Democratizing Venture Capital Investing

[00:04:27] Kjael Skaalerud: Got it. Part of my role, I guess, in this conversation will be to strip it down for the folks who aren’t quite as familiar with our category. Cause I know that’s a large chunk of our audience. So if I’m a retail investor today, let’s say my friend has a tech company and there’s a connection there, right?

[00:04:44] Which is not always available. And he’s raising money and they’re taking money from friends and family. I might have an opportunity to invite you personally in that business. And I know that there are accreditation components around that as well, accreditation, meaning I need to prove a certain net worth of a certain amount of income to actually be a candidate for that investment.

[00:05:03] But then there comes the actual diligence. How do I achieve a level of competence, even though he’s my buddy, right? And I trust him as an operator. How do I lack the industry acumen, perhaps I’m not quite as familiar with finance to actually evaluate that investment and say, okay, this is a good or a bad investment.

[00:05:19] And then let alone think about how it fits into my broader portfolio. Right? I’ve got a 401k that’s invested in some stuff. Maybe I have a personal stock portfolio. I probably definitely have a crypto wallet of some kind. So there’s that component, right? So I can invest directly into it. And then on the other side, I can try to take a position.

[00:05:35] So to avoid the big gap that I just explained in the actual diligence and execution, the next thing to do would be okay, I want to invest in a professional that does these types of venture investments for living, and to do that, I would need to invest in a fund. And typically the big hurdle there or constraint is the amount of capital that you bring to the table.

[00:05:57] Right? So it can’t be like, Hey buddy, I’m comfortable giving you a 10, 15, 20, you know, whatever it is. K. Cause I believe in you and we go way back. Now I want to invest in a fund and they’re going to say cool, A, there are no spots because everybody wants to invest in our fund, and B, if there’s any chance we can get you a spot, we’re going to need a $10 million check. Is that an accurate statement?

[00:06:17] Matthew Klein: A hundred percent, you nailed it. And that’s been the gate, right? And the average everyday investor hasn’t had access to this asset class. And when we look at the modern-day portfolio, we see a lot of evolution and the democratizing of Alternative assets, be it art with masterworks, be it what Titans is doing kind of in the hedge fund public space. Obviously what Robinhood has done for micro-investing, and many more. We believe that venture capital is kind of this untouched space that nobody’s really gone after.

[00:06:51] And here’s the thing, the average everyday person, isn’t going to bed at night saying, Hey, I want to invest in VC, but I can’t. But as soon as you explain to them what the historical returns look like and where a lot of the money pre IPO is being made by traditional BCS, it’s definitely an eye-opener, and retail investors want access.

[00:07:13] We’re seeing it firsthand in the responses we’re getting from our waitlist and early adopters. And what we’re hearing in the market, just in general. I mean, it’s pretty crazy. What was it like, earlier this year with Game Stop and Redditt and the kind of that whole movement?

[00:07:30] I mean, that was really a huge catalyst and a turning point, I think with retail investors, where they really kind of woke up and were like, hey, we want access. And we’re going to play this game too. And that kind of, noise and that momentum hasn’t slowed down. Now, I don’t believe in investing in meme stocks and you know, trying to get rich quick by any means.

[00:07:54] But I think the important things that came out of that are the fact that retail wants access. So let’s give them responsible ways to invest, and the cool thing about Sweaters is it’s not a get rich quick type of opportunity. You’re not day trading here. You’re not buying and selling.

[00:08:13] You’re investing in a VC fund. That’s deploying that capital and it’s a long-term investing strategy. And we’re really clear with our members, which are Sweater investors, that this takes time. It can take upwards of 5, 7, 10 years for these unicorns to grow into the great technology companies that they are.

[00:08:36] Kjael Skaalerud: So I got, and I totally agree that there’s definitely a cultural swell that’s occurring, where the average person’s financial acumen is night and day from what it was, even two or three years ago, they’re talking about, oh, you know, I’m trying options. Whoa. That’s a pretty sophisticated thing to approach.

[00:08:56] So I totally agree. And that’s an amazing tailwind for what you’re up to when it comes to the concept of precedent. Right. I know that there have been some issues. Spaces and in alternative investing, which we can loosely define as not stocks, not bond stuff, that’s not liquid on an exchange.

[00:09:15] So real estate assets, private companies, of course, commodities, to a certain extent. Real estate has been a category that’s kind of been democratized. You have things like evergreen funds that are publicly traded where you’re kind of buying a share of something on an exchange that gives you access to a private capital markets thing.

[00:09:35] That’s kind of rooted in alternative investments. So is there a wake that you see or is there kind of a trail that you’re trying to follow? And if so, who are some of the groups that have spearheaded, those, like stuff that you’re excited about?

[00:09:48] Matthew Klein: Yeah, definitely. I mean, Cadre is doing a great job in the real estate space.

[00:09:52] There are a few other folks that play in that space. I like to think of this modern-day portfolio that’s made up of crypto, NFTs to a certain degree. You know, if that’s something you’re into and then you know, Titan, Masterworks, Cadre, Robinhood, Wealth Front, Betterment, some of the modern broker-dealers as well that are offering different funds.

[00:10:15] So there’s a new way of investing. I mean, we’re literally in the middle of a financial, FinTech revolution. And I think things are just changing the way that we think about money, the way we think about investing and kind of building this shorter-term liquidity strategy mixed in with a longer-term strategy, which gives opportunities for companies like Sweater to be able to go and build out a fund that could show returns to folks down the line in the future.

[00:10:48] Kjael Skaalerud: Cool. And I guess in terms of your approach, so you had mentioned there’s going to be some direct investing. You’re going to be able to co-invest with some of the more established VCs, I guess. Can you tell us a little bit about your priorities and what you think is going to be really critical to success?

[00:11:04] Obviously, the traditional, tent or poles in the tent, you might say of a venture firm are, deal origination and access. As you had mentioned diligence, and actually underwriting these and then, of course, visibility into the performance over time. So how are you thinking about the key areas of execution for Sweater?

[00:11:25] Matthew Klein: Yeah, definitely. That’s a great question. So the way that we look at our deal flow is a multi-phased approach. So we co-invest alongside traditional venture funds. Sweater Inc is a venture-backed company as well. We just raised $12 million with Akuna Capital, and motivate a bunch of other amazing super angels that were in that round.

[00:11:41] So we’ll co-invest alongside the investors that have invested in Sweater, Inc. We’re also building out a co-investing strategy. We have 25 plus co-investing partners now that we’re looking at deals with.

[00:12:01] We’ll write checks in some of those funds, actually, as we can take part of our total assets under management and the fund, we can actually deploy as LP positions in funds and that helps us strengthen some of those partnerships. So we’re co-investing, we’ve built out a deal scout team. We have over a hundred scouts now across the country.

[00:12:22] These are folks that work at other VC funds, work in private and public markets, the banking and FinTech industry, and across multiple industries. We’re getting a ton of deal flow from this scout network. It’s really exciting. And it’s really kind of flipping things on the head for us.

[00:12:40] So really pumped about that. And then we’ll be leading deals as well. I mean, we’re kind of in the mix. Our investment team has a lot of experience, myself, Jesse, and Chad have a bunch of relationships that we’re bringing to the table. So we feel really great about the overall deal flow that we’ll be bringing in.

[00:13:00] Kjael Skaalerud: That’s awesome. It’s interesting too. Cause at Altvia, you know, we interact with tons of GPS and their customer is an LP, right? So most LPs are institutional groups, pension funds that have tremendous capital that they need to allocate, you have family offices as kind of a distant second, which are representing typically the wealth of an individual that’s managed by a team, and then you have high net worth individuals.

[00:13:26] And then below that would be retail. Right. And up until this, privates, private equity, venture capital. That’s been available to institutional family offices and high net worth. And if you look at kind of the experience, and we’re all kind of being conditioned, behaviorally by the technology that’s around us.

[00:13:43] Right? So Facebook, Instagram, WhatsApp, Spotify, whatever. It’s on our phone. It’s real-time. We’re looking at our portfolio on Robinhood, right? We’re literally walking to lunch, pulling it up on our phone, getting real-time visibility. And so that’s kind of the status quo or just general expectations for humans nowadays.

[00:14:04] And if you contrast that with privates, it’s usually a situation where, hey, I gave you $10 million, be it on an institution or a family office or whatever. And I give you a buzz to see how the portfolio is doing. And most of the updates come in a PDF format. I get them on a quarterly basis. Most of the time it’s a quarter and a rear.

[00:14:23] So there’s kind of a six-month lag to actually understand where things are at, and then what typical consumers are expecting. So I can in terms of pillars and as you think about experience, how are you thinking about transparency? How are you thinking about mobile?

[00:14:42] And also as a huge point of differentiation, cause selfishly, why I’m so excited about Sweater is it’s going to continue to pressure the old kind of legacy status quo, where it’s like, hey, I’m not signing into a glorified Dropbox to look at a PDF. I want a mobile app now that I can look at. So how’s that stuff kind of introducing to you?

[00:15:02] Matthew Klein: For sure. And then, being the Chief Experience Officer, this is definitely the world I live in, right. Every single day. So the entire experience is mobile-based, right? So you’ll download the mobile app and our thesis is: We want to give everyday investors, literally courtside seats to the game.

[00:15:18] We want them to be able to go into the locker room, meet the players, sweep the floor, truly introduce them to the world of venture and give them as much transparency as we can into what we’re doing. So, we’ll do all of this through the mobile app experience. 

[00:15:35] So this is definitely something where the everyday investor, after they download the app, become a Sweater member, make their first investment, they’ll have access to what companies sweaters, investing into. You’ll be able to download and read information, see interviews with founders, understand why Sweaters investment team decided to make an investment.

[00:15:52] What do we believe in that company? That founding team, what is their mission and vision? What do we like about those certain markets? So all this content will live in the app. We are also really big on education. We know that a lot of folks in retail don’t necessarily know about VC.

[00:16:10] So it’s our job when we feel like we can truly become the thought leader to teach them about the world of venture. So we’ll have an area in the app called venture 101 where you’ll be able to go through and learn the world of venture. Everything from, what is a term sheet, what does it mean to be a series seed company moving to A, B, C, what is an IPO, what’s pre IPO?

[00:16:30] What are all of these different kinds of aspects in the world of venture? And that way we can educate our investors along the way. So a lot of content is really key here, and transparency is very important to Sweater and really building trust with our members.

[00:16:49] Kjael Skaalerud: Put an exclamation point on that.

[00:16:50] That’s a level of visibility that is completely uncommon and privates today, right? Like a GP would never see an investment memo that details why they’re making this investment or know the nuances of the elements of a term sheet. So that’s like lifting all the way up.

[00:17:07] Matthew Klein: Yeah. You know, one thing I’ll add, and I know that there are GPs and investors that will be seeing this, as well as everyday folks. A big thing for us is we want to give retail a seat at the table. So by no means, are we trying to kick people out and change venture forever.

[00:17:29] It’s really just about giving access to folks in retail. But one thing we do believe, especially with early-stage companies is that when you go to raise that next round of funding over the next 12 to 18 months, you’re going to look at your cap table and you’re going to say which retail VC do we want?

[00:17:49] On our cap table, because Sweater knows it’s gonna have competition. You know, Kathy just logged arc is launching a later stage fund. There are going to be other folks that come into this space. So the idea that founders will want retail money I think is happening. And I think it’s a good thing for the market to give them that access. 

[00:18:09] Kjael Skaalerud: Totally. This might be a good time to kind of shift gears because I think many would say that there’s not very loud spoken, but kind of universally acknowledged thesis that public markets are more evolved, right? Like they’re more liquid, they’re more transparent. But they’re also more regulated and other things like that, but the thesis then would be that, okay, public markets or private markets today are a little bit behind.

[00:18:36] And so that gap, that Delta, will be closed over time. And it’s totally in line where it’s the same in the commentary that you just shared where you’re looking at a quarterly earnings document or some type of disclosure because that’s how public markets operate. And the fact that privates don’t, because they haven’t quite gotten there, but that’s still an expectation and kind of an inevitability right, in the internet era.

[00:19:02] People can find information if they want it, no matter what. Even by illegal means, they can get access to financial statements to understand how a company is performing and things like that. But I guess, do you believe that as well, that public market, there’s a Delta there that will be closed over time, and that things will get to a place where it’s totally liquid transparent?

[00:19:21] Matthew Klein: Yeah. That’s interesting. I mean, my personal opinion on the matter is that I think transparency is good for the market. I know that there’s been like you said, a lack of transparency in private markets. I think that gap is closing. I think it needs to in order to create further liquidity options for private markets. 

[00:19:46] As a society, we’re getting much more comfortable with private opportunities having the type of valuation where there are liquidity options around that. You’re seeing it with Web 3, you’re seeing it in Crypto. You’re seeing what Carta is doing in the secondary market for employees that work for tech companies and whatnot that have stock options and things like that.

[00:20:07] That’s definitely happening, and in order for that to happen, there needs to be more transparency into the underlying asset. So that’s just inevitable.

[00:20:15] Kjael Skaalerud: And that’s an interesting piece too because I guess another component of privates or venture are the employees that have options and have shares in these private companies.

[00:20:26] And they don’t really have any access to liquidity, right? They can’t monetize those positions until a new venture round happens or an IPO, but there are still valuations of those businesses that are occurring over time. So you can say, hey, I was given this piece of paper that was worth 10 cents when I got it based on what the book is worth.

[00:20:45] My piece of paper is worth a couple thousand dollars. I would love to take advantage of that, right? That’s this whole other cohort that’s there. And as you mentioned, there are folks that are going after that. And then there’s this element where companies are staying private longer.

[00:20:59] And there are some arguments around that, but you know, 10 years ago you didn’t see a series G round for $10 billion, that company would have IPO’d. Right. Which would have been a liquidity event. The employees would have taken some chips off the table, so to speak, the public market would have gotten involved.

[00:21:13] So I think that fits in neatly.

[00:21:15] Matthew Klein: And that’s a really good point and that’s something we could have a healthy debate on. And just talk about in a whole other session, is this private to public market transition. It’s not always smooth and it’s causing a lot more companies right now to stay private longer.

[00:21:29] Like you said, raising, you know, series G, like much later stage.

[00:21:36] Kjael Skaalerud: It’s probably like you run out of alphabet letters.

[00:21:38] Matthew Klein: Yeah, I think a trend that we’ll start to see over time as more retail investors get comfortable with private markets, and private markets have further liquidity options.

[00:21:51] I think you’ll see a smoother transition over time. And it’ll be interesting to see what that does to the IPO market. You know, if folks are able to invest in earlier stage. Here’s the question I would say is, what happened over the course of the next decade, if the average everyday investor now has opportunities to invest in the earliest stages of a company is an IPO?

[00:22:16] That’s something they’re going to be that interested in. 

[00:22:21] Kjael Skaalerud: If it even exists, right? Yeah. There will no longer be a distinction between public and private. It’ll just be some type of container around ownership. The assumption around the value and then a marketplace to kind of transact buyers and sellers.

[00:22:37] Matthew Klein: Exactly. So it’s really interesting.

[00:22:39] Kjael Skaalerud: It is. It’s an interesting time to be alive as it relates to capital. You know, there are just so many macro trends that are converging. Cool. So I guess another question for you. So it sounds like up until this point, and I know that we’ve kind of covered a lot of ground, just kind of baked into that conversation.

[00:22:56] I was hoping to get your perspective on the guiding light and what’s been happening in other elements, like real estate and evergreen funds and things like that, kind of the timing, right. This is a very common question during venture diligence, you know, product-market team, why now?

[00:23:14] I think we touched on why now and that you’ve navigated some of the regulatory elements and that you’re feeling good and moving forward with. We touched a little bit on the bets or like your view on where the category more broadly is going to be moving and perhaps a little bit on how the incumbents will respond, but I just want to verify how you’re thinking about that.

[00:23:36] Because there is an incumbent in this situation. Right. And it sounded up until this point and correct me if I’m wrong, that you think that the established venture groups now are going to have a mostly positive reaction to this and that we have an opportunity to bring more capital to the table, which will generate more innovation, more economic productivity.

[00:23:55] The founder operators will kind of embrace it as well because they want to appeal to retail, both as consumers of their product, and just in the interest of transparency of what they’re up to. Are you feeling that it’s going to be pretty well received or do you think anybody’s going to fight you here?

[00:24:11] Matthew Klein: Yeah. you summed it up really well. Overall that’s how we feel. I think at the end of the day, of course, I’m sure we’ll have folks that feel like we’re quote-unquote, stepping on their toes, or coming into their space, but that’s not our agenda.

[00:24:24] Our agenda is really just to further open up access to everybody. So sure, we may be met with some folks who are anti what we’re doing, but I think there are enough folks that are excited about what we’re doing, that we can navigate those waters. Also at the end of the day, this is happening.

[00:24:45] Like whether its Sweater who knocks it out of the park here, knock on wood. Like we feel really good about it or somebody else. Retail is coming into this space so, it’s more of let’s create a bigger table where everybody can sit at and let’s not kind of get hung up on, sure there’s an element of like beat him on the course.

[00:25:05] I mean, traditional venture funds are fighting for deal flow as it is today. So I can understand where some folks are, from the incumbents kind of saying, wow, this is just another person who’s coming into our space and our deal flow. But overall, I think we’re getting really positive results.

[00:25:24] People see it happening and want to be a part of it. What side of the story do you want to be on with retail? You know, I think most folks kind of want to be on the right side, which is let’s give retail access to this gated asset class that has only been for a select few over the past several decades.

[00:25:48] Kjael Skaalerud: For sure by way of metaphor, the tide is coming in, you can move your beach chair or not.

[00:25:56] And that’s your point? The main point of focus is obviously serving again, the customer kind of the Amazon approach and then competing in the space, right. Competing for access to good investments versus fear of, how is this disrupting the mechanics? Because to your point, yes it’s less about how the sausage gets made and more that you’re bringing back the best sausage.

[00:26:17] Matthew Klein: Exactly.

[00:26:19] Kjael Skaalerud: All right, so if it’s cool, we’ll kind of shift gears and perhaps get a little more personal. I find it. It’s always amazing, especially with leaders, such as yourself to get in your head a little bit. So with that, is there a book that you have given away the most often, or that would be your most highly recommended?

[00:26:35] Matthew Klein: Yeah, definitely James Clear – Atomic Habits, I think is my number one book that I both love and would give out and have given out. I think the way he breaks down kind of building a building these habits through micro habits is just awesome.

[00:26:52] Kjael Skaalerud: I subscribed to that, like to the bone.

[00:26:54] It’s the old, show me your habits and I’ll tell you your future. And it just goes on and on defined by our rituals. Personally, that’s something that I lean into in interviews even, you know, just tell me about your most important rituals. And if you get cross-eyed okay, next question.

[00:27:11] And then that usually does it for me just on how that person approaches life, and just the notion of habit stacking and stuff like that. So I’m totally with you. I’m trying to think too of offshoots of Atomic Habits. There’s definitely some thinking there and Ray Dalio’s principles, which is adjacently associated.

[00:27:28] And for those that find Atomic Habits interesting, and other books, Triggers is pretty interesting too, which has definitely touched on and by James and he has a really good blog too. Cool. All right. One more for you. If you could have one thing on a billboard, so imagine, everybody has to drive down the same street on their way to work.

[00:27:45] And there’s a billboard that gets eyes from the world. What would you put on it?

[00:27:50] Matthew Klein: Yeah. Put one foot in front of the other. I mean, at the end of the day, when you talk about challenges, when you talk about opportunities, when you look at whether it’s starting businesses, families, whatever it is that you’re doing in life can feel so massive and kind of just unapproachable, but at the end of the day, the only way is to start taking those steps. 

[00:28:09] And by taking steps, you’ve got to put one foot in front of the other. And when you put those steps together, that’s when you start making progress and that progress turns into momentum and that momentum is what helps get you to your goal, get you to that next inflection point.

[00:28:29] So that’s a big thing. I mean, just like anything can seem monumental, but if you just put one foot in front of the other and start taking those steps you’re on your way.

[00:28:39] Kjael Skaalerud: So totally agree. When I was a kiddo, I used to just project so far out into the future, and then you just get speaking, find yourself in those kinds of tailspin moments, right.

[00:28:47] My mom used to say, how do you eat an elephant honey? And the first time I looked at it, like, how does anyone need an elephant? Like one by one. One bite at a time, one bite at a time.

[00:28:58] And then there’s an interesting element too, which kind of ties back to Atomic Habits of the notion of compounding effort and that being one of them, I can’t remember Warren Buffet calls it like the eighth miracle, the world compounding interest, but it’s the same application in everyday life.

[00:29:14] Just get 1% smarter, 1% stronger, whatever it is. Cool. That’s it. That’s it. That’s where the big returns are. Right. Back to probably the topic at hand here in general, is this generating exciting returns and then bringing in access to opportunity and economic prosperity. So that’s all very good. Well, I think we can go ahead and wrap that sound.

[00:29:36] All right.

[00:29:37] Matthew Klein: Cool, man. Well, thanks for having me on the podcast. This was awesome. And hopefully, everybody likes the story, and if you haven’t already definitely sign up for the waitlist. Go to sweaterventures.com to learn more.

[00:29:48] Kjael Skaalerud: Yeah, outstanding. Awesome. Well, thank you again, sincerely for hopping in here and spending time with us, and for the record, I’m on the waitlist.

[00:29:56] The updates are amazing and stay close to Sweater Ventures. They’re going to do some exciting stuff.