech side.

44:34

So I do it on a more continual basis. You know, I'm spread thinner than other people.

So I do it on a more continual basis. You know, I'm spread thinner than other people.

44:39

So you know, I have sixty 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

So you know, I have sixty 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

44:48

Yeah. As one done.

Yeah. As one done.

44:49

Nice flex. I love that. Then I'm then I'm off the grid, and I don't have a choice.

Nice flex. I love that. Then I'm then I'm off the grid, and I don't have a choice.

44:55

I'm gonna change all of my, my, my, auto reply things to I'm in Antarctica even though I'm just actually in Thomas. No. That's the only two times I'm truly optimistic.

I'm gonna change all of my, my, my, auto reply things to I'm in Antarctica even though I'm just actually in Thomas. No. That's the only two times I'm truly optimistic.

45:06

You,

You,

45:07

you, you, you, like, violate this rule that I have for myself. And, you you do it so wonderfully, which is focus. 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? Eight.

you, you, you, like, violate this rule that I have for myself. And, you you do it so wonderfully, which is focus. 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? Eight.

45:19

Eight. Goddamn.

Eight. Goddamn.

45:21

You could do eight now, but I'm I don't know how big your team was early on, but it seemed like you were still creating a lot of companies. I mean, generally, it was one a year one a year,

You could do eight now, but I'm I don't know how big your team was early on, but it seemed like you were still creating a lot of companies. I mean, generally, it was one a year one a year,

45:30

was that one year we did three between the two of us,

was that one year we did three between the two of us,

45:33

but I would never be able to do eight on my own. I mean, they they take real time.

but I would never be able to do eight on my own. I mean, they they take real time.

45:37

If we are if the roles were reversed, you know, I look up to you. If you were a twenty three year old and and you looked up to me, I would say, man, you gotta do one thing well. And that will pay more dividends. I agree. Oh, well, great. So what's your, like, opinion on that then? No. No. So I think that anyone

If we are if the roles were reversed, you know, I look up to you. If you were a twenty three year old and and you looked up to me, I would say, man, you gotta do one thing well. And that will pay more dividends. I agree. Oh, well, great. So what's your, like, opinion on that then? No. No. So I think that anyone

45:52

I I I and people come to me all the time and say, look, I'd like to have a studio like you. And I'd say, look,

I I I and people come to me all the time and say, look, I'd like to have a studio like you. And I'd say, look,

45:57

don't do that. Start by trying to start a successful company

don't do that. Start by trying to start a successful company

46:02

and end up not being a CEO. That's already not that easy. You know,

and end up not being a CEO. That's already not that easy. You know,

46:06

if you have that, And six months later, the company has raised its external round of financing,

if you have that, And six months later, the company has raised its external round of financing,

46:12

has a full management team in place, and you are its chairman,

has a full management team in place, and you are its chairman,

46:16

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 are you trying to do two or three at the same time on your own?

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 are you trying to do two or three at the same time on your own?

46:28

It's not gonna work. It's not that easy. You know, I have twenty five people. What what does a chairman actually do?

It's not gonna work. It's not that easy. You know, I have twenty five people. What what does a chairman actually do?

46:34

So a chairman is one the in this case is the ultimate person that's gonna be around fifteen years from now. The CEO may change.

So a chairman is one the in this case is the ultimate person that's gonna be around fifteen years from now. The CEO may change.

46:41

This is a person that's gonna guide it and as a co founder.

This is a person that's gonna guide it and as a co founder.

46:44

You know, if along the way, somehow Henry Blodger had quit, that's my problem.

You know, if along the way, somehow Henry Blodger had quit, that's my problem.

46:49

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 I got one company that is gonna have a tricky financing round.

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 I got one company that is gonna have a tricky financing round.

47:00

And, we need to get the the the internal investors together. It's not gonna be easy. I need to do that. So I'm having calls with all them. I need to wrangle everyone, encourage them, push them, come up with the right thing. And what type of relationship do you have with your CEOs? Like, before it's, like, you know, in the first one, two, three, four years, how often are you working with them? Yeah. So, I mean, there, we're gonna have a call probably every week or every two weeks soon to touch base, and then they reach out if they need something.

And, we need to get the the the internal investors together. It's not gonna be easy. I need to do that. So I'm having calls with all them. I need to wrangle everyone, encourage them, push them, come up with the right thing. And what type of relationship do you have with your CEOs? Like, before it's, like, you know, in the first one, two, three, four years, how often are you working with them? Yeah. So, I mean, there, we're gonna have a call probably every week or every two weeks soon to touch base, and then they reach out if they need something.

47:31

I mean, I love their relationship. I feel great about their relationship because, you know, I don't want their job. If I wanted their job, I would've I would've taken their job.

I mean, I love their relationship. I feel great about their relationship because, you know, I don't want their job. If I wanted their job, I would've I would've taken their job.

47:38

I want them to succeed. I don't you know, I don't wanna be CEO of one company. And hopefully, I can stay out of the way because they know much more about the company than I do. But there's certain things where I have either relationship, some experience,

I want them to succeed. I don't you know, I don't wanna be CEO of one company. And hopefully, I can stay out of the way because they know much more about the company than I do. But there's certain things where I have either relationship, some experience,

47:50

tricky issues,

tricky issues,

47:52

introduction to a VC firm where I can add value.

introduction to a VC firm where I can add value.

47:57

And so I I love that relationship.

And so I I love that relationship.

48:00

I like you so much because

I like you so much because

48:02

you do things

you do things

48:03

okay. So Sean and I are in this, like, stupid Twitter world. Where, like, a lot of our friends are popular on the internet. Yeah. And there's this whole

okay. So Sean and I are in this, like, stupid Twitter world. Where, like, a lot of our friends are popular on the internet. Yeah. And there's this whole

48:12

thing that I don't buy into of, like, build in public and, like, use your audience, but, like, it's people selling, like, hundred dollar a month things or something like that. And you have these, like, really big ideas, but all also, like, for how successful you are, we take pride in, like, finding interesting people who are, like, amazing, but not incredibly well known.

thing that I don't buy into of, like, build in public and, like, use your audience, but, like, it's people selling, like, hundred dollar a month things or something like that. And you have these, like, really big ideas, but all also, like, for how successful you are, we take pride in, like, finding interesting people who are, like, amazing, but not incredibly well known.

48:31

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.

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.

48:39

Exactly what I want. And, like, you don't have an audience. Like, you you violate all these, like, stupid roles that people talk about. I do no social media. Why is that? 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.

Exactly what I want. And, like, you don't have an audience. Like, you you violate all these, like, stupid roles that people talk about. I do no social media. Why is that? 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.

48:53

I don't wanna do it. I don't wanna I don't need to be out there.

I don't wanna do it. I don't wanna I don't need to be out there.

48:57

I that time should be used for thinking time

I that time should be used for thinking time

49:00

and managing time.

and managing time.

49:02

And so, yeah, though, 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 Yeah. I mean, I I just think it's awesome. We're 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. I think there's rumors that you're you're gonna run for Mayor. Is that true? So, Tuesday. One is you haven't seen me on TV in a long time.

And so, yeah, though, 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 Yeah. I mean, I I just think it's awesome. We're 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. I think there's rumors that you're you're gonna run for Mayor. Is that true? So, Tuesday. One is you haven't seen me on TV in a long time.

49:26

Right. Yeah. That was that was about four or five years ago. Yeah. When I think I was, like, leaving your office or something like that in the Yahoo building or maybe I was at a friend. I saw you on TV. Yeah, Debbie. I don't think I've been on for

Right. Yeah. That was that was about four or five years ago. Yeah. When I think I was, like, leaving your office or something like that in the Yahoo building or maybe I was at a friend. I saw you on TV. Yeah, Debbie. I don't think I've been on for

49:37

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.

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.

49:47

So I've done that. But I other than that, I do almost nothing.

So I've done that. But I other than that, I do almost nothing.

49:50

I did,

I did,

49:52

think about running for mayor, you know, eight years ago. I've been very involved in politics in many ways,

think about running for mayor, you know, eight years ago. I've been very involved in politics in many ways,

49:59

representing tech community in in every dimension.

representing tech community in in every dimension.

50:03

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

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

50:10

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 you can spend eight months getting the shit kicked out of you and being humiliated. You're like,

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 you can spend eight months getting the shit kicked out of you and being humiliated. You're like,

50:23

I'm gonna be in Antarctica that week. Sorry, guys. Like, can we do this next week? 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.

I'm gonna be in Antarctica that week. Sorry, guys. Like, can we do this next week? 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.

50:34

We do great things together.

We do great things together.

50:37

And so that's a big trade off that I don't wanna make anymore. So I'm gonna keep doing what I'm doing for a long time. You were involved in one company

And so that's a big trade off that I don't wanna make anymore. So I'm gonna keep doing what I'm doing for a long time. You were involved in one company

50:45

that I always that I think could still work -- Mhmm. -- and it didn't work.

that I always that I think could still work -- Mhmm. -- and it didn't work.

50:49

But you almost had it. So you invested or were a board member. You were heavily involved in, I think, in hot jobs, which had an exit, but you you did this other one called, the ladder or ladders -- Yep. -- where at the this was in the mid two thousands where, like, a hundred thousand dollar job was considered good. 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. It that's kinda dismissing it, but it was a job site for hundred thousand dollar jobs Yep. 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

But you almost had it. So you invested or were a board member. You were heavily involved in, I think, in hot jobs, which had an exit, but you you did this other one called, the ladder or ladders -- Yep. -- where at the this was in the mid two thousands where, like, a hundred thousand dollar job was considered good. 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. It that's kinda dismissing it, but it was a job site for hundred thousand dollar jobs Yep. 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

51:24

And then editorial person would try to survey and, and effectively find out what it's like to work there as opposed to the company

And then editorial person would try to survey and, and effectively find out what it's like to work there as opposed to the company

51:33

like, telling you the best, the best,

like, telling you the best, the best,

51:36

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. I've always thought that that was pretty cool. And I always thought that that could have been done effectively. I I remember the was it ladders or the ladders? Yeah. The ladders. And, it's still around, but not nearly as successful as it was. Started in two thousand four. I was one of the early early investors,

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. I've always thought that that was pretty cool. And I always thought that that could have been done effectively. I I remember the was it ladders or the ladders? Yeah. The ladders. And, it's still around, but not nearly as successful as it was. Started in two thousand four. I was one of the early early investors,

51:56

and it's it's actually still there.

and it's it's actually still there.

51:59

I lost, you know, the the LinkedIn, basically, you know, did a much better job.

I lost, you know, the the LinkedIn, basically, you know, did a much better job.

52:03

I'm an investor in ripple match, which is,

I'm an investor in ripple match, which is,

52:06

a jobs oriented company, and aiming at people in college.

a jobs oriented company, and aiming at people in college.

52:10

The job situation is still not fully solved, and that's gonna be one where,

The job situation is still not fully solved, and that's gonna be one where,

52:14

you know, AI will be used intelligently.

you know, AI will be used intelligently.

52:16

Now as a recruiter, as you know, it takes enormous time.

Now as a recruiter, as you know, it takes enormous time.

52:20

To figure out the fifty resumes you should look at, reach out and say, can I have a phone conversation with you, respond to that? Hours and hours and hours and hours and hours. And that needs to be, you know, product ties,

To figure out the fifty resumes you should look at, reach out and say, can I have a phone conversation with you, respond to that? Hours and hours and hours and hours and hours. And that needs to be, you know, product ties,

52:32

and we're on our way, weaving my company as well as many others.

and we're on our way, weaving my company as well as many others.

52:36

Hasn't been sent. Has Alley Corp ever taken any financing or are you strictly using your winnings? Like, or and how much did you use to to fund the company when you first started? Yeah. I did hear that much, but I, you know, I've invested probably

Hasn't been sent. Has Alley Corp ever taken any financing or are you strictly using your winnings? Like, or and how much did you use to to fund the company when you first started? Yeah. I did hear that much, but I, you know, I've invested probably

52:50

two hundred and fifty million dollars into the various companies over the years.

two hundred and fifty million dollars into the various companies over the years.

52:54

And that came from, like, the the the various companies. Yep.

And that came from, like, the the the various companies. Yep.

52:58

Yep. But you but do you take cash flow from anything or is it strictly you you is your income lumpy or not your personal income, but it's like I don't I haven't gotten paid in a long time. I'm purely just investing my own money, but I have all infrastructure

Yep. But you but do you take cash flow from anything or is it strictly you you is your income lumpy or not your personal income, but it's like I don't I haven't gotten paid in a long time. I'm purely just investing my own money, but I have all infrastructure

53:11

and a whole firm that does that. So it's like a has historically been a single LP

and a whole firm that does that. So it's like a has historically been a single LP

53:15

fund.

fund.

53:16

Everyone has carry. It's no different than you and square ventures or Thrive or anything else. Just has one LP instead of many. What are you looking to change or improve? So if we talk to you ten years from now, what do you hope? What do you hope is different?

Everyone has carry. It's no different than you and square ventures or Thrive or anything else. Just has one LP instead of many. What are you looking to change or improve? So if we talk to you ten years from now, what do you hope? What do you hope is different?

53:30

About you or your lifestyle or your businesses that versus today.

About you or your lifestyle or your businesses that versus today.

53:34

So I'm doing most of the things I wanna do now. So

So I'm doing most of the things I wanna do now. So

53:38

One, you know, it's going very well. Results have been great. I spent

One, you know, it's going very well. Results have been great. I spent

53:43

three to four months a year in Europe.

three to four months a year in Europe.

53:45

Working from there.

Working from there.

53:47

I grew up in Europe. My wife is French.

I grew up in Europe. My wife is French.

53:49

I have one child there.

I have one child there.

53:51

And I I enjoy that. So I'm planning on continuing that.

And I I enjoy that. So I'm planning on continuing that.

53:56

Wanna keep doing various, you know, athletic and interesting trips around that that, you know, that that that I enjoy.

Wanna keep doing various, you know, athletic and interesting trips around that that, you know, that that that I enjoy.

54:03

So from a high level, I'm not planning on changing it dramatically. The

So from a high level, I'm not planning on changing it dramatically. The

54:08

I I'd actually love what I'm doing. I think we're having fun and we're gonna continue to do this. I don't wanna make it much bigger.

I I'd actually love what I'm doing. I think we're having fun and we're gonna continue to do this. I don't wanna make it much bigger.

54:15

You know, I don't wanna 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.

You know, I don't wanna 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.

54:29

I'm just trading off. Yeah. I'm very old at this point in this industry, and so I'm, you know, hopefully reading the benefits of the judgment

I'm just trading off. Yeah. I'm very old at this point in this industry, and so I'm, you know, hopefully reading the benefits of the judgment

54:36

that you get after dealing with these things and making lots of mistakes along the way, but a bunch of things going well.

that you get after dealing with these things and making lots of mistakes along the way, but a bunch of things going well.

54:42

Another thing that I like about you is that,

Another thing that I like about you is that,

54:45

you're very emotionally stable. Like, every time, 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,

you're very emotionally stable. Like, every time, 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,

54:59

the article said Henry Blodgett is a very emotional person, which is makes sense because he's a journalist. He's he's a great writer.

the article said Henry Blodgett is a very emotional person, which is makes sense because he's a journalist. He's he's a great writer.

55:05

And during the sale, I think someone was I think he was, like, I'm not even talking to Accessringer or whoever bought it.

And during the sale, I think someone was I think he was, like, I'm not even talking to Accessringer or whoever bought it.

55:12

Kevin has to do it. Like, I I just I can't even be in that room. And, like, it was like, alright, Kevin steps in, and he's the reasonable one, or he's, like, the emotionally,

Kevin has to do it. Like, I I just I can't even be in that room. And, like, it was like, alright, Kevin steps in, and he's the reasonable one, or he's, like, the emotionally,

55:20

like No. I I negotiated I negotiated the entire deal.

like No. I I negotiated I negotiated the entire deal.

55:24

And, you know, and look, I could not be a bigger fan than I am of Henry's, but

And, you know, and look, I could not be a bigger fan than I am of Henry's, but

55:29

it would be like if if someone kidnapped your daughter,

it would be like if if someone kidnapped your daughter,

55:34

are you a good negotiator with the other side? And the answer is no. Right? You're like, give them everything.

are you a good negotiator with the other side? And the answer is no. Right? You're like, give them everything.

55:39

You know, we can just get her back. So we need someone else to do that. And so,

You know, we can just get her back. So we need someone else to do that. And so,

55:43

it was better for me to do it. He was very nervous because I was pushing to get a higher price,

it was better for me to do it. He was very nervous because I was pushing to get a higher price,

55:48

and but we did. You know, we were doing forty million at the time. We sold it for eleven times revenues, which is a big, big number for a media property. It's insane. Yeah. It's insane. We're we're good friends with, one of our best friends is Austin Reef. The founder of Morningbrew. Yeah. And and they're they're killing it for for BI and, Great. That happened now for me, but great acquisition.

and but we did. You know, we were doing forty million at the time. We sold it for eleven times revenues, which is a big, big number for a media property. It's insane. Yeah. It's insane. We're we're good friends with, one of our best friends is Austin Reef. The founder of Morningbrew. Yeah. And and they're they're killing it for for BI and, Great. That happened now for me, but great acquisition.

56:08

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 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

56:16

I think it's important to not get too emotional about any one company, and that's one of the things I can bring to the table. But and when your CEO, you're just so close to it. You're you're you're in the forest.

I think it's important to not get too emotional about any one company, and that's one of the things I can bring to the table. But and when your CEO, you're just so close to it. You're you're you're in the forest.

56:26

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. It's easier for me.

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. It's easier for me.

56:39

A question that we, that we like to ask people

A question that we, that we like to ask people

56:42

is, like, what do you do with your money? So, like, if if, you know, of your of your pie chart, of your hundred percent portfolio,

is, like, what do you do with your money? So, like, if if, you know, of your of your pie chart, of your hundred percent portfolio,

56:48

How do you how do you allocate

How do you how do you allocate

56:51

to different stuff? You know, do you have public equities and just normal bonds and stuff? Are you all in on private company? What are you doing? All in on private companies. So probably ninety percent

to different stuff? You know, do you have public equities and just normal bonds and stuff? Are you all in on private company? What are you doing? All in on private companies. So probably ninety percent

57:00

of my net worth is just in my own farm in in investing in various companies and things.

of my net worth is just in my own farm in in investing in various companies and things.

57:07

I have a I have some in in some VC and private equity firms, you know, as an LP.

I have a I have some in in some VC and private equity firms, you know, as an LP.

57:13

You know, and I do have some real estate

You know, and I do have some real estate

57:16

I bought a building, a commercial real estate building, between on Mott and Broom

I bought a building, a commercial real estate building, between on Mott and Broom

57:22

in between Soho and Bowery.

in between Soho and Bowery.

57:24

And so when you come visit in a year, that'll be the Allie Corp headquarters.

And so when you come visit in a year, that'll be the Allie Corp headquarters.

57:28

There'll be a restaurant

There'll be a restaurant

57:29

in the in the in the in the retail floor five floors of commercial real estate and an amazing roof deck with parties for a hundred and fifty people and dinners for thirty people up there. So it's gonna be a real tech center.

in the in the in the in the retail floor five floors of commercial real estate and an amazing roof deck with parties for a hundred and fifty people and dinners for thirty people up there. So it's gonna be a real tech center.

57:42

So we're it was a shell of a building, and construction starts in a week. We've designed it over the last nine months. It's a super fun project. But it's also a diversification

So we're it was a shell of a building, and construction starts in a week. We've designed it over the last nine months. It's a super fun project. But it's also a diversification

57:51

for me in owning some real estate. But you don't have any public at public equities, other than I imagine you still own stock and,

for me in owning some real estate. But you don't have any public at public equities, other than I imagine you still own stock and,

57:59

mongo.

mongo.

58:00

Yes. But, like, you don't owe you don't have any,

Yes. But, like, you don't owe you don't have any,

58:03

boring,

boring,

58:04

indexes, really. Are you heavy on cash?

indexes, really. Are you heavy on cash?

58:07

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.

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.

58:13

So and I don't know when money's coming back.

So and I don't know when money's coming back.

58:16

Where do you keep your cash just in a in a in -- Yeah. -- as simple as a high yield savings account? Yep. Yep. Exactly.

Where do you keep your cash just in a in a in -- Yeah. -- as simple as a high yield savings account? Yep. Yep. Exactly.

58:23

I need to be super liquid. Dude, that's so fascinating. This is awesome. Kevin, thanks so much for coming on. We, 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. It's also, you know, the premise of our podcast. When we don't have guests on, that's all we're doing. We're thinking about that. And we're we're brainstorming what that could look like. And so our entire audience is people who like hearing about those opportunities or stories of people capitalizing on them. So I think this is, you know, very, very good fit. Thanks for thanks for doing this. Right. Well, thanks for having me on. This is fun. And, again, good to reconnect.

I need to be super liquid. Dude, that's so fascinating. This is awesome. Kevin, thanks so much for coming on. We, 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. It's also, you know, the premise of our podcast. When we don't have guests on, that's all we're doing. We're thinking about that. And we're we're brainstorming what that could look like. And so our entire audience is people who like hearing about those opportunities or stories of people capitalizing on them. So I think this is, you know, very, very good fit. Thanks for thanks for doing this. Right. Well, thanks for having me on. This is fun. And, again, good to reconnect.

59:00

And I hope you realize, like, I'm not just talking shit. Like, you had a really big imp you you you had a big impact in my life, And, I'm gonna be following a a bunch of stuff that you do. And and I have this document that I it's like,

And I hope you realize, like, I'm not just talking shit. Like, you had a really big imp you you you had a big impact in my life, And, I'm gonna be following a a bunch of stuff that you do. And and I have this document that I it's like,

59:14

five hundred pay five hundred words of the notes that I took when I talked to you. And I've and you actually predicted that how much we were gonna get acquired for, by the way, you you you nailed it. Yeah. You you nailed it.

five hundred pay five hundred words of the notes that I took when I talked to you. And I've and you actually predicted that how much we were gonna get acquired for, by the way, you you you nailed it. Yeah. You you nailed it.

59:24

You said, I think in two years, you're gonna get bought for about this much. You nailed it.

You said, I think in two years, you're gonna get bought for about this much. You nailed it.

59:28

You you predict two other acquisitions in the media space as well in my notes. I I'll share it with you so you see, the notes But, you've had a really big impact on me, and and it's really cool to talk to you, and, hopefully, we could stay in touch. Yeah. Of course, we it sounds like we need a an an in person meeting

You you predict two other acquisitions in the media space as well in my notes. I I'll share it with you so you see, the notes But, you've had a really big impact on me, and and it's really cool to talk to you, and, hopefully, we could stay in touch. Yeah. Of course, we it sounds like we need a an an in person meeting

59:42

we need to get together and and see what the next five years are gonna look like. Let's do it, man. I would love that. And and and we appreciate you. Thanks for coming on. Alright. Thanks.

we need to get together and and see what the next five years are gonna look like. Let's do it, man. I would love that. And and and we appreciate you. Thanks for coming on. Alright. Thanks.

Sync with video