20VC: Are the Best CEOs the Best Fundraisers, Are the Best Founders Insiders or Outsiders to a Problem, Why Ownership Should Not Be a Focus in VC & The Biggest Lessons Scaling MongoDB to $26BN Market Cap with Kevin Ryan, Founder @ AlleyCorp

24:00So seeing everything is helpful. Do you think investors aren't value? You mentioned there about being a more valuable investor. I just had Trayong from Foundless Fund who was like, investors don't have value. Easily 90 % of the value of a company comes from the CEO and a team. Having said that, making sure you have the right CEO, which is the board slash investor's responsibility, is a single biggest decision. I mean, if you said, why is Mongo a very successful company? You could say, well, because Dave's been running it for the last seven years. I let the previous CEO go and hire Dave because we're getting to a new phase and the board as well.

24:38And I think that single decision was extremely important and well executed, even though Dave has done, obviously, 99 % of the work. The other thing I would say is that the early stages of a company, the investors play a much bigger role. We start so many companies who are early stage, often you have a ACO that has literally never raised money before. So when we get them in front of 50 venture capital firms, that is adding value. When they are hiring a CFO for the first time because they were headed business development. They never actually managed a CFO before. Having a perspective on that is important.

25:12The other thing I would say, I had incredible investors at Double Click. When you are CEO, you are too close to the business. That is your job. And so some distance is often helpful because they would come to board meeting, they've worked with 20 CFOs or seen 20 sales plans. And so they just had a slightly better perspective and once in a while I'll be like you know that's a good point. I had not factor that in, I was too close to it, but my point remains 90 % of it is having the right CEO and the right team. I love serial entrepreneurs, for the reason that you don't need to teach them how to fundraise, you don't need to teach them how to hire ahead of sales.

25:49They've done most of it before and they've fucked up before as well, which means they should have learnt the lessons last Now, they'll make new mistakes, of course, but they won't make some pretty obvious ones. How do you feel about that you said earlier? We liked back first -time founders. And my wrong in terms of my thesis on zero launchpreneurs and that heavy preference there, and how do you think about that? Again, if we look back at consumer businesses out of the top 25 companies, how many were zero launchpreneurs, almost zero? By the way, you'll see an enterprise software, more of a pattern of repeat entrepreneurs, also on average slightly older.

26:2624 -year -olds have trouble starting a database company and building up an enterprise sales force, meeting with the CTO or the CTO of Goldman Sachs, close that deal really doesn't happen that often. So, industries are different. It depends whether the industry knowledge, experience and credibility is extremely important to success and in consumer it isn't. Because I just go look at your app and I like it. I don't really care whether you're 10 years old or 50 years old. What do you think is the biggest determination of rather a company gets product market fit from zero to one? Everyone with says speed is the single biggest determinator or Determining fighter.

27:03Do you agree with that? No, I don't think that speed is the most important thing You do need to get out your product, you know pretty quickly, but it has to be pretty good So for example, we had no revenues after three years at Mongo There's not great because we had to go slower It had to work it had to scale and it had to be secure Whereas for consumer apps, it can be, you can make mistakes. Did you crash your mother at work? Three years in no revenues. I can't remember how many years he said earlier, but nine years in no profits. So nine years in, I knew it was working, there was no problem.

27:37Three years in, we were nervous. We couldn't charge for it yet, it was getting better and better. We knew the industry is very big, we knew there was an opportunity, we knew Oracle was too expensive, and we knew that a non -relational database was a good idea. but you know, you could also just run out of money at some point. We didn't have incredibly successful fund races during that time. But what you could see is that if I showed you one chart, which is how many people are downloading the Mongo database, that was just a straight line going up to the right all over the world. And as long as that kept happening, we thought we were on to something.

28:10Do you agree that companies die more often of indigestion and starvation? I hear it often, Gavin, and I think it's bullshit. I'm like, do you know how many companies die because they run out of cash a lot? By definition, companies only die because they run out of cash. The question is, why do they run out of cash? They run out of cash because they don't have product market fit, because investors are looking at the numbers, looking at the team and saying, I'm not going to put money in here. I do want to discuss the new funds, be human investors and put money in. So, can you share the news with us that I think came out yesterday?

28:42Sure. We've been investing really my money in a different structure for the last decade. We have 120 companies in the portfolio, have made many investments started over 20 companies. But we just announced that it's the first outside fund with outside investors. So we raised it $250 million fund to continue doing what we're doing and continue to both start companies and investing companies largely on the East Coast in New York, but not only heavily healthcare, heavily tech, robotics and social impact. So super excited. It's a great time. Okay, how do you do resource allocation between incubations versus investments?

29:19Yeah, so what I like is being industry focused. So the team in healthcare is doing both. I'll give you an example. We decided to look at a vertical because we're doing deep research all the time. We're much more research driven than other firms. A person or a team started being interested in the shipping industry. So shipping industry is a enormous industry that needs a lot more technology. So she spends two months interviews 50 people in that industry. What does she come away with? One, a new idea because realizes that there's a lack of a procurement marketplace And so we started a company in that space called Portchop and Because she was at multiple shipping conferences, which most of us have not been at she ran across the company that people were saying great things about called BoxHub, which is a marketplace for containers based in Toronto, which we never would have known about and we invested in that as well So it stems from if you know the industry and know the players and know the opportunities and know the holes You both can start companies and invest in companies My warrior with incubations and tell me I'm wrong the best founders won't want to be like a hired gun CEO to an idea that that brought in on How do you respond to my concern?

30:25Well, let's not forget the data which is that this is inside. I was one of the most successful media companies ever started MongoDB, one of the most successful databases companies that were started. Exactly another formula you just said can't work, where we started it and brought in a CEO. The question is, are you bringing in a great quality CEO and the answer is yes. And then are you insensing them correctly and making sure that it works? We've never had a CEO resign. My psychedelic company, I think, is one of the most valuable psychedelic companies started in the last four years of the United States, transcend.

30:58There's so many guilt towards a big success. Yes, these are all examples where we have done that very, very successfully. Kevin, why does so many in Cubase fail? Why you succeeded? So one, in some cases, they've tried to do too many companies and just tried to crank it out. Second is a level of execution. You've got to have money and expertise and credibility. That CEO comes in, is going to be sitting there thinking, yeah, I could maybe start my own company. One, I have to love this idea. Two, I have to feel like you've done a lot of research and a way up to speed. three, I've got to feel like you're going to add value.

31:31And so hopefully some of these people are like, you know what, Kevin and the team have a lot of experience, have had a lot of success, can help me and increase the odds of my company working. The vast majority of companies that people start don't work, our hit ratio is much higher than your average entrepreneur's, and we give people plenty of equity so that they are incentive, but it's still not easy. I mean, we don't have 100 % success rate. On the too many, how many do you like to do them? What's the right amount for you? So it's bottoms up, but we historically last couple years, we're doing summer between six and eight companies a year, but we have multiple industry groups and multiple people.

32:05So at any one time people here, one person can be working on one idea or one research project. How do you do resource allocation between new projects and you have to be efficient with financing, cut it, inject more when there's milestones hit? How do you think about efficient resource allocation between those projects? Look, that's just a judgment call because you're you're looking at very different ideas. Sometimes we do, we just did two or three months on a FinTech idea and just didn't get conviction. And so we're not gonna do it. But that's a judgment call at the end of the day. You just get to the point where you're like, I know this is gonna work.

32:40And I wanted to vote the next five years of my life to join this. And sometimes you get it right and sometimes you don't. Do you think you pulled a rip cord soon enough on the ones you do quit? When we start a company, we don't bail out on the company. But we put a million and a half dollars in, we hire a CEO if we've made the decision to go forward. Now, then the market decides because nine months later, they're going to go out to raise money. And I would say four out of five times they go out and successfully raise around and someone has an outside lead investor. And once in a while, the market's like, no, we hate your company.

33:13So that's what determines it. As that ever happened and you've gone, I disagree with the market. I'm going to keep putting money in. I get to think at one time where what we'll do sometimes is do a bridge round and we'll say you know We just need six more months because we'll have a launch we'll have customers things like that We have more confidence in the market and then sometimes there we were right and then sometimes there we were wrong How much have you invested before this structure of your own? This is a lot of yeah 250 million have you told your wife? Then why, you know, a girl group got you a lot of bonus points did you find?

33:48No, look, I, you know, I've devoted my career to this sector and so our returns have been been extraordinary. Things have worked. There's nothing more fun in life than going after a new area. Psychedelic being an example. Super interesting ahead of the curve, starting companies, investing companies and then seeing it work. And I've done that for a long time and really, you really enjoy it? How do the deal structures that you mentioned a million and a half that, is there a standard deal structure? Or does it depend on a per company basis? Roughly the team and CEO are probably going to get around 40 -45 % of the company.

34:22We will have the rest because we came up with the idea, put in the money, did all the work, and everyone gets paid from day one. So order of magnitude is going to be there. Why do you invest as well? And what I mean by that is, like your ownership when you invest on a good thing is like 50, I'm guessing about running investors. 15 would be good. When you have 50 or 60 in the incubations, is it an efficient use of capital to be an investor? It is because one is I said earlier, the time you spend learning in industry gives you an advantage in investing. Secondly, you actually can't invest that much money in incubations.

34:59If you and I started company tomorrow, and we build a seven person team to build this, I mean, that's a million and a half dollars. And I don't have enough ideas. is I wouldn't be able to come up with 30 ideas a year. So you've already done the work in a sector, you find out about incredible opportunities, you're seeing deal flow. I mean, is a year long enough? I'm sorry, I didn't mean to interrupt you, but if you think about bringing a team together, maybe take three months to hire people, three months to ramp them. Gosh, that's six months of execution. That's not very much. Yeah, and then at that point, depending on the company, often we're able to raise money outside, but often we put in another million and buy ourselves another six months or nine months.

35:36Ideally, the product is out. Some companies are using it. You can sense that it works. You've got a sense for pricing. Now we're just going to debate how big an opportunity is. Tell me, how do you think about price? I'm intrigued. You've invested in so many businesses now. Peter Fountain once said to me, price is a mental trap. How do you think about price in your own price sensitivity? Here's the thing that I don't think about, which is our ownership. Meaning, if you were going to buy a piece of an apartment, and you said, I really want to own 10 % of this apartment. Does that mean, and you have a certain amount of money, that means you're just never gonna buy a really good apartment because the price is higher.

36:11So if I see three startups that just started six months ago, one of them has an incredible team going after an incredible market. That company is worth more than the other ones. And if I put a million dollars in, I'm gonna get less of that company. And that doesn't mean it's a worse investment. But then the day you're just trying to figure out, is this gonna work or not? Sometimes we're paying a big price, and we're paying a big price because it's an incredible team and an incredible opportunity. I also worry about the addition. I've had quite a few investments which ended up being amazing, but because of the capital that went in, you got like a three or four acts tonight.

36:43No, but that's just another factor. You should factor in how much delusion you're going to take. What are the gross margins going to be? Super capital intensive businesses are going to be worse investments than ones that take very little capital. On the other hand, if you do present a to continue my example, a great founder in a big business in a very capital -efficient industry. Yes, that's actually worth more than the opposite. I agree. It's why I love low -competition markets. Like you said there, about shipping. I love shipping, too. Because they want many great entrepreneurs out of Stanford or Harvard or you name your rating.

37:17Go, oh, I'm going to innovate in shipping. They all go, I'm going to innovate in payments or in B2B. So the non -sexy areas, we just invested in a company that is creating software to manage the food, the meals in a hospital. So there's a thousand different people in the hospital staying overnight. One has a peninology, one is kosher, it's super complicated. You have to have a piece of software to manage that. There are very, very old systems. This is sort of thing you and I would never think about. These entrepreneurs came in that created a much better product. Starting to close hospital deals, it's a huge sector.

37:51Hospitals pay $150 ,000 for this software. and we're like, that's a great good team, good market. That was really interesting. And in the US, you obviously have a lot more private hospitals because you need customers who have a budget. In the UK, you sell to the NHS, which is a national. Oh yeah. You know, we don't do any healthcare outside the United States because the US healthcare market is both enormous and terrible, which is what you want when you're in hospital. Totally. Kevin, what's been your biggest miss? And what did you learn? The biggest miss is in, if I knew now what I knew then, and I would have been much more aggressive early on in starting more companies building up more of a team.

38:27Some guys who takes five to seven years to know the things are going really well. If we had sat here six years ago, I'm an investor in this crazy company in Argentina and this company called Zola, which I started, but who knows what's gonna work? Turns out a lot of these worked, and I would have actually doubled down that that was a golden age for the last decade. How do you think about ourselves financing? You mentioned, hey, we put the million and a half in. They go out, they've kept venturing. Do you double down? Do you say, hey, no reserves, signalling is dangerous? How do you think about concentration of capital?

39:01So we aren't that concentrated. So we continue to invest in our companies until probably a hundred or two hundred million dollar valuation. We generally don't put more than ten million. Might go to fifteen million in any one company. And sometimes we'll leave some money at the table and other people will take it. We want the highest return investments, and that's why we've had very good results. Because when our companies are worth a billion, we're just not investing in them at that point. And sometimes that would have been a good idea, but sometimes it's so. The other challenge that I find is selling and when to sell.

39:33Yeah. What have been some big lessons for you in actually liquidity management and when to sell? Look, the biggest challenge in the last three years is that there is no liquidity. There are very few sales. But when you have an opportunity, you should take. But again, that's company specific. Like we're never open to selling Monco, no matter what, because we really thought we were building a 10 or 20 billion dollar company. We had confidence, we had conviction. I sold business insets, or not because I wanted to, because we were doing 40 million in revenue, and someone offered me $450 million for a media company.

40:04And so I said, yes. That's not an easy decision. It was. Yeah, I say to my CEOs, if someone makes you an offer you can't refuse, don't refuse it, take it. Three years ago, I bought the company Meetup for 10 million because we work was getting rid of it and had panicked and Covid had just started and I just sold it. It was announced in January. I sold it for seven or eight times that amount because there was a buyer who wanted to buy it and the company's making now a lot of money where it had lost 20 million dollars the year before I got it. What did you use? I'm just fascinated on that one. So Meetup you buy for like 10.

40:37It was with dress sale from like a distress seller at the time you just want to get rid. Did you do much to the asset or was it just a unique buying opportunity? So both it was a unique buying opportunity. No one would touch the company because COVID just started and you couldn't meet the CEO. Who buys a company when you can't meet the management team? No one except that the CEO David Seagull who was incredible worked for me at double click 20 years before. So I knew him and he had been reaching out to me asking about the business in the six months before just as a mentor. And finally he said, and they're panicking, I don't know, I think they're gonna shut it down or give it away.

41:15I said, wait a second, why don't I buy it? So I got one or two other investors bought it, but we also went from 130 people today, I bought it to 90 people a week later, which is the right amount. Today it has probably 80, when we sold it, it had 82 people and it went from a $20 million loss on 32 million in revenue when we were going to it the year before, to now we're making five or six million dollars in profits. It's a great business. So David did a great job. Team was good. We ran it well. That's not the normal thing we do. It was just a one -off situation. It was a brand I knew based in New York, and I knew David, so it made sense.

41:51Can I see we had some of those amazing successes. What's been your biggest loss? Which one's the one that was the most expansive in Cossi? You lost the most money. It's not about losing so much money is that, you know, in 2000, I had probably a hundred million dollars worth of double -deck stock on paper, which ended up being 10 million. We were a year away from going public at Kilt, where Goldman Sachs said, Kevin, you've got about $165 million and feeling really good about this, and that ended up being 10 million. So things evaporated along the way, even if they were paper gains, but you think that they're gonna exist.

42:29And so that happens. Could you have sold them? No, the guilt I couldn't have, and I did sell all the shares I could at Dulfik, in 2000. So I couldn't have but still it's disappointing when you see 90 % of the company you're focused on the value of evaporate. But you know, and my week every day we have 130 companies. Something's going wrong somewhere in the portfolio. I get to give another company that I thought I had a $50 million position and right now my guess is I'm gonna, you know, end up getting very little or getting my money back. But on the other hand, there are big gains. That's the game we play.

43:03Do you care about loss ratio? I mean, the long term you do, but it is what it is. But the truth is, honestly, Kevin, like, if you only ever had Mongo, the outliers are so disproportionately large, they really are. Yes. Nothing else matters. Nothing else matters. So, you know, you should be doing this business because you love doing. And you find it exciting, you like helping entrepreneurs, you like coming up with new ideas, creating new categories. That's what's fun about it. And then if you do it well, you're probably financially in our business going to do very well. But I don't think about that day to day.

43:36And we don't talk about that internally. We talk about we are building companies. If we build good companies, everything will work out fine financially. Doug Leone said recently to me that we have turned from a high boutique, high margin industry to a low margin commoditized industry. Do you agree with that transition statement? No. What is true is that when you are a late stage investor writing 50 million R checks that you are what we used to call private equity. You're competing on price, there's already an established board, you're not adding that much value, it's just a different world. It's changed so much when Apple went public, when they went public, they raised $9 million in the IPO.

44:18So it's very different today. In the early stage business that you didn't square ventures does, that we do the first check -in, that's not a commodity You have huge wins, you have some bunch of losses, and by the way, I was on the board of Yale and on the board of the Yale endowment. So we were the lead investor in many of the best firms. And as you know, in V .C., there is a huge difference between returns that let's say a benchmark and a greylock half and I'll 90 % of the rest of the industry. 100 % my fear is we've just seen multi stage firms commoditized seed so efficiently that everyone has a seed strategy.

44:57I'm always asked by L .P. It's like which funds on the west coast should we do because you meet everyone Harry and on my honesty Sequoia and Dresden just come in and bid up every great round at seed you might as well just bins for an under recent No, we don't see in the last you know 20 seed deals They're not in there very often. They don't have the coverage of the two million R checks. And also a lot of entrepreneurs are very nervous about taking their money. On the west coast, people just take their money regardless. But here's the risk. If a huge fund puts a million dollars into your initial round, and if they don't lead the next round, your company's dead.

45:34Whereas if a seed investor invests in your first round, it's understood that you're going to go out to someone else. But the negative signalling that occurs, and it's happened to me. I had a big, big, big firm joined in. Everyone was very excited. And then they lost faith partly because the guy who invested in our company left the firm. And they're like, ah, we don't really, we're not really into that. We're gonna pass. And then the company was dead. Dude, getting orphaned is the worst thing in a portfolio. I can't really agree. But the chat, so I'm with you 1 ,000%. But I always get multi -stage investors push back on me, obviously.

46:06Everyone has to defend their corner. But they say, oh, rubbish Harry. Every round gets preempted today. And of course index does not cool up Sequoia who've done the pre -seed or the seed and say, oh, you're going to do the A. And so the signaling doesn't exist because of the prominence of preemption rounds. I think you're being misled by the 10 supposed hottest deals who get preempted. That's not where the industry is. The vast majority of things are not being preempted. They're going out, they're raising good rounds. They take a couple years to be really, really big. That's the meat of the industry.

46:41Do you think Vansha is more competitive than they ever been? Yes. Look, the reason one should be concerned about Vansha today is that there's probably four times as much money in funds today as there was in 2017. And the question is, are there four times as many opportunities? And I don't think there are. I think it's shifted. There's more opportunities in AI, but frankly, far fewer opportunities in e -commerce and media as we discuss. I think there's actually even fewer opportunities in straight enterprise software. You know, just Bank of America need new software products this year that they didn't buy last year.

47:15They've already purchased a lot. I think there's just a bubble of money. There's more money than the industry needs. As we discussed later, they'll spread it out. And unlike in the hedge fund industry, our money doesn't leave very easily. It takes a long time. It's ticked. Now, you'll see Tiger, which had a fund that was whatever 100 and now is now 50. So you'll see new funds being smaller, but that takes time to work through the system. You worried about the liquidity? Yeah, I'm looking at M &A markets thinking, fuck. Yeah, I don't think IPO market is going to open in 24. I know we've just seen Rubric grow out, but I think it's one of few for sure.

47:49Are you worried about the liquidity and how do you think about that? Yeah, I do worry about it, and there's nothing any of us can do about it. It makes no sense to be that you just can't take a company poll. Even though your numbers are 70, better than 70 % of all public -e -traded companies that are already public, and yet the banks and everyone will be like, yeah, yeah, you can't go public. There's no opening for that. It's just closed. It'll be as if you're selling your apartment in New York City and it was like, no, no, sorry. No apartments are gonna be sold for the next two years. Well, so I have so many VCs on the show who say like, ah, it's complete rubbish.

48:20How you can always take a company public, you just might have to change your perspective on the price that you're willing to go out of that. That is wrong. If your company's growing at 60 % and profitable, Well, yes, you can always go public. But at the margin, it is not easy to take companies public. There's not a lot of appetite. Many, many companies that be very happy to be public. And they're not because they either can't do it. Somehow we just have not opened that up. For 15 years, I've wanted to solve this problem that we need a way for companies that are $100 million and growing at 20 % to be able to go public.

48:52And that doesn't exist. What are the main reasons why companies plateau? Because you see quite a lot of companies is it 40 to 60 million in revenue? They're sitting on a billion, a billion, a half valuations, and you're looking at them going, it's probably 500. What, why does that happen? What do you think what happens to them? So one, if they've plateaued their growth, they're not worth 500. 10 times revenue for a company that's not growing that much is not gonna fly in today's market. That company's worth 200 if they're starting to be quite profitable. But that's normal. You should expect that out of every hundred companies that start 20, you got a business after two years, a certain percentage get to 10, 20, 30 million, a smaller percentage get to 50, a smaller percentage get to 100, it just keeps funneling down.

49:33That's normal. Not every market is a trillion dollar market and not every product is going to get 30 % of its market. You've mentioned some incredible wins and accumulated personal wealth. I have a lot of founders on the show who talk about challenges with their relationships and money. How has your relationship to money changed over time? So actually, you know, surprisingly little, I don't focus it on that much. Five years ago, the only car I owned was a used minibam. I'm not that into stuff. I am into experiences, so great travel, things like that. I'm absolutely willing to spend money on. But, no, I mean, it's been a long time for me that I haven't had to worry about money, but I also just don't spend money to spend money.

50:15And so I don't have any problem with it all. I have no concern about the relationship with money. Some people are so focused on money that once they made money they didn't know what to do for me that change nothing I enjoy what I'm doing when people ask me sometimes I'm at a call a business school They'll say why are you still doing this and my answer is does anyone ask a really good NBA player who's 32 and who's made a ton of money Why are you still playing basketball? Why don't you reach higher like no one would ask that question right because he would say Yes, they do pay me a lot of money, but I love what I'm doing and I can't think of anything else I'd rather do so I'm gonna do it as long as I can and then eventually it'll end and I'll do something else and That's exactly how I final final one for the quick fire has me lived up to the hype and what like Europe has not if we're blunt and people say New York Has neither so Europe you so New York City has so outperformed the Expectations people have already forgotten so in 1996 the number one question I got running double click was why aren't you in Boston Boston is the tech center you're giving me your complex look because you can't even remember that I was born in 96 Kevin that you know deck and Wang had been in Boston and so it was known as the tech city and when we went public we couldn't even find a lawyer in New York City that had ever taken a company public and I said this at the time but if you had said wait a second Kevin what do you think that if 25 years from now is There are chances that there'll be more tech jobs in New York than in San Francisco, and that we are now some quarters competing for the amount of money.

51:48You would have said, some sorry, that's impossible to imagine. And so New York has grown faster than any other city. It still doesn't have as many big wins in San Francisco, but don't forget, the big wins are from 15 years ago. We talked about Mongo and DataDog. They started in 2007. So what we're trying to say is right now, are more and more smart people starting companies in New York. absolutely are there five times as many venture capital firms we hardly had any VC money when I went out to raise money in Silicon Valley in 97 they said we will not invest in you unless you move to San Francisco's we weren't willing to do today every one of those firms that turned me down for that reason has an office in New York City so that's the trend line so yeah New York is killing it and what will be the number one company clearly 15 years or another 10 $1 billion companies all that, but data, dog, and monga.

52:38So Etsy is in the same category. Give you some context. Five years ago, it was not one publicly traded company in New York City startup that was worth more than three, though. Now we have two at 25 or 30, one at 10 more on the way. So these things take time. But yeah, I mean, I was just in the Google office and 15 ,000 people in New York City. And I remember 20 years ago, people saying, oh, but there's no tech talent in New York. You can't you can't start an enterprise software company here, but somehow they found 15 ,000 people. Do you worry about the centralization of AI talent in San Francisco?

53:11No, I think services absolutely has an advantage in AI. It stems from the fact that, you know, I just started company in material science AI and the university that dominates that space is Berkeley. And so Berkeley and Stanford are stronger than New York, than Columbia and NYU, and they've had companies and deep talent. So absolutely San Francisco has an advantage in that area. But we're seeing, you know, 10 companies a week starting in New York, they're starting all over this country. Many of the smartest people are doing AI, and it will distribute more. When I was tell people what I'm traveling internationally and they used to ask me, which cities are gonna dominate in your country?

53:53It has nothing to do with tax policy, has nothing to do with anything. I say people who went to the top 20 universities in your country, where do they want to live? Where are they going to move? That's going to be your tech center. And guess what? That number one place those places people want to move is New York City. San Francisco is still a great place and history and many things going for it. So it's an amazing incredible place. But I'm not seeing the tech town on in Miami, and I don't think it's going to get there. I'm not seeing in Chicago. You know, don't forget 15 years ago, the number one Internet company on the East Coast was AOL based in DC.

54:25is DC, the tech hub that New York City is not at all. That's super smart people from Harvard, Yale, Princeton, MIT. They want to live in New York City. I could talk to you all day, Kevin. I am mindful of time. So I want to move into a quick fire answer. I say a short statement. You give me your immediate thoughts. Does that sound OK? Sure. Slightly weird and out there one. What's the secret to a very happy marriage? First of all, it's putting the time in and the commitment. I've been married for 32 years. It's friendship at the core and a common purpose of hopefully if you're doing it raising kids.

54:59And we've been very lucky. I have three kids in our 20s. It's a big part of our lives. It's been a days. How do you bring children up with such financial success to be humble and also of working and ambitious? Yeah. You have to install that from day one and understand and treat them that way too. I was with friends of mine and they said maybe I shouldn't have given my 18 -year -old a $75 ,000 Porsche. And I'm like, yeah, of course you shouldn't. My kids don't have any of that. They graduate from college. They have to make it on their own. They hopefully go to good schools. They you're installing that from day one.

55:35Tell me, what have you changed your mind on most in the last 12 months? You know, I thought there was a game you worked more recession. Other than that, you know, my opinions don't change dramatically because I really have to have this 10 year perspective as I was saying earlier. So it doesn't change day to day. my industry focus things like that. Why do you think that will not be such a big recession that you thought would happen? The combination of the fiscal stimulus with the Biden administration has done, which doesn't get credit for, combined with the Federal Reserve, has been remarkable management.

56:08I read the French press and they talk about Bidenomics and how do we compete with it? Can we compete with it? Because it's so effective and our French companies are setting up factories in the United States and creating jobs. I think it's been remarkable management between those two. There's not a single economy so I thought it was going to happen. Will Trump win? Either way, it's me 50 -50. I think Biden's going to win, but it's actually going to end up being out of our hands. Either one of them has a huge health issue. That could do it. If there is a something happening from geopolitical point of view that goes horribly wrong, that could change it.

56:40I think that the substance and the success of the economy at the end of the day combine with the fact that the Democrats are winning every single election that is occurring across this country and outperforming since the Roe v. Wade decisions means that at the margin the Democrats are going to. What's the biggest piece of startup advice that you think most BS? Like the most commonly said, you're like, oh, I can't believe this is still a trope. You know, move fast. Yes, but if your product sucks, that's not good. So startups and business are a series of decisions and compromises that are situation specific.

57:18That's where judgment is important. And that's where I do think investors and good CEOs play the role. What's the luckiest thing that's that'll happen to you? Oh, by far, financially it was working with two other co -founders and starting Mongo. Is that luck? Well, look, I had it was my CTO. I was a CEO of Double Click and the CTO and I wanted to start, we'd started companies together. We had started one or two that didn't work and then we started Mongo. ago, but the intellectual and execution of Mongo came more from them than from they built the product. I benefited even more than I deserve to, you know, making the decision to get involved with the internet in 96, which, you know, I thought was going to do well, but, you know, I've had other thoughts over time that I thought we're going to do well and they didn't.

58:03And that changed my life and my career. What do you know now that you wish you'd known the day you started investing? The judgment of seeing many things work and not work is helping makes you more decisive on just feeling like, you know I'm just not feeling it and trusting probably my gut feel a little bit more. It just doesn't feel right It doesn't feel right. Penultimate one. What are you most concerned about in the world today? Trump. For me, the single thing I'm worried about, I'm actually the world from a safety and security point of view is actually okay I'm obviously very biased on this.

58:33The single thing that I'm concerned about is Trump winning on multiple dimensions giving away Ukraine Supreme Court justices, very, very, very poor execution of every aspect of government, a level of corruption that I think would follow. That's the single thing that worries me the most. I think the thing that worries me the most is we've seen the normalization of corruption across so much of government, but we're almost not surprised anymore. So I don't agree. I don't think there's a single example in the cabinet of Biden after four years that you can point to, where we could point and say, I think that's actual corruption.

59:08I suggest you look at the UK government. I'm sorry, I'm not commenting on the UK. You're absolutely right with the Biden administration. In the UK, we've had some very interesting decisions made on a lot of different. That's a whole other conversation that we should talk about. But from a corruption point of view, with the benefit of hindsight, the Obama administration was extremely clean. And the Biden administration has been extremely clean. I'm not saying that they all did everything right in their policies, but from a corruption point of view, I don't argue that either White House had a problem.

59:43What was the most corrupt of the Trump administration? Well, I mean, there's 15 people that have been convicted of crimes that work there. The National Security Advisor was convicted. So many people have been convicted in that administration and are serving time. There's many people in shape. Final one for you, Kevin. When you think about the 10 to 20 year time horizon for you and for the funds now. What does that look like? The business wherein does not scale infinitely, we're not trying to accumulate assets. So I don't want to be a $2 billion fund. I want to continue doing what we're doing. We may go bigger in some areas.

1:00:22Like we have a deep tech practice. I'd like that to get bigger over the next couple of years. So next time we raise a fund, if we could, I might increase the size a little bit just to increase verticals. But we're going to continue doing what we're doing. and look, I lead my life because I want to be enjoying it, having fun, you know, doing athletic pursuits, going to Burning Man, making great investments, helping a bunch of Benures, spending a lot of time with my kids, you know, out there having fun. Kevin, I've loved this. Thank you so much for doing it. Thank you so much for sharing. So many of the lessons learned and you've been fantastic.

1:00:54That was great to do this. It was a great conversation. I have to say, for me, the joy of doing the show is discussions like that. One's where you can really learn from many, many years of incredible wisdom and experience. I want to say huge thank you to Kevin for being such a fantastic guest there. You can check out the full video on YouTube by searching for 20 VC. We was loved to hear your thoughts there. But before we leave you today, Koolie, the global law firm, built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Koolie has formed more venture capital funds than any other law firm in the world, with 60 plus years working with VCs.

1:01:27They help VCs form and manage funds, make investments, and handle the myriad issues that arise through a fun's lifetime. We use them at 20 VC and have loved working with their teams in the US, London and Asia over the last few years. So to learn more about the number one most active law firm representing VC backed companies going public, head over to coole .com and also coolego .com, coolees award -winning free legal resource for entrepreneurs, and speak here of providing incredible value to your customers. Travel on the expense and never are associated with cost savings, but now you can reduce costs up to 30 % and actually reward your employees.

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1:03:29As always I so appreciate the incredible support and we have an incredible show on Friday, a 20 sales episode with the one and only Sam Blonde, one of the OGs of sales.