Conversations with members of the Harvard and Radcliffe Class of 1992.
Hosted by Will Bachman.

Episode: 91

Andreas Stavropoulos, Entering the Third Act

Share this episode:

Show notes

Andreas Stavropoulos, a venture capitalist and entrepreneur, came to the United States from Greece at 18 and has been in the United States ever since. His big moves include marrying his high school sweetheart, arranging their lives around graduate school, medical school, business school, and moving to California. He is now 55-years-old and is excited about the third act of his life, where he can choose where to spend his time more than he used to. Andreas started his career as a venture capitalist in 1999 and has been doing so for over two and a half years. He has stopped making new investments in this endeavor and is now spending most of his time back to nonprofit public service and helping his country. He is increasingly spending more time back in Greece. In the third act, Andreas is considering the empty nest and choosing where to spend his time. He is now in the third act phase, where he is stepping back from full-time work, focusing on what he chooses to do with his 20+ 25+ productive years. This involves stepping back from full-time work, reducing board load, and not chasing after new deals.


A View of the Business Landscape in Greece

Andreas talks about his decision to pursue public service in his third act. He gives a brief overview of the crisis Greece has experienced since the 1980s. The crisis was ushered in after a short, populist five-year phase of trying empty promises. However, in 2019, a new generation of moderate, business-friendly leaders emerged, inoculating voters against the empty promises of populism. Greece is now a leader in this regard, showing the rest of Europe how a post-populist society and governance model can look like. The generation of leaders in power is younger and more business friendly, making them an opportunity to help the country catch up with Western Europe. He is also working on a board of a private company that manages large privatization and public-private partnerships in Greece, such as airports, ports, and highways. Another area of focus is AI. He is on an advisory committee to the prime minister on topics related to artificial intelligence, and he talks about the influence of Greek diaspora.


On the Board of a Privatization Entity

Andreas discusses his experience on the board of an entity that manages privatization. The board includes seven independent members. The nominating committee has combined complementary skills, providing a sound foundation of skills in various areas. The finance side of the board includes working with portfolio companies to mature them for financing, going public, or getting sold. The board also oversees state assets that are not ready for deal-making, designing business plans and leveraging them to create something attractive to private investment while maintaining upside for the state. The board also involves working with bankers and consultants to do transactions, as well as fiduciary duties. They also work with assets to maximize value and develop eco-friendly tourism activities. The advantage of being on the board is learning about the country’s large construction projects and local opportunities efficiently. Additionally, working with local players, such as large investors and consultants, allows the board to build a network that allows them to understand data and the players in a relatively small economy.


Managing and Motivating People

Andreas shares his insights on the business world and the way things work. He explains that talented people, particularly project managers, can be difficult to unleash due to non-meritocratic and bureaucratic processes. For example, Greece’s promotion system was purely seniority-based, based on degrees and years of service. However, this approach has led to a loss of motivation for people to go above and beyond. Andreas has learned the importance of thinking about reward systems and what drives human motivation. He believes that humans are rational and evaluative maximizers, constantly processing inputs and making decisions. 


Third Act Pursuits and Dharma as a Guiding Principle

Andreas discusses his personal portfolio, including his involvement in public service, sailing, and travel. The couple plans to focus on their children and professional responsibilities, with Andreas’ wife aiming to maintain her FTE at Stanford. He and his wife have also been involved with education, serving as chair of the board and treasurer at their children’s school. He is currently president of the Alumni Board for Harvard Business School and has recently joined the board of a nonprofit that provides policy recommendations for the diaspora of Greece.  Andreas believes that leaving professional firms is intentional and requires planning and commitment. He has had to tell his partners about entering a new phase, which involves changing their brand and deciding who will be in and who will not. Andreas discusses the concept of Dharma, which translates to  roughly “destiny, duty, purpose.” Meditation, a spiritual element that began about 567 years ago, helped him understand their essence and purpose in life. The COVID-19 pandemic forced him to reevaluate and rethink his beliefs. He suggests that the Dharma concept is not prescriptive, but rather a gradual, intentional approach to life. He suggests that by focusing on the essence of their goals and leaving a mark on the world, they can evolve in the right way. 


Lessons Learned in Hiring Talent 

Andreas shares his lessons in hiring people who are not just like him, but also have different backgrounds, approaches, and styles. He emphasizes that having diverse people around you can lead to better outcomes overall. The biggest lesson learned is to stop thinking about hiring people based on their appearance or experience. Instead, focus on having people with different backgrounds, approaches, and styles that work well together. It’s not about being friends or building a nice place to work, but about creating fair and purposeful environments. Another important lesson learned is the importance of communication and truthfulness in venture capital. Building a reputation goes beyond single interactions, and it’s never about a single moment. Instead, it’s about building value over multiple years, and in many cases, those same founders or employees will go on to other companies. Instead of being transactional, it’s crucial to be upfront about what you stand for and what you can help with. Being upfront and admitting that you don’t know is difficult, but it’s essential for long-term success.


Influential Courses and Professors at Harvard

Andreas discusses his courses and professors at Harvard that continue to resonate with him, whether it’s professional or side interest. He highlights Justice with Michael J. Sandel as the most relevant course, and his computer science classes on algorithms have taught him the ability to think systematically and break down problems in a way that works for him. He plans to spend a chunk of his third act living in Greece, despite being away for nearly 35 years, and he believes that the culture, business outlook, and family connections are all factors that lead to better quality of life. 



02:56 Life phases and prioritizing personal choices in the third act

07:22 Greece’s economic crisis and potential for growth

14:06 Board experience and diaspora contributions

19:07 Government work, talent, and motivation

25:10 Human behavior and personal interests

27:58 Personal growth and planning for a successful third act

33:44 Intentional exit from professional firm after 10+ years

39:31 Selecting and working with talented individuals in the venture capital industry

45:28 Retirement, quality of life, and family ties in Greece




Get summaries of each episode, hand-delivered straight to you inbox



  1. Andreas Stavropoulos


Will Bachman, Andreas Stavropoulos


Will Bachman  00:03

Hello, and welcome to the 90 T Report. I’m your host will Bachman and I’m here today with Andreas stavropoulos. Andreas, welcome to the show.


Andreas Stavropoulos  00:12

Thank you. Well, it’s great to be here.


Will Bachman  00:14

Andreas, tell me about your journey since graduating from Harvard.


Andreas Stavropoulos  00:18

Sure. So I should mention I came to Harvard from Greece. So as an 18 year old with a couple of suitcases. So the journey for me really started after high school. And then I’ve been in the United States ever since. So, for me, Harvard was the first step towards then work, more schooling, change at work, and other change at work. And my big moves, I would say, in terms of the journey, were first of all mapping my high school sweethearts who followed me to Harvard from Greece Just a year later. So we’ve been together since the undergrad days and are still together, we have three kids that are now themselves going to college, our youngest has actually been admitted to Harvard early, so she’s about to leave at the end of this year. I mean, you know, at the start the next academic year, but also in terms of big, big kind of milestones, we are married my high school sweetheart, and then arranging our lives around graduate school for her was medical school for me was business school, and then making the big move to California and 97, where we’ve been sin. So 25 plus years in California, raise three kids. And now I would say at 54, but we’ll be 55 this year. Now, the way I think about it is the next sort of third act is about to start the third act of my life, which we are happy to talk about, where I get to kind of choose where to spend my time more than I used to. And I’m frankly extremely excited about this third phase and you know, trying to get in sync also with my wife to make sure that we can be, you know, in the same geography at the same time, hopefully for more than a month or two at a time. So journey for me it professionally, I ended up being a venture capitalist, I started that turn of the century, right in 1999, and have been a venture capitalist ever since. And for the past two, three years or so I stopped making new investments in this kind of effort, started this third act, where basically, I get sort of most of my time back to do things like nonprofit public service, tried to help my country where I’m increasingly spending more time back in Greece now. Things of that sort. So I would say that’s a good summary.


Will Bachman  02:37

Wow. Okay. I want to hear I’m so excited about all this. But I’m particularly interested in hearing about the third act. So there’s so much to explore. Why don’t we start with the third act? I do want to hear more about your VC work, and last few decades. But why don’t we start there? Tell us about how you aren’t thinking about this third act in your life now and what sorts of opportunities you’re considering about how to spend your time to dive into that a bit? Yeah, yeah.


Andreas Stavropoulos  03:11

So this is not mine. Someone used this analogy with me, I don’t even know what the original source is. But someone described to me life in terms of the ABC model, right? Where the first the first part of your life, it’s the a phase, that’s like the active phase, where you typically maximize something, right? It’s usually one or two dimensions, you know, for me, for a lot of sort of type A, folks like myself and my wife, it tended to be career oriented, right? So you spent the first I don’t know, third or so of your life, on schooling, going to the best places you can, you know, for us, it meant leaving Greece and coming to the states, studying hard, working hard, trying to make money start kind of building a career, and you really not worry too much about anything other than the one or two things you’re trying to maximize. And then you know, you enter this B phase, which is let’s call it the balance phase, where you know, you’ve got other demands on your time that are equally important, where it’s not as clear anymore, that you just maximizing one or two things clearly, like you have, in our case, we had a family, that kids are now getting a little older, to the point where you can miss things if you’re not there, right? There’s only one of those live performances that’s happening. There’s only so many opportunities, you get to coach your kids playing, you know, softball or soccer or what have you. So you enter this phase where you have to make trade offs. And you know, to maintain that balance. And that’s frankly, for a lot of people, including for us, that are used to being you know, type a go for broke, go, go go it tends to actually be a hard transition. And for us, it was no different than happy to talk about that. So you’re in this B phase where you’re balancing you kind of end up finding what works for you. Frankly, a lot of people don’t that’s where you run into all kinds of different Trouble with family or this or that, in our case, knock on wood, we managed to settle out what worked for us. And then you kind of maintaining this balance. And and at some point, that is what I call the third act, which for me, hopefully, it’s right around this 55th Kinda year, you, you get into C phase, see for choosing, choosing where to spend your time, we’re kind of the feeling is, I don’t need to prove anything anymore. If you’re lucky to be economically mean financially self reliant, and you don’t have to worry too much about that either. So it’s really more about oh typically comes with the empty nest, we’re about to be in the empty nest right later this year. So if you kind of have to now think about where what am I doing? Who am I? What’s my purpose? What am I doing? What do I want to do with, you know, the 20 plus 25, plus, you know, productive years that I have left. And this is what I’m thinking of as the third act, which for me, has meant increasingly doing things that I choose to do. Basically, stepping back from full time work, I’d say, at this point, my work work, percentage of time is maybe 30% that I’m doing for my sort of day job, let’s say I haven’t been making new investments for the past two, three years. So my, my board load has dwindled over the years. And I’m not chasing after new deals. So that actually frees up a lot of time. And I’m filling that time, with activities that I choose to pursue, which for me, this at this juncture tends to be a lot of, as I said, public service and nonprofit, but also a frankly, personal projects, right, we’re building a house in Athens, our parents are getting older, we lost my mother in law late last year. So we’re getting to this kind of age in their late 70s, early 80s, where they need more time. So you have to be kind of more intentional about that. So basically, this third phase, I’m defining as choosing and being intentional about how I spend my time, and trying to always kind of think about, you know, what’s the best, let’s say portfolio of activities I could be doing, that keeps me happy. I’ll leave it at that.


Will Bachman  07:17

I want to dive into this more. Tell me about the public service aspect of your third act.


Andreas Stavropoulos  07:22

Sure. So Greece, Greece has undergone a period of huge crisis that, frankly, a lot of the seeds of that crisis were sown, you know, in the 80s, when when there was socialist government that took over that, you know, did a number of kind of good things from a social liberalism prospective, let’s say? And, frankly, modernize the old bunch of institutions. Those were the good things. But I’d say those paled in comparison to things like what do you call them, taken over a whole bunch of assets and whatever the opposite work from privatizing is, which I’m now blemish


Will Bachman  08:03



Andreas Stavropoulos  08:05

Thank you, thank you, thank you nationalizing a whole bunch of resources and a whole bunch of institutions, and effectively chasing private enterprise, and especially industrial type companies really out of the country. And Greece paid the price of that, that was really the decade of the 80s. And then the sort of sort of profligate 90s, after Greece was effectively bankrolled by the European Union, it really paid the price in the 2000s. And it culminated in the crisis post the financial crisis of 2009 2010. And then Greece went through a 10 year plus more like a well, 15 year period of really dark days, right 25% Plus GDP that went down, you know, from from peak to trough a whole bunch of people out of work, record unemployment, youth unemployment over 50%. Overall, in the 20s. I mean, the really, really bad times, and unlike some of the other countries in Europe, that went through similar acute phases of the crisis, like you know, Ireland or Spain or even Cyprus, and Greece did not really took much longer to reach the point where, let’s say society capitulated, in basically thinking that, you know, the old ways are not going to work anymore. So that’s the bad news. The good news is that this ushered in after a brief, populist five year phase of, you know, real populist, like really trying the empty promises and seeing that they don’t work. The good news with all that is come 2019 You had a actually starting in 2016, or show the old leaders and the old way of doing things got brushed, brushed aside, and you have a new generation of Lee leaders that are much more middle of the road moderate, business friendly, kind of realistic, in some ways, inoculated a whole generation of voters against the empty promises of populism. And it’s funny to see that in Greece that we typically used to think of as a laggard, in this one sense. Greece is actually a leader now, right, it’s actually showing the rest of Europe. And frankly, we could use some of these lessons here in the US about what a post populist, you know, society and governance model can look like. So make a long story short, to me, that is a well, for two reasons. One, it’s our generation that come into power, it’s kind of our age people effectively running things now. And it’s a small country, so you tend to know who they are. Actually, a lot of them are Harvard connected. So there’s the additional thing I know a number of people, including the prime minister from his Harvard days, but the so you know, so if you’re going to help ever, when are you going to do it, you might as well do it when he kind of is your turn, and you know, the people. But the second and most important thing is because I truly think that there’s an opportunity to kind of start a almost like a mini golden age for the region. And and that’s a great opportunity, where I feel not just myself, but we’re not I know a lot of people in the diaspora and the Greek diaspora feel that this is our time to come and help. So in my case, what’s that meant is, again, consistent with this kind of choosing, I’m not doing anything full time. But I have joined a couple of different things. I’m on a board of the entity that manages the large, all the privatization, and large public private partnerships in Greece, things that have to do with things like airports and ports and highways, concessions and things like that. We’re basically private investors are involved in an effort to re modernize, and open up and deregulate access, to frankly, catch up with the rest of Western Europe that’s already done that Greece has lagged. So there’s an entity that’s trying to run that that’s not, let’s say, constrained by the sort of tighter restrictions of working within the public sector. So it’s actually a private company that does it. Even though that private company is owned by the state, it still is governed as a private company, which means it’s much more flexible and nimble and able to do these things fast. So I’m on the board of that entity, which which has been a terrific opportunity for me for the past couple of years. And then most recently, I joined this committee to it’s an advisory committee, to the prime minister on on topics that have to do with artificial intelligence, specifically, how should the country take advantage of AI, both in terms of things he could do internally better to improve productivity and what have you in the public sector and the private, but also how to potentially become a beacon or a place where others want to come because of a number of advantages that could be built around it, such as computing power of certain kinds, such as talent that exists both locally and diaspora that’s interesting to come back, including a lot of academics, private universities that are finally getting opened up in Greek. So anyway, using using basically compiling advice that can be used to make Greece and more attractive destination and a more attractive user of artificial intelligence writ large. So those are the two I’m doing right now. And I’d say more than that, I’m on a bunch of nonprofits. I’m on the board of endeavor, Greece, which is an organization that helps entrepreneurship and innovation, NLP in a lot of the funds, so I tend to do a lot of kind of mentoring and meeting with a with a with a local ecosystem of founders. And just right that tried to help whatever I feel like I said, consistent with choosing face where I feel like my time is well spent. That’s what I’m doing there.


Will Bachman  14:08

Talk to me about the experience on the board of this privatization. Yeah. What one angle I’m interested in is what’s been the reaction to the people with someone who has been living in the US for the last 30 years? Yeah. Is that a positive or negative? And just like, What have you learned about the country with this view that you have on the board of this, this entity? Sure.


Andreas Stavropoulos  14:37

So on the first question, you know, Greece, like Israel, like some other places around the world has a very active diaspora and arguably bigger that argument it is mathematically bigger that as per LAN, local population when I say diaspora, I don’t mean just people have genetic you know, Greek roots or what have you, but that You know, discovered it in 23. And me, I mean, people that identify as Greeks that maintain some are many aspects of the culture, you know, language, traditions, religion, you name it food, you know, anything. So, sort of an identity, at least partial partial identity that identifies the country. So as a percentage as a ratio of a diaspora to local, it is huge. And, frankly, typically, because Greece has always been a small and relatively poor country, typically people who leave leave to do better. So from an economic and a, also, frankly, academic and a whole bunch of other dimensions, these sort of achievements of the diaspora as a whole, both because the numbers are larger, but also because they leave it’s a self selected group that tends to leave that does well, more often than not, you have a lot of resources in this diaspora. So the the recent phenomenon of people wanting to come back for at least part of their time to help is not unique, right, if you’re seeing that across the board, you’re seeing it in government, you’re seeing it in the private sector, you’re seeing it with reverse migration. So in that sense, it’s not unique on the board that we’re on for that entity, there’s seven of us, there’s five of us that are independent, the other two are part of management. So if the five independent, I want to say All five have done a significant part of their careers abroad, and of the five, two of us, I’d say, are even more comfortable in English than in Greek, right? So one, one is someone who’s a Greek that grew up in South Africa. In my case, I’ve obviously spent most of my time in the US. So there’s no skepticism in terms of is this like weird or different? Because it happens a lot, number one, number two, it’s a board where the nominating committee actually did a good job of trying to combine complementary skills. So in that sense, we are a very comfortable group, because for example, we have someone who’s a lawyer, and who is a very strong corporate governance type lawyer that sort of protects us. And we defer to her. When it comes to questions of, you know, process, and paperwork and sort of backup and liability and things like that. You’ve got someone who was actually the Chair of the Board, who is an engineer and engineering professor, logistics expert, transportation experts, someone who’s got to work both as an academic and a practitioner in the field. He’s very much of an engineers engineer, right? He asked questions that have to do with a practical issues with the, you know, how’s this exactly? Going to work asking questions about the details, you got someone who’s an auditor, the chair of the audit committees, and auditor and control CFO type person, and sort of what I bring to the table is I bring the finance side, being a venture investor for so many years, but also kind of thinking about not just the the deal itself, but how you work with portfolio companies to, let’s say, mature them to a point that they’re able to attract further financing, or go public or get sold or what have you. That’s very similar to the type of work that entity does. We don’t just run, we don’t just run transactions, we’re not like a bank, right? In many cases, we have a lot of assets that we that we sort of oversee, that are state assets that are not at the point where they’re ready to do a deal around them. So you have to actually like design almost like a business plan, or you have to think about how would I best go about leveraging this asset to create something that couldn’t be attractive to private investment that still maintains upside for the state? So you see what I’m saying. So it’s a combination of, of the finance and the deal making aspect and things like for example, we just took, we just took the Athens airport International, the company, we took it public in Greece, right? So there’s more kind of typical, working with bankers and consultants to do sort of transactions. And I’d say that’s a big part of it. And you have to do, you know, fiduciary duties and all that over that. But I’d say there’s an equally if not more important part, which is around working with these assets, taking inventory and figuring out what it is that you should be doing with some of these assets to maximize the value, not just to a one off transaction to the state, but frankly, through the economy overall. Applying multiplier, like for example, some some region that should be great for developing an eco friendly, let’s say tourism activity that’s laying fallow, thinking about what is the right kind of business plan to potentially use and what’s the kind of licensing that they would need to be able to attract the kind of investors you want. So what I’m getting out of it is, first of all, I’m learning a ton about a country that I’ve really been gone for most of my life from right with the as you can imagine, this is all the large construction projects a lot of the large, you know, assets of the state and where they are, and learning about opportunities that exist locally in a very efficient way. So I’d say that that is a huge advantage I’m getting out of that. And the second one is that by definition, because you ended up working with a lot of the local players, both in terms of the large investors, but also the who are the local consultants and bankers and others, just on a personal basis, I feel like I’ve built a network in a very efficient way, that allows me to have a very good understanding of data, who are all the players in a relatively small economy? And that’s just great education for me.


Will Bachman  20:45

Wow, what an amazing experience. I’m curious, having spent your previous professional career as a VC working with for profit companies? What have you learned about the world and the way things work? What different perspective do you have now, versus when you, you know, when you just got when you just joined this board, but the way government works about how grease works? Yeah, tell us about some of those learnings?


Andreas Stavropoulos  21:16

Well, the other thing that I’ve learned also through that entity, but also through the work with AI and other things is that they’re actually excellent, talented people that are in all kinds of different roles, right, and not necessarily the ones who are the most prominent or get on the limelight. I’m talking about people who are actually the project managers who are running some of these complex projects. I mean, they’re just terrific, terrific talent, right. And the challenge in many organizations, especially the more sort of uptake they are in, the more they have politics involved. And all that is, is not that you don’t have talent in there is that sometimes unleashing the power of that talent can be difficult, because of non, let’s say, meritocratic, and very bureaucratic processes, requirements, or other things that could have been put together originally for good intentions. Like, I’ll give you an example. You know, for the longest time Greece had no true meritocratic way of giving promotions in the public sector, it was purely seniority based. So it had to do with where you entered where you entered had to do with how many degrees you had, and how many years of prior service yet somewhere else. And then from that point on, it was done effectively like clockwork based on seniority. And the rationale for that was it was put together because before that, it used to be very much of a nepotistic kind of system where people would just favor with, you know, because it was very opaque, right? So they would just favor their friends. So they said you want done with that, if we have anything that’s qualitative, it is open to being you know, captured by by people wanting to do favors favoritism and nepotism. So we’re gonna make it purely, you know, seniority based, which I understand the intention, but of course, the solution is not the right solution right now. Now you’re ending, you know, kind of losing a lot of motivation for people to go above and beyond, because, you know, it doesn’t really impact their their career paths. So I use that as an example for the distortions, you know, that that exists in anything that’s not purely profit driven, to be honest with you. And I shouldn’t say just profit, I should say something, which is, what were you very clear about what you’re trying to maximize? It doesn’t have to be profit, it can be something else. But if you’re not extremely clear about what it is that you’re trying to maximize, and why it is that everything you’re doing is aligned with that goal. If you don’t have that, then you can get distortions. And the more vague it is, and the more closed it is, and the more bureaucracy and the red data that’s thrown in and politics and, you know, leadership changes that get driven by political ups and downs, the more you’re open to this system, not working because of these distortions becoming great. So what’s my point of all this, that I see that and one of the biggest lessons throughout my life and I, you know, I credit frankly, the business school, I mean, I went to HBS, a few years after undergrad as well. And you know, a lot of the thinking that you get as a general manager and a lot of the, the skills in the in the courses that you do, and all that have to do with human motivation. And they have to do with thinking about things like reward systems and what drives human motivation. And, you know, part of it’s also philosophical argument, and that’s an area where, you know, two people can disagree, but in my belief is that we are rational. Most most people are rational, and we’re evaluative maximizers is this model that Mike Jensen proposed in the 80s and 90s, you know that we’re rational, we’re always evaluating, and we’re trying to maximize something, it doesn’t mean we don’t maximize the same things. But whatever it is that we care about, we continuously process the inputs that we have around us. And we make decisions and we change our behavior. If you believe that as a fundamental basis for human behavior, you can actually draw a whole bunch of conclusions about what kinds of systems can be better designed to align this kind of behavior with a desired outcome. And what I can tell you is a big systems that don’t run and clear goals where you don’t get, you know, meritocratic ly or otherwise evaluated, believe me, you’ll never end up with systems like that.


Will Bachman  25:47

So I’m, I’m curious to hear about the other aspects of your portfolio as well. So you’re doing public service. Talk to us about some of the personal projects, you mentioned, you’re building a house, you’re taking care of your parents? Are you you know, is there also some travel or, you know, cultural interests? Or can you tell us about the personal portfolio? Absolutely,


Andreas Stavropoulos  26:10

absolutely. Because we got a little deep on his business stuff. So the look, I love to say it right, being Greek and with so many islands, and all the bodies of water, and all that Greeks have been sailors forever. So as a family, we got into sailing, frankly, during the pandemic. Before that, we didn’t have much time or much, you know, energy and frankly, foresight to plan because a lot of these trips you require to plan like a year out or something, to get a chance to get what you really want. So we weren’t ever that organized, too many things were changing all the time, you know, three teenagers running around. So it was it was not really easy. But in the pandemic, what changed was a, you couldn’t get to these countries to begin with, unless you were a local, so a lot of those charters got cancelled. And, and in B, we could work for anywhere. So, you know, we took advantage in 2020, the summer of 2020, right after Greece opened its gates, to Greek traveller from abroad in July, whatever it was, and we we Charter, the catamaran as a family. And it was by far the best family vacation we ever we ever have done. Before that we had only done like day sales, we had never kind of spent more than, you know, like one night on a boat somewhere, right. So this one was a first proper sailing trip, you know, six nights, going around to multiple destinations, all the meals on most of the meals on board, and I loved it. And so since then, we actually my wife and I have, you know, started a company in Greece charter company bought a vessel, we bought a catamaran, and we are using it so that we can go sailing, but also because we charter it, it kind of pays for itself. So it’s become now a three or four weeks a year thing. Couple of those with a family, couple of those with friends, we’re gonna go in a couple of weeks and take it out for the beginning of the new season just now in April, just for four or five days with some some relatives and friends. So this has become kind of a big thing. And it’s allowing us to now explore parts of Greece, that are really very difficult to explore unless you do it by sea. So So that’s been a great sort of project for the past couple of years that we’re really looking forward to where it’s gonna take us that one. I mentioned the house in Athens, you know, we’ve never, you know, because we move down to the country so early, so young, you know, we have our parents have homes, but you know, they have homes for retired folks who are older and kind of apartments and what have you, it’s not exactly you know, the type of home that you think of if you you’re thinking of your kids and eventually grandkids coming to visit. So there’s a lot of new developments that are happening around Athens, there’s one specifically that’s happening where the old airport used to be prime real estate that was sitting there for 20 years since the airport closed, they couldn’t get it out of the red tape involved to develop it, it finally got going. And part of that development will have some single family homes. And we were sort of lucky and had the foresight, I would say but also lucky enough to be at the right time or the right place to be able to get one of those lots. And so we are we’re building a what hopefully will be our sort of main base family home a few years from now, out of which I’m hoping we end up spending about six months a year in Greece. And you know, between the sailing and the summers in what have you and then the rest of the time basically whatever our kids end up, and whatever our professional other responsibilities might take us. I don’t see my wife quitting Stanford anytime soon, she’s an academic physician at Stanford, and she wants to maintain that I think she would probably lower her time, beyond the 55%, or whatever FTE that she’s at right now, which was down from 75% a year ago. So if we continue that trend, she might get down to like a third or less, in which case, you can actually concentrate some of the work and not have to be there, you know, every week, 52 weeks of the year, close, but something where you could be doing a couple of months, every quarter, most.


Will Bachman  30:34

So we have sailing. Amazing, that sounds like an incredible way to, you know, just connect with your family and your friends. Talked about your house, any other big elements of your personal portfolio?


Andreas Stavropoulos  30:48

Ah, well, I mean, the look, as a VC, one of the things you do as a VCs, you’re on boards, you’re in a lot of boards of directors, right. And those have been for profit companies so far. But we’ve also both my wife and I, at different times have been involved with education quite a bit. So I was the chair of the board, and before that the treasurer and in our kids school, K through eight, several years later, now she’s on it as an alum parent, I’m actually the current president of the Alumni Board for Harvard Business School. So it’s actually taking some time because we have two meetings a year in Boston that are multi day meetings, and then a bunch of interim working groups or what have you. So I’ve enjoyed that time. I’ve recently joined the board of like a policy institute. So it’s a nonprofit, that does sort of policy recommendations for the diaspora of Greece centered out of the US. So what it has to do with let’s call it education, or policy papers, or curricular thinking, or things like that, it is something that’s very near and dear to our hearts. And I see us continuing that kind of work. I also recently joined the it’s kind of like the Board of Overseers of my alma mater in Greece, which is this K through 12, kind of very venerated institution in Athens called Athens college, that that is also been an interesting introduction to the governance of schools like that over there. So I do think that, you know, involvement with education, in one way shape or another, is going to continue for me, and I think, for my wife as well, being an academic, so there’s that. And then there’s always the I mean, look, I do martial arts, I’m a big scuba diver, those are the kinds of things that I would love to have more time to be able to do in more places around the world.


Will Bachman  32:51

This topic of the third act, third is so on my mind, I just interviewed Henry Oliver, who wrote second act, which is coming out later this year. And, you know, a lot of our classmates are probably looking ahead to a third act like yourself, you’re doing it maybe earlier than some of us can manage to do it. But I think a lot of people are, what are some of the things that you did? Andre is to position yourself? Well, I mean, beyond just sort of financially getting in a place where you can choose what to do? What are some things that you did in terms of maintaining relationships, or, you know, just sort of getting the skills or planning ahead like you did with us? Talk to me about the planning that you did, when that started? And what were some of the things that you did along the way to position yourself to do the third act now?


Andreas Stavropoulos  33:44

Yeah, it’s, it’s a really good question. It’s kind of hard to after the fact go back, because you know, after the fact, we always want to find, you know, meaning and explain cause and effect. But the reality is, it’s much messier, you know, when you’re going through it, so I would say, I knew maybe five years ago or so, maybe five, six years ago was kind of I knew that. And I had, frankly, other role models here in Silicon Valley, other folks who have been successful founders of companies, and what have you, that follow the similar path that I also saw as folks who were trying to help a lot of other people define themselves not just through their one job or profession, but more in terms of, you know, how many ways they can help others. And I always found myself drawn to that kind of model. Right, so, so 6567 years ago, for me, I think that what it took at the time, was being realistic and being kind of true to myself about how much energy I had, frankly, to do another, let’s call it another big chapter of rebirth at my firm, right? I mean, venture firms or small professional firms that are you know, at the end of the day, frankly, owned by the partners. And so it’s not the kind of thing where you leave, where you can leave fast, in a good way. What I mean by that is you can leave fast, you can just up and quit. But that’s usually a bad thing, right? You’re either letting people down or there was a disagreement, or you got like, fire, like, usually the start is behind people who leave firms like that fast, someone’s unhappy, if not everyone is unhappy. The only good way that I know to leave professional firms like that is to be very intentional about it, and it takes some planning, right, you have to stop basically stop rehabbing. Because you raise these funds, these funds have 10 years 10 year lives, if not longer, right. So to be going out there and raise the fund and basically make a commitment to people who give you funds to manage and say, I’ll be there for you. It’s like a 10 year plus commitment you’re making. So to kind of get out at some point, you have to stop adding new things. And then they’re still a 567 however long your tail, just to get out. So because of that nature of my business, this is the sort of thing where I kind of had to tell my partner’s back 567 years ago is when I kind of had to say, you know, guys, we’re gonna enter a new phase, which for us also meant eventually changing our brand and all that. But like, as we enter a new phase, you’re going to need to know who’s in and who’s not. Because at that point, you want to have at least 1015 more years, and I’m telling you, I can see that coming forwards, like that might be a good time for me to be taken a different kind of role more as a senior adviser type thing. And those conversations, having had them was a huge boon. Because otherwise I would be so you know, like, loaded, let’s say with a with a with a baggage of Oh, my God, who am I going to let down, but that those were having those conversations early, and having been a path between then and now which again, in my kind of business, and I would say all these professional service type businesses, not a typical, was key for me, because it allowed me freed myself from not being more generative in my thinking about what comes next. But he even as I’m saying it, it makes it sound too easy. Because the reality is, there was a period of time there. And I think, frankly, things like meditation, for me helped and sort of more or less a spiritual kind of element that kicked into my life about 567 years ago, that also helped because it sort of naturally leads to the question of, you know, who are you? What are you about? What is your essence? Like, what what were you put on this world to really do? And so I took some time to sort of end up in a place with this concept, you probably have heard of it well called, you know, Dharma, in the Hindu in the Sanskrit, the Sanskrit word, right, which is hard to translate, but it translates somewhere between sort of Destiny duty purpose, something like that. So finding what the Dharma is, for me, was not something that happened overnight. And in a weird way, I think COVID helped, because COVID was so discombobulating for all of us in so many different ways that it almost forced me to reevaluate and rethink everything. So I’m not sure how prescriptive this is for others right now. Oh, you know, just have another COVID And, you know, go and be a digital nomad for a couple of months figure that, you know, it’s not very prescriptive. It’s just the way that it worked. For me, what worked for me was planning ahead, a, a gradual latte and sort of friendly exit from the day to day while also struggling, but doing it in a in a more intentional way of kind of trying to really boil down the essence of what I wanted to leave a mark on the world as let’s say it sounds a little sounds a little hottie but I don’t mean it that way. I meant I mean, more as a you know, just like what I said, like the Dharma concept, like what’s the thing that when you do, you’re, you’re evolving the right way. Let’s say.


Will Bachman  39:14

It’s so easy when we’re on the treadmill or just with momentum to keep doing what we’ve been doing. And so your decision, your intentionality to talk ahead with your colleagues and start not making new investments. I mean, kudos to you on that. I another area that very interested in is talent. On my other show, I had Tyler Cowen on the show to talk about his book talent. I’m curious in your successful career as a VC. Talk to me about some things that you learned about selecting talent along the way that you know now that you didn’t know in 1997 Or when you got started?


Andreas Stavropoulos  39:59

Oh, yeah. I’d say the biggest lesson, which I learned in many ways, the hard way, was to stop thinking or using criteria in terms of hiring people in terms of how much they, they look like you talk, like you think like you come from satellite, you know, the, like, I was a former McKinsey consultant for a couple of years and, you know, very analytical and came up through grade schools and all that. And, you know, you’re naturally drawn to you within your network. And frankly, from a chemistry perspective, you know, it’s only natural at the end up kind of getting drawn to people who share some of these types of experiences or can kind of speak to, you know, short cuts in the language, stuff like that, Oh, my God, not the right thing to do the value of this, this wisdom of crowds and sort of diversity of thinking and diversity of backgrounds. I’m talking way before, you know, the AI orthodoxy, I’m talking like, surely just which companies go out of business versus not, and which people end up working well together, which people you can depend on, when the going gets tough, you quickly find out that it’s not the people like you, usually, that are the ones that you need to have around you. And that, in fact, by having people with very different backgrounds with very different approaches, in many cases, very different styles I worked with, you know, colleagues and founders and companies, that styles could not be more different from me or from one another. And I found that those work so much better, and that you don’t have to be buddies, or you don’t have to, like work with people who are going to be your best friends. And that, you know, you don’t have to build places that are quote, nice, unquote, places to work. But you want to have places that are fair and purposeful. And it’s not about just buddy, buddy, you know, feeling good all the time kind of things. And so that was that was a lesson that I learned the hardware in the sense that I, I backed some, you know, former McKinsey types, when the times were good. And let me tell you, they were not the ones that stuck around when the times got tough, frankly, because they had too many other options. And they were too rational. And they were too much, you know, like I’m used to my lifestyle, I’m not as completely crazily, you know, devoted to this one thing. What does that if you work with founders who didn’t have many options, who, you know, frankly, were motivated almost completely and in some ways, maybe even you would say, it negatively is not the right word, but let’s say maniacally devoted to the idea, or like, you know, I remember I used to describe it, like people who are even angry, like angry at the world that the world’s not doing the right thing. And they were so motivated to fix it, that they were so driven by that, that nothing else mattered. And you find that Zelos end up making the best founders employee like, like, like people that so long, long answer to your question when I found out about talent, is that you want to put people around, you have people around you that are sometimes if not, most of the times very different from you that that makes for better, better outcomes overall. The second thing I learned is that, which I kind of knew, but it became even more important, this kind of job is that communication and kind of being being truthful, and like not hiding the ball at SE is very important in anything that is not transactional. And by that, I mean, in venture, you’re building companies, which not a single, like, it’s never about a single moment, or let’s say it’s very seldom is it about a single moment in time, maybe when we maybe wouldn’t get the chance to invest is a single moment at the end of the day. But if you’re working with someone who usually doing it to build value over multiple years, and in many cases, those same founders or employees going to other companies, so you building a reputation that actually goes way beyond single interactions. So a very transactional way of thinking or dealing or you like delaying the pain, are you trying to be nice here, but But it comes back to haunt you. So figuring out what it is that you stand for what it is that you can help with, and being upfront about that and also, but also being upfront and saying, I don’t know. And he’s like, You know what, I’m not the best person to talk to about that, which was, frankly, I’ll be honest with you. Very, very difficult for me to do. It’s very difficult for me to say, I’m not the birth birth, you know, these insecure overachiever types that I put myself in we all you know, Want to be good at everything and always have the answers. And that doesn’t help you in the in the in the long run. So when we think about talent, again, finding people who are complementary and frankly better than you to have around you was was the best thing I could have learned and


Will Bachman  45:18

talk to me about any courses or professors you had at Harvard, that continue to resonate with you whether it was professional or, or some side interest.


Andreas Stavropoulos  45:28

Yeah, well, I mean, that probably the one course that comes back to the most often just because it’s relevant. So many things is justice. Right. Michael Sandel, Justice philosophy, talking about you know, all these kind of philosophical questions and how they come up, I would say of all my classes, the one that comes up still that most often, when it comes to practical value, obviously, my computer science classes on algorithms, I think really taught me the, the ability to think systematically and break down problems in a way that works for me. So I think practically speaking, it was a lot of my CS algorithmic classes that helped him modeling and understanding the world. But if it comes to things I still quote, and still think of today will probably be justice and some, frankly, of these kind of core classes instead of my my pure, major classes.


Will Bachman  46:21

And one question I still had about Greece. So what many people might, you know, leave a country come to the United States and you’ve lived for 35 years? And just figure they’ll retire here? What was it that drew you back to Greece? It sounds like you’re planning to spend a good chunk of your third act, living in Greece once you’re an empty nester. What was it about your ties to the country that that stayed so strong, despite being gone for nearly 35 years?


Andreas Stavropoulos  46:56

Well hit out for people, if they do spend time there, what you see is that they’re still this. Greece is a very unique place in the sense that it’s a tiny country, you know, the entire country can fit within the state of New York, but it’s extremely varied otherwise, geography, climate, you know, sea versus mountain, food variety, you name it, right, extremely varied. So it’s a place that even though it’s small in geography, you can keep discovering, frankly, for multiple lifetimes. So that’s one. The second thing though, is frankly, quality of life. It used to be a very stark choice that you had to make between either have sort of, quote, unquote, quality of life, you know, free time, leisure, good weather, blah, blah, blah, or do well in my career. Those barriers are more industrial age type batters, we’re in the information age now. And a lot of the best work can happen from people in places where they feel they’re the most, let’s say, self actualized. So I’m actually another kind of reason why I want to be spending more time there is I’m completely bullish, that’s why I’m buying real estate and trying to do stuff over there. Because I think places like Greece, that have this spontaneity to them, the ability to not have to plan things way in advance, just by placing yourself in the environment, good things happen to you. they’re few and far between. I mean, Silicon Valley has it from a sort of professional perspective, this value of spontaneity, let’s say, Greece has it when it comes to the quality of life defined, as you know, read the blue, I mean, I’m sure you may have read this Blue Zone type book write about places in Greece and others, so that spontaneity and the ability to be around people with whom you feel both familiar, but also you know, that you can kind of have this ability to discover new things over time is a really unique. So I think that that’s one of it. The other one is obviously our parents and family, right? Loved ones that are back there a lot of our friends who have gone back. So I wouldn’t have said, If you had asked me 15 years ago, I wouldn’t have said that for sure, we’re gonna end up spending half our time in Greece in Ireland, say 60s. I think it’s a more recent thing. And I feel very lucky and privileged that the world is moved in a way that allows us to do that. And I think a lot of it has to do with how the nature of work changes and allows us more flexibility about where to be in the future.


Will Bachman  49:23

Well, I want to say thank you for sharing your experience and what a role model and I wish you success here and your third act and where Andre is can people find you online if they want to follow up? And yeah,


Andreas Stavropoulos  49:40

the easiest is the LinkedIn because that’s the one place where regardless of where I am at any given moment, they will come to me so if you look on my LinkedIn profile, you know that if you put it on the on the link, Andrea stavropoulos, you can find me pretty easily and I’m very good about responding to requests for folks with whom we have stuff in common and happy To help anyone that I can


Will Bachman  50:00

wonderful thank you so much for joining today


Andreas Stavropoulos  50:03

thanks well all the best thanks for what you’re doing