Caleb Zipperstein: The Big Power of Small Improvements

Caleb Zipperstein: So betting on yourself really for me is about the smaller decisions and how the small decisions and when I can turn those small decisions into habits that ultimately, the larger opportunities from the surroundings will present themselves.

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. Today I'm talking with Caleb Zipperstein former Israeli Defense Forces soldier, political analyst, associate director of Investor Relations at equity based crowdfunding platform, OurCrowd and currently director of value creation and venture capital lead at the Empower Africa.

Michael Redd: In this episode we talk about Caleb's childhood, the power of unexpected emails, and his current path, as an investor, philanthropist, and world traveler. But what really impresses me about Caleb is his commitment to the people in his life, both near and far and his unstoppable passion for truth. Caleb is one of the nicest and most discerning people I've ever met. I'm incredibly grateful to know him, and I can't wait for you to hear his wisdom. Here's my conversation with Caleb Zipperstein. Caleb, I can't thank you enough for being on the podcast. I will say this about you and it needs to be said publicly, you're one of the nicest people I've ever met in my life. And Caleb and I, just a little history, met, oh, two, a year and a half ago in Israel. And you can more expound upon our time together but it's been an honor knowing you over the last year and a half and thank you for being on the show, buddy.

Caleb Zipperstein: Thank you so much for having me Mike. As I said, any chance to just, to be able to talk to you, whether it's on a podcast with all the great people out there listening, whether it's just sitting in the car somewhere, giving us some shots or sitting in a Shabbat table here in Jerusalem, it's always good to talk to you man, so thank you so much for having me. I'm so honored to be here.

Michael Redd: My honor man. It was incumbent upon me to have you on because of what you're doing and not only in Israel, but also in Africa. And we'll get to that a little bit, but as you know the podcast is all about betting on yourself and I want to kind of start with that of, when it comes to betting on yourself what does that meant to you?

Caleb Zipperstein: It's a really powerful question to me. What does it mean to bet on yourself, because I feel that a lot of the success that I may have had in life is really a byproduct of the people that I've been fortunate to surround myself with, where it makes it so much easier to do things when you know that there's an entire community surrounding you that has your back. I mean, I'll admit Mike, we haven't talked about this much yet but you're one of the nicest people that I know by far, but really I get a lot of inspiration lately, actually from your wife and her incredible Instagram and her incredible awareness. I mean, even through the pandemic a little bit before, and again we haven't talked about this much but I've struggled a little bit in life with self esteem. I'm not necessarily at the caliber of having reached some of the achievements of some of the other guests, and I'm not really want to say that I've bet on myself in a big way, or that it's really paid off.

Caleb Zipperstein: Maybe that's just self esteem or it's just having not yet reached the full potential that I believe I can. But, I mean, again, I definitely feel that I must have done something right along the road because it can't just be pure luck and HaShem, God working his magic that leads me to a point where I have you as a friend and I get to have a chat with you and hear and share perspectives. But in terms of betting on yourself, most of the times in my personal life and in my work life when I felt that I was about to do something sort of, to the tune of taking a big bet on myself. Whether it was times when I wanted to go out and start my own venture, which I haven't done yet, or take upon a massive intrapreneurial investor, endeavor, sorry within one of the entities that I work, even propose to somebody or take a relationship to the level, I usually kind of look at myself as having rescinded the power that I had in that situation back to the hands of somebody else.

Caleb Zipperstein: So when I think about that for me betting on yourself isn't necessarily about the big decisions in life. Because as mentioned I do feel I'm incredibly blessed, but the betting on yourself decisions for me are about the small decisions every day that are really important for consistency. And in periods of my life where I bet on myself in making small decisions the larger opportunities and more sort of monumental successes have really, more or less just kind of presented themselves, I've been kind of opportunistic. Betting on yourself is waking up in the morning and instead of going directly to your phone and look at your messages, your emails, just to have faith that the thoughts in your head and the feelings in your heart are going to bring you more simulation and satisfaction. Betting on yourself is knowing that if the morning forecast is going to be cold and rainy.

Caleb Zipperstein: It's going to be ugly outside and you're tired, you're going to show up to that surfing lesson or to that basketball workout, because you know eventually that you're going to enjoy yourself and you're going to savor that incredible feeling of exhaustion or catching a wave and positive feeling will sort of overcome any doubt and discomfort that you might have leading up to it when you're kind of doubting yourself. Betting on yourself is visualizing yourself in a spot where you want to be with the people and you have gratitude rather than being critical of yourself in a moment for not exactly being where you think that you should be. And I think it's really just about the balance between kind of the micro and the macro, I'm working a little bit more on the macro now.

Caleb Zipperstein: You've helped me a lot with that Mike, through our relationship. Our mutual friend Jeremy Pressman has helped me a ton with that. As mentioned your wife has helped so much, I haven't even met her, but just her inspiration has shared so much of that degree. But the macro I think really kind of requires you deciding what you want to do and visualizing yourself. And so betting on yourself really for me is about the smaller decisions and how the small decisions and when I can turn those small decisions into habits that ultimately, the larger opportunities from the surroundings will present themselves.

Caleb Zipperstein: But again really, for me, above all else, any betting on myself that I've done has been because I've really felt the love and the support and the confidence of the community that I have around me and that I'm so blessed to be a part of. So it's not as much as betting on yourself but it's understanding and having that strong feeling in your heart that other people are betting on you therefore you have to bet on yourself.

Michael Redd: Okay, I didn't announce you appropriately, we are speaking with a sage today, ladies and gentlemen. [crosstalk 00:08:40] sage, wisdom and sound man and authentic man and so appreciative of you mentioned my wife as being such an inspiration. She certainly is to me every single day. And so that's profound man, as far as just the everyday foundational bets on yourself with all the examples that you used serve as a launching pad into the other opportunities that come from a macro standpoint, I think it's profound man.

Caleb Zipperstein: Thank you.

Michael Redd: And I think self discovery is just as profound as self denial and falling in love with yourself, not out of an ideologuous standpoint but just loving you, taking bets on you in those areas that you mentioned are just so prolific man. From my knowing you for the last year and a half I've certainly and hearing your story I've certainly believed that you've taken major bets over the years. Talk to me about growing up and also is there a pivotal moment in your life where you said, wow, this is a major risk.

Caleb Zipperstein: Well, thank you. Thank you for saying that Mike, it really means a lot coming from you. And yeah, it's in those moments where we're taking a lot of bets on ourselves in the micro that the macro really does present itself. We talk truth all the time and I don't, we haven't discussed this that much yet Mike, but in addition to of course my love of Judaism, and the teachings of Torah, and Israel. Lately, through some of my work I've been exposed to some African proverbs and one of them which I've read recently states that a man who is loyal to his truth will be expelled from nine villages along the way. So I really just do feel that it's going to be hard, and it's not going to be seamless when you're sticking to your truth. And I've tried to inspire myself to do that when I can. And I feel that I've derived a lot of that from others.

Caleb Zipperstein: And it's interesting because growing up I felt a lot of that love from my family. I grew up in California, with a really, really wonderful family. My parents are truly some of the best people that I've ever met. My mom, she went through a little bit of adversity, she suffered from chronic pain for about 15 years. But that's not at all what defines her, and it's not really what defines my relationship with her. And my parents what was so defining of that period for me, watching and reflecting on it now, was that my father just would always say to himself and would say to us, through sickness and health, through sickness and health. And he was just so good to her and he was so good to us. And even though it was challenging for my mom, I mean, she was and still is so athletic, Mike that I feel like she could even make an NBA roster today straight up.

Caleb Zipperstein: I don't know how good of a [inaudible 00:12:42] she has. But for somebody of her athletic stature and passion to be bed rest for a couple of years and really just push forward was pretty defining, but also just really inspiring how again, she stuck to her truth. They never gave up. They were so resilient, they went to every doctor, they tried every treatment. And then ultimately, fortunately, rehabilitative yoga was what really got her out of it. And now through some of the struggles that we sort of endured as a family through that, that was kind of from the ages of 10 to 25. So really kind of some of the defining years of my life that was sort of a piece of adversity that we had to go through as a family. And being able to support each other and to be there for each other, and really just to watch my father deal with it. To watch my mother come out of it. And to watch how my brother, my younger brother is just one of the most inspiring, cool, funny people out there.

Caleb Zipperstein: He's not the most outspoken guy, but he's really inspiring to me because he has had a great group of friends that he's been tight with since he's, I don't know, 10 years old. He was a crew athlete in high school, went to UC Berkeley. Decided at the age of 15, I'm going to be a doctor, and today I'm just so proud that he is a second year resident at UCSF Fresno in Orthopedic Surgery, aspiring to do cancer treatments within orthopedics. So I have just a really, really inspiring family. And I'm really grateful that I get to talk about them a little bit with you. We haven't had the chance to speak about them yet and it gives me a great opportunity to reflect. But they really have been an inspiration to me in terms of betting on themselves and staying true to themselves and really diving deep. They're all avid readers, they're all super smart. They're all incredibly considerate, incredibly kind, incredibly thoughtful.

Caleb Zipperstein: So I was really, really fortunate to grow up and be a part of a family like that and that of course includes all of my extended family from around the world and with what they do. My aunts and uncles have always been fun and inspiring. My grandparents, my mom's parents unfortunately passed away. My mom's mother, Mike was a Holocaust survivor, and her father was a seventh generation American Jewish man, worked in sales, this wonderful relationship builder. And he ended up meeting my grandma I think when he was 36, and they got married of 38. And it was beautiful because I was talking to my mom about sort of my journey and relationships. And she was able to remind me of his sort of experience and it was able to bring me a lot of common optimism because my grandma and grandpa had one of the most beautiful relationships. And thank God my father's parents who still are alive today, living in Santa Barbara, they also have just stuck together through thick and thin.

Caleb Zipperstein: And it's a little bit odd, because that strong family strength, I think typically should drive me to want to be close to them physically to continue to absorb. But I really feel like that family strength like what I was talking about in the beginning, which is when you have a strong support network, you do take bets on yourself. That's what motivated me to just never, not really consider themselves when I made the biggest decision of my life which was to move to Israel, which I did after graduating from university, and that was about eight years ago. I've been here ever since. This place has awarded me with so many incredible relationships and friendships and opportunities. I had a good social life in America, I had some nice friends, I enjoyed college. I enjoyed, I was actually a four year varsity basketball player, Mike. I'm not sure that we talked about that but hopefully we'll get a few shots at some point or another to see if I still got it.

Caleb Zipperstein: But really just that strong family support. And growing up in that family where I never felt any pressure I only just felt support love and inspiration just inspired me to follow my truth and get rejected a bunch and make these crazy decisions like move to Israel, and pursue initially a degree, pursue a career in diplomacy. But then have that completely side trapped where I ended up in venture capital and then flew to the Middle East, a couple times before we even had peace with the Middle East. And then go to a refugee camp in the Palestinian territory setting startups and then get on a plane to Nairobi, Kenya and get on a plane to Sierra Leone.

Caleb Zipperstein: All of that has just been a function of having this incredible family, and this incredible support network that is so strong within me that making these big decisions it's just, I really only to a flaw kind of just think with myself because they always come around and they always deliver and they always show that love and attention, that just enables you.

Michael Redd: Wow. Well there's a lot of roads to go down but I think when you talk about Israel and Jerusalem in particular, it's such a big part of my heart. Having the privilege of going to Poland a number of years ago and going to Auschwitz and doing the tour and meeting people and hearing the stories and then coming to Jerusalem. It was just a life impacting moment for me years ago, that led me to this ecosystem, as you mentioned about venture capital and what's happening from a tech standpoint that's been happening in Israel for many, many, many years.

Michael Redd: That was a novice to it, and still am to a degree but learning about what's happening with inside of Israel, to me second to none in the world when it comes to innovation and creativity and adventure, which is how me and you met through our brother, Jeremy Pressman. Who is not only my brother and not your brother but also the incredible man that works with OurCrowd and the ADvantage Sports Tech Fund. But me and you had an incredible connection and Shabbat at his house. [inaudible 00:21:12], I was able to see that as you drove me to the airport. Talk about that journey to OurCrowd, which then led you to what you're doing in South Africa with empowerment Africa.

Caleb Zipperstein: Yeah, that was amazing to think that just that email that I got one day out of the blue from a friend of mine while I was looking for jobs, saying, great job, check it out, call this guy would, well I'm just sitting in Jerusalem just... Because I got that email from OurCrowd after I had gone through a really intensive six months political internship. I was managing all of the English language activity and voter outreach for one of the largest political parties here in Israel. I was thrust into this position at 23 years old after the service, and just had so much joy and rush over just politics. And I studied political science in undergrad and I came here with the dreams of becoming a diplomat. I wanted to do everything that I'm doing today in then Middle East and Africa, but I thought that the public sector was the way to do it.

Caleb Zipperstein: And so unfortunately the party that I was working with lost the election so there were no job openings available. But I was able to get a referral to an Israel advocacy organization here and I loved the idea of that job, because I could tell stories about Israel and make a case for why people should support the country. But I was a finalist for that job, I didn't get it. And I remember sitting down that day thinking, when am I going to get a job? What job am I going to get? And then I get this email from OurCrowd and I say, yeah, I'll go to the interview. I had no idea what venture capital was at that time, Michael, this is six years ago. I didn't even, I had taken one business class in college, it was an international negotiations course. And let's just say I got soaked in every one of those negotiations, and without taking any more business classes I was like, business is not for me.

Caleb Zipperstein: But when I got that email from OurCrowd, and I went in there for the interview, there were two lines that the man who was interviewing me, Denes Ban he is managing partner and director of Asia, not Asia. I'm not sure. He's the managing partner at OurCrowd and just one of the most incredible people you'll meet. He said two things that really stuck out with me. When I asked him what makes him so good at what he does, he says, I never sell, I never push, I hang out with people. And that was like, huh. Interesting, I like hanging out with people. Go on. And then when he said, he asked me why do I want to be a diplomat, I told him because I think it's a way to bring Israel with its neighbors in the Middle East and Africa. And he says, Caleb, what if I told you that within OurCrowd, by talking about innovation and creativity and technology you could tell stories about Israel but all of those stories would be good stories, and all of those stories would be inspirational stories.

Caleb Zipperstein: And you can learn so much about business and entrepreneurship and innovation along the way. So I said, sign me up. And I joined OurCrowd working with him on some of their incredible partnerships in Asia for starters with partners like UOB in Singapore. A few wonderful families in Hong Kong and in New York. We actually worked closely with a family that you know Mike, I'm not sure that I'm allowed to share them but they're very involved with the Milwaukee Bucks actually. So just to think about how this comes full circle is just so incredible here.

Caleb Zipperstein: But further down the line at OurCrowd, I was able to sort of understand that I didn't know how to work with some of these clients. And then I started looking for opportunities to be an intrapreneur within the firm. So after working in the Asian market, I was working on the US market, where I was paired up with a partner at the firm, but I started kind of going rogue and closing a few small deals just without him really knowing. And then the company said, well, why don't you go work with our East Coast investor base? And I said great, I'd love to. So I did that. And then once they hired and set up a presence in New York, a little bit further we brought in a new director of Investor Relations, and I looked at the map and said, I want to work here and here. And here and here was London and the Middle East. So, I was able to justify a few trips to the Middle East particularly the Gulf.

Caleb Zipperstein: Had an incredible experience there, meeting investors, meeting companies, and meeting young kids from all over the world and just seeing how innovation and business building brings us together. But then I got another life changing email from an investment banker in Nairobi, Kenya, a dear brother of mine, David Mattan, who was at the time, working at one of the largest investment banks in Nairobi. And he was ready for a career jump over to venture capital. And I remember our first conversation, I really believed in the guy. And when he said, there are a lot of high net worth individuals in Nairobi, who would love to invest in Israel, I believed that there was something to it. So I brought it back to my boss at the time who said, Caleb I just convinced the CEO of the company that we shouldn't open up any sort of resources in Paris. How am I supposed to go back and say that we should open up resources in Nairobi, Kenya?

Caleb Zipperstein: I guess, that was the point where I bet on myself because I kept pushing. And we finally said okay, we're going to sign an agreement, let's try it out. Two weeks later we had a few million dollars in our bank accounts. And two months later I was on a plane to Nairobi, to try and squeeze a little bit more lemonade out of that lemon. Actually will use a sour reference but when I was in Nairobi, meeting investors by day at night I started to meet companies. And I was a little bit put off by the fact that these unbelievable companies that I met in Nairobi and then in Botswana, were asking me for a five to $10,000 check. When these guys were coming out of MIT, they had patents, they had the type of software if you saw that in Columbus or Silicon Valley, you'd be cutting multimillion dollar checks.

Caleb Zipperstein: But in Nairobi, you see the stuff and they're asking for a $10,000 check and most of them are going for aid. We talked about it's about trade over aid, and it's about the power of making an investment in one of these companies. So that kind of rubbed me a little bit of the wrong way, that there was so little access to capital. But then I also just saw that, where there's something potentially missing there's also incredible opportunity. And then further to that I saw that these people who I would be working with are just some of the most energy energized, motivated, passionate, driven, thoughtful, kind, fine, warm, welcoming people that I could work with. Because remember at this point I've worked with folks from just about everywhere in the world. So for me, I saw Africa as an incredibly just exciting business opportunity. And those two words excitement and business, and I got caught with a serious case of FOMO. I didn't want to miss out on finding a role within this venture capital and innovation ecosystem that was taking place on the continent.

Caleb Zipperstein: And Michael, it's so special that we're talking today because literally this morning it just was announced that a FinTech company in Nigeria, founded in Nigeria, just raised $170 million, bringing their valuation to over a billion. They're unicorns in Africa today, it's not that common. It's not Israel or Silicon Valley where a unicorn isn't news. But if you have a moment go on a Twitter, go on a Instagram, go on a LinkedIn and just see the price of the whole ecosystem in this company Flutterwave reaching unicorn status. This was the only company to receive around with Visa and MasterCard participating side by side. Can you imagine that a FinTech company in Nigeria is the ones that brought Visa and MasterCard to the table to collaborate.

Caleb Zipperstein: And not only that, there were going to be so many more of these unicorns that we see on the continent in our lifetime so the time is now. I don't want to miss out on these whether it's as an investor, whether it's about a facilitator of investment, whether it's as a cheerleader. And the company that I'm working with today in Empower Africa is really just trying to drive that. To drive that awareness and to drive that connectivity, which will strengthen the ecosystem by providing the infrastructure and networking tools required through a business platform for these companies to be together.

Caleb Zipperstein: But then further to that it also makes it so much easier for new investors, for new partners, for new products, for new companies to find their place within the ecosystem as well. Because I truly believe in the strength of the ecosystem, but also the power of just what will come from our collaboration with Africa, and what it'll mean for the rest of the world, not just the continent or not just vice versa. It's how the world will look like when Africans, specifically African innovators have that seat at the table. It's mind blowing, what we're going to see Mike and I can't wait for us to go there together at some point brother, and check it out [crosstalk 00:34:38].

Michael Redd: No, well I was forced to go with you last year. And obviously we have to deal with COVID but I'm coming to Africa with you. And committed to really tap into a fertile ground over there in Africa to genius and brilliance and innovation and creativity. You're 100% correct. I was completely astonished by what was happening over there. And you've been an incredible evangelists champion for that region of the world. And it's just a matter of time where it continues to explode. The few, we have left Caleb, because it's been such an incredible time with you today on this podcast. If you had to go back to your 16 year old self, what would you say to yourself at age 16?

Caleb Zipperstein: I got a couple pieces of advice for myself. The first is, like I said in the beginning, don't measure success by when you achieve the end goal but measure success by the minor improvements that you make each and every day. I've really, I thought about a lot this recently when I picked up surfing, which I started when the pandemic kind of started because that was one of my outlets. And I keep visualizing myself riding large waves and carving and carving but anytime I do something new that shows a little bit of progress I feel so great about myself. So number one would be measuring success by the minor daily improvements and not just having the end goal in mind.

Caleb Zipperstein: The second piece would be. There's no such thing as being self taught. Like with surfing as the analogy, nobody just gets in the empty waters and figures it out without at the very least watching other people do it or without any sort of coaching, or even just having, seeing a video. Actually, there's another proverb that I think of when I say this, which is wisdom is like fire, people take it from others. And another is when you're filled with pride you don't have any room for wisdom. So I really tell myself that there's no such thing as being self taught.

Caleb Zipperstein: Third, value the importance of time. I actually really remember that from your episode with Tomi Davies, which our good friend TD, where he talked about that. And the last one man is, we don't need to take life too seriously. We've all got our place in society, and it's always an important place. It doesn't function without us finding our role. So let's enjoy it. Let's not take it too seriously. Let's have fun. Try and enjoy those little moments. So we'll just smile more and then the big things will come.

Michael Redd: Beautiful, just beautiful. We talked about your past and what you would shared with your 16 year old self. What excites you about the future?

Caleb Zipperstein: What excites me about the future is, first of all, being able to travel again, being able to be together again. We're talking about, we're talking today when the world still isn't open, and where we're not all able to just jump on a plane and go see our families or get in the car and drive up to Jerusalem to see our brother Jeremy. So just being able to create those memories together in new places is something that inspires me because regardless of the pandemic or not, that's something that I intend to do and that's something that I always appreciate and it's something that I always look forward to. I'm definitely excited about improving in surfing right now. I'm excited about seeing, about reaching the day when a unicorn coming out of the African continent is not news, but it's just a thing. And I'm really excited about a future where I believe in time we, as people will be much, much, much more empathetic and much kinder to each other.

Caleb Zipperstein: I really think that with all of what we see in today's sort of world about divisions and they're very, very real. I do hold in my heart that just like we used to not know the damages of tobacco. We used to not know that some of these things were really unhealthy for us, and we stopped. I think we're going to realize that about some of the lack of empathy in our society. And some of the toxicity that's inherent. And I think that's going to go away in time. We see it with Israel coming to agreements with the Middle East.

Caleb Zipperstein: We see it with so many other different areas, whether it's on the micro or the macro level, but I feel like we're headed towards a much more empathetic kind of world. Just because some of the toxicity today we will realize that it's bad for us and we will deal with it. And I'm just excited to spend more time together Mike, to be in each other's company. You mentioned that Israel has had an impact on your life. You've had a big impact on Israel. And all of us are just so grateful to have you here. And one of the things that I'm looking forward to most in the future, is just picking you up at the airport, and going straight to one of our Shabbat dinners my brother. Yeah, let's look forward to, let's look forward.

Michael Redd: Well, I can't thank you enough man. I think what you said was beautiful, on point, thoughtful, processed and authentic to who you really are man. Can't wait to hug you, brother. And this is just the beginning of an incredible journey together. So thank you for being on my man.

Caleb Zipperstein: Thank you brother. Thank you. Really appreciate it.

Michael Redd: Man, I love talking to Caleb. His story is one of unexpected twists and turns, guided by enduring wisdom, courage, and family, sounds like a recipe for success if you ever had one. He not only bets on himself, he's a master of betting on others as well. You're an inspiration, brother. Thanks for coming on the show today. You can follow Caleb on LinkedIn @calebzipperstein. Thanks for listening and until next time. I'm Michael Redd, and remember, betting on yourself is the secret to success.