Wesley Gray is the founder and CEO of Alpha Architect, an investment platform for building custom, low-fee ETFs.
Wes is a Magna Cum Laude graduate of Economics at The Wharton School, served as a Captain in the United States Marine Corps, has an MBA and PhD in Finance from the University of Chicago. His interest in bridging the research gap between academia and industry led him to found Alpha Architect, an asset management firm dedicated to empowering investors through education. In this episode, Aaron and Wes talk about strategies to “beat the market”, how being a professor is the best gig as an entrepreneur, and his biggest advice to entrepreneurs. Wes’ Challenge: Register at https://alphaarchitect.com/mftf/ to join the March for the Fallen 28-mile ruck march Connect with Wesley Gray (Alpha Architect)
If you liked this interview, check out episode Index Funds, Bitcoins, and Telling the Truth with Mike Green.
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Aaron Watson: So you've got a, a really interesting business that we're gonna break down. Not only how you've built it and everything that's gone into it. But the, the kind of starting question. That I wanted to bring to you was really that of, you know, the folks that aren't professional investors, but need to do some investing, cuz we're all, you know, trying to save for retirement or other goals.
And there's been this, you know, huge narrative wave, I would say that there's, you know, conventionally kind of been two. Pathways by which someone would do their investing. They'd either, you know, go hire someone to be an active manager or to take a really big fee. And like, they're gonna beat the market. They're gonna do special things with that with your money, basically. Yeah. Or there's this, you know BOGO Vanguard school of thinking, which is set it and forget it, throw it in an index fund. Never return in any way, shape or form to, to analyze that. So can you talk to me a little bit just, or, or start things off with folks there's, there's a middle ground there between those two extremes. Can you just take people through how you think about that? X, Y axis. Wesley Gray: Yeah. Sure. So, so to your point, like a good baseline for any investor is just to literally avoid all the BS and focus on the cheapest, most diversified, low cost solution, which to your point is Vanguard. Right that, so that should always be someone's baseline. We have a framework called the facts where always say, Hey, make sure you focus on the facts. And what does that stand for? Well, F stands for fees. Keep them low a stands for access. I E like your liquidity, keep it high. C stands for complexity, keep it low. And then T stands for taxes which Vanguard and a lot of ETF structures will do for you. And then the S stands for search, which is like your due diligence, all your brain damage cost. You obviously wanna keep that low. So as a baseline solution, Vanguard's amazing. And then to your point on the other end is like, well, let's go pay like way over price, active managers that do all kinds of crazy things to try to beat the market. The problem with them. Is, there's not necessarily anything wrong with being an active investor, trying to beat the market and, and trying to earn higher returns than just say a passive index. The issue is if you charge too much for the value that you're potentially creating, it's a net negative. right. And so the, the kind of the happy medium is if, is if you did active investing or try to get the cost out back to investing, right? So maybe you don't wanna just own the SB 500 for the next 50 years, because we know there's all these different techniques where over long time cycles. And to the extent you can deal with the pain in anguish of the strategy, you're gonna try to engage in, it can be at the market. But you have to keep the cost down still. Right? So, so what we call that affordable alpha or affordable, active and we're a believer in that as well, but, but only for a certain segment. So either really cheap, super simple, great. Or you could do, you know, pretty cheap, really affordable and more active, also great doing really expensive, active, not [00:04:00] good. Is basically the answer Aaron Watson: makes sense. And one of the things that, and maybe this is just me. You know, not liking to follow the crowds and be in, maybe I like to believe myself to be a contrarian, but there's always been something that kind of irked me about, like, I'm just literally buying the exact same thing that every single other person is buying. And to some degree, you know, you hear, if you do what everyone else does, you're gonna get the same results as everyone else. And yes, for whatever reason, I'm a, I'm a cat that likes. Try to beat to a different drum beat. So talk a little bit about tangibly putting that into practice, what that looks like and then how that inspired the company that you've Wesley Gray: found it. Yeah. Sure. So, so again, the problem as you approach financial services is you always got to remember that people always trying to sell you something and they're very good at, on your emotions and desires. And, and one, one of the biggest emotions out there is ego. I'm not, not that it's a bad thing, but like, like you may go out there and be like, you know, I just, I can't be like everyone else. And, and that could be attributed to like, Totally fine. Total natural thing that most people do. However, if you talk to the wrong people, they're gonna identify that as a personality trait and they're gonna be like, oh, how can I exploit this? Well, I'm gonna sell them overpriced stuff. That sounds really different is really cool, unique, different, and I'm gonna win because I can charge this individual take advantage of their ego and they're gonna end up losing, but they'll, they'll feel better about it. So obviously we always wanna be really careful about avoid. That because of the, the incentives of the financial service industry. Now that said, there's nothing wrong with trying to be better than average in being different. And in fact, the only way you ever even have a hope or a prayer of beating and winning in the marketplace is obviously you have to be different, right? You can't own everything that everyone else owns and expect to outperform them because that's just silly. So we know you have to be D. To, to do well, but in a financial marketplace, you're also competing with everyone out [00:06:00] there and it's, it's a hypercompetitive game. Right. So usually in order to. Be different and do well. It requires you to do things that are typically uncomfortable. Not fun and painful, right? Because in the end you're gonna have to trade with someone in the marketplace. And so what a lot of the financial research, and again, I, I speak from just what academic research says like data driven, evidence based stuff. I'm not. Not anymore. I'm not a stock picker. I'm just a PhD quant type that just reads academic journals all day. What, what the collective academic research suggests is that if you're willing to be different, do things that are painful, maybe a little bit more risky, you have the horizon. You're not so worried about just being like the other lemmings out there. A few of the different techniques that you can tangibly put into play. Always being cognizant of obviously of cost and taxes, cuz that can ruin any. Any good idea paying too much or, or paying too much in taxes, is it boils down to a few types of strategies. One would be what they call classic value strategies. So that would be strategies that essentially buy cheap stuff. Right. So if, if your audience is not real familiar with stocks, but they know about real estate, well, instead of going by like the brand new house that they're selling out in the development, you go buy the boarded up, you know, row home in, in the middle of the ghetto. That is CEO selling really cheap that that's called value investing and, and, and the equivalent in stocks like buying securities and companies that don't look that good on paper, but they're selling really cheap. If you systematically do strategies that do that over long horizons, they generally tend to beat the market over long horizons. The other kind of class of strategy that you could do to kind of quote, unquote beat the market is what they call momentum strategies. So these are strategies where you just, you systematically buy winners. So when things are doing well, you buy them. But more, most importantly, when things are not doing well. You don't get enamored or you don't believe the story you get rid of them. [00:08:00] So momentum is another strategy that people can use at least systematic over long time horizon to quote unquote, beat the market. But it's, it's a much more trading intensive strategy than value. Like those are probably like the two main ways that are, that are simple to explain. If you have the horizon willingness to be different, keep your costs down that you can usually quote unquote, beat the market in expect. If you have like a 20 year horizon. And so Aaron Watson: basically the founding thesis for alpha architecture company, that that can be operationalized and systematized. So as to not need an active person on the button or the trigger, so to speak, and instead algorithms, computer programs you know, basically writing rules of the road and then letting that just operate on its own is scalable attainable for lots of. Wesley Gray: Yes. So, so what we do is we try to solve two things and I'll walk you through each of them. The first one is, is if you're gonna be an active manager, I, you're not just gonna buy a Vanguard fund. You need to somehow develop a process that, that intuitively and economically can beat the market over, over a long time horizon. Right? So obviously we spent a lot of time doing the research, trying to think about how to achieve this. And there's two methods you can basically. One method is you, you know, beat your head against the wall, read every 10 K report, go talk to the managers, go talk to supply channel, do like epic due diligence on a firm and try to pick the right stocks. The other thing you can do which we're I used to do that by the way. Now, now I'm what they call a systematic investor is you can just use data to identify. The securities or the stocks that on average will produce these favorable results. And it turns out, even though it may not be that intuitive, that when you compare the performance of just doing a system, for example, that buys cheap stocks or quote unquote value, invest. Those systems, which just generically go by, Hey, things that are really cheap on say like a priced earnings ratio. They tend to do just as well as the human beings that maybe spend 20 hours a day reading 10K reports trying to pick value stocks. Right. And so kind of my PhD thesis was essentially proving that to. Where I literally read a bunch of stock picks you know, that individuals were doing and I put them together and I said, well, you can actually just systematically do the same thing, ended up in the same place. So that's step one for us is how do we build algorithms and systems that can general generate a process that will presumably help win over time, but that's not what you have to do to win. Cuz now I need to be able to deliver this cheap and affordably. To the marketplace, right? Cause if I charge a lot for a process, that's good. It's not gonna be a win to the client. So we need to also make it affordable. So, so our business came about where, Hey, we believe we, we have the R and D capability. We have all the PhDs like everyone else, we can come up with the processes that will win over the long haul, but our objectives, how do we do that? Low cost. Well, we're gonna have to get rid of this notion that we're gonna drive Ferrari, go live on park avenue [00:11:00] and like do all this kind of crazy stuff. We we've got to actually live. And, and act like, like we did in the Marines, like in the Marines, they got something called do more with less, right? Like if, if we're gonna be able to deliver this cheaper to the client, you know, we've got to rip the cost out of the ecosystem. So, so we can manage these products, deliver them to the marketplace in an affordable way. And that means we just got to clean out anything that's in the way of, you know, adding costs. But no, Essentially got it. And Aaron Watson: so in terms of scaling something like this, you know, we've had plenty of software entrepreneurs on the show before, and you know, the, a AWS, Microsoft Azure, Google cloud type of solutions are one of the things that enables scaling in a way that previous eras, like they literally had to rack their own servers just to be able to put something. At scale in a, in a relatively expedient amount of time, what is, what is the confluence of technological and other just macro developments that makes, bring something like the, like this to the market possible now, like, cause a question why not 20 years ago? Why not? 10 years ago? Wesley Gray: Great. Great question. And, and I'll tell you that story cuz cuz we kinda got lucky, right? So historically the way asset management work is, well it still works like this to some extent, massive scale business, right? Cuz it's all about distribution and, and being able to pay all the lawyers and everyone to build up the compliance with head. Right? Huge barriers entry. Because how in the heck are you gonna launch a firm? Where you need a hundred sales people out there in the field to get anyone, to buy it, to get you to the scale, to be able to pay all the lawyers, to help you run this stupid thing. Right. And so that has always been a problem, but that said, and this is kind of something that's came about now or last 10, 15 years. And we just happened to start exactly this time is we started immediately with our firm with a. Empower investors for education. And one of our core beliefs is transparency. [00:13:00] So we immediately went digital marketing, right? Inbound content. We wrote content. We did research cuz I'm not, I'm not into like selling and like jamming stuff in front of grandma's face. But I really like research. I love talking about the data. I love talking about the processes. So it was just natural for us to just say, Hey, I'm not gonna do cells. I'm gonna do education. And that happened to be perfectly time when blogs, they weren't cool yet, but they were kind of getting cool. And so I start a blog, like I don't even know, like 12, 50 years ago and started writing about this stuff. And then all of a sudden people realized like, wait, internet connections are getting better. No one believes he sells people anymore. Cuz now you can Google anything. There's a lot more transparency and ability to do your own due diligence. You know, why am I listening to this idiot sales guy when I can actually just go Google and find blogs with people that got PhDs that are gonna explain to me how this works. Right. So I think the technology has, has allowed. A lot of [00:14:00] voices to be out there and in a democratic way, they kind of move to the top, but it's, you know, it's low cost for me to put out a blog and if one person wants to read it or 1 billion people wanna read it, it only costs me the time to put out the blog. And, and I think just the way that the world's moved towards getting the information from Google, from getting information from blogs, internet, and direct to consumer that that's what allowed us to scale our business without having to hire. any sales people like, like we've only starting, even though we've been doing this for 12 years now, we, I think we have like officially we have like two sales people and, and they're kind of recent onboards the last few years. It's always been organic inbound direct marketing and that, you know, that's how we got where we are. What about actually Aaron Watson: gathering the assets though? Like it's not the same as a server, but do like, I'm just so ignorant in this. Like, are there things that break when you actually just get more assets under management and maybe you hear about that with like a hedge funds. It's like, you know, we could make our trades when we had. You know, 50 or a hundred million AUM. Yeah. But when we're a 2 billion AUM firm, like we just can't even make the same trades because it doesn't yeah. You know, the opportunity isn't Wesley Gray: there. Yeah. So, that that's an easy problem to solve. And, and what I always tell people, cuz we, I deal with entrepreneurs all the time, entering our space, AUM. Literally solves all problems. Like those are all problems of too much. An AUM stands for assets to under management. So if you have a problem of having too much asset problems, like what you just talked about, well, that's a great problem to have, cause that means you probably own 10 private islands. And you have millions of dollars and millions of resources and you could solve that, right? Yeah. That's not the issue with being an asset ma manager, like a caveman could figure that out or a cave woman, cave person, I should say. But the hard problem with the asset manager is the barriers to entry to get started in the first place. Right? Cause there's one thing is when you're actually small and you don't have a lot of assets, you actually have a huge advantage in the sense that. You don't have to deal with [00:16:00] any scalability problems you can buy and sell anything without any impact. So you have that advantage. You're super nimble and you can do weird things and no one looks at you. Oddly, the problem is you have massive fixed cost and you need to get like at an, in the case of an ETF, you need to have $50 million day one, or you're lighting money on the fire. You, you know, or lighting money on fire. So how the heck do you get to 50 mil? If you're starting from zero. So you have all this ni nimble capability, but because of the huge fixed cost, you need a half 50 mil to make it profitable and stay alive by how you're gonna get 50 mil. If you don't have any money to pay for sales people to get it rolling. So, so asset manager business is just incredibly challenging because of this chicken or the egg issue. And it's the same problem with like, SASCO, Newser like if I'm gonna start like a ne a new Facebook, or if I don't like Twitter, I'm like, well, I'm just gonna go start a new. Well, the problem is they got network effects. They already got the scale. They're already there. They already paid to fix costs. No [00:17:00] problem. So even if you invent something that's better, more cheaper, more nimble, the problem is you've got to survive to get to scale, to make it profitable and worth your time. And, and that's like any good business that that's a good business. It's gonna take you a decade. Realistically to build it. And, and that's why it, I'm sure you've heard this saying, but in our business, particularly like in asset management, financial services, it's, you know, overnight success takes 10 years a and that's actually pretty good number. Like, like that's why I moved to Puerto Rico a few years ago. Because it took me 10 years to finally get to this point where I was like, I actually need to worry about taxes cuz I'm actually making money as opposed to being broke off my ass for the past decade. So it's just the nature of our, our business is challenging. Aaron Watson: So man, there's so many different directions I could go there. I'm trying to pick the, the route that makes the most sense for everyone. So the, the years of struggling the years of, you know, not needing to worry about tax optimization, cuz you're worried about growing the revenue and just getting the business to a sustainable place. Yes. Was it, was it bootstrap, like how did you [00:18:00] actually think about growing this thing? Outside of writing blogs and doing this content marketing, like what was, what was the strategy. Wesley Gray: Yep. So, so we were a hundred percent bootstrap. We've always been basically bootstrapped there there's one wrinkle on that. I'll walk you through. But essentially this is just something I always wanted to do right in the first place. Like I just, even as a little kid you know, I grew up on this on a ranch and everything. I, and I, I learned to hate manual labor at a young age and, and a long story short, I learned like, wait a second. There's this thing called investing where you just take money and you make more money. That's a lot better than like digging ditches out in the field. Right. So for whatever reason, I was like, that's what I want to do. That makes a lot more sense than like breaking my back all day long. So I, I just, I was like, you know what? I got to get into this business. Long term, it's what I wanna do. And then what my particular case is kind of cheating, right? Because what I did is I became a professor and I don't know if your audience knows about like being a tenure track professor, especially at a business school in finance, but it [00:19:00] it's a, it's what I would call a cheese ball gig. Right. You're making like a big salary. And I had a special deal where I only had to teach three classes a year. Right. So, and it was a quarter system. So there's 52 weeks in a year. A quarter's 10 weeks. So I literally worked where I had to like focus on like actually doing something for 10 weeks a year, but I had 42 weeks a year to do quote unquote research. Right. And I'm getting a huge salary. So, so in my case, it was pretty easy to be an entrepreneur because what was I doing during the 42 weeks a year? I'm thinking about investment strategies and things that I want to do. And like, cuz it'll be useful for academic research, but Hey, I might actually make some money and turn this into an investment product someday. So I had this like very lucky situation of, of not having like burn to midnight oil in one job and do the other one. So it Aaron Watson: sounds, so it sounds. So it sounds like another arbitrage. I know we're gonna talk about Puerto Rico later, but another arbitrage for anyone looking to break into investing is to just get a PhD and become a professor. Wesley Gray: yeah. Yeah, exactly. It's not easy, but, but if you, I always tell people the best gig ever to be an entrepreneur. Is to somehow become a professor be because it's not a real job. And I feel bad for, for what I call real entrepreneurs where, you know, you're literally like working your ass off 88, 9 hours a week at your day job. And then somehow you've got to figure out how to do. You're entrepreneur endeavors after that, and you got a wife and you got kids like, to me, that seems crazy. And you're just setting yourself up for failure. So you, you really need to get a situation like that, where you have something floating you, but you also have your time and or what you're doing, kind of matches what you wanna do as an entrepreneur. Anyway, cuz that's the only realistic way you're gonna be able to, to make it happen. And then the other. That I always tell people is so one, if you can become a professor, get your PhD you know, that's not, not easy, but you know, if you can do that, it is a great way to set yourself up to be an entrepreneur. The second thing is just put [00:21:00] out really great ideas and great content. And, and, and put yourself out there. And so that's what we did. And, and one way we got set up in business and, and I don't know if you ever heard this story, it's kind of crazy, but I literally had a billionaire cold call me cuz he ran my blog and he ran my dissertation as well. But like this was way back when we started our business. Right. When I was becoming a professor, I got a cold call from a billionaire. This guy named Eddie stern, who runs like the stern fan office. And he is like, Hey, you know, I got like three to $4 billion. This was around 2010 and he said, I want to get rid of all these hedge fund managers. You know, we just got smoked out in 2008. I'm tired of all this crap. We're gonna take over our money. We're gonna keep our costs down. Controller taxes. I haven't reading your blog. I like you. I trust you. Can we talk. And I was like, well, like I just VE first verified. I Googled like, is this a scam? I, I feel like I'm about to get scammed here. And I Googled and I'm like, oh crap, this is actually like a billionaires calling me. So anything, one, one thing led to another and then they basically kind of put us in business. Initially, cuz they, we got like essentially a 50 million seed into our, into our anchor strategy. . And so that was kind of about us Aaron Watson: going, just to clarify though. So, so people were stick with us. This is invested capital. So that AUM idea, not like equity that they took in the business, sometimes not equity sometimes. You know, your starting investor may take also some of the shares associated with being like, like actually the, the. The business equity itself, but this is invested capital that you can start to take your, you know, relatively small fee on and then go to the next potential investor and say, Hey, look, we already have 50 million and this reputable investor. So Hey, you should probably consider Wesley Gray: joining us as well. Yeah. Yeah. So I should clarify. It's not operating capital. It is investment capital, which is obviously way different because you know, if you have 50 million and you charge, let's say half of a percent, you know, that, that means you're getting 250 K revenue. It would be really nice if someone just put 50 [00:23:00] million in my bank account, and then I could go spin that on like operating. But, but this is really, it sounds like a lot of money, but to your point, that's the assets, but you need that because even, even if you get paid zero on. It, you know, an asset, management's something where, when you talk to people, they're like, well, how much assets do you have under management? And if you tell them that you have, well, I have a hundred thousand dollars from my mom. They're gonna be like, okay, maybe I'll give you $5,000. Right. Cause they don't wanna be like a big part of your business. But if you say, oh, I got 50 million in my business, in my assets, then they'll say, oh, I'll give you five. Right. So scale begets scale. It's like a lot of these things, you, you need scale to get the scale and it's no different in asset management, but, but the, the main point to, to go back to your original question is one, get a gig that facilitates a lot of time on your hands, and then two put yourself out there as authentically and loudly as you possibly can. And if you're saying something different unique, I truly do believe in this day and age, you know, you'll, you'll have people that reach out to you. To, to inquire about, you know, what you're doing, what's your value add and all that good Aaron Watson: stuff. And so, yeah, that's a perfect thing to build off of, which is people are gonna have these different takes and you, you reference momentum. That's also called trend following sometimes. And Value investing. Like there's still different takes within that, you know, very large universe of investing frameworks. And so if I have a particular type of momentum investing or any type of investing that I wanna do, what your platform actually allows folks to do is make their own. Custom ETF and be that the rules or the, the, the industry or the segment that you wanna focus on, you basically provide the underlying infrastructure for them to kind of express that investment thesis and, and bring it to the market in not the high fee active management way, but in a lower fee way. Do you wanna expand on Wesley Gray: that a little bit? Yes. Yeah, yeah, yeah. So, so, and, and I'll explain it. So, so we, we. Two kind of core businesses, right? And this goes back to the whole mantra of low cost and just running things lean. Cuz [00:25:00] we effectively had like an AWS situation, which I'll explain. So we have our asset management business, which is our branded products. So where we do the research, it's our particular ideas. That we run, we put it out to the market. I personally invest in them, et cetera, but over time, because we had to survive in this crazy, you know, huge barrier to entry entry business called asset management. We ended up building the ecosystem to support an asset manager institution on the cheap. Right. And every single point, along the way, we are not Goldman Sachs, where are some people in a garage trying to save money. And it turns out that, you know, we run our own assets, but that capability to be able to bring other people to market. Cheaply affordably and efficiently is, is, is what we call ETF architect. And that's what, we're where we do at your talk about where, where let's say you're an entrepreneur and you want to bring your idea to the marketplace, but you don't [00:26:00] wanna light millions of dollars on fire to try to figure out how to do that. Our platform it's kind like equivalent tech. It's like AWS, right? Like. Do you really wanna run your own server racks and do all this stuff? Probably not. It's a lot easier to just go hire Jeff Bezos in Amazon, cuz they already did it for their own business. Right. We kind of did the same thing. We, we, we didn't even know it. Because we weren't thinking about being in that business, but we essentially created like AWS for ETFs. Where, where if you don't wanna deal with all the back office, minutia and things that most people don't wanna waste time on, you know, we have a business where, where we do all the infrastructure behind the scenes to allow, you know, basic people to be. Sorry, like go be out rich and famous and sell their idea to the public, essentially. Yeah. Aaron Watson: And you're meanwhile, you're doing the shovels and pickaxes behind the gold rush. Wesley Gray: Yes. Yeah, exactly. That, that's why I tell people I'll sell a great shovel. That's low cost and high quality to anybody who, who wants to enter our business. Cuz the objective on, on that business particular is I want to make it easier for other entrepreneurs cuz I had to do it the hard. And then we kind of figured out how to do it, but I don't wanna, I don't wish that upon my worst enemy. So how do we lower the barrier to entry where other entrepreneurs can enter our business and make it more competitive? That that's what the objective of that platform is. Aaron Watson: Got it. So this has been fantastic west any I, I wanna. Discuss the ETF market and stuff a little bit more, but you are calling in first guess we've ever had from Puerto Rico. And in, in our, our note before actually doing the interview, you said it's the biggest arbitrage I know of on planet earth. So I don't know. Yes. I don't know. That's about as, as good a hook as I can put into any kind of premise set. Yeah, yeah, yeah. Wesley Gray: take it away from there. sure. So so like going back to fees, right? Like, like you always wanna get as much as you possibly can and pay as little, as much as possible for it. Right. And so in our investment business, people are gonna haggle well, you're charging me 1%. This person's charging me like. One 10th of a percent or whatever it is. Right. But people always forget that the biggest cost on your human capital or your actual capital is not the fees. It's the taxes. Right? Cause like, think about your own human capital. If you're, if you're making a lot of money, your marginal cost to the government is in many cases gonna be half of. Goes to uncle Sam. So why are we arguing about like 10 basis points or 1% we're talking about 50 percentage points every year goes to this, this thing called the us government. Right. And in SIM similar, like on your capital, like in the form of capital gains and what have you, maybe it's not 50. But it's, you know, a good 25, 30%. And so the Puerto Rico situation, and this is something I started thinking about pretty hard, cuz you know, like I mentioned, like I, I was the 10, 10 year overnight success where, where I'm basically eating ramen noodles and like taking massive, huge risk with my life. Like pissed it off my [00:29:00] wife and family and everything. And then we finally make it where I'm like, holy cow. Like, this is actually what these entrepreneurs, you get, you get rich, we'll call it like, but wait a second. Now I got to give half of this back to the government. Like I finally made it. If that's the deal, that's a bad deal. I got to solve for this. Right. And so Puerto Rico has this thing called act 60. We're we're essentially the, the country we'll call it even though it's not a country, it's party, United States, it's a colony, but you can just treat it like a country cuz they get to kind of run their own rules. They basically have a situation where, where a lot of people have been leaving the island for a long time cuz like hurricanes and some other stuff. And so they're trying to incentivize people. To bring their human capital and bringing their talents down here and to make a long story short, it's called act 60 used to be called act 2022, but effectively. And it's more complicated than this, but you pay 0% on your capital gains and you basically pay 4%. Income tax, right? There are, there are frictional costs. It's not that simple, but, but at a high level, it's [00:30:00] pretty close to that, right? So the reason I call it, the biggest arbitrage in the world is you might move from a, a marginal 50% tax income tax rate down to four. Which is, you know, life changing difference. If you compound that over time, it it's, you know, it, it, I value my time. And so if you have some set like financial goal, you know, by ripping that much out, you're gonna cut your time needed to work by like a third. Or like more like 70%, sorry. Because you're just gonna get wealthier much quicker if you should have, and Aaron Watson: it compounds, right? Like that's investing 1 0 1. Yes. It's not just 50% one. And you get Wesley Gray: a compound compounding effect. Yeah. So, so you save it and then you compound it at zero. So, so you're, if you just do any sort of spreadsheet modeling, let's say you have objective to hit X million in, in 20 years. We'll plug in the taxes. It'll take you 20 years. Come down to Puerto Rico. It might take you five. Right? And so, and if you don't want to be a work and stiff your whole. And you could hit a certain financial objective, you know, in five years versus 20, I just literally bought 15 years of my life where I could do whatever the hell I want to me. That's hugely valuable. Cause I value my time. Cause it's the only scarce resource that we all have. But of course then you got to ask. Okay, well, well that sounds amazing. And that would be an arbitrage if there's no cost, but you know, do I got to go live in Afghanistan or something or go, go live in Iraq, which I've actually been there. You know, that sucks. And a lot of people think like, oh, well I got to go to Puerto Rico. Like, like aren't I gonna get like mugged and murdered every day and it must be terrible. And, and honestly, I think it's amazing. Like I have a place called PMA Delmar, like it's tropical weather. So it's like perfect weather every day. Do we have hurricanes? Of course. Is it, is it, you know, issues? Of course, there's a huge community down here where I live in particular where it's everyone down here is like an entrepreneur. They got wife, kids. There's a. Sorry, community like security wise. I don't even worry about it. Like it's like anywhere, like, well, yeah, if you go out to the [00:32:00] city at two o'clock in your rolls Royce and you're throwing a hundred dollars bills around in the wrong neighborhood, you might get bugged, but that's not unique to Puerto Rico. That's just. The world, like that's common sense, but I actually find like Puerto Ricans to be incredibly considerate friendly and open, especially if you're willing to like put in time, like learn some Spanish, learn the culture. So I just see it as almost like, like there's not any cost, like you're gonna pay basically us. Government's gonna pay me to go live in a tropical island, hang out with really cool people every day. Like it, that's why I say it's the biggest arbitrage of all. Because you get all these benefits. And at least from my perspective, there's very little cost. If anything, it's negative cost. So I like it. Aaron Watson: So, and, and one of the other benefits is that it's also like east coast time zone, like you and I are literally like, we've setting this up, we're on the exact same time zone. It's not as if I'm going to the other side of the globe and like asleep when other people are awake and trying to coordinate that or stay up all night. Yeah, but I wanna just, I wanna ask about the costs just, just to [00:33:00] make sure. That, like you said, like, and I'm not accusing you of doing this, but like the financial advisor would be like, it's, there's no cost. There's no downside whatsoever. That's always like the alarm flag going off, so, oh yeah, yeah, yeah, sure. There, there is some infrastructure stuff and there is some hurricane stuff. Is that the, would that, would you call that like the two big costs associated with it? I would say. Wesley Gray: Yeah. So, so there's upfront frictional costs to set it up, right? Cause you got to hire some lawyers, accountants, and that can range the pen complexity situation from like 10 grand to a hundred grand or more But, but that's not really, if you're bringing any sort of scale down here where like, obviously you're, you're at a marginal rate of 50, this is Trump change, right? That the real cost honestly is the, is the emotional and like family cost and like the frictional cost of you've literally got to have no kidding live down here and be a bonafide resident. So, and that's costing a sense from an emotional standpoint. I, if you're in a place, you have a lot of anchors. You have a lot of roots. You, you literally, you literally, you cannot really not live in Puerto Rico and just hang [00:34:00] out down here. Like you got to literally live here. So I would say that's frankly, the biggest cost, the real cost that people got to think about. And Aaron Watson: is that like one of those things where it's like 180 days out of the year, something like that, they're like, Wesley Gray: you're verifying that. So, so what it is is, is. My strong recommendation. So on the capital gains, it depends on sourcing, right? So capital gains are sourced where you reside. So wherever your bonafide residence is, that's where all your capital gains get attributed. So that requirement means you need to be a bonafide resident and put a hundred a three days. In Puerto Rico. This is also the same role that applies to like a Florida, a California, Texas. What have you, same deal for capital gains in order to get the capital gains sourced to like a certain state, you have to put in the time income is sourced where you do the work. So for example, let's just say, you're like, oh, I'm gonna be smart. I'm gonna move from California to Florida, but I'm, I'm, I'm gonna go live in Florida for six months, a year in a day and not in California. But I do live in California. I do work from California. So capital gains are good. A hundred percent of your capital gains is gonna be subject to Florida, state taxes, none to California. However, your income, the 183 days that you're standing in Florida is gonna be subject to the zero state tax. But the other days that you're sitting in California doing work, those are gonna be subject to California, state tax, still same kind of concept in Puerto Rico. Right? If you do six months down here, You will get the 4% tax rate on your income. If it, if it runs through like a, like a company and it's structure correctly, however, for the other days that you're in the states, like if you go live in New York and you work the other six months up there, those six months, you're just subject to good old fashioned. taxes you were paying beforehand. Be, be again, because the sourcing on different types of income are different just based on the tax rules. So I always tell people, if you want to get the real deal, you really need to be down here like 80, [00:36:00] 90% of your days. And, and just live here as like a full-time resident. Got it. That's what I Aaron Watson: do. Got it. Well, this has been incredibly educational west before we aim towards wrapping up and last asking our standard last questions. Was there anything else you were hoping to share today that I didn't give you a chance to? Wesley Gray: No. I, I would say I, if we're talking entrepreneurs out there, my, my biggest advice on that, cuz cuz a lot of people ask. Is is you just got to keep your internal operating costs down and you just gotta be willing to grind realistically for like five to 10 years on nothing. And, and if you don't have that capability, it's why would you do it? Like, what's the point, it's just, it's too risky and too crazy. So any entrepreneur out there who, who wants to do this? It it's like anything in life. It's not a free lunch. And that includes being entrepreneur and it's not for every. Aaron Watson: Totally. And, and I've talked with so many different entrepreneurs about this, and it sounds like you're kind of over that threshold where things are starting to really compound an exciting way because you're past the 10 years. Yeah. [00:37:00] But it, it's not just that, you know, the revenue of the business compounds or that the number of clients compounds it's that your skill and your capabilities. As an entrepreneur compound as well. And I'm, you know, my business is approaching five years, so I'm halfway to that overnight success story, but I'm like realizing things now that it's, it's painful. I'm like, man, if I could have just figured this out, like two years ago, holy hell, there'd be a completely different place. And I know that there's 18 more of those waiting for me here over the next couple years that I just have to try to accelerate my, my rate to getting to. But that's, that is exactly, you know, what I've experienced and is affirming to hear from you is that, that compounding isn't just for investors, it's for entrepreneurs Wesley Gray: as well. Yes. And, and the 90% stat or whatever it is about like 90% of businesses fail it, it's kind of like a PhD, right? They always say like, if you get a PhD, it it's 1% brains, 99% perspiration. And, and it's very easy to identify. Who's gonna finish PhD. Not based [00:38:00] on their IQ, but just their ability to grind and same thing with entrepreneurship. Like, I don't need to know your brains. I don't need to know anything if I have a sense for like your, your culture of discipline and ability to grind. I, you know, it's not the 90% odds that you're gonna have. You're probably odds are probably more like inverse. There's probably 90% chance you will. If, if you could do it. So I'd say if you're someone who's got that discipline, you've got that passion, and this is something you want to do. You know, even though we're talking about how hard it is, I wouldn't dissuade you cuz I think your probability of success is actually more like 90%. You're gonna win. It's the 90% stat is, is the, is the, you know, the, the, the total population of everyone who tries. And as you know, just based on how many fat people there are in America, like it's really easy to lose weight and get skinny, like eat less or work out more. But the problem is how many people can actually do that. Right? So if they entrepreneur it's really easy, like we just said, you got to be willing to work for 10 years and hate, you know, work really hard and not.[00:39:00] Get a lot of benefits and that's just a hard thing to do so that that's where those stats come from. But you should stick with it if you, if you really think you got the discipline. Yeah. And I Aaron Watson: just love the way that, you know, you approach thinking about investing and how you, you are evidence based, but you're also, you know, part of that from a statistical perspective is what are the base rates? And so I saw the same statistics when I got started and my whole thing was okay. If 90% of people fail, what percent fail. Don't work just 40 hours that work 50, 60, 70 hours. And then what percent fail if they read more than 10 books a year and what percent fail if they, you know, commit to a content publishing schedule and never break it, like, and then you start to shift the base rates in your favor, if you can play those different games, but inspiring stuff happy for you and all the success and compounding that you've already experienced. And the fact that you're getting 15 years back is certainly something that plenty of people are gonna be jealous of. If they wanna learn more about you. About alpha architect, where in the digital world, can we point people Wesley Gray: that wanna learn more best place is Twitter at alpha architect and then on LinkedIn, I'm pretty active as well. Also like slash alpha architect. So, but Twitter's the main place where, where I reside. Aaron Watson: Perfect. We're gonna link that and all the other relevant links in the show notes to this episode. So you can connect with Wes going deep there.com/podcast is the place for every episode of the show to find that, or in the app, we're probably listening to this right now, but Wes, before we let you go, I would like to give you the mic one final time to issue an actionable personal challenge to the audience. Wesley Gray: All right. So I run this event called March for the fallen. We're eight years running now, and it is a 28 mile R March, but I always tell people, Hey, everyone's got a personal summit where it's not a charity, cuz the charity is actually showing up. To this event and conducting the event in remembrance of people that obviously fell in the service, cuz there's a lot of what they call gold star families out there. And so in order to do this, it's very easy. Go to a architect.com/mf TF and sign up [00:41:00] register. We actually cover logistics and chow. You just got to pay the 40 bucks to the base. It's out in the middle of Pennsylvania, bunch of finance geeks out there that I bring lot of movers and shakers in our business. And that's something you could literally do right now. Sign up and in two months, I'll see you in the flesh should be Aaron Watson: fun. Awesome. Where is that in Pennsylvania? Cuz that's not, not too far from me. Wesley Gray: Yeah. Yeah. It's in for Indian town gap, just, just near Harrisburg. It's around like 40 minutes. It's at the national guard training. Awesome. Aaron Watson: Well, we are going to share that link, encourage people to do it. We've got Pittsburgh listeners, so hopefully, maybe we can get a, a caravan of folks coming out your way there for that. Wesley Gray: That'd be awesome. Yeah, that'd be awesome. We'd appreciate it. And so, so obviously with gold star families, beautiful, good Aaron Watson: stuff. Well, west, this has been fantastic. I've learned a lot. I'm feeling inspired. I'm gonna go, I don't know, maybe, maybe not March that many miles, but I'm gonna go go for a walk or a run or something after this. Cause I'm fired up. Thank you so much for taking the time to be on the. Wesley Gray: Yeah, appreciate you having Aaron Watson: it's been an honor.
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Ali Moiz previously founded and sold Streamlabs and Peanut Labs, for a combined enterprise value over $180 million.
Currently, Ali is the founder, CEO, and meme Dealer at Stonks, which aims to help founders save time in fundraising so they can focus on the business. Stonks is a platform for virtual Startup Demo Days. It has quickly become popular in helping startups find their angel investors with the help of event organizer. Join Aaron and Ali on this episode as they discuss how he got it up and running so quickly with over $15 million monthly investments, while avoiding lessons from past startups, and what he is doing with the wealth he had acquired from his past companies. Ali Moiz’s Challenge; Clean up your calendar, remove things that don’t need to be there and use that time for personal development. Connect with Ali Moiz
If you liked this interview, check out Naval Ravikant’s Wisdom w/ Eric Jorgenson and Billionaire Henry Schuck just IPO’d ZoomInfo during a Pandemic.
Rich, President & CEO of Innovation Works, leads one of the nation’s most active early-stage investors. In this conversation, we discuss a recent report IW authored with Ernst & Young that detailed the last decade of venture investing in the region.
Some highlights of recent activity include the $225 million acquisition of security awareness trainer Wombat Security by California-based Proofpoint and the $1 billion round of funding recently raised by self-driving car intelligence provider ArgoAI from Ford. Further, Pittsburgh tech companies have attracted over $3.5 billion in funding over the past 10 years, including $2.1 billion in the past five years. What will this mean for the future of the region? Never miss one of our best episodes by subscribing to the newsletter. Rich’s Challenge; Advocate for the startup community in your region to elected officials. Connect with Rich Website Connect with Piper Creative YouTube Website If you liked this interview, check out our dozens of interviews with Pittsburgh influencers and business leaders including entrepreneurs than Innovation Works has invested Henry Thorne, Hahna Alexander, and Ryan Green. Subscribe on iTunes | Stitcher | Overcast | PodBay
Brent Beshore invests in family-owned companies. Unlike the venture capitalists, private equity firms, and crypto traders that fill up headlines and seek an audience, Brent humbly goes to work uncovering value in the boring spaces missed by others.
Beyond his impressive financial results, he’s assembled a talented team that complements his skill set. While he’ll humbly point to luck or colleagues for credit, his diligent assessment of thousands of deals per year has left him with a unique perspective on investing, entrepreneurship, and business. His companies have recruited doctors for the U.S. military, provided online public relations to some of the world's largest organizations, manufactured cutting-edge home solutions, created software products for small businesses, curated the latest in women's fashion on the internet, and even helped make a couple of blockbuster movies. I’m sure you’ll learn something from listening in to this interview. Brent’s Challenge; Diversify the geographic location of the people you associate with. If you live in a metro, more people from the middle of the country and vice versa. Connect with Brent Website If you liked this interview, check out episode 55 with Morgan Housel where we discuss cognitive biases and writing effectively. Here are the best finance-related and blockchain podcasts I’ve done.
I would have never gotten Brent to come on my show if I had not first heard his excellent interviews on Patrick O'Shaughnessy's Invest Like the Best. Check out all three episodes;
Ep.10 Ep. 22 Ep. 30
Underwritten by Piper Creative
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Going Deep
Watson: Well, thank you so much for hosting me here, and thank you so much for coming to my show, Brent. Brent Beshore: I really appreciate it. Thanks for having me on. Watson: I think that the best way to make your work and your business accessible and understandable for my audience is to perhaps do a little compare and contrast between the terms private equity and venture capital. Brent Beshore: Sure. Watson: And compare those worlds to what you're doing with Adventur.es (now Permanent Equity). Brent Beshore: Yeah. So, private equity and venture capital they're obviously worlds apart. They deal in both of them are private equities in the sense of you're buying small equity, stakes, or large equity stakes, depending on the situation in private companies. So sort of private equity as an overarching umbrella, certainly covers some of what we do. Well, actually, to be honest, product income is all of what we do. The term private equity though, typically comes with you, raise a fund and you deploy that fund over a period of 3 years. And then you harvest that fund over the course of say, 7 years, maybe up to 10 years and return that capital plus a return back to your investors. And so that's very different than what we do in the sense of how it's done at the size it's done. So it's very different rhythms, very different interests, very different ways of creating value. Venture capital's very, very different from what we do in the sense of, you know, venture, you're taking a minority stake in a typically high growth company that you're trying to get a multiple of your money back over a 10 year time horizon. So you're looking for a high failure rate. Small success rate, but those successes are, you know, sort of following a power-law distribution. And so what I would say is , we more closely mirror private equity in the sense of, you know, we're buying a, usually a majority stake, not always, but a majority stake in most. So the situations and. You know, we're buying them from private closely-held business owners, which, you know, private equity does the time horizon in what we do is very different and the way in which we go about it's very different. So, we like to tell people, you know, we have no intention of ever selling an investment when we make it. So if functionally, our time horizon is infinity. Now we obviously everyone's going to the same place, right? No one gets out of this life alive.So we do have to sell at some point, but we never go in with an intention of selling and we're not returning money back to investors. There's no pressure to create a return over a certain, you know, defined time horizon. So it's functionally a very different mentality, that allows us to go after things that are very different. And I can go into those details depending on how interested your audiences in the nitty-gritty, Watson: I think we’ll build on that a little bit, but I really want to build context for people about how you get into this world in the first place, but just to hone a little bit further on your philosophy. In terms of a philosophy or a mindset that would guide the investing decisions of affirm to compare with a venture capital firm like Andreessen Horowitz, they say everything is changing, so we're going to invest in these technologies or notions that are going to be the sweeping changes, versus Warren Buffet and Charlie Mongers, Berkshire Hathaway that says, well, these things really aren't changing anytime soon. So, we feel really comfortable and confident in investing in these, or perhaps a 3G, which says, these companies are bloated and we need to kind of cut some expenses and then slash and burn and improve our profitability. How would you, if you can distill it into something succinct or more broadly, explain the philosophy that you're taking to the businesses that you look to invest in a partner? Brent Beshore: That's a great question. I would say that our overarching philosophy is we want to invest in things that are enduring human need. So, if I think about the companies we're currently invested in the companies that we have sort of on the horizon, all of them are providing a function that is fulfilling a need that people have had for a really long time and we think they'll continue to have for a really long time. To give you an example, one of our portfolio companies is the nation's largest direct to consumer. Pool builder. So swimming pools, right. We're digging holes in the ground and filling them with concrete. It's a lot more complicated than that. It's gorgeous the work they do, but the functionality, what we're banking on there is, until people stop dipping their bodies in water for pleasure, we'll be okay. Watson: Yeah. Brent Beshore: What's interesting though, is comparing venture capital on Andreessen Horowitz or 3G. Everyone is functionally doing the same thing. They're trying to predict the future and they believe they can predict the future better than other people. And so they're trying to get into situations where their predictions of the future are more accurate rather than less accurate. So, Andreessen Horowitz is a good example of how they have this philosophy; they do think the world is changing at a much faster rate than most people would consider it to be changing. So, how do they create value in that? Well, they back companies that they believe are causing the change in the world, or that are going to be able to piggyback on the back of that change that they see in the world. And most of the time they're dead wrong. But, a couple of times based on the entry price they get at and the growth rate they're right and the power-law distribution kicks in. I think Andreessen Horowitz will probably generate decent returns, specifically for that firm. And so it's all just about how do you overlay your sort of overarching philosophy with being able to accurately predict the future through getting into situations that will reflect that. Watson: So, I think that where we can go, that can be really helpful for particularly a lot of the young ambitious people. Who listened to this show is getting into the nitty gritty of how one develops their own investment philosophy and what information or resources or processes you've gone through to develop your own and what is required to reach a point where you can do that with any degree of confidence? Brent Beshore: That is incredibly big. How do you learn is really the question. So I think the best learning is from experience. Hopefully, it's positive learning, not negative learning. Books can serve a great purpose. I think there's a challenging philosophy out there that you can learn everything you need to learn from books. And I think it really doesn't serve people very well. You can read about doing a deal, you can read about making an investment. Until you put your money on the line, until you've gotten the muscle memory of what it feels like until you've hit your face on the pavement a few times, it's really, really challenging to make good decisions. And so what I would say is. Getting your footing into an area. A great way to do it is read blog posts, read about every person who's in their Twitter feed if they have one. Read books about the topic, knowing that really the only thing that that book's going to do is give you a broad framework for what to watch out for, how somebody else would think through the problem, or at least how they want to present to you, how they think through the problem. I'm super skeptical now reading most people's biographies or memoirs or anything like that because I can't remember what I had for breakfast yesterday, right, or lunch yesterday. Like, I don't know. If I'm trying to go back and recount something that happened 40 years ago with any level of detail, I have no doubt that people aren't trying to lie, it's just the memory of what the important factors were and like how it all went down, I am not confident that those are very accurate. Watson: So, are you more likely then to seek out a biography that's written by someone else than an automobile? Brent Beshore: Yeah. To some degree. Although I think that it's impossible. If somebody wrote a biography of your life, it wouldn't be accurate. Watson: Yeah. Brent Beshore: Same thing for me. So, you get an approximation and everyone's trying to write a good story. Most of the time, you're eating a meal and distracted with something and crossing the street in traffic and, I mean, it's just we live fairly boring lives, right? The norm is sort of a boring mundane. And so, to only hit on the high points and to try to get those accurate, like it's without the context around a normal and ordinary life. So, if you're going to read about a Rockefeller or something like that. How did he decide to get into the oil well in Pennsylvania too, that kicked off the empire and all that? I have no doubt that maybe he was some random cousin of his wife's that he met, and they were like, “Hey, I think there's some oil lot in Pennsylvania.” And he's like, “cool, let's go out.” That's not how it's represented and maybe it's completely accurate. I just have high skepticism that what actually happens is somehow reported back with any degree of accuracy. Watson: Gotcha. So let's go back a little bit in terms of developing the philosophy or the virtues of the principles that would inform an investing decision. I do know you're influenced a lot by Buffett and Munger, but given how often they're reported on, are there other investors that you've found that you, not necessarily are trying to emulate, but have stolen ideas from or really like the way they frame some of these types of decisions? Brent Beshore: Yeah. I'll hit on the highlights that most people know. Henry Singleton Teledyne was a huge influence on the way I thought about creating value. I would say Howard Marks was another really big influence on how I think about risk and sort of probabilistic thinking, Watson: When did you start doing that? Brent Beshore: Specifically investors? I would say when I was in my late twenties. I got interested in how other people allocated resources when I had a few resources to allocate. It's really in theory before then it doesn't really matter. Before then, I was much more interested in value creation through entrepreneurship and operating a company. I spent a lot of my time doing those. Watson: Let's talk a little bit about what those entrepreneurial endeavors were if you're comfortable talking about both successes and failures associated with that. Brent Beshore: Yeah, no, I'm happy to. So the first endeavor is getting a law degree and an MBA. I had a friend with his wife, and we were out having dinner one night and she said, “I want to start a company.” It was an event marketing company. So this is in 2007, I don't know if you were in the flow back then, but back then, event marketing was sort of the avant-garde thing, creating experiences around brands. Watson: Okay. Brent Beshore: And this is pre social media. So, I said, “well, that sounds really cool.” And I was sort of desperate at that point to not be focused on school anymore. I was just burned out on the environment of learning. I wish I had a different attitude back then. If me now could go back, I would learn a lot more and I would treat people very differently. Back then I was young and dumb and arrogant, which is a dangerous combination, and thought I knew enough and was just chomping at the bit to sort of play real-life instead of play game. And so I said, “let's do it.” She said, “well, great. You'll be the business side of things.” And I still don't know what that means. It was a great lesson in how you would design a really awful business. So, a lot of the things that I've done, I basically, the framework of how I built to date is I do something, if it goes well, I figure out why it went well. And if it goes poorly, I try to figure out why I went poorly. Knowing that you can't perfectly fit the curve. Then just do more of what works and less of what doesn't. And when you sort of get into something, you see a new world open up to you. And so I got into this world event marketing. It was a subsegment of marketing. Didn't like the business for a variety of reasons: incredibly labor intensive, very locally driven, very low perceived value, just really challenging business to make work to scale, really hard, selling lumpy revenues. All the things that make for a challenging business. That led us to seeing the broader marketing space. I realized that some of the agencies we were working with through that company were getting paid a lot more to do stuff that seemed a lot more fun. Naturally we kind of said, “well, why don't we do more of that and less of this.” That led into launching an agency, which is also a very challenging business, but it's a less challenging business than event marketing. So, I got into that and I'm trying to get back to my mindset. That led into these really interesting little niches that we found. So, we hired a great guy who was a film fanatic. Very talented, had gone to film school, and we hired him to kind of come on and be the creative guy on the team. He was doing some graphic design and we're doing some video work for clients and he said, “Hey, there's this new camera technology that's coming out called red one digital cinema technology.” And it was the founder of Oakley Sunglasses dumping a boatload of money into trying to develop a film camera, a digital film camera, that looked as good as a digital SLR still camera. He did it. It cost him a ton of money and I think we were the first commercial application in the country with that technology. And all of a sudden, we started making money and making more of it and it was easier and it was a lot more fun. And so we started doing more of that and we turned into this interesting digital film studio doing high end commercials. We were able to pick up some pretty large accounts because we could come in and drop their costs dramatically. In fact, we learned huge lessons on how to price things. We lost out on a huge project because we priced it like 40% cheaper than everyone else. You know, supply and demand. You’d think that's like a great thing, right? You're going to be 40% cheaper. Why would you not go with us? Look at our quality. And they said, “we just don't believe you so we kicked you out.” We lost the account. We lost the job, which was multiple hundreds of thousands of dollars because we priced it too cheaply. And I said, “I can raise the price, you know?” And they were like, “no, we just don't believe that you can get the job done because of the price.” Even though we had a great reel and we had been shown it. Anyway, I just repeatedly learned a lot of lessons about how to bring people on to an organization, what to look for in hiring, what traits we valued over other traits, how to structure an organization, what promises you shouldn't/should make. I hit my face on the pavement over and over and over again. Watson: When you're looking at potential bids now. I don't know how often that's a part of what you're doing, but do you feel like you use that similar type of framework where you'll disqualify a company because they under-price? Brent Beshore: Oh yeah. I mean, unfortunately the way that I think almost everyone operates. I certainly do. You associate the price somebody is willing to ask for with the quality of their work. And so heck yeah, for sure. If somebody comes along, and it's a really important job- so if it's not an important job, you're gonna go to the lowest bidder- but if it was an important job, you probably don't want to go with the discount LASIK. In fact, there's a sign in Southern Missouri. I was driving there a while back and it said “discount LASIK eye surgery.” I think it was like $1,100 an eye or something like that.I was like, “oh my gosh. Does anybody actually do that?” Even though I'm sure their quality is as high as 5,000 or $10,000. I have no idea what it costs, but your vision is not something that you want to sort of get into a discount. So, I think that's sort of the mentality. When the stakes are high, quality matters and unfortunately it's really hard to compare apples to apples. Watson: Gotcha. So did the agency reach a point where it was starting to cash flow and you now had the assets to then go and invest or make capital allocation decisions? Brent Beshore: Yeah, that's a great question. So yes, the agency started early, but it started becoming successful. I mean, what’s a definition of success matter, right? It wasn't like we were rolling large, but we grew the team very fast. We brought on some really nice accounts and we started performing. It was a nice start to a business.I think it made me realize, and you can talk about the quality of business models matter, right. We did great work for some clients and they kicked us in the teeth and we did terrible work for other clients and they praised us and gave us more money. I think that that fundamental disconnect between the quality of work that we felt like we were producing and the outcome was super frustrating. That's one of the things I like least about sort of the artistic driven beauty pageant businesses, kind of a way you can describe them. Marketing definitely fits in that. Obviously the lead gen is different to some degree. It's really challenging to get yourself in a situation where clients are like no,I want a lighter shade of red for that. Right. You're like, “no. Why are we talking about this?” We're all losing money as a result of this. So, I learned a lot about just what businesses at different levels and sort of ironically, what we learned was the bigger the client, the easier they were to deal with the larger the client, certainly the more profitable they were. The larger the client, the more respectful they were. And, and this never made sense to me, right? Because I'm like, that's, that should be the opposite, right. There should be harder clients to work with, but intuitively now, if you think about it, there's a selection bias that if a company is small and stays small, there's probably a reason why they're small. And a lot of times, the reason why they're small is because the people that are at the helm of the company have some challenging personality traits and working with those people makes your life challenging or more challenging. And so that's been another hard earned lesson that I've learned over the years is to really look at the selection bias that you're getting into in every situation. But to go back and answer your question about the agency was doing well. We were having a lot of fun. It was also a lot of pain and then I had an opportunity to make my first acquisition. We sold that company today. It's called Media Cross. Wonderful team providing incredibly valuable work. They're a military recruitment firm. Their client is the United States Navy. I recruit all of the civilian Mariners that resupply the ships that never come into port. It's a really, really cool job. It's meaningful work, great team. We're lucky enough to come across it at the right time and the right circumstances that made the acquisition. That kind of opened my eyes to a whole nother world. It was sort of entrepreneurship through acquisition. I felt like as much of an entrepreneur in that world as I did starting my own company from scratch. It just was a 26 year headstart with some debt. I think at that point, anytime you get into something and it goes, “well, you think it's easy?” And I've learned that anytime I think something's easy or anybody tells me something's easy, they either got lucky or they don't know what they're talking about. I got lucky. So then I really spent a number of years kind of looking at the opportunity costs between acquisition and starting companies. Fast forward to today. And, you know, we really focus on exiting, closely held businesses, the owners of those, and really trying to help successfully transition their legacy, and prove the quality of those employees lives and improve the quality of the community. We truly try to take a sort of holistic look at everything from vendors and customers and making sure it's a win all the way around. Watson: There's a really important component to that, that we can break apart, which is what makes a company a good acquisition target? Is that they're not overly reliant upon this owner who you are buying out or who might be leaving the company and the nature of the business that you are running? So, you are not out there actually operating the recruiting business and the other folio companies. I'm curious if you can illuminate that a little bit further in terms of if there's like a hard line or a line in the sand of where you're stepping in and changing things versus this is working, let them do their thing. Brent Beshore: Yeah. So, there's a lot of different components to what you just asked. So one is, “what do we look for in a business? “I think that may lead into how we interact with the businesses. So, what we look for is a business that would be successful without us, that's sort of the baseline. So, if we need to be involved to make the business successful, It's just not a situation that's going to bear fruit for anybody. So, we look for our competitive advantage: some sort of mechanism that they've developed over time. It could be proprietary processes, it could be a patent, it could be their brand or their reputation, or their somehow entrenched in their market position. So, some people call this moat, which is really challenging. In most cases, I don't even think an owner of a company could tell you what their competitive advantage is. They're like, “I don't know. It just works. What we do, we do it right.” So, technically high returns on invested capital over a long period of time is sort of a technical definition of competitive advantage. How that plays out over time is how do they make money and how can they reinvest that money back into the business over a period of time to make more money. And so we're trying to figure that and a lot of times we can't and we deduce that the businesses really the outgrowth of the personality of the primary owner or owners and that if they left the business would implode. And I think that's what you see most of the time in smaller companies. It goes through a period of flourishing under a specific personality that built the company a specific way that works. They probably didn't intentionally build it that way, but it just sort of evolved over time. And then when you try to transition it to somebody else's ownership, it's just very rare, and very difficult. So, we try to go and find a competitive advantage so that we can either immediately separate from the ownership that is selling or over a period of time transition that competitive advantage to someone else or to some other group of people and sort of diversify itself is how we think about it. Of course, we got to get a fair price. We want to de-risk the deal in a number of different ways. But, how that leads post-close is, our motto is we want to help if we can be helpful, otherwise like let people who are the experts do their job. It would be pure insanity if somehow I decided that I would come to a swimming pool builder for instance, and tell them how to build a better swimming pool. Like these people have been doing it for 30 plus years. They're amazing at it. They built a great business. It would be pure insanity if I came in and thought I could do a better job. I think where we come in, and there's a governance aspect. So, obviously we want to make sure that things are properly counted for and information is flowing appropriately, just sort of the standard business hygiene. Occasionally we might have a good idea. Occasionally we might help question maybe a questionable idea that they might have. So really it's all working together. We're all on the same team. We're trying to work together over a very long time horizon to create an environment of success and sometimes it works better than others. It depends on the business model and the people and how everything kind of comes together. But it's very different how we think about that than traditional private equity. So, we're not coming in and saying, “okay, what can you cut? And how fast can we grow and where can we step on the gas and bring a bunch of resources?” We're typically saying “let's stabilize.” Anytime there's a transaction, there's going to be anxiety and rightfully so. We want to have people feel comfortable that we're going to treat them well. We want to stabilize the employee base. We want to stabilize the customer base. We want to develop good relationships with vendors. We want to just have the company sort of go to a new normal. And then over time, we might be making some decisions in concert with the leadership of the company. It's never, that we're forcing an opinion down. In fact, we often ask them, “what is something that we can invest in today that we wouldn't see fruit for maybe 10 years?” So, we're trying to have a very long time horizon. We're trying to help pull them out of the day to day operations and sort of make longer strategic decisions. And then everyone goes to work. Like my job is not to operate the company. And if I did that, that would screw up their job. And if they relied on me to operate, the company would screw up their life and it's sort of symbiotic. We try to treat them extremely well. I mean, how we treat the leaders of our companies is how they're going to treat their staff and how you treat your staff is how they're going to treat their customers. It's only logical to me that if you treat people well- again, we don't always nail this, we're flawed, we have plenty of shortcomings. But we try, we're really trying. We're trying to treat people fairly and consistently and be a kind voice in their life and be a thoughtful helper at times. And genuinely just try to do it together and in a way that lets them do their thing, we do our thing and sort of meet in the middle. Going Deeper Brent Beshore: If you get what you want, and it's not the thing that you actually wanted, are you going to continue to do the same thing or are you going to change what you are seeking or are after? What does that mean? Watson: Speaking to these talented leaders and letting them do what they're going to do as part of your due diligence and research process, there may be an owner that's leaving the business, but there are these existing leaders that are in place that you're entrusting. How do you think about evaluating those leaders across domains, where you might not necessarily have the expertise and skill to know or this person just has a completely unique domain specific skill set, but they are a talented leader that we want to get behind? Brent Beshore: Well, I think the nice thing about leadership is that the skills for leadership and the technical skills necessary to work within a specific space are really different. Leadership has some universal principles, at least we believe that they're universal, and so, we're really evaluating those in the leaders of the companies, as far as their technical capacity and skills. We've got to just look at the evidence. So, the evidence is they've been a part of a team that's built a very successful business in that area. If they didn't have the technical chops to do it, then the company wouldn't be successful. So, we're going to assume that they know what they're doing. And then obviously we do our research too, but that's actually not the important part. So, the important part for us is getting to know them, what motivates them, how do they think about life, what are their goals? I'm trying to triangulate what would happen if we just left them alone with no oversight. It is really what we're trying to figure out. And we're really trying to figure out, above all else, what's their integrity level. How do they think about integrity? Who are they loyal to and why? That's a bottomless, endless learning experience in and of itself. We're all incredibly complicated, messy creatures. And so, we try to get approximations based on some behavioral markers that we try to figure out early on, and then make deductions and for the most part, people who are operating larger small businesses, is how I describe it. These are successful. I mean, these are successful people in the local community. There's something about them that usually is wonderful. We get to interact with some fantastic people. They're grounded for the most part, on average, they're really thoughtful, kind, generous, well, grounded people. And it's a huge benefit. We don’t follow the companies we were involved in, we don't get the latest business trend or like these companies are not putting in, like, bring your dog to work yoga days, or the latest business guru, whatever they're saying. And these people are trying to serve their customers, trying to raise a family and they're trying to serve their communities, for the most part. And it's really wonderful and that's one of the best parts of my job is getting to interact with those types of people consistently, Watson: As you create a system and build processes that lead to larger companies, more investments, more opportunities. What comes with growing, is that you can lose potentially the things that maybe initially attracted you to the work that you're doing. So whether that is, “Hey, I love looking at deals” or “I love meeting these types of people,” are you feeling a pressure or a push that you can't do that? Or are you engineering the business and everything to just completely get to stay within that lane? Brent Beshore: That's a great question. I think I have the best job in the world. And I love it. It's not every day, it's not perfect. Most days aren't perfect, but I get to work with incredibly talented, thoughtful, kind people doing meaningful work. How I express that changes over time. And I think this is where, what's been beautiful about building Adventur.es over a period of time, I've been one participant in building it. I mean our team, maybe you thought it was joking on the way here, I feel like I'm one of the least talented people on the team at this point. As other people can step up and take responsibility for things that they can clearly do better than me. Why would I do those things, or why would I try to retain control over them? My fantasy, longterm, is that I'm completely unnecessary and worthless and they let me play around in some area of the business and put me in my corner and pat me on the head and, and tell me good luck.That would be wonderful. I truly want the organization to flourish and if I'm the weakest link, I think we're going to be okay. And that would be a wonderful thing. So I think over time, the way that I, you look at it, the way Susanne Bylund- who's the sort of my right hand person, a president of organization- she looks at the exact same ways. We’re constantly trying to find people who are better at each area and can specialize and then really focusing on how do we get the team to work together better? How do we improve communication and relationships within the company? Not doing trust falls, not doing all that stuff. I think everyone has a different style. As long as your identity doesn't rest in doing a specific thing, I think you're fine. As long as you're willing to sort of explore what that might look like Watson: In terms of building a team that would be interested in the work that you're doing here has these skill sets that are complementary and humbling for you, what have you found is the way to go about identifying and bring those people in and having them be interested in this work? Brent Beshore: I have no idea. It feels like luck.. Like literally we started talking about this all the time. Like, we feel like we are absolutely terrible at recruitment. We have incredible opportunities that are overflowing in front of us, and we don't have enough people to execute on all the opportunities, by like a factor of 10. I'd say hands down, the biggest limiting factor is finding a remarkably talented kind, generous high integrity people by far, it feels like completely random. Like I said, how we bring people on board is we somehow get in touch with them. We start a conversation. We get to know one another. We see an opportunity for them to create value on the team and to be a part of it. We invite them to do so, but that's such a long process. It doesn't feel seamless. Watson: Do you think the person that you were when you were burned out from school and just getting into the event, marketing business, was that person someone that you would have hired here? Brent Beshore: No. No, for sure. Not. I was young, obviously it's just an age number, but, I was inexperienced, I was arrogant, I was condescending, hyper competitive. No, I wouldn't have hired me. Watson: Whether it is school or it's a different form of education or training or resources, if you could inject more of that into the pool of applicants or workforce. What would you prescribe given the opportunity? Brent Beshore: Ultimately, integrity is probably the biggest one that we need. That's sort of a prerequisite for the team. Without integrity, it's so costly, so you can make it work, but it's just so costly to oversee a group of people with low integrity. I want to say low integrity means that people do things they know they shouldn't do when no one's watching. And how closely do you have to watch people? If you have to watch people closely, it just doesn't scale. And so for us, you know, we rarely come in contact with somebody that we can get comfortable with. They're not going to do things without us watching them closely. And that doesn't mean necessarily working hard or being passionate about their job or being talented. You get the impression for most people. And I think this is most people's point of view. What they believe to be true about life. This is a completely rational decision for them to make if there's a corner that can be cut, and they likely won't be found out, they're going to cut it every single time. And the problem is not cutting one corner usually, or two or three or four. It's the accumulation of a lot of people cutting a lot of corners that then has a nonlinear effect on the organization over time. And you end up developing, I guess culture debt, sort of like code debt. Everything looks okay, but it explodes over time. And you get in these really catastrophic situations where people are doing sort of consistently awful things, Gresham's law kicks in: the bad crowding out the good. People that are coworkers start seeing Bill over there. He got promoted and he constantly cuts corners. “Well, if I want to get promoted, I should cut corners too,” and then it spreads. Bad behaviors are like a virus. We're really, really focused on acknowledging that everyone's messy. I'm messy, you're messy, everyone in Adventur.es is messy. We're also focused on where the trajectory of people? Are they trying? Are we going to create a system of accountability? Where are they along that journey? How do you cultivate that? I don't know. That's part of the problem. I don't know how to cultivate. All I can do is find it. So that's why I set up, I wouldn't hire me because I don't think I fit that description when I was getting right out of college or getting out of law and MBA. I was totally willing to cut corners and, you know, had to learn over time, that's not the right way to behave. Watson: There’s a common trope or piece of advice that people say is “fake it till you make it.” And I think there's a close tie between the notion of cutting corners and faking it till you make it. I don't know if you agree with that, but do you see that as related? Because I think there's also a degree of people who would say, “Brent can say that now because he's found success and he has these winds that have a crude, and so now he can value that.” When you're just starting off, there's no other way than to scrap and to cut corners. Does that make sense? Brent Beshore: Yeah, I think they're mutually exclusive though. So if you think about what does it mean to fake it till you make it, you're basically bending reality. It's called lying, in hopes that you can bend reality long enough to get what you want. There are certainly exceptions. And I'm sure that there's a bunch of founders who are out there and could listen to this and say, “Oh no, he's completely wrong. If I hadn't lied to those 10 people, I would never have gotten this, which led me to this” or whatever. The problem at the end of the day is you built your foundation on sand, and eventually the people who you lied to figure it out and you break trust. And it's not just one lie. You're going to be lying hundreds, thousands, if not tens of thousands of times. And you create a selection bias around your life, where you attract people who will tolerate and who enjoy being around liars. Ultimately it just harms you and it harms the people around you. So, if your goal, if the ultimate purpose in life is to as quickly as you can accumulate as much resources, angling power, money, fame, whatever, the thing that you're trying to get, if your goal is to accumulate those as quickly as you possibly can, I think it is completely rational to lie, cheat and steal and run the risk of getting caught. Why wouldn't you? I think you end up going down a path that leads to a miserable life, and unfortunately the worst situation as you continue to be able to get away with it and you never achieve what you thought you would achieve. And so you're able to distract yourself from the reality in the striving. So if you listen to successful people that have made mistakes, what they'll say is “I reached the pinnacle. I reached the peak and I found out that wasn't it.” And so what you often find is a situation where it can be a very effective tactic with the wrong strategy. Watson: I take that. Maybe changing pace a little bit, we talked about the recruiting company. We talked about a couple of the companies that are in the portfolio. But you've written a blog post about this, you like these quote unquote boring companies. I don't mean that in the sense of like hat salesman, Elon Musk, but in the sense that these aren't necessarily the big, sexy brag about type of investments for most people. Brent Beshore: Sure. Watson: Can you talk about why this is where you believe the edge to be in the sense that as it almost relates like human psychology? Like you're not in the goal of chasing that game, it is about this other game. Brent Beshore: Going back to this idea of selection bias, So if you look at industries, the lowest returning industries on average. So, if you think about probabilistically, how successful will I be in an industry? The lowest success overall industries are the highest profile industries. So the wine business, the film business, marketing companies. These are all areas that it's like, “Oh, I get to be impressive. I'm in this really cool hip industry” I would argue, in totality, technology in general is a really low return business. On average right now, you have these big power laws at play, but probabilistically, if we're going to go into an area of business thinking, I just want the average success- we can talk about the psychology of why no one thinks this way- it's called the base rate. So, if the base rate is everyone loses their shirt and goes out of business, you should think long and hard about that being the industry that you choose to get into. So why is that? Why is there a correlation between we’ll call them ”sexy businesses” being lower return and “boring businesses” being higher return? Let me pose this to you. So you watch movies. When you watch a movie, do you ever have this drive where you're like, “it'd be really cool someday to create a movie.” Watson: I've experienced it. Brent Beshore: Gosh, it'd be amazing. Have you ever driven by somebody roofing a house? Watson: Yeah. Brent Beshore:Have you ever thought to yourself. “Gosh, I really wish I could quit what I'm doing today and go sit on the top of a house with no harness on and the probability of falling down is high and pound nails into the top of a roof in the hot sun. Watson: While it's 95 degrees? Yeah, no, I've not experienced that. Brent Beshore: Yeah. Most people don't. And so what you end up getting is, there are non- economic reasons why people are in an industry and there are non- economic reasons why talent is drawn to an industry. And so the higher the competition for talent and the higher the entrance into the space that is well funded, the lower the returns are going to be overall, just a supply and demand issue. Watson: There's also getting into the psychology that gets tied up in these is people who say “I don't want to be a big fish in a small pond that bruises my ego to know that I am not in Lake superior. I'm in a small lake.” Brent Beshore: Yeah. I don't frame things that way, so it's hard for me to get an insight inside somebody's head who has that mentality. What's important to me is my community and my family and my friends and my church. So, I'm not prioritizing being a bigger fish or a smaller fish. Ironically, we're all the same size regardless of the pond we're in. So you're as big of a fish as you'll be in whichever pond you're in. I do think that there is that draw. I hear a lot of young people say this, like, “I can only be successful in a New York or an LA or San Francisco,” or, you know, to lesser extent Dallas or Chicago or Atlanta. It could be true. It could not be true. It depends on what you want to do. It depends on, are you a train on a track and you've got a track laid in front of you and you're going to stay on that track? Or are you on a bicycle? Or are you hacking your way through the jungle with a machete? Those are all different frameworks for how you can think about the life you're trying to lead.Being a train on a well laid track is a very different life and a very different experience and comes with different opportunity costs then hacking your way through the jungle. Some people are happy hacking their way through the jungle, and some people are happy being the conductor of a train. Watson: That makes sense. How has your relationship with that changed? Could you say that you're not in that position right now? It's hard for you to frame into the, “what size fish am I in this pond?” or whatever. Has that been a transition for you? Has that been something that you've adopted from someone else? Has that evolved personally? Brent Beshore: Yeah. I mean, I think earlier in my life, my career, I certainly made all the mistakes. And so, I craved fame and power and money and compared myself to others. I was trying to be a bigger fish. Ultimately, thankfully, somehow I came to the conclusion that that was a pretty bad path to be on. So, I just don't know how you make that transition. I can tell you how I made it and like the steps that I took and sort of the way I thought about it at each stage. But, I don't know how prescriptive I can be to others to make that change. I think ultimately you have to figure out, if you get what you want and it's not the thing that you actually wanted, are you going to continue to do the same thing? Or are you going to change what you may be or are seeking or you're after? Over a fairly short period of time in the grand scheme of things, I mean, I'm only 34 getting ready to turn 35, I was able to somehow taste enough of the success in these different ways and realize it just felt really hollow. And the people who were around me, I looked at them and said, “oh man, you know, that life must be great. Look at their life.” Over a period of time, those people are the ones that are going to rehab and are having major psychological issues and are really unhappy. When you get people privately and you get them to open up, and you get the real raw version of their life, it's very different than the glossy Instagrammy version that most people are trained. When I was younger, I didn't know any better. I thought people who had a lot of money and had a lot of fame and power and all that like high level relationships where everyone would say that they look pretty damn happy to me. They looked like they had it all together, they looked like they were incredibly “successful” and then you get to know him and they're miserable. And the people around them are miserable. And they have more problems than “normal people” had. And after you see behind the curtain, you're like, “Oh my gosh, I don't want that.” So what, if I have a bunch of money but I hate myself and I hate my family and I hate my coworkers, where are you at that point? And to be honest, the highest correlation with misery is a high net worth. If you think about it, this is what everyone's striving towards. And the most miserable people on the planet are the thing that everyone wants. Have the thing that everyone wants. They are the person that they wish they would be, which doesn't make any sense. And that's what I'm saying is the most dangerous situation is to strive for that, but never get it and never realize that that's not the thing. Watson: Oh, so striving for the wrong thing. Like even just setting the wrong goal? Brent Beshore: Yeah. Well, winning at the wrong game isn't winning, but, at least you won at the wrong game and can realize that it's the wrong game. The most dangerous situation is you're playing the wrong game and you never win it, and you keep playing the game. And this is where you see older people who are miserable on their fourth or fifth marriage, incredibly wealthy, and they just can't figure it out. Like, I deserve to be happy, look at all the success I have, I can buy anything. Well, no. What you can buy is manipulation. And if you look at life as being, “what can you consume from everyone,” you will get a group of people around you who consume you, and it feels really crappy to be consumed. That's what it ultimately comes down to. Watson: I don't know if I have many more questions beyond that. I read the Annual Review last year. Is that the same numbers? So how many businesses did you look at in 2017- we're approaching the end of the year- what would that number be? Brent Beshore: Oh, gosh. Somewhere let's call it 2000. Actually, we're focused this year on quality over quantity. Our deal flow is at least twice as good as it was last year with having less deals, which is like the best thing in the world, because that means that we're wasting our time, less, on the deals that we shouldn't be looking at. Watson: What do you attribute that greater quality to? Brent Beshore: Just continued efforts to put out exactly what we're looking for, help educate people on things that we like versus don't like. We used to get a lot of technology, software type deals, we get very little anymore. We used to get a lot of restaurant chains and commodity oil drilling, things like that. And we just tried to really educate people on what we're really looking at. It doesn't help them or help us if they're bringing us deals that don't fit. Watson: Gotcha. Brent Beshore: It just waste’s both parties' time. We're far less focused. It's interesting. I use that as a metric to kind of,, I've looked behind the curtain of 10,000 companies. I can tell you that the overall picture is not pretty. Most businesses are some form of organized chaos and whether you want to call it the knife fight or whatever analogy you want to use, it's brutally hard. For most of those, we're just not a good fit to be in business with them. Watson: Of these companies that you've looked at, what are some of the unifying themes that are related to being successful and not just being worthy of investment? There's a lot of entrepreneurs that listen to the show, a lot of aspiring entrepreneurs, the kind of through lines between the best ones. What did those look like? Brent Beshore: Well, so it's interesting. If I was going to take a step back, even in an overview. I've never been more confident that over a long period of time in a fairly boring business, somebody can do quite well for themselves and for their families. So if you asked me “what are the odds of starting a plumbing company?” And if you don't know anything about plumbing, I assume, unless you just have a hobby in it. So, if you said to me “today, I want to go raise a family, start a career, and I just want to probabilistically do really well financially.” The area that I would point to use is I would start a plumbing company and I would first become a plumber yourself. This is probably not what your inspiring entrepreneurs are thinking in their heads right now. They're thinking about creating the next Snapchat. But probabilistically, the most successful industry, on average in the country, is the plumbing industry. We can go back to the whole nobody calls somebody in the middle of the night with poop, running down their stairs that's overflowed from the toilet and says, “gosh, you know, what I want to do is that job.” There's heavy selection bias against people entering the industry. The level of professionalism in the industry is overall low, and the need for it is enduring, the price somebody willing to pay to solve their pain is high. So, high margin, recurring and enduring business, with low professionalism. When you get those things together over a decently long period of time, if you're willing to grind on it, you're going to do really, really well. So I would say I've never been more optimistic for somebody who's going into a business like that, that over a period of time, they commit themselves to excellence in that industry, they're going to be really successful financially. Again, I'm just talking about financial success. Cause I mean, that's the sort of base mark benchmark, beyond. Interpersonal relational success of just strictly, financially. I've never been more bearish or more cynical, on getting rich fast and trying to have some success quickly. So I literally don't know. I'm sure there are businesses out there. I don't know of a business that's under five years old that is consistently generating really nice cashflow. And I've invested in a ton of different companies. I see the financial incentive for companies and the most successful and profitable businesses I see start slow and build, and they consistently build over time. There's a nonlinear relationship between time and success. And so, we have a company that we've invested in that looked like a big pile of nothing for four years, and now it's just an absolute cash machine. It's outrageously successful every single month when I get their financials, I just like it, it blows me away how much money they're making. And it looked like nothing four years in. And so I think, you know, anybody who just started a company a year ago, or two years ago was killing it. I don't know how they're killing it. And I don't know what definition of killing it means because there's no way it's long term sustainable. There's no way to assemble a team and gel a team and create a culture and develop sustainable business relationships and customers and vendors and wade through all of the stuff you have to, to create a sustainable long term business in two years. You can't even do it in five years. I mean, honestly, I feel like building most businesses is a 10 to 20 year time horizon. And so you gotta be really committed to it because one of the dangerous situations you might get into is you hopscotch around. You start something and you realize, man, that's hard. I'm going to jump to something else. Then you start that thing and you're like, that looks easy, oh, it turns out it's hard. Well, I just need to jump to the next thing that looks easy. Jump to that. Now that's hard. Guess what? Everything meaningful is hard. So what most people do, that I see pretty consistently is they face a level of adversity that makes them uncomfortable, they arbitrarily opt out and it's really that powering through that dip that I see yielding incredible results for people. I would say those are kind of the big themes. Most businesses are cyclical. Most businesses are fairly low margin, and that makes sense. If you have competition, people are going to compete away profits. In good times, you're going to be able to make more money because of the scarcity of the supply. In bad times, it's the opposite. You gotta be careful to really analyze the quality of a business not in any given year. The quality of the businesses over a long time horizon, what is the free cash flow? So not profits because profits, a lot of times, have to be reinvested back in the business. But we recently looked at a company that had 6 or 7 million dollars of “profit” and the owners could maybe take a million or $2 million out of the business, just consumed cash. And so you have to really look at the totality of the dynamics of the company, and that's really what I do for a living. I'd say that's my core competency. That's something that after over 10,000 reps, I can pretty quickly break down: what are the dynamics of the industry? How does the balance sheet income statement and cash flow statement flow together? So side note for your audience; if I could recommend one skill set to somebody who wants to succeed in business, it is to become fluent in accounting. So not being fluid in accounting and being in business is the equivalent of trying to live in China and not speak. I'm sure you can do it, I don't know how successful you can be and I don't know how many relationships you can develop, all the analogies that would make sense fit there. I would say overall that the markers of success we see are a heads down faithful attitude, where you're going to grind and try to deliver for your customers over a long time horizon, treat people fairly over a long period of time and genuinely you're going to outlast almost all of your competitors. If somebody wants to start a business today, my best advice to them, depending on what their goals are, if their goal is to get famous, becoming a plumber is not going to get you famous. So if that's what you're optimizing for, fame or, if you want power, I guess get into politics. I don't know. I think that's probably the quickest way to accumulate power. Um, it's certainly not to become a plumber. You know, if you want to generate high economic returns over a long period of time, get into a boring business and grind on it. You'll be successful. Watson: I have a good friend. He is in tech, but what he does is he just goes into buildings and installs hardware for people. That is not sexy. Brent Beshore: That is plumbing. Watson: It's its own form of plumbing. And he cannot even find people to hire. He literally has too much work coming in and not enough skilled people that he could just hire and like put them into the system that his stress point is, there's too much to do, too many jobs, too many income opportunities. And I can't take advantage of that. Brent Beshore: That’s my problem too. If you think the problem is that, it seems like he has that, we have is we're not impressive at a bar, right. So, if you tell somebody you work at Adventur.es, it's not impressive at a bar, they have no idea. “What does that mean, Adventur.es?” “Well, we're a family of companies that acquires family owned companies.” I don't know what that means. “Well, we're a private equity.” “Oh, you're a private equity firm.” “Yeah, but we really haven't. We haven't raised outside capital.” “Okay. So you're a pretend private equity firm.” I don't even know what that means. Most people have no idea what a private equity firm means. So it's really hard like that guy, I'm assuming, he goes out to a bar and people are like, what are you doing? He's like, “I'm in tech.” And they're like, “cool what do you mean you're in tech?” “Well, I plumb hardware into buildings.” Watson: I've heard him say it multiple times. Like when he'll explain it to someone and he has that awareness. He's gotten the face back enough times that he knows that no one's eyes are going to light up and he just kind of sheepishly says it despite the fact that he's just killing it. Brent Beshore: But that's what I'm saying. Mostly people want to be impressive at a bar. Almost everyone wants to be impressive at a bar, and that drives far more of behavior than our rational economic view. So, another good example of this is functionally a $40,000 a year salary in Columbia, Missouri is about equivalent to a hundred, maybe 120 ish thousand dollar a year salary in New York City. So, it all depends on your preferences and all the things that are important to you, but on average, that would be my best guess. So, if you're thinking about it that way, it literally shouldn't matter to me, if I'm pretty much pure economics, if I make 120 in New York for 40 or 35 in Columbia, Missouri, like it should be functionally exactly the same. You go try to tell that to somebody. They're going to be like, let doesn't make any sense. It's an interesting dynamic where a lot of times what people think is important to them, isn’t actually important to them. And so what they're doing is they're overlaying a set of choices onto a set of preferences that don't have any congruence at all to them. And that's where you get into this really strange anxiety and frustration and anger that life's not working out the way you want it to work out and look, luck matters a ton. We didn't talk about this but, I believe that at least 90% of any success we've had is due to luck, maybe higher, maybe 95 and even that's a proxy of luck because I was born into a country at a time period with, you know, all that stuff. But if you look at this and you say, okay, we know that people aren't honest with themselves about what they want then really, I think that comes down to the root of it is, your listeners need to really search themselves and be honest with themselves. If you just want fame and you think that's what's going to fulfill you then trying to angle for money, without putting fame as the number one thing is going to cause you a lot of pain and suffering, and you're going to have a lot of frustration. You're not going to be what you feel like on the path. Now, I would argue that all of those things are going to eventually lead you down a path of misery, but at least you're going to be playing even the bad game poorly. So yeah, at least at the end of the day, play the bad game well, and be honest with yourself about what you're trying to achieve and then just go and do it. Watson: I dig it well, even if this never made it to air and never got to share this with any of the audience, which we're obviously going to do, I have learned a tremendous amount from speaking with you, Brent. I really appreciate you taking the time as we do at the end of each episode. There's two last questions. The first is so people can follow along with what you're doing and connect in the digital world. What coordinates should we point people towards? Brent Beshore: Well, I would say that a website Adventur.es website. So our name is our website. So adventure.s with a dot before -es, go there. We have an email, like I said, it’s kind of an email in a newsletter because we just intermittently send out whenever we create a new piece of content or have something to say, we hit the list. A lot of the stuff that we've written to get perspective on how we think about the world. We're constantly changing. That's a piece that probably is the most well read piece that we've ever written called our “No Asshole Policy.” Somebody tweeted that out the other day. I hadn't looked at it in about three years and I just cringed. I started reading it and yeah. It's awful. It's really, really bad. Um, so we've just recently redrafted that will go live sometime the next couple weeks. So we're constantly trying to work and change and as we learn more, try to share that with other people. Our goal with all of our writing, all the content we create is to create a dialogue with people, attract the right people, repel the wrong people. We try to stay up to date on it and we look at it as a primary function that we have is to share learnings with the world as we learn it. Watson: The name Adventur.es, where'd that come from? Brent Beshore: We kind of talk about life being an adventure, and businesses and adventure, and it's kind of a philosophy we've always had around the office of looking at whether it's buying businesses or starting businesses or investing in businesses or operating your own businesses. Like the best analogy we have that for that it's an Adventure. And so when we went to pick a name, we picked Adventures. We had the opportunity to get the hack domain, the shortest domain that's possibly out there that fits our name. And we were like, we’ll put it in the logo. So that's how Adventur.es with the dot before the -es came about. Twitter too. I didn't mention, so yeah, Twitter, I try to engage in Twitter. It's funny, the more time I have the more engaged in Twitter, the less time I have, I don't prioritize it against everything else. Twitter is another great way to connect with me Watson: Awesome. Well, we're going to link that in the show notes for this episode, goingdeepwithaaron.com/podcast is going to be the place to find that for this and every episode of the show. But we do want to wrap up, Brent, by letting you take the mic one more time and issue an actionable personal challenge for the audience. Brent Beshore: So. I have the luxury of having a lot of friends in the Midwest, in the South, in the North, in all over the country and actually all over the world. Some of my favorite people are residents of Iceland. I consider it to be a huge blessing that I get those perspectives kind of consistently given to me. So, I have people in rural North America, in Europe and Africa that I've been able to connect with as well as people in big cities. And I would say usually most people are more dominant in either a local network, whether they're in a big city or they're rural. So, if you feel like that, you have a more rural network, go and meet people in big cities, go and get that perspective. What's life like in big cities? What's the avant garde? What's the new thing that's happening? Get that into your life. And if you're in a big city and you're listening to this and you don't know anybody who is a Republican or is religious or shops at Walmart or lives in the middle of the country, I would highly advise that you try to actively cultivate those relationships. I think what you'd find if you did that, is that people are. almost identical, but coming from very different perspectives on what's important and how they think about their life. And that's going to really greatly enrich your life and it will enrich the lives of the people who you get to connect with. I think it's an easy challenge. It's a fun challenge. Get out there and meet people who are different from you. Watson:I love that. And you've very nicely segwayed into a topic that I wanted to ask you about and just failed to because you're giving me so many other great answers in other areas. But, on the topic of cryptocurrency, you recently made a post here. I want to read it, say I get it correct, “if you think Bitcoin is meaningless or irrelevant, you need more friends in New York city in San Francisco, and if you think Bitcoin is destined to be the future of money, You need more friends in the Midwest.” Given that we, as a show, probably have a bias towards the New York, San Francisco types who are on that cutting edge, developing cryptocurrencies and talking about what they're doing there. On balance, not asking you to necessarily pour cold water on everything, but can you elaborate a little bit more on how that perspective pertains to cryptocurrency and maybe other thoughts or perspectives on it that you would be willing to share? Brent Beshore: Yeah. I'm no expert on cryptocurrency and honestly, I've been aware of Bitcoin and Satoshi and all that for a very long time.I’ve been fascinated with it for a very long time. Opportunity costs in my life, having two young girls and traveling a lot for work and being focused on what we're doing at Adventur.es. In a previous life, I would have been all over the cryptocurrency bandwagon and probably have tried to do something in this space. I don't think I'm a Luddite in that, but with that said, I struggle with the base foundations of what it's trying to achieve. And so I think that whether it's Bitcoin in particular or Litecoin, or heck there's a website, I went to the other day that was like, you know, 700 IKOS that were going on at the same time. And it was like, obviously joking, “the new coin for toilet paper.” I think there's a lot of things that don't need to be Crip-tarized or whatever you want to call it. I think there's a lot of things that could stand to really benefit from the technology. I think that, as far as a cryptocurrency goes, there's a lot of benefits to settling contracts, to allowing types of interactions that need some sort of level of decentralization. I also think the fundamentals of like a Bitcoin, the consumption of energy is something that just is mind blowing to me. I looked at something that I did, I think it's like the 62nd largest country. If you could categorize Bitcoin activity in terms of consumption of energy, it doesn't make much sense to me that a lot of the same people are the people who were like a traditional environmentalist and who are concerned about burning fossil fuels and a lot of the farms are near sources of energy, some of which are clean, some of which are not. But just in general, the idea of basically jumping through a lot of hoops to be able to produce a digital asset doesn't feel like the best solution longterm to the problem that I think it was addressing. Now, if that said maybe Bitcoin goes 10x from here, or 100x or 1,000x. Maybe everyone who got on the bandwagon are multi billionaires, that’s possible. I know somebody personally who's made well in excess of $30 million on Bitcoin. I also know somebody who accidentally lost their key to over $40 million of Bitcoin. In general, I think it's a really neat technology, I'm excited to watch it. I'm just sort of a bystander at this point. I don't own any Bitcoin, the only things I own are cash, US dollars and stakes in highly illiquid private companies. That's kinda my barbell strategy, so I try to block everything else out. I don't own any public shares, I don't follow any commodity prices or anything like that. So, I just try to simplify, because my investing life is pretty complicated, in one side of it. I think it's a really interesting space. I think there's gonna be a lot of development that comes out of it and hopefully a lot of good that comes out of it. I would caution people. It might turn out well today. It's never turned out well, when you get a flood of people into a space who are trying to get rich quick. I can't think of a single thing in the history of the world that's turned out well for the people. You're going to have outliers, you're going to people who it works out exceedingly well for, but again, the base rate, the base case that you've got to think through is: probabilistically, am I going to be successful, whatever successful means in that space, and I wouldn't feel comfortable right now saying today, go out and buy Bitcoin, and that's going to be the way that you support your family over the next 20, 30, 50 years. Watson: Yeah. When in a speculative mania, may the devil take the hindmost. Brent, once again, thank you so much for doing this. I really, really appreciate it, and for sharing your time with us today Brent Beshore: Really appreciate you having me on thank you so much. Watson: We just went deep with Brent Beshore, hope everyone out there has a fantastic day.
The world is a funny place. Every once in awhile, you run into someone cut from the same cloth as you. Whenever you find someone like that, i recommend recording a podcast together!
My guest, Li Jiang is a venture capital specialist, angel investor, and a co-owner of the San Francisco Flamethrowers. After leaving investment banking, he moved to Silicon Valley and has amassed a portfolio of angel investments and a family of entrepreneurs to support. As a student, Li founded a student storage and shipping company and grew it into Northwestern University’s largest student company. You’re gonna like this interview. Resources AngelList Syndicates Bill Campbell Attend my one-day conference January 27th in Pittsburgh. Learn more here. Li’s Challenge; Go and try to help someone without any way for them to repay you. Ask them to pay it forward. Connect with Li Medium If you liked this interview, check out previous tech interviews with Robert Scoble, Andy Rachleff, and Mark Leslie. Subscribe on iTunes | Stitcher | Overcast | PodBay
Mark Leslie was the founding Chairman and CEO of Veritas Software. During his tenure as CEO, the company went from 12 employees to 5,500 employees deployed globally, and from a revenue base of $95,000 per year to $1,500,000,000 per year. In 2000, Veritas was the 10th largest independent software company by revenue, third largest by market capitalization, and achieved the distinction of becoming a Fortune 1000 company.
From 1980 until 1990 he served as president and chief executive officer of two Silicon Valley high-tech start-up companies. His prior experience included sales management, sales executive, systems engineer, and OS programmer. Mark Leslie is a successful retired entrepreneur and continues to be active in the Silicon Valley community. Connect with Mark Resources The Sales Learning Curve by Mark Leslie & Charles A. Holloway Subscribe on iTunes | Stitcher | Overcast | PodBay 234 Aaron Klein, Managing Risk, Common Investing Mistakes & the Future of Financial Advising8/2/2017
Risk is a word with numerous definitions. Riskalyze helps investors negotiate the risks they face.
Aaron Klein is the quintessential entrepreneur, spending his entire career working with entrepreneurial businesses at the intersection of finance and technology. He’s led companies or teams working on business operations software, payments technology for political candidates and causes, and mobile strategies for trading tools. He co-founded Riskalyze in 2011 and has led the company through the building of its core technology. The company has grown to support over $2 billion in portfolios and twice been named one of The World’s Top 10 Most Innovative Companies in Finance by Fast Company Magazine. Aaron’s Challenge; Find an apprenticeship to gain experience before starting your first business. Resources Nick Murray Never miss one of our best episodes by subscribing to the newsletter. Connect with Aaron Website If you liked this interview, check out my interview with Wealthfront CEO Andy Rachleff and all of our other finance-related episodes. Subscribe on iTunes | Stitcher | Overcast | PodBay
Andy’s Challenge; Stop sitting on the sidelines and start investing in a diversified portfolio of index funds. Get an emergency fund.
Andy Rachleff is Wealthfront's co-founder, President and Chief Executive Officer. He serves as a member of the board of trustees and vice chairman of the endowment investment committee for University of Pennsylvania and as a member of the faculty at Stanford Graduate School of Business, where he teaches courses on technology entrepreneurship.
Prior to Wealthfront, Andy co-founded and was general partner of Benchmark Capital, where he was responsible for investing in a number of successful companies including Equinix, Juniper Networks, and Opsware. He also spent ten years as a general partner with Merrill, Pickard, Anderson & Eyre (MPAE). Andy earned his BS from University of Pennsylvania and his MBA from Stanford Graduate School of Business. Further Reading Innovator’s Dilemna by Clayton Christensen Innovator’s Solution by Clayton Christensen A Random Walk down Wall Street by Burton G. Malkiel Howard Marks, OakTree Capital Letters Never miss one of our best episodes by subscribing to the newsletter. Connect with Andy Rachleff
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Kevin started his career as a logistics officer for SWAT. This experience gave him insight into the criminal justice world and he soon found that training SWAT teams was the best way to reduce use of force while ensuring the national security of our country. Fulcrum Tactical was born out of that idea and within 18 months he took it from a charity to a for-profit company.
He started investing in startups on the side but focused on Fulcrum Tactical and his new venture, Fulcrum Farms, a sustainable farm producing high quality meat and eggs for families and restaurants in the Chicagoland area. After 6 years, Kevin sold Fulcrum Tactical and moved on to investing in startups full time by starting Fulcrum Investing. Kevin’s Challenge; Set aside designated time every day to plan your next step. Never miss one of our best episodes by subscribing to the newsletter. Connect with Kevin State of Logic If you liked this interview, check out our most popular episodes of all time. Going Deep with Aaron Watson is brought to you by Audible - get a FREE audiobook download and 30 day free trial at http://www.audibletrial.com/Aaron. With over 180,000 titles to choose from, you can enjoy from any mobile device. Subscribe on iTunes | Stitcher | Overcast | PodBay
Mark has been an active real estate investor since 2004, so he brought a wealth of knowledge with him when he founded Luxmana Investments in 2011. He started out as a part-time investor––holding a full-time job in high tech––and his passion for real estate enabled him to escape the rat race of Corporate America.
Prior to Luxmana, Mark succeeded in multiple development projects in the trendy Highlands and Berkeley areas of Denver, Colorado. Since then, he's acquired dozens of residential and multifamily income properties through Luxmana Investments LLC, which he founded in 2011, and Peak Margin Partners LLC, which he co-founded in 2013. Mark has successfully overseen the operations of his own assets, and that of other investors, in Colorado, Texas, Florida and Illinois. This includes his active involvement with MBP Capital and Catalyst Multifamily Management—a highly successful multifamily investment, management and brokerage firm. During this tenure, Mark has had property management oversight of his Dallas area multifamily portfolio, while assisting with acquisitions and dispositions of assets as well. Real Estate Book Recommendations Rich Dad, Poor Dad by Robert Kiyosaki Rich Dad Advisor Series Mark’s Challenge; Learning leads to taking action. Take some sort of action today. You can analyze real estate deals at BiggerPockets.com.
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Over the last quarter century Damion Lupo has started and owned more than 30 different companies including an insurance agency, a precious metals firm, a venture capital company, a financial consulting firm, and more than a dozen real estate investment and development companies. He’s also the founder of Yokido, his own martial art and holds 3 other black belts.
Damion has published 5 books and is a sought after financial consultant for accredited investors and business owners. Using a vast knowledge of financial markets, money psychology and pattern recognition he’s an expert at quickly diagnosing hidden financial cancers with clients and their organizations and rewiring both for success. Damion’s personal philosophy centers on Self Responsibility and a conviction that the only path to freedom is through candor, growth and a big vision. That big vision ideal is what drove him to found Total Control Financial in 2016 and design everything around 10X growth and 10X impact for the client, the team and the shareholders. Damion’s Challenge; Ask yourself, “What is true?” and grab Damion’s book and try out the exercise. http://www.goingdeepwithaaron.com/podcast Connect with Damion Website If you liked this interview, check out our collection of interviews with financial advisors, investors, and other financial thought leaders.
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Dinesh is a self-professed technophile, in addition to a speaker, mentor, and entrepreneur. He has taken part in three separate companies getting acquired, the third for over $200 million dollars. These days he stays busy investing, mentoring, and sharing wisdom. He initially went to university for sciences, which lead him to a career in software. It wasn’t long before he realized that his pay would hit a ceiling. He saw the sales guys driving Porsches and Jaguars—and wanted in. Little did he know that his passions were in unlocking a business' potential, which goes far beyond the sale. Dinesh’s Challenge; Count your “I can’ts over the course of one week, then work to change one to “I can”. http://www.goingdeepwithaaron.com/podcast Connect with Dinesh Website Clarity.fm If you liked this interview, check out episode 118 with Kevin Kelly where we discuss the technological trends that will shape our future.
Chris Hill is a podcast host at the Motley Fool. One of his shows, Motley Fool Money, airs every week on radio stations across America, including top-10 markets Los Angeles, San Francisco, Houston, Boston and Washington, DC. Its companion podcast is consistently ranked as one of the top business & investing shows on iTunes.
Chris joined the Motley fool in 1997 and has helped the company build out their podcast network. Chris’s Challenge; Find time to get space from busyness and social media to be alone with your thoughts. You can figure things out in the quiet of your own mind.
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Website If you liked this interview, check out episode 55 with Morgan Housel where we discuss investing philosophy and cognitive biases. |
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August 2023
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