0:00
you you like violate this rule that I have for myself and uh you you do it so wonderfully which is focus or at least it appears as as you do.
Search this video
0:06
You like launch like I don't know how many companies a year do you launch? Eight. Eight. God damn. All right, we're live.
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Kevin, do you This is Kevin Ryan. Do you remember me?
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I don't remember where we met.
0:28
I know we've met, but I don't remember where. That's good.
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Okay, you don't have to remember.
0:32
So, basically, I'm going to tell you why. This is funny.
0:34
So, basically, I've studied you for maybe 10 years.
0:38
So, you started uh you were the president of uh and CEO of Double Click, which had like a a billion dollar plus exit, and then you have started like four or five companies that are one's worth, I think, 28 billion today, one's worth uh uh you have a couple billion dollar exits.
0:52
dollar exits. you started Business Insider and I cold emailed you maybe 50 times and one of those times because I admired you so much and we'll talk about your career but I I wanted to be like you and one of those emails you finally replied and you just said like thanks for the updates whatever and then I lied and I said I'm going to be in New York tomorrow can I get 20 minutes of your
1:16
time and you let me do that and I came to your office for literally 20 or 30 minutes we had such an impactful conversation and You did another follow-up call with me and I have the notes from those calls and this was in
1:27
2017 and you made a bunch of predictions about my life as well as the media business and a few other things that were 100% true and I refer back to that note sheet on a consistent basis to help make some decisions. Oh, interesting. Well, I'm glad I Oh, interesting.
1:41
Well, I'm glad I sometimes I get lucky and I get it right.
1:45
And you want to know what your your PR people emailed us to get you on the pod.
1:50
So, the tables have turned, my friend. Welcome to my world. Exactly.
1:53
[laughter] But I just want to say like I've admired you for a long time.
1:57
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.
2:04
And Kevin, uh you don't know me, but I I did not stalk you.
2:06
I did not cold email you.
2:08
In fact, I was a little bit uh just jealous of you because I was at the time working in a um when Sam was telling me about you, I was working at a startup incubator studio.
2:17
And so we were launching four or five companies a year.
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And um after three or four years I was like I don't know if this model even works.
2:26
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 niche.
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And he's like well I don't know this guy Kevin Ryan seems to do it.
2:36
He's cranked out four or five billion dollar companies out of this.
2:39
And I was like I guess I should shut up and uh just you know I guess it's not the model that's the problem. It's me.
2:45
Uh, so you know, I I I think not only is it cool that you bu built big media companies, it's cool that you made the the studio model work when very few people have been able to do that. Yeah.
2:56
No, no, I still enjoy it.
2:56
Uh, by and large, it's still working.
2:59
You know, things go wrong.
3:00
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.
3:05
And so, that's what's so fun.
3:07
And look, there there are more things to be done.
3:09
There are many problems in society that have not been solved.
3:13
And basically the highlevel story of you is you uh you had like a normal corporate career but then you kind of like worked your way into uh double click which eventually I think became adwords at Google. Exactly. Yeah.
3:25
So Google bought it for about $3 billion in 2007.
3:27
Uh company started in 1996. I was there for 9 years.
3:32
It was public for seven years.
3:34
First four years went from 10 people when I joined to 2,000 which so crazy in 25 countries.
3:40
So that's what I spent my early 30s doing.
3:41
Um then we spent three years bringing back to a thousand people as the internet collapsed and 70% of our clients went bankrupt. So don't do that.
3:51
Uh then we we had huge market share controlled basically ad technology and so then uh Google bought it and then I started uh business insider you know [ __ ] and guilt.
4:03
I want to point one thing out in this journey by the way your career starts at credential.
4:07
Uh so shout out to all the listeners out there who are in boring companies right now.
4:11
Boring huge companies, consultants and bankers out there.
4:14
There is hope for you yet.
4:14
Um so you did like potential Euro Disney blah blah blah and then you joined Double Click as employee 20 but you you they brought you in I guess as like a senior person at the time. Yeah. Yeah.
4:25
Uh what happened is I had launched an internet website for EW Scripts which is a media company and I was the COO and CFO of a division of that company.
4:34
Wasn't it basically just like Gilbert comics or was it Exactly. Yeah.
4:37
Gilbert comics and and we had other comics.
4:40
We owned Peanuts and a lot of other ones but on a relative basis it became very successful as a website.
4:45
We sold uh advertising uh e-commerce uh so things that were not that easy to do because we didn't have the vendors at the time.
4:51
So I went to the parent company and said look we should build up an internet division and they said no.
4:56
And so I thought you know I actually believe that the internet's going to be a huge which is obvious now but you know a huge part of the next 25 years.
5:03
I want to go do this full-time.
5:05
So, I was going to go start a company.
5:05
I ran across Double Click that was already in the adtech space.
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They convinced me to join them.
5:11
Instead of starting my own company, I became the the c the CFO, the president, and then the CEO.
5:18
And then when we met, you basically you you kind of outlined after selling Double Click, you said basically my partner Dwight and I, we came up with this thing where we called it Ali Corp.
5:30
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 $300,000 and we say you have 6 months.
5:39
Let's see if we can make this work together.
5:41
And you did that with Insider Business Insider which I think had a $500 million exit.
5:46
You did it with Zola which is still running and kicking ass.
5:49
I believe you did it with with Guilt which I think got to like 500 million in sales but it didn't end up working out wonderfully I think you said. Yeah.
5:57
I mean, we sold for 250 million, which was less than we thought, but it's still obviously, you know, a real number. Good. Yeah. Great.
6:03
And then you you can go ahead and correct me, but you've done this with like four or five companies.
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I I remember this meeting from 2018. I said 300,000. That was wrong, right? Yeah.
6:13
So, we started each company with a million dollars, so 500,000 from each one of us.
6:17
And that was for Guilt, Business Insider, and [ __ ] Uh, and then we I did after that, Dwight semi-retired.
6:25
And so I did that with uh Nomad, I did that with Zola.
6:28
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.
6:36
I mean MongoDB right now is trading I think at I think its market cap is $26 billion today.
6:40
I'm sure at it at COVID peak it was like 40 or 50.
6:46
That's not a lot of money for the outcomes. No. No.
6:48
And look, we had to raise a lot of money.
6:49
I mean, [ __ ] between being a private and public company, raised and lost a billion dollar before they had a profitable quarter, and now already make $300 million a year in profits.
7:00
So, that's why it's so valuable is because it's it's just an incredible company, growing quickly, enormous market share, and is going to grow for the next 10 years.
7:10
It'll be a $50 billion company.
7:12
Well, you told me in our call, you said one of my notes is basically if you're not hiring fast enough and and by the way, this is like this is the VC route, but you said if you're not if you're not hiring fast enough and losing money, aka investing, you either haven't figured it out or you don't believe that your idea is good enough.
7:33
Um, and so you need to grow grow faster.
7:37
Well, and but you you don't want to grow fast just to grow fast.
7:38
If you have a good idea and if you're hiring a salesperson who costs $150,000 and they're selling $500,000 worth, you need to hire those people all day long because you have an opportunity.
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And if you have other products to create, you should hire these engineers to to build it.
7:55
So again, it's not spending money to spend money.
7:57
But if you're building a big company, it's going to take eventually a thousand people or 2,000 people to do a billion dollars in revenue.
8:03
Well, and you your analogy was you go, "Look, if I bu if my idea is good enough, I'm going to build a machine that turns $1 into $2, and if I have that machine, what are you going to do?
8:14
You're going to go get as much money as you can and back that truck up into that machine and dump it in there." Exactly.
8:21
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.
8:25
You know, you run out of market share.
8:27
Uh it's not as big a market as you think.
8:29
Something's not working as well.
8:30
And so then the right thing to do is to not invest.
8:32
And I have companies right now that we've cut 30% of the people in the last year because given this market and what they were doing, we had too many people.
8:42
So there's also a note in that call that I thought was really useful.
8:43
So Sam, I'm looking at Sam's notes from your call like back in 2016.
8:46
Sam's building the hustle.
8:48
He's trying to figure out what to do next.
8:49
I I assume you were considering raising money because you wrote this down and I thought it was uh it's obvious when you hear it, but I most entrepreneurs I don't think think this way, which is you said, let's say you're going to raise $2 million at a $20 million valuation, so you're going to dilute 10%.
9:06
And you're saying, you just have to ask yourself, if I took that $2 million and I invested it into growth, people, whatever over the next 18 months, is our company going to be worth more than 10% versus if we do not?
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And if it is, then I need to do that. I should do that trade.
9:20
And if it's not, I should not.
9:22
And uh did I capture the the logic properly there? Yeah. No, exactly.
9:26
That's what you have to look at.
9:28
And you know, you don't you don't want to raise too much in that round because if you sold 10 million, then that's very expensive capital.
9:34
If you think it's going to be worth $100 million someday or $2 million, you should raise that money later.
9:40
But you do need to get moving.
9:42
And time is never on your side.
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you know, any good idea I've come up with eventually, even if it's six months later, three other people are going to come up with the same idea.
9:52
So, you need to move quickly.
9:55
People tend to they most people understand the the risk of doing something.
9:59
They understate the risk of not doing something.
10:03
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.
10:10
So, double case is the perfect example.
10:11
We expanded to 25 countries before our first country was profitable.
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So if we were a big company, everyone would have said, "Look, let's wait and see and make sure our model works."
10:21
But the result was if you were Proctor and Gamble or Caterpillar or IBM, who did you work with?
10:26
You worked with us because we had operations in 25 countries and you have offices in those countries.
10:33
You didn't work with our competitor who had offices in six countries.
10:36
As a result, we swept the market.
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We lost a bunch of money but we were able to fund it.
10:41
And that is the reason today 25 years later that you know uh Google still has a commanding shares because we got it early on and it's never been given up but you're taking a chance.
10:52
I mean there there are times when you invest in something and it it doesn't work that well and you're like wow we should have waited.
10:58
You don't have time to wait.
11:01
What insight was insider business insider was that?
11:03
So, you sold Double Click.
11:06
You back then when you and I met, you actually told me how much money you made off the DoubleClick sale.
11:09
I won't say it unless you want to say it, but did you um which I thought it was amazing that you told me this.
11:15
I was like, damn, this guy's helping me out so much by telling me all this information.
11:20
Did you you and Dwight got together to start I don't know if you call it an incubator or whatever you call Ali Corp, but did you was insider the first idea that you had and what led to that?
11:30
What led to the insight to start that? Yeah.
11:34
So, the insider idea was so simple that you can't even give us credit for it. So, this is 2007.
11:38
I love business publications and media publications.
11:40
So, I I'm a sort of a compulsive reader of that.
11:45
And I didn't have the publication I wanted.
11:47
And [clears throat] 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.
11:58
Thinking that's impossible.
11:58
And the reason is that they were still on that schedule of the paper comes out the night, you know, the the morning articles have to be done late at night and so at 10 a. m. 10 a. m.
12:08
no one's updating anything.
12:10
And so they just had not adapted.
12:12
And don't forget uh your we only got mobile phones in 2008.
12:18
And so then all of a sudden all day long you're in the taxi.
12:21
Of course you want to get an update on what's happening.
12:22
So we the things we did are so obvious and done today but they were we were early which is updating things continually writing stories that were not complete in a way.
12:34
We'd hear a rumor that X company was buying Y company.
12:36
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.
12:42
Um and so then you get more information and so you maybe write four or five stories during the day as you get more and more information.
12:50
And we also had a point of view.
12:52
So, you know, we'd write uh so and so just overpaid for a company.
12:55
It's more important that we have a smart point of view than that we're right in the long term.
13:01
And so, and we did a great job of making sure we showed up in search results.
13:07
So, again, everyone does that today.
13:09
At the time, no one cared about headlines because if you had Business Week magazine, does the headline result in more revenue for you? No.
13:18
But when we we would AB test three headlines very quickly on a story and realize what was working.
13:22
And so you know what I'm proudest of is that Business Insider is at 300 million uniques today and never spent $1 in advertising. Yeah.
13:33
You told me well you said you you you said we were just we were going to just turn out these articles which um is common now.
13:41
But you go you had this really cool insight. you go.
13:43
It It's kind of like Honda in 1985 versus General Motors.
13:48
Americans laughed at the Honda uh car.
13:50
They said, "This is just too flimsy. This isn't good."
13:52
But they're going to like capture some market share and they're going to improve.
13:58
And you said it's kind of like that with Business Insider.
14:00
The the the quote the critics or the the real people in the industry, whatever you want to call them, they laughed at you and they said, "This is just low quality. This is junk."
14:10
And you're like, "But we're going to get more traffic than you."
14:12
And I think it took like 5 years or something, but we got more traffic than Wall Street Journal.
14:16
And now they're looking at us that like, holy crap, you surpassed us and we could afford to have more substantial journalism that maybe is taken more seriously if if that's even I I would guess by 2015 we had seven people covering military and defense. That's deep coverage.
14:34
I mean, you you you have a lot.
14:36
You're writing great stuff.
14:38
In the beginning, obviously, we had, you know, five journalists covering the whole world.
14:41
it's not going to be amazing, but that that is a good parallel.
14:44
And we the product did get better over time.
14:46
We started winning awards.
14:47
Uh but it always was intended to be a different positioning. It was punchier.
14:51
It appealed to younger people. Uh it was opinionated.
14:54
You know, it's just a different product.
14:56
Uh but I think I think the company, you know, Henry Blah, who's still the CEO, has done an extraordinary job over 15 years.
15:03
And a lot of these insights came from him.
15:07
and he was one of seven people I interviewed for that job and he killed it.
15:13
Uh what did you see in him that uh made you pick him?
15:15
Yeah, I know if you remember it was a bold choice because Henry had had some issues on Wall Street.
15:18
Um so you some people felt like he was tainted.
15:21
I knew that he and the the issues by the way were I think he got accused of was it insider trading or not insider trading at all.
15:29
What happened was at the time what was standard there was that uh the Wall Street analyst would come pitch the company that was going to go public and they would say look we're going to great write great things about you which is potentially a conflict with their recommendations to their uh their their companies their investors. Um, everyone did that.
15:48
Henry actually wrote internal emails saying, "I feel really uncomfortable with this," which then was used against him.
15:55
You know, no one else did that.
15:57
And so, legally, I don't think he did anything wrong.
16:00
Uh, everything he wrote was approved by his superiors and and order.
16:06
But anyway, uh, you know, some people felt like he was tainted. I didn't at all.
16:10
Um, what I did know is he was an incredible writer and he was a perceptive journalist.
16:14
He was writing pieces for The Atlantic.
16:16
I mean, he's just so good.
16:19
I mean, he's so talented.
16:21
And he also he truly understood internet journalism.
16:24
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.
16:29
Uh Henry had was was fresh.
16:32
He had never really worked in a newsroom, which can be viewed as a weakness.
16:36
I viewed it as a strength.
16:38
And so, he changed the rules and we were willing to do that.
16:41
And he did an incredible job.
16:43
you know, that same strategy of kind of like start with the content quickly that gets traffic.
16:49
Don't try to be don't look for kind of like the peer acclaim in the industry.
16:54
Look for what the market wants and then over time improve the quality.
16:56
That was also BuzzFeed strategy.
17:00
But today I'm looking at the BuzzFeed stock. It's 36 cents.
17:01
It's a $50 million market cap.
17:04
What do you think they got wrong?
17:05
But what happened to BuzzFeed?
17:07
Because it seemed like they were they had that whole that same playbook.
17:10
And Jon Bretty, if you ever hear him talk, he seems like, you know, whip smart in the same way.
17:16
For me, it's very clear, and I I felt this from day one, even when they were theoretically worth $2 billion.
17:19
I rarely ran into someone who said, "I love reading BuzzFeed every day.
17:25
I I don't believe they built up a true brand."
17:30
They showed up in search results, they got traffic, but there were, you know, many, many people that religiously read Business Insider every single day.
17:37
So, it just had a brand that I think was much stronger and more defined.
17:44
And you you you guys have another uh funny part about you, which is I was telling my wife this cuz we were talking I was telling her I was going to talk to you and I was going to and and I followed Dave Portoy on Twitter from Bar Stool.
17:56
Business Insider is the only one to get one up on him.
17:59
So, you guys had this you guys had this article about some some stuff that he had done and he went apeshit.
18:06
He went crazy and Business Insider had the best response, which was no response.
18:12
You guys didn't reply to anything.
18:14
And it's the only time I've ever seen Dave Portoy get one up.
18:20
Uh I wasn't really involved with that whole exchange that happened after uh I we sold the company.
18:24
So, well, I thought it was pretty funny and I uh I thought it was I thought this actually handled it wonderfully and they were the first people that I've saw that got one over on him.
18:36
You know, you know, Kevin, um you you guys have had so many hits come out of the studio and um as somebody who ran a studio for six years and uh did not have billion-dollar hits come out of it, I got to know what's the uh what's the secret?
18:51
What, you know, what was it that you guys were doing differently?
18:54
And I'm sure you've talked to many other people.
18:55
You've seen many entrepreneurs start these labs and you've probably seen the same results that I have, which is that very very few come up with anything that works.
19:02
What do you think you guys did differently than others?
19:05
So it's not that you know detail-wise we do anything differently.
19:09
At the end of the day this is a simple business but hard to do.
19:12
In other words, you need a good idea and you need a good team.
19:17
Uh so that's just there's nothing else.
19:20
Uh so you know we've had some good ideas.
19:22
Uh we do a lot of research.
19:22
You know at any one time we're doing deep dives.
19:27
So someone will spend two and a half months interviewing 50 people doing the same thing that I would do if I were an entrepreneur about to start a company.
19:34
So, we have a lot of knowledge. There's a 50-page deck.
19:36
We've really gone into it and then we're committed and then we go hire a great team and we help that team.
19:42
But again, it's a little bit like watching, you know, I don't know, a good basketball player, a good soccer player. We know what they do. We can see what they do.
19:49
Can I do what they're doing? Not very easily.
19:52
So, I think we've executed well there.
19:54
And, you know, we have a bunch of people, including myself, have a lot of experience doing this.
19:56
It's just a series of judgment calls.
19:58
You know, I think uh I'm able because of the track record able to convince some good people to be CEOs.
20:04
Um that's important too and we you know, we spend a lot of time helping them. So I chair 12 companies.
20:11
So about half my time is spent focus on those 12 which are 12 of our most valuable companies uh to really guide them and make sure that they do as well as possible.
20:19
Walk us through like one of those ideas. So, okay.
20:22
So, for example, two and a half years ago.
20:24
So, I'm uh I'm very interested in psychedelics for mental health.
20:29
I'm the leading funer of the Yale Center for Psychedelic Research.
20:34
You know, I'm involved with a bunch of things, nonprofit research for, you know, pushing psychedelics for forward so they can be legalized either by by the FDA or by state.
20:43
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."
20:48
the person on my team works with me, interviews 50 people, you know, we're talking to everyone and we come up with a solution that was partly influenced by some of the work that's been done at Yale and we started a company called Transcend.
21:02
the person on my team actually, which is unusual, spins out to become the CEO, uh, Blake Mandel.
21:06
Big article in, uh, the Wall Street Journal about five months ago about transcend because we, you know, we we started off at the million half dollars, but we raised $40 million about a year to a year and a half later in two tranches at 80 million pre.
21:23
So big big big big step up, big valuation.
21:26
And we have a compound that you haven't heard of going through the FDA process.
21:30
is in phase two trials right now.
21:33
Uh and so people are obviously optimistic about the future, like the team, like the execution.
21:38
Uh we did some things very well there.
21:40
We have been awarded patents.
21:42
For example, if you follow this industry, you know that you can't patent MDMA or mushrooms because those have been around for a long time.
21:50
But we actually did get a patent for meth alone, which is the compound that we're working on. Uh so so far so good.
21:57
Now, there's still risk, but that company is, you know, we currently have a $50 million position based on our 5 million that we've invested so far, and we think it has a lot of potential.
22:07
What about um like with MongoDB?
22:07
So, um that was started I think in 2007.
22:10
So, Ali Corp was like a little bit early.
22:15
Did you have a team helping you research ideas back then? I didn't.
22:19
That was purely Dwight, myself, and Elliot Horowitz who was the most brilliant young engineer at DoubleClick.
22:26
Now, out of 700 engineers, if you could pick out one person other than Dwight, you would have picked him.
22:32
And so, we started a company together in 2005 called Shop Wiki, which is a search engine for shopping. Did okay, not great.
22:39
We sold it in 2007, made a little bit of money, and then said, "What are we going to do next?"
22:43
And so, came up with this idea.
22:45
Uh, started working on it. It was a very hard slog.
22:47
It's very easy to feel good about it right now.
22:51
For three years, we had zero revenue.
22:55
So, not easy to keep funding going back to VCs with zero revenue, but we had a lot of people using it.
23:01
So, you know, we broke through that, but we had some ugly financing rounds.
23:04
You know, especially back in 2009, 2010, it was not a good time to be raising with no revenues.
23:10
Uh then finally Sequoia came in and then we raised a lot of money and now it does getting close to a $2 billion run rate.
23:21
Did that company make you a billionaire?
23:23
So yeah, I mean look for all of us it definitely uh yeah we all made lots of money on that on that company. Definitely.
23:30
Those three years with no revenue uh at the time were you like people just don't understand that this thing is uh like others don't see it but I see it.
23:36
Or were you like in the fog of war?
23:39
you're like, I don't know if this is a thing, if this is going to make it, but um, you know, let's keep going. No, no.
23:44
I would say that all of us were nervous because uh, you know, you like to have revenue and you're going to run out of money at some point.
23:50
What helped us on the inside was that uh, the utilization, the number of people using the product was free was growing every single month all over the world.
23:59
So there's, you know, probably 50,000 small companies using the product.
24:02
And so, you know, there were hundreds of meetups about [ __ ] and people were showing up and so we could see in a way that the dogs like the dog food.
24:12
Uh, we just needed to then make it good enough that larger companies would pay money for it.
24:19
And then we got there and and the rest is history.
24:21
But what's crazy is like, all right, Business Insider, I understand that. Well, that's media. I get it perfectly. Guilt, that's commerce.
24:29
That's fairly easy to understand.
24:31
understand. Zola kind of mediaish related but like a like I understand that business and then you have like psychedelics which I don't have anything about but then [ __ ] is like highly technical I I I I barely I don't I I don't even know the use case to be honest it's a database company involves
24:47
SQL like I don't even I'm so not technical it's pretty amazing that like are you are you pretty I mean you are now but were you wellversed on what this idea was or did you just trust Elliot so Elliot and Dwight you know were the brains and technical jobs like the product could not have been built without them. I understood the high
25:05
I understood the high level problem which I saw which is that Oracle was not the right database for the future because we were going from structured data to unstructured data.
25:16
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 10,000 videos can you put that into your spreadsheet and you're like well no actually it's not built for that but of course data was moving that way.
25:30
YouTube came out in 2005, video was going to be enormous.
25:34
Uh, so I knew that trend was happening.
25:37
I knew that the Oracle product was extraordinarily expensive for us.
25:39
And so there had to be a cheaper way.
25:42
We had seen Linux come out.
25:44
So that was an open-source, you know, operating system that was enormously successful.
25:49
And so we thought collectively that we needed an open- source database that uh was was structured for the future. And so that was the bet.
25:59
So that I understood if you said five levels down, do I understand the code? No.
26:03
But you know, I was working with anytime you start a company, you know, like I'm not a particularly good writer. Henry is.
26:09
Uh, and he was in charge of that product.
26:12
I knew the market well enough in both cases. High level.
26:15
And then it's about assembling the team.
26:18
You got to think of yourself as you are the coach. You are not the player.
26:22
And if you're a coach and if you manage to persuade, you know, LeBron James and Kevin Garnett and a bunch of people on your team, your team's going to do well. That's actually the job.
26:33
You um you've like with the when you're talking about transcend and you're like, we've got a drug going through FDA trials.
26:38
I had the same reaction I think Sam's having, which is like, man, this guy's pretty fearless.
26:42
Like goes into totally different spaces with totally different business models and um with with probably a whole bunch of like new things you got to learn.
26:50
Um, and even if you're the coach, you know, you're betting money and you need to be able to recruit the right players and you need to steer the ship.
26:56
Um, do you feel like fearlessness is something you have?
26:59
And do you do you notice that like do you feel like sometimes I look at other entrepreneurs and I think, man, I can't believe that more of them are not doing X.
27:07
Do you feel like that about the way you approach entrepreneurship? Like, I don't know.
27:10
I feel like more people should be trying.
27:12
They're thinking this way, but they don't seem to.
27:14
I mean, look, what we do is just a slight variation of an entrepreneur.
27:18
They just happen to I have entrepreneurs working for me and we have a structure and and don't forget we also have you know I have 70 engineers who work for me.
27:25
I have my own in-house outsourced engineering company which helps us build product now very quickly which we've had the last 3 years.
27:31
Uh I own a big chunk of a search firm 10erson executive search firm that we set up so that we can get some of the best talent working for us finding CEOs.
27:42
So we build infrastructure around it.
27:44
But still most of it goes back to a good idea and uh a good team and when we get that right. Yes.
27:52
And by the way last point on on psychedelics. Yeah.
27:54
I had done plenty of work.
27:56
I mean I'm not a scientist but I've gone through the academic papers.
27:59
I know the state of research in psychedelics. I know it's working.
28:02
And look what I am thinking about all the time and everyone here does is where is the world going to be in 10 years?
28:10
That's the north star for what we're doing.
28:12
If something's gonna happen next year, it's too late.
28:14
I need to bet on a 10-year trend.
28:17
So, you know, we do a bunch of things in robotics and automation because I feel good about that trend.
28:22
Psychedelics is a 10-year trend.
28:23
MongoDB was a 10-year trend.
28:23
Um, these are the things we're betting on.
28:28
What are you consuming on a daily basis to spot these trends? Yeah. So, tons of things.
28:31
know one thing I'm on, you know, many many uh newsletters that are industry focused or general focused or science or I I read 40 books a year.
28:41
I'm in conversations with people all the time where you're, you know, there's a lot of learning.
28:46
Uh and then people on my team are more specialized than I am.
28:49
So, you know, I have two MD MBAs who are head up our healthcare practice and then people below them that have worked in healthcare.
28:58
So they were thinking of very specific issues that I probably wouldn't wouldn't think of and the same is I have a person on marketplaces, a person on semiconductors and material science and a person on developer tools and enterprise software and two people on social impact.
29:12
So a lot of what we do is in those areas and I'm a bigger and bigger believer now of industry focus.
29:20
You know it's a you know you and I are not going to think of something that applies to the chemical industry right now.
29:25
But if that's all you did for six months and interviewed 100 people, you'd probably come up with some ideas that make sense.
29:32
And the industries that you care about right now are health, healthare, uh, uh, definitely.
29:37
Uh, then the ones I mentioned, so semiconductors and material science, developer tools, uh, with some security marketplaces, B2B marketplaces, uh, social impact and robotics and automation.
29:51
What's an example of a B2B marketplace that you're interested in? Yes.
29:53
So we invested, we have done a deep dive into the maritime industry.
29:58
So shipping, no one thinks about it.
30:02
Multiund billion dollars, very behind in technology.
30:04
We invested in a company called Boxhub.
30:09
That's a marketplace for those containers that are in container ships based in Toronto.
30:14
Uh most people wouldn't have known about it. We led that round.
30:17
We also have just started a company in maritime that's going to be a e a procurement marketplace.
30:22
So you're a ship, let's say you're arriving in Cartahena, your boiler breaks.
30:26
What are you going to do?
30:30
You know, you weren't planning on that.
30:32
And so having a site you can go to that becomes sort of the Amazon of that and has delivery and can get you those parts.
30:39
Uh everyone in the industry told us that that's needed.
30:41
So we're literally just built a team two months ago.
30:45
There are probably at four people right now and so we're off and running.
30:49
What's that company called?
30:50
It doesn't have its official name yet.
30:53
So, all right, let's use that as an example.
30:54
So, you basically did uh did you just go and somehow network your way into talking to 50 Oh, yeah.
31:02
So, a woman on my team uh absolutely did that and went to two uh maritime conferences.
31:07
So, which she said were fascinating.
31:11
It's basically people from Venezuela, you know, the Middle East, Russia, you know, from all over the world, Greek.
31:17
And so trying to understand history, just a bunch of pirates, the pirates [ __ ] hob hobling around and a bunch of parrots and bird [ __ ] all over the place.
31:26
She said it did not look like her Princeton reunion at all.
31:28
[laughter] So yeah, and so and she met with the couple investors who invest in this space, you know, ship owners, uh, data providers, everyone.
31:39
providers, everyone. They're just trying to understand how does the industry work and I think there's an advantage sometimes coming from outside because some people just say oh that's just how it works here and the person on the outside will be like wait a second it doesn't have to works that way you know
31:52
we can do better right and that's why like you know Henry was the perfect person coming from outside you know when I started guilt none of my initial five people had worked in the fashion industry but we understood the problem it wasn't that complicated so we could create something that was that is interesting and unusual. Uh so that's
32:10
Uh so that's the right approach.
32:12
We just started a company in assisted fertility.
32:14
I'm sure you guys know you have friends, you know, who are getting IVF. I've did it. Yeah.
32:21
My my brother and his husband, you know, uh had a child through surrogacy, freezing eggs.
32:27
That's going to grow for the next 10 years for all the reasons we know about people having children later.
32:32
Sperm counts are down, bunch of things.
32:34
So we we s we started company what uh four months ago.
32:37
We put in a million half dollars and we just signed a term sheet to raise you know5 half million dollars.
32:44
Um a lot of people wanted to do it.
32:47
People are excited about the team.
32:49
Uh we have you know good set of people uh mostly from Stanford business school on this team and it's a big space.
32:53
So uh I'm I'm going to bet on that team and that trend for a while.
33:01
What does that deck look like?
33:01
You said they they do like a or I think a 50-page memo or deck.
33:05
I'm not sure what you said.
33:06
Do you have a structure for it?
33:08
Yeah, it's generally one just talking about the industry. Where are the problems?
33:11
Where are the pain points and then where are the opportunities? What's the product idea?
33:15
So, 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 solved the problem.
33:24
Meaning, if you name anything on the planet Earth just about, you know, you can find a site, they'll have 10,000 of them, it'll be sent to your house by tomorrow.
33:31
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 Marc Jacobs at 50% off online.
33:41
Uh, just no one offered it and so we offered it and people went crazy over that.
33:47
Uh, so e-commerce is very mature.
33:50
Frankly, media is pretty mature right now.
33:54
There's a lot, you know, not that people say to me, I just can't find what I want to want to read.
33:57
Uh, but even, you know, once in a while, we're working on one idea right now, the early stages in the media space, uh, but not not sure yet.
34:05
So, we're looking for problems.
34:05
The health, one of the reasons I like healthcare is because it healthcare is not solved.
34:11
You know, as you guys know, you you have knee surgery, either you or your insurance company are going to pay a crazy amount.
34:18
One, there's too much knee surgery.
34:20
It's going to someone's going to pay 40,000.
34:22
Yet, in France, it's 20,000.
34:24
And the results are better.
34:27
So, can it be done better?
34:27
Yes, it can be done better.
34:29
Do 20 times more black women die in child birth than in Sweden? Yes.
34:35
Is that something that is just inherent and is always going to happen? No.
34:39
We don't do enough prevention.
34:39
There are many structural issues in healthcare that have not been solved and we're we're solving some of them.
34:50
Our software is the worst.
34:50
Have you heard of HubSpot?
34:53
See, most CRM are a cobble together [music] mess, but HubSpot is easy to adopt and actually looks gorgeous.
34:57
I think I love our new CRM.
34:59
Our software is the best.
35:01
[music] HubSpot grow better.
35:05
It sounds to me like what you do is you think about what's the world going to look like in 10 years.
35:08
Um 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 and then then it sounds like you say um cool let's go find out everything we can learn about that space.
35:23
We we go in kind of uh open-minded about what problem we're going to solve.
35:26
We try to figure out uh where all the pain points are.
35:30
And then it sounds like you're looking for what I'll call the big obvious problem, which is if it's too complicated and nuanced, it doesn't sound like you're that interested.
35:39
It's like, uh, hey, you can't find luxury fashion online for 50% off, right?
35:43
Okay, that's like a big obvious problem.
35:45
It doesn't take that much explaining or expertise to even understand the problem.
35:50
Maybe the solution might be might take some expertise, but the problem should be in your face.
35:53
Um once once you're looking in that industry um we uh we have this thing we say on the podcast which is that there are businesses that there are business plans that are what I call one chart businesses.
36:06
You could just look at one chart and it just tells you oh that's yeah that's so obvious.
36:09
Like we were looking at one that was around um uh in the death space around cremation.
36:14
It was like cremation went from I don't know 7% of all things to like 50%.
36:18
is now the majority of uh of of of what choices people make when um when it comes to a funeral.
36:27
And this is like that's a one chart business.
36:29
You can look at nothing else and say, "All right, I know there's big I know there's opportunity when I look at a chart like this."
36:33
Um is is that does that jive with your way of thinking or do you have anything you can add to to our understanding of that? No, no, absolutely.
36:41
I mean, I'll give you another one.
36:43
The cost of labor is going to just keep going up and so you know, waiters were paid $15 an hour.
36:48
Now it's 20 to $25 an hour in New York.
36:54
Unless we change immigration or something fundamentally changes that could be $30 an hour.
36:57
So you know what over time that changes the calculus of automation whether it's making French fries whether it's this you we're all going to have to find ways to use less labor.
37:08
Uh and so when cost of tech goes down and the cost of labor goes up what does that tell you?
37:13
More automation is gonna happen.
37:14
Uh so I'll bet on that trend all day long.
37:17
Yeah, we're an investor in a company that gives robotic massages.
37:21
There's 17,000 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.
37:32
So, you know, we hope they're going to offer massage.
37:35
So, that that's just one example, but I have 10 others.
37:39
We uh Well, what are those 10 others of just of just automation or or other ideas?
37:44
No, just I'll give you another example.
37:46
Another company we invested in is so driverless cars is as you know not legal in most countries most states but having a remote driver is so would you if you're in New York City would you pay money to have a car 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.
38:09
Um, and yet we can have someone in the Philippines or in, you know, Arizona drive the car because we put software and hardware in the in the car. They can see everything.
38:17
That's legal in many states.
38:19
Uh, airports already talking to us uh about um the vans that they have to drive around to bring people to the rental car lots at 2 in the morning. Hardly anyone on there.
38:31
You got to pay someone double time, 40 bucks an hour.
38:34
That should be done by someone remotely.
38:36
So things like that are going to be automated.
38:40
So Sean and I um we've had a bunch of cool people on this podcast.
38:43
So one of our great friends is this guy named Andrew Wilkinson.
38:46
He owns maybe 40 companies, a lot of agencies and and web stuff, mostly bootstrapped.
38:50
It's publicly traded now.
38:54
And then we have this other guy named S who's like 32 years old who owns um a bunch of WordPress plugins basically that bootstrapped a unicorn. Wow. Amazing.
39:04
and well of which he owns most of.
39:06
Um, and so we have a lot of like and and and I fall in this category as well.
39:11
I I bootstrap a lot of my things.
39:13
Um, and then there's this other category.
39:14
So there's a category of people who like bootstrap stuff and just use their cash flow.
39:17
And then oftent times that same group of people prefer to go and buy companies as opposed to build them from scratch.
39:22
You're taking the opposite approach a little bit where you're like, uh, I'm going to fund it.
39:28
It's not going to make money at first, but I and I might go and raise a a a [ __ ] ton more money, but this might be a huge idea and I'll own a small piece of it.
39:38
What um like have you ever considered the bootstrapping model or is your is your you just go big right away?
39:42
And have you ever considered buying?
39:44
What's your like buy versus build kind of mindset? Yeah.
39:48
So, it really depends on the type of business.
39:50
So, if you're running an agency, you just don't need a lot of capital.
39:54
you know, you hire five people who uh and then they agencies make money and then you use that money to reinvest and grow.
40:01
If you're building what I'm building is closer to like a hotel, you know, you have to build the whole building before anyone comes and stays with you.
40:09
So, little different like [ __ ] you got to take years to build a good enough product and there's no way to bootstrap that.
40:15
to bootstrap that. you know it takes 20 50 you know there hundred million dollars generally for those types of companies to get there so that's why it's it's not an option for those things look I would love to have companies that you know I could own all of for example
40:31
the the agency that that I have I said those engineers I basically have an outsourced engineering company I own all of that uh because it has clients and it builds as it gets more clients but those businesses are not as scalable profit margins are generally lower Um those are not the type of business I generally go after. Why why is that? Is it just a matter of Why why is that?
40:50
Is it just a matter of you just enjoy something more?
40:51
Do you think that one is a better better wealth creation?
40:55
Are you mo I mean what's the motivation?
40:57
I just prefer creating a product a real product that's hard uh and then you know making more scalable and building it up over time.
41:04
The vast majority of quite successful companies are in that category.
41:08
The servicesoriented companies you know it's harder it's harder to get to be a unicorn.
41:13
It can happen but there are there aren't that many.
41:15
You over time got more selective on the project selection because I look at you know you did business insider.
41:19
I think you were the C were you the CEO for like a period of time there?
41:24
Nine years is that right?
41:25
No no no I was the chairman for all nine years.
41:28
I did step in I did step in to be the CEO of Guilt when we were growing really quickly.
41:34
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 15 years.
41:41
I stepped into [ __ ] I changed CEOs about eight years ago.
41:46
Uh and for three months I was de facto the CEO as I was doing.
41:50
So you you've run these for a period of time but mostly not.
41:52
Um but but I guess uh when I think about businesses I look at my career and it's like I look back and I think okay of these 10 things I did two of them were like ate up all of my time and gave me a bunch of gray hair for like relatively less payoff versus these other two which was like I just kind of wrote the check.
42:09
It was an obvious opportunity and it just paid me and it was wonderful.
42:12
Have you like what's the best business that you've done in your portfolio that you look back on that has the combination of the value, the pain that it took to get there, you know, um all of that and then do you have a framework around that or do you think it's just luck of the draw?
42:28
I think it's like luck of the draw.
42:28
I mean [ __ ] is the one where you know I got the most return for the least amount of money.
42:33
I mean I I essentially never worked there full-time.
42:36
Uh so chairman for 13 years um and yet it's a super valuable and you know fascinating company that's going to be around for the next 50 years.
42:46
Uh but you know I I'm intellectually curious.
42:49
So what I love about what I do is that you know in an hour I might be in a meeting on psychedelics and then on you know semiconductors and I have to try and keep up and learn something about these.
43:01
Um and that's what's so you know we have one in cardiology.
43:03
Uh there's so many different things.
43:06
It's that's what's amazing.
43:08
And for someone who's thinking about 10 years, I'm a little surprised.
43:10
I don't see AI all over this doc.
43:13
Uh you know, you're not saying AI AI.
43:15
It sounds like it might be embedded in some of these things that you're doing.
43:18
Uh like might be a tool you use, but are you bearish on it for some reason or what's your thinking around AI? No, I I say two things.
43:26
One, it's coming down now, but if it were six months ago, you know, the pricing on AI was insane.
43:33
you know, three people walk in and say, "We're worth $100 million cuz we're going to put together an AI company." Just didn't make sense.
43:38
So, we didn't make any direct investments there.
43:39
Um, each we're really encouraging each one of our companies to use AI.
43:44
And I think the, you know, the real use of AI in the short term is going to be much more mundane.
43:49
It's optimizing customer support, you know, making your coding more efficient, things like that.
43:53
Uh, we're a long ways before, you know, true AI companies are coming, but it's but it's it's on its way.
44:00
We did something unusual this summer.
44:02
The our entire technology team shut down for a week, went home and their only assignment was to learn about AI the entire week, read about it, think about it, talk to people. Sean did that too.
44:15
Yeah, I did the same thing. I shut down for a week. Yeah.
44:17
Just to get up to speed because it is a very important thing that we all need to be thinking about and then came back, you know, compared notes and made sure that our our companies are thinking about.
44:26
Did you do it too or just the engineers?
44:28
I No, these are not engineers.
44:28
this is the the investment people on the on the tech side.
44:33
So I do it on a more continual basis.
44:36
You know, I'm spread thinner than other people.
44:37
So, you know, I have 60 board meetings a year.
44:39
I have a lot of things I have to I can't shut down as easily unless I'm at Burning Man or Antarctica. [laughter] Yeah.
44:48
As one [clears throat] does. Nice flex. I love that.
44:51
Then I'm then I'm off the grid and I don't have a choice.
44:53
[laughter] I'm going to change all of my uh my my auto reply things to I'm in Antarctica even though I'm just actually in No, that's the only two times I'm truly off the grid.
45:06
You uh you you like violate this rule that I have for myself and uh you you do it so wonderfully, which is focus, or at least it appears as as you do.
45:14
You like launch like I don't know how many companies a year do you launch? Eight. Eight. God damn.
45:19
And you could do eight now, but I I don't know how big your team was early on, but it seemed like you were still creating a lot of companies.
45:27
I mean, generally it was one a year. One a year.
45:28
Um there was that one year where we did three between the two of us.
45:30
Uh but I would never be able to do eight on my own.
45:34
I mean, they they take real time.
45:37
If we if the roles were reversed, you know, I look up to you.
45:39
If you were a 23-year-old and and you looked up to me, I would say, man, you got to do one thing well and that will pay more dividends. I agree. Oh, well, great.
45:47
So, what's your like opinion on that then? No. No, no.
45:50
So, I think that anyone I I people come to me all the time and say, "Look, I would like to have a studio like you."
45:55
And I'd say, "Look, don't do that.
45:58
Start by trying to start a successful company and end up not being the CEO.
46:03
That's already not that easy."
46:05
You know, if you have that and 6 months later the company has raised its external round of financing, has a full management team in place and you are the chairman, you can then decide to do another one.
46:17
You know, you can't truly be CEO of multiple companies, but you can be chairman of multiple companies.
46:23
But you got to start with one.
46:23
And if you try and do two or three at the same time on your own, it's not going to work. It's not that easy.
46:28
You know, I have 25 people.
46:31
What does a chairman actually do?
46:34
So, a chairman is one in this case is the ultimate person that's going to be around 15 years from now. The CEO may change.
46:40
This is a person that's going to guide it and as a co-founder.
46:42
you know, if along the way somehow Henry Blahad quit, that's my problem. I need to find a CEO.
46:50
I need to solve that for the board.
46:52
So, you're just the most active board member.
46:54
We had other investors, but everyone knows like I have one company that is going to have a tricky financing round and uh we need to get the the uh the internal investors together.
47:04
It's not going to be easy. I need to do that.
47:06
So, I'm having calls with all them.
47:08
I need to wrangle everyone, encourage them, push them, come up with the right thing.
47:12
And what type of relationship do you have with your CEOs?
47:15
Like before it's like uh you know in the first one, two, three, four years.
47:20
How often are you working with them? Yeah.
47:21
So I mean there uh we're going to have a call probably every week or every two weeks soon to touch base and then they reach out if they need something.
47:29
I mean I love the relationship.
47:31
I feel great about the relationship because you know I don't want their job.
47:34
If I wanted their job I would have I would have taken their job.
47:36
Um I want them to succeed.
47:39
I don't, you know, I don't want to 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.
47:46
But there's certain things where I have either relationship, some experience, tricky issues, uh, introduction to a VC firm where I can add value.
47:55
Uh, and so I I love that relationship.
48:00
Uh, I like you so much because 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.
48:10
And there's this whole thing that I don't buy into of like build in public and like use your audience, but like it's people selling like $100 a month things or something like that.
48:19
And you have these like really big ideas, but also like for how successful you are.
48:23
We take pride in like finding interesting people who are like amazing but not incredibly wellknown. You are really good.
48:31
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 rules that people talk about. I do no social media. Why is that?
48:48
You know, it's I look I think other people use it very well and they like doing it.
48:51
I don't want to spend the time.
48:52
Uh I don't want to do it.
48:52
I don't want to I don't need to be out there.
48:54
Uh I that time should be used for thinking time and managing time.
48:59
Uh and so yeah know the people who are on my marketing team know that the goal is that we are very successful and that when I walk into a restaurant, no one knows who I am. Yeah.
49:12
I mean I just think it's awesome.
49:14
We're Well, I but you you're on like CNBC and [ __ ] like that.
49:16
Every once in a while I'll see you there.
49:17
I think there's rumors that you're you're going to run for mayor. Is that true? So two different things.
49:22
One is you haven't seen me on TV in a long time. Right.
49:26
Yeah, that was that was about four or five years ago.
49:27
I think I was like leaving your office or something like that in the Yahoo building or maybe I was at a friend's I saw you on TV.
49:34
Yeah, that'd [snorts] be I don't think I've been on for at least 5 years.
49:35
So, yeah, I don't do that.
49:39
You know, actually podcasts are the only thing I do because it's sort of enjoyable.
49:42
You don't need to prepare.
49:44
You have a good conversation. Uh so, I've done that.
49:45
But I other than that, I do almost nothing.
49:50
I did uh think about running for mayor, you know, eight years ago.
49:54
I've been very involved in politics in many ways.
49:58
Um representing tech community in in every dimension.
50:00
Um all my life I thought I would want to that' be the one other thing I'd want to do and then decided, you know, seven years ago that I didn't want to do that.
50:08
It's it's a miserable process.
50:11
You know, if you said to me you could be mayor tomorrow, I would actually do it.
50:14
If you said to me, "No, no, what I mean is that you can be one of seven candidates.
50:17
You can spend eight months getting the [ __ ] kicked out of you and being humiliated.
50:22
You're like, "Uh, I'm going to be in Antarctica that week. Sorry guys."
50:24
Like, "Can we do this next week?" No.
50:27
And 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.
50:33
Uh, we do great things together.
50:35
Uh, and so that's a big trade-off that I don't want to make anymore.
50:39
So, I'm going to keep doing what I'm doing for a long time.
50:43
you were involved in one company um that I always that I think could still work and it didn't work uh but you almost had it.
50:50
So you invested or were a board member.
50:53
You were heavily involved in I think in Hot Jobs which had an exit, but you did this other one called uh the ladder or ladders where at the this was in the mid 2000s where like a $100,000 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.
51:11
That's kind of dismissing it, but it was a job site for $100,000 jobs. Yep.
51:16
And I remember seeing that.
51:16
I was like, that's pretty cool.
51:18
And I tried launching a company where the user would pay a subscription and then editorial person would try to survey and uh and effectively find out what it's like to work there as opposed to the company uh like telling you the best the best um like you know like the the best stuff.
51:38
But I always you always you had a couple companies in like the job space.
51:41
I've always thought that that was pretty cool and I always thought that that could have been done effectively.
51:45
I remember the was it ladders or the ladders?
51:49
The ladders and it's still around but not nearly as successful as it was. It started in 2004.
51:52
I was one of the early early investors uh and it's it's actually still there but lost you know LinkedIn basically you know did a much better job.
52:02
Uh I'm an investor in Ripple Match which is uh a jobsoriented company aiming at people in college.
52:08
aiming at people in college. the job situation is still not fully solved and that's going to be one where uh you know AI will be used intelligently as a recruiter as you know it takes enormous time to figure out the 50 resumes you should look at reach out and say can I have a phone conversation with you
52:26
respond to that hours and hours and hours and hours and hours and that needs to be you know productized uh and we're on our way we being my company as well as many others hasn't been so has Ali has Ali Corp ever taken any financing or are you strictly using your winnings like and how much did you use to fund the company when you first started? Yeah, I didn't hit that much but I you
52:46
Yeah, I didn't hit that much but I you know I've invested probably $250 million into the various companies over the years and that came from like the the various sales. Yeah.
52:58
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 No, I I don't I haven't gotten paid in a long time.
53:07
I'm purely just investing my own money, but I have a whole infrastructure and a whole firm that does that.
53:12
So, it's like a has historically been a single LP fund. Everyone has carry.
53:16
It's no different than Unquair Ventures or Thrive or anything else.
53:19
Just has one LP instead of many.
53:22
What are you looking to change or improve?
53:24
So, if we talk to you 10 years from now, what do you hope what do you hope is different about you or your lifestyle or your businesses that versus today?
53:34
So, I'm doing most of the things I want to do now.
53:36
So one, you know, it's going very well. Results have been great.
53:39
I spend 3 to four months a year in Europe working from there. I grew up in Europe. My wife is French. Uh have one child there. Uh and I I enjoy that.
53:50
So I'm planning on continuing that.
53:54
Want to keep doing various, you know, athletic and interesting trips around that that you know that that that I enjoy.
54:01
So, from a high level, I'm not planning on changing it dramatically.
54:06
The I I actually love what I'm doing.
54:08
I think we're having fun and we're going to continue to do this.
54:12
I don't want to make it much bigger.
54:13
You know, I don't want to have that many more people.
54:17
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.
54:25
And that's where I think I I add value. I'm just trading off.
54:29
I'm very old at this point in this industry.
54:31
And so I'm, you know, hopefully reaping the benefits of the judgment that you get after dealing with these things and making lots of mistakes along the way, but a bunch of things going well.
54:43
Another thing that I like about you is that um you're very emotionally stable.
54:47
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.
54:53
And I read an article about Business Insider selling and I think uh the article said Henry Blahett is a very emotional person which is makes sense cuz he's a journalist.
55:03
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 Axel Springer or whoever bought it. Uh Kevin has to do it.
55:12
Like I I just I can't even be in that room. Yeah.
55:14
And like it was like, "All right, Kevin steps in and he's the reasonable one or he's like the emotionally uh like no, I I negotiated I negotiated the entire deal."
55:23
Uh, and you know, and look, I could not be a bigger fan than I am of Henry's.
55:27
But it would be like if if someone kidnapped your daughter, uh, are you a good negotiator with the other side?
55:36
And the answer is no, right?
55:37
You're like, give them everything.
55:37
Uh, you know, we just get her back.
55:39
So, we need someone else to do that.
55:41
And so, um, it was better for me to do it.
55:43
He was very nervous because I was pushing to get a higher price.
55:46
Uh and but which we did, you know, we we're doing 40 million at the time.
55:50
We sold it for 11 times revenues, which is a big big number for a media property. It's insane. Yeah, it's insane.
55:56
We're good friends with one of our best friends is Austin Reef, the founder of Morning Brew. Yeah.
56:02
And and they're they're killing it for for BI and uh Great.
56:05
That happened after me, but great acquisition.
56:07
Uh I still get that product every day.
56:09
I think they do a really nice job.
56:11
Have a great editorial tone. But you're right.
56:13
I'm I'm don't I mean this 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 and when you're CEO you're just so close to it.
56:23
You're you're you're in the forest.
56:24
I can step back a little bit and sometimes say look you know this is going to 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.
56:37
A a question that we uh that we like to ask people is like what do you do with your money?
56:42
So like if if you know of your of your pie chart of your 100% portfolio, how do you how do you allocate uh to different stuff?
56:51
You know, do you have public equities and just normal bonds and stuff?
56:54
Are you all in on private company? What are you doing?
56:56
All in on private companies.
56:56
So probably 90% of my net worth is just in my own firm in in investing in various companies and things.
57:05
Uh, I have a I have some in in some VC and private equity firms, you know, as an LP.
57:10
Uh, you know, and I do have some real estate.
57:15
Uh, I bought a building, a commercial real estate building, uh, between on M and Broom in between Soho and Bowie.
57:23
And so when you come visit in a year, that'll be the Alley Corp headquarters.
57:27
There'll be a restaurant in the in the in the retail floor, five floors of commercial real estate, and an amazing roof deck with parties for 150 people and dinners for 30 people up there.
57:39
So, it's going to be a real tech center.
57:42
So, we're It was a shell of a building and construction starts in a week.
57:44
We've designed it over the last uh nine months.
57:48
It's a super fun project, but it's also a diversification for me and owning some real estate.
57:52
But you don't have any public public equities other than I imagine you still own stock in uh [ __ ] but but like you don't you don't have any uh boring uh indexes really. Are you heavy on cash?
58:07
Yes, I always keep a lot of cash.
58:09
I need to keep a lot of cash because I don't have you know I don't have a salary so and I don't know when money's coming back.
58:16
Where do you keep your cash?
58:16
Just in a in a in as simple as a high yield savings account. Yep. Yep. Exactly.
58:21
I need to be super liquid.
58:24
Dude, that's so fascinating. This is awesome.
58:27
Thanks so much for coming on.
58:27
We uh as you can tell, big fans and what you've done is is pretty incredible.
58:31
Also, I think there's just like what you do about thinking about where the world is going, what ideas, what opportunities, what problems.
58:38
It's also, you know, the premise of our podcast when we don't have guests on. That's all we're doing.
58:42
We're thinking about that and we're we're brainstorming what that could look like.
58:45
And so, our entire audience is people who like hearing about those opportunities or stories of people capitalizing on them.
58:51
So, I think this is uh you know, very very good fit.
58:55
Thanks for thanks for doing this. Great.
58:56
Well, thanks for having me on.
58:57
This is fun and again good to reconnect and I hope you realize like I'm not just talking [ __ ] like you had a really big you you you've had a big impact in my life and um I'm going to be following a bunch of stuff that you do and and I have this document that I it's like uh 500 p 500 words of the notes that I took when I talked to you and I've and you actually predicted that how much we were going to get acquired for by the way. You you nailed it. Yeah, you you nailed it.
59:22
Um, you said, "I think in two years you're going to get bought for about this much." You nailed it.
59:26
Uh, you predict two other acquisitions in the media space as well in my notes.
59:29
I I'll share it with you so you see uh the notes, but uh you've had a really big impact on me and it's really cool to talk to you and hopefully we can stay in touch. Yeah, of course.
59:38
We It sounds like we need an inerson uh meeting.
59:39
Uh we need to get together and and see what the next five years are going to look like. Let's do it, man. I would love that.
59:46
And and we appreciate you. Thanks for coming on. All right. Thanks, with you.