We Study Billionaires - The Investor’s Podcast Network - TIP405: The Future of Fintech w/ Ryan Caldbeck

Starting point is 00:00:00 You're listening to TIP. On today's episode, we are exploring some very interesting topics around fintech, entrepreneurship, and the pitfalls of crowdfunding with Ryan Caldbeck. Ryan is the founder and chairman of CircleUp, a platform that set out to democratize investing, but ultimately pivoted away to a different model, and we discuss why. We also discuss leadership techniques Ryan learned from Coach K,

Starting point is 00:00:23 the famous basketball coach at Duke University while he was on the basketball team, the traditional path and alluring appeal of beginning. becoming an institutional investor, but also what it can sometimes lack. The hidden misalignments of incentives in the crowdfunding space. How investors can protect themselves while considering crowdfunding deals, insights into building your own board, team, and cap table, the future of fintech and web three, and a whole lot more. Ryan is an experienced investor and operator who has surrounded himself with a large network

Starting point is 00:00:53 of other great investors. So there's a wealth of knowledge here. So without further ado, please enjoy this discussion with the very thoughtful Ryan Caldbeck. You are listening to The Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected. Welcome to The Investors Podcast.

Starting point is 00:01:27 I'm your host, Trey Lockerbie, and today I'm super excited to have with me, Ryan Caldbeck on the show. Ryan, welcome. Thanks for coming on. Thanks for having me. I am very excited about our discussion today, which is going to involve. have a lot of talk around not only your background and how you funded Circle Up, but crowdfunding in general and where this is all going. That's such an interesting space. And you have such a

Starting point is 00:01:52 great background. So I wanted to kind of start there and learn a little bit about how you got your start. What led you to founding Circle Up and how you got to where you are today? So I am from Vermont originally. I grew up there. I went to college down at Duke. Out of college went into consulting at BCG and then business school Stanford. And in business school, it's a great opportunity to explore what you want to do. And I did not do that business school. I went into business school with a mission, which was to get into growth equity. And that's exactly what I did. And there's a lot of incentives to do that, whether it's financial or you've got a lot of encouragement from the career center and whatnot. So I went into growth equity in 2005. And there were parts of it that I really

Starting point is 00:02:39 liked, frankly. I did that for six years or so, six almost seven years, really liked who I worked with, loved the team, the pay was phenomenal. Frankly, the hours were incredible. But I just didn't feel like I was building what I wanted to build. I didn't think I was doing what I wanted to do. You know, after the best days as a growth equity investor, whether that was like a huge bonus at the end of the year, a close deal, or whatever, I never felt pride. Never felt like I wanted to talk to my family or friends about what I was doing. It always changed the subject. And after a lot of soul searching with my then-girlfriend, now wife, I want to try and build something, build something that'll help others. And that's what led me to start circle up.

Starting point is 00:03:20 Real quick about growth equity, there's a distinction here because you've got your venture capital, your growth equity, your private equity. You specifically chose growth instead of, you know, venture or even private equity at first. What led you to that? Is it just a certain market cap, you know, check sizes you're writing, is there a certain appeal for industry? What was the appeal of that space in particular? I think it'd be disingenuous for me to say, like I had some grand understanding of that world, frankly. Had I, I probably would have gone for venture. I think, first of all, the terms have changed over time and that landscapes evolved quite a bit. But when I was doing it, private equity, a lot of leverage, much, much larger deals, venture,

Starting point is 00:04:04 was almost at the time exclusively technology, certainly no leverage, typically companies that lost money, much more speculative than the growth equity deals. And again, those definitions have changed over time. For me, it was, those were the best firms that I got offers at. That's it. There was not any other grand mission beyond that. So I wish that I had taken the time to do that. It's funny, you know, we're kind of coming at this in opposite ways. I was an operator and have been and still am, with aspirations to do more and more just investing down the road, you started as an investor and then became an operator. I'm kind of curious if there's an interesting point here about fulfillment because I've heard writing checks and that side of the table,

Starting point is 00:04:47 if you will, can be not that fulfilling because you're not the operator and you're not getting that experience. Is that what you were craving at the time? Or was it about the actual product itself you wanted to see in the market or a certain problem you were trying to solve for? What led you to the circle of landing on that idea in particular? You know, some of the realizations that I'll talk about now were clarified over time after leaving growth equity and becoming a founder and CEO. Some of them I knew at the time. And some of them I knew, frankly, even before.

Starting point is 00:05:19 So I guess it probably starts when I was kind of late high school, early college from, as I mentioned, Vermont originally, and JetBlue, the airline moved into Burlington. And I remember reading an article in the newspaper talking about that and state and certainly the area that I lived in was incredibly excited that JetBlue is going to offer one-way flights to New York City for 50 bucks or so, 25, 50 bucks. And it kind of like opened up this whole new world to the people that lived there of how you can just go there. It doesn't take seven hours to drive through the snow.

Starting point is 00:05:51 You can just fly there, have a night and fly back. And I remember thinking like, what an amazing feeling it must be to create something like this, JetBlue, that creates so much joy for other people. people. And for many years, I thought, like, I don't care it's a cardboard box company or a zipper company or whatever. Like, I just want to build something that helps others. And then you go to college and then you talk with a career center and then you get into a great place like BCG. And then the people of BCG encourage you to go to business school and business school encourages you to go to a hedge fund of private equity. And you let yourself get put on a kind of hamster wheel.

Starting point is 00:06:27 And that was my fault. I remember in college, I talked with the head basketball coach. at Duke, I was a walk on at Duke, so Coach Kay, who's retiring this year, about offers that I had coming out of college and an offer at McKinsey, Bain, and BCCG. And I went to meet with him and he said, well, what are you passionate about? And I just, in the moment, I remember where I was sitting when he said this. And I was like, I kind of, I didn't roll my eyes in front of him, but like in my head, it rolled my eyes. Like, thinking like, coach, you're lucky that you get to work on what you're passionate about. Like, I have to put food on the table. I need to get a job. and I think it should be a good job.

Starting point is 00:07:01 So like, we've got to pick here are the options. And it probably took me more than a decade to understand what I think he was saying, which is like, you're talented enough. And I think this is true for the vast majority people, like find something that gives you passion that you want to think about on a Saturday night or on a, you know, in the shower in the morning, that you just, you know, obsess over. And that was not private equity for me.

Starting point is 00:07:24 It was not consulting for me. I'm not sure that Coach Kay is like Uber passion. about basketball. I think he's passionate about building teams and creating something that's bigger than himself and bigger than the players only. And I missed that concept of finding like the root passion for me. And so had I taken the time to take a few steps that I would have understood like at the time I was passionate about basketball, but had I really thought about it like, I wasn't really passionate about basketball. It was like, how cool is it when you can come together with other people to try and accomplish a goal to climb a mountain together? I loved

Starting point is 00:07:58 when I had leadership roles on different teams. I loved talking to teams. I loved being a leader. Those are things that are not skills that are really utilized in growth equity, to be frank. You don't really have much of a team and you're not really looked upon to stand in front and rally the tribute to climb a mountain in the same way. And so it took me a long time and frankly took me being successful as a growth equity investor to realize that I didn't like it. had I failed, I think I would have continuously tried to push like, okay, I'm just getting better at this. Then I'll like it. And a problem was like, you know, my last couple years, it went very well and I still was unhappy. And I had some phenomenal years that like I left

Starting point is 00:08:42 each kind of comp conversation or closed deal thinking like, me, I don't really care. It's true. I loved the CEOs that I worked, have loved my team. But in terms of like the accomplishments, I didn't feel much satisfaction, much intrinsic satisfaction from that. Well, that coach K-piece is incredibly interesting. Didn't come up in my research, but now I'm filled of questions around that and what you learned from him, not only finding what you're passionate about, but oftentimes when you go off and you found your own company, you become the leader. Not everyone is equipped or even aware that they need to graduate into being a leader of

Starting point is 00:09:21 a company. You know, oftentimes when you're founding something, it's just you. And that's all you're worried about is getting this product out. But as you grow and scale a team, that becomes more and more important. So I'm wondering, were you a natural born leader or were there tips and tricks you learned under Coach K that even applied to your business later on? I think it'd be probably arrogant or whatnot to say I was natural ball leader. I can say that I was always interested in it and drawn to it, whether or not I was good at it or I'm good at it today. is a different question, but like, I remember in grade school teachers asking me to lead different

Starting point is 00:09:56 things that seemed very unique and out of the ordinary. And in hindsight, I think, complimentary. And then we're awesome opportunities. Yeah, or captains of different teams or being just asked to step up in different ways. I loved it. I still do. I love that opportunity. And I also learned a lot from Coach Gay. You know, to be frank, like I don't usually like the analogies of sports and business. Sometimes they work, like the concept of like an organization being more like a professional sports team than a family, I think makes a lot of sense. But a lot of the tactics that coaches use in sports teams cannot be used in a business setting. You can't scream at your team.

Starting point is 00:10:38 You know, you can't swear repeatedly at your team. You can have an engineer who can quit and can get a job of Google the next day. That's a different sort of interaction and relationship than exists, at least when I was playing college basketball, where if you transferred, you have to sit out a year. There's some things that don't transfer over to business, and there's a lot that does, particularly around helping to understand motivations to help people and help recruit people and help people buy in on a common mission to be a part of something bigger than themselves. I was at dinner with some C-level executives from J.P. Morgan right before COVID, and

Starting point is 00:11:15 we talked a lot about with some of the fintech executives, like the concept of what leads great talent to go to a startup. And one of the things I talked about was like intrinsic benefits, meaning the opportunity to grow, the opportunity to help build something, the opportunity to have a seat at the table, the opportunity to like, I feel like you're in the game. Coach K was amazing at doing that. I was a manager my first year, which means I swept the floor, made Gatorade, and I was a walk on in my last three years.

Starting point is 00:11:42 And you feel like what you're doing as, as a manager. This is going to sound like a joke, and I really don't mean it's, but he makes you feel, when you're the one holding the marker to hand to him in a huddle, I will tell you, you feel like the most important person in the world. And if you screw up taking off that cap of the marker, and this is not a joke, like, you think about it for days, or sweeping the floor or the gatorade you're making, he just has an uncanny ability to make you feel like your job is important. And I think that that lesson is something that I tried to do a lot with the team when I was

Starting point is 00:12:15 CEO. You know, another one is just the importance of clear communication of getting everyone on the same page. He did that in extraordinarily effective way, making sure that everyone was rowing in the same direction, communicating with urgency and directness and looking each other in the eye and having hard conversations and being willing to hold each other accountable. Those were all things that and many, many more things that he taught me that I've tried to build on as a leader. Now, you know, I'm not trying to compare myself to good gay at all, but I certainly he gave me a North Star to strive for. Let's take a quick break and hear from today's sponsors.

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Starting point is 00:17:00 Well, sure. I mean, not everyone gets that kind of mentorship, especially from someone like, Kim, even directly or indirectly, as you kind of mentioned. Going back to Circle Up, which is the company you founded after coming out of the growth equity space, was there an opportunity there that you, I guess, better asked is, what was the opportunity that you saw that you said, I'm going to leave this growth equity industry and go in on this, solve this problem? Well, the first and the most important opportunity is I wanted to build something that had an impact on other people. And so if it wasn't going to be circle up, it was going to be something

Starting point is 00:17:31 else. I wanted to, I go through an exercise with my friend, and girlfriend now, wife, Kim. She going to help me over the series of several weeks on Saturdays draw out what did I care about, what did I love, what did I feel passionate about, what did I not like? And we created these huge posted boards that we'd write on each Saturday for a couple hours. And some of them would be silly things. I like Buffalo wings. Some of them would be very important things. I loved to help someone else grow. I loved it. In basketball, I always, this sounds probably like a maybe it's altruistic or whatever. I don't mean it to be. It's very selfish. Like, I like to pass to a basket more so than I like to score myself. Like I get goosebumps when there's like a backdoor cut or whatever.

Starting point is 00:18:17 And I feel the same way about being a CEO. Like when I can help someone else be successful on my team or outside the team, like a customer or a teammate, like I just love that. And so it was that exercise that helped me realize like, okay, I don't think this is invest. for me. I think it's building an operating company. And then in terms of like the business opportunity, quick background about Circle Up started as a marketplace that helped connect investors with consumer companies, consumer meaning food, beverage, personal care, pet products, things like that. That's an industry that's about three times the size of tech has terrific returns on par with tech, but with about half the volatility of tech. And yet there's about 150th, 175th, the amount of early

Starting point is 00:19:00 stage funding for those companies, at least there was at the time. And I started to circle up with the thesis that all the returns are great. The problem in this industry is that the cost to find the companies is just way too high. So there's no Silicon Valley for these consumer companies, right? The companies are just as likely to be in Portland, Oregon, Austin, Texas, as they are, L.A. or New York. On top of that, there's no infrastructure like Y Combinator or TechCrunch to help investors and companies connect more efficiently. And so Rory and I had the thesis that you could use a marketplace model to help these companies connect. And over time, I valued them in a variety of different ways. So that was the original idea behind CERCLAO. Great idea in concept, right? Fantastic idea. Like, I heard

Starting point is 00:19:43 about it for the first time and said, oh, my gosh, hallelujah, someone is democratizing this and getting people involved in these companies who need funding and making that connection. So what went wrong? You know, how did that not prove out? And because, you know, ultimately CERCLA pivoted to other things. So maybe talk to us a little bit about why that was. We pivoted after about five and a half years or so, about five years to another model, which I'll talk about in a second. You know, I think it depends. In some ways, Circle Up did really, really well with that model. We attracted some phenomenal investors. Union Square Ventures was our lead investor, along with Google Ventures, Canaan Partners, Rose Park, which is Clayton Christensen's fund, did really, really well. The

Starting point is 00:20:27 Vanity metrics, things like GMV, were fantastic. The problem, and I went to the board about this in advance of recommending that we were going to pivot, or that we pivot, was that it didn't seem like we were building a good business. Vanity metrics were great. We were going to keep raising money as a technology startup because sometimes there are investors who even in a late around like those vanity metrics. I just thought we were selling dollars for 40 cents, 50 cents. So why?

Starting point is 00:20:57 I think the biggest reason, and I have put out some content about this on Twitter, I think the biggest reason that model didn't work is that the financial feedback loop took years, meaning if you're an investor and you came on a circle up and you invested, it would be five, six, seven years before you got your money back. And so, you know, we had investors that put money into Beyond Meat early. And there's one investor that put $250,000 in and took out about $31 million. And that's a phenomenal richer and it took five years. And so along the way, you know, you can give them updates on how the business is doing. But fundamentally, if you're not able to take your cash out, there's a lot of investors who are going to be hesitant to put more money in. I think that feedback loop was brutal and made it really difficult to encourage at least the investor side of the market. For follow-on investment, ultimately. For follow-on investment. Yeah. And if you're just acquiring new customers, which would be the investor side of the marketplace, each time, there's not much of a network effect there. And you're kind of selling deals then to a new

Starting point is 00:22:07 investor base each time. And that's a hard way to build a business. Uber and Airbnb and others work because both sides of the marketplace tend to be repeat customers. There's a frequency of transaction. You know if you like your Airbnb immediately, if you like your Uber ride immediately, And you can give feedback on that. And both sides can respond to that feedback. So I think that that's probably the number one reason. There are a number of other reasons as well, but like the number one reason why I think that that model did not work is that one. So that explains it from a business point of view, but from the actual investors using the platform and the businesses, was there a fundamental flaw there as well? Or was it just strictly on the business side? Look, I'm biased. Right. So let's caveat everything I'm going to say with that I am biased. I think the equity marketplace or in some cases, crowdfunding, and I always kind of bristle at that term, but other people use it model. I think works in some industries and it really

Starting point is 00:23:04 does not work in others. So in the technology world, there's a lot of sources for capital, for technology companies, a lot. And in the consumer space, at least for companies with less than 10 million in revenue, when we started circle up, there were not. And so I think that there is an adverse selection that exists in these types of marketplaces that work with technology companies that didn't think existed for our consumer companies, but of course, unbiased. At the time when we started circle up for several years, if you Google early-stage consumer product funds, you wouldn't find five in the United States. If you did the same thing for technology, you'd find 750, as an example. So I think adverse selection is meaningful for some industries on the entrepreneur

Starting point is 00:23:42 side. I think the cost to working with a wide variety of investors is pretty meaningful. particularly those that are less sophisticated. And you see that on some of the platforms today, you've got a lot of dentists and doctors who invest and don't understand really what they're investing in to. That leads to real issues. And on the investor side, beyond the adverse selection, I think the concept of like getting transparency into the deal, the valuation, how the deal performing an ongoing basis, etc. I don't like what I see out there. I mean, what I see is a lot of kind of pseudo-celebrity angel investors that raise syndicates or whatnot, and it scares me. It really scares me.

Starting point is 00:24:26 Some of them I've talked to privately, and they talk about, like, they put their worst deals in those, quote-unquote syndicates, and I don't know why that's a good thing. That point in particular resonates with me, because when I've been on these platforms, the valuations I've seen have been astronomical. And even in businesses and industries that I'm very knowledgeable on, I would say. You know, I look at these valuations and it seems just sort of like an abuse or something of that lack of transparency in some ways. Does that need more regulation?

Starting point is 00:24:56 Is there a loophole people are getting away with here? Is it just what is causing this kind of lack of transparency or lack of standardization, I think, when it comes to things like valuation? That could probably be a four-hour podcast on its own, to be frank. I think that a lot of the regulation in private investing has hurt investors, frankly. I think accredited investors, you know, people have more of more than million dollars in net worth, excluding their home, make $200,000 a year as an individual $300,000 a year. It was a couple.

Starting point is 00:25:25 Those are investors that have access to be able to invest in a private deals, whether those VC funds, hedge funds, or individual deals. And it allows them to be wealthier. The rich get richer. And undercredit investors don't. I don't think that that's fair. And I think the lack of information standardization is a really bad thing. I think the only or maybe one of two platforms that got registered by FINRA.

Starting point is 00:25:50 So we were a registered broker dealer because we were trying to do it the right way. The problem with that is that then the things we could communicate about these companies, which was much more restrictive. And so information that I would have wanted as an investor, I couldn't tell our investors because FINRA prevented that. It's a shame. but I think that that's part of the inefficiency in that industry right now. So do I think that there's more transparency and standardization needed?

Starting point is 00:26:15 Probably, it's also hard for me to completely sign up for more regulation. I think the regulation needs to be different than frankly. I think FINRA needs a dramatic overhaul. And what's funny is people from FINRA would tell you that. People from FINRA would come in, do their annual audit of us as they do for all broker dealers, and privately tell us this needs to change, meaning FINRA needs to. change. But like some other organizations, it's just really, really slow moving. So what I like about this conversation is I can tell you have a passion for these unaccredited

Starting point is 00:26:49 investors. And having been one myself, it's I have the same passion and this is a platform to help equalize the playing field. And crowdfunding has become more and more prominent over the last few years. There's a number of companies doing it, as you alluded to, as new investors who are listening to our show right now are considering investing using one of these platforms, what would be like your best advice for trying to get your arms around the information as much as possible on a deal to make sure you're protecting yourself from some of the things we just talked about? Well, I'm really hesitant to give any investment advice. You should be talking to people that understand your financial, that, you know,

Starting point is 00:27:28 who I would listener is your financial situation and understand the investing world. I think some pretty safe pieces of feedback are, one, you have to diversify a lot. If you want to allocate, let's say, 3% of your investable net worth into private deals, that 3% should then be split up into 10 or 15 different companies. It should not be into two companies. That's just gambling. I don't care how good of an investor you are. The mistake people make is like, you know what, I want to do I put $100,000 into a private company.

Starting point is 00:28:02 And I'll just kind of see for a couple years. That's a way to lose a lot of money. Take $100,000 and invest it into 10 companies, 12 companies, and do better over the course of two years. Don't do it in a month. So I think diversification is absolutely critical. Then I would develop a framework on your own. There's a lot of blogs about private investing, Bill Gurley,

Starting point is 00:28:23 Andrewston Horowitz, Fred Wilson at ABC at USV, which is blogs, ABC.com. Sarah Table at Benchmark and more others, do a lot of reading about different frameworks and how to evaluate the types of companies you're interested in. If you're looking at a marketplace, Jeff Jordan, at Andreessen, Sarah, at Benchmark, etc.

Starting point is 00:28:40 To create frameworks on how to break down these businesses to understand them. And then make sure you get the right information to evaluate the company. A lot of these platforms, it's super high level information and they'll talk with the founder. And to me, that's a recipe.

Starting point is 00:28:56 It's a lot of money. It is, especially through these investing groups where I'm going to invest behind John Smith. John Smith may or may not have access to the data. By the way, he's going to get paid whether or not the deal makes money. That's a scary place to be. Talk to us a little bit more about that. What you're describing sounds a lot like what you find on something like Angel List perhaps where you're following someone well known and they set up a SVP or some kind of fund and you're leaning on them to find you the deals. Is that what you're referring to there as far as? I really respect founders who are trying to build something.

Starting point is 00:29:29 CEOs are trying to build something, particularly private markets. And so I don't want to talk about any specific platform. But in general, I think you need to make sure that your incentives are aligned with the people you're investing behind. And so if that is a fund manager or a syndicate leader, whatever it is, you know, do you win when they win? Do they lose when you lose? That's not true for all of these platforms. And I would just dig in hard onto those incentive structures. Because no matter who this investor is, if they win when you lose, you can be. sure that you're not going to be getting their best deal flow. And that's just because they're getting some type of advisory shares just for finding the deal

Starting point is 00:30:07 potentially. I just think it's something that is something important to dig into. I think it's possible to make good investments on these platforms. I think it just requires a level of sophistication and work that not all investors are willing to put in. And especially when it comes to like technology name that seems to be hot. And that's a really quick way to lose. a lot of money. Having started your own company, what have been some of the biggest

Starting point is 00:30:35 learnings or biggest surprises from founding it, fundraising it, nurturing it? What are just some of the biggest takeaways now? You've had some time to reflect on being the CEO of your own company. What are your biggest takeaways from that? There's a number of things that I will do differently when I am CEO again. The first thing you mentioned was funding or fundraising. I, in general, was incredibly fortunate with the investors that we raised money from. I mean, some of the best investors in the world, I mentioned some of them, also TPG, Tomasic, a number of others. So by and large, I felt really fortunate, really lucky.

Starting point is 00:31:09 And we had one or two difficult experiences, too. And I think what I learned from both those is that the importance of aligning on mission and vision is not just motherhood and apple pie. You know, companies, particularly startups, they change. direction. They have to change direction. And if you've got an investor that is just dialed into, let's say, the financial forecast that you put, or just dialed into the particular product that you're building right now or whatever it is, it doesn't really care or isn't aligned with the mission or vision, then when it comes time to tweak it, to tweak the product, to do something

Starting point is 00:31:43 different, that might be consistent with the mission or vision, but is not consistent with, let's say, the product that that person invested into, it creates a lot of pain. So getting alignment upfront on does this person care about the mission and vision? Why do they care? What does this mean for them? If we have to pivot the company, but we say consistent with the mission and vision, what does that mean? I think that that is absolutely critical. I think alignment in terms of values is also really important. And those comes through conversations. You know, a difficult thing. I've talked with a lot of GPs, general partners at different VC firms over the last couple months about how deals are moving really quickly and on Zoom. People are talking to the company for the first time on

Starting point is 00:32:23 Friday. I talked to the top four VC last week, two weeks ago, meeting company on a Friday and investing on a Monday. That sounds like a good thing for a lot of founders. And I would have concern that you don't really know what you're getting to bed with. Like, you don't understand if there's vision alignment, mission alignment, values alignment. And these are multi-year relationships. I'm not going to tell you it's as important as a marriage, but like, you spend a lot of time with these people and go through a lot of battles together. And I think some of the good fortune that I had with investors was because we did a pretty good job of diligent the most of them.

Starting point is 00:33:03 We made one pretty big mistake, but most of the time we did pretty good job. And some of it was just luck, just flat out luck. So I think, you know, from a fundraising standpoint, getting that alignment up front before you take money is important. On that point, what's coming to my mind is this comment, I think it's in the Bradfeld book Venture Deals. He says, you know, you should walk away when the... the potential investor during their due diligence starts to feel like a proctologist,

Starting point is 00:33:27 meaning they're digging in too much, right? So is there a balance here? Because, you know, I can totally understand that the snap judgments being made over Zoom. But on the flip side of that, there are other diligence processes that are much more involved. How do you strike that happy medium between the two? Rod's a great investor. And I think he's also not just a great investor from a return standpoint, but founders love working with him. I would probably tweak the point you're trying to make, I think, one, but I think for me, I would probably tweak it a bit to say, like, proctologists serve a good role in the world.

Starting point is 00:34:00 And I'm not trying to be funny. Like, they serve a good role. When the investors are asking questions that are just not productive, that's when you should walk away. I've had a colonoscopy. It stinks, but like there is a purpose to it. And diligence, I really liked when it was tough and asked really hard, but great questions.

Starting point is 00:34:23 Then, when there's diligence where the investor is asking just irrelevant questions, just things that have nothing to do with the strength of our business, that really detailed, droning on about just stuff that doesn't matter, that's when you should be scared as a founder. It's so easy for me to sit here in Silicon Valley and the fortune and privilege that I have and talk about walking away from an investor. There's a lot of entrepreneurs who cannot do that. it's not easy to raise money for a lot of founders. I would just offer up that sometimes it is worse to raise that money than it is to not.

Starting point is 00:34:58 There are some investors who are going to be willing to give you money and will make your life a living hell and not taking their money, even if it means the company didn't work out or yet to take it on worse terms, anything else could end up being a better thing. So the proxologist analogy, I know what he's trying to do, I think I just kind of tweak it a little bit to say like, you know, when they're asking, really detailed, unimportant questions and focusing on the wrong issues, that's only going to get worse. And it's going to suck up a lot of your time and be frustrating. And that frustration is going to shine through and you're going to spiral into a bad relationship with that investor. I love that nuance. I think that's fantastic. I heard some interesting advice the other day, which was basically something along the lines of you can have great terms and you can have a great price, but you can't have both. And if you were getting it,

Starting point is 00:35:48 given the choice, you would take the terms over the price. I'm wondering if you, just hearing that, what your general knee-jerk reaction takeaway would be if you agree with that statement or sentiment at all? Obviously, you don't have to pick one, but you're saying if you had to pick one, yeah, I'd pick great terms over price. Yes, for sure. I'm so glad that I'm not an active investor when I'm saying this. I do something I just manage an investing, but I mean, on behalf of an institution, like,

Starting point is 00:36:14 I just genuinely think price is vastly overrated. you know, if your company is successful, you're going to make a lot of money. And so, like, it might be the difference between three homes and four, but like, you're going to make a lot of money if your company is successful. Terms will make life very difficult. Poor valuation rarely does. You might end up with too little of the company, but usually good boards will give you more. Like, if you follow grants that I've written about that publicly in terms of CEO compensation, but terms are really hard to reverse and tend to compound in terms of the problems that they create over time.

Starting point is 00:36:48 As future investors come in, they either take the exact same terms of they sometimes make them worse. And that gets difficult. Is there some nuance there? I'm curious because I was thinking about Warren Buffett just now. Our friend Brent B. Shore had dinner with him once and was really pressing him on, you know, this handshaky kind of way he does deals and somewhat seemingly lack of due diligence. And I guess Warren said, price is my due diligence.

Starting point is 00:37:16 I mean, you really low balls or get something super cheap and that's his protection long term. So I'm wondering, that makes a little bit more sense to me innately just maybe in public markets or something where it's a little bit not so new or nascent like a venture deal. But I'm curious if that resonates with you. A couple thoughts. One, Warren Bob is a better investor than I am. So if you get a chance to listen to Warren, not me. Two, I'm talking about on behalf of founders.

Starting point is 00:37:43 I'm not talking about it on behalf of investors. Three, he is a public guy, right? He's not a private guy. Now, there have been some interesting examples that I'm thinking of where he did care a lot about terms. You know, in the 08 financial crisis, when he invested into Goldman, he did not get just a good price. He got great terms, too.

Starting point is 00:38:02 You know, I forget with us where I knew at one point, but like the terms are what made the deal attractive, you know, in a lot of different scenarios. So in the public markets, yeah, I understand like price matters or, or, you know, or even late stage, late, late stage prices are important for entrepreneurs and reps. I think the terms are more important. Let's take a quick break and hear from today's sponsors. No, it's not your imagination. Risk and regulation are ramping up,

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Starting point is 00:41:52 space? Did you recruit anyone who wasn't an investor to join the board? And if so, what was the profile you were looking for for that kind of guidance? There are a number of things that I will do differently next time I'm CEO. And one of them is I will look more actively for independent members. So we have had two over the past 10 years at Circle Up. One is the current CEO of Lending Club, Scott Sanborn, and the other is a phenomenal investor at Bridgewater. And I wish that we had always had one. But it takes time to get that. It's a bit like finding a therapist, frankly. There have been years where I knew I needed a therapist, but it's a 30-hour investment to find it. And it's just really hard to justify that. And so I'm doing it now, right, when I'm not

Starting point is 00:42:40 a CEO today so that it pays dividends throughout whether I'm a CEO or not. And an independent board member takes a long time to get. So we have had it, and I wish we did it more. The other board members that we had were the investors that led the various rounds. So Union Square was on our board, Key name was on our board, Arras on our board. They both are Rose Park Advisors is on our board. And then we stopped giving board seats after the series C or so. And that board has been fantastic for us. You mentioned when your CEO again. I'd like to kind of talk about what it looks like for Ryan called back to be CEO again,

Starting point is 00:43:18 what that venture would look like and how you would be different. I am, you know, at the beginning of this year, I was kind of 50-50 if I wanted to be an investor next or an operator. Now I am positive. I'll be an operator next. Eventually, I'll probably be an investor again, but I want to be an operator again. I love leading. I love building.

Starting point is 00:43:39 I love creating a team, creating a culture. I love the things that go into that. I'm in thinking a lot about, does that mean I want to join something as like a CEO, C-O, or do I want to start something? But I've done a lot of reflection on my time as CEO, like, what do I think I did well? What do I think I didn't do well? What would I change next time? And so, you know, in terms of like organizationally, there's a number of things.

Starting point is 00:44:00 things that I would do differently, or that I think we did really well, right? So I think we did a good job defining up front what to look for in teammates and to create a process to kind of insufferize that. I'm really proud of that and I will lean into that heavily next time. We'll actively recruit teammates with a growth mindset. I think that's critical in a startup. We'll actively try to build a culture that's intellectually honest, you know, that doesn't search to be right. It searches to find the right answer. I will value startup experience over big company experience, lean a lot into professional development for the team. There's a number of things like that that's mostly cultural that either I think we did well or I've learned from and want to do a better job of.

Starting point is 00:44:46 And I've written about that on my website, Ryan Caldock.com. In terms of like industry, there's a lot of different things that interest me. I've gotten a lot of calls on existing companies or starting something new in a variety of different industries from, you know, FinTech, I circle up as a fintech company, to other kind of subdomains within technology. And I find myself gravitating a lot towards Web3 stuff. I think it'll be the biggest technological jump in the last 20 years. I think it'll be more important than mobile, frankly. So I find myself getting really, really excited about that as an operator and what that unlocks.

Starting point is 00:45:20 But I still feel like, I think a lot of people that are going down that rabbit hole, I still feel like I am on the one-yard line trying to understand. And I've got 90-10 yards left to go, trying to understand the space and all the implications behind it. On that front, I'm curious to get your opinion on this. There's a sentiment out there about the Web 3 space that is essentially, I would put it like, a way for venture capitalists to take their company public sooner, you know, and without all the same kind of regulation, whether it's an existing company or new company,

Starting point is 00:45:53 there's this idea that people are going to be, you know, it's kind of the Wild West, I guess. So going back to that sentiment about protecting investors, how should investors be exploring this space and making sure that they're not subject to any sort of misalignment, as we kind of alluded to earlier? There is a lot of hype behind Web3. And, you know, I think we had a period two years ago, three years ago or so around the ICOs initial coin offerings where there is just kind of rampant fraud, frankly, and failure, failure and fraud of a lot of them. On top of that, there is tremendous volatility in terms of the

Starting point is 00:46:32 tokens and currencies in the crypto space. And so it is a space where you can see someone making millions, tens, hundreds of millions of dollars, and you can see people losing everything. And the latter is much more private than the former. What would I say to people listening? I'd say, first of all, Ryan is 300 hours in, not 3,000 or 30,000 hours in to understanding Web 3. There are some people who understand that market incredibly well. And I would urge you to spend the next year digging in before you put a material amount of money of your own into the space. Two, I think diversification is really important.

Starting point is 00:47:10 Fred Wilson has put out a post about diversifying in that space. I think is a really important one. But I hate investing in the things that I don't understand. and the more I have dug in, the more I think I understand it about it, even though there's a lot I don't. And the more I love it and think it is incredibly impactful. Well, let's talk about the benefits that you're seeing because I'm curious. You said it's a big comment to say biggest thing in 20 years and tech in the future. What does that future look like?

Starting point is 00:47:39 What are the investors, what are the benefits, I guess is the best way to frame it. Someone tweeted, and I wish I could remember who, because I want to give this person credit. it. You know, Web 1, which is kind of up to the early 2000s, was the right period. You would read things on the Internet on my website. Web 2, which is, you know, Google, Facebook, Amazon, etc., was read write, meaning you could also create content. This is sounding like a Greg Eisenberg tweet. Does that sound? Maybe. Maybe. And then Web 3 is read, right, own. So it gives people the opportunity to participate in the value that they are creating. More than a few people have commented that if you are using a product and you're not paying for it,

Starting point is 00:48:25 you are the product, right? And your data is being sold, et cetera. And there's been a lot of bad things that have come out of that. And some good things, but some bad things that come out of that, as the social dilemma, the movie would talk about. You know, when you think of an example, our company like Uber or Airbnb, for the market participants to own a piece of the market through tokens, as an example. if those companies were set up as DAOs.

Starting point is 00:48:48 That incentivizes them to help the market grow in ways that they are not only not incentivized, but in some ways perhaps even disincentivized to do in the current structure. I think that's a game changer. I think it accentuates network effects. So I think it's one of several different advantages or many different advantages to this concept of a DAO in that case. But Web 3 overall, like the ability to not just read Web 1 or read write Web 2, but read, write, own in Web 3, I think unlocks just some magical properties about building

Starting point is 00:49:21 organizations with new business models that can help transform the world. I'd love to get your take on, speaking of DAOs, there was a recent one called Constitution Dow where they were literally trying to fundraise and buy a copy of the Constitution from Sotheby's or some auction. When I was looking into that, I noticed that, you know, by buying a stake in the Dow, you weren't actually getting any equity of the actual constitutional document itself. You were getting these government rights or governance rights. So, you know, you could vote on where the document is stored or there's a few other examples they listed. And admittedly, very well and I would say very transparently written on the website of the company. So they were being very forthright with what you're

Starting point is 00:50:07 getting when you put money into the space. But I think that there were a lot of folks on Twitter or wherever getting involved thinking they're going to buy this and own a piece of this document. And when that document sells again, they're going to get some money from that. But that didn't seem to be the case as far as I understood it. So if you know more about this subject than me, I'm curious to know, because this is the only example I know yet of a Dow and how it works. And that seemed like a little bit of a misalignment or something that wasn't what it appeared on the surface.

Starting point is 00:50:37 But what's your take on it? that was happening during a week or a period when I was, when my family and I were visiting my parents. So I'll be frank with you and say I was a lot less in tune at that than I would like to admit. But in general, I think you identified one of the incredible benefits of Dows and one of the early complications. So incredible benefit of them is that they are extremely transparent, both in terms of how they are designed. The code is out there for anyone to see. and in terms of culture. I'm a part of a couple of different Discord servers

Starting point is 00:51:12 and some other groups that are actually talking about with three in particular DAOs. And a common piece of feedback about a DAOs that we're evaluating is around the importance of transparency. Who is the team? Where do they come from? What are the rules this doubt? And so while a lot of that is just structurally in there,

Starting point is 00:51:30 there's also like a demand culturally for them to be transparent, which I think is great. And I think the Constitution of Dow was transparent. And there are also people who will make snap decisions without trying to understand them. So when you can put $25 in to the, or $100 into the Constitution Dow, and it requires a fair amount of work to understand whether or not you are actually getting a piece of the Tao, or excuse me, of the Constitution, there will be a lot. And there were some people that just said, I'm not going to do the work. I'm not going to try and understand this.

Starting point is 00:52:02 My hope is that that evolves over time, that people become more specific. and the tools are created to help people understand what they're actually getting when they are committing to DOS. So we're so early. I think someone I heard yesterday on a podcast talk about like, we're not in the bottom of the first inning in terms of this world. So I think that there's a lot to understand, but just fundamentally what blockchain technology can do and lots of the other innovations over the last several years have allowed us to do not just in terms of moving money, but in terms of creating smart contracts and organizational structures that allow new business models to form, I think is incredibly powerful and gets me really excited.

Starting point is 00:52:46 So having been at the top of a company, you know what it's like to run a large organization. And as even Ray Dalio runs Bridgewater, there's that idea meritocracy element involved where not everyone's opinion has equal weight. So I'm curious, that's kind of what a Dow sounds like as far as the governance is concerned of a new organization, I guess they're weighted based on stake. But, you know, knowing how hard it is to run an organization top down, what would be the benefit, I guess, of having it more distributed as far as the governance is concerned? Well, it doesn't have to be run that way, right? So there are some DAOs that are not run that way. So some DAO's run based on how many tokens

Starting point is 00:53:25 you hold. Some DAOs are the values of the tokens or how many tokens you have are dependent upon, let's say, the contributions you make to the DAO or how long you've held them for, right? And so an investor coming in and out and doesn't add any value gets fewer tokens or, you know, et cetera, et cetera. So I think it depends on how the Dow is set up, but you can reward people for their contributions. And you can reward them for their contributions in real time. It's not just, you know, at the circle up, we would move comp twice a year, right? And a very imperfect measure of someone's actual contribution. With the exception of maybe a sales team at all organizations, it's extremely hard to understand through contribution. I mean, try interview

Starting point is 00:54:05 a product manager or a designer from Apple, like, good luck in understanding what they've actually built and how much it was part of them versus the team of 50 that was doing the same project. With, you know, Dow structure, I think that that is a bit easier. But look, all this stuff is going to evolve. And so I am excited about a number of things that we've talked about here. And I'm excited about what will come. What has not yet been built. There's a, Chris Dixon talks and Jason does, they're not the only ones who do this,

Starting point is 00:54:34 but talk a lot about kind of we're in this kind of period of like skeuomorphic analogies in Web3 where people are using existing business models from Web 2 and trying to apply Web 3 to that. Just as people did with, he used an example the other day, Chris did, of looking at the first commercials for the iPhone. Steve Jobs and Apple was putting out commercials for the iPhone that revolved around using the iPhone to look up recipes in the kitchen. And like, that couldn't be a less important use of the iPhone today. But people were trying to use what they knew about the world to predict how people would use the technology.

Starting point is 00:55:13 I think we're in that phase for Web3 today. So what I look at is that fundamentally this technology allows for new things. How the technology will be used, I'm not sure, frankly. And I don't think that there's, I haven't heard many people talk that sound like they know, but I'm incredibly interested in how value will be unlocked through Web 3. What you're talking about sounds a lot like stuff you can't learn in business school necessarily, although I know Stanford and some others are pioneering Dow education, and a lot of stuff already.

Starting point is 00:55:44 But it just reminds me of what you've learned, having come out of Stanford Business School, that you probably didn't find in school, Meaning, are there any other resources, maybe even investing books that you have found made a big impact on your career so far and might be beneficial for those listening today? I think the intelligent investor is just, you know, if you're going to be an investor, I think you have to read that book, even if you're a VC investor. I think it's just such a fantastic book.

Starting point is 00:56:13 I think, you know, a number of books that lay out like Warren Buffett's annual letters, I think are really good. I tend to, as an investor, even really like a lot of the books about entrepreneurship to understand or being a CEO to understand the mind of a CEO and how to build businesses in a healthy and enduring way and to create empathy for the CEO. Hard thing about hard things by Ben Horowitz, Zero One, Peter Thiel are great books. But like what I've learned over the last 10 years is I and I read a lot, both books, blogs. I am a bigger fan of what you can get online right now than most books, particularly

Starting point is 00:56:49 investing books. Like I think, people might laugh at this, but I think Twitter is a hell of a resource for understanding investing. That's a dangerous one, because there's a lot of people spouting off that have no idea what they're talking about. You know, blogs from world-class investors, annual reports from a number of different public market investors, I think are really good. Books, you know, that take three years to write and tend to be watered down by editors to appeal to the airport, convenience store crowd. I just don't think that's usually not as. good. So I found a lot more value from some of the blogs I've mentioned and some other sources like that. One question, just circling back to accredited investors, does something

Starting point is 00:57:29 like a Dow, is part of the appeal, this idea that we are kind of breaking that tradition of having accredited investors only benefiting from great opportunities? Does this help equalize in any way in that regard? I think it should. I think there's a lot to get sort of out. We just talked about people not totally understanding whether or not they're getting a piece of the Constitution. And again, I'm not familiar with that. There's danger to that. And I don't actually believe that accredited investors are more sophisticated than accredited investors, but they certainly can afford to lose the money more so than most of our credit investors. And so I think we need, the market needs to mature, but I think that there is potential for some of these new

Starting point is 00:58:08 structured, particularly DAOs, to help on accredited investors participate. In your next venture, do you think it will be fintech related? I don't know. I like FinTech. I just been investing in FinTech. It'll be technology related. It'll definitely be technology related. I'm a technology operator. But it doesn't have to be FinTech. I think there's a lot of different fields. My wife's the CMO at Coursera, the NGT8 tech company. Ed Tech interests me, healthcare interests me, particularly mental health. FinTech interests me, B2B or BTC. There's a lot of things that I get excited about. I just think we live in such an exciting time. I mean, in the course of human history, when has there ever been as much innovation in a

Starting point is 00:58:46 a 10, 20-year span as what we're seeing right now. You know, you look at the gold rush in 1840 years or so, look at the Renaissance in Italy, but like the innovation that's happening right now is so incredible. So to be able, you as a founder know this, like to be able to participate and try and build something right now, God, what a gift to be able to talk to our kids and our grandkids about that in 30, 40 years. I don't know how long this period of innovation will last. I hope it lasts for a long time, but like, I just feel so lucky to be building right now versus 50 years ago. Yeah, there seems to be this feeling, this acceleration happening. I think that's what we're all trying to process is just how fast things are only

Starting point is 00:59:20 compounding and getting faster and we're just trying to like stay up to speed and then it's dated all of a sudden. And it does make it very exciting, but also just overwhelming sometimes as well, at least in my experience. Before I let you go, I want to make sure I give you the opportunity to hand off to our audience where they can follow along with what you're doing, where they can learn more about you or any other resources you want to share. So on Twitter, it's just Ryan underscore Caldbeck and my website where I post a lot of blogs is Ryancauldsbeck.com. Ryan, this has been so great. I really love this discussion and I really admire what you've built and the way you've approached

Starting point is 00:59:59 it. And I'm really excited to stay in touch and see what this next venture looks like for you. And thanks for coming on the show. Thank you so much for having me. All right, everybody. That's all we had for you. This time, if you're loving the show, don't forget to follow us on your favorite podcast app.

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Starting point is 01:00:31 and then compare it to your own. Just Google TIP Finance. It should pop right up and enjoy. And with that, we'll see you again next time. Thank you for listening to TIP. Make sure to subscribe to millennial investing by the Investors Podcast Network and learn how to achieve financial independence. To access our show notes, transcripts or courses, go to theinvestorspodcast.com.

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We Study Billionaires - The Investor’s Podcast Network - TIP405: The Future of Fintech w/ Ryan Caldbeck

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