Patient Capital, Bold Bets: Constructing a Venture Book That Works

With Joshua Berkowitz,
Managing Principal, Berkocorp
This week on Swimming with Allocators, Joshua Berkowitz of Berkocorp joins Earnest and Alexa to share his journey transitioning his family office from real estate to venture capital, offering candid insights on building relationships with top VC and PE managers, the importance of patience and long-term thinking, and the realities of portfolio construction. The discussion covers how to underwrite exceptional managers, the value of GP and LP recommendations, and the evolving landscape of venture, especially the rise of young founders and AI-driven startups. Listeners will also hear from Shane Goudey from Sidley on trends in fund formation and the current state of the venture market. Key takeaways include the need for genuine interest and commitment in venture investing, the benefits of a diversified yet opportunistic portfolio, practical advice for family offices considering this asset class, and so much more.

Highlights from this week’s conversation include:

  • Joshua’s Background and Transition From Real Estate to Venture Capital (0:12)
  • Diversifying from Real Estate to Venture (1:43)
  • Commitment and Learning Curve in Venture Capital (3:45)
  • GP References vs. LP Recommendations (5:36)
  • Reflections on First Investments & Portfolio Design (7:24)
  • Deployment Strategy and Allocation Modeling (10:53)
  • Fund Formation Market Trends and Sponsor’s Perspective (16:21)
  • Underwriting Individual GPs & What Makes a Good Manager (18:11)
  • Suitability and Motivation for Family Offices in Venture (20:57)
  • Return Expectations and Investment Strategy (24:55)
  • Challenges with Fund Lives & Reclassifying Mature Assets (27:21)
  • Trends: Resurgence of Young Founders & AI (29:45)
  • Closing Thoughts and Next Steps for Berkocorp (33:11)

Berkocorp is a Canadian family investment office managing a Vancouver-based real estate portfolio and actively backing top venture capital and private equity managers across North America. Led by Managing Principal Joshua Berkowitz, Berkocorp takes an independent, long-term approach to capital partnerships, with a portfolio spanning micro VCs to billion-dollar growth funds. Learn more at www.linkedin.com/company/berkocorp.

Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com.

Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. 

The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only.

Transcript

Alexa Binns 00:12
We are thrilled today to have swimming with alligators. Joshua Berkowitz, Joshua runs his own family offer office Berkocorp, where he is responsible for having moved the investment focus, specifically on real estate, to backing top VC and PE managers. He’s actively looking at managers at this very moment.
Oh, god. What have I done?

Alexa Binns 01:04
Two of the things you’re going to speak to today are who shouldn’t email you and why, as well as some of what, some of the differences in underwriting PE versus VC, so that some of our LPS who are listening can learn what they might be needing to consider when looking at ventures.. On the venture side, Could you walk us through the thinking of why you wanted to add that in and how you approached it? Sure.

Joshua Berkowitz 01:43
So we started as a real estate family real estate business. That was all we ever did for about 60 years. I took over. I was sort of happy with the real estate business. But if you know much about Canada’s real estate market over the last, call it five years. Call it 50. It’s basically on a straight line, up and to the right till about 2020 and since 2020 sort of a weird roller coaster in 2021 and now it’s been flat, and there’s lots of underlying structural challenges that make me think real estate as a whole in Canada is going to be troubled for a while. And so I wanted to diversify, partly because I saw that, partly because I think diversification is just good and, you know, manages your risk better. And partly because I just wanted to write, like I enjoyed meeting venture capitalists and thinking about new technologies. I enjoyed the same thing with the private equity folks. And so we still own and operate all the real estate that sort of was, they call it our legacy business, but we shifted focus to diversify. And because I thought there was more opportunity in the other asset classes. Venture specifically, I actually think ventures. Ventures are really interesting, fit for families like ours. One, it’s very inefficient, right? Like the best venture capitalists are light years better than the worst venture capitalists, and the returns reflect that. And then similarly, the returns can be very good if you feel like you can consistently pick the top venture capitalists. And then, you know what’s sort of the advantage that families like ours have, which is that we have a really long term mindset. We don’t. We do not. We’re not huge spenders. We don’t need the money. Eventually we’ll give it all away. We can be patient. In fact, we’re sort of patient by design. And so the illiquidity and the long term thinking, uh, all fits well with sort of the family office mandate, and that sort of the last piece of the puzzle is taxes as well. We don’t have USPS in Canada, but nonetheless, super long term compounding assets that produce capital gains is about the most tax efficient investment you can make. And so also, from a tax perspective, the fit with the family office adventure is really good.

Earnest Sweat 03:46
once you’ve done that, then it’s like, all right, how do you start to learn and get good at it? It’s still an inefficient market, even if you go in with eyes wide open. But then how do you learn?

Joshua Berkowitz 04:25
if you’re gonna do it, you really have to make a significant commitment of time and travel to make it make any sense, like you should probably think you’re gonna have to meet at least 100 venture managers before you’re before you have a good sort of calibration on what good looks like, and probably you’re going to have to do a bunch of bad deals first, or call it funds you wouldn’t do a few years into the business, because sometimes you know that that’s going to it’s going to be a lot easier to get into riskier, less performant fund than it is going. To be, get into the hot, you know, ones that have performed well for a long time. So I think before you do it, decide if you’re going to make that commitment. Because I think in 2021 especially, you saw a lot of families sort of, you know, get getting really excited with adventure, because they saw all the money that was being made, and they just jumped right in really fast with large commitments to, you know, one of the first five managers that pitched them, and now they’re probably regretting that, and they probably going venture, sucks. I don’t want to do it anymore. And quite frankly, that also hurts the entire ecosystem, because now GPs are back a few years later, going like, well, I, you know, I need to meet a whole new set of LPs to raise my fund. And that’s not good for anybody. So I think, like, you should really look in the mirror first and say, like, Am I willing to make this commitment to the asset class, so that the last piece that adds to that is you don’t know, you’re good at this for at least five years, right? Like, like, the GPS, don’t know, but actually the for five years, but actually as a as, like, the timeline on this, you make a commitment to a fund this year, they’re probably not calling capital at the beginning.
Alexa Binns 08:17
Do I hear you sort of saying you prefer, or you value higher the GP to GP recommendation versus an LP recommendation. Or you’re sort of building your own conviction based on, I mean, when you’re sourcing is that coming from

Joshua Berkowitz 08:39
to some extent, I think it depends on what kind of manager, and it, quite frankly, depends on the person, right, if you’re if you’re like, so there’s a first time GP, or even a second time GP, the only people who know how good you are are people who’ve worked with you, right? Like, like, just a matter of fact, there is almost no way for me to reference a first time GP from other LPs, like you don’t have any other LPs really, or even if it’s a fund one, you’ve had LPS for sorry. Fund two, you’ve had LPS for two years. They don’t know that much about you yet. So who’s going to know you? It’s going to be other people you’ve worked with in your professional life. And so as an investor said earlier, that’s another GPS. And if that’s as an executive or founder earlier. It’s sometimes you as the founders investors, which are also, by the way, GPS. So yeah, I really, I really value GP references and recommendations a lot. That said I value some GPS recommendations a lot, and others less a lot. And then I think it does shift a little bit for third and fourth time funds, because then LP recommendations really matter, because they’ve spent a lot of time at this point with the GPS, there’s more of a track record to understand. And so I. So I think it shifts a little bit for the more mature funds where the LP recommendations are more valuable.
Earnest Sweat 10:43
for your first investments, what were the kind of key learnings you got out of it.

Joshua Berkowitz 11:21
The first like, my like, experience of doing this at the beginning was meeting all of these super successful, super smart people that have made a lot of money as an investor, as a founder, and they’re all like, wildly more networked and knowledgeable and everything than me about about venture and, quite frankly, in many cases, just about, like life and business. And so you just want to say yes to all of them because they’re so damn impressive. So that was the first expression that was like, I want to say yes to all these people. Damn they’re good. You wouldn’t have been, you know, you wouldn’t be a VC if you’re not really impressive. And then you’re like, well, now I’ve met 25 impressive people. I can’t say yes to all of them. Yeah, all right. Which ones are more impressive? Why? And so, like, I still think highly of the first people I said yes to doing this, this job. I think they’re really smart, really talented, and really capable. But are they as really talented and as really capable and as disciplined, as good investors, whatever, as I think the current crop of folks, I’m sort of saying yes to No. I think the bar has gotten a little higher.

Earnest Sweat 18:01
You know, in our prep call, you spoke about your portfolio being a mess by design. Can you share what that means and why you embrace it? I just think

Joshua Berkowitz 18:10
it’s a lot more fun to call it a mess than it is to call it diversified or opportunistic, or opportunistic. Sure, yeah, whatever the professionals like to use to describe the same thing. Like, what is a mess? A mess just means diversified. It means opportunistic. It means I want to invest in the things that I think will make money, not paying much attention to what vertical geography stage, sort of like the silly classification you want, or the box you want to put a manager in. Like, the most important thing I’m like, the most important dialog running in the back of my head when I meet a GP is, are they going to make money? Right? Like, that’s ultimately why I’m doing this. Make money by helping, you know, fund great companies that will hopefully matter. There’s so many ways to make money in venture so so many from, from going super early stage, super late stage, to international, to domestic, to everything in between, doing funky secondaries, doing employee buybacks, like, you name the strategy I’ve been pitched in and heard it, and I think some make sense and some don’t. If I was worried about things like, I need to find a deep tech manager based in Austin and a health tech investor based in San Diego, and a farm manager based in Boston, that would just tie my hands behind my back and stop me from asking the most important question. Do I think this strategy makes sense? Do I think this person is amazing? Do I think they’re gonna make a lot of money and so as a result of turning off the Like Box checking exercise, you end up with a bunch of really differentiated funds that are actually pretty different from one another. So I do think they’re diversified. They’re just not diversified across, like the traditional metrics. That traditional asset managers, or wealth managers or whatever would sort of try to diversify against, right? Like, the classic is like the stage geography sector. I don’t think about which I have all the sectors covered?

Alexa Binns 20:45
a piece of that that relates to also how you’re thinking about your deployment? I’m curious how regimented you are in terms of

Joshua Berkowitz 20:58
So there, there. I probably follow what the institutions do far, far more, far more than anything else. So, as a family office, investing in a venture, generally speaking, you have a target allocation percentage. You say, I want 25% of my assets, whatever it is, to be invested in a venture, you know. And therefore you have X dollars today. In order to get to that target allocation, you’re going to build a cash flow model and say, oh, I need to commit X million dollars per year into the venture. It’s going to get called over the next many years. It’s going to be invested for many years. It goes back many years. So in order to get to my target allocation, I need to commit $6 million a year. I am absolutely running that model. That is exactly how I decide how much to invest every or how much to commit every year, that every half year or every year, or to make sure I’m pacing as expected, adjustments based on everything else going on in our lives. And that is what helps me get to the commitment size number, so that that is super important to do. Because I also think like when one failure mode here is to say, I want to invest $10 million in a venture in your first three years, you commit $3 million each year, and now in your fourth year, you’re like, Well, no more money for a venture for 10 years, great. And then you come back to 10 years later, like, how did I do that? It is a very, very bad way to do this job. So instead, you need to do it more slowly, and you need to make sure that you’re sort of never out. Because also, you always wanna make sure some percentage of your portfolio percentage of your portfolio is new managers, and quite frankly, that you’re saying no to old ones. Because also, if all you’re doing is re upping with your existing set, sort of definitionally, that means it’s like you’re missing all the good ones, and you’re not constantly trying to raise the

Earnest Sweat 22:38
bar. Now we’re going to take a quick break to speak with our sponsor

Alexa Binns 22:42
On the show today, we have our stellar partner and industry expert, Shane Gowdy. He’s the leader of Sidley venture funds practice. And if you get value from this podcast, we have Shane and the Sidd team to thank for it. They make these recordings possible. We are looking forward to hearing from

Shane Goudey 22:58
you. Shane, no, I’m delighted to be here. Lexi, it’s been a wonderful relationship with you and Ernest and swimming with alligators. You guys are the best, so we’re glad to be part of it.

Alexa Binns 23:08
You are very kind. It takes a village. It does indeed. You lead the venture funds practice at Sidley. Could you just describe for us the team and the work you do.

Shane Goudey 23:21
Yeah. So my focus, my day to day focus, is working with venture capitalists of all sizes, shapes, creeds and colors. You know, the multi billion dollar per fund, asset managers in the business, running all the way down to brand new, emerging managers forming a five to $10 million fund. It really, truly is an entire ecosystem practice, purposely agnostic, because the fun is in who you get to represent on a day to day basis. So we really do it all, and you know the part of So I’ve started at Sidley. About a year and a half ago, I was at another firm for a quarter century. So I’ve been swimming in the venture fund waters for a very long time, and they are wonderful waters to swim in. I find myself just energized and refreshed and loving what I do here at Sidley, I am the head of the venture funds practice. Our funds practice is, you know, quite sizable. It’s about 140 lawyers representing all different sectors of the investment management space. I was brought over to Sidley, to really bolster and build the venture fund side of the practice. We have a nice, robust emerging companies practice. But in order for us to be able to represent the full ecosystem. I was brought on to kind of be the last piece of the puzzle to help us really maximize our opportunities. So the team is now about 25 lawyers. It was, you know, one me about a year and a half ago, and so we’ve aggressively built, and certainly used a lot of internal associates to build. Our team, and now we have a really great practice of people who through lateral, partner and associate hiring from key other firms with deep experience and really the right frame of mind for how to represent VCs in doing this work, because I think there are a lot of people who can do the work of representing funds, but actually, it’s not just doing the kind of fun formation you have to understand the market and the mentality and what it really means to be a VC, and how that reflects itself in a fund formation project. So, you know, we’re really building kind of a practice that is built to be the concierge service for venture firms of, you know, any size, any shape, and we’re kind of built for speed and, you know, built for quality, and we’re really excited about what we’re doing. And, you know, the firm’s been incredibly supportive, and, you know, we just, you know, we’re enthusiastic to be a really great part of the venture ecosystem. So it seems

Alexa Binns 25:57
like, as you’ve been building the team, we’ve also been seeing momentum build on the fund formation side. Can you share just anecdotally, what you’re feeling here in the end of 2025

Shane Goudey 26:12
Yeah, no, no, it’s absolutely nice to have to build a practice when things are getting busy from a fund formation standpoint, you know, it is as busy as it has been in the last three years. This is naturally a time of year when a lot of funds are doing their fundraising plans over the final quarter of the year to be able to kind of have a closing, first closing around January, late January, early February, to take advantage of the fresh buckets of allocation for very large venture investors, but also people who you know, whether it’s family offices or high net worth, you know, fresh buckets of capital in their own kind of personal stakes to be able to invest. So just the natural time of year is great, but, but the market is really good now, right? We’ve got a lot of M and A and IPO activity. You know, I’ve heard of a couple Spax back again. So, you know, the upside of the market is very busy providing liquidity for a lot of venture firms. And that obviously, is the fuel in the tank for any of these firms to be able to fundraise, you have to produce returns. And from a time over the last two to three years where there hasn’t been much of that, or you’ve had to be very, very creative about how to create secondary opportunities. This tends to be kind of relying on some of the more natural channels of M and A IPO activity to have hope, at least that things are starting to turn around. And if I look at the number of funds that are out there now raising, you know, these are, these are more, certainly not 2021, days, but you know, big markets, which have sort of been the hallmark of the last three decades, these are kind of the, a little bit of the evidence of what’s gone on in some of those markets. So we’re pretty excited and in our sector of the world. And now

Alexa Binns 27:58
back to our LP interview. I so

Earnest Sweat 28:02
In that piece, I would love to know how you’re thinking about underwriting the individual GPS. Let’s first start with net new relationships, because I can infer that like, yeah, you’re very by the book when it comes to how much you’re deploying and your deployment schedule. But I get a sense that from what you’ve said, You’re not prescriptive like what you think you should be investing in. It’s more about the people that get to meet. So talk about when you meet these people set, what are you looking for, and how you underwrite

Joshua Berkowitz 28:35
there’s not really a formula. You’re looking for a buddy, somebody that is really, really special and has a set of life experiences that shows just how special they are, and then you’re looking for a strategy that fits that perfectly, that fits them is who they are, like person or team, right? As a result of what I just said, there’s 1000 ways you can have impressive backgrounds, whether it be founding a couple founding a company, whether it be being a great investor, working at a great institution, you know, coming out of one of the main impressive sort of institutions that makes the value run like twice here the tee fellowship or whatever. There’s so many different ways you can have a really impressive background and have a lot of reps of meeting, identifying and picking great founders. I am not prescriptive about it, but the important thing is that you are truly world class at the thing you’re I don’t think you are. Like, top venture is a game where if you’re the best people, you don’t make money at all. And so you can’t say, Ah, they’re really, really good. But I think there’s like, a couple levels above them, like, then just don’t do it right? So you want, like, the best team, and you want them to have a strategy and sort of approach that you think is perfect for who they are, and that as a result of, you know. So if so, if you find a person who you know, you. More manic and aggressive and like, goes to all the parties, goes to all the events. Knows everyone needs to stay on top of everything. Like, probably a strategy that has them doing a lot of deals, and, you know, using that momentum and hype to get into sort of the more expensive rounds. Like, makes sense wherever you have someone who’s more cerebral in developing theses all day and doing research with founders and industry experts and sort of trying to find overlooked startups in weird areas that fit market opportunities they’re excited about, like that’s just going to be a different strategy from a different person. Both can be successful, and there are examples of both of those strategies where they have been the most important thing is that they’re world class at executing, executing, and that they’re the right type of person for the right strategy. It’s always interesting having family offices on because, you know they always say, if you meet one family office, you just met one family office. Where do you think it is? I know you gave kind of the reason why you did it, and you felt like your family should be investing in a venture. But overall, where do you think, like, what types of families should be? Who would be perfect for for venture cap and who should just stop right now,

Joshua Berkowitz 37:12
I think the most important thing is that one of the principals likes it for all the reasons that I sort of explained earlier why it’s hard, right? You gotta meet a ton of them. It’s pretty opaque. You have to do it for a long time before, if you’re you know, if you’re successful, there’s lots of illiquidity. There’s lots of love, fear, uncertainty and doubt as a result of that illiquidity. Like, the most important thing is you have to like it, because if you don’t like it, you won’t stick with it, and you won’t through the BS to what is true, and have the patience to sort of see that out. And so if investing in working in the world of venture and tech, you know, with amazing young founders and amazing GPS backing them. Like, if that’s not exciting and fun to you, don’t do it. Like it’s just not worth the brain damage. It’s too small in asset class, it’s too idiosyncratic, it’s too hard to understand. Like, you shouldn’t do it. But vice versa, if you find yourself reading the tech news every day and wanting to know what is happening in the ecosystem that, quite frankly, is driving the entire world forward, and also working with optimists. Like in order to be in tech, you literally have to be an optimist, because, like every single founder has a 25% chance of success, and yet they all think they have a 90% chance of success. And every GP has a 25% chance of making decent returns or less, and they all think they have a 99% chance of making decent returns or more. So all of us are kind of full of crap, but it’s optimistic, full of crap, and that’s awesome. That’s like a better way to live like you’re, life will be more fun for you if you are a little bit too optimistic than a little bit too negative. But some people can’t deal with that, right? You know, you’re going to meet eight founders that I’ll tell you, they’re changing the world, and they’re going to be successful. And in the back of your head, you’re going to know that’s not true. And some people react to that, being like, this is all crap. I don’t want to do anything like that. Others react to man, I love the energy in here. I know the reality is this is way harder than everyone’s making it seem, but I’d love it. I still loved the energy and the vibe, because this is how good things happen. So you need to have that frame of reference too. So I think that’s, that’s like, fundamentally, the most important thing, right? Because, because, because, all the money, aside, the opportunity that, like me trying to prove to you that this is way to make money as a family office, none of that matters if you don’t like and I’m not going to stick with it and do the work to to get over that hump, that, that’s what I would say. So sort of like the pattern I see in ventures at a lot of family offices. If you’ve made your money in tech, naturally, you’re just way more likely to do it that makes perfect sense for the other families. Often, your first exposure to it is you have a family business in industrials or real estate or pick your. Pick your vertical and so maybe the first step is go invest in a venture fund that’s focused there. Yeah, because then you get other value out of it, other than just the investment. And so even if you have your money stuck in an illiquid fund for a long time, you feel like you’re getting value from talking to the GP. You can add value to the underlying portfolio companies, and that gets you interested in a way that is more visceral than just, you know, numbers on a spreadsheet. And so that’s also a good way to, like, dip your toes into it as a family offices like, go invest in the funds that, like, have a real connectivity to what you’re already doing, and then decide after that, do you want to keep Yeah,

Alexa Binns 40:37
do you have return expectations that are leading you, either earlier or first or second time funds or, you know, some family offices. I think the way they’re starting to dabble is through some of these products where you can invest in really established funds. Curious what, what the role of your VC investments are,

Joshua Berkowitz 41:02
I think that the family office is investing in the established fund. Like, part of the logic there is that you don’t trust your own intuition and judgment, and so you’re using the brand name as a replacement for that. Like we do that in everything in our life, right? Like, why do we shop and go to the store and buy lays potato chips instead of house brand or whatever. It’s because our brand is, is, is giving us the safety and security that the product is a good one. And so one of the things that the mega funds have been really successful at is branding themselves. And so family offices see Andreessen Horowitz, Sequoia, General, catalyst, flight, speed, whatever, and they go, I know them. They’re an XYZ company I’ve heard of. Like this feels safer to me. I can trust the brand name, and so that’s a super reasonable way to get started. Makes sense to me. And quite frankly, if you haven’t developed your own investment judgment, like that’s actually what you should do, yeah, first because, because I wouldn’t trust your investment judgment either. But if you, you know, if you, if you decide, I’m going to be a real practitioner of this, then sort of naturally, you go down the path of ignoring brands and doing the work yourself and deciding what you think is the best return. I wouldn’t say I have, like, explicit return expectations. I will say I’m an IRR investor more than a tvpi investor. I hate the I hate, I hate the adage of, like, multiples over everything. Because, especially as fun lives extend out. Like, if you get a Forex in 12 years, like, that’s not actually a good return. And you can invest in plenty of two, if you can invest in two, 2x funds over that period of time, do that get extra liquidity in the interim?

Alexa Binns 42:43
Joshua, um, one fund investment I made a decade ago, and they are still they’re on, like, number 55

Joshua Berkowitz 42:52
They are playing this IRR game. My total wire fees are, like, $1,000 from this fund.

Joshua Berkowitz 43:03
Well, I forget who it was? Hamilton. Lame data. I read some data that said, like, the median venture fund doesn’t return 1x dpi for like, 17 years at this point. Just crazy to think about. So what I’m doing is in my cash flow model, just extending up the fun lives of most of these things, how far I put a fun life of 17 years in. And honestly, maybe I should, maybe I should make that 18. That’s insane. It’s nuts. It’s nuts. Very at the same time, I think there’s like, aside, but like, let’s suppose you invested in a fund 15 years ago, and stripe is their major position left, yeah. So now you have stripes on your cap, right? It’s in a fund, but it’s basically just stripe that’s also not really a venture investment, like, doesn’t have venture risk, it, it, it’s a big, established company. You know, we could argue about what the price is, but I would say it’s comparable to owning lots of other public market stocks, just without the liquidity. And so there is, like, a thing I ask myself, I hope other LPs are asking themselves, which is, if you have this big mature portfolio of real companies with real revenues, hopefully they’re profitable and they’re growing. They’re just not public yet, and so they’re durable. They grow stage businesses like, should they be in your venture bucket, or should you move them into private equity or growth equity or something else? Because the underlying risk asset is no longer venture risk. It doesn’t behave like a venture. And so, you know, if you think a typical venture book is now half of companies like that, maybe target allocation to venture should be up a little bit. I think we have to figure that out. The ideal solution is that we just get better at liquidity and people sell things faster. Like, that’s the actual ideal outcome. But short of that, that’s not going to happen. I do think we need to ask ourselves, like, what is the underlying character of the risk in a venture book that is very mature? Yeah. And is it fair to sort of classify the whole as a venture and therefore get a small percentage of your allocation, or should it be bigger than the risk is actually lower over time?

Earnest Sweat 45:11
Are there any trends that you’re like, really following as far as in venture? I know AI is a big one, obviously, but that is helping you scope out things like, oh, what I need to be looking for in managers over the next five years.

Joshua Berkowitz 45:27
The first one that comes to mind, it felt like the period from 2015 to 2022 there weren’t that many really young founders anymore. It felt like the average age of folks was getting older. There were more repeat founders. The businesses that were getting started were in more complex industries that often required a bit more gray hair experience. I can’t prove that, but it felt that way. And in the last two years, it feels like that trend has, like, reversed really fast, especially in in AI, in AI land where the companies that are winning are the ones that are just moving so fast and working seven days a week, and are often 20 year olds who are best at using all the latest tools and completely changing how they work. And so if you believe that’s a trend, which I do, then you need to go, Okay, well, the types of VCs that are going to back the 22 year old kids are probably different, at least at the very early stages. Are probably different from the folks that are more reliant on their existing founder networks and like existing sort of, you know, in the ground relationships. It’s partly why it was contracted to the dorm room fund? There’s a few others that I feel have had good exposure to that ecosystem, in that world, that are, you know, backing the younger, younger founders. Josh Browder, is one I just backed, that invests in a lot of those younger, younger teams. So I think that’s one that I’ve definitely been producing.

Alexa Binns 47:02
I think the repeat founder argument makes a lot of sense when you build companies using a particular playbook. But now that we don’t have that many examples of companies that have been built, AI first AI up, then somebody who’s got all the time and energy in the world is going to be just as an attractive bet. Yeah, those repeat founders I want to invest in. Ai repeat founders. I want to, I want to get my money in after they’ve done it a couple of times. You know, once you’ve had a couple of

Joshua Berkowitz 47:38
bets, that makes sense. It is remarkable, though. Just like, I think, how old are the like, the cursor guys, the mediocre guys, like those teams are like, so, like, you, literally, this is your first job, or you dropped out and like that, hasn’t? We know the collisions and Alexander Wang at scale and mark, but there’s not that many of those. The fact that I can, like list the famous ones, sort of shows that, but it feels like this, this generation working a lot, which is kind of awesome, but I do think requires a bit of a different way to think about, you know, getting getting early stage exposure,

Earnest Sweat 48:17
I guess the last question, Joshua, I just want to know what’s next for burka Corp, Berkeley,

Joshua Berkowitz 48:25
in venture land. I, quite frankly, I think I will be running this strategy forever. You know, I think around the edges is, you know, how should I think about CO investing? You know, there’s a few other things in the back of my mind. Is that, if you know, if I want to deploy more to venture, I think there’s some interesting opportunities around the edges like getting involved in, in prospective VCs even earlier in their journey, maybe allowing some to invest off my balance sheet before they’re ready to start a fund. There’s some sort of ideas around the edges I have like that. But for the most part, investing in funds that I think are exceptional. Like I love doing it. I love the people I work with. I love being able to help in whatever small way I can. I love hearing about the companies they’re investing in and seeing them grow and impact the world. So I, by and large, I, quite frankly, expect to keep doing what I’m doing for quite a long time.

Earnest Sweat 49:27
Well, thanks so much for being on the pod. I really appreciate your stories. For part two, we’ll get more into you know Joshua has a great mind of all things macro as well. So maybe that’ll be another podcast that we do, but that’s great. Thanks for being on Thanks,

Joshua Berkowitz 49:45
guys. A lot of fun. Spend time with you.

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Earnest Sweat

Earnest Sweat is the Founding Partner of Public School Ventures, a dynamic syndicate of over 600 technical operators, go-to-market specialists, and LPs. Previously, Earnest built new venture capital practices at Prologis and GreatPoint Ventures. His focus is on investing in value chaintech, specifically vertical SaaS, applied AI, middleware, and B2B marketplaces, which are poised to revolutionize foundational industries like real estate, insurance and supply chain. Earnest has sourced and led investments in companies such as Flexport, Flexe, KlearNow, and Lula Insurance.
Alexa Binns

Alexa Binns

Alexa Binns is an angel investor and LP. An experienced investor and operator, she has climbed the ranks from associate to partner at Maven, Halogen, and Spacecadet Ventures and built digital and physical products for Kaiser, Disney, and Target. Alexa has worn every hat in venture from fundraising to sitting on boards. She invests in companies with mass consumer appeal, focusing on the future of shopping, health/wellness, and media/entertainment. Key angel investments include The Flex Co, Sana Health, and Chipper Cash.

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