Playing Chess: Real Estate-Venture Barbell | Ashley Flucas

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Okay, I'm very excited to welcome a special guest and friend to the Owner Mode Summit, Ms. Ashley Flucas. She is someone who is... Been around my orbit for four, maybe five years now. She's always been someone who, in my opinion, is operating at a grand master chess level when it comes to this game of earning to owning. She has an incredible story. She's the COO of Summit Ventures and also the general partner and founder of Flucas Ventures. We're going to dive into her story, but what we're going to talk about, you know, in detail in this session is really this idea of almost structuring a private market portfolio. in a way that optimizes current income, lowering your effective tax rate, but also, we're calling it the barbell strategy, exposure to high return opportunities through venture investing as well. So with that, Ashley, thank you for joining us. Appreciate you taking the time. Thank you for having me. And I hope you can do all my introductions going forward. One thing I love about Ashley is that she's an independent thinker, right? She is someone who does our own research and what I consider, you know, to be one of the more thoughtful folks around this idea of a holistic diversified portfolio. And it all kind of started with independent thinking in the earliest stages of her career. So she went to Duke undergrad, she went to Harvard Law School, you know, she got the big academic credentials. But there's a story around how you kind of got off the beaten track. So maybe let's start there, Ashley, in terms of, you know, what your initial... professional aspirations were, what was the realization for you in terms of thinking about things a little bit differently and how you arrived to where you are professionally today? Yeah, that's a good question. So yeah, mean, back in those days, even going back to college and law school, I didn't even imagine that there were career paths that available outside of like a box of things. was like, okay, if you're a smart person and you want to be a high earner, you can be a doctor, lawyer. management consultant or investment banker. I thought that was like the only path, but I always just kind of had this, you know, propensity for wanting to be around deals and deal making. But I didn't really want to do that in a banking or consulting capacity. And I'd always been, you know, kind of more verbally strong. So I ended up choosing law for a couple of reasons. One, It was just a path that so many black people and black women have already trailblazed. So I kind of knew there was a path to success there. But then also I just, you know, read a number of, you know, anecdotal stories of people that, you know, started off in law, but then transitioned into other things in business and how, you know, that legal background just ended up being kind of a tool in the toolkit. you know, you know, ended up going to law school. At that point, the decision tree, said, okay, I'm also going to not pick a discipline that gets me in that deal framework, right? So I started doing international capital markets law. practiced in London for two years. And it was actually during that time, I read this book called The Monk and the Riddle by Randy Komisar. And that's what really started to turn my gears about, I think the deals that I actually want to do are like private deals and investment. His story was very similar. went to law school, I believe Harvard as well, was going down the traditional path and just was like, you know, I don't want my life to just be me progressing, you know, office by office till I get into the corner life, excuse me, the corner office and that be all that there is. So he, you know, kind of went left, did some things in business and then ultimately ended up. doing things in venture capital and being wildly successful there and went through some of his, war stories, his way of seeing venture capital, and some life stuff as well. And I was just like, that was the first time that it really clicked for me of like, that's how I want to design my life, but also this idea of designing your life. But, you know, at the same time, I'm like, you know, yes, I went to these, you know, prestigious schools, et cetera, but I'm, I'm not in tech. don't have friends that are in tech. I'm in London at the time. I came back to the U.S. I'm in Florida. There's no even, there's not even the burgeoning Miami scene. This is, nearly a decade ago, but I was just determined to figure it out. I'm like, there, there has to be a way we are at the time it was 2018. Like it has to be a way. So I'm just, you know, Googling or researching, eventually stumble upon AngelList. And I see like, okay, people are making this happen. Like online. so, you know, one of the best ways for me, and I, I think it's helpful for a lot of people is I'll learn by doing right. Like if you just keep studying, you'll get analysis paralysis. So I'm like, okay, I just got to take some money and invest in stuff. Nothing that's going to cripple me, but I just need to crank out deals. You know, turn on the faucet as far as deal flow and learn, you know, in some, some ways it'll be the hard way and some, maybe I'll get lucky. So I started doing that and. You know, I just, it was like dopamine rush, right? I got addicted to doing that. and then eventually I started seeing so much deal flow through that platform. And I also just use that platform as an opportunity to network. was finding other people who were angel investing across the world, across the country, getting on Zooms with them, having conversations, picking their brain. And again, just learning through osmosis, and doing, and you know, after kind of two years in the lab. I was just kind of like, okay, like I'm putting my money into all of these other people's SPVs. was like, I feel like I could do that myself. And that's kind of always my, my, my attitude is, is not, I never really feel imposter syndrome. Like I always feel like I belong and I can do it. And just if I put the, if I put the work in and put my head down. then I started in 2020, I launched my first, SPV. It was a pretty good deal out of LATAM called Foodology. After I came in, Andreessen came in, I worked with someone else who was a more popular syndicator, which also kind of put a halo around my first deal. And then before I knew it, it just started going vertical. Like I had no idea, I know I wanted to do it, but I didn't really have, you know, targets for doing it. You know, within, you know, a year of doing it, then I was getting profiled by the New York Times. Within two years of doing it, I had a hundred million of AUM. And so on and so forth. And so, yeah, just continue to stack it. But the main things were, you know, it no special superpower, no special expertise. It was just about curiosity and more important than curiosity, taking action. being willing to take your lumps and just learn and do it. So there's a lot, a lot to unpack in there. So let's get to unpacking. the mentality, you read this book, The Monk and the Riddle, it led you to say, okay, look, you know, I've kind of gotten these prestigious degrees. There's this prestigious kind of well- trodden path that a lot of people in my position take. This does not feel good to me in terms of the life I live, basically. And so you kind of had that moment of clarity. From that point, it took some courage to explore some other options, as you mentioned. You don't really suffer from imposter syndrome. You get exposed to things. Let me try my hand at it, see how goes. Let's start with goals. So what were your, at the time, right? You know, when you made the decision that you're gonna explore something maybe off the beaten path, what were your financial goals, your professional goals as you explored what was going on? So in other words, how are you thinking about risk? How are you thinking about, you know, was your true north to hit a certain number and retire and you were trying to accelerate that place? you had kind of established you didn't want to just do the cookie cutter route, but what was the framework that you were thinking about in terms of a balanced portfolio, professionally and financially? Yeah, that's a good question. I mean, one thing, like I said, to be clear, so I do all of this in venture, real estate, even public markets, but I still have a day-to-day operating role as COO. of Summit Ventures and, one thing for people to be mindful here, you know, I haven't structured it and I don't necessarily encourage structuring it until you maybe hit your number, that you can straddle both. was like, the good thing about still having run that traditional path is that's the cash engine. At the end of the day, you know, there's a million ways to say it, but money makes money and money has gravity. And so. There are two ways to do that. There's obviously you're a good to high earner and you use that and grow that money or to leverage. And that's what the syndicating was for me is that I could lever capital. But as far as goals, when I first started doing it, mean, the whole thought was just really, was really financial independence. Now I can't front every... Every time, every, every time the number seems to keep going up of what I would actually need to kind of, kind of walk away and focus on it full time. But that's really what it started out as is like, you know, I'm a big proponent of kind of reverse engineering, right? So if you take a step back and say, you know, what, what do I, what are my needs? What are my wants? What do I want my cash flow to be indefinitely? You can literally model that and come up with a number and then starting from your base, you can figure out what you kind of need to do to get there. like I said, obviously, you know, I, I'm no different than anyone else. Sometimes you get lifestyle creep and other things that can ratchet that number up, but that was, that was the goal, right? I just also, I knew that I was a high earner, but you know, these high earnings situations are also golden handcuffs. And so if what you value is autonomy, which is, frankly, the number one reason why I'm chasing money is to ultimately get to autonomy without sacrificing lifestyle, then, you know, that that's what you had to have in mind. So I sat down, like at the end of the day, if I earn well and I just put my money in the typical things, like, yes, I will look up in. whatever, 20, 30 years and I'll have done well and had a nice life. But I was like, I want to accelerate that timeline. And if I'm right, I can greatly accelerate that timeline. Maybe that becomes 10 years instead of 20, 30 years. If I'm wrong, I was working anyway. So what difference did it make? But I'd rather go for it than not go for it. And so just for the audience to kind of... you know, one, put some respect on your name, but also kind of structure your journey. I think you hit on something that's really important here, which is you never left your day job. You shifted your day job into something that was in alignment with your goal, which was to accelerate to a place of freedom and autonomy. And so not leaving that role, you're willing to take on the extra work, getting busy and building up a venture portfolio through a fund that you started. And so there's a couple of things I want to kind of pull the thread on. When you made the decision to leave kind of the traditional role, you know, you were in London, Davis Polk, Greenberg Traurig, you know, the big kind of white shoe firms, you made a professional move into a different situation. What was your set of considerations when you knew that this was going to be something that you were going to put in parallel with another track? And we'll kind of get into the venture side in a second. Yeah, so... Oddly enough, even though, you know, even though I went to these prestigious schools, I am not, you know, that is not my end-all be-all. Like I don't collect gold, like I don't collect gold stars. And I think when you get into the professional world, you have to get a little bit out of that mindset of like, I have to work at this name brand company and I have to get... this title and this title and this title, because that's a little bit of, like I said, just being on the treadmill, it's nice and it's a little dopamine hits and you've probably just been on that steady ladder your whole life. But if you really want to go vertical, you got to be willing to think outside the box. So when I came back to Florida, I spent less than a year at Greenberg Traurig. At that point, I knew I wanted to go work at a company, get outside of kind of the white shoe context. And I started working out of this company, never heard of them, didn't even understand what they did, but there was just this like kind of entrepreneurial energy, capital raising and things that tied into my capital markets background. And I just had that feeling of like, can make, I can make moves here. Like, no, if I go to a cocktail party, nobody's going to have any idea. who I work for, I can't name drop, but like, I'm really gonna be able to learn some things, have, you know, access to important relationships, do some things that you know, ended up being good from a tax perspective because of the way I'm compensated and access to real estate deals. So I took that leap and at the time I was evaluating things like I was looking at a job at NBC. some other conglomerate, an NFL team, et cetera, which would have been a nice life, but I was just like, I'm going to do, do the different thing. And I did. and that's played out tremendous, you know, tremendously, but it's just kind of saying to yes, being willing to get outside of the box and not being consumed with the sexiness or what something looks like. I'm here to make money. I'm not here to impress other people. make money and save money. And we're to get into this part in a second, because as you kind of enter into this role that maybe didn't have kind of like you said, the gold star associated with it, but because you had a really clear vision of what you were looking to accomplish, strategically, this made a lot of sense because you were able to spin up Flucas Ventures. You talked about being able to have obviously the cash flow of the job, but you also had these interesting tax advantages, which many of the folks listening right now in the audience can relate, which is the high earner, high tax conundrum, particularly on the coast, right? So tell us a little bit around how, you know, this is where we're getting to the chess part of the conversation, how you would have been able to not just make money, but save money through the tax benefits associated with your role. And it would be helpful, I think, for the audience to understand what kind of paths would allow for people as they think about, you know, maybe going off the beaten path, what are the kinds of profiles they should be looking for to maybe unlock some of those... chess strategies so they're not just making money, but they're also able to keep money through tax strategies as well. Yeah, it's a good question. I would say step number one, because frankly, there are so many possible tax strategies to take advantage of, but rule number one, and that's actually something that I learned from being a deal lawyer, when you've got any sort of transaction that is happening... The first people you need to go to before you spend, you put pen on paper is you need to go to your tax guys and say, what is the optimal way to structure that? Because if you get down the road on a deal and you've done all this work and then it doesn't work from a tax standpoint, or you went down a certain road and okay, maybe it's a great deal, make a lot of money, but you're getting hit at ordinary income. But if you had done the right thing structurally, you know, maybe it was capital gains and that's the difference of, you know, 20%, that is huge, especially when you talk about big numbers. So that was that same mentality going into this field was I was like, rule number one, I need to understand what is there to understand about all the different tax plays around this. And it's so much easier to do now because this is also before large language models and AI. You know, I'm on Google reading articles, reading books, all this stuff now. You can ask ChatGPT to explain it to you like you're five and have all of the alpha of all of the alpha right there. But, you know, I realized a few different things. one, one of the things that attracted me to venture is this QSBS, tax situation. so I'm really going to, to dumb it down, but. everybody please feel free to look into it. But basically it was this idea, if you invested in startups, you know, there's limitations for how many assets they could have as well as a certain holding period. But basically, you know, the first $10 million of gains was tax free. said, huh? So that, obviously, you know, risk adjusted returns, right? We know the rates with startups, but I'm like, okay, that's That's, that's very attractive. And of course there's IRA and 401k and you should look at all that stuff too, but it goes, it goes deeper than that for me. Yes, I have an IRA. Yes, I have a 401k, but I'm also like, I also want to access a lot of my money now. so I do primarily use taxable brokerage now in this real estate context. you know, My God, it feels like the tax code really is leaning towards benefiting real estate investors because then I started to learn about concepts like depreciation. And now under this administration, you know, there are things you can do and get 100% depreciation upfront on certain things. Concepts, I just did one a month ago, a 1031 exchange where We had a large liquidity event from an underlying property and then I flipped that into another property to defer those taxes and there are even rules. If you do that and you go into an opportunity zone and you hold for long enough, you might also end up not paying taxes. It's just diving into those kinds of things. Now I was fortunate the nature of my job, because a lot of what we do is adjacent to real estate, that I made sure to structure my comp to be able to participate in the real estate. so obviously at this point, it's a phrase that everybody says, equity is so serious just because... It might be equity. lot of times they can attach to tax advantages, whether that's capital gains or taking advantage of depreciation or the ability to 1031. But it really is critical. mean, cash is great, but that equity and that upside, you can really do some interesting things, particularly if you structure it. So I was also very intentional coming here about how to structure my comp. make sure I'm getting equity participation, making sure I'm getting, being able to participate in depreciation and all of those things. And again, also laying down that foundational tax knowledge of, there's ordinary income, there's, and then there's passive income, there's active income, there's passive losses, there's active income or active losses. And that you have to match those buckets. so even doing things like, of course, not everything goes right. Sometimes you get in something and there are losses, but if you fundamentally understand that, you might be able to use those losses to your advantage and dramatically cut your tax bill if you're thinking about it. So long-winded way of saying, particularly real estate, particularly venture, public markets is a little more straightforward, right? It's, know, if you, if you hold for long- term over a year, you know, tax, tax goes down, but, really understanding that at a fundamental level and letting that guide how you think about allocation and how you think about diversifying the portfolio. Very meaty, very, very, lot, a lot of meat in there. And last time we talked, you mentioned that you had gotten your real estate broker license. And I think what you're introducing to people is this idea that a lot of people think, I need to be a real estate investor hands on, right? And, you know, material participation in terms of like, I'm actually in the property, working in the property, cetera. What you're introducing is there can be careers and ways you can structure your career within real estate, have that material participation, which now kind of exposes you to not just equity ownership, but tax benefits that can offset your high income in a way that, you know, is a professional job in an office very similar to what someone would be working, maybe in the alternate lane more traditionally. Can you maybe share like, just for people, know, there's a lot in there to digest and I encourage people to watch the recording and kind of take notes and get a CPA and really unpack these concepts. Let's talk straight effective tax rate. What would you say in a parallel universe, Ashley, who's working at white shoe law firm, you know, X. No, no worries. You know, we've all of us before in the office at all. And actually working in a very highly structured tax optimized situation, what kind of difference are we talking about? Just so people can kind of sink their teeth into the order. Yeah, it's pretty dramatic and it varies year to year, but you know, this parallel universe where you're... earning, you know, earning a lot you are, and obviously it depends where you're living. I'm in Florida and I will be domiciled in Florida or a no state tax state for the rest of my life. I'm from Florida, so that helped, but you know, that's important too. But yeah, I mean, if you were, for example, when I was working in London and I was tax equalized to New York, so all right, I'm at my 37% federal. I'm at my exorbitant New York state, New York city, all of that. So yeah, I mean, your effective rate is anywhere from, depending on your location, 40, 50%, just gone. Versus in a tax optimized world, you might be going anywhere from some years. 5%, 10%, 15, 25 in years where you can't harvest as many losses or tax strategies. think about that for somebody who is a high earner. Let's say you're a very high earner or RSUs, whatever, at your organization. Say you're a million-dollar earner, 10% tax savings is $100,000 a year. $100,000 invested smartly is a big number over time. And then think about death by a thousand cuts, like 10 years, that's a million bucks that was deployed. And even if you're not going into venture or going up the risk curve, just the power of compounding alone, it dramatically changes your life trajectory. as you and I talked about, It's not just what you make, it's what you keep. And tax, structures, et cetera, that I'm always like, you pay yourself first, always. And it's so much in there because basically, and we always say this in the Gravy Wealth ecosystem is you have to have your ownership strategy, right? A lot of people are focusing on getting a job, working a job, right? quote unquote, good money. But as you mentioned, that 50% that's coming off the top doesn't include property tax, sales tax. When you really add up all the taxes, you're probably in that 60 plus percentile is all said and done. so how we're thinking about taxes and what we're keeping is like a critical essential thing at the beginning of our career because of all the compounding effects you mentioned. So I want us to really dive into that because I want people to understand the importance of like really being clear about the ownership strategy, this philosophy of keeping versus earning, right? And also having this ownership piece. Now, you now have this optimized. You identified venture as an opportunity for you to accelerate in a diversified way. Cause now we're talking about, you know, keeping more money so you can deploy a little bit more money, get it working for you. But there's some other principles that we need to introduce, which is this idea of diversification. And so I would love for you to talk a little bit around, you know, your general approach for how you were gonna... you know, kind of tackle getting into the space of early stage venture investing. I would even love to hear the story of your first deal, because your first deal seemed to be a hit. How you sourced it, you know, this obviously probably performed beyond your expectations, but it really opened up the door for, you know, Flucas Ventures kind of, you know, blowing up, so to speak, and becoming, I think, maybe the most active, if not one of the top two or three most active syndicates across AngelList, which probably means across the U.S. and the world. as far as the number of deals you were doing. So you had a philosophy when you came into the game and then you found one specific deal, tell us like, kind of walk us through that entry process as you kind of started to engage in early stage investing. Yeah, so, you know, I guess a note about diversification because there's obviously diversification within whatever asset class that you're in, but then there's also diversification amongst. asset classes and I realized like, you know, there's like a limit to it, right? Because we all only have so much attention and if you spread yourself too thin, you may not be good at one or two things, but we, you and I talked about this kind of like this barbell approach, right? Of things that are moving that have different tax benefits, things that are moving at different velocities, et cetera. that makes for kind of a balanced diversified portfolio. For me, getting active in venture, I was able to deploy a lot of capital now approaching five, six, seven years ago. And now that money gets to do work while I come into these other categories and then they harvest at different times. And so it all kind of comes together symbiotically. But I do want to say on diversification, I'm a believer, but you'll hear this kind of negative connotation term in venture about like pray and spray. It doesn't mean invest in every deal you see. For sure, it doesn't mean that, but what it does mean is like for me anyway, I like to play in different areas, different verticals, and even different geographies within venture. So like my venture portfolio is probably 20% outside, of the U.S. so you've got this geographic diversity. I am not a specialist in the sense of like, I only do deep tech or I only do fintech. Like, I've got companies in pretty much every sector that you can name. But for me, the sort of unification behind that is, you know, this idea of category creation. And so when I'm looking at a deal, I abstract away a little bit from what the product or a service is. It kind of becomes a widget for a second. put that to the side and I look under the hood and see like, can this be a category defining like true? rails of some industry like company. And of course you're not always going to be right. If that answer is yes. And then I also look at, what do they actually have to do to hit escape velocity? How are they distributing whatever they're distributing? If it checks those boxes, then I go back and look at the product. And frankly, like I said, now there's AI. So you can get somebody to explain the product to you like you're five, if you're not very technical back in. those days even a few years ago before I could do that. I mean, I would just ask people who I knew knew things about the space. Like I was doing biotech. I am not a scientist, but I can go to some people who are smart and be like, you know, what do you think about this as this tracks or space? What do you think about this? And put that all together. And before I knew it, I had all these different buckets, if you will. But yeah, going back to those first deals, one of the first deals I did, and I got very lucky, but the first one that comes to mind, because like I said, I did a couple and then the velocity picks up. I did a deal, Turing. And one of the reasons that I did the deal, the syndicate lead at the time, his analysis, was based on this book called Play Bigger. It has a longer title than that, but if you put that in, Play Bigger Venture Capital, you'll see it. But it was running through this idea, basically the framework I just discussed of category creation. And then that deal at the time, he was like, I forget what the exact math is now, because we're now some years removed. was like, if they only get X number and it was very low of full-time engineers on their platform. They hit a hundred million dollars of revenue. And so I didn't really fully understand what they were doing to be honest, but I'm like, okay, this is a strong team. They're actually experienced founders. They seem to have a strong set of initial investors and like, just, I just don't see how they can't. just, like, of course anything is possible, but I was just like, I just don't see how they can get there. And if that low threshold gets them to that type of number, and hundred million is a lot of times kind of the magic number, right? Because across most industries, you hit a hundred million, you're going to usually hit that unicorn status valuation. So I said, okay, cool. Put the check in at that time. was, know, seed stage. And now, you know, we fast forward and they're like a, you know, a leader in. in AI, these different things, multi-billion dollar valuation. And yeah, so that was super exciting to see that pay off. But to keep it a buck on the flip side, one of the biases that I think people have initially investing in public markets is a tendency to go for what you know. or what you think your expertise is or what feels comfortable, like some consumer companies, et cetera. And don't get me wrong, I still do some of that stuff too, but I have to say a lot of my biggest hits were so far out outside of my actual knowledge base. Like I'm not in tech, I'm not a product manager, I'm not a software engineer, but like I said, I could abstract away a little bit from that service and product and look under the hood, because I was like, What I do know is the signs that you want to see in a business or people that are really going to drive something that is universal to me, regardless of what the actual product or application is. And then I can learn enough to understand the basics of what there is they're doing. And then it's actually kind of cool because over time you actually do find yourself like the more you do this deal flow, the more you dig into it. You do actually become more literate. I'll never be an expert. but in some ways that is, I think can be an advantage because I think sometimes you can talk yourself out of deals because you think you know everything. because you think you're the expert here or this, or there's this competitor, et cetera. And in some ways, because I come in with a humility of, don't know. everything. I don't have those blinders on to make me think that I know more than I do. Very interesting. you know, in our audience, a lot of our folks are, you know, professionals, right? And so there's some similarities, right? You might be a manager or a leader of a team. You might have a subject matter expert who knows all the ins and outs of some specific thing that is necessary for your team. You're not the expert, right? But you know, the right person who has that information, and then you can see how they move and how they think about performance in their role, there's some parallels there in terms of being able to understand without actually being a subject matter expert, particularly like today's age where hardware tech and now you're getting into chips and it's almost impossible to really be a subject matter expert. And so I think from your perspective, it creates a certain level of accessibility for people when they think about, so I can apply my existing skillset, take a diversified approach, but ultimately, you know, Well, I think it boils down to, think, know, Ashley, this is where I want to go next, is this access idea, right? Because you can make that argument. If you're in the right circles, just the elevation of the caliber, the deals you see that you're even starting to really kind of opine on is half the battle right there, right? So let's talk about access for a second. And I want to actually really get really tactical here. A lot of people hear SPVs, they hear cap tables, right? They hear those and they think they understand it, but they may not know the mechanics. So if you don't mind. Just give us like a minute or two, because SPV is really the lifeblood of a syndicate. And you ran 80, $90 million of deals of capital through your syndicate, right? And now you're seeing the fruits of that labor five, six, seven years later, looking like it's going to be an okay outcome for Ashley. Maybe in our next conversation, she'll be able to poke on a yacht somewhere taking this call. just walk us through the mechanics of an SPV at a basic level for folks and kind of how this game works from a syndication standpoint. Yeah. So SPV, that's just special purpose vehicle. That's basically somebody forms a company LLC to LLC, typically Delaware LLC, and they pool capital from investors. They pool that capital. was my role pooling, syndicating that capital, taking that capital in one entity, one vehicle, and then funding it into the target investment company. so you know, right as I was getting started, particularly in 2020, 2020, 2021, like you really saw an explosion of activity. Like before, you know, there were maybe a handful of people on AngelList or just out there on their own kind of primate, private email lists who are putting together these SPVs. but you know, I think things really took off during that period. One, you had a lot of liquidity, you had a lot of kind of risk on appetite. was just kind of the perfect storm, for these SPVs. and so, you know, the danger though is like, especially when you're, when you're new to it, like in some ways, everything sounds like a great idea, right? Like, and part of the SPVs, people who are putting together the SPVs, like they're, they're marketing. to you, you know, they are not just saying, here's the company website, here's black and white, you know, the, the revenue figures, especially for early stage, because there might even not really be traction. So they are selling you the quote bull case, the best version of that. And the best version of a lot of companies, even crappy companies sounds like I'm in the next Anthropic, I'm in the next SpaceX. You are not, you are not. But. Uh, but I don't say that to be discouraging. It's just that to have some discernment because, you know, at the end of the day, as you kind of intimated with private, with private company investing with venture capital, it is completely access driven. It doesn't matter how, how smart you are. It doesn't matter if you could actually identify the next. you know, OpenAI, SpaceX, et cetera. If you are not invited to invest in that deal, that skillset is irrelevant. So you have to develop another skillset, which is, you know, discerning the deals that are high quality. And when you're starting out, that doesn't have to be as daunting as it sounds. You can kind of bowl with like the lanes up a little bit, right? And that is... On one hand, while you shouldn't solely invest based on who else is in the deal because they get things wrong all the time, including the most prestigious venture capital firms, it is usually a good sign when you're starting out to not try to be the smartest person in the room and you're the first person to put money in the check and nobody else is in because you think it's such a brilliant idea is see who else is in the deal. See if there are other investors that you respect, whether that's angel investors, whether that's prominent. venture capital funds, and then also do your homework on the person putting together SPVs. Like what does their portfolio look like? What does their, you know, in a sense, stock picking look like? You know, you want to be in deals where you're like fighting to get into the deal, not the deal where it's, you know, it's so easy to get access to. and so I think that's, that's, that's the, that's the main thing is like, sometimes I think it can satisfy an ego itch, particularly as well to also be very early. Now I love, early stage investing cause I just think it's, I think it's fun, but you know, at the same time, like don't have ego about going a little mid to later stage, especially as you're, as you're learning. Because if you are in a true. category defining investment, you will still do really well. So maybe it is a company and it's already at series A or B that you got access to. it's like, man, it's a hundred million dollar valuation. Okay. Yes. You're not going to make a thousand times, you know, your, your money most likely, but you might do pretty well for yourself and also get to learn. then as you get more comfortable, The more it's like anything, it's sports, like the more reps you do, then you get more comfort going downstream and you don't have the need to look as much for the external signal on the deal. but there's nothing wrong with looking for it to, to, start because there are a million SPVs out there. There are a million deals that sound hot and you need some kind of, you know, what some kind of signal. And like I said, that's also. The danger, particularly, I think sometimes for people who might be investing from tech is like, you're like, this exactly solves the problem that me and my team have. Okay. But what's, what's the value of, of that? that addressable market? Is that a multi-billion dollar problem or is it your, you and your team's problem? And it's just a, it's just a nice company that probably should be a private equity company and not a venture capital company. And so it's again, you know, being mindful of those blinders there. And we talked earlier before we started recording around a lot of what you say resonates so much because I think you and I, you start your journey as someone who's participating in another person's SPV, generally speaking, right? And so for anyone who's looking to kind of explore, you have to find someone who's found a company that maybe you didn't have access to, done an initial research, done a memo, giving you something that you can then go around and talk to smarter people and ask. does it sound good to you, et cetera, and doing that work, that kind of gets your introduction in the game. And so a part of it that people should understand is in exchange for that, the person who's syndicating the deal, brought the SPV to you, is getting 20% carry basically on average. a little bit more, sometimes a little bit less, depending on how hot the deal is. But basically, the incentives are generally aligned. So yes, there's an element of like, they're marketing, they're marketing, they're marketing, but they actually only get paid if... the deal exits, right? And it makes you much, they get 20% of what you would have made. And so with that being said, Ashley, I'm curious when people, know, when you, when people are getting started off and they're actually looking to assess the syndicator themselves, what would you say are the top two or three things that pay attention to? So good question. I mean, I think, I would say background, but then again, like I said, I have a very non-traditional background as well. So it doesn't just have to be that the person has been in tech, but I think, you know, if you see that they have a background that gives them interesting insights or analysis. Number two, which I kind of already hinted on is, is look at what they've already done. You know, What is their existing portfolio and how have those companies performed? Are they names that you know? If they aren't names that you know, at some point did VC firms that you know, you know, put money into it, know, Andreessen, Sequoia, Thrive, whoever else, like what ecosystem can you tell they are a part of based on how their deals have gone on to perform? And then also, you know, be a little beware. Like sometimes if you see people and like, you know, their portfolio and it's only, it's, you know, it's only the most prominent companies you can think of. Well, chances are they probably got into those via second, via sec, via secondaries and not because they are uniquely suited at picking early stage deals. But, you know, so just, just do a little digging under the hood. What round, what Were they early? Were they later stage when they invested? Are they companies that you recognize if any of them are more mature? Are top venture firms also going on and investing in those companies? That'll tell you a lot. Then like I said, now the great thing with the proliferation and democratization of information is, you can literally ask, there are articles or on a ChatGPT like, top syndicators, et cetera. And you can see their metrics and evaluate. And like I said, plug for the AngelList platform, which is how I got started, is that there were some very successful syndicators and it was basically frictionless to join those syndicates. There's no cost to it. You're only gonna pay that quote, carry, if you alluded to as if you actually decide to. invest in the deal. you know, frankly, it really is no more complicated than going into a platform like AngelList, doing a little bit of research of who runs top syndicates and requesting to join the syndicates and 90% of people will accept you. And then just as you're in that world, you'll come across information of some syndicates that are outside of AngelList and expand. Another good one that's super prolific is Gaingels as a syndicate. But between those two sources alone, you're going to see a lot of high quality deal flow just on those platforms. there are other clubs, like sometimes your alumni organization might have an investing club or your city or whatever else. And those are okay, but my honest experience is I haven't seen many that are that good. Even if it's tied to a prestigious school, a lot of times the deal flow is, is in my opinion, not that great. But like I said, between those couple of sources, that's all you really need to get started to see high quality deal flow. And if you're, if you're in it, and like I said, it does, there's a learning curve at first, but if you're in it and put in the reps, like it gets, it gets dramatically easier and it just organically expands. And I would throw in trust, right? And Ashley, I got to shout you out on this one. I remember when I was getting started, you know, kind of getting my first deals going. You are always someone who took the time and kind of gave me game, fully transparent. And I think that stands for a lot, right? Because then I remember if I had a deal I thought was interesting, I would bring it to you and say, you know, Ashley, you know, what do you think about it? And so I think there's within the world of all these folks kind of running syndicates. There's like a subset of folks that are getting a lot of the action because they built this brand, they built this trust. Okay, we're getting towards the end of this and I want to get a sense Ashley of the future, right? And so since we like, we're really, you know, kind of locking in before the AI explosion has happened, you already placed your bets. Some of your bets have benefited from the rise of AI. I'm curious, you know, as you kind of think about what's next for you and how you're thinking about opportunities in the future as someone who is... stayed with the day job, that's bringing in dough, optimize your tax rate, have a large portfolio of investments on the venture side that are going to be, hopefully seeing liquidity events on. What are you excited about from an investment perspective? What would you encourage other folks to think about right now as they're looking at allocating to the private markets? Yeah, so that's a good question. We obviously are kind of in like an AI super cycle in a sense. so I'm looking at stuff there. You do again, when you're in this kind of super cycle, you do have to be careful because some like, you know, things will just similar to how kind of crypto was frankly, a couple years ago, where like, everything's catching a bid, everything's going up and to the right. So you still need to be very discerning, but the reality is in general, from a macro perspective, and you're seeing it in the public markets as well, is like, this economy is transitioning a little bit from a financialized economy to an industrial, capex, super cycle economy. And so the things that I'm excited about play into that. for me, that's AI, but not really just the models. It's like these, these downstream and upstream things in the chain where you could do extraordinarily well investing, particularly if you discover like bottlenecks that like throttle the advancement of AI, you will make a lot of money. you and I were talking about before the recording started, I've also done a lot of like aerospace and defense. Like, the president announced he's going to ask Congress for a $1.5 trillion defense budget. Okay. I mean, that's sticky guaranteed revenue. so no, that doesn't necessarily mean go out to Lockheed Martin and these big hundred billion dollar companies, but there are all these like dynamic companies in the private space and the public space with that have had tremendous upside. So. It's looking, those are, those are probably the two categories that I'm most interested in. and that's again, just right seeing where the winds are blowing from the macro, perspective. and for me, probably no surprise based on things that I've said in, on tax and things that I've learned, you know, the, ultimate vision still looks like, for me will ultimately culminate in a family office. But you start doing those things now. You start thinking like a family office now in terms of your tax and your legal and your estate planning. so when that money comes in, then you're not scrambling, my CPA, my this, trying to get ready. I'm already ready. I'm ready. like, so. That's what I encourage people to do as well, like structure intentionally, even if it's not here yet, get your ducks in a row, get your understanding in a row. Um, because yeah, I mean, these things take time, but if you do what you need to do, like, you know, especially if you invest in, you know, I talked about category creation, but I also, I also frame it as things that are inevitable. certain things you hear being talked about, whether it's Elon Musk or Jensen Huang. like, there are just certain things that are just, they are inevitable. And investing in them, you know, obviously you to use discernment is in some ways like shooting, you know, ducks in a barrel. And if you know it's inevitable, then, you know, prepare yourself accordingly. Close us out with, you know, this idea of inevitable. And I think for a lot of folks in the audience, we feel like there's an inevitable shift from... professionals to like ownership, right? And if you think about what AI does, it in many ways is kind of removing the knowledge layer so that folks with capital can now get returns on capital without having, you know, as many at the very least, but in some cases, very few to none as far as folks have to hire to get those returns on capital. And so it feels like it's inevitable that being an owner is more important than ever, but ownership comes with financial risk, perception risk potentially. You know, and entrepreneurial risk in many cases. And that's something that you seem to have like conquered early on. You did it in your own way, right? You said, I'm going to step off the beaten path. I'm going to take some financial risks, play some bets. What would be like the philosophical kind of closing thoughts that you would offer up to people in a world where it seems like ownership is more important than ever, but you have this inevitable question of, you know, calculated risk that has to enter the equation. Yeah, so, you know, as they say, own assets or you will be left behind with inflation and where things are going in the capital markets. you almost don't have a choice. Like everything, K-shaped economy, everything is going to the asset owners. But that risk, you know, that is a big question. For me, one of the reasons that I did actually like doing venture and to some degree, real estate early on is because it allowed me to separate my emotions out of it. Like when, when you put your money into something and venture or certain things within real estate, you're locked in. if the market's doing this, that you're not marked to market every day, like there's, it just kind of is what it is. And it forces me once I hit that button to do that. Public markets are a little different, right? Cause your thing is marked to market every day and that you have to be able to control your emotions around that risk. if anything, know, venture and seeing that play out has helped me learn how to put risk in perspective. And especially now that I do more in the public markets, cause sometimes, especially in those kinds of things, you can see like. You might see what is your salary fluctuating your portfolio up or down in a day. When you, when you get to real size in your portfolio. like, I was like me X years ago, I might've been, you know, throwing up in the basket, seeing those kinds of swings. But now like, I can be very Zen about it because I can ask myself certain things like, did the thesis break? Am I directionally right? Et cetera. Then you just have to go for it. And it's just that fundamental thing of like. For me, the bigger risk and the bigger regret is not taking the swing because again, that's the benefit of structuring your life where you have, you you've got the W-2 or 1099, you know, depending on your situation, income that what if you took the absolute worst case scenario, which is losing everything worse if you were shorting things or doing leverage, don't necessarily recommend that. What is the absolute? worst case scenario and can, am I structurally reinforced to handle that? Okay, I am. And then what's the, what's the, what's the best case? And for me, that risk is, you know, it's, it's worth the risk of taking the, pursuing the best case. But like we said, being diversified, being structured accordingly and just having that time horizon. There we have it. So the audience, let's give Ashley a virtual round of applause. Thank you for always being. so transparent and willing to share kind of like your journey. And, you know, we exist because we want to have these conversations more openly because it's so important for folks to understand checking the boxes of schools and careers and the right companies is not enough to really detach from financial gravity. think Ashley, you're like a, walking case study on how to, how to approach this the right way. So with that, appreciate you as always. Again, virtual round of applause for Ashley. Appreciate you. We'll talk to you soon. All right. Thank you.