Jeremy Pressman: Don’t Be Afraid to Fail

Jeremy Pressman: Here you're taught that you should, and you can go ahead and fail, and fail time and time again. It's a good character building experience. As an investor here in Israel, if we see a company or a guy that's raised money, or a lady that's raised money previously, and that endeavor has failed, it's not necessarily viewed as a bad thing.

Jeremy Pressman: Here, you are encouraged to try new things, to try to continue to push those limits. Sometimes you wind up punching the guy in the chest and they call it technical foul, or flagrant. You get fined. You get thrown out of the league. And other times they don't even call anything.

Michael Redd: Hey everybody, this is Michael Redd. And welcome to the Betting on Yourself podcast, where I interview successful entrepreneurs, athletes, and other top performers who rose to the top, took success into their own hands and bet on themselves. I met my buddy, Jeremy Pressman back in 2019 when I took a trip to Israel and I love his passion and his drive.

Michael Redd: He knows a thing or two about having vision and what it means to bet on yourself. For six seasons, he played in Israel's Artzit basketball league, and he's also an innovative venture capitalist. Now a partner at Advantage, an organization that I've partnered with that focuses on sports tech starters. A fiercely hard worker who is dedicated to improve the future of sports, Jeremy's learned the importance of having balance in life and knowing when you need to have some chutzpah and just go for it. Here's my friend, Jeremy,

Michael Redd: This is a special cast. I've been waiting for this one for a while. I met this brother almost two years ago now, year and a half ago or so now, and we've been joined to the hip. So my brother, thank you for being on his cast today with us.

Jeremy Pressman: Thank you, Michael. Thanks for having me.

Michael Redd: Yeah, Jeremy, it's been a long time coming and me and you've had many conversations. I want to thank you again for being on this podcast to talk about betting on yourself. Explain to me your perspective and what it means to you to be betting on yourself.

Jeremy Pressman: I think it goes back to me, it's something that I've focused my entire life on. I grew up outside of Philadelphia in Trenton, New Jersey. At a very, very young age I was one of those kids who was pretty good at school, but I just couldn't do things to the absolute conventional way.

Jeremy Pressman: I think my first encounter with betting on myself was coming home in second grade and telling my parents that I wouldn't eat in their house unless they made it kosher. Since then I've been on an Orthodox Jewish track, but that was probably the first instance of coming home and saying, I'm going to do things a little bit differently over here.

Michael Redd: Wow. Talk about that experience. I mean, you've talked about that a number of times. Where'd you get that from, that inspiration from, was it from your parents or your dad, your mom, who just really encouraged that and inspired that within you?

Jeremy Pressman: So certainly my parents were the type to encourage us to be whatever it was that we wanted to be. I think that was key in enabling me to take that leap of faith, so to speak at such a young age, really second grade. I had gone to a small private school and really found that I connected of deeply with the teachings and the word, something you and I talk about an awful lot. And just felt like it was something that I really needed to start doing then and there, even if it was a little bit different than what I had grown up with.

Jeremy Pressman: Thankfully I had amazingly supportive family. Mother and father, and my sister joined me on that journey. A second and a first grader dictating what the food in the house would be was, I think, probably an interesting and unexpected outcome of winding up at that school to my parents. But here we are 30 years, not 30 years, 25 years later still doing it.

Michael Redd: Yeah, man, well talk about real quick about that transition from Philly, where you learned so much athletically just in life, the culture in Philly, to then making the bet to move to Israel.

Jeremy Pressman: Wow. That's a big one. So I guess it was in college when I started, I took basketball pretty seriously in high school and I was a pretty good athlete. Not quite your level, Michael, but I was all right. And had the opportunity to spend a year right before college in Israel in a gap year program in Israel, right outside of Jerusalem. That was for me an eyeopening experience to just how big the world was.

Jeremy Pressman: I was pretty well-traveled within the US. I had done one or two Europe trips, but seeing Israel and how diverse it was and getting the opportunity to continue my dream at that time of playing professionally seemed like something that would be a good use of time. I was newly married at the time and can't say that I have anything other than an amazing partner that was incredibly supportive. I think that's been a theme and motif throughout my life, is just people that really believed in me to allow me to take those big bets.

Jeremy Pressman: She said, "Sure, let's go for an adventure." So after finishing four years of college basketball in New York City and being newly married, going to my in-laws at the time and saying, "I don't really have a plan, I got an agent. We'll probably get on a team once we're there, but it's Israel. It doesn't work like the rest of the world, you mind if I jump?" And they said, "Sure, go for it."

Jeremy Pressman: I think that was a Sunday, with my amazing wife. Who you know, Michael. Alessandra said, "Let's go." And by Thursday we had moved overseas without much of a detailed plan, but having the general guiding North Star of we were going to stay here for a bit and give professional basketball a try.

Michael Redd: Yeah. Alessandra is absolutely one of my favorite people in the world. We'll get to that in a little bit, because you're an incredible husband and father to your children. So you make the bet to go to Israel. How important, and you just mentioned it, Jeremy, which is powerful, how important is it to have people around you to believe in you when you can not necessarily believe in yourself?

Jeremy Pressman: To me it was the most important. I think that a lot of times throughout life, even the best achievers experience a lot of challenge, especially when you're trying to push the envelope and do things that weren't done. For me, the motivating factor in why I could not fail at my mission was that when I was growing up, there was not an Orthodox Jewish basketball player that had made it professionally. At least not one that I had heard of in the States.

Jeremy Pressman: You talk about role models, to myself like yourself and as a basketball player in my world, it was Tamir Goodman at the time, but he was still paving the way in college, and very grateful and thankful for him to have done that. But I realized pretty early on that the people that I would best connect with as a young kid growing up were not the academic professors or the doctors that my dad was friends with or the lawyers or the teachers even. It was the athletes.

Jeremy Pressman: So I saw the platform, I saw the ability to really go ahead and make a much larger impact and have a pretty large sphere of influence and thought that this was something that was bigger than me, something that needed to happen. I felt like it was my duty and obligation to try to max out the potential. You go through a lot of ups and a lot of downs on those types of journeys. But when you have a big, big vision, not really a great idea of how to execute, which is going back to themes and motifs in my life.

Jeremy Pressman: I think that that pretty much summarizes it. It was beyond important to have incredible support networks and people who believed in you. For those moments where you're feeling like this is the end of the road, or maybe I should have taken a left turn here or right turn there, it's those critical moments and you don't always identify them while they're happening. You can usually look back and say, oh, that was important. Or man, if I didn't really have dinner with this person, that wouldn't have happened.

Jeremy Pressman: So, it's been incredibly helpful in my life and instrumental. The relative success that I've had thus far on this journey has been surrounding myself by people that believe in me as much as I do myself, if not more.

Michael Redd: That's amazing, man. You mentioned Tamir Goodman. That's how me and you met. I went to visit Jerusalem a year and a half ago. Tamir said, "You ought to meet Jeremy Pressman." We met each other and it's been life changing for me from that time on. If you never have been to Israel for all the listeners, you have to go because it will absolutely change your life in so many ways.

Michael Redd: One of the great things that have come out of Israel is our relationship. For those who have been listening to this podcast, Jeremy is an incredible basketball player. So he's being humble about it. We had the opportunity to play last year and I was able to see the real Jeremy Pressman on the court. You're competitive, man.

Michael Redd: It's interesting because when you think about it, you are an incredible basketball player, but then you transitioned while in Israel to being a venture capitalist. Talk about that bet, from being a hooper to now then going into high structure finance and into the whole venture capitalist world.

Jeremy Pressman: Yeah. That was a big one. Early on in my basketball career, probably second season, my wife and I had a sit down, had a conversation about basketball's great and an amazing opportunity to fulfill this dream, but it's something that has a lifespan on it and an end. Everybody has to retire from basketball at an earlier age than I think they would hope, especially when they start their career.

Jeremy Pressman: So this is my second season, started looking around at what Israel was good at and saw the Israeli tech scene is second to maybe Silicon Valley, but really world-class and wanted to get involved. So in the second season started thinking, well, you know what, I'm not the kind of guy that can sit around and do just one thing. I always wanted to have a good balance, whether that was between school and some of the observant learning I was doing and playing basketball.

Jeremy Pressman: I felt like it was time to add something else to the mix in terms of trying to propel myself professionally forward. Then going back to the network and trying to just surround yourself with great people. Wound up getting connected by one of my former college friends who had a brother here in Israel and said, "You have to check out what John Medved is starting," and Zach Miller at the time in OurCrowd, which is going to be totally disruptive to the way that startups get going in Israel.

Jeremy Pressman: That was late 2012, early 2013. I kind of came in there with the basketball players mentality of just get me on the court and I'll know what to do. Still remember showing up to the interview and expecting it to be kind of like high finance would be in New York because that's what my background was at the time.

Jeremy Pressman: Really not having a clue about the asset class, if I'm being honest with myself and just using what I knew as an athlete. Which was that it's very hard to outwork me, that I was totally willing to do any and everything to get a foot into the door. This seems like a really awesome group of people with a clear vision on how to expand on a really big problem in the market at that point in time.

Jeremy Pressman: So came in there as most people do in a startup, taking on a chunk of responsibility in an area that I didn't fully understand, but figured I would just surround myself with the best people. Then again, took that bet that thankfully I had basketball at the time. So it was just a matter of putting myself a hundred percent in and seeing if this company was able to grow.

Jeremy Pressman: Thankfully that company, OurCrowd is still around today, it's Israel's most active venture investor. It's got about a billion and a half dollars out to several hundred companies and 20 some funds at this point. So it turned out to be a good bet. It was a lot of extra hours in the beginning when we were building that business. It takes the same kind of commitment and dedication that it does to be an elite athlete. You have to be very good, very lucky.

Jeremy Pressman: You need to have the right time and you need to have the right skillset. You need to be a team above all else and really be able to put together the different pieces that come as the business grows and changes. That group was able to do that, I think probably the best in Israel and I'm honored to have been a part of it.

Michael Redd: Just an amazing story. Jeremy, of the nation of Israel. Having read the book Startup Nation, I didn't realize that one-third of the book was about John Medved and what you guys were achieving over there. I had the privilege and honor to be a part of OurCrowd's tech summit in February, this past February, and saw the reach of this summit and conference.

Michael Redd: It's just amazing what's happening over in Israel, like you said, is second to none. The innovation, the creativity. Talk about what's happening in that region from not only being a startup nation to now being a scale up nation.

Jeremy Pressman: Yeah. Great point, Michael. So in the last couple of years, what Israel has become good at has been not just taking the singles and doubles, the quick hits, building a quick technology infrastructure that could change something, selling that to an American, European, Asian based company that would then go ahead and grow that very large. What Israel has taken in, in its second phase has been what you've been referring to as the scale of the patient in terms of taking some of these brilliant minds here that think about problems very, very differently.

Jeremy Pressman: I think maybe the best way to explain it would be through an example that I had in my first minutes on the professional basketball court. It was nine years ago now and I got my first minutes and I saw the big man was just setting a moving screen. I just was not about to get crushed by a guy twice my size, setting a moving screen. I realized that the game in Israel was very, very different than the game in the States where people were a lot more physical on the outside and a lot different, softer on the inside.

Jeremy Pressman: So he went to set a screen on me. I saw the ref wasn't looking, I punched the guy as hard as I could straight in the chest. He went down, the ref called a regular foul. I didn't get tossed out of the game. I realized, man, the mentality here is just different. It's okay to do things that are a bit out of the box. It's okay to think differently.

Jeremy Pressman: What that manifests itself in these entrepreneurs and the way they think about their businesses is they really believe there's this guy, he wasn't NBA quality or caliber or anything, but he was like the world revolves around me. I'm going to set the screen, and I wasn't going to have any of it. I had, what's called the Israeli chutzpah a little bit to try, take a shot at this guy and see what happens.

Jeremy Pressman: So you're encouraged here to have that chutzpah, to say it is about me. It is about taking that risk, so to say, that you were discussing before. What's the worst that happens? I get thrown out of the game. I get thrown out of the league. Great. I'll go find another place. You're not encouraged, at least I wasn't encouraged, in the States to take those types of risks, to take those types and accept those types of failure.

Jeremy Pressman: You're taught to be a little bit more cautious, to climb a corporate ladder. Some of the people on your previous podcasts have said to choose places like Harvard, if you get in. Here, you're taught that you should, and you can go ahead and fail and fail time and time again, it's a good character building experience. As an investor here in Israel, if we see a company or a guy that's raised money or a lady that's raised money previously, and that endeavor has failed, it's not necessarily viewed as a bad thing here.

Jeremy Pressman: You are encouraged to try new things, to try to continue to push those limits. Sometimes you wind up punching the guy in the chest and they call it technical foul, or flagrant. You get fined and you get thrown out of the league. Other times they don't even call anything. So I think that that mindset shift of ability to fail is not a bad thing. It's something that is required to succeed here.

Jeremy Pressman: That chutzpah that Israeli people have in terms of thinking that yes, yeah, Google did that. We can build it better. That's what foams up and becomes the innovation that is so different here than it is in other places in the world. When you talk about taking that to that next level, I think at first there was kind of this general satisfaction of, oh yeah, we created ICQ, which is like one of the initial messaging app, not even apps, but messengers back in the day.

Jeremy Pressman: To now, it's creating multiple technologies at any point in time in this country that are billion dollar plus ones. So I think that that mentality has been taken entirely to the next level where it's like, now we're on the court, now we're going to see what happens. So I think that that's been a bit of the change we've seen here in Israel over the last couple of years, really five, six specifically.

Michael Redd: I absolutely love the mindset over in Israel. The way they, and you all have embraced failure is really powerful because if you engage it right, innovation and creativity can spring up. I think a lot of times we're hesitant to engage it because of the perception of failure. So I think you summed that up beautifully. It's interesting to me that a lot of entrepreneurs and leaders over there, of companies or startups actually come from the IDF, is that correct, Jeremy?

Jeremy Pressman: Oh, absolutely. Absolutely. There's certainly a culture here that it almost doesn't matter where you go to school. It's what IDF unit were you in. The one that's one of the biggest producers of talent in this country is called the 8200, it's an elite information unit. They tackle real time and real world problems.

Jeremy Pressman: Then you spend time with a bunch of really talented young men and young ladies. Afterwards, those are your brothers and sisters and you go on and you say, hey, I did this at age, 18, 19, 20, 25, if you stay on a little longer. That worked really, really well and had zero margin for error. Let's take that and apply that same concept to this commercial idea.

Jeremy Pressman: Or on the other hand, I think one of the other things that really is a key ingredient to success out of those specific units is that you're giving an 18, 19, 20 year old the responsibility for sometimes hundreds or even thousands of people in terms of their direct reports. So you wind up in a situation where it's much less, you're learning academics, and then you apply it to an internship or a job. That is still an important piece of the path that you need to take.

Jeremy Pressman: But what comes first and predates that is post your high school, you go and you get thrown straight in to trying to learn how to do things like management and operations. You get people that really come out with strong bases and backgrounds and at very, very young ages, who've held a lot of responsibility in their lives, who bunch of them have elite technology backgrounds. But I think that that mix and melting pot really winds up being a great cultivator of innovation.

Michael Redd: As far as partnerships go, and you may laugh at this, do you determine your partnerships based off how they do on the court?

Jeremy Pressman: I know what you're referring to. Oh, man. I think that the game of basketball to me has been a great teacher for business. We can do a whole separate podcast about that, but yeah, absolutely. I think that to make it to any level of collegiate basketball, your chances are pretty slim. I don't know the exact statistics in the States, but I'm going to bet as a venture capitalist, that's basically what we do, it's probably one in 25, one in 30.

Jeremy Pressman: Then to make it to that next level of professional, is even fewer than that. I don't know what the numbers are. But basically what I realized, probably took me to being in venture capital for three, four years, that the process is exactly the same, that we're trying to do instead of technology scouting, it was basketball scouting. Then when I realized that I had personally been through that process and had friends like yourself that had made it to the NBA. You're like a five million to one return. You're investing in Google early.

Jeremy Pressman: Me, I'm the investing in a startup you haven't heard of that had a nice exit. That's how I was able to wrap my head around it. Once I realized what I had learned in basketball, even just about the key importance of team. You've been part of probably arguably one of the best basketball teams ever assembled, Michael. We talk about this all the time. The individual parts there were some of the best players the world's ever seen, but together that team outperformed what would've gotten if you scored them in 2K.

Jeremy Pressman: So for us, we look at entrepreneurs exactly that way, in teams that have the potential to outperform. Is extremely key to us in how we think about our relationships, where we choose to partner up and invest not only our capital, but our partnerships, as you mentioned in our time where we choose to add our relationships and our value. So bottom line is yes, a lot of the investment framework that I have, or we have as a fund comes from what we know in the game of basketball as well.

Michael Redd: So many parallels, and you transition from one team with our crowd to now being a partner at Advantage. Advantage is a sports tech fund partner with OurCrowd and the Adi Dassler family. You can get into the whole legacy of that, Jeremy, when you get a chance. But the sports industry and sports market is growing. As you know, 80% of the world are sports fans. Talk about that partnership with the Dassler family and this future of sports.

Jeremy Pressman: Certainly. So it goes back to that principle, Michael, of just trying to surround myself and our self at OurCrowd, with the best people in any specific industry. When you ask most people around the world, what does Adidas stand for? Or Adidas, as they would say, most people say all day, I dream about sports. All day, I dream about soccer. It really stands for ADI Dassler. That was the founder of Adidas.

Jeremy Pressman: He had an idea a hundred years ago to create a sports shoe. That was innovation in the early 1900s. Fast forward a hundred years, his family was very concerned that people really knew the brand that he had built. But very few people understood that it was Adi Dassler who built this. You have a world famous name and a disconnect between the entrepreneur who built the business.

Jeremy Pressman: So they said, what would he do if he were around today? They came, Alex, Horst, Stefan, Christoph, all of our partners on this endeavor, said, he'd be investing in people just like himself. People who were looking to change what the future of sport would look like. People who at this point in time, they'd be, oh, that's crazy. Why do people need buy sports shoes? You can just buy regular shoes. That was a lot of the feedback they got when starting the business. It seems trivial, but apparently that was a big thing.

Jeremy Pressman: So when we look at today's initiatives and opportunities, they try to take a very similar focus. I think we came up with a couple of main principles around what he would be investing in. The first was that it would be global. We shouldn't be limited in terms of scope looking only in Germany or only in Israel or only in the US. Sports is global.

Jeremy Pressman: The global sports market is a $1.3 trillion a year business. There's plenty of room for innovation there. Also happens to be one of those businesses that's been a little bit old school, where things have taken a little bit longer to adapt technology, but now they're adapting it at an unprecedented pace. So that was number one, it has to be global.

Jeremy Pressman: Two, was that it had to be meaningful and early enough that we could have and make a real difference on the business, imprint on the DNA. Just like Adi was imprinting on ultimately what would become the athletic apparel industry. That's something that was also very important to us. We've identified a few areas that we think are really primed for growth. It starts off by thinking about what hasn't changed in a while or what seems like it'll never change.

Jeremy Pressman: I think that up until pretty recently, the TV viewing experience was you sit on a sofa, you get some popcorn, watch a game with friends. Then all of a sudden the cell phone came along, second screen. Now all of a sudden people aren't watching whole games. They're in between this and that, peeking at it for five minutes. So that was a very broadcast-heavy, dominated by major players dictating your experience as a fan.

Jeremy Pressman: We think that's all about to change. Everything's going to be totally personalized. You and I are going to be not having a sit back and relax. We're going to be involved in the experience of the game, to the point where you're not going to call it watching. So we look to technologies that can change that.

Jeremy Pressman: I guess one example of something we invested in before the fund of that was a company called Replay Technologies. Which I think everybody now knows is Intel Sports that provides where if somebody is going for a dunk contest and they freeze and do the 360 degree rotation of the cameras, that's what it shows.

Jeremy Pressman: So why should that be limited to Replay? Why shouldn't we be able to watch the game from whoever's eyes we want right now? You know what I mean? That's the future. Then serve customized experiences accordingly. So that's one area how the fan experience will change.

Jeremy Pressman: Second area we look at is connected athletics. I think with COVID, gone are the days where everybody goes to the gym, works out, comes home. Fitness is going to be more interconnected. It's going to be something that you do in your house, at the gym, on the go. The rise of things like Peloton, I think make this a lot more prevalent in mainstream. Or Lululemon buying a mirror for a half a billion dollars. This is kind of like the beginning.

Jeremy Pressman: Those are content platforms that go on to fixed equipment effectively, allowing you to have those experiences. But we're still early days for what that can be. That's also going to be incredibly holistic going forward and catered to you and what's best for you individually.

Jeremy Pressman: Then the third area we look at is possibly new categories for sports and that's anything from e-sports to new games entirely. I think on a different panel, which we spoke together, Michael, I think you made a prediction if I'm not mistaken that in the next decade, the most popular e-sports player will be more popular than LeBron. Is that right? Do I remember that correctly?

Michael Redd: Yeah, I think so. We talked about that in February, virtual athletes, digital athletes.

Jeremy Pressman: Yeah. So the rise of digital athletes has absolutely made known, and now is more accepted. That e-sports is not something that you do in your basement and you don't want anybody to know about it. This is a booming industry in and of itself. That's the last area that we think has the ability to change at a rapid pace.

Jeremy Pressman: So those are the three areas we invest in. Again, it's got to be global. We like that angle. And also key importance to us is that it's early enough we can impact the DNA and use our networks to be helpful.

Michael Redd: Is there a migration from traditional sports to e-sports?

Jeremy Pressman: Migration? I think it's probably more of like a cross pollination. I don't think necessarily that people who are sports fans are bubble or not come next to year, are going to stop watching sports entirely and move over really entirely to watching things like Fortnite, et cetera, streaming it. I think that you're just seeing that it's much more mainstream than people were giving it credit for.

Jeremy Pressman: Again, we've been looking in parts of Eastern Europe, Korea, et cetera, this has been a trend for 20 years. This is nothing new. It's hitting the States, North America, even to some extent, Israel harder right now with these just eyeopening numbers in terms of engagement. They haven't figured out exactly how to make real businesses out of these yet with the exception of the publishers, the rights, the [inaudible 00:30:05] of the world. But I think that that's also going to change too. So we're excited about those areas, for sure.

Michael Redd: I'm excited about being a part. Obviously knowing you for the last year and a half, as well as the Dassler family, they welcomed me in and it's been incredible since the time I've met them. Learning so much about advanced analytics and positional data and how that's going to impact sports, which is near and dear to my heart as a former athlete. Totally get the improvement of athletes, quality of their career, the longevity of their careers. So it's a powerful, powerful platform that I'm so proud to be a part of, man.

Jeremy Pressman: We're honored to have somebody like yourself who understands and has used a lot of the technologies when you're playing. It's amazing to see how these are going to be rolled out to youth athletes and to weekend warriors. I think that that's a really big part that we're super excited. As we talk about the importance of assembling a world class team to have you involved, it's just a huge honor to us.

Michael Redd: No, it's the same here. Same here, buddy. I won't keep you much longer, but I do want to talk about the family. I know you're a major family guy and just your wife, how she's been so supportive and the children. I've done Shabbat with you over in Israel, which is one of the most powerful experiences. Talk about the family, man, and the work balance, family work balance.

Jeremy Pressman: That is the biggest challenge. I'm incredibly blessed to have an amazing wife who we haven't talked about her athletic abilities. She's the number two ranked woman in the US in a martial art called kenseido, that her father brought over from Japan. But incredible athlete in and of herself.

Jeremy Pressman: She's been the driving force behind anything and everything I'm able to do in terms of just supporting. Like we spoke about a little earlier, supporting the move to Israel in the first place or chasing the dream of playing basketball or quite frankly, two years on the road with the fund. So she's been absolutely incredible. We have three little boys who you've met, Michael, who are extremely energetic and love to keep us busy and on our toes. But family is the most important piece. Without that the rest would fall apart, certainly.

Jeremy Pressman: In terms of balancing time, I think it's important to recognize and enjoy each of the stages. The kids grow up very, very fast, as you know, just trying to make sure to spend time with them on their appropriate levels and the wife as well, especially during quarantine. I mean, it's been, I don't know, 10 years, since I've been at one spot for this much time. So it's been awesome to spend time with my lovely and amazing wife, seriously. Yeah, family, like I said, at the beginning of that question, the family is really the most important part of anything. Without it, none of this would be possible.

Michael Redd: You mentioned COVID. What's your advice to startups, to entrepreneurs in this new normal, new reality because I think there's a tremendous opportunity in the midst of all of this for innovation and creativity. What are you seeing or what are you saying to startups and entrepreneurs?

Jeremy Pressman: Yeah, I totally agree. Embrace it. This is here. This is the way it's going to be for the foreseeable future. If things change, which I think we're all hoping that there will be a quick end to this with a vaccine, we'll find better things to do than to quarantine and to isolate. Hopefully we can get back to some semblance of normal. But I think there is a change in human behavior that is been on its way since before COVID and COVID has accelerated it in certain circumstances.

Jeremy Pressman: Like the move towards pieces of remote learning or remote working. Do I think that 10 years from now, we'll all be [inaudible 00:34:19] and totally sitting at home, taking online classes? No. But I think that the model of the 40 hour work week per se, where you got to show up and clock in and clock out, that's probably behind us.

Jeremy Pressman: So when you're talking to startups, especially early stage ones, it's remembering that there are going to be COVID specific opportunities. But what we're more interested in as longer term investors is that you have a plan that is not purely contingent upon, hey, this is a COVID plan. This is what works exactly during COVID. You need to see a little bit further down the line than that.

Jeremy Pressman: I think also just being understanding. There's going to be immense challenges and not being able to go out and meet your big clients or meet your new potential partner or investor. It's an embracing that things are going to be changing. If you asked me before COVID, would we ever invest in an entrepreneur we never met in person? The answer would have been no way. Are you kidding me? How are we going to do any of that?

Jeremy Pressman: Would you ever scout somebody to the league that you've never actually seen play in person and only seen in video? It seems nuts, but that's the reality of today. Will it pass? It probably will pass. Will it have changed things? I think it will. So just trying to stay levelheaded and balanced between taking advantage of the opportunities now while keeping a longterm balanced approach as well.

Michael Redd: Man, that's beautiful. It's beautiful, brother. As we close, man, what would you tell your 16-year-old self, looking back?

Jeremy Pressman: Wow. My 16-year-old self, looking back, it's going to be a hell of a ride, and try to enjoy it while you're there. I tend to be a person that's always thinking about the next thing, as you know, Michael, you've seen me do this many times in person. Really just enjoy the moments as they are, dream big, do not be afraid to fail.

Jeremy Pressman: I wish I would've known the Israeli mentality while I was playing basketball in the States. That would have helped a lot. And be very grateful and thankful. You're a very lucky person to be in a great spot and make sure to maximize that potential. I think that that's advice I'd give any 16-year-old, is really dream big and don't let anybody else define what your dreams should be.

Michael Redd: Perfect, man. As I think about the social unrest around the world and particularly in America, I think about our time in Berlin last year, last November, October. Me and you were over there for our lead accelerator demo day. It was an incredible time over there. So you have you, Jewish rabbi interviewing an African American male in Berlin, Germany 30 years after the Berlin wall comes down. It was such a moment.

Michael Redd: Me and you went to lunch afterwards and had to reflect on that. I think our relationship should be an example to how the world should be. I don't mean that arrogantly, but I think our union, our connection, hopefully it can be a light to the world.

Jeremy Pressman: Absolutely. That was an incredibly powerful moment for me. That was also, I think the 80th anniversary week if I'm not mistaken, of Kristallnacht, which was the beginning of the Holocaust really 80 years back. My wife's family was very, very impacted and affected by that. So, being able to stand there with you by my side on TV with a yamaka on my head and I've been on TV enough times where I'm the only guy standing there with a yamaka.

Jeremy Pressman: But with you, that felt like one of those powerful transformational moments where it wasn't about you and me. It was about a much bigger vision. As you said, I hope we can shed a bit of light on times where there seems to be a little bit of unrest and just hopefully people can get together around the light that we can bring instead of focusing on other things. That would be fantastic.

Michael Redd: It was on national television. That's right. All over Germany. That was a special, special moment. My brother, thank you for being on this podcast, man. You know I love you and your family and so appreciate all that you've taught me all of last year and a half. I'm looking forward to an incredible future together, man.

Jeremy Pressman: Likewise. Love you too, Mike. Thanks so much. Appreciate you having me on.

Michael Redd: I love Jeremy's passion and excitement, and I hope that his message of staying true to yourself and not being afraid to fail resonates with you. Thanks for listening to today's episode. To read the show's notes, learn more about my work, or connect with me, visit MichaelRedd.com. New episodes released every week on Monday. So make sure to subscribe if you want to stay up to date. Until next time I'm Michael Redd. Remember, you are the secret to your success.