The Twenty Minute VCGili Raanan: One of the Best Seed Investor of All Time: 1 Decacon, 7 Unicorns, 4 Acquisitions| E1128
EVERY SPOKEN WORD
100 min read · 19,748 words- 0:00 – 0:50
Intro
- GRGili Raanan
(instrumental music) One thing I learned, uh, at Sequoia is that we are always as good as our next investment. The moment you, you're happy with where you are, that's the moment you start to lose. Eventually, all my companies are for sale at the right price. I'm not a collector, I'm an investor.
- HSHarry Stebbings
Gili, I am so excited for this. Listen, we met on, uh, on the ski slopes, uh, in Megève a couple of weeks ago, or a month or so ago. I've wanted to do this ever since hearing you speak there. So thank you so much for joining me today.
- GRGili Raanan
It's a pleasure to be here. I'm very excited to have a conversation and, um, you know, I would be even more excited if we can get back to some, uh, skiing together.
- HSHarry Stebbings
(laughs) Well, if you've noticed, I don't ski. I'm like Bridget Jones on the ski slope, Gili, but I really appreciate that.
- GRGili Raanan
(laughs)
- HSHarry Stebbings
I would love to start though with some of your early years and move away from my skiing
- 0:50 – 5:28
Gili’s Background
- HSHarry Stebbings
e- elegantly. So I know it's a weird one, but I think childhoods actually inform a lot of who we are. How would your parents or teachers describe the young Gili?
- GRGili Raanan
You know, I grew up in a, in a, in a small town in, in Israel, uh, which, uh, you know, is probably 15 miles, uh, away from Tel Aviv. But it's, in that, uh, period of time it, uh, you know, Tel Aviv, uh, could be on the moon, uh, as far as I'm concerned it was so far away for me. And, you know, I, I, I grew up, uh, as a, uh, you know, my parents would probably tell you that I was a bright, um, student that never, uh, made, uh, uh, prepared homework. And, and, and the teachers always complained that, uh, you know, whenever they, uh, asked me to read my homework assignment, I would stand up, you know, very casually read out of my notebook, you know, the complete answer that I was supposed to make last night. And then when they approach my desk, they'll figure out the notebook is empty and I was-
- HSHarry Stebbings
(laughs)
- GRGili Raanan
... just making it up. And I, I think that that characteristic of a smart and somehow lazy child, you know, was one of the driving forces behind my career 'cause, uh, unlike, uh, young people today, I was introduced to my first, um, computer, it was a Commodore 64, uh, computer, if, uh, people still, uh, recall that magnificent machine. Um, and I had to choose it, you know? I was not born with, um, computers. And, and, uh, when I faced that machine that, uh, you know, I could tell it what to do and it would do it repeatedly without getting tired, without complaining, you know, as a gifted and somehow lazy person, I really liked the idea. And that, I think, what attracted me to, to the whole tech, uh, scene early on.
- HSHarry Stebbings
Can I be really rude? Do you, do you think you're still lazy?
- GRGili Raanan
In a way, absolutely. You know, I think that laziness in, in, in the right combination is a wonderful trait. You know, it makes you think about efficiency, it makes you, uh, think about not repeating task you don't like and focus on the things you really like and you're really good at, and to find combination, you know? Even forming a wonderful venture, uh, team is, is all about filling the gaps and making sure that, you know, the different elements are significantly better than any of them, you know, alone.
- HSHarry Stebbings
I spoke to one of the greats the other day and they said, um, the most important thing a founder can look for in their VC is a lazy VC, because truth be told, VCs don't add value and the best founders build the companies themselves. So if you pick-
- GRGili Raanan
(laughs)
- HSHarry Stebbings
... anything, pick a lazy VC (laughs) . Do you agree?
- GRGili Raanan
Well, I think that that lazy is in, probably in a different context. Um, I think that as a founder, I wouldn't say pick the lazy VC. I think that you pick, early on I mean, at the seed stages, um, I would go, if I'm an entrepreneur and I like to build, um, a large business, I would go after the style of company builders. And there are many terrific investors who are not company builders, they are-
- HSHarry Stebbings
Mm-hmm.
- GRGili Raanan
... simply terrific pickers.
- HSHarry Stebbings
Mm-hmm.
- GRGili Raanan
In every, uh, successful company there was at least one board member, and typically one board member, that's he or she, uh, are the first call for the CEO. And they're in the room whenever the big decisions, important decisions, are being made. That's the type of investor you like to join you for, for the journey of building, uh, an
- 5:28 – 8:25
Joining Sequoia
- GRGili Raanan
important company.
- HSHarry Stebbings
Speaking of kind of types of investors, I do wanna, kind of, just follow some form of chronology before I just get lost and pepper you with questions. Your first venture role was with Sequoia, um, how did that come to be? And what was that entry like? Can you just take me to it?
- GRGili Raanan
Yeah, absolutely. Uh, I, you know, s- ... uh, I was not a, an unknown, uh, entity for Sequoia. Sequoia, uh, I joined Sequoia in 2009, uh, but Sequoia invested, uh, 12 years, uh, beforehand in my first venture. I was, you know, it was 1997.I was, uh, 27 years old. That was my first, uh, startup, uh, and, and they invested in that business. It was a terrific team. Um, Pierre Lamonde from Sequoia was on the board, and we were the first team to build a WAF, a web application firewall. Um, in the late 90s, that was a big thing. Um, eventually the business was acquired by, uh, IBM. I went to start a- another company and then, um, relocated back to Israel. Was lucky enough, uh, for the, for Sequoia to look for a new partner in Israel. I met the local team in Israel, and then I got to s- to meet, uh, Michael Moritz. Um, he interviewed me and that was it. I was pa- becoming part of the team.
- HSHarry Stebbings
Was, uh, what was that interview with Mike like?
- GRGili Raanan
You know, Mike is a terrific, um, deep, thoughtful, uh, human being. Consider him a friend and try to, to speak with him as fre- as frequently as I can. Um, and, um, the interview with him, you know, I, I came in charging forward, eager to tell him about all my amazing accomplishments as an entrepreneur and techie, and he, he was simply interested in what did I do, but why did I pick to do that, and you know, I, I, I had to slow down. I realized this is a different type of, of interview. Um, and I, I had to focus and talk about w- you know, what drove me and what's my motivation, and, and it au- it was a very, it was a very different interview and, and it taught me a lot about what's important when you like to get to know someone. You get to know someone not by looking at what, you know, the list, the inventory of their, uh, doings, of their accomplishments. You, you get to know someone when you understand why they pick to do that. That will tell you much more about
- 8:25 – 27:23
Lessons from Sequoia
- GRGili Raanan
that person.
- HSHarry Stebbings
Is there any wrong answers to the why? And sorry, I know we're jumping around, but I'm just intrigued. You know, often we demonize, "I really wanna make a lot of money," or, "I really wanna be very, uh, powerful in an S- sector," and we demonize that. Is there a wrong answer?
- GRGili Raanan
I don't think there is a wrong answer. It just, you know, depends what the goal of the interview, but typically, um, I think that Mike liked to, to get to know me better. And when I talk to entrepreneurs today, I like to understand them and, you know, that understanding would, would help me predict their, their behavior going forward. So, give you an example. You said, you, you, you gave the example of, "I like to make a lot of money." You know, one of the questions I try to understand is, are you after fame or fortune? And you can get to real greatness by chasing fame, and you can get to real greatness by chasing fortune. But understanding what's driving you would, would help me better understand you, would help me better help you and become a better partner to you.
- HSHarry Stebbings
I remember getting asked that once by an LP and I responded, "Can I not have both?"
- GRGili Raanan
(laughs)
- HSHarry Stebbings
(laughs)
- GRGili Raanan
Definitely you can. You can g- you can have both, and some people have both, but what's driving you? Typically you know the answer.
- HSHarry Stebbings
No, I, I, I, I do agree with that totally and I think it's really important to understand the why and not the what. Uh, in terms of s- like that being a lesson from Mike, in terms of lessons from Sequoia before we dive in, it's a very transformative place in terms of how one thinks, especially as an investor. Are there one or two takeaways that really impacted your mindset that you took with you to Cyberstarts?
- GRGili Raanan
You know, I think it's a long list. Uh, I spent, um, you know, more than a decade with Sequoia and it's a terrific team. It's a terrific, uh, venture, uh, uh, team, and I learned so much. Um, for me, you know, I, I told you about my early days at that small, uh, town in Israel where, you know, playing, uh, football, soccer, uh, was the, the one thing that kept us alive. Becoming part of Sequoia for me was like becoming, playing for Manchester United. Uh, you know, it's the same game. You know, the same rules, the same eleven players chasing a ball, but it's a whole new level for quality, the combination of quality, tradition, and performance, and if you look just for one elements of that, if you look for quality, if you look for tradition, if you look for performance, there are many clubs you can follow. But if you look for that unique combination, probably Manchester United is the team you like to play for. And, and I really felt like, you know, I'm, I'm playing for them. I learned the power of a brand.
- HSHarry Stebbings
Can you just unpack that? If we do, if, if we just do one by one. Learn the power of brand. In what way?
- GRGili Raanan
The venture business is a, is, is, is a service business. You provide services, and, and once you, uh, and i- it's very hard to tell, you know, if that service provider, if service provider A is significantly better than service provider B, 'cause, you know, what you sell is cash. Once you manage to, to create brand for yourself, and Sequoia's probably the, is the biggest brand in our, in the venture business, um-... you know. You create, you create an amazing cycle where the, you know, the best entrepreneurs like to work for you or partner with you. The best executives like to work for your portfolio companies. All other investors like to invest in your portfolio companies. And the game becomes easier and faster, and, and allows you to, to do great things just because of brand. I spent... Before my end, I spent, uh, um, 10 years working for, um, uh, the Israeli NSA, and then in two small startup companies I've, um, founded. I never worked in a, in a, in a... for a terrific brand. And working for Sequoia, you felt the brand. You felt the power of, um, tradition and, and quality.
- HSHarry Stebbings
Well, I wanna touch on the performance element too. You said about the level of performance. Can I ask specifically, what is it about the performance? Is it how they structure meetings, how they structure discussions, the intent? What makes Sequoia's performance premier above others?
- GRGili Raanan
I think it's something I take with me, um, to cyber starts today. It's, you know, endless hunger. Endless hunger. You're never, you're never satisfied. You know, you could, you could pick Google, you could run the biggest IPO the next day, you know, you run a meeting and ask yourself, "How can I do better?" You're never happy.
- HSHarry Stebbings
(laughs)
- GRGili Raanan
So maybe it's not a lazy investor. Maybe it's the investor that's never happy.
- HSHarry Stebbings
Is that you? Like, d- does, does that sound like a nice way to live? And like, can you win and not be that? Because that is, like respectfully, I think you should appreciate your wins if you wanna be in this business for 40 years. Just beating yourself for 40 years is hard. Like, there are moments when Whiz full IPO and you can sit with Assaf and say, "Yeah, that was great, and, you know, well done. And well done to both of us." I don't know. I, I, I do struggle with this one personally, Gili, 'cause I don't know what the right answer is there.
- GRGili Raanan
Respectfully disagree. You know, I, I (laughs) was spending time with Assaf, uh, till 1:00 AM this morning, uh, and I was giving him crap about something. And, you know, the moment you're, you're happy with where you are, that's the moment you start to lose. The moment you start to believe that you are... you know a lot, and you're experienced, and you're simply amazing in what you do, that's the moment you start to make mistakes. So questioning yourselves and, you know, beating up yourselves for, you know, anything that you could do better and chasing real greatness, I think that's the only, the only ways to, to stay on top of the game. And the moment I'll be happy with, uh, you know, Whiz goes public in, I don't know, in a year, in two years, in three years, and it's a $50 billion, uh, business, the fastest, uh, growing company, you know, ever created, if I'm happy about it, I should retire.
- HSHarry Stebbings
(laughs) We mentioned Whiz there. You mentioned being on the phone to Assaf until 1:00 AM. W- when we've spoken before, you said you invest in people, not in products. And I, I wanted to double down on that one and just unpack that. So why people, not products? And, and how does that lead your thinking when investing?
- GRGili Raanan
That, uh, type of thinking change, uh, changing me considerably since the early days, um, for me as, uh, as a venture capitalist. Because in the early days, I was looking at markets, and total addressable market term, and technology and differentiators, and I, I, I simply realized that all of that is bullshit.
- HSHarry Stebbings
(laughs)
- GRGili Raanan
You know, it's, it's not important at all. The only, the only... You know, when I meet a team of entrepreneurs, um, whatever they tell me, even if they tell me the truth, and often they don't, but even if they tell me the truth about, you know, the, the market they want to go after and the technology they've built, you know, in, in eight weeks, that would change, you know, considerably. And in another eight weeks, that would change again. So why would I spend calories on something that's so temporal in the life of the venture while I could spend time on the more... an- and on the most stable element in a venture, which is the team? You know, the team would change, but it would not change as dramatically as the market and technology. And when you bet... A- and there's another reason for that. When you meet a young team, young for me now is embarrassingly, uh, um, old age, but, you know, when you meet, uh, you know, folks that are 25, 27, 28 years old, that's probably their... they've done, like, two, three jobs in the market. They haven't been senior executives in any business. To really expect them to come up with brilliant market analysis...... and justify why they are getting into a five-billion-dollar market. I think that's setting the bar way too high.
- HSHarry Stebbings
I'm 27. You should slam me as an LP if I'm not incredibly honed on, on where I sit, market analysis, where the m- future venture market is going, just in terms of thoughts. You know, I, uh, by no means comparing myself to any of th- these names, but the Collisons, your Alex at Scale, the best do, no?
- GRGili Raanan
That's not my experience. My experience is that many times, those young individuals, th- they make horrible assumptions on, on a market, or on, um, go to market, and that's not a right, uh, measurement to, to pick, to f- to pick the best teams. As time went by, I, I became more and more purist in my approach to the point wh- where, where I started CyberStarts in 2018. I decided that I would not even ask them about market or technology or product, you know? So I meet with a team, a new team, which I don't know, and we spend an hour, you know, speaking about their childhood and their mother, and not about products or technology. That's enough to really pick, to pick amazing teams. And, you know, my assumption is that if they have a terrific idea, that would be a nice bonus. Uh, if they have a- an okay idea, mediocre idea, I'll help them, uh, improve it. And if they don't have an idea at all what to do, that's even better. I'll work with them, and I'll, I'll, I'll, I'll, I'll... We leverage the entire CyberStarts platform to really help them pick a significant pain point they can go after and build an important company, and we've done it, you know, multiple times successfully.
- HSHarry Stebbings
A mutual friend of ours, Doug Leone, says, you know, a very similar thing in terms of how he really evaluates people, especially when hiring them. And he says he looks for the, the kind of misadjusted children, the ones with the chips on their shoulders who were bullied at school and got beaten by their older brother or sister. Um, that's his signals of someone that excites from a potential perspective. In that conversation on childhood, mother, family, father, what are your signals that excite?
- GRGili Raanan
I listen to their life story, you know? And, and I try to understand the, the why, why they did what they do, why they move on station A to station B in their life. And I'm looking for early signs of them being unique or simply excellent in something, and it doesn't have to be tech. The other thing I'm looking at is whether they've gone through real-life difficulty. Have they gone through something that's really difficult and managed to be successful although they, they faced that difficulty? And in many cases, I meet brilliant people, really amazing, top-notch, um, individuals, and they tell me how brilliant, you know, students they were and amazing, uh, officers in the intelligence forces and the best, you know, Java developer in their company, and I listen to that patiently. And then I ask them one simple question. "Hey, I listened to your story. It's amazing. You've done so well, but it sounds like everything was easy for you. You've been that brilliant kid, brilliant student, brilliant officer, you know, straight A student. You know, what has been difficult for you?" And the tip- You know, they think for a while and typically their first answer is, "Well, at college, at the first year, I got B minus in, in physics," or something along those lines. And I said, "Well, that's not really hardship." So I- I'm looking for the individual who, whose parents went through ugly divorces. I'm looking for the individual who lived in a closet for a while. I'm looking for the individual who was a, a socially isolated, uh, child. I'm looking for people who went through real difficulty in life and became successful.
- HSHarry Stebbings
Can I ask you? So am I. The challenge is those are painful memories to regurgitate. You know, my parents getting divorced, my mother getting multiple sclerosis, seeing the pain, hearing her cry in her sleep every night when I went to bed. It killed me as a son. I don't particularly feel like sharing that with everyone, and esp- uh, you know, I do more now because I'm not in a job interview. But if you're in a job interview or if you're in a fundraise meeting, how do you make people share some of those very hard memories?
- GRGili Raanan
That's always a challenge, how to create that level of intimacy and comfort. You know, w- that's one of the reasons at CyberStarts we don't have offices.... and I take meetings in my backyard, which is conveniently located 50 minutes ride from Tel Aviv in a, in a suburb. Um, it's very quiet. It's very different, you know, than any VC office in the world, you know. Uh, I sit in a converted, uh, shipping container where I took off all the walls and put glasses, so you're sitting in middle of my, um, uh, garden. It's very peaceful. It's quiet. Um, I typically don't, you know, dress up in fleshy clothes for meetings. Everything is kind of toned down. And I tell them about my own journey and my own difficulties and my own failures, and, and as entrepreneur and individual, and typically, I, I get to connect with them. And it's not about investing. I meet people when their company doesn't exist, when there's no company. You know, it's, it's, it's all about partnership, um, and it's almost like picking ano- another co-founder for their team. So if we are not open and transparent with each other, then we won't be able to be terrific partners.
- HSHarry Stebbings
When you think about your painful memories that, you know, you think shaped you, what would you say was the most prescient or noteworthy one that really shaped how you are and who you, who you are today?
- GRGili Raanan
Personally, I went through a, a real, um, a real tragedy and a re- a real pain. My, um, um, daughter, uh, died, uh, five years ago, and that was a real, um, tragedy that changed my life. Now, people know that, and I talk about it, um, and it's, you know ... Sometimes it, it's brought up in conversations, and, um, you know, that, that ... you know, that memory, that experience, and, and others, you know, I, I think that people understand I'm not coming to the meeting with I'm the strong, fleshy VC who's going to abuse you. I really like to get to know you.
- HSHarry Stebbings
In the shipping container with the glasses. (laughs)
- 27:23 – 31:00
Evaluating Founders & Ideas
- HSHarry Stebbings
that approach. Can I ask, in terms of like the ideas, if they do have one. You mentioned the kind of different frameworks, if they do, if they don't, if it's bad. If they do, do you like them to be an insider to the problem, where they've worked in the space for years and they've seen the pains? Or do you prefer them to come at it fresh, naive but optimistic?
- GRGili Raanan
I don't really care.
- HSHarry Stebbings
(laughs)
- GRGili Raanan
I don't really care. I care about their enthusiasm or I care about, um, their energy level when they think about it. Um, and I've done both. I've, I've gone with, you know ... Um, you know. When I met the Wiz team in the previous company, in Adallom, it was 20- 2012. They came to me with, with an idea of securing, um, um, securing Microsoft business applications. Um, I thought it a terrible idea, but I invested in the team, and then we went to, to do a product market feed process, which is called sunrise, and we asked potential customers, you know, "Is that really pain point?" And, m- m- you know, after few conversations, it was clear that the pain point is in the cloud, and securing cloud applications is, is, is so much, uh, more important or perceived to be important by, by those, uh, customers than protecting the on-prem, uh, Microsoft products. And Adallom became a cloud security company. Now, did Asaf know anything about cloud and cloud security in 2012? I guarantee you not. And, you know, it took them two iterations. You know, Adallom was the first iteration, sold that business to Microsoft eventually, and then started Wiz. And now Wiz is, is, is a $10 billion business or, and, and, you know. So you t- you know, you don't have to be an expert to the field to, to really innovate in that field. And on the other le- uh, maybe a, a, a different example is, um, is another company called, uh, Avanade. It's a, it's a small series A stage, stage company, and, and the two founders, uh, Raanan and, and, and Kfir, uh, they came to me and they never dealt with cybersecurity. They always deal ... You know, they've built data products and they were part of a company that was sold to Salesforce for-... $800 million, a data platform, and we decided that they are the data experts and CyberStarts knows cybersecurity, so let's build a data platform for cybersecurity. And Avaloq seems like, uh, a terrific company in the making. So, um, you don't have to be an expert to really, to really, um, to really
- 31:00 – 35:43
Importance of Market Timing
- GRGili Raanan
build amazing companies.
- HSHarry Stebbings
I think market timing is so crucial to building amazing companies. How do you reflect on the importance of market timing when partnering with founders?
- GRGili Raanan
First of all, when they make their investment decision, at the seed stage, I don't think about markets, and I don't think about market timing, and I don't think about all of that. I make a very simple decision. Do we like to partner with those individuals? Do we like to be their partners? The way I, you know ... At CyberStarts, we deal with market timing question, which is super important-
- HSHarry Stebbings
Hmm.
- GRGili Raanan
... is by running, uh, our sunrise process. And a sunrise is, is almost like a counterintuitive, uh, process for most entrepreneurs because instead of going and, and chasing your ideas and, and, you know, dealing with, with prospects' objections and really getting to engagements and closing deals, you do just the opposite. You go and talk to a significant number of, you know, representative customers. You know, large, Fortune 500 companies, chief information security officers. Those are the customers of most of the companies CyberStarts invest in. You tell them, "Hey, here is a new team." You don't ask them, "What's your biggest, uh, pain point," or "What's your biggest need?" 'Cause again, you'll, you'll get so many BS answers it's not even funny. Um ... You ask them some- ... We ask them something else. We ask them, "Hey, this is, uh, a new CyberStarts team that is going to spend about $100 million in the next three years on engineering alone to solve one pain point." That's the average for a CyberStarts company. "$100 million in the next three years on engineering, and we'd like to give you those $100 million to solve one pain point for your organization. What would that be? What's the one pain point you'd like us to solve for you?" And that makes customers focus and listen to you 'cause you change the equation of power. You are not asking them for any favor. You are making them a favor. You're giving them $100 million. So, whenever they give you $100 million, you listen. And they share with us that thing, and that guarantees we are not going to face a market timing issue, 'cause that's something they need now. That's something they are going to spend money and budget now. And that for CyberStarts companies solves the whole market timing issue.
- HSHarry Stebbings
I love that in terms of the phrasing, the shifting of, like, favor for them, not favor for you.
- GRGili Raanan
Mm-hmm.
- HSHarry Stebbings
How many of those conversations do you have before you find a discernible pattern which you're willing to bet against, versus an anomalous company that has a strange requirement or request?
- GRGili Raanan
We typically run about 60 to 70 conversations like that, uh, in the first-
- HSHarry Stebbings
(sighs)
- GRGili Raanan
... three months since inception. And then ... we come back and have a second set of 60 to 70 conversations with our solution thesis. So the first batch of conversations is all about, uh, the pain point. That helps us figure out what's the one big pain point we like to go after and build an important company. We come up with a solution thesis, and then we come back to those, um, potential customers and tell them, "Hey, we listened to you. We listened well. This is the concept for solving that one big pain point you told us about. What do you think about it?" And if they like it, we'll go build it and then come back to them in three or four months and ask them to try it out. And then they become our first
- 35:43 – 41:22
Interaction with Founders
- GRGili Raanan
customers.
- HSHarry Stebbings
When you go through this process, how are you and the founders interacting? Are you on these calls with the founders? Are you doing them for the founders? I'm just trying to understand 'cause it feels like you're founding the company.
- GRGili Raanan
I don't babysit founders. Uh, I'm not in the meetings. But, um, we do follow up. Either me or my partners, um, Lior, Emily, Hilan. You know, we would follow up after each conversation. We have a system where we rate those, uh, meetings together with the founders, and we would meet weekly to discuss, you know, what we've learned and how we should go forward with our, with our process. Uh, the sunrise process is an amazing, is an amazing, um, process. It's a super hard experience to go through 'cause ...... unlike, unlike the traditional first-year experience, you take all the hypothetical objections you might face as a company in the next three or four years and bring it to present. So you ask all the tough questions yourself, you, you know. If, if, uh, a potential customer says, "I like your solution," you'd respond with, "Why? Why wouldn't you buy it from Palo Alto Networks? Why wouldn't you buy it from Wiz? Why do you need us?" And, and then we would ask them, "How would we price it? And why it's so high? Why it's so low? You know, what's the right channel? How, how would you technically evaluate that type of solution?" Even before we, we have written the first line of code, we don't have a product, but we ask you how would you evaluate that product, how would you want a POV for that product. So essentially, we ask all the tough questions in the first few months for the venture, and then that then allows our companies to accelerate. If you look at companies like Wiz, Island, Fireblock, Noname, Sierra, Avalon, or your- all those companies, they managed to get to, you know, significant, um, revenues, significant ARR in the first 12 months, in the first 24 months, thanks to that process. 'Cause you get... You simply get a better functioning and streamlined businesses by asking all those hard questions.
- HSHarry Stebbings
Does an efficient outcome always come from Sunrise? And what I mean by that is, does it ever happen where we say, "Hey, that didn't actually produce anything meaningful for us to go after, and yes, we disqualified a lot of ideas, but we don't have something concrete to actually do"?
- GRGili Raanan
Hey, first of all, uh, one thing I learned at Sequoia is that we are always... We are always as good as our next investment. So who knows? But, uh, if you look at the current, uh, Cyberstarts portfolio, we are like the... You know, overall, I believe, like, 21 companies. Four are still running, uh, Sunrise, so who knows? But out of the 17 who went through Sunrise and raised series A, seven are unicorns, uh, one is a decacorn, and, and three got acquired. So I think the hit rate for Sunrise is, is pretty good.
- HSHarry Stebbings
(laughs) Can I ask you, does it get easier then? You know, with that hit rate, every single multi-stage firm will just go, "We have to invest in Cyberstarts companies. We'll pay double, but we have to be in them." Like the Sequoia brand makes it easier to raise more money, to get deals, does it get easier now you go, "Look how good we are," bluntly?
- GRGili Raanan
It gets easier to, to raise money and record talent. And, and, and fundraising for Cyberstarts is, is a pleasure. And I think the last seed fund, you... You know, I think it took me, like, um, 90 seconds to raise the fund, you know. Nine WhatsApp messages and it was done. But the Sunrise process itself and the companies' journey themself, they... That doesn't get easier.
- HSHarry Stebbings
Mm-hmm.
- GRGili Raanan
That's as hard as it was in the first summer. It's an ego, um, destroying process. You know, you, you, you die, like, dozens time during the process. It's so difficult, 'cause you hear all the reasons people are not going to buy your product. There are all the, the reasons people are not going to like you, all the reasons people are going to pass on you, and that's hard, really hard. By now, um, between Cyberstarts and, and Sequoia, like, 35 times, probably more than most people, uh, on Earth, and it still... Each time I'm getting into a new Sunrise process with a new team, I have to prepare myself, myself mentally.
- 41:22 – 42:45
Getting Back Up After Failure
- GRGili Raanan
It's super hard.
- HSHarry Stebbings
How do you get back up when you're hit down? Everyone gets hit down. I was talking with a, you know, billion-dollar founder today in the park, and he said, "Hari, you will get punched hard. It's just about getting back up every time. It's all I've learned." How do you get back up when you're punched? What do you tell yourself?
- GRGili Raanan
I don't tell myself anything. I just feel it. I know I'm, I'm up. Keep, keep on going. I don't have to, you know... I, I just feel the energy, that I think something we, we spoke about, you know. The moment I don't have the energy, the moment I don't have the drive, the moment I have to talk to myself and convince myself that I need to, you know, recover, that's the point I should retire. But when I simply, you know, stand up and walk just because I'm stupid, that's... That's a good sign that I should stay in the game.
- HSHarry Stebbings
Gilly, I've run a marathon every weekend for a year, so, like, 52 marathons in 52 weeks, and I can tell you one thing, I have to fucking convince myself. (laughs)
- GRGili Raanan
(laughs)
- HSHarry Stebbings
If I just didn't feel it.
- GRGili Raanan
(laughs)
- HSHarry Stebbings
I mean, Jesus Christ. I have to convince myself to everything. Like, everything is a fight against my own mind in that way.
- GRGili Raanan
Yeah.
- HSHarry Stebbings
It's, it's really interesting to hear.
- 42:45 – 44:22
Learning from Losses
- HSHarry Stebbings
Um, uh, you mentioned some of the incredible successes there when you analyze the portfolio with the decacorn, the seven unicorns.... respectfully, I think we learn a lot also from losses or from not having success. When you review maybe your biggest loss, how did that impact your mindset and how you think about investing in founders?
- GRGili Raanan
I- it always goes back to the team, you know? If it wasn't clear tho- so far, I'm, (laughs) I'm a big believer in, in the, um, you know, human element here. Um, so y- you think about the team, and you think, you know, "Where have I been wrong about the team? What I missed about the team?" And I try to, to analyze that and learn from that and, and, you know, at least not repeat my mistakes. It's fine that I'll make new mistakes, but it's stupid to make the same mistake again and again. So I, I try to learn and move, move, move forward. And, and it's also a business where y- you have to, to, to focus on the things that do work, 'cause so many things are, are, are fucked up, so many things did not work well. A- and so you simply have to focus on the things that work well and then do more of them. If you've m- successfully able to, to f- to focus and repeat the things that you are doing well and do a little bit less of the things you don't do well, on the long run, over 10, 20, 30 years, (laughs) you'll be like a god. You'll be
- 44:22 – 45:25
Focus on What Works
- GRGili Raanan
super successful.
- HSHarry Stebbings
If we focus on doing the things that we do well and a little bit less on the things that we don't do well, if you were to apply that to yourself today, what do you think you do well and what do you think you should do a little bit less of that you don't do so well?
- GRGili Raanan
Pick the right teams, go after important companies. Those are the things we do very well at Cyberstarts. Um, what we are not doing well, coming up with ideas, running thesis on markets. You know, you ask me what I think about AI security. You know, what do I know about AI security, you know? I spent only 30 years plus in cybersecurity and what do I know about it? What we, you know, we are not good at-
- HSHarry Stebbings
Come on.
- GRGili Raanan
... m- matchmaking, uh, uh, between founders.
- HSHarry Stebbings
Hmm.
- GRGili Raanan
That's something that, you know, I, I, I see other investors do, and that's, that's a miracle to me.
- 45:25 – 46:06
Challenges in Matchmaking Between Founders
- GRGili Raanan
How do you do that?
- HSHarry Stebbings
Why do you think you're not good at the matchmaking between founders?
- GRGili Raanan
First of all, if, if I knew why, I would fix it and I would become great at this, though, uh-
- HSHarry Stebbings
Oh, wow.
- GRGili Raanan
... even if I know why, it's probably the wrong answer. The wrong answer I have in my mind is that, you know, it's, it's a, it has to be an organic process. It's very, very hard to, to create real connection that would last for, you know, a decade plus if you're thinking about a, a, a, a longterm, uh, business. And, and it simply works better
- 46:06 – 49:04
Prepared Mind’s Movement
- GRGili Raanan
when it's organic.
- HSHarry Stebbings
You said there about the thesis. We have a lot of, uh, large multi-stage funds, Gideon, and they like to have these prepared minds. Um, I, I favor an unprepared mind, being open to whatever the entrepreneur is willing to build, be courageous enough to pursue. I think prepared minds confines your imagination and allows you to be a BCG, you know, associate in a large fund and lose your humanity. Um, how do you feel about the prepared minds movement and the importance of it?
- GRGili Raanan
I have lots of appreciation for that. I, I, I, I'm, I appreciate people and organizations that learn, that, uh, adapt, that prepare themselves. That's all fine. My business is different. I'm a seed investor. And I have to come in for a process with new team, completely unprepared, have my mind not be poisoned by any thought about, you know, what they can build and what they can go after. So I think it's a diff- it's slightly different profession and slightly d- and, and a, and a different mindset.
- HSHarry Stebbings
I agree. It's a different business, actually, in many respects. And I think that also very much applies to price and price sensitivity. I remember having Peter Fenton on the show, and he said that price is a mental trap, Harry. How do you think about price sensitivity when doing deals today and when to pay up versus when not to?
- GRGili Raanan
In the best companies, if you look at it, we're insanely expensive at seed, insanely expensive at Series A, i- i- insanely expensive at Series B and so on. It's, you know, it's like almost part of their DNA to be expensive companies. We invest at seed, so even expensive seed is not that expensive if you're building a, a bil- a, a multi-billion dollar, uh, business in valuation. Um, but I agree, the, the, most investors' mistakes were not to invest in the right company because they thought it's too expensive. By the way, it goes, it goes both ways. When I speak with entrepreneurs, I always tell them, "The Cyberstarts money is the most expensive money you can buy for your equity," 'cause it's a deal, you know? They buy cash and they pay with equity. And we are the most expensive cash they can buy. So the price trap is not just for the investor, it's also for the entrepreneur. Would they pick...... you know, the best investor for them, paying a higher price
- 49:04 – 49:56
Role of Price Sensitivity in Deals
- GRGili Raanan
in their equity.
- HSHarry Stebbings
Do you think you have pricing power now, Gili? Which is, founders want you so much they will choose you at a lower price?
- GRGili Raanan
Potentially, but I-I really don't know 'cause, you know, most of our deals at the seed stage look the same. We don't try to twist their arm and- and get one or two points more just to- for- for- for the sake of making a little bit more. Um, so- so maybe- maybe the answer is yes. We haven't tested it.
- HSHarry Stebbings
How do you advise founders on how much to raise for? I think- yeah, and for me as an outsider to Israel in particular, I see large seeds like $6 to $10 million, and they'll dilute 30%, which is quite different to a European company which will raise less and dilute less.
- 49:56 – 51:38
Right Amount to Raise & How Much to Raise For
- HSHarry Stebbings
How do you think about and advise founders on the right amount to raise, and how much to raise for?
- GRGili Raanan
It really depends on the domain. I- in most enterprise software companies, cybersecurity included, I found out that you need at least five or six million dollars just to get team, product built, and a small go-to-market team to- to win few deals. That's what- that's what it typically take to build a- a- um, an enterprise software company or cybersecurity software company in- in the early days. And that- that's typically what we do. You know, if you look at, uh, the CyberStarts, um, pre-series A company, if you like, a Sunrise graduate, uh, company, you would see a- a terrific team, uh, that solves a huge pain point as validated by dozens of, um, US companies, um, with technology that works in production, where few of those, um, customers already paid, you know, few hundred thousand dollars for the solution. And that's the point we go and- and raise series A. To get to that point, it takes about $5 million. So it's not bad that you have $7 million as seed.
- 51:38 – 53:39
Speed of Execution vs. Being First to Market
- GRGili Raanan
It's not terrible.
- HSHarry Stebbings
Is speed of execution the single most important trait in scaling in that first zero to seven million dollar range?
- GRGili Raanan
I think that cybersecurity is- is a market where being first to market is not necessarily an advantage. Sometimes it's better to be number two, number three to market, uh, and come in with- with more knowledge, more context, and simply, you know, deliver a- a- a better product. And better product would, you know, not just make customers happier, it would attract, um, better channels, and would translate to faster, um, sales velocity, um, in go-to-market. Speed by itself, you know, is not bad. But that's not the most important thing. The most important thing is really figure out product market fit. Understand the pain point. Who has that pain point? How do you explain that pain point to that individual? Um, what's the right demo to convince them to take your product for technical evaluation? How do you run the most efficient technical evaluation for that individual to get conviction that they'd like to procure your software? And what's the right pricing for your solution for the pain point it solves? If you figure this out, you can move. You have a repeatable process that you can simply execute again and again and again successfully. You can raise a lot of money, put, you know, as many, um, account executives and channels around that, and you've got a beautiful company. In my view, that's way more important than just sheer, uh, speed.
- 53:39 – 54:58
Cash as a Weapon & Importance of Liquidity
- GRGili Raanan
- HSHarry Stebbings
Gili, can cash ever be used as a weapon? And what I mean by that is, your competitors raise a lot of money. You need to raise a lot of money, too, to compete, whether it's on paid marketing, whether it's on sales team expansion, whether it's on R&D. Is cash a weapon that can be used and leveraged, or actually, is it a short-term play and the long term is different?
- GRGili Raanan
Cash is very important. You know, it's ... Building a large substantial company is a very expensive e- exercise. I didn't find, unfortunately, a cheap, uh, inexpensive way to do it. So it- it's- it takes- it takes a lot of cash. Uh, companies need to raise a lot of money. It means that, um, valuations sh- should be high, 'cause no founder would like to get 50% dilution just to get the cash they need. We support that, and we provide the platform to run fast, you know, get fast- faster to product market fit, which means that you create a repeatable sales, uh, machine earlier, you get to higher valuation earlier, and you are able to raise more
- 54:58 – 59:08
State of the Market
- GRGili Raanan
money than the competition.
- HSHarry Stebbings
Speaking of cash as that weapon and raising more than the competition-Prices seem high again. And we've chatted before, and I wanted to ask, are 2021 valuations back, Gili? And how do you analyze-
- GRGili Raanan
Yes.
- HSHarry Stebbings
... the state of... Yes.
- GRGili Raanan
Yes. 20 and 2021 is back. For the past four, five weeks, we are definitely in a, in a, at least in private markets, we're in a, we're in, we are in a new, uh, bull run. You know, valuations are high, sky- skyrocketing.
- HSHarry Stebbings
Do you think it's a tale of those that, that have and those that have not? Which is like, for the half a percent, it is a bull run, and for the 99.5%, it's hell?
- GRGili Raanan
No. I think that once you start a bull run, you'd, you know, that definitely the one, the, the one percents would have terrific life, but that would have impact on, on the rest of the pack.
- HSHarry Stebbings
Mm-hmm.
- GRGili Raanan
And if I look at my own, our own portfolio at Cyberstarts, uh, our companies are in the process of raising probably more than one and a half billions dollars in an- in the next few weeks. The impact is not just for the, you know, the one percent company. It's, you know, you see the impact across the whole pack.
- HSHarry Stebbings
Does this make you happy? I know that sounds like a strange question. Obviously, your companies getting well-funded is a good thing. But 2021-
- GRGili Raanan
Told you already that I'm never happy.
- HSHarry Stebbings
Well, you were never happy, one, but 2021 valuations created a ton of problems downstream. It created a lot of very difficult situations for companies to have to live into those valuations, option pools being set so high, the list goes on and on. These were not good. Are you worried?
- GRGili Raanan
I'm always optimistic, Harry. I'm not worried. I'm optimistic. Uh, you know, the market is the market. If you can raise, um, significant cash and build a business, you should do that. That's the right thing to do. Now, it's our responsibility as investors and board members and, and entrepreneurs to, to really, um, look at the way we spend money and have the, um, you know, the systematic approach of, of building companies. That shouldn't change just because you have more cash in a bank.
- HSHarry Stebbings
It always does. Yeah, everyone's like, "Oh, I've put it aside for a rainy day." Every great founder pulls forward a new product, hires the new data team, hires the new sales team because they can.
- GRGili Raanan
There's bad behavior attached to using, uh, TikTok-
- HSHarry Stebbings
(laughs)
- GRGili Raanan
... or Facebook, and still as far as I checked, uh, an hour ago, they're still up and running.
- HSHarry Stebbings
If 2021 is back, it means we should be thinking as early stage ambassadors about liquidity in some respects. Because in a lot of ways, the price-to-value ratio is brilliant if you're a seller. Are you actively looking at liquidity options, and given 2021, pricing is back?
- GRGili Raanan
You know, liquidity is part of my business. You know, I like to say that eventually all, all, all my companies are for sale at the right price. I'm not, I'm not a collector. I'm an investor.
- HSHarry Stebbings
(laughs) What have been some big lessons for you in when the right time is to sell actually, and not to hold?
- GRGili Raanan
There's lots of context to, to the right, uh, answer here. And I'm, I've, I'm not sure if I've made the best decisions, uh, so don't, don't know if I'm the one that should teach others, uh, on, on timing of selling. As an early stage investor, I think it's, it's smart to look for, um, liquidity opportunities and consider the context, the company, your fund, you know, many other elements
- 59:08 – 1:03:45
Distinction Between Seed Funds & Opportunity Funds
- GRGili Raanan
in, in your business.
- HSHarry Stebbings
Speaking of kind of the other elements in your business, I am intrigued, you know, you scaled up Cyberstarts' fund size quite a lot over time. Can you just take me to that decision-making, given you said earlier, "My business is seed," and it's that really early why on people? Now, you have funds that are significant. I mean, really significant. Um, w- can you tell me about that decision-making process and why you decided to scale in that way?
- GRGili Raanan
I'll explain it, and, and you'll figure out immediately why I said that we are simply in the seed business, and that hasn't changed. So, uh, at Cyberstarts, we have two, um, two type of funds. Um, seed, uh, uh, funds. We are now investing out of Cyberstarts Seed Three. Our seed funds are $60 million in size, and we write first and last check to, uh, new teams. No follow-on investments out of the seed funds. Um, and then we have a half a billion dollars, $500 million, um, opportunity fund that, where we invest in follow-on, uh, rounds in, in our own portfolio companies. The whole, uh... So we didn't become, we didn't transform our business. We didn't shift it to late stage or multi-stage investments. We are seed investors with a big wallet to invest in follow-on rounds in our own companies, where we do not set the price. So we do not set the price out of the opportunity fund.
- HSHarry Stebbings
A couple of questions. One, how do you avoid signaling to prevent others from going, "Huh, Cyberstarts aren't d- doubling down from their 500 million fund? Can't be a good one"?
- GRGili Raanan
... so far we invested in all series A and series B of our companies.
- HSHarry Stebbings
Do you expect that to be the same going forwards?
- GRGili Raanan
I don't. I don't know.
- HSHarry Stebbings
Hmm. Do you get, like, check sizes that you want? 'Cause when you don't set the terms and you don't set the round, your check size is really at the whim of someone else. How do you ensure you get the check size you want when you don't own the round?
- GRGili Raanan
Typically it's very, um, easy for us to, to take pro rata and, you know, other investors, uh ... you know, we have lots of friends in the industry and they respect the, um, partnership.
- HSHarry Stebbings
(laughs) In other words, they're fucking terrified to not give you what you want. (laughs) I-
- GRGili Raanan
We have terrific-
- HSHarry Stebbings
I said it, Gili.
- GRGili Raanan
We have terrific partners.
- HSHarry Stebbings
That is amazing. Listen, I wanna ask one more before we do a quick fire but ... And it's, I'm sorry it's a weird one, but you're optimistic, you have a wonderful way of looking at the world. I think, respectfully, and I hope it's okay, but, like, personal finances do shape a lot of one's mindset. It makes one upside inherent, not fearing downside protection. Do you think rich investors make better investors?
- GRGili Raanan
You know what, Harry? I don't know, 'cause for most people I co-invest with, um, their, their net worth is not published, so I have no idea. But my guess is that the answer is rooted somewhere else. It's not around net worth, it's around terrific instincts, knowing your game, um, pattern matching, uh, terrific network, and, and other elements.
- HSHarry Stebbings
Did money make you happier?
- GRGili Raanan
It definitely made my life more comfortable.
- HSHarry Stebbings
What was the single biggest thing that changed?
- GRGili Raanan
One less thing to, to be worry about.
- HSHarry Stebbings
I'm so sorry to be so crass. Is there a, is there a number at which point that happens?
- GRGili Raanan
Probably each, each one of us is a different number. I'm sure that there's a number that would make you not worry about it anymore. Uh, and probably my number and your number are different.
- HSHarry Stebbings
Go on. I'll tell you mine.
- GRGili Raanan
(laughs)
- HSHarry Stebbings
(laughs) Listen, it was worth a try. I would, I would be remiss if I didn't try it, Gili. (laughs) Um-
- GRGili Raanan
And I respect that. I, I, I didn't expect you not to try.
- 1:03:45 – 1:09:16
Quick-Fire Round
- GRGili Raanan
- HSHarry Stebbings
Uh, listen, I would love to move into a quick fire round, Gili. So I say a short statement, you give me your immediate thoughts. Does that sound okay?
- GRGili Raanan
Perfect.
- HSHarry Stebbings
So let's start with, what have you changed your mind on most in the last 12 months?
- GRGili Raanan
Product marketing.
- HSHarry Stebbings
Hmm. What do you mean?
- GRGili Raanan
I was big believer in product marketing in the early stage. I kind of, uh, lost faith.
- HSHarry Stebbings
Why? (laughs) This is a, this is like a grenade in the, the quick fire round. That's a very bold statement. W- why did you lose faith?
- GRGili Raanan
When I look at early stage companies, the common thread among all of them is, you know, once they start to sell software, is that they don't have enough opportunities and they don't have enough pipeline. Previous- previously I spent a lot of efforts within marketing around product marketing and not around demand generation. You ask me a year ago who would be- who would be the first hire at a marketing organization, that would be product marketing. My mind changed.
- HSHarry Stebbings
(laughs)
- GRGili Raanan
My answer today is demand gen.
- HSHarry Stebbings
Huh. How's that?
- GRGili Raanan
And that can accelerate ... that can make a, a huge impact on a business early on.
- HSHarry Stebbings
Gosh. Saving some wisdom bombs, hey, Gili? That's a, that's a quick fire answer and a half. Um, what's the biggest misconception of the Israeli tech ecosystem?
- GRGili Raanan
Selling early.
- HSHarry Stebbings
You don't think you do sell early?
- GRGili Raanan
That's the misconception. I think that anyone who sells early has a reason for that. It's not an ecosystem trait, it's not an Israeli trait. You know, if you have a terrific product selling amazing to a huge market, and everything in the founder's relationship is amazing, why would you sell? So I see, um, more and more repeat entrepreneurs, but also first time entrepreneurs that are doing amazing job and eager to build, uh, sustainable companies.
- HSHarry Stebbings
What's the best investment advice you've been given?
- GRGili Raanan
Focus on the team.
- HSHarry Stebbings
(laughs) Sure. I see a common thread here. What's the biggest piece of-
- GRGili Raanan
(laughs)
- HSHarry Stebbings
Wha- what's the biggest piece of BS advice that you often hear or see being given out that you don't agree with?
- GRGili Raanan
Whenever entrepreneurs tell me that, "Customers love what we do. Every customer we spoke with like to get our product," you know, lo- like to get their hands on a product, you probably misunderstood the customer. You probably didn't listen well in the conversation. That's impossible.
- HSHarry Stebbings
What's the most memorable first founder meeting you've had?
- GRGili Raanan
Was a meeting with, uh, Asaf, uh, Rapport at Adlon where he didn't show up.
- HSHarry Stebbings
(laughs) Walk me through this. What happened? He just never rocked up?
- GRGili Raanan
Uh, we set a meeting and his two co-founders showed up and said that Asaf didn't think meeting with investors is important, or something along those lines.
- HSHarry Stebbings
Ho- do you think founders should always be raising?
- GRGili Raanan
No, no. I think that in many re- res- respective, FOMO is your biggest friend as founder.
- HSHarry Stebbings
Thanks, Gili. That's helpful. Um... (laughs)
Episode duration: 1:09:17
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