Michael Eisenberg (00:00)

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Why did he take you as an investor if you were such a rookie?

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Omri Casspi (00:02)

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In the beginning, he didn't really want to meet me. He was like, “Casspi from basketball? Like come on, what are you talking about? You know, what do you know about cloud security posture management? What do you know about data backup? How can you help me? Why would I take money from you when I have this other option?” It's a very competitive landscape. You have to be 10x more intense about things, and to provide value and to prove your worth. So it's an ongoing thing. 

‍

You can't come to a game and play against LeBron James and expect just to show up and perform at the highest level. He's gonna crush you! 

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Michael Eisenberg (00:28)

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You're at 23% capacity? Watch out world!

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Omri Casspi (00:30)

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One of the Jewish kids came over and said, “Omri, because of you I'm proud to say I'm Jewish at school.” I was like, “What?” Dude, like, I never thought about this. I didn't start playing basketball because of this. 

‍

I always thought I loved the game of basketball, but today I think I love the work and the competition of things. I see the same thing in venture. Like, I love the work around things, of pushing yourself to the limit and climbing the mountain in many ways, rather than the game itself.

‍

Michael Eisenberg (00:53)

‍

Welcome to our next episode of Invested. I'm thrilled to be here with my friend, Omri Casspi. Good morning Omri.  

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Omri Casspi (01:02)

‍

Thank you. Good morning.

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Michael Eisenberg: 

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We’ll get into a whole bunch of things afterwards, but actually, on my way driving in, I saw that you tweeted Deni Avdija's move and poster dunk.

Omri Casspi: 

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First one. 

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Michael Eisenberg: 

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That's his first one? 

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Omri Casspi: 

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That's what he says. First poster dunk. I’m counting on it.  

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Michael Eisenberg: 

‍

First dunk. And I read the Tweet, and I knew we coming to have this conversation today. I said, you must feel like the father of all these players in the NBA, these Israeli players in the NBA.

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Omri Casspi (01:34)

‍

Totally. I love Deni, and I was fortunate to play with him when I came back to Israel, so kind of nurture him a little bit, in a sense. He was 17, 18 at the time. And obviously we had big dreams for him. Every morning I wake up in the morning, want to read the box score, and I want to see how many points he scored.

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Michael Eisenberg (01:50)

‍

That's amazing. Now, like, so you were the first Israeli NBA player in the NBA, and we always spend most of our time talking about venture capital in the NBA. And now there's Deni, and there's this guy Danny Wolf who's now playing for Michigan, 

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Omri Casspi: 

‍

He’s coming up, yep. 

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Michael Eisenberg: 

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And Ben Saraf, who's probably coming in the draft also. How does that make you feel? You;re like, the trailblazer.

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Omri Casspi (02:10)

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Yeah, interestingly enough, I think, you know, kind of looking back at things, you know, I think opening a market was a big thing for me. Obviously representing my country, and being the first one to get drafted in the first round and play for 10 years. And if I have any, even a small percentage of, you know, kind of people's dreams and players' dreams to play in the league–I think it's the biggest accomplishment of my life, in that sense. So having Deni there, and I think it all kind of relates to venture, also, in that sense where, if you look at some of the bigger companies coming out of Israel in the last couple of years, folks are now dreaming of building generational companies. So in that regard, from a sports perspective, we had Gal Mekel, and Deni, and Ben Sarraf, and I'm meeting kids at 15, 14 years old now saying, “Hey, I want to be in the NBA.” 

‍

You know, when I was playing, I remember everybody was trying to put these different boxes upon me. Like, you know, “How about you just make it to the first league and you'll be an Israeli basketball player? You know, like, what are you even thinking about? Like, Euro League? Come on, you're crazy.” And now I'm seeing kids–and I love it. I think the fact that they're dreaming about it, and they're setting high expectations, and goals for themselves–I think, you know, we're going to have more players to go out and play in this league.

‍

Michael Eisenberg (03:27)

‍

That is exactly where I wanted to head, so thank you for making my job really easy today. When we did the first presentation for Aleph in 2013, one of the things we wrote there is, “You could build generational companies in Israel now, $10 billion companies,” which wasn't dreamt of before that. Why? Because the first ones that happened, there was Checkpoint, there was then Wix, and a couple of others. There was a small number, but it was just having these icons. You say, “If he can do it, and he can do it, then I can do it.” 

‍

And I think what you just said about playing in the NBA is the same thing. “If Omri can do it, well then Deni can do it, Ben can do it, and Danny can.” 

‍

Why do you think that iconography, or the fact that somebody has done it first, is so unlocking for other people?

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Omri Casspi (04:19)

‍

I think it's in a couple of different layers. I'm thinking about it a lot, you know, in that regard. If we make the resemblance to tech, you know, it creates this dynamic where investors now also, you know, if you take Wiz for example, “Oh, they've done it. they scaled really fast.” And so we've seen this playbook before, similar teams, big markets. 

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Like, okay, so we can essentially kind of have the same argument for this new company. And then the founders are like, “I've seen Asaf doing it. So why has he done it this way?” And so we can learn from the mistakes that they've made, and take some of the good things that they've done and essentially capitalize on it. So one of my companies has raised more money in a shorter period of time than Wiz. 

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Michael Eisenberg: 

‍

Which company?

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Omri Casspi:

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It's a company called Eon. So essentially they go in after data backup. And it's a similar story from a team construct. They sold businesses before. They'd been in Amazon. They managed data backup and storage for Amazon globally. And now they're going again.

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They’re like, “We're gonna build this massive data backup and storage platform. And there's many other things we can build along the ways of that.” And so investors have more confidence in, “Oh, this has been done before, so we can make a compelling argument to invest in this company.” So I think if we–

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Michael Eisenberg: 

‍

And pay a higher price. 

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Omri Casspi:

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And pay a higher price. And essentially, you always buy the future. We're capitalist and so–it never really adds up. The valuation of a company, especially from a financial standpoint, it doesn't really add up. It's like, at the end of the day, you always buy the future of it, right? And to a certain point, at some point you do get, you gotta meet the market, and essentially you wanna be publicly traded, and then you gotta make the compelling argument to what the value of the company is, right? 

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But in the early stage of things, you always buy the hype. So it's also the same thing. Folks, I think, saw me and like, we have somebody there, and it's time for us to dream about these things and we can practice and–one of the things that I tried to do when I was playing is always come back to the summer, and bring my coaches here, and have them train some of the younger guys and share a little bit of my experience. 

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And I think one thing that I'm really happy about is, I want Deni to be a lot better than me. And I'll tell you a story. A couple of weeks ago I went to Ichilov Hospital to visit soldiers. 

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Michael Eisenberg 

‍

That’s the local hospital in Tel Aviv. 

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Omri Casspi:

‍

So I've done that a lot since the beginning of the war, since October 7th. I try to go almost every Monday. 

And I saw this beautiful family with a baby, and they just came out of the hospital and they said, “Omri, I want our son to be as good as a basketball player as you were.” And I said, “I want him to be much better than me.” And I was thinking about it in that sense and I was like, wow, so now we have Deni. So I really want him to be much better than me. So like, I really believe that. I think the fact that Deni’s there now, and doing what he does, and I think he's gonna inspire the next generation of basketball players.

‍

Michael Eisenberg (07:13)

‍

I wanna unpack this for a second, because I think there's a lot of depth in this for entrepreneurs, basketball players, but in everything you do, that requires both aspiration and excellence. And so, I often wonder for myself whether the fact that I saw somebody doing something, what caused me to do it? Is it, oh, I now believe it's possible so I can aspire for that?  Is it that there is a playbook now, so there's a group of people around who have experience at this and can tell me what to do, and give me feedback along the way? 

‍

Or, which I think part of a point you're making about investors, there's now a supporting cast around that enables an ecosystem to develop that almost expects and demands this of the person. Which do you think it is mostly?

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Omri Casspi (08:02)

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I think it's a little bit of all these different cases. I think for me, I don't know, even now in venture, I feel like a little bit, somewhat of a trailblazer in that sense. I'm the first basketball player to really start a venture firm from scratch, and–

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Michael Eisenberg (08:19)

‍

There were football players, by the way, way back. Ronnie Lott and Joe Montana. I remember those guys. Champion Ventures it was called. 

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Omri Casspi (08:22)

‍

Right, in America. So from that perspective, for me, I always wanted to trail my own way, in many ways. But I think that the fact that there are expectations now in the market, and folks have been there, have done it, and there's an ecosystem from all these companies coming out, founders are coming out, and executives are coming out–and it's also, I call it modern-day Zionism in many ways. I'm sure we're going to talk about it. 

‍

But essentially, the fact that we have generations of companies out of Israel these days, with hundreds and thousands of employees, and just the fact around that, from the businesses around that and the supporting cast around that, and all that sort of stuff, it just really helps the country and the future of our country.

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Michael Eisenberg (09:02)

‍

One of the things that I think is hard about the venture business, as someone's been doing this 30 years, is that it's on some level manic-depressive, right? It's like there are ups and downs, and ups, and downs. The founders, not the venture guys, the founders actually have to push through. You find that any of your sports experience is helpful in that regard? Do the founders ask you about that?

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Omri Casspi (09:25)

‍

Absolutely, in many, many different levels. I think founders are–it's just like playing a game and, you know, Deni had an amazing game last night. And guess what? Tomorrow he's going to have a morning ritual practice, and there's younger guys coming and trying to take his spot. That's just the nature of the most competitive basketball league in the world, right? And there's folks on the bench, and even though they're very happy for the success of Deni, and the success of the team, they want to get their own minutes, and so on and so forth, right? 

‍

So, you always got to be on edge, in that sense, of always proving yourself. So, for example, like one of our companies raised a round. So obviously it's a milestone that you should celebrate, and you should celebrate small wins. But we wake up the next morning and, you know, you have to prove yourself. There's a new cap table, there's more investors, they're pushing you. 

‍

So, I try to behave this way too, because–if I can work, and execute, and deliver to my founders in the same tenacity and kind of obsession that they're doing to their companies, I think I'm going to be able to prove myself as an investor. I think one of the biggest struggles that I had early on, and I think it's an ongoing thing, is you come from sports, and it's great, and there's a lot of respect for sports, obviously, especially here in Israel, basketball and so on and so forth. 

‍

But at end of the day, it's like, you know, “Omri–there's a really established venture capital ecosystem, and there's great investors. Like, what do you really know about this? What do you know about cloud security, posture management? What do you know about data backup? How can you help me? Why would I take money from you when I have this other option?” It's a very competitive landscape. So you have to be 10X more intense about things, and to provide value, and to prove your worth. So it's an ongoing thing.

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Michael Eisenberg (11:17)

‍

One of the things I've always appreciated about you, and I think it comes out in this last sentence, but I want to dig into it, is–I think you have an unburning desire for excellence, which doesn't ever stop. We can perform better on the basketball court. We can learn more about this venture industry. We can drive our founders better, but I can drive myself, in your case, yourself harder. We can do it for the country. And it's a relentless pursuit of excellence. Where does it come from?

‍

Omri Casspi (11:47)

‍

I don't know. It's a really good question. I really don't know. It's not about the money and it's not about fame. It’s also like, when you give it your all, I'm totally fine with the results. I was asked many times, do you miss basketball?

‍

Which is a great question, right? Obviously I played for 16 years, I played 10 years in the NBA, 16-year professional career. I was the captain of the national team, the captain of the Maccabi team for many years. And my answer is no. And I was fortunate to be able to walk away from the game without looking back. And the reason was that when I was 16–obviously trust me, I wasn't that smart at the time. I didn't know why I was thinking, but I promised myself, listen, you're gonna play this game, hopefully gonna be a professional. I don't know where it's gonna take me, but the day you walk off the court, and you walk away from the game, you're gonna be totally satisfied with everything that you've done. You give it your all. You worked your hardest, you woke up early in the morning to lift, and to shoot, and to train, and you're gonna do meditations, and you're gonna do psychology and everything else. So you're gonna walk away from the game comfortable knowing you give it your all. So three and a half, four years ago now, I retired from the game and I haven't looked back. 

‍

So when I look at venture, I want to do the same thing. I actually talked to my team, and I expect that from everybody on the team saying, “Listen, in 20, 30 years, we're going to have a generational shift, and I'm going to walk away from venture. Hopefully, right? I'm going to make it for 20, 30 years and I'm going to be successful. We're going to be successful together and so on. But at some point, I want to be comfortable knowing that I gave it my all. So the next 20, 30 years, I'm going to give it my all.

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Michael Eisenberg (13:32)

‍

That's like, that's a great pep speech to the team, but there's something that burns deep inside. I don't know, I'm trying to access it right now, and try to figure out where does it come from in your childhood, where you were raised, how you were raised.

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Omri Casspi (13:44)

‍

I don't know, I think it's a good question. I think it's a pursuit to be the best that you can be. I think God put us on this planet to do something, and to do good for our community, for our families. I wanna be the best husband I can be. And I always tell my wife, I think the best friends that I will tell my wife–”If I can be better in any way, if you see something annoying, like I wanna work on myself, I wanna be better.” 

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So it's like, it's an ongoing thing on everything. It's on our deck, and it's on our website. I want it to be beautiful. And I want it to be the nicest it can be. It’s on everything that we do. It's like, I wanna make sure that every company, like, when we work with our founders, we're so customer obsessed in that sense, of our founders’ obsession. We're like, I wanna know that we're by far the most helpful for our founders. We have to build an identity. So it's an ongoing thing. It's sometimes hard, you know, because you really push yourself, always, to the limit, but I want to be the best, and I think if we do that, the best I can be in our world and if we do that, there's many other great things we can do to help our country and to help our different things. That's kind of like what drives me.

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Michael Eisenberg (14:51)

‍

One of the first times we met, you were still playing ball. I remember you told me something, which was that you were buying real estate. I think it was in Ohio, if I remember correctly. And I said, “What are you doing? Why are buying real estate in Ohio?” You said to me two things at the time. One is, “It's a chance to learn about business.” The second thing is, “I know I'm not going to be playing this game forever.” There's something else in you which is like, I prepare for the future for the long term. Then when you first said you were going to get into venture, I go, that makes sense, actually, because you're a future-thinking person, despite the fact that very few people have made–very, very, very few people, if any–have made that transition. What caused you to invest in real estate in Ohio while you were still playing ball?

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Omri Casspi (15:37)

‍

I wanted, know, it's like, life after basketball is like, essentially like you prepare for a game, you know, in many ways. You can't come to a game and play against LeBron James, and expect just to show up and perform at the highest level, right? Because if you don't do the work, if you don't lift weights, if you don't shoot, if you don't wake up in the morning, and you stretch, and you massage, and you eat properly, and you prepare for a game, he's gonna crush you. He's gonna crush you most times anyway, even if you do all these things, right? But at the same time, if you do all these different things–so if like, you box out to a rebound, one thing coach always says, is, “Don't look at the ball, you know, go out and do the early work. Box out, put your body in the position, and then go get the rebound.” And then you can put yourself in position to get the rebound. It's the same way for retirement. And it's even more drastic in basketball players and professional athletes, and many, many, many athletes, you know, retiring. They really find it hard to find themselves in life after basketball, right? So you have to do the work early.

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And one thing I tried to do at the time is to meet folks like yourself, and folks in real estate, and ask questions, and to pick their brain about different things, and strategies, and ask dumb questions. And while you're playing–I had a unique position, being the first basketball player from Israel, so folks were really nice, and I was fortunate to meet them even after basketball. But while you're playing, folks wanna meet you. They wanna spend time with you.

‍

I think the NBA have started this, through the player association at the time, this Rookies Transition Program. And one thing that they, essentially do, it was like, bring 50 rookies every year to this camp out of New York, and they teach you about the league, and media, and so on and so forth. So one thing that they told us was like, “You guys are gonna make a lot of money in the NBA. There's guys sitting courtside that make much more money than you. They're billionaires and multibillionaires, right? You play for the Warriors, you see Elon Musk, you see Mark Zuckerberg, right? Folks that are worth $200 billion. So try to get interactions with them, ask them questions, meet them for coffee. Doesn't mean you have to do that every day, five days a week, but even if you take an hour a month, that you can just pick somebody else and prepare for life after basketball, it can go a long way.” 

‍

So one thing that I wanted to do, was like, listen, real estate is somewhat, if you don't over leverage, and you buy in good ocean-view properties, and you can buy in great locations, it's a very solid investment that they can perform well for yourself, and going to create this consistent income of capital. When you retire, you're able to kind of decide with no pressure what you want to do in life. So at that time, I think it was the right decision. I was fortunate to have a really amazing partner, and we did it together, and we still do to many, to many extents. And that was kind of the thesis at the time. 

‍

Michael Eisenberg (18:26)

‍

I know, but so few people do it. Why'd you do it?

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Omri Casspi (18:31)

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I was always very intrigued by the business world. And I've seen many examples, especially in America where folks retired from the game and they, you know, I think could have made better decisions in that sense, of building their future in life after basketball. So I wanted to build for myself and my family, and in a solid conservative investment where, we can essentially, you know, take a year off, my wife and I and the kids, to decide what we want to do and not to have any pressure to make decisions.

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Michael Eisenberg (19:00)

‍

You weren’t even married at the time you start buying the real estate, if I remember correctly.

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Omri Casspi (19:03)

‍

But you know, I was thinking ahead.

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Michael Eisenberg (19:07)

‍

That's a recurring theme that I'm trying to get at. Like, where does it come from? I've had the fortune of meeting a lot of athletes. I think I've met, there's clearly more, but I've met two who stand out. You and Shane Battier, right? 

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Omri Casspi (19:20)

‍

Shane is great.

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Michael Eisenberg (19:34)

‍

Of all the athletes, two stand out as being what I would call incredible students of the game and the world around it, and the business world around it, and understanding the power of team, this kind of incredible forward thinking, striving for excellence at the same time. I'm sure there are others. Where does it come from?

‍

Omri Casspi:

‍

If I don't climb the mountain, I'm falling back. 

‍

Michael Eisenberg:

‍

Interesting. 

‍

Omri Casspi:

‍

I can't sleep at night. Even now, I feel like I'm at 20, 30% capacity, and I'm not climbing the mountain. 

‍

Michael Eisenberg (20:00)

‍

You’re at 20-30% capacity? Watch out world. 

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Omri Casspi (20:13)

‍

That's what I least think, you know? But it drives me crazy. Like over the weekend, I was talking to my wife about this. Like, listen, I'm at 20% capacity, 30%. I don't move. And this drives me crazy in many ways. So I don't want to do anything crazy, or I don't want anything extreme. And I want to be very conservative in how I build things. But at the same time, I feel like right now–you can't be stale on a mountain. Like, you're either climbing up, or you're climbing down. Right now I feel like we're somewhat climbing, but not in the pace that I want to climb. So this thing just burns my stomach, where I'm thinking about these things.

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Michael Eisenberg (20:39)

‍

Quick question before I move on to Sheva and Swish. So you played for the Kings, the Rockets, and the Warriors. Was there a team you wanted to play for, that you didn't play for?

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Omri Casspi (20:49)

‍

I was the biggest Michael Jordan fan at the time, you know, when I was growing up. Michael was the idol, you know, the perfection of a basketball player. I think his peak was the best peak of any basketball player or athlete of all time. I think LeBron maybe had the longest, best, longest career in many ways, doing what he's been doing for 20 something years. But the peak was Michael's. So the Bulls were always my kind of favorite team growing up, you know, at that time. 

‍

One thing that you learn when you become a professional basketball player is that, you know, you play for the Kings and the Warriors–so obviously I love the teams that I played for, you know, and I love the people there. Many people have changed over the years also, but at the same time, like I have affinity and love for the fans and teams that I played for. 

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Michael Eisenberg (21:40)

‍

The Warriors, the team you were on, we should say, won the NBA championship.

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Omri Casspi (21:42)

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Yeah, I think it was the peak of my career in many ways. Also, one thing that you learn the hard way is that you can essentially be in March 5th or something, and play amazing for the Warriors, and then two weeks later you get hurt. And then it's an unfortunate situation. We don't play for the playoffs, you know, and it's like, you come to the locker room and you see Steve and, you know, Steph, and Draymond, and KD and, you know, four or five, maybe six hall-of-famers in your locker room, right? So you play with the best players of all time, and you want to be there for the battles of the playoffs. And it's unfortunate. I almost broke my foot.

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Michael Eisenberg (22:20)

‍

That's actually the perfect segue, because one of my great frustrations of my venture career is, you have a lot of founders that get very, very, very, very far–and then something happens. Market turns–crash. A competitor comes out. You played that incredible season, and then you get injured and don’t get to play in the playoffs. How do you deal with that mentally, and how do you help founders deal with those frustrations mentally?

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Omri Casspi (22:45)

‍

It's easier said than done in many ways. I think being an athlete, and being an NBA player is a close comparison to being a founder. I think the only caveat to that would be probably you just play in the eyes of the public for all these different years, right? It's like if you get hurt and you got hired for the Warriors. I mean, you go back to Israel and it's like, literally every step of the way, every step in the morning, you go out for coffee, people are like, “Hey, it sucks,” or, “You should have done this.” So it's maybe like a publicly traded CEO, you know. Folks are always at the edge of things. 

‍

I remember sitting outside of Oracle Arena at the time in Oakland. At the time we played in Oakland, before they moved to downtown San Francisco. And my wife was at home, my daughter was about, I don't know, six months at the time. And I just came out of a meeting with Steve, and Steve was really genuine in his—

‍

Michael Eisenberg: 

‍

Steve is Steve Kerr, the coach. 

‍

Omri Casspi:

‍

Steve Kerr, of course, the coach. So Steve Kerr was really genuine in the conversation. He was like, “Omri, I think you played really well this year for us.” And I knew this was coming, because I wasn't able to play in the playoffs. 

‍

It was two months–at the time it was April 1st I think, and the assessment was that I'm gonna be out for two and a half months. So essentially I'm gonna miss the whole playoff. Steve was really genuine in the sense of like, “Omri I think you played really well for us. But you know, Steph is hurt, and we’re gonna face Oklahoma City in a couple weeks. And we don't have a point guard, and we must have a point guard, obviously, right? So we're gonna need to replace you with a point guard.” Then I remember walking to my car and you know, midnight after the game, nobody was there and it cracks you, you know? I was crying. I never shared that story. And I was like, wow, you know, it's like, you look back at Oracle and it was like, this is the dream of every basketball player. You play for the best team, maybe of all time, and you're weeks away from the playoffs, and you want to be there. But then I was trying to talk some rationale and things, and I was like, you did everything right. You prepared for the game correctly. You did your work.

‍

You never cut corners. You went to sleep before the game at the right time. You ate properly. You did everything you can. So sometimes, you just have to live with the results and it's part of it. So if it wasn't the case, I would probably have regrets. But I really gave it my all, and you just have to live with the consequences. It's like, you're shooting a three in the end of the game, and it's like, obviously you want to score all of them, or do it in game. But if you put in the work, I'm very comfortable living with the results.

‍

Michael Eisenberg (25:32)

‍

I think there's an interesting parallel here to venture capital and to these startups, that I want to put a fine point on. Which is, most of these don't work out. Just like most people don't make the NBA championship or the playoffs, a tiny percentage of them work out. And sometimes you can put in all the work as an entrepreneur, and think you're doing everything right. And maybe you are. But the gods of the market can petition. Technology changes. Everything moves so quickly, particularly today, that you could end up with a zero in the venture business, even though you think you're on your way. 

‍

I mean, in my career, I've seen things that have been marked up to hundreds of millions of dollars and ended up as a zero. By the way, I've seen some things that were marked to zero and ended up as billions of dollars. The journey matters. The journey matters. We can't control the outcomes all the time. 

‍

Okay, tell us about the venture fund. First of all, tell us about the name of the venture fund.

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Omri Casspi (26:31)

‍

So Swish–we started as Sheva. Sheva means a lot to me. The seventh day of creation…

‍

Michael Eisenberg (26:37)

‍

Just to be very clear, sheva, in Hebrew, means seven in Israel. 

‍

Omri Casspi: 

‍

Seven means the seventh day of creation. And I wanted to start something new. My daughter Sarai was born July 7th, ‘17. I live on the street, number seven, on the seventh floor, unit 27. And then my second daughter was born, also, Esti, in July. I played for seven NBA teams, by the way, too. My number is always seven. So seven really goes a long way with me.

‍

So this is kind of the thesis for Fund One. But at the same time, we wanted something more American. Obviously, we're based here, and we do the work, and we love our country, but we're very much America-facing, and we wanted to do that. I'm still very early in the process. I feel like we're somewhat leading in the second quarter in the game, but I've been to many games, and I lost in the second quarter, right? But in finance, you want to be [more] up than down, obviously, but I love what we do.

‍

I love venture. I've been through somewhat of an up, and I'm sure there's downs, and it's never, not even an even-keel–there's always ups and downs and things not going your way, and so on and so forth. The fact that we're able to interact with amazing founders and to be assistants to them, and advise them in things, and to pick their brains about the stuff. These are the most intellectual, the smartest intellectuals that I've been around, and they see the future, and they want to conquer the world. It's an amazing job and I'm very fortunate to do that. 

‍

Michael Eisenberg (28:13)

‍

How big was Sheva?

‍

Omri Casspi: 

‍

Sheva was $36 million.

‍

Michael Eisenberg: 

‍

How big is Swish? 

‍

Omri Casspi: 

‍

Swish is $60 million more. So in total we're managing almost $200 million, so $180 million. 

‍

Michael Eisenberg: 

‍

$180 million under management. Walk us through a couple of portfolio companies that you say–I know we love all our children, I do this all the time. But give us two or three. Give people an idea of what you're investing in. 

‍

Omri Casspi (28:38)

‍

You know, the last three years since we started, is that everything is on steroids, in many ways. You have to understand what you like, which type of companies you like, what type of industries make sense, what type of industries the public market likes, you know, and so what type of founders you like, and to ask questions, and to build an identity in the ecosystem. Am I a contrarian, or am I going after established markets? Who am I? 

‍

So I think one thing that I challenge with, and I think here's an argument to me where you have to, especially coming from sports and my background, it's not like I grew up in the finance world and I worked at the Blackstones of the world, and I got into venture–and so I had to prove myself. And also essentially build a confidence and trust between my LPs and mine, and our founders and what we do. So I wanted to take a little bit more of a conservative route.

‍

I mean, as conservative as you can be in venture, obviously–as you know, it's not very conservative, but in many ways go after more established markets wit repeat entrepreneurs and folks that have been there, have done it, and now they want to build a massive company. So some of our leading companies, my second company that I invested with is a company called Upwind. First and foremost, we're investing in people and founders. And I was fortunate to meet Amiram and his team when I was playing for the Warriors at the time, almost 10 years ago now, when they were running Spot.io, when they sold Spot.io for almost half a billion dollars. 

‍

So the whole team came together and they're like, “We want to conquer the world this time. We built a business, we sold it for almost half a billion dollars, now we want to build a generational company out of Israel.” So this was really my second investment where I was like, wow, this is what I like. I like working with folks that want to conquer the world, and I was fortunate to invest alongside great co-investors like CyberStars, with Gili and Greylock at the time.

‍

I remember in the beginning, I'm weeks into this thing or months into this thing, and Amiram is talking to Gili and Gili's on the board. And literally after every call that he had with Gili, he had 20 minute debrief with me. And I was like, “Amiram, tell me everything. What did he say? What works? What doesn't? Why is he doing this?” I'm gonna be believing in this first principle thinking of like, really understanding everything from the base. And I was able to challenge every perspective that I had on everything, because I knew nothing, right? So I was like, why? How come? Who's doing what? Why is he doing this? How come he's doing this consistently? I wanna be a consistent investor. I wanna score 20 points, nine out of 10 times. I don't wanna score 20 points and then six points. Why is he doing this? How can he do this consistently? What do you look for? What do you need? How can I help? So all these different questions really helped to shape who I am as an investor. So Upwind is one, now it's almost a billion dollar business.

‍

Michael Eisenberg (31:24)

‍

But I need to ask you a question before we go on to the second one, which is, Amiram–who I don't know–why did he take you as an investor if you were such a rookie? 

‍

Omri Casspi (31:36)

‍

Yeah. I don’t know. He saw something different, I think. It wasn't obvious at all. 

‍

Michael Eisenberg (31:46)

‍

But he could’ve chosen anyone as an investor. 

‍

Omri Casspi: 

‍

Totally, yeah. I think at the time he had eight term sheets. 

‍

Michael Eisenberg: 

‍

Eight term sheets, okay. But he chose you. 

‍

Omri Casspi (32:04)

‍

I think Amiram at the time bought into an athlete mentality, and winning mentality where he knew at the time that I'm gonna do everything I can to help his company and myself win. It wasn't obvious at all. And actually, the following company, they were somewhat in disbelief. They were like, “Why take your money, really? I mean, Amiram knows you for a few years, but we don't. And so why take your money?” And it was a very fair argument. I never looked at it and like, it's disrespectful, and how come they talked to me like this? I'm Omri Casspi, how’s this, that, and the third? Never. And I was like, that's an argument which is something that I need to address, and I want to address it properly. 

‍

And I need Amiram to say, “Omri was 10x, everyone else on the cap table, from the helping, he helped me.” There's other things that I can't do at the time especially, that Gili can, but, “Omri's going to be with me in America, and we're going to trial and error on different things, and we're going to do events together. We're going to introductions, to CISOs,” and so on and forth. And one thing led to another–this company, obviously, Eon is one of our leading companies….

‍

Michael Eisenberg:

‍

That's Ofir Erlich's company.

‍

Omri Casspi (33:33)

‍

Ofir Erlich, yeah. Data backup storage. I remember listening to the pitch for the first time. I met Ofir way before he started the company. So I wanted to do my legwork early and build an identity and relationship with him. Ofir was very vocal in the ecosystem. He's an active angel investor. So we started to build this relationship. And when the seed came around, Eon had, I don't know, 20 term sheets, everybody was like–it's a massive market. These guys know it better than anyone else in the world. 

‍

And there are some things that I should have done better, maybe at the seed, to really properly get into it. And we've done the A, which is also not very typical to what we do. We usually do the seeds. But they're going after cloud-native data backup and storage. It's kind of like, next generation of Rubric, Cohesity. So we've done a lot of work on the market. One thing that we like to do is do a lot of work on the market, and essentially, hopefully, invest in the best team to conquer this thing.

‍

But Ofir really bought into the story. He already had some proofs in the market. But one thing that I always say is like, it doesn't matter. You're always good as the next game, in many ways. Ofir, you know, Deni scored 20 points last night or whatever. You gotta do it again, and you gotta do it again. So Eon, now it’s a unicorn. It's the fastest unicorn in Israeli history. Going after a massive market. Still ways to go. We're gonna work really hard. But I'm obviously very bullish and excited.

‍

Michael Eisenberg (34:32)

‍

So I asked Alon Arvatz, who you know, of course, he's been on the podcast. I said to him, “What's something you want me to ask Omri?” And he said, “Ask him what he needs to overcome in particular to get founders to take his money.” What are the big objections to taking your money? 

‍

Omri Casspi (34:41)

‍

So Alon Arvatz sold Insights, and then they started PointFive. I remember meeting him for the first time. I love him, very dearly. We've been together for almost two years now. I’ve been his investor and been on his cap table. I’m on his board. But Alon was somewhat...in the beginning, he didn't really want to meet me. Amiram introduced me to him. And Amiram was like my founder, I crushed it for him, but he was like–”Casspi, from basketball? Like, come on, dude. Like, what are you talking about, you know? Really? What does he know about cost optimization? We have other options. We sold the business before.” So he was, and I remember I was like, “Alon, like, just put me in, coach. Like, I'm ready to rock and roll. Just put me in, you know? Like, I'm ready to take the battle.” And I didn't get the ownership I wanted at the time.

‍

But like, it doesn't matter. I'm just going to continue to build, and continue with the reputation. And if you prove this for these founders, especially like guys like Alon and his team, you know, they sense success and they sense weaknesses, and these guys are good. So if I prove it with these guys, I'm going to be able to kind of build the next thing. So I think at this point, we're just going to have to continue to prove that we can do it consistently.

‍

Michael Eisenberg (36:13)

‍

I'm fascinated a little bit by the last five or seven minutes of this conversation, because one of the questions I was going to ask you coming into this was, how's it possible we haven't invested together? But I think I now understand, by the way. 

‍

Omri Casspi (36:25)

‍

Tell me why, why, why not?

‍

Michael Eisenberg 

‍

Which is–personally, the fund does, but I don't do cyber investing or infrastructure investing. What you described as conservative markets–I'm not sure it is, certainly where Israel's really been traditionally good at–I've kind of gone the other way. I'm a super contrarian, and I've gone the other way. And so there's a gulf between us. So we're gonna have to close that gulf so we can invest together. We'll talk about that. But you then also said that it's like, I want to score 20 points a night consistently, and every night. And it made me wonder. There's like a story about you, going back to basketball. But I think it's relevant for this. There's like some night, I think you scored 36 points. It was a career high, like trading threes with Steph Curry.

‍

Omri Casspi (37:12)

‍

Yeah, I don't remember that game.

‍

Michael Eisenberg (37:13)

‍

You don't remember that game. But in my own investing style, give me one of those 36-point nights! Not that I'll ever hit three-pointers, but give me one of those 36-point nights, and if I don't do it consistently, it's fine. I'm a 50% zeros guy. 

‍

Omri Casspi 

‍

Wow. 

‍

Michael Eisenberg 

‍

50% zeros guy! But if it hits, I want to–Lemonade hit. Now, you may have both. You may be scoring 20 points a night, and having Ofir Ehrlich do the fastest unicorn ever. You may be the OG, right?

‍

Omri Casspi (37:45)

‍

Obviously I've read a lot of Peter Thiel's books, big fan, and venture at the end of the day is a game of outliers. My biggest position these days is at Eon, obviously the company's really scaling. I think where I wanna be as an investor is that, if I look at my portfolio and I'm gonna be fine with having some misses, I'm gonna have some things that are early or struggling. I'm gonna have some really good hits, and some big winners. And if I can–essentially, obviously it's easier said than done, and you have to prove it consistently. But if you invest in the best founders and you put yourself in positions in these big markets, I think you essentially can build a portfolio construction where if you have one big hit out of 10 zeros, it also means that you might, maybe you got lucky in many ways for what I'm trying to do.

‍

So I really want to have a couple of really good hits, a couple of amazing hits, some misses, which is fine, it's part of the game.

‍

Michael Eisenberg (38:51)

‍

Ofir told me to ask you, why do Israeli startups fail? What's your insight?

‍

Omri Casspi (38:56)

‍

So, Ofir and I debated this a lot. 

‍

Michael Eisenberg:

‍

I guess that’s why he told me to ask you the question. Which means you have two different perspectives, which is excellent. 

‍

Omri Casspi: 

I think this whole discussion was kind of going back to the same kind of first-principles thinking–the argument in venture is that, you know, the first million dollars in ARR and the first revenue has to be founder-led. And this has been true for venture for many, many years. So in many ways though, I invested at Eon, for example, and one of the co-founders is the CRO. So he's a founder. It's not the CEO, but he's a founder, and he's an amazing, amazing, amazing guy. I love him, and I spend a lot of time with him. I spend more time with him than Ofir. 

‍

And Ofir showed a little bit of a different scale, and different interactions with customers from the very early days of the company where he wasn't as, I wouldn't say as involved, but essentially he has distrust with his CRO. They've been together at CloudEndure, and they've been there for many, many years, is that, the company has really scaled, really fast, without the founders really grilling the first million-dollar ARR. So that always got me thinking. I was like, well, hold on. There's something weird here. Like, you guys raised 200 million in a short period of time.

‍

And the sales team is now 15 people, we have a CRO from day one. And if you look historically, you have many of the Israeli startups, especially on an infrastructure level of things, and cybersecurity and so on–how many companies have failed from a technology perspective, rather than essentially, you know, their revenue and so on? So it was like, okay, if you build a DSPM platform–not disrespecting DSPM or any other platform–but like, Israelis most times, they're able to figure out the technology.

‍

Michael Eisenberg (40:44)

‍

We agree. 

‍

Omri Casspi (40:46)

‍

So the technology aspect of things is somewhat, I wouldn't say commodity, you know, but if you look at a construct of a team also, it's most of time a CEO, there's a VP R&D, and a CTO. These are usually the constructs.

‍

Michael Eisenberg (41:01)

‍

And they have no clue who the salespeople are.

‍

Omri Casspi (41:04)

‍

So, hold on, so then I was like, okay, so, but you're telling me that the first 20 people in a company, it's always kind of same rough numbers, 19 of them are on the engineering side, and there's one person, with no help, that he needs to go out and get the first million ARR. He’s never sold in America, doesn't know the culture, doesn't know–a CISO can say, “Oh, I really like this product, but, you know, just change this.” That means he's not buying this thing for two years, right? But he doesn't know that, he hasn't been there. And nobody really helps them. 

‍

So this got me thinking, I was like, hold on. Something needed to change a little bit, in many ways, in that regard. I was leveraging Ofir’s experience as an entrepreneur, and as a leader, and a thought leader of like, really to be able to maybe change the notion in many ways, where like, you have to be ultra focused. So then, how many companies have closed because they weren't able to get that million dollar ARR? One to five, and five to 15, or whatever, right?

‍

And many of the companies failed! That's where they fail. They aren't building to identify the ICP. They're not building a repeatable motion, in many ways. So we have to put thought to this where we need to help our founders. We want these guys to succeed, obviously. We have to help our founders to establish an identity, and a sales motion, and identify an ICP really early in the life of a company. And I think companies are not failing technologically-wise, and they need more help on the sales side. And I think in cybersecurity in many ways, many of the local funds have somewhat, I wouldn't say cheated the program, but in many ways they’ve established these different CISO networks, and so on and so forth, to really help the founders from the very early days of the company to get that, you know, ARR. 

‍

Michael Eisenberg (42:43)

‍

Gili Raanan from Cyberstarts has perfected this to an art.

‍

Omri Casspi (42:48)

‍

Right, and you see that with many of them. It's like, so what do they really do in that regard, right? So they're able to introduce their founders to customers in America and help them bridge the gap to the A. And I think many founders need to understand that they're gonna fail most of the time. They're gonna fail in sales motion, and they need more help. They need to find a VP sales early. It doesn't mean they don't need to be in the cycle. It doesn't need to talk to customers, and so on and so forth, but they need somebody in America.

‍

Michael Eisenberg (43:14)

‍

Ofir also told me to ask you who's the favorite venture fund, or partner out of a venture fund that you like to work with.

‍

Omri Casspi (43:23)

I love all my co-investors. He’s putting me…

‍

Michael Eisenberg (43:28)

Good news, I'm out of the running here because we haven't worked together.

‍

Omri Casspi (43:30)

‍

We haven’t invested together, by the way, it's time for us to do something. 

‍

Michael Eisenberg:

‍

It's time. 

‍

Omri Casspi: 

‍

There's a lot of great investors. I love working with many of them. The way I looked at it at the time, it's just like basketball in many ways. It was like, you knew for some reason, now we'll go back to basketball.

‍

Michael Eisenberg (43:48)

‍

Because you guys have been media-trained by the NBA. You're going to handle this question perfectly.

‍

Omri Casspi (43:52)

‍

So when you play, it's like, there's this amazing player out of Washington. You have to go see him, da-da-da. So like, okay, great. It's like, at some point, I'm going to get on the court. I'm going to compete. I want to feel them. I want to sense. I want them to prove it, in many ways. So it's kind of similar to investors in many ways. It's just great reputations and brands and different things. And folks are great. Let's invest together. Let's see what you bring to the table. And a lot of folks...you know, Gili, and folks at Sequoia, and Sean, and Greylock, and Index, and Excel, and some of the investors that I've been fortunate to invest with, and come in and they prove their worth, you know, they really do.

‍

Michael Eisenberg (44:30)

‍

I won't get a name out of you.

‍

Omri Casspi (44:32)

‍

The best? 

‍

Michael Eisenberg: 

‍

For Ofir. 

‍

Omri Casspi:

‍

I need to think, because Ofir doesn't just ask questions for the sake of the question. He wants me to find a specific person on his cap table that I love. I mean, listen, I love Sean Maguire. And I think he's been an amazing friend of the State of Israel. And he's done so much work. We were fortunate to bring Elon to Israel together. 

‍

Michael Eisenberg (44:53)

‍

We'll talk about that in a second.

‍

Omri Casspi (45:01)

‍

I love Gili. I'm a fan. You know, these two really are the first ones that come to mind.

‍

Michael Eisenberg (45:02)

‍

Our mutual friend and your former agent, Stephen Newman, who's a great guy– 

‍

Omri Casspi: 

‍

I love him. 

‍

Michael Eisenberg: 

‍

He asked how did it feel to be embraced by the communities, which I assume he means the Jewish communities, in the U.S. He said–which I'm aware of–that when you got to the U.S., you began a spiritual journey, also. Tell us about that.

‍

Omri Casspi (45:07)

‍

Yeah, I moved in as a 21-year-old, right after the army. It was very important for my family and I to serve in the army. My father was in Yamam, my brother was in the army, my mom was in the army–

‍

Michael Eisenberg (45:38)

‍

Yamam is the anti-terror unit in the military.

‍

Omri Casspi (45:58)

‍

Of course. And it was very important for me. So I moved in as a 21-year-old and I war it across my chest. I'm from Israel, I'm Jewish, I'm proud of it. I think the proudest moment I had was, I think it was like 2014, 2015, I was in Boston. I did the summer camp, you know, in summer in Boston. They're beautiful. And I went to the camp and had a bunch of, not just Jewish kids at the time, it was some sort of a mix. And one of the Jewish kids came over and said, “Omri, because of you, I'm proud to say I'm Jewish at school.” I was like, “What?” Dude, like, I never thought about this. You know, I didn't start playing basketball because of this. And I was so fortunate that the game, it's taken me in so many different ways. And so I really war it across my chest. 

‍

And I think one thing that bothered me at the time was in Sacramento in 2009, I went to Yom Kippur Shul. And as an Israeli, you feel Jewish, you know. In Israel, everybody here is Jewish, you know, it's like, it's not a big deal. And I went with our head of strength conditioning coach to Shul, and he knew all the prayers. I knew none of them.

‍

I don't think I've ever been in Yom Kippur Shul, never. Probably been once maybe, but I didn't know any of the prayers. Like, dude, this is not okay that, you know, my good friend Daniel Shapiro, who now is the head of strength conditioning for the Clippers, knows all these different prayers and I know nothing, you know. So I wanted to feel part of the prayer with my Jewish community in Sacramento. They've been wonderful. Every city I went through, and every city I played for, the Jewish community really embraced me.

‍

So at some point I wanted to start wrapping tefillin, and, you know, then my wife came about and it was amazing. We had this amazing journey together of just living a Jewish life in America.

‍

Michael Eisenberg (47:36)

‍

Did you have to go to America to do this spiritual journey? Like it wouldn't happen in Israel, maybe?

‍

Omri Casspi (47:40)

‍

I don't think–it's a good question. I don't think it would have been natural here for some reason. It's just weird. But it kind of, I went out of Israel to become more Israeli in many ways also. 

‍

Michael Eisenberg: 

‍

Explain? 

‍

Omri Casspi: 

‍

Being in America, you understand the value and the magnitude of our country, and our people, and our history, and our culture. And in many ways, I felt like at some point I'm losing my, I'm losing Omri, in many ways of living in America. 

‍

It's very easy to dissimulate in America, and to live a different lifestyle in many ways. And I became the biggest Zionist, and I was proud to represent my country, was proud to talk to Jewish communities, was proud to be part of this revolution of Zionism 2.0. And if our grandparents came here in 1940s and 50s and built this country from scratch, and they had to build the first cities, and so on and so forth, now we're able to the scale nation and build a generation of companies out of here, and employ thousands of people, and do a lot of stuff in charity and many other things. It's an amazing journey in many ways.

‍

Michael Eisenberg (48:49)

‍

How are you gonna raise your children differently than you were raised, given what you've been through? 

‍

Omri Casspi (48:56)

‍

Wow. I think my parents have done an amazing job raising us. All three of us. 

‍

Michael Eisenberg: 

‍

Yeah. We agree on that. You have siblings, right? You have two siblings? 

‍

I have an older brother and a younger sister. And I think we always were raised to love our country, willing to die for our country. Family is something that is very important and part of our identity. I think where things change a little bit is now that, you know, I grew up in a middle-class family. My father was in army. My mom was a school teacher. Suddenly you have more means and things that your kids have that you didn't have, maybe, in many ways. But it's also true that we live in different times. 

‍

So I think, if you can teach them to be as modest as possible, and to cherish everything that they have, and to work on their manners, and to do all these different things, you can create amazing kids and children. And we have an amazing generation, I think. We've seen that since the beginning of the war. It's like, listen, we bash a lot of our younger generations, and look at what they've done since the beginning of the war. These guys are heroes, you know, and I think it's our responsibility now to address this, and build the next generation of kids.

‍

Michael Eisenberg (50:07)

‍

I’ve written before that people thought this was the Instagram generation. It turns out it's the insta-hero generation. What’s changed in you since October 7th?

‍

Omri Casspi (50:12)

‍

A lot. You know, some of these things. You could argue, like, these kids are not as tough as we were, you know, they have Instagram and TikTok, and they spend all this time and look at them. I'm very proud. And a lot of times I saw this, like, an interesting quote where one of the soldiers that got hurt in the first day of October 7th was saying, “I'm a hero,” right? And it's like, “I'm a soldier, I'm a wounded soldier, I'm a hero.” He was like, “Many of my friends have continued to fight since.” These guys are also freaking heroes, man. Like, these guys have been doing it for 400 days, 500 days, almost two years now, a year and a half, right? But, you know, they might not get the same recognition as somebody who got hurt, you know, but he was actually saying, listen, these guys are the real heroes. They continue to battle. They continue to deal with mental things, and get hurt, and see many of their friends fall, you know, fall and get wounded in the battle, right? 

‍

I'm out since October 7th, since October 8th, right? So all these guys. It's part of, you know, look at this amazing people that we have here, right? They fight. I remember the first few, I was going to Ichilov Hospital, which is a local hospital in Tel Aviv, every Monday for the first six months of the war. Literally, in the beginning it was like every day. And then after like two, three weeks in or a month in, my wife was like, “Omri, you're taking too much.” It was like, “You're just going every day, and you're crying, you're sobbing with the families,” and then it was soldiers and in the beginning it was mostly families, and so on. So I started going every Monday.

‍

But you go in and talk to this 26-year-old, 28-years-old, the father with two kids who's one of those guys, you just want to kiss them and hug them. And it was like, these guys are amazing. These guys are amazing, dude. Like I didn't think we were this amazing. Suddenly you get exposed to this strength of the fact that we had 350,000 people that joined the army in the beginning of war. It's like, people from all over Australia and U.S., all these people were like, “Oh, we're going to show that we're coming, even though we didn't have an existential threat. We're gonna come, and we're gonna show the world we're here if something happens.” That goes a long way, dude. This really touched me, and the strength of our people, and I love our country. 

‍

Everybody at Swish, everything we do, every investor, we're long Israel, big time.

‍

Michael Eisenberg (52:26)

‍

For good reason. We had that meeting together, that we were both at, with Elon Musk and the Prime Minister. You were involved in bringing Elon to Israel. What was the spark for that?

‍

Omri Casspi (52:37)

‍

At the beginning of the war, there was like this talk around Elon, about whether he is a Zionist, he loves Israel, he loves Jews, he doesn't love Jews. There's no way we can afford losing the modern day Einstein of our lifetime. This guy is like nothing else. Everything he's doing, running eight companies at the same time. Talking about generational companies–this is the generation of the generationals at the same time. 

‍

Like, there's no way, especially now that he's the owner and runs the biggest, most influential tech platform in the world, you know, on an ongoing basis. So I texted Sean, I was like, “Sean, let's bring him to Israel.” And I didn't know Sean at the time. 

‍

Michael Eisenberg: 

‍

You didn't know Sean? 

‍

Omri Casspi: 

‍

No, we had this group chat that we were in together. And I was like, “Sean, let's bring him to Israel.” I was like, “How can we do it? We'll get him an efficient invite, but let's bring him here.” So this was the start of the conversation and we talked to the chief of staff and everybody came and he was here for 12 hours and...

‍

I think it made a big impact on him, and the fact that he was able to go to the kibbutzim around Gaza and see it firsthand. It was a very rainy day, so we weren't able to really walk the kibbutzim as much as we wanted to. But the fact that he was there, and then went out to the Knesset and met with the Prime Minister, and Benny Gantz, and the president, and other elected officials made a big lasting impact on him.

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And there's many things that he's involved with behind the scenes, of helping and establishing and assessing and everything else to the state of country. The fact that he was at the New York Times event, the following day, I think it was, that he showed the dog tag of the hostages. I texted my wife, like, “That's it, I can retire.”

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Michael Eisenberg (54:19)

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Forget basketball, forget the venture career now. Listen, I'm very thankful for that visit, because I wrote this long post in Hebrew defending him, because Haaretz came after him, that he doesn't like Jews, etcetera. He Tweeted in Hebrew, a verse from Proverbs, from Mishlei. The Hebrew Tweet heard around the world, thanks to Elon. Did you ever feel anti-Semitism in the NBA?

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Omri Casspi (54:45)

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To an extent, but in many ways, 95, 99% of every interaction I had in America was amazing. I had one incident,I think it was like the Jewish New Year at the time, it was in Israel and something in Sacramento, someone wrote a swastika on my mural around town. We had like these different murals on town of the players, somebody swastika-ed it. But I cannot say there was–listen, the community in Sacramento was so lovely, so amazing, that this one incident had no impact whatsoever on me, or anything that I've done with the community. 

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Michael Eisenberg (55:27)

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I want go back to, not the Elon visit, per se, but this notion of iconography, which is that more and more today, because of the power of social media platforms and how fast things happen, one is, everything's done in public at this point. Even the startup, Ofir Erlich and Eon, everyone knows it's the fastest-growing, and what happened with Wiz and the $23 billion and Elon coming to Israel.

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And Deni’s–you know, everything happens in the public eye. You're someone who's lived in the public eye. How do you think that changes the way people behave? Founders behave, politicians behave? You spend a lot of time with politicians too. They like you.

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Omri Casspi (56:05)

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I think for me, personally, I think it made me for the better, in many ways. Because you start thinking about every little thing you do, from a very young age. And I've made mistakes, and I've said things that I probably shouldn't, and so on. But you start thinking about different perspectives that might–everything can essentially, people can translate it in different ways. So you want to be very precise at what you do. It can affect many people from different perspectives of the aisle. So for myself, it made me for the better. 

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Michael Eisenberg: 

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Why'd you start a podcast? 

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Omri Casspi:

You know, good question. 

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Michael Eisenberg: 

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What's the podcast called again? 

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Omri Casspi:

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It’s the Omri Casspi podcast. 

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Michael Eisenberg: 

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The Omri Casspi podcast. Catchy name.

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Omri Casspi: 

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I was living in America, and it was a very common thing. A lot of players have done it, you know, and in Israel it was like, nobody's really done it at the time. So I wanted to have a different perspective on my podcast, and I started it when–it was during COVID. So everybody was at home, and I was like, I'm gonna just record this thing and put it out there. And I was fortunate it became somewhat popular, and we won, I think, the number one podcast, in 2020, 2021, ‘22. So I loved it, and at the same time, when I retired, I wanted to take a total shift and focused my 100% into venture and I was like, there's nothing that can distract me from what I'm trying to do and what I want to do. And I really put my head down to work. I still feel like that in many ways, that I still want to continue to put my head down, and continue to work, and only lift it when I start getting results, and real results, in many ways. But it's just the mentality that I have now. So I just enjoy my quiet and being away from the public. 

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Michael Eisenberg (57:59)

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DPI, not TVPI, right? Do you go to basketball games? 

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Omri Casspi (58:02)

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I don't, I haven't been to a Maccabi game since I retired. Almost four years now. 

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Michael Eisenberg: 

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Do your kids like sports? 

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Omri Casspi: 

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My daughters, you know, they're young. 

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Michael Eisenberg: 

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You have three daughters, right? 

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Omri Casspi: 

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So I have two girls and a boy. Michael is three. He looks like a seven year old, for some reason. 

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Michael Eisenberg: 

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Good name, man. I appreciate that, thank you. 

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Omri Casspi: 

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I love it. So he's three looking like five, maybe. So Sarai is seven, Esther is five and Michael is three. You know, Michael is kicking things and throwing things and he's, you know–

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Michael Eisenberg (58:36)

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Even my less athletic kids kick things and throw things, by the way. 

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Omri Casspi (58:39)

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He creates havoc at home. Very different than my girls. My girls are starting to get into it. They play tennis a little bit. They dance. They're cheerleading. They have all these different things and programs after school. So I'm giving them their time. Being a professional athlete is very, very hard. Very hard. I wouldn't necessarily push them to go that route in many ways, but if they decide, I'm totally going to be their support.

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Michael Eisenberg (59:03)

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I was at a wedding last night and talking to a well-known rabbi at the thing, and you know, children of–it's a complicated thing. Especially someone, as we talked about at the beginning of the conversation, is so focused on excellence, as you are. How do you think about that in terms of parenting your kids?

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Omri Casspi (59:19)

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You know, my wife and I talk about it a lot. So you have to examine your child, and to see who he is and what he likes, and they're very different. So there's this thing in Hebrew, being horim le’tiferet. And tiferet means a combination of being strict in many ways–which is gvura–and chesed, which is being very grateful and not grateful, think it's very-

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Michael Eisenberg (59:42)

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Parents, tiferet, it kind of means glory, but it doesn't really mean–it's a combination of strength, or reserved strength, which is gvura, and kindness, which is chesed. 

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Omri Casspi (59:52)

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Which is kindness, exactly. So I think as a parent, you always have to find this fine line between being strict, and you want to have these values, and to push them for success and so on, but also give them their freedom. You have to use–what I like about it also is like, you have to use your brain. If you’re always just strict, it's easy, right? You’re always just strict. It's easy to, not necessarily easy, but like, you're just going on one speed. And if you’re always just not strict, or being kind to your kids, it's also easier, because you're going on one speed. 

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But if you decide at some point, you know, this is a line, and I'm not allowing nobody to cross, and I want to be more strict there. And sometimes I want to be more kind with them in many different other areas, especially kids these days who want to be a little bit more kind in many things. But I want to hold them to a very high standard. And I think kids want to be pushed in many ways. Like, I want to push them for excellence, but in the end, I don't want to put pressure on them in many ways. 

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So like, I told my daughter the first day she went to school a year and a half ago. She went to first grade. I was like, “Sarai, I don't care about the results. You're gonna go to class, you're gonna have a math exam. I don't care about it. Like, I wanna know that you've done everything you can, and you prepared your homework, and you studied through the test. Whenever it comes in the test, I'm gonna be totally fine with the results. You might be the smartest kid, you might struggle. I'm totally fine with the results. But as long as you know that I know that you did the work.” And I think they appreciate that. A lot of times they keep trying to put more focus on the result. Like I want you to succeed, you have to succeed. But you know.

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Michael Eisenberg (1:01:16)

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You can't always control the outcome. like we were talking about before, not in venture, not in basketball. 

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Omri Casspi (1:01:20)

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Totally. Not in school. But I'm gonna be totally fine if I see you coming in from school, doing your homework, preparing for everything, doing everything the right way. You know, we're gonna live with the results. So it gives the kid even more freedom of thought, of like, okay, I don't, you know.

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Michael Eisenberg (1:01:34)

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A few finishing questions. What's something I can't find out about you on Google?

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Omri Casspi (1:01:38)

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I've been in the public eye for 25 years.

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Michael Eisenberg (1:01:44)

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You don’t even have one gray hair to show for it. How is that possible?

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Omri Casspi (1:02:08)

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I don't know. But I think we touched many, many things. I think nailing down on somebody who thinks that what makes me tick, and what makes me g,  is something that I really never, ever thought about as much. I always thought I loved the game of basketball, but today I think I love the work, and, you know, the competition of things more than I love the game of basketball. And I love the game of basketball very dearly. But I see the same thing in venture. Like I love the work around things, of pushing yourself to the limit and climbing the mountain in many ways, rather than the game itself. 

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Michael Eisenberg (1:02:25)

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Who is somebody in this space or elsewhere that you want to say something kind about, that you think they deserve recognition?

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Omri Casspi (1:02:30)

I think my founders, to be honest. Many of them took a gamble on me in the early days. Some of them had more proof in the pudding to show for. I'll tell you an example, like, you walk into the Warriors locker room, you know, think of Steve; you have Steph Curry on one end of the spectrum, and then you have Draymond Green on the other. Both of them are hall-of-famers, first ballot. No debate, Draymond is probably the smartest player I've ever played around. He has this x-ray vision of everything, and he just can translate different things on the basketball court like no other. First ballot, hall-of-famer. The best defender I've played around. 

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KD is somewhere in the middle. He's a little bit of a heart like Draymond, but he's also, we have to talk to him in a certain way. So when I look at my founders like, you can't talk to Steph the way you talk to Draymond. Draymond, you have to go right at his chest. Like, “Draymond, you're not playing great. You need to play better.” Steph, you do that to him, he might take a step back and he might not respond the same way. So like, the same way I look at my founders, like, okay, so I have Amiram on one end of the spectrum. Amiram is a heart. Amiram is a pusher. He's gonna drive everything through everything. Ofir’s in a different part of the spectrum. He's more of a general, right? He's running a show. He's an amazing presenter. He's ultra, I mean–obviously both of them are intellectually smart at the highest level, right? But you have these different things. So there's things that I can pick Ofir’s brain around, and things I can pick Amiram’s brain around. And they all, I feel like they want to give back to me, and they're willing to, and Alon in the middle of all this. Alon is a generalist, like he's running like a general. So I'm fortunate to invest in these guys, and they spread the word for me, and they give me credit for things, many times I’m not deserving of. And they helped me shape myself as an investor in many ways.

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Michael Eisenberg (1:04:34)

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I think this is an important point, by the way. People are different in general. Partnerships of people, how you communicate with them, and people with extremely high capacity, and high aspiration, and high performance are extremely complicated people that need to be dealt with differently. That's very similar, I guess, on some level, between sports. What do I have to do to get Omri Casspi to invest alongside me?

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Omri Casspi (1:04:56)

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You just have to show me something, Michael. You have your own thing, and people–I need to put a camera outside of Aleph and see who's coming in to start calling. “Michael, I see, I want to invest with you, so give us some room to invest with you.” But obviously I've been a fan from afar, and I'm fortunate to call you a friend as well. I was able to pick your brain before I started venture, and during my basketball career, and doing many things, and in politics, and Elon, everything you've been doing for Israel.

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Michael Eisenberg (1:05:25)

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That's very kind of you, but I wanna invest alongside of you now! So I'm gonna have to fight into your deals. We have different tastes, I don't know. Thanks Omri, appreciate it. 

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If you enjoyed the podcast with Omri Casspi, please rate us five stars on Spotify or Apple Podcasts. Subscribe to the YouTube channel, do all those things you're supposed to do to spread the good word.

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Thanks Omri. 

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Omri Casspi (1:05:29)

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Thank you very much.

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