How Sequoia’s Bogomil Balkansky Identifies Outlier Founders

0:00When in times of great disruption, it's usually not necessarily like the first companies that blaze the trail that end up having the staying power.

0:13Peter High: Welcome to TechnoVenture. I'm Peter High, president of Metastrategy. My guest today is Bogomil Balkansky. Bogomil has been a partner at Sequoia Capital for the past six and a half years. Founded in 1972, Sequoia is one of the world's most storied venture capital firms, helping shape multiple generations of innovation. At Sequoia, Bogomil focuses on early-stage enterprise technology investments with particular emphasis on AI, cloud infrastructure, cybersecurity, developer tools, and enterprise software. Before joining Sequoia, he spent more than two decades as an operator, including executive leadership roles at VMware, where he helped scale its cloud infrastructure business during a period of extraordinary growth, and at Google Cloud, following Google's acquisition of Bebop, an enterprise cloud startup where he was an early executive.

0:57Peter High: Earlier in his career, he held leadership roles at Siebel Systems and began his career as a consultant at McKinsey & Company in Germany. In today's conversation, we'll discuss what Bogomil looks for in exceptional founders, how AI is reshaping enterprise software and infrastructure, why the best companies often emerge during periods of disruption, and how his years as an operator continue to influence the way he invests, among other topics I'm sure we'll cover together. Bogomil, welcome to Tech Inventure. It's great to speak with you today. Pleasure. Pleasure to be here. Thank you so much. I've been looking forward to this conversation.

1:27Peter High: I wanted to begin, if you don't mind, Bogomil, with some of your experience that I just referenced prior to your time at Sequoia. You spent the period of 2005 to 2013 in VMware. where I mentioned that a moment ago, helping the company scale from$400 million per year to$5 billion per year in revenue as a senior vice president of cloud infrastructure products. Talk a bit about that experience. And I'd be curious about how it helps you counsel your portfolio companies today about scaling their businesses. You've experienced what they aspire to. And I wonder how that influences your role as an investor and advisor.

2:03Yeah. Well, Peter, first of all, let me say that I'm very, very careful not to start every other sentence talking to my founders with, when I was at VMware, like, you know, this and this happened, A, I think it will be like utterly annoying to founders. And B, it has been like more than a decade since I left VMware. And one has to recognize that history rhymes, but doesn't repeat itself. And every company has a unique set of circumstance. And you can just mechanically translate lessons learned from one era, one environment into like a different company. So I'm very careful about that. But having said that, of course, we are all made up of the collection of our life experiences.

2:49And I can't help but bring some of these learnings from my VMware days into my work with portfolio companies. And a few things stand out now with the benefit of more than a decade of distance from the VMware experience. The first one is the courage to dream really big. When I joined VMware in the fall of 2005 as a director of product marketing, literally the very first thing I was asked to do is to put together a go-to-market plan for VMware for the next three years, like 2005 to 2008. And I distinctly remember how the boldest ambition that I could think of, how big VMware could get within the span of three years was to grow from 5 ,000 customers, which was the starting point at the time, to like 20 ,000 customers.

3:45And it was like pages and pages of my plan of like, oh, all the things that need to line up to get to 20 ,000 customers. And guess what happened actually in 2008? We had gotten to 120 ,000 customers. So the reality exceeded my boldest projection by 6x. And of course, honestly, sitting back there in 2005, I probably would have been laughed out of the room at VMware if I said, oh, you should get to 100 ,000 customers. But this is just such a visceral reminder for me that you always need to push your assumptions and always need to ask your questions of what are the real constraints to growth? And the constraints to growth, are they real?

4:32Are they imaginary? And I always try to push the founders that I work with to think that way. But what if things go right for us? What's really in the way of us growing 5x, 10x in the next year? And having these conversations is not so helpful to put concrete plans together, but very helpful to liberate your own thinking, to kind of like unshackle your own thinking, because the natural human reaction is towards incrementalism, right? Like, you know, 5 % improvement, 10 % improvement. Oh, you know, if we double, that will be amazing, right? You know, et cetera. But what if you can like grow 10x?

5:16So it is one valuable lessons that I take away from these days. And the second one is the power of an amazing product. VMware wasn't just a product. It was a movement. And it was just such a beloved product that our users, I mean, they swore by it. They told everybody how great the product was. At our customer shows called VMworld, we'll get these standing ovations. Like when we make the new product announcements and you literally have this enormous room in the Moscone of 20 ,000 people getting up from their chairs and clapping. And the true magic really happens when you have a product that's amazing, that hits a nerve, that solves a real here on the fire, here today problem.

6:17Then you get to this explosion. And the lesson for me there was that, A, you can never push your way into an amazing growth. The only way to orchestrate amazing growth is you need to have an amazing product and you need to hit the nerve on the market. You need to hit the right problem at the right time. And one of my observations from the companies that I work with at VMware is that the companies that really are setting the mark in terms of how quickly you can grow, So what is common across them is that they never had the sales capacity. They never had all the infrastructure to orchestrate that growth.

7:07They shouldn't have been able to achieve that growth, but yet they did. And the only way that happens is if literally customers are taking your product out of your hands, despite your inability to serve them well. And so the power of an amazing product is another lesson. And if you can bear with me for one more, a third one would be the power of an ecosystem. VMware was a very channel-driven company. Something like 92 % of our bookings actually came through channel partners. and we had this vast network of channel partners, something like 22 ,000 of them, 22 ,000 partners, which basically meant that we had hundreds of thousands of people who were reselling VMware products and the leverage that you get from that kind of ecosystem is tremendous.

8:10You literally have hundreds of thousands of people whose livelihoods depend on VMware and they're rooting for your success. And guess what? It's a lot more powerful to have quote-unquote independent people who are selling not only your product, but they're selling like a bunch of other products, like vouch for your product and tell customers, you know what, we should buy this one. You know, this one is the good one. As opposed to your own salespeople, like, you know, knocking on doors and selling products. And of course, like, you know, that was somewhat of an expensive model in the sense that, you know, half of the revenue generated from end customers actually stayed with the channel.

8:53Like what came to VMware was like roughly 50 % of what customers paid. But again, like the leverage that you get from a partner ecosystem is amazing. And if you can get other people, other companies, other entities to be really vested in your success, this kind of ecosystem really pays dividends over decades. And it's not trivial. It's very hard to build. It's very hard to get thousands of people to be rooting for you and to be part of your ecosystem. But if you're lucky enough and capable enough to get it, it's a tremendously powerful thing.

9:35Peter High: I can, Peter, I can go on and on and on, but let me pause there. That's fantastic insights all. And I wonder, you would follow VMware co-founder Diane Green to Bebop. So you went from a company that when you joined was already a consequential organization, $400 million in revenue, to one that was much smaller. And I wonder, to what extent did you have an immediate opportunity then to think further about what you just described and need to hit a nerve with an amazing product and the development of a partner ecosystem? How did you begin to apply those same lessons into a startup scenario that you joined with Bebop?

10:11I mean, indeed, I did join the young green, like the founder and original CEO of the company to a startup that she founded in 2013. And honestly, in my case, it was such a joy to downscale from running 160 person team at a company of 16 ,000 people to a team of six. where literally you show up on day one and you literally, you have to put together your desk. Here's like a hammer and like, you know, whatever. It's like, Diane really believed in the notion of scrappiness and, you know, we could have raised money like very early on, but we didn't on purpose. We didn't raise venture money until ironically, two months before we got acquired by Google.

11:04And so we ran that company for more than two years, really on a shoestring budget. And because there's no substitute for the startup pain and grind, and we have to earn it, we have to deserve it. And one of the lessons that I learned from Diane in those days is, yes, you can easily raise money, but that's not the point. Money doesn't make you a great company. The grind is the thing that can make you a good company. Another thing that really sticks in my mind from the many conversations with Diane at Bebop was, as a startup, you have no choice, but you just need to make a bet on yourself. I mean, you've got nothing else.

11:54You don't have any resources. You don't have a brand name. You don't have a product yet. And so the only thing that you can believe in, the only thing that you hang your hat on is yourself and your capability. And you need to believe that you're going to make it. And you have what it takes to fight on the market. And so, you know, these first couple of years of the bebop journey were so blissful for me. My husband was even making fun of me in these early days of bebop. He was telling me how I was like a first grade student with my little lunchbox, like whistling, like on my way to school, like, you know, every morning.

12:41I was so happy in these early days of a startup. And part of my happiness probably came from... The reason I enjoyed the downshifting so much is that the VMware had reached a scale of like 6 billion revenue, 16 ,000 people, that the molasses of a large company just made everything so sticky and so immobile. And the effort required to affect a change this small seemed that big. And it's just like, it seemed like so out of whack. Boy, I'm tired. Like, you know, I'm tired of pushing to do something that small. And it was really liberating to downshift to a company of six people. So that was the joy of the startup.

13:40On the flip side, boy, of course, like any startup, we made a whole bunch of mistakes. One of them, trying to bite off more than we could chew, so to speak. And yes, on one hand, you always need to make a bet on yourself. but we probably went too far. We were trying to build this platform and in retrospect, we should have started with building something smaller that we can put in hands of customers and start generating momentum and start getting escape velocity and eventually build towards a platform. And nowadays, when I meet with startups and somebody tells me we're building a platform, I honestly roll my eyes and my answer is like, no, you're not.

14:35Maybe if you're lucky, in five years, you earned the right to call yourself a platform, but right now you're not. And it's built something that may seem tactical and small today, but that is the path of a startup. Just get some momentum, get some escape velocity, and then build towards a platform. Obviously, as a founder, you always want to be dreaming big, but you really need to be very careful how you sequence your execution such that you don't bite off more than you can chew. In our case, it was two years to build this product before we can actually launch it on the market. And that is too long to be in stealth mode and not to be getting real feedback from the market.

15:32Some of the startup pains.

15:36Peter High: Yeah. Thank you so much for those reflections. Well, let's fast forward to Sequoia. You joined the firm. A fellow grad student at Stanford, GSB, was roll up both Carl Eschenbach, a former colleague at VMware. where both of them were already partners at Sequoia. They provided at least a part of the rationale for you to join the firm, no doubt. You've described yourself now as an investor, as somebody who is more of a feeler, who invests on intuition rather than, say, spreadsheet analysis. I'm sure you do some of that too. But talk a bit about what you're feeling for as you evaluate entrepreneurs, Bogomil.

16:11I mean, first of all, I have to tell you kind of a funny anecdote where this feeler thing actually came from. So way back when, before business school, I started my career at McKinsey. And at the time, during the business analyst training program, McKinsey would march each cohort of new recruits for the Myers-Briggs test. And my training was taking place in England, like in some place. And literally in front of this entire cohort of new recruits, the person who was moderating this entire exercise stood up and said, like, well, you must be a hiring mistake pointing at me. Because you're unlike what McKinsey looks for.

16:51You're a feeler, not a thinker. And I forgot my other designation was, but literally, she called me out as like I was a hiring mistake. And maybe that's what kind of influenced me to think of myself, oh, I'm a feeler, I guess. I embraced it. I went with it. I believe that everybody needs to figure out for themselves how they make good type one decisions. Type one decisions are the one that are one-way door. Either the completely irreversible decisions or very difficult, like to unwind and reverse. And that takes some amount of life experience and self-inspection. And honestly, I don't think there is one side fits all.

17:43We're all different people. I think each one of us needs to figure out how when presented with a significant decision like that how how do we make like best decisions and in my case over the years i concluded that the best way i make type 1 decisions is if i follow my gut now what does it mean like to follow your gut like what what do we mean i mean it's like such a popular special foliar guy like what does it what does that mean and my very non-scientific explanation of following your gut is that But it's really the amalgamation and the culmination of all sorts of subtle signals that you have been getting from people, from reading, from listening.

18:29And you don't necessarily pay conscious attention to each one of these micro signals that you're getting, but they kind of amount to this gut feeling that, hey, A is the right way to go, not B. and again in my case I've concluded over the years that if I follow my gut more often than not I'm happy with the decision that I made in retrospect and the way I get myself in trouble is if I force myself to be overly cerebral about these type one decisions like you know to play these games that people tell you oh write down the pros and cons on a sheet of paper like in two columns, I'll create a spreadsheet, then I get myself into trouble.

19:16And usually the nature of these type one decisions is that there is no perfect information, or there's not enough information. Because if there was enough information and data, yeah, put it in a spreadsheet and I'll be like the answer, but usually that's not what that decision is about. And so I've become very comfortable of listening to my guts and making those types of decisions that way. And early stage investing is about type 1 decisions. Once you pull a trigger and you partner with a founder, it's not completely a reversible decision, but in most situations, it's difficult to unwind and it's kind of a one-way door and you're going to be with that person or that team for the better part of a decade.

20:10And I think in my case, I've learned that this is how I make good type one decisions. And I think the other thing about early stage investing is that there is no data. I mean, we would partner with companies at the proverbial two people at an idea stage, there is no product. Very often the best investments are markets that don't yet exist. I mean, this is going to be the company that will create the market. And so there's no Gartner report about the market size or anything like that. So there is no data to help you make that decision. And then what do you rely on? You rely on your judgment of who these founders are, what they're made of, what their values are.

21:03Are they truly exceptional? Or in sequoia parlance, are they outliers? And by the way, there's not a single mold or a single recipe of what makes somebody an outlier. There are multiple characteristics that can make you an outlier. Some outlier founders are the math Olympiad winners or IQ of 180. Some outlier founders have an unusual amount of grit and perseverance and stubbornness, if you want. Some outlier founders are fantastic storytellers, talent magnets, concentrators of talents. And some outlier founders have combinations of some of these things that I just mentioned. But our goal as early stage investors is really to figure out is this truly an outlier founder and what exactly are the outlier characteristics.

22:00And what I'm feeling for when I get a chance to meet an outlier founder is precisely focus on that. Like, you know, try to assess is this an outlier founder and what the outlier characteristics are. And then we also try to imagine, can this thing, can this idea be an amazing market? Not today, five to 10 years down the road. Because at the end of the day, market always wins. And no generational company has ever been founded by somebody who is not an outlier. But the converse is not true.

22:42Peter High: Not every outlier founder is lucky enough to build a generational company because, again, the market always wins. And sometimes the market materializes and sometimes it doesn't. And the second part of our job or the second thing that I'm feeling for is, can this thing that's in the founder's imagination be a generational business? Can this become a truly amazing, amazing market? Well, let's personify this, if you don't mind, Bogomil. You were an early investor in Wiz, which would become one of the fastest growing software companies in history. Describe what you saw in Asaf Rapoport and the company when you invested, and could you have guessed that their trajectory would be anything like what they achieved?

23:29Oh my God, this is such an amazing and somewhat funny story, actually. But first, let me be very clear that I was just in the right time at the right place. Doug Liewany was the board member at Wiz, and I was just lucky enough to shadow Doug and be a board observer at Wiz. And the way all of this happened was I started at Sequoia on January 6, 2020, right before the pandemic. And lo and behold, a week later on January 14th, the four WIS founders show up at Sequoia. And I'd never heard of them, but they're a very known entity to Sequoia because their previous company, Adalom, was funded by Sequoia Israel.

24:24Doug has spent a fair bit of time in Israel. And Doug basically had the relationship with the Wiz founders and they sought him out. And Doug tapped me on the shoulder, hey, new guy, I hear that you may be somewhat technical. Why don't you have this fabulous Israeli team? Why don't you talk to them and kind of figure out what they intend to do and write a short investment memo? And so literally the first thing I was ever asked to do at Sequoia was write this investment memo for Wiz. And the funny bit of the story is that later, we realized that this original idea that the Wiz founders pitched was totally a decoy idea.

25:16But anyway, the company at the time was called Beyond Networks. It wasn't called Wiz. And because we already had experience with Sequoia, they knew that Sequoia needs to have conviction on the team, but then also have some conviction on the market. And so two nights before they came to pitch to Sequoia, they literally came up with this idea that honestly, they don't have deep conviction on. In their minds, the sequence of events was, hey, we'll raise some money, we'll start engaging with CISOs and we'll figure out what we're actually doing. But they knew that, well, they thought they couldn't show up at Sequoia with that approach of, oh, we'll just trust us, we'll figure it out.

26:01So they came up with this decor idea and if I was to reread my investment memo, it's about something about stitching together cloud networks and on-prem networks. Like that's what's in my investment memo. So somehow, you know, we convinced ourselves that this could be a market. And so we partner with Wiz. And only a month later, in our standing check-in with them, they tell us, oh, by the way, we changed our mind. We're no longer pursuing this networking thing. And another month later, again, same story. Oh, forget about the second idea that we told you. Now we're doing cloud security. and at that point Doug and I did have a moment of like looking at each other and we're like man did we did we make a mistake here I mean these guys I mean they're supposed to be good but they're just changing their minds like you know every every month there's like every month is the flavor du jour and actually by that check-in the pandemic had already struck so we're all on zoom They're in Israel.

27:08We're all in lockdowns. And they kind of went dark on us for a few months. And they're really like heads down. Once they committed to cloud security as direction, they really went heads down and kind of resurfaced in kind of late Q3 of that year. And I remember Asaf declaring to Doug and I, we're going to close more than 2 million in that first quarter. And here are like the eight customers. And again, I have to admit that Doug and I were like, well, okay, that sounds great. I don't know if we totally believed that the company was going to get that flying start. but hey like you know over a period of six years it was one of these very very unusual stories of of everything just going up into the right like not not a bad quarter ever like not a stumbling block not a crucible moment honestly that just never happens right like you know if you look at the journey of every amazing company, it's never a straight line up and to the right.

28:22I mean, it's usually a meandering path and there's like one or multiple rounds that are tough to raise and there are crucible moments and there are ups and downs. And Wiz is kind of like this very unusual and exceptional story that literally it went up and to the right, like from day one to a spectacular exit. But sorry, that was maybe like a big digression. The original question was like, did they have the sense how exceptional these founders were on day one when I met them? Not really. Absolutely not. I mean, I'm sure Doug did, but I didn't. And I have to tell you that one of the things that took me surprisingly a long time after making the transition from being an operator into being an investor was calibrating on what an outlier founder truly looks like.

29:17And that took me by surprise. And I thought, hey, I have worked in excellent companies my entire career before I joined Sequoia. I worked at McKinsey. I worked at VMware. All the companies where I worked were concentrators of talent. And I thought, I have a pretty good mental image for what good looks like. Turns out, I didn't. Turns out that being top 10 % or top 1%, even at a company like VMware, doesn't make you an outlier and doesn't make you an outlier founder. First, there is a huge difference between being a great employee and being a founder. and honestly truthfully very often the great employees don't make good founders and a lot of outlier founders are not great employees because they're disruptive they are contrarian which makes them controversial like you know they ruffle feathers they break glass and usually that makes them like somewhat or fairly unpopular especially at large organizations.

30:33And so again, the mental image that I had from VMware and other companies of what good looks like actually was kind of irrelevant to what makes somebody an outlier founder. And it took me quite a bit of time again to internalize and really kind of build this mental image of what an outlier founder looks like. And so, you know, I certainly would be lying if I said that, boy, when I met the WizFathers, I knew it, like on day one. I mean, over time, I, you know, I'm lucky, like, to have become close friends with all of these guys. And yes, over time, I did recognize, like, the unique characteristics, but not in the beginning.

31:18Peter High: Fascinating. Really interesting reflections. Thank you for that, Bogomil. Let's stick with cybersecurity for a moment, an area of great emphasis for you. You've invested in Wiz and Sierra and Oasis and Zafron and among other leading companies in this space. You've talked about how autonomous threats require autonomous defense, which entails, among other things, security teams needing AI agents to counter automated attacks. And I'd love to have you unwind that a little bit. And concretely, what does an AI agent run security operation look like in action optimally? Yeah. I mean, cybersecurity has always been an asymmetric game, even before AI, in the sense that attackers always kind of have the leg up.

32:09Like it's very unfair, but like, you know, trying to build cyber defenses, you know, is very, very difficult. It's mission impossible. And honestly, I don't think it's even theoretically possible to build like, you know, the perfect cyber defenses because there'll always be like, you know, some vulnerability that like, you know, we haven't discovered, like there's always something that slips through the cracks. and if you're attacker you just if you're a malicious actor you just need to find one like vulnerability you need to find the one way and and you're in and if you're a defender like you are always playing this game of like whack-a-mole right like you know you patch this you patch that only to discover it over it's like you know twice as many new things and then twice as many new things, I've been twice as many new things.

33:04And it's just like, that's why it has always been kind of this asymmetric game. And I think AI is now just upping the ante by another order of magnitude because AI is a force multiplier. And unfortunately, it's also force multiplier for attackers. It just makes it so much more efficient. like, you know, to attackers are basically like the first would automate their processes, right? Like of mounting, mounting like attacks, because, you know, if you think about it, like, you know, if you're an attacker, there's only that many, you know, IP addresses you can scan in a unit of time. And maybe you can build some scripts and automations kind of old fashioned way.

33:49But, you know, like now you can create an agent that like consistently, predictably, like, you know, 24 hours a day, just looks for vulnerabilities. And so AI has really exacerbated the asymmetric nature of cyber defense. Because attackers for sure are leveraging AI, the only antidote to that is as a defender, You need to be leveraging AI because you cannot fight machine speed attacks with human speed actions. It's like a road to nowhere. And the history of cybersecurity has been kind of this model of scan your environment, find vulnerabilities, assess server exploitable, create a patch or whatever the remediation approaches and then deploy it.

34:53And that cycle tends to take weeks to months at organizations at scale. Literally, it's months between, oh, I know I have a problem somewhere before actually like deploying the solution. And that's no good, right? So, I mean, again, AI makes it so easy to exploit vulnerabilities in zero time. And so this entire model of scanning, patching is kind of a road to nowhere. And I think today, companies really need to rethink their cyber defenses and and move to a posture of secure by default. So in other words, put your time and effort in building software that doesn't have vulnerabilities rather than build something and then just start looking for what vulnerabilities it might have.

35:57And so I think this is really a wake-up call for cybersecurity. And there's a lot of talk about MIFOS and what the anthropic MIFOS model and the implications of it for cybersecurity. And listen, this is not about cry wolf and the sky is falling. I think it's just the next natural evolution of cybersecurity.

36:27Peter High: And as someone who thinks so much about this space, who has a reason to get to know so many of the people who are influencing for the good innovation in this space, How optimistic are you that, especially given some of the challenges you just described, how optimistic are you that the issues that continue to come in waves and will continue to come in waves will be counteracted by great entrepreneurs who can develop products that can withstand the waves coming in? I'm not panicked by any means. I'm actually pretty optimistic. I mean, it's like AI, of course, is a big disruption, but it's not the first disruption, the technology disruption that the world has seen.

37:22And one of the reasons cybersecurity is a great market from an investment perspective is precisely because it's evergreen. And what I mean by that is the only constant in the world of technology is change. And guess what? whatever new thing kind of emerges in the world of technology, it needs to be monitored, which is observability. It needs to be secured, which is security. And that's why observability and security are two evergreen markets that periodically produce new champions, kind of like new high market cap companies, because that constant disruption is guaranteed to create new opportunities for new companies, new champions to emerge in cybersecurity.

38:08And if you look at the history of Sequoia in the last, not even in the last 54 years, since 1972, but in the last 25, 30 years, we've been lucky to partner with a lot of the champions in cybersecurity, like Palo Alto Networks, which by the way was incubated in the Sequoia offices. And then Jim Goetz worked very, very closely like with Nir Zook on like the internet age firewall. I mean, like honestly, like if we're having this conversation 20 years ago, maybe we would have had like, oh my God, is the sky falling? Like, you know, the internet, now everything is accessible. Like, what are we going to do?

38:46And guess what? Like, you know, there's an ingenious founder, Nir Zook, who came up with kind of what at the time was the authoritative solution to the new set of problems. So I fully expect that this disruption will give rise of a new generation of security champions. And yeah, the sky is not falling.

39:09Peter High: You've mentioned a couple of times the idea, of course, AI is a big disruption, but it's not the first. And you've had a long enough career now to have surfed multiple of these waves in different ways. I wonder, how do you think about where history repeats itself versus areas where we are treading on new ground here? I forgive a broad question, but maybe the first things that come to mind as you contemplate those two vectors. One of the first things that comes to mind is that when in times of great disruption, it's usually not necessarily like the first companies that blazed the trail, that end up having the staying power.

39:51And if you look at the dawn of the internet age, I mean, the company that blazed the trail was Netscape. And that went public in 96, and by year 2000, it was gone. And the companies that ended up having the staying power, like, you know, from the internet era were not founded until like 98, 99, like, you know, and this is, you know, three, four, five years after the Netscape IPO. And obviously today we're living in the gold rush of AI. And I fully expect something similar to happen here. I fully expect that the companies that blaze a trail may or may not be the ones with the staying power. And I fully expect that there'll be the next generation of AI companies that may end up having the staying power.

41:00That's actually the first observation that comes to my mind.

41:06Peter High: I really like that. I want to also talk a bit about your background, if you don't mind, Vogelbill. You understand risk at a very personal level. You left communist Bulgaria when you were a young adult. I've always thought like the immigrants journey is itself fundamentally entrepreneurial. It's taking risk and doing so with optimism and willing to make the investments to make that work under challenging circumstances, to say the least. I wonder how does your experience through your formative years and some of those risks, if you frame them as such, if you buy that framing, how does that experience color your risk tolerance, either as somebody who was involved in startups as an operator or now as an investor in startups?

41:48Honestly, I just got lucky multiple times. The first stroke of luck was that I was the right vintage. I was born in the right year such that I finished high school. the year after the Berlin Wall fell. And so, yes, I did grow up during the communist regime in Bulgaria, but very comfortably for me, the communist regime crumbled the year before I finished high school such that when I finished high school, the world was very different. And the world suddenly opened up for me. Now, it wasn't only luck because even before the communist regime had crumbled, I had been kind of plotting how I was going to come to college in the US.

42:38I had, through friendships, and again, another random, very interesting story, I had a Chinese friend living in Bulgaria who told me how you apply to schools in the US, et cetera. So I had a little bit of information advantage. Different things were going from my mind. Maybe I should illegally cross the border between Bulgaria and Greece or Bulgaria and Yugoslavia and do it that way. But again, I didn't come to it. I ended up applying to a bunch of colleges in the US in my last year in high school in Bulgaria and was lucky enough to get a full scholarship at Cornell. And this is how I made it out of Bulgaria.

43:32But actually, a big leap from Bulgaria to the US was the second leap in my life. The earlier one was moving from my hometown in Bulgaria to the capital. So when I was 13, I got it in my head that I wanted to go to this very fancy high school in the capital in Sofia. Why? Because I had seen this television program about that fancy high school. And I had gone in my head that like, that's where I should go. That's where I belong. And my parents, again, I'm so lucky that my parents were the most supportive parents. And And, you know, it's not only that they supported me for this entire application process to the fancy school like in Sofia, but once I got accepted, they decided to approve themselves and moved together with me from my hometown to the capital, which at the time in Bulgaria was very non-trivial.

44:31you couldn't just decide, oh, I'm just going to move. In communist Bulgaria, basically, you needed kind of like, you know, this residency permit if you want. And so you couldn't just decide, I'm going to move to Sofia. And it cost my parents like a lot, kind of like try to work the system and get like, you know, these residence permits, like, you know, to move to Sofia, et cetera. But anyway, so my parents also made a bunch of sacrifices, like, you know, for me, But I would say that emancipation of moving myself from my hometown to Sofia at age 13 was maybe even a bigger step than moving myself from Bulgaria to the US when I was 19.

45:18I don't know how to explain it, but I've always had this sort of gypsy spirit, this wandering spirit that whenever I was, I was destined not to stay there. I was destined to go someplace else. My hometown, it's a lovely place, nothing wrong with it, but I always felt like, oh, I should go to high school in Sofia. And then, well, of course, the natural thing for when you finish high school in Bulgaria is you apply to university in Sofia. And somehow I thought, oh, no, I should go to school somewhere abroad. and the reason I ended up in the U.S. is simply because I had figured out the application system of how you apply to colleges in the U.S.

46:05and I didn't know how to do that in England or Germany etc. and honestly again I come from very humble background my mom was a seamstress my dad was a car mechanic and my only chance to the U.S. was to get a full scholarship. Honestly, even if I had to contribute$1 ,000 to my college expenses, that would be totally unfeasible with the hyperinflation in Bulgaria in those years. Yeah, that wandering spirit is very much alive in me and outside of work. I travel the world and swim with whales, as you know. But yes, I do believe that A, has increased my tolerance for risk. And most importantly, I think, has conditioned me to have the courage to pull the trigger.

47:10Because in this investing, being like working in venture capital, So the Sequoia ethos is to find the best outlier founders and partner with them. By definition, that means that we make very, very few investments. So I would make like two investments in a year. And if it's so rare to make an investment, you can easily kind of get yourself in the cycle of overthinking, overanalyzing. Oh, is that, is that the one, is that one of the two, like, you know, investments that I should make this year. And at some point you need the courage, like, you know, to pull the trigger, like, you know, to take the step and say yes.

47:55And I think all of these experiences, like from my youth of, you know, emancipating from my hometown then to the US, again, have helped and conditioned myself like to be bolder and like, you know, to have the courage, like to pull that trigger.

48:10Peter High: Well, something that does take courage is swimming with whales. You just alluded to that. You took more than a year off before joining Sequoia sabbatical to focus on a variety of personal passions, I know. But talk specifically about that one, which, my gosh, that seems, for me, it seems incredibly intimidating. I'm delighted to see whales. I've been on whale watches. I've never swum with them. And so I'd love to understand that a bit and what you drew from that experience. I mean, outside of work, my biggest passion is the ocean. So I'm a scuba diver, free diver, and underwater photographer. You know, it started maybe outside like, you know, 15 years ago, first snorkeling and then diving.

49:03And then at some point, it was like seven or eight years ago that I went on my first trip specifically to swim with whales. And it's such a visceral sensation of being in the presence of greatness, of being in the presence of the biggest life form that ever existed on planet Earth. And whales are gentle giants. They're these ginormous creatures, but they're not aggressive. Some of them are actually fairly curious. And some of them would let you come very close to you and interact with you. And yes, they're physically enormous, and you do feel small, and you do feel absolutely powerless. Because God knows, I mean, they just would snap you like a twig, like with just a flip of their thin or their fluke.

50:11But I don't think there's ever recorded instance of somebody perishing during a whale interaction. and it's just such a wonderful sensation of a tiny, tiny bit of fear and a lot of awe like when you're eye to eye and face to face with this enormous, enormous creature and I always feel lucky when I'm granted an audience because we don't belong in the ocean for crying out loud, we can't breathe in the ocean so we don't belong there we're guests at best And, you know, if you just being granted an audience, I always feel is exceptional.

50:59Peter High: That's phenomenal. I love that description and being in the presence of greatness. So what a great way to think about that. I wanted to ask you here at the close, Bogomil, as someone who has a job that requires seeing around corners, and certainly part of that is you are blessed with a great series of colleagues and as well as a regular audience with people who are proposing to change the world and many who actually do. But beyond that, I wonder, what do you read or listen to in order to stay current that you might recommend to others? What sort of habits or intellectual diet would you suggest to others who might aspire to capture a bit of that magic?

51:43Yeah, I don't know if I have some very original set of recommendations that people would not have heard of or thought about. But I have been religiously reading The Economist since my sophomore year in college, I believe. And I'm a creature of habit. And so I form a habit. It's there to stay. And nowadays, I listen to the recorded audio edition of The Economist because they have beautiful British accents, like redo The Entire Economist. But the reason I stick to bad habit is I do enjoy long form journalism. I do enjoy not just being presented the facts, but more importantly, being presented an opinion.

52:37and I may agree or disagree with the opinion, but I do like people with strong opinions, publications with strong opinions. And I truly enjoy the quality of the writing, to be honest, and the quality of the language. I feel today there is so much noise and a lot of it honestly pretty badly written. and so that's the reason I stick to The Economist. It's because of their language and because of their opinions. And I have to say that I cautiously try to insulate myself a little bit from the noise. Like, you know, I'm actually not that regular reader of Twitter, for example. You know, I oftentimes feel, oh, it's just like too much noise.

53:31Like many of the 140 character pronouncements aren't that deep, thoughtful, insightful. Thank you very much. Like I don't need to be on top of that like every day. So I try to reserve my quality time for the economist.

53:49Peter High: That's a great suggestion. I appreciate you sharing that, Bogomil, especially as it's such a long formed habit for you dating back to your college years. Well, thank you for a really great conversation. I appreciate you sharing more about your remarkable journey across your life, as well as sharing insights into what you see coming in the not too distant future and the ways in which you and your team are influencing that. I've really enjoyed the discussion. Thanks so much for it. Thank you, Peter. Pleasure. Thanks for listening to TechnoVenture. If you enjoyed this conversation, subscribe wherever you get your podcasts and leave a rating.

54:22Peter High: Thank you. And I look forward to seeing you next time.