Finding Peak w/ Ryan Hanley

This Venture Investor's Best Advice: "Sell the Wind, Not the Sailboat"

57 min
Mar 4, 20263 months ago
Listen to Episode
Summary

Venture investor Chris Van Dusen discusses his investment philosophy, emphasizing the importance of founder experience, market focus, and emotional discipline. He shares insights on AI's transformative potential across industries, the romanticization of entrepreneurship, and why "selling the wind, not the sailboat" matters for startup success.

Insights
  • Second and third-time founders outperform first-time founders because they've experienced failure, understand execution challenges, and don't need survival motivation to drive them forward
  • Founders targeting 'everyone' as their market will reach no one; successful entrepreneurs solve problems for specific endemic audiences they deeply understand
  • The compression of seed and Series A valuations means waiting for later rounds no longer guarantees significantly better returns relative to execution risk
  • AI represents the first technology wave in 20+ years capable of creating real winners and losers in traditionally protected industries like insurance
  • Emotional discipline in investing requires separating portfolio allocation (never bet money you can't afford to lose) from daily price movements and news cycles
Trends
AI disruption of regulated industries: Insurance and healthcare face unprecedented competitive pressure from AI-enabled startups bypassing legacy technological roadblocksCompression of venture funding rounds: Seed and Series A valuations are converging, reducing the traditional upside advantage of early-stage investingDopamine-driven investment culture among Gen Z: Younger investors prioritize high-frequency trading and moonshot bets over patient capital strategiesFounder experience as primary investment signal: VCs increasingly weight prior exits and battle scars over business plans and market size projectionsSpecificity as competitive moat: Founders who deeply understand narrow use cases outperform those attempting to serve broad, undefined marketsAI applications in biomechanics and longevity: Peptide research, movement mapping, and physical rehabilitation are emerging as high-impact AI use casesLifestyle business legitimacy: Profitable, founder-dependent businesses are gaining acceptance as valid exits despite lower enterprise valuationsContrarian positioning in crowded markets: When capital floods into trending sectors, opportunities exist in adjacent or opposing market segments
Topics
Venture capital investment thesis and due diligenceFounder selection and evaluation criteriaMarket positioning and target audience specificityAI applications in insurance and healthcareEntrepreneurship vs. corporate career trade-offsEmotional discipline in investingSeries A and seed round valuation compressionSecond-time founder advantagesCopywriting and value proposition communicationContrarian investing strategiesCryptocurrency and long-term portfolio allocationGenerational differences in work ethic and patienceBiomechanics and longevity technologyGLP-1 and peptide research applicationsSports technology and human potential mapping
Companies
AI.io
Portfolio company that led Series A round; acquired by Humane to build sports tech division with new product Humane S...
Humane
Large AI company that took controlling stake in AI.io to build sports tech division and launch Humane Sport
Psycho Capital
Venture capital firm where Chris Van Dusen is a senior equity partner; focuses on A-round and later stage investments
OpenAI
AI platform referenced as example of tools founders should deeply understand beyond basic prompt usage
Apple
Referenced as exemplar of selling transformation and emotion rather than features and specifications
Hyper-Eyes
Sports training technology company mentioned as example of modern athletic development tools
Therabody
Recovery and compression technology company mentioned alongside modern athletic training innovations
People
Chris Van Dusen
Venture investor and senior equity partner at Psycho Capital; discusses investment philosophy, founder evaluation, an...
Ryan Hanley
Podcast host of Finding Peak; conducts interview and shares perspectives on entrepreneurship and investing
John Garcia
Founder of Psycho Capital; Chris Van Dusen joined his firm as senior equity partner in January 2022
Gary Vaynerchuk
Entrepreneur referenced for popularizing the idea of value in being an excellent number two or three executive
Warren Buffett
Investor referenced for contrarian investing philosophy of buying when others are fearful
Jordi Vissaron
Guest on Anthony Pompliano's Bitcoin podcast; discussed high-stakes gambling culture among Gen Z investors
Anthony Pompliano
Podcast host referenced for discussing cultural investment trends among younger generations
Quotes
"Are you an inch wide and a mile deep? Or are you a mile wide and an inch deep in what you're gonna be utilizing the investment dollars for?"
Chris Van DusenEarly in episode
"When I sit down with a founder, a big red flag is, who specifically is this product solution, whatever for? And they go everyone and I go, that no one will want it."
Chris Van DusenEarly in episode
"Don't sell me the sailboat, sell me the wind."
Chris Van DusenMid-episode
"Never invest in anything you can't afford to lose."
Chris Van DusenLate in episode
"The idea of being patient, I think, is tough for this generation."
Chris Van DusenLate in episode
Full Transcript
Are you an inch wide and a mile deep? Or are you a mile wide and an inch deep in what you're gonna be utilizing the investment dollars for? When I sit down with a founder, a big red flag is, who specifically is this product solution, whatever for? And they go everyone and I go, that no one will want it. Most great entrepreneurs have some carnal knowledge and endemic audience that they are trying to solve for. One of our portfolio companies just had a huge announcement today. So I've been working on that all morning. Okay. So AI.io, we led their A round and Humane, which is the largest AI companies, backed by the public of West Phenoceratia Arabia, just came in and took the controlling stake in the company to build their sports tech division. Wow. So huge, huge news. Yeah. I'm on the board of that company. And it's a very, very big deal. You're launching Humane Sport and bringing that to market. So more of just, it's been something in the works for a while, big, big news. And yeah, not necessarily pertains to the podcast, but that is what has been on my mind to full say. Yeah, no. I get it. I get it. Wow, that's fantastic. Pretty cool, right? Yeah, super cool. Dude, the AI stuff. I mean, this is, I mean, I feel like I'm probably preaching like I'm here, but this, this, I can't, I can't get over the AI. I can't get over AI. I can't get over it. Like I'm so deep in, you know, my own, you know, I'm at one time looking at the macro and where everything is going. And at the same time, trying to learn the nuts and bolts and actually learn Claude code and all these different things. I'm not an engineer by nature because, you know, I don't, if I'm going to invest, if I'm going to help, you know, my, a lot of my work is helping, you know, leaders that are stuck with growth. It's like revenue acceleration. Sure. And, you know, I feel like you have to, you have to understand how the, the ones and zeros work too. A lot of the guys that I feel like are kind of missing the point with some of this stuff are super smart, been successful, but they, they, they haven't opened up, you know, beyond just a pro account on open AI and punch some prompts into it. You know, they're not, they're not going beyond like how it, how all these things are actually piecing together. And it just, it's moving so fast that I think anyone who even has a slight let it tendency is going to get smoked. And so I've just, I'm fascinated by how fast this shit is moving. And the interesting part is this. The industry that I kind of grew up in, which is the insurance industry, they have survived a lot of these technology waves because of regulation. And they're, it's very monopolistic. And they've created a lot of disguised technology bugs that are actually features in order to keep, you know, the industry at a certain pace. And this is the first time, at least in my 20 plus years in the industry, that I've come across anything technology or otherwise that I think is actually going to start to, to really create winners and losers. I mean, and I don't know how much time you've spent, or if you've done any investing or spent any time with any businesses in the insurance industry, but health's a little different. I mostly spend time in probably casualty, but it's mostly filled with like, like, see players. So it's very interesting space. And I guess that probably makes me a see player too, which is fine. But you don't get, like, if you're, if you're a rock star, a player, you're an engineer, you're an investment banker, you're out, you know, doing entrepreneurial shit. So you get smart, but like highly risk averse anti-ambitious people. And the business model is just so good that you can, you can literally, like, I know this is thrown out as a cliche all the time, you can literally fail your way to massive success in the insurance industry once you, once you hit a certain volume. So I'm very interested to see where AI takes the insurance industry and how many of these technological roadblocks that have personally been put in place, how quickly the right people can jump past them and really change what happens. So it's going to be really interesting. Yeah, I mean, we've talked about applications for, you know, for AI a lot internally, right? There's certainly very easy ones to look at. If you look at a marketing team and cutting down FTEs, right, from a lead generation perspective, have an agent do 80% of the pre-qual, right? Which might do something in P and C work, right? Certainly doesn't the mortgage industry, certainly doesn't, and others already, right? Our customer service for that matter. But there are some companies that are actually doing and leveraging it in a really, really meaningful way. You know, this is nothing that anyone is ambitiously doing, but you look at the VA, right? I didn't serve, but a few team members of Minus Leico did. And if you think about the process of exiting your career in the military, it usually is a lot of figuring out how disabled you are, right? And so you would think that was a really dialed in process. And watching someone go through it this year, it is not close to a refined and dialed in process. And so you look at applications, you know, AI did I know that I mentioned earlier, is mapping human potential. Well, what does that really mean? At first we look at it in sports, and they can map someone, you know, running these drills against other players and who's, you know, the best of the best. But you can see a world where it's mapping how you were and how you are, and starting to understand what disability might be. Understanding, can you ever do certain things anymore? And was that a byproduct of your time, right? Workers comp, figuring out how you really, like there's so much it can be done, even on the physical rehabilitation standpoint in medical, that that's going to be a very big game changer. You know, there's already companies where, you know, you're doing your physical therapy on a screen, and it's mapping whether or not you're doing it correctly, right? There's some really interesting things that are going to happen and come out of this, I think, change fundamentally some organizations and certainly some industries. Yeah, some of the stuff that's coming out from biomechanics is crazy. The mapping, movements, and being able to make micro adjustments to how you walk, how you stand, how you move. And, you know, you think about, I spent a lot of time thinking about aging and longevity. And, like, even simple things, like the advancements that we're seeing in peptides, and how AI's being used to find these little nuances and variants in these different peptides, and how they can attack and be very specific and, you know, repairing cartilage or improving overall, you know, water retention in certain parts of your body. And, it just is as much as I feel like there's an entire industrial complex trying to convince us that being alive right now sucks. I feel like if you can kind of swipe past that veil, it is such an absolutely, an incredible time to be alive. Yeah, I agree wholeheartedly. We have more access to more data. We have access to more ways of keeping healthy. Ultimately, that's a personal decision on what you want to do, right? What you ought to believe. But, it's a great time to be alive, right? It's a great time if you want to be active to find things to help you repair more so than we've ever had, right? I even go, you know, I'm 45, go back to when I was playing baseball, right? I played baseball in college. They didn't have Velo training. They didn't have the type of companies like Hyper-Eyes or Theribody and others with, you know, compression legs and stiff machines like they have now or even a massage gun, right, for therapeutics. But we played the same game. And so, you know, 20 years from now, it'll be the best time to be healthy because we'll have even more developments. But I couldn't agree more. The idea of utilizing peptides, doing research around them and figuring out which ones can help you improve or huge. I mean, at the end of the day, the fastest growing drug that we've seen certainly in our lifetimes, Ryan, is GLP1s, which is semaglutide. Right? So like at the end of the day, these things have been around. Now, I'm sure someone in Pharma is going to yell at me for saying that because there is certain derivative differences in the antagonist for the two and three, right? The different types of GLP1s. But at its base, it's a semaglutide which have been used for a very long time, right? And so, you know, research and understanding around them, I think are really important. But yeah, I mean, there's so much you can do to improve or maintain your health and longevity. And there ever has been. And I think it's fantastic. Yeah. Well, let's take a step back and you call yourself an accident-alange pranor. And what I think a lot of us are, we may not articulate it necessarily that way. But I'm sure. I think in getting deeper into the things that I really want to discuss and share with the audience today, let's kind of level set exactly what that means to you and kind of how you found yourself into this into the entrepreneurial world as a whole. And then we can, we can dig into what you're doing today. Yeah, absolutely. You know, like many, I graduated from college, I played baseball for the school until I got hurt. Graduate college, college degree in economics started into sales. We're for real estate investment banking firm. It was a wholesaler selling growth and income funds and mes debt products during 2007 to 2009. So for your audience who knows what was going on in real estate back then, that was a very fun time to be working on working there. I came to California at the end of 09 and the company I came out for, I like to say, restructured and restructured me out. So my nice sales job, right? The thing I was supposed to do was no more. I was in California 75 days, so I didn't have a big network. But you know, rents to ask get paid, car payments to ask to be made. Right. And so ended up starting a consulting firm, kind of leveraged that into a bigger media slash marketing company. We did a lot in coverage rate optimization and media buying for a bunch of different companies here across the country and had the opportunity to meet meet some guys. And we ended up creating what was the second largest CBD brand in the world. And we sold that in 2021, right? Second largest at the time. Also, you know, my wife and I created a liquor distillery with another couple. We co-founded it and we sold that in 2021 as well. And then sold a beauty care brand in 19 raised a couple of funds in the cannabis space and was doing some active investment. And then had the opportunity to meet John Garcia, the founder of Psycho Capital back in 2017. And enjoying the firm in January of 22 is a senior equity partner. And so it's been a great experience since then. Love what I do now. But what I set out to do with my career was being sales, if you will, not create companies. And that tipping point of having to pay your bills and that back against the wall type feeling that every entrepreneur feels is where my journey began. Do you think you need that pain to be successful? Entrepreneur porn has become so ubiquitous. And I know, I mean, you know, probably more even than I do, but so many guys and gals people have have they see the blog posts. They hear the stories. They hear you go, oh, I had a CBD brand and a liquor brand and wow, that sounds fun. And I have good ideas. And, you know, I hate my boss. You know, maybe I should get into this and fail. You know, maybe most of the time non-start, right? It's a it's maybe six months of even, you know, basic, nothing ever happens. It feels to me like you need, like you need that pressure in some way. It's like, it's like a thing you have to build so bad if you can't do anything else. Or I can't pay my bills if I don't figure out a way to make money. Like, is that pressure mandatory or can you limp into this? So, I struggle to answer it because I see both. Meaning for me, a great motivator is where am I going to be sleeping in two months, right? Certainly, unless I make some money. But I also, as part of my process when I evaluate companies as a professional now, right, who evaluates companies, does due diligence and, you know, makes investments in companies, I like second and third time founders. Now, you could say, I like second, third time founders because they felt that pain and they know what they're getting themselves into. And I would completely agree, right? Similar to myself, they have some battle scars, right? They felt what it means to get up every day. Here, no more than you hear, yes. And still have the PT Barnum-esque feelings in your heart that you need to go do this and scream it from the mountaintops and have everyone listen that you are going to change something. But if our second time founder chances are they probably had an exit. Which means they don't have the same, how do I pay my rent motivation as maybe I did at the time. But again, with that experience, they know what they're getting themselves into. I think that we, in similar to what you're saying, romanticize this idea of being an entrepreneur to the point where it's not that it looks easy. It's that it's celebrated so heavily. But if we're going to call this paid to spade, the majority of companies fail, right? And not to go too deep, but if you even look at how you get out of your company unless you're building a lifestyle business, which I think are great businesses, right? Building something that pays you cash flow that either you're the key person, right? And it won't survive without you. Or meaning it can survive, but you are the thought leader, right? That does it. Or a business that just truly has no huge enterprise value that other people want to invest and eventually buy. Unless you're doing that, the majority of companies today find a hard place. You can just look at the venture and P industry, a hard place to find a home, right? Cost capital being high, IPO market being soft. I can give you a myriad of reasons, but right? Like there are some great companies sitting at half a billion dollars in sales and positive EBITDA that have no acquisition and no acquisition candidates and are too small to go public. So if you're an early stage investor, what does that mean, right? But you had to get money somewhere traditionally to get to that size. And so my whole point in saying this is, as we keep romanticizing what it means to be an entrepreneur, I think more and more people are doing it. And that's great. More and more great and not great deal flow, right? To evaluate. But at the end of the day, it is a very, very difficult thing. And I don't know that that people fully appreciate what it means to be the janitor, the CEO and everything in between. Especially if you've spent a good portion of your career, pre that, in corporate and understood how things work in that vertical box versus not being in any box as an entrepreneur. My biggest misses as an angel investor have been corporates turned entrepreneurs. That's been my biggest misses. Super smart, successful in the corporate world in the space. A good idea. No, to your point. Have never lived a life where they need to be up at two o'clock in the morning, drinking coffee, stress to the max with, you know, because they have to push out. This, you know, bug fix or the literally the product doesn't work the next day. Like that, that level and again, I'm not advocating for 20 hour days. I don't think you need to do that. I actually, that's actually a red flag for me and I'm nearly the investor that you are. You know, my, I tend to write 25 to $50,000 checks and the companies that I invest in, a lot of them are early stage. Oftentimes I play like a mercenary executive role in those companies to a certain extent. And, but you, you have to be, you have to be willing to do that when the situation calls. And, and that's, I think one of the many things that you have to look at. But, you know, I, I think it was Gary Vaynerchuk started a popularized this idea of there is just, there is, there is no lack of respect. Hutzpah that you get from being the best number three, the best number two, right. Why not be an incredible chief marketing officer for an awesome startup, right. Because that person gets a little, maybe get a little bit of breathing room where the founder, founding team CEO, et cetera, may not. And if your lifestyle demands that because I think that's the other half of the conversation. I think a lot of people, they get frustrated with the corporate world, so they see entrepreneurship as this sexy escape, right, to owning their own destiny, which it can be, you know, it certainly can be that. But they also then wanna pick their kids up at 3 PM from school and they wanna be their coach of every team. And I am those things, I have set my life up in this, I'm 45 as well, I've set my life up in this second half of it, like this podcast is a lifestyle business, right? I make money from the podcast, I love the podcast. One of the things that I do, but no one is gonna come in and buy this show for any money because it's me, right? I mean, unless they're paying me to stay on for some reason, which wouldn't make any sense anyways and I wouldn't wanna work for anybody. So like, this is the definition of a lifestyle business. I love it, but it is. And I think we, I just think there is so much value and being the number three, the number five, and just killing it and be partying off some company. If you, if your lifestyle demands don't allow you to be what is absolutely necessary, which is at least in the beginning years, on call all the time. Couldn't agree more, couldn't agree more. You know, I look at my career and we can call it entrepreneur, right? Started the media company, did all that. But you know, CBD, I was a chief revenue officer, right? When you look at the co-founding the distillery, I was kind of CFO, COO helping, right? The visionary who came up with that idea for the distillery, right? So always that number two, three, right? Got to sit there and be part of, but not be sitting there doing, unfortunately, the things that it took from a CEO level to get things over the, over the hump, right? Being part of founding teams is great, understanding how you contribute, right? With that said though, you know, the CBD company was out of Denver. And so I left Sunday or Monday from Southern California and went to Denver till Thursday or Friday, every week for four years. So, you know, you do what it takes, right? Back to that place. And so the question, you know, when you have a family and a young kid and all that is, you know, are you willing to do the things it takes to be, to have this company be successful? And, you know, to your point, you talk to some corporates that have turned and some other people who just think it's going to be very different and say, if I only had money, this would be easier, right? And they put together big raises to live a different life and hire a bunch of people. And what you really learn is the really good, scrappy executive teams or founders, I should say, understand how to make it work without money or how to be really prudent with. And you find, again, second, third time founders know how to do that. Because they also learn the power of equity and how much they can retain if they don't, you know, build huge campuses and have ping pong tables and they just do the work that needs to get done. I used to, you know, I used to say, I like to invest or even just work with people who walk with a limb. That was like, you know, you just see it. Like you were talking, you know, just the, the battle scars of the business, you know, it's, it's, I think unfortunately, you can read all the books that you want, you can listen to all the podcasts, you can have a mentor, you can go to all the entrepreneur meetings you want. There are just certain lessons you gotta learn the hard way, I feel like. I just, I think, I think, again, feature not bug. This is the way the universe is set up. There's just certain things that God was like, yep, you just gotta learn, if this is what you want, you just gotta learn the hard way. It's like hitting a base, I play college baseball as well. Until you see a curve ball or a three-two change up on the outside corner, you could read about it all you want but until you see it, you don't know if you can hit it or not. It's just the way that it is. No, I think you're spot on, you know, in our family, we call it Matt time and, you know, that came out of the fact that I've, you know, for the last 10 years, I've been training Brazilian Jiu-Jitsu. Absolutely love it. I've got my black belt back in 24, still trained now and the reason I bring it up, the reason we call it Matt time is, you know, you learn everything, meaning like you learn through what is essentially a purple belt, how to do all the moves. Now, the difference between the purple belt and the black belt is literally just time on the mat. Doing what it takes to understand when to do those things. To your point, when that three two change ups coming, right? Or when that anticipating that curve ball and seeing it break, right? Matt time doing the work, putting yourself in the place to do the hard stuff is the thing that separates really good entrepreneurs from others that aren't going to be, right? They're willingness to stand in the pocket, we call it, right? Or be on the mat and do the work. That there's a, I'm trying to remember the quote, so apologies here, but it's something along the lines of, everyone will celebrate the success, but overlook because they would never want to do it. It took to get there or something along those lines, right? It is, in many ways, whether or not it's the entrepreneurial journey or anything you want to achieve in life at a high level, right? It takes more work, you know, a 10 year overnight success. Yeah. It's kind of, kind of how I look at it. Yeah, her mosey popularized this idea. I don't think it's his, um, it's kind of what you said. It's like they clap at the beginning and they clap at the end and in the middle, everyone's dead silent. And that's when you need it the most, you don't need it at the beginning or the end. You need it in the middle. Um, so, so when it comes to, I love this idea of Matt time, by the way, love the idea. I have, I have toyed with, uh, I have toyed with jujitsu for a while. And have not been able to mentally commit for a whole bunch of reasons, less the actual work in more just lifetime. My kids are in the 10 and 10 and 12. And, um, they're kind of in the golden years. They're fun and cool and still want to hang out with me. So I'm trying to maximize that time. Cause I know they're not too distant future. Um, I will no longer be cool. They will no longer want to hang out with me and they'll have their own lives. So I'm trying to be there for them right now. But, uh, that'll be said with this idea of Matt time, when you're, when you're doing due diligence or, or you meet a founder for the first time and you're, what are some of maybe, and you can go as tactical as you want with this. But like, what are some of the aspects of the business or them as individuals, etc, that you're looking for them to have put Matt time into? You're like, ooh, I see they spent some time there. That's a green flag. Like, what are some of those areas for you? Yeah, I mean, it depends on the type of companies, certainly technology, right? What are they coming with initially? Um, did they do the work to understand if the market wants what they have, right? It's when they'd have an idea. Uh, for us, I like investing on the A round plus, right? A B, uh, it's not that we won't do seed as a firm. But I think there's certainly more risk as you go closer to origination. Um, and I think the, the value differential between seed and A, there's still a lot of pickup from a absolute return perspective. I don't mean to jump in, but this, in the, in the second, the last like five years or so, as I've gotten more into seed and, and A round stuff with some of the companies that I work with, etc. That has been a huge eye opener for me. Is I always thought, you know, hey, you get in angel or you get in seed, you know, yes, you're taking more on more risk, but there's much more upside. And one of the things that's really open my eyes recently is that, especially seed and A, dirt, like, or maybe this is a recent trend. So if you, if you have insights on this, I'd love it. If, if feels like the upside on those two rounds is convincing. And even though you're taking more risk on and seed, you're not getting as much additional upside if you wait for an A round. Is that, is that what you're seeing? Yeah. So you're seeing bigger seeds and lower A's, right? So you're sure that there's compression happening. I would absolutely agree. Um, it also depends if you're in that code chamber of the valley or not, right? Silicon Valley. They have a more standardized and you can look at carda and a bunch of other places, standardized kind of what round values should be very focused on, you know, certain revenue metrics and others. Uh, as you get out of that echo chamber, right? Uh, cause you really just need to conform to what the VCs there are going to give you. All right. It's definitely run run by them. Um, but point being, if you, if you get out of there, you'll see some wildly different types of values. Um, you know, we did a seed round a few years ago, um, that led that deal at a much higher evaluation than you'd think a seed would be. But when you looked at the founders, if you looked at what they had, those are technology that built off the back of themselves, right? There was value to have the round being that high, but that would be very non traditional. Um, in the same vein, you'll see A's at 100 million, especially an AI and others, right? Or even seed rounds and at that high, which is still could be a great value. Um, but yeah, when you look at a return mix, depending on what you're underwriting them for, right? Whether or not it's a fund or a standalone, you know, single entity deal, um, you can still capture a great value. Even if you're paying a little bit higher because of the execution risk, um, compressing, right? So if I can compress the execution risk and skull, get a good return, then adding possibly two years and a lot more execution risk for the absolute return is a little bit tougher. Yeah. It's a little tougher. And so for us, when we do deals, you know, we typically don't have a mandate. We don't have a mandate when we do deals, we're very open and opportunistic, looking for great companies that we believe in. So that's also, I'll go through the original question on diligence, but, uh, we don't have the, has to be an AI and we have to take 5% and we have to do this and we retain money or, you know, part of our fund for continuation or, you know, follow on a, we find a great deal and we do the diligence, which is a long process for our firm. And then we're your capital partner. We're in, right? We're going to give you capital, then we're going to help you see around the corner over the horizon. And dissipate what needs are how to structure the next round like we're in and committed. That's really where so I was different. But to the diligence part from a green flag perspective, I kind of shared the, you know, second or third time founder being one. Have you done your homework around the market you're trying to attack. So let's say it's a SaaS based play, right in Vindex, horrible example, but just follow me down the rabbit hole here, right? In a lot of ways that that SaaS could be used in healthcare could be used in all these other markets. So are you an inch wide and a mile deep or are you a mile wide and an inch deep and what you're going to be utilizing the investment dollars for? Because, uh, I like making this, this, this joke, if you will, when I sit down with a founder, a big red flag is like, who specifically is this product solution? And they go, everyone and I go that no one will want it. Right. So go solve it for something you may know. Most great entrepreneurs have some carnal knowledge and endemic audience that they are trying to solve for. It used to be, you know, solve your own problem. I bet you there are other people who have that problem as well. Right. Well, that's almost an endemic audience of saying there's other people like me who need this solution. Great. Don't say don't manufacture a problem for people that you're trying to solve. Right. So really focus in on the problem that you are trying to solve or what you're trying to reinvent or rework or create a new category for. But even in creating a new category, it could work long term for everyone, but there's a specific use of people that you need to go after. And if you've not done that work to truly understand or you're too wide on your, your tam, right, your total addressable market, that's a red flag for me. And then the last piece that I take no credit for this, it was another, another person in finance who mentioned this. I think they were at benchmark. I forget the partner's name. But it was the idea of, of don't sell me the sailboat, sell me the wind. And the idea being a lot of entrepreneurs, and we used to call it back in the day in sales, sell you the speeds and feeds. They don't sell you the dream. Look at the difference between old computer companies, speeds and feeds versus Apple, who made you feel what it's like to be part of this. I think it's a really important distinction because if you don't understand the wind, right, doesn't matter what you build. You know, I've made the joke before you can build a Ferrari but raise that the roads aren't paved. There's nowhere to go. Right. So don't build me a Ferrari. Right. Show me why what you're going to build is going to work really well out there. Right. And I think that's a big thing that is missed. Right. Because I do believe founders should have an eventually a little bit of PT bar in them. Right. They're in charge of vision culture and fundraising. So tell me a story on why I should believe that this is going to be big and generate the type of returns for our investors. Don't tell me you invented the next biggest thing here because you haven't told me anyone wants it yet. I had a mentor one time when I was first getting into angel stuff and he'd been fairly successful and like anything with angel, right. You have a you have a low hit rate, but you're hoping for big wins. And he said I asked him one time kind of similar to what I was asking you know, it's like what's like your big what's a big red flag for you. And he goes if they say the words, but they should he goes run get run away. He goes stand up run away. Turn off the zoom. He goes because if they say, but they should they're solving a problem that doesn't exist to your point. That's why I'm sharing that. You know, you're about solving problems that don't exist. He's like, that means they have manufactured a problem for an audience. That doesn't have the problem. And maybe it's real. He goes, but I don't like investing in maybe. So I think that's a really good point. And I, and I, you know, one of the things I advocate a lot when I'm especially when I'm talking to younger founders is to read copywriting books. Not you don't have to want to be a copywriter that that's not why. But copywriting books, one of the very first and core functional messages you're going to get out of them is sell the transformation, which is your sell the win, not the not the sale boat or whatever. And being able to articulate the transformation and that part of it. I feel like we, we, we don't talk about that side enough. I think I think people who've been in a game a lot like yourself who have, who've had the wins, you've had the loss who felt, you know, both the bolts and downs. I think this becomes almost like intrinsic knowledge and intrinsic understanding. But for those who haven't the first time founder mentality, they want to drop into futures and benefits. Well, I can make it go faster. I can give it more, you know, tokenization or I can bring the API quest down or whatever. And you're like, that's great. But, you know, that is, that's not most people's problem. And then someone, and I think this is, and this is for the audience obviously, because you know this, but. It's like selling on price, right? Like if you, if you're selling on the connectivity of your API or the reduction in token cost or something, someone can then just come in and go, yeah, well, we're 10% less. Why would you stay with them? And you're just like, okay, well, why would I stay with these guys? These guys over here are 10% less. And now, the entire problem that you thought you're solved has just been wiped away and someone else has taken it because I had no emotional connection. When you're talking to founders and advising them and you've, how do you, if they're, if they're not there at the beginning or aren't all the way sold or maybe this just isn't intrinsic to know how do you coach them up on this idea? How do you get them to start thinking in the wind, not that not to sail, but I love that analogy, by the way, I'm absolutely going to steal that and use it again. I will credit you though. So in, in, in, in, in, in, in, you'll have that. Well, we need a back credit, the original partner, yeah, I heard it from so, I want to do some wide research on man, is there something? So, how do you coach them up on this idea? How do you get them thinking about the business or the problem they're solving in that way? Yeah, it's, it's a, it's a good question. So, I mean, traditionally, if they ask, if, if I start asking these questions and we're part of the diligence process or in a first meet, that's my red flag. And in a lot of ways, then it's not that I won't see them again, but we're probably not going to move forward past that, right? So, I would say they're, they're not going to listen to my coaching at that moment, right? But let's say post investment, it starts working itself towards losing vision and getting really focused on something narrow pet projects, we can call them or things like that. Or I think it's, it's reminding them what the original vision was for the company and to go execute on that. You know, specifically when it comes to co-founders, right? I like having meetings together and then I like having meetings separate. And I like doing things that aren't the dog and pony show, right? Let's meet for a drink. Let's, you know, go play nine holes a golf. Let's go do something where the, the mask comes off and you can learn a little bit more, especially during the diligence process, right? When you get them out of there out of the boardroom, the pitch room, if you will. And you can learn a lot about do they share the vision with each other? Because one of the biggest ways that that company's fail is, is not alignment in, in true vision for where things are going. And so I think it's a lot of checking in, you know, I'm on a few of our boards here at the company and it's a lot of active discussions and active management on our part aside from just being a board member, but truly being there to your point as a mentor in your own way to say, hey, that sounds good, but are we getting too far off track from where we were? Or, you know, in lieu of putting the hard work and time into executing that strategy, pivot somewhere else, because it seems easier. Is it really easier? Is it a distraction, right? And that's really a lot of those discussions are trying to stay focused on on what you're achieving. And if there needs to be a big pivot, then let's make a big pivot, but don't be scattered. And I think that's typically when you're trying to solve problems, you can sometimes to your point, manufacture your own problems in your own company to go solve instead of doing the work that sometimes is the most painful, but the most effective for the business. Another thing I've seen you talk about a lot is, when you see the market moving, left, you want to go right, right, you want to take that contrarian viewpoint and not everyone is comfortable with that. Some people like being fast followers, which is fine. But I would probably say my own focus in life in general and also investing would probably be about the same. One, where did that come from? Is that just native to you or is that a learned skill to kind of look at the world, you know, kind of watch where people are going and move the other way? Why is that valuable? And what are you seeing in the market today that has your eye that you don't want, you know, I don't want you to give away the secret sauce or whatever, but you know, what are some of those places today that you see, hey, everyone is looking over here, but there's some opportunity in these areas. As a contrarian take. Yeah, and I think the contrarian thing, I mean, you could probably quote it down to warm buffets warm buffets in the capital markets, right. I used to make the joke when your Uber driver is giving you stock tips, it's time to really question where your positions are, right. When you see everyone pouring in capital to a certain industry, it's going to be hot. But it's also going to have a lot of loss. There's going to be a blood bath at some point traditionally and being able to figure out which which ones the good one or not, you know, I've talked about before, if you look at the tech bubble, right, back in the 2000s, you look at crypto and the IPO market or ICO market, right. And the minute you start chasing is the minute NFTs NFTs, I'm happy to say never bought one NFT. So, you know, specifically, and I won't go deep on crypto, but I've been just a retail buyer of crypto since 2017. And have a long hold strategy. So when everyone's selling and saying how great they were to get out, I just look at the account and go, but it's down, it'll be back. I've gone through enough of these over the past, you know, what, eight years, seven years that it'll come. And if you look at it as a linear investment over the last seven years, even where it's called bottom today, it's doing quite fine. Right. I'm not a swing trader. I'm not trying to scalp yield. So while everyone else is, you know, fear uncertainty and doom, I'm just going, this is fine. Right. When we look at our companies, I just want to ask you a five question there because, yeah, of course, what I hear in your voice and what you're saying, I so relate to you. I used to get made fun of because I tell all my friends, I have gold and silver buried all over Albany County, which I live in Albany, New York. And, and, and, well, I'm doing all right today. You know what I mean? I just watched it creep along and I, you know, it's not like it's my entire portfolio, but it's the same thing with bit. What I've heard throughout so much of our conversation is like a very pragmatic, not anti emotional, but a controlled emotional response to investing. Most retail investors in particular are all emotion. How did you, how do you craft that? And if someone is finding themselves looking at their, we'll just use crypto as an example, right? They're watching Bitcoin have in the last four months and going, you know, I'm an idiot. All my friends were right. I should have never bought this crap. Like, how do you remove that emotion and, and reevaluate where you are, particularly when you're going down and not move out of positions that you, that will be valuable in the future, I guess is where in front of. Yeah, so, so look at it a couple ways. One, never invest in anything. You can't afford to lose. So let's start there. Right. I am not a financial planner. Don't have my series 7 and 63. I managed no one's money. So this is not financial advice. This is the Chris Van Dusen strategy. Right. I just want to make sure I say that out loud. I don't want someone going to do something. But if you look at a portfolio mix, right. You're going to have, you know, your capital markets, you're going to have your fixed income, which is, you know, actually receiving cash. You're going to have your alternatives and then your alternatives, you're going to have maybe venture private equity, right. Some real estate, well, natural gas. Who knows, right royalties. And then you might have a small little bucket called opportunistic. And within that, that is at least for me, a place where I put money into something that is a loon shot. Right. And again, this isn't, I'm not speaking for a select capital or anything. This is Chris Van Dusen. Right. And so back in 2017, I took a little bit of money and put it into crypto and said, this could be zero or this could be something. Now over the past seven years, it's turned into something and that's awesome. Right. It also could have been zero, but the point was I was in the idea of holding. And so if I were checking it every day, worried about the plus minus 5% that it goes all the time. Right. And I said, hey, I'd give myself an ulcer, right. Because this is the most volatile market. I think we've seen in quite a while. But also it was never to make money today off of, right. And so that was the thesis when we went in. That's not to say people watching the market go down and up in the regular capital markets. And it's tied to your retirement, your retirement's coming up. That's could be meaningful, of course, right. But in the same way, it's really hard to beat, right. The S&P over a 15 year run, least over the past historicals, right. You know, on average, what 13 14%? So you want to try and time it better than 13 14% on trying to buy and sell in and out. Maybe good, like awesome. I don't have that kind of time. It sounds exhausting. Right. So you just know what it's going to do. And if you check every day or every hour or every week, I think you're going to work yourself up more. And then what happens is you start selling. And you start listening to the news and then you start getting out of position. And then the minute it starts going back up, you buy back into the position. I mean, that is literally you watch everyone. The minute things go down, everyone sells out, right. And you're going, well, wait a second. You should have bought a little bit more at that point. It was free yields because the fundamentals of XYZ company are so great. It's going to be right back up to where it was. Right. So on the capital market side, yes, on the pragmatism around investing in companies. If you get emotional is when things go wrong. So I used to make a joke. Never bet on the team you're a fan of. So if you're a red socks fan, a Patriots fan, right. And you do, you know, fan duel or whatever those betting sites are never bet on them because you can't objectively look at it. In the same way, it's really tough to invest in a friend because you're not objectively looking at the opportunity. So if you're making a investment decision clouded by things that aren't how you evaluate the founders and how you evaluate the opportunity, you're going to end up making potentially a mistake. When you have a passion for the Patriots, you're not going to truly feel that that line is appropriate. So never bet on your the team you're a fan of in my opinion. Doesn't mean you can't grow to be a fan of the company, right. But the idea is you should be looking at it on the merits of the company and the merits of the founder and whether or not they can do what they need to do. So yeah, I think it's a highly pragmatic view on investing and I think a lot of ways you have to be. Yeah, I love that because I have buddies who want to fancy themselves as quasi traders and they love to regale you on the golf course or overbears of the stories of their wins. And what they don't tell you is they had to take five moonshot go broke chances because they had traded their way to almost zero. And you know, you don't hear those sides of the stories when you're trying to time the market and all this crap and I just, you know, the number of people, I mean, if you look at even trading firms, the number of algorithms on algorithms and the pace that they have to trade at and all the big losses and the movies that have been made about the big losses and you're like, but you sitting with your Ameritrade account while you're stamping TPS reports and sign across your desk, you're going to time the market perfectly like, you know, that's the kind of stuff where I'm like, we need to back up and live in reality now. If what if that's your gambling account, like if that's how you like to gamble, right or whatever and it's not like you said, it's not going to hurt you if you lose it and it's fun for you. More power to you. It's America God bless you. Like go get it. But like, it's worrisome. I think when I want to hit you with this question and I want to be respectful of your time. But I think if I don't, I heard this the other day and I want to get your take on it from your seat. I was listening to, I don't know if you're familiar with the podcast Anthony Pompliano. He's got a podcast. I'm Bitcoin and he has this gentleman, Jordi Vissaron, who I find to be fairly fairly smart and the things that he doesn't I like listening to him and he said, there is a cultural movement happening, particularly with people under the age of 40 where everything they're doing is like high stakes gambling moonshots. It's polymarket. It's meme coins on, you know, for crypto, it's, you know, these these big bets, these because they feel like they can't grind their way out, right? Like this idea of like, hey, I'm going to put 10,000 bucks in Bitcoin. I'm going to let it sit there for a decade and we'll see what it is when we get there, right? And I'm just going to emotionally detach from it and it's going to go up and down, you know, do you see that as a real cultural movement? Do you agree with that? Have you seen that in some of the investing things? Do you actually, this is the part that he did not touch on and as I've thought about it, I've struggled. I just don't have a good feeling for it yet. Is that because of social media and how hard these things are marketed to them and the, you know, you're only hearing the big, huge stories you're never hearing about all the losses so they believe it's possible for them. Or is it is it a reality of where our economy is and where our society is today that they simply can't grind their way out and if they don't hit some sort of moonshot, they're going to be eating ramen, you know, driving a 95 Acura and not getting laid. You get what I'm asking you there. You do. So there's a few things at play in my mind, right? I have an 11 year old daughter. We work really hard to make sure she's not on devices to the level that, you know, many others are. And no judgment just that's our values. And even still culturally. She's in fifth grade. The dopamine fixes that all these kids have of constant right need this the next act to the next the next the next the next the next the next. Is an interesting way of looking how these generations that grew up with screens, you know, I grew up your 45 and 45 I grew up with one television right in the family room that was used at night and maybe Saturday morning cartoons and other than that screen free. I mean, it looked like that. It looked like an air conditioner outside of your house. Yes, it was huge. And so if it wasn't if you weren't on that one screen, you were out right and now everything is a screen. I mean, down to all kids right wearing Apple watches. Sorry, that's a screen right. It is giving you feedback and you are doing something with it. And so if you spent all your life getting things and things the idea of being patient just isn't a skill that you've learned. And whether or not it's what you did for your career, what I did my career. There's a patience in spending the time on the mat to get where you need to go. Right. I remember even sitting there and I'm, you know, 45 were both on the cusp of being what would be called millennial versus a Gen X right. I spend a lot more of my, I guess personality would be more akin to a Gen X the millennials and I remember so much complaining about millennials being they think they know it all. I've got a 22 year old yelling at me that he doesn't that I don't know what I'm doing right. I'd hear this from managers and you go, okay. Maybe they're right, maybe they're not no judgment. However, that generation was the know it all generation. And I think this generation that we're referencing here right that's really spending the money this is these younger. I don't call them kids, but right in their early 20s and teens are the dopamine fixed generation. So the idea of taking $10,000 and putting it in an account to buy Bitcoin and checking it in a decade. What? Right. Like they're not going to do that. The idea of going and doing a career to a point where you know enough to go start a new company. I just say I'll start it now. I know everything I need to know. I chat GPT on my info. Right. Like there's a abundance of information for them to have and that's wonderful. Right. I wish I had all this opportunity when I was back in high school in college. Right. But you still need to spend the time learning. The nuances and complexity of what life is. And so I look at it from not only a career perspective, right. The idea I can dig myself out. Right. I can go get a job to do things and with AI it's I'm sure going to get even harder to find certain jobs. So I want to be sensitive to that. But the idea of of being patient, I think, is is tough for this generation. And so I think it goes to Robinhood accounts and GME and you know, being marketed to on social 100%. Right. When we were growing up on the USA network at midnight, you could see a get rich quick and real estate infomercial. But you weren't hit with these type of things. Right. The idea of coaching not good or bad just wasn't as much of a thing you saw every single day. And so there wasn't people telling you that you can do it. All you have to do is take my class and you can do it. Right. And so I guess that the idea that I don't want to call it get rich quick. But the idea of get rich quicker than normal. Was never as pervasive when we were growing up. And I think now it's extremely. And there's always another coin. There's always another strategy. There's always another person to follow as long as you pay them for it to get there. Yeah. No, I agree. The concept of paying your dues. Simply, it doesn't exist. I mean, it's not even something that's discussed. And I coach different seasons, both of my kids in different sports, you know, once on basketball, once on baseball. And like some of the things again, it's just some of the things that intrinsically, you know, I would believe and I'm assuming you would or you wouldn't have played baseball and cars, etc. Like this idea of like, I'm a freshman. So I'm going to keep working on my game because I don't necessarily deserve to be on varsity yet. I need to pay my dues to get there. And kids today are like, well, you know, I hit 300 in eighth grade. So if I'm not on varsity, I'm just going to change schools. And then I'm going to, we have this. I don't know if you guys have this where you are, but on New York State has a rule where kids can re re re factor themselves, regrade themselves. So if they're, if they're in this window, they can actually hold themselves back a year to then now, now like you have adults playing varsity basketball against children because they re factored their grade, you know, a grade they're in, you know, to, to be the star instead of I don't know, just putting in the work and the time to actually become a true master. It's all about gaming the system to put yourself in a situation where you feel like you're the star or, you know, you see this in travel sports. I don't know if you're talking about these travel sports, but holy shit. Like the number of games that are played, shell games that are played so that dad's son can be on the fourth travel team, but he gets the start of shortstop and hit number three. You know what I mean? It's like it is bananas to me and I don't think any of it leads to success down the road. Chris, I do, I can talk to you all day, man, I love it. This has been fantastic. I want to be respectful of your time and that of the audience. I know there are people that are going to want to follow along with you and what you do. Where are the best places to go deeper into your world. Yeah, LinkedIn, it's Chris M is a Michael van Dosen same exact thing on Instagram as well, pretty active on both. Anyone wants to reach out. It's see van Dosen at Psycho Capital dot com would love to chat. Appreciate it, man, guys, I'll have those links in the show notes, whether you're watching on YouTube or listening wherever you do, just scroll down. I appreciate you guys for being here. I love you for being here. We're out of your purse. Join Midnight Casino and discover a whole new world with hot slots jack parts live casino roulette and blackjack at the ready. Come and play your way get 100 free spins when you spend 20 pounds on eligible games. Search Midnight Casino or download the midnight app today. Midnight Casino Dumbair you decide. 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