His openness to the possibility that life may not always happen the way he planned enabled Oshri Kaplan to become a successful student and venture capitalist. While he was still undecided on which career path to pursue, Oshri seized the opportunity to grow in various fields, including the military, law, and business, where he gained a network of corporate leaders and entered the venture capital industry.
Oshri started his career as an analyst in his homeland, Israel, before moving to Silicon Valley— the Mecca of VCs and startups, to continue providing value as a venture capitalist. He is MBA 2013 at Berkeley Haas and a seasoned investor who later joined Munich Re Ventures as an Investment Director.
Learn about the challenges of finding investment opportunities, the day-to-day activities of a venture capitalist, and which class at Haas helped Oshri advance in his entrepreneurial career.
Which class at Haas influenced you the most?
[00:08:36] The most influential course I took at Haas was negotiations with Holly Schroth. I’m negotiating now every day. My job is essentially to negotiate. So with that, I don’t think about any other course that I would rather take a test than the negotiation. That was eye-opening because, as an Israeli, they’re teaching you tactics around negotiation, which I found very different from the tactics taught in US-based schools and definitely at Haas. That was super refreshing, and it was hard. It was hard, and it was challenging at the beginning to find myself in situations where I needed to adapt. I need to figure out a different way to approach things if I want to be successful. That’s one of the classes that I’ve been using since then.
What does a venture capitalist’s day-to-day operation look like?
[00:16:56] In general, an investor needs to divide his time between looking and listening for new opportunities; depending on what exactly is your role, whether you are in one of those funds or principal and later, director or general partner, you need to manage your time.
His advice to fellow Haasies or other students who want to have a successful career.
[00:24:39] I think people need to be vulnerable. They need to open themselves to the ideas of what they are going to see and learn and be open-minded about networking and the people that they’re going to meet during those couple of years or three or four years at school, as those are the years that you don’t really know who you’re going to meet. You don’t know where the next opportunity will come and how you’re going to meet your next employer or a reference to a new employer. I always had a plan in my mind, and I needed to follow it, but the reality is that nothing really went according to the plan, but it was parallel, and I was open enough to expose myself to other options.
(Transcripts may contain a few typographical errors due to audio quality during the podcast recording.)
[00:00:00] Chris Kim: Welcome to the OneHaas podcast. I’m Chris Kim. Today we have Oshri Kaplan, Investment Director at Munich Re Ventures, and a 2013 Berkeley Haas MBA alum. Munich Re Ventures is funding the future of risk for human endeavor, working across the globe to support the next generation of disruptive technologies and business models. Welcome, Oshri, and great to have you on the show.
[00:00:28] Oshri Kaplan: Hey, Chris. Thanks for having me. It’s always a pleasure to get connected with Haas and Cal and reconnect with Haasies. So, Go Bears!
[00:00:35] Chris Kim: Go bears! I’m super excited to have you on the show today. Could you maybe share a bit about your origin story? You know, where did you grow up, and did you always know, even as a kid that you’d be a venture capitalist?
[00:00:46] Oshri Kaplan: Yeah, as you can still feel by my accent, I’m originally from Israel and I was growing up in a small town near Tel Aviv. And after finishing high school, I went to serve in one of Israel’s defense forces intelligence unit.
[00:01:00] Chris Kim: Awesome.
[00:01:01] Oshri Kaplan: And I essentially started my career there, so to speak as an analyst. And that was my first job as an analyst. Little did I know that I guess I will analyze technologies and companies for the years after that for a living. Then four and a half years later, basically after I finished army service, I got convinced by my uncle to go and study law. Don’t ask me why, but I got convinced and I wasn’t sure that was what I wanted to do, or this is the ultimate path for me. So I decided to merge that with some business knowledge. So I also did an undergrad in business, at Reichman University in Israel. And towards the end of my second year there, I realized that I feel much more connected to the world of business than to the law side of things. And I decided that I’ll start to explore some opportunities on the business side. I didn’t know what these venture capital or hedge fund were, to be honest with you at that time, it was really a beginning, but somehow I got in the intro to one of Israel’s most famous venture capitalists at the time. And I went to meet him. And that was in the summer between the second and the third year of my studies. And I guess one thing led to another and I find myself doing a summer internship in this VC firm. And also spend the next couple of years there. So that’s where I really know that I want to continue and do that for my career, So I still finished my law degree, but you can call me a defective lawyer after that. So I continue to do my part on the business side and continue this VC role. And I haven’t left the VC world since then.
[00:02:32] Chris Kim: Oh, my gosh. That’s awesome. What was it like growing up in Israel? And what was that like growing abroad and then eventually coming to the US for school?
[00:02:40] Oshri Kaplan: You know, I think Israel is not that different than the US when it comes to technologies and the entrepreneurial system, and even the VC, to be honest with you. I think what was very clear to me back in the day is that to go here and to continue my career in the VC side of things, I need to do it in Mecca for the VC startups.
[00:03:01] Chris Kim: Gotcha.
[00:03:02] Oshri Kaplan: And I knew that I want to do it here in the Valley, where still to this day in my mind, I realized that the path here to Silicon Valley as a foreign businessman could be for a graduate degree, mostly in business. And I also noticed that most of the VC leaders out there have an MBA, they have some leadership roles in some of the other technology companies and I say, well, how do I get to that? And to me, that was very clear that an MBA could definitely expedite this growth for me. And I knew I wanted to do it in schools that definitely focus on leadership and entrepreneurship and VC. And to me, Berkeley is completing all of this together.
[00:03:41] Chris Kim: Oh, that’s awesome. What was that hard? If I understand correctly before you came to the MBA program, you were working at Deloitte, right? I think a lot of people would say that’s a great job. It’s a lot of opportunities and it’s maybe hard to come off of that track. How did you end up ultimately deciding, Hey, you know, I want to make the shift and I’m willing to take the risk? And then how did you decide, specifically about Haas? Did you consider other places or what was that process like for you?
[00:04:06] Oshri Kaplan: Yeah. So I guess to me, getting to Deloitte you know, I think Deloitte was a great school for me in terms of getting to know how big corporates work and definitely corporate America. And being able to learn, from my bosses at the time and from the CEO of Deloitte in Israel at a time, what it really means to be a leader? And how to do it in a day to day activities. And at a time I realized that I want to do that in under, again, a role of an investor, but I want to do it close to where I guess where the headquarters is or where everything is happening and starting, and to me, Silicon Valley is still the place of where things are starting and where the trends are being shaped. And to me, that wasn’t an easy choice to say, well, I want to do that but in Silicon Valley. And then when I started thinking about MBA, as I said before, I tried to figure out which schools could fit my culture and at the same time could fit my career goals. I evaluate three different schools that could be a fit for a job like that. Some of them are in the Valley, some of them are on the east coast, but I’d say overall, once I got into Haas, that was a very easy choice for me. That’s exactly what I want. That’s exactly where I want to be. And nothing can beat California weather by the end of the day.
[00:05:22] Chris Kim: Absolutely. It’s even in the middle of winter right now, for folks who are in the snow, apologies when we’re recording this, it’s bright and sunny right now in the Bay. So what was it like when you first got to campus? I think Berkeley has a lot of public images or maybe even misconceptions, like what was that experience like when you first got to campus and did any of your preconceived notions or thoughts before you started the program, did any of those change as you started going through the MBA process?
[00:05:47] Oshri Kaplan: I want to say, as an Israeli coming from abroad, maybe that will be relevant for some of our listeners, maybe not. So we’ll figure it out. I would say, as an Israeli coming to Berkeley, Berkeley is considered one of the more liberal schools out there. And to me, as an Israeli coming in and expecting to see a few things on campus that might conflict with some of the images that I’m representing but, in a way as a preparation for that you have some sort of an image of what you’re going to be facing. But if I need to be honest, I haven’t seen any of that.
Just when I came to school, I said, be prepared because some of that will face you and you need to know the facts, then you have to know the answers and have to like, get being challenged and answer some of those challenges. I want to say that through my time at Haas and never really had a chance to get into any sort of conflict or any sort of challenges that were anticipated before Haas.
And when it comes to being a business school, the business school at Haas is one of the more diverse ones that I can think of. To me the reason that I want to get to an MBA in general, and to Haas more specifically was really diversify the exposure that I have to different industries, different, professionals. And to learn about all of those new opportunities out there and to learn about some of the histories of some of my colleagues.
I was coming to Haas very focused on what I wanted to do after Haas, but at the same time, I went to experience and definitely talk to others and see what was their experience. Because again, that was my first time in the US as a full-time student at the time and my first time as an immigrant. So I was coming with ears wide open and I would say that was very refreshing. And by the end of the day, as part of that old networking and exposures that I had for Haas, I actually found my next job after Haas so it was definitely benefiting, for sure.
[00:07:39] Chris Kim: That’s awesome to hear. One of the things that I think exactly to your point Oshri, is a lot of people have the preconceived notions that either Haas or Berkeley is super, super liberal and definitely there’s a more open, atmosphere. But I think on the flip side, I think exactly to your point, it’s almost super welcoming in that way as well. People have such diverse backgrounds, there are less preconceived notions maybe of what’s the right way or appropriate way. Like having that open personality. I’ve definitely experienced that during my time at Haas.
I feel like it’s one of the benefits because you get out of your traditional ways of thinking things and you really start becoming creative and especially in this area in the Bay where innovation is super important, it helps get you in the mode of constantly looking for innovation. Any fond memories or classes that influence your direction? I know you’re super keen on going to VC right from the get, what was that like?
[00:08:31] Oshri Kaplan: I think that probably the most influential course that I did, I took at Haas was Negotiations with Holly Schroth. To be honest, I’m negotiating now every day. My job is essentially to negotiate. So with that, I don’t think of any other course that I would rather take at Haas than the Negotiation. I guess, to me that was eye-opening because, as an Israeli, they are teaching you some sort of like a tactic around negotiation, which I found as very different than the tactics that are being taught in US-based schools and definitely at Haas. And to me, that was super refreshing. And it was hard. It was hard at the beginning and it was challenging at the beginning to find myself in situations where I need to adapt. I need to figure out a different way to approach things if I want to be successful. And that’s one of the classes that I’ve kept using since then. And keep using the materials from time to time, I have to say, and I think I actually mentioned it to Holly as well. This is the most influential course that I had in Haas.
[00:09:31] Chris Kim: That’s awesome. What about the course do you think was most helpful in your experience? Cause you definitely had professional experience, you’d worked at big companies and you’d already been in VC, how did that augment what you’d already experienced in your past professional experience?
[00:09:44] Oshri Kaplan: Again, to come and go back to what I said before about the difference. I think the main difference between called the Israeli approach versus the American or the Haas approach for negotiations is this pie, right? You have been taught in Israel that you have this notion that if you’re winning the negotiations, the other side needs to lose. And if the other side is losing, you must be winning. And that’s essentially the notion that I was coming up with at the start and try to figure out how can I leverage some of those tactics in my negotiations. And there are some areas and instances where that’s not true. And I found more of those instances as part of this course. And I happened to find a lot of those instances after the course. And in the course itself, part of the basics and the strategy around and tactics around those is to really figure out how can you expand the pie to both sides versus take the pie from one and give it to another. And I think maybe it sounds basic. And I would claim that it is basic, but in order to find it, and in order to, in a way, figure out how to do it at tactics of how to do it, that’s to me the secret sauce. We felt stealing any off all the funder and let the people out there essentially go. And if they have it in their undergrad or grad school, definitely do it in their executive sessions that Holly is definitely teaching.
[00:11:12] Chris Kim: Oh, awesome. You kind of mentioned the experience at Haas helped you to transition or find your next role post-grad in venture capital. What was that experience like? Because today, everybody wants to be in VC, but Oshri you’re one of the success stories. How did you navigate that? Especially for VC, if I understand correctly, it’s not really a traditional pipeline or a traditional recruiting process.
[00:11:32] Oshri Kaplan: There’s no like career day where a VC is coming to Haas and present and everybody’s just putting their resume. I’m not sure if that’s actually happening today. It used to happen before in some of the other industries. When I was at Haas. But for VC, you need to basically shape the opportunity for yourself and get to know people and learn and see how can you provide any sort of value to those funds and being able to show some of your own value to them. So I would say as part of those networking activities, as part of Haas, I got somehow connected to one of the senior leaders in a Fortune 500 company named Flex. And Flex is a design engineering and contract manufacturing company. So it’s playing in the hardware business. And I didn’t know a lot back then about that, to be honest with you, but some of the challenges that a company was facing were very similar to solve the challenges that the company before I went to Haas, in Deloitte, we’re experiencing. And basically, the senior leader after a couple of meetings says, “How about you join us and try to do or do even more of what you’ve done at Deloitte and do it here in Silicon Valley, in the headquarters where the company is?” I say, well, that sounds good. Let me check. I know a lot about your business or industry.
I ended up joining the company with the mission of establishing its venture activities. And that was a great time to be an investor in hardware. That was around the most recent hardware booming years, 2014, all the wearables AR, VR, robotics, IOT sensors, again, booming years and fun time to be around hardware. And I had a great time there and we’ve done dozens of investments and that was super fun.
[00:13:13] Chris Kim: That’s awesome. I noticed one of the things, you essentially became a board observer really soon after business school. What was that experience like? I think most folks maybe have no idea what happens in those types of situations, but you got to kind of trial by fire as you guys scaled really quickly from what I understand.
[00:13:30] Oshri Kaplan: So board observer is a role that you are assuming, on behalf of your fund or a corporate fund. But it’s something that you do on that behalf and you’re basically acting as a board observer in board meetings. There is a difference between that and a board of director because a board director is the one who basically helped run the company on a day-to-day basis and help make decisions together with the board of the company of which direction to go. The board observer has no voting rights, but it has from the name has the right to observe the activities and obviously participate in discussions. And be able to help the company as much as needed. Some of the corporate venture arms and venture arms are asking for board observers as part of their investments. I was lucky enough that we, as funds, asked to have a board observer in some of those investments. I didn’t have them in all of my investments. In my current fund that’s part of our requests to be a board observer, the minimum, because that’s how we believe we can actually have value to the company.
So, how is it to be a board observer and a board of director? I would say, that’s a great responsibility and accountability that you need to have for the role. You need to be able to listen. Specifically, as a board observer, you need to listen and realize what are some of the challenges the company is going through. And be able to really figure out your role at this point could be like an advisor in a way to the CEO of how to get beyond the specific issues. At the same time, owning the rights as an investor for the company. So I think this is where being part of the board is definitely a very interesting experience in general which someone that any investor will probably do at one time in his life.
[00:15:14] Chris Kim: That’s great to hear, Was there any kind of learning curve in that, or did you essentially just pick up and go as soon as you got there?
[00:15:22] Oshri Kaplan: When I started my career on the VC side back in Israel, I had an experience of being on boards. So I want to say that was not such a unique thing being here in the US and acting as a board member or a board observer. Obviously when you have a bit more responsibility and when you have multiple boards to manage, I would say that’s what creates a bit of a unique, I would say prioritization of your day-to-day activities and being able to still do your job as an investor, being able to continue and find great investment opportunities while at the same time help companies that you are investing in and being able to support their day-to-day operations. I think that’s the main challenge as an investor today. And some funds are really dividing between the two and essentially not allowing some of the investors to be an active board observer or even a director and essentially an operator. But some companies like ours, we are both on the operator’s side and on the investment side.
[00:16:22] Chris Kim: That’s awesome. Oshri, could you share a little bit, for folks who might be listening but aren’t familiar, you know, what does day-to-day looks like for a venture capitalist or a VC investor? And how do people split your time as you’re talking about here, between core aspects of investing and then all the other responsibilities that are associated with being in a VC fund?
[00:16:41] Oshri Kaplan: In general, I would say an investor probably needs to divide his time between looking and listening to new opportunities, depending on what exactly is your role, whether you are in associates, in one of those funds or principal and later director or general partner. You basically need to manage your time somewhere around the same time I think you need to go and definitely listen to new opportunities. I think that’s part of our role. I think every investor out there is probably looking between three to ten opportunities a day. And being able to network and connect with the entrepreneurs and being able to learn more about their activities. Nowadays, you’re doing it mostly around Zoom. To be honest with you, it’s still here on Zoom versus actually in person.
And the second element is definitely helping your portfolio companies. So you have been investing in some of those companies that require your help in being able to manage the specific issues that could be with hiring some new talent to the company or how to streamline some of their operations. And some of those requests that sometimes are happening at the board level and sometimes are happening just because of the day-to-day help that the entrepreneur and the management team want to discuss things with you on some of what are your thoughts, how to strategize around some of those questions that were raised.
So that’s mostly it. I think that definitely takes most of the time. Now, for a corporate VC like ours, we obviously need to think about things that are strategic for our corporate. So that requires some work that requires an alignment and thinking about what are things that could be strategic for our corporate. And that’s obviously adding some additional level, an additional layer for the work.
[00:18:23] Chris Kim: You had an awesome experience at Flex. How did you decide what to do next? And what was that process like for you?
[00:18:29] Oshri Kaplan: I had a great time at Flex. And that was a fun time to be in hardware back in the days but thought that I got to the ceiling of our ability to grow our fund within Flex. And also, it was five and a half years, I needed a refresh on my own career path. So I was up. And I was consulting for a few different startups out there and a few brands, new VCs, and CVCs as a venture partner. But one thing was I was missing and that’s the actual execution of VC, right? Being an operator and helping to solve those startups and that’s around that time the relationship with Munich Re started. And after a few months of a relationship, I was joining. And I joined Munich Re back in June of 2018. And since then and there, so almost three and a half years.
[00:19:15] Chris Kim: Could you maybe just explain at a high level what’s the area of focus or kind of what are the areas that you’re interested in generally speaking for Munich Re Ventures?
[00:19:23] Oshri Kaplan: Yeah. So Munich Re Ventures is the VC arm of Munich Re, which is a very, very large German multi-national insurance company based in Munich. And one of the world’s leading providers of reinsurance, primary insurance, and in general risk transfer services. And we are ending today about the billion-dollar investor assets. And I would say our main interest is investing in startups that are really looking to transform the future of risk and of risk transfer.
I would say risk transfer is one of those areas where people are not really associating it as one of those as a theme. We at Munich Re, are definitely looking at this as the future. And we think insurance is the industry that is basically setting the infrastructure for a lot of other different industries to be in existence today. So being able to sit at the core and invest in some of those technologies and business models that handle that core risk in different ways, to me, is fascinating.
And the reality that we see today, insurance touches so many different angles and the world of insurance is changing just we know our lacks about like, where are we actually consuming insurance? And when we are buying insurance, and whether you are a personal or commercial entity, you will look to that. And the reality is that the insurance that we consume a few years back or ten years back, it’s definitely not the one that we’re consuming today.
People less care today about who is providing the insurance. They care about the fact that they have insurance in the right time. So to us, that’s a big trend and that means that we’ll see more and more access to them and embedded insurance, just like we see on the embedded finance as part of basically everything. We’re definitely following those trends and looking to invest in some of those core platforms that either enable that or are part of that ecosystem.
[00:21:18] Chris Kim: Awesome. It’s really interesting. You’ve had both pre-pandemic and now like in the pandemic slash, hopefully, knock on wood, post-pandemic sometime soon. How has that been from a VC perspective and the industry at large, what’s your take on that? Having seen the whole experience?
[00:21:33] Oshri Kaplan: I think in general, not just in Munich Re but I think in general, the world became even smaller due to this pandemic. I think if before you needed to go and travel to specific areas around the world and look for investment opportunities, nowadays, the investment opportunities just find you over Zoom in your convenience time and you don’t need to go and travel to find those opportunities.
At the same time, I think it’s also creating some competition for investors because there is no shortage of funding out there. And a lot of investors have the same resources as you. So you really need to differentiate and find how you can position yourself as a smarter investor, as the one who can actually provide better value to your portfolio companies and to your upcoming prospects as portfolio companies. So I think that creates some competition among us, the VCs.
I think those are the main points, you know, I think we will get back to some hybrid mode where we’re spending some of our time in front of computers and some of our time back to in-person meetings hopefully and which will maybe streamline our work beats more even. I feel like we’ll figure out some sort of balanced solution to that. I feel like the in-person effects of meeting entrepreneurs and meeting even other investors and learning from them about what’s interesting for them, I think that’s not going to change. I think you definitely much easier for you to create a relationship in an in-person versus over Zoom or Slack. And I think that’s part of what we do as part of the networking relationship building. And I encourage everyone to go and continue to do that and not stick behind the computer screen.
[00:23:14] Chris Kim: That’s great. For current students, Oshri, you’re several years out now. So you maybe have perspective. What kind of advice would you give to current students or perspectives who are thinking about coming to Haas? Thinking about going to VC and would ask you for advice, hey, what can I do to be as successful as you are?
[00:23:30] Oshri Kaplan: I think people need to be vulnerable. And when I say vulnerable, I mean that they need to open themselves to the ideas of something that really being open-minded about what they are going to see and learn and be open-minded about networking, be open-minded about people that they’re going to meet during those couple of years of three or four years at school as those are the years that you don’t really know who you’re going to meet. And the reality you don’t really know where’s the next opportunity will come and how you’re going to meet your next employer or a reference to a new employer.
And I think to me, I always had in a way, a plan in my mind and I need to follow this plan. But the more I thought about the reality is that nothing really went according to the plan. But it was in a way parallel to the plan. As long as I had a plan but I was open enough to really expose myself to other options. Those other options eventually were created. I find myself coming in and really absorbing some of them. And I think by that, new opportunities were created.
So I would say if you’re looking to get into VC, you basically need to create your own path. And like I said before, you get a bit more connected about what’s happening in the world right now. And what’s happening in the VC world specifically, and being able to find some elements of where you can actually add value to some of those VCs. And search for them and talk to them and be out there and continue to network and do it in a way that doesn’t position you as a desperate person, but more as like, I wanna learn from you. I want to help you as much as I can if this help is needed.
[00:25:05] Chris Kim: Oshri, it’s been great having a conversation today. We end typically with a rapid-fire, where we ask three or four quick questions. So if you’re up for it, we’ll throw some unexpected, not prompted, rapid-fire questions for you. All right. So first one, the favorite place that you liked to eat when you were at Berkeley?
[00:25:24] Oshri Kaplan: The Pizza Boards.
[00:25:25] Chris Kim: Oh really?
[00:25:27] Oshri Kaplan: Cheeseboard pizza.
[00:25:28] Chris Kim: Cheeseboard. Oh, very popular one.
[00:25:30] Oshri Kaplan: Is it still there?
[00:25:31] Chris Kim: Oh yeah. Yeah. I think so. Yeah. It’s definitely, I think the weekend’s usually good. If I’m remembering correctly. Yeah. It’s definitely one of my favorite places. What about this, experience as an MBA student or your experience graduating from the MBA program?
[00:25:46] Oshri Kaplan: I would say experience as an MBA student. I feel like, I wouldn’t replace my time in Haas with anything else. I think that while I was very career-focused when I’m coming into the US and I knew what I wanted to do after Haas, I really enjoyed the company and I enjoyed the people at Haas. And I thought that was one of the things that make these times such a great time for me. Specifically, as a foreigner coming into the US for the first time and seeing all of that, really it’s such a diversified experience, I guess from all the other international and local students. That was just amazing. So definitely, my time at Haas.
[00:26:20] Chris Kim: Awesome. And the last question, what’s a great piece of advice that you’ve received either personal or professional?
[00:26:26] Oshri Kaplan: Be open-minded. I mentioned this before, but people need to be open-minded about what can happen. And everyone has a plan or at least people with coming into the MBA, most of them have a plan of where they want to be. I mean, they ask us to have a plan when we’re coming into MBA. So most people have a plan of what they want to do after an MBA. I feel like, while, yes, maybe you can do that but be open-mind about what can be during your time here. And definitely learn from other people’s experienced memories and others.
[00:26:57] Chris Kim: Oshri, it’s great to be in conversation today. And thanks again for joining us on the show.
[00:27:02] Oshri Kaplan: Thank you. And go Bears!
[00:27:04] Chris: Go Bears!