Reddit’s IPO, Consumer vs. Enterprise AI, and Sam Altman’s New Fund and more! | E1903

23 Feb 2024 · 1 h 12 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

This Week in Startups - Episode E1903 Summary

Episode Overview Episode Title: Reddit’s IPO, Consumer vs. Enterprise AI, and Sam Altman’s New Fund and more! Host: David Weisburd Guests: Bryan Rosenblatt, Michael Downing, Jason Calacanis Timestamp: Released on [Insert Release Date]

In this episode, host David Weisburd engages with guests Bryan Rosenblatt and Michael Downing, alongside entrepreneur and investor Jason Calacanis. The discussion centers around Reddit's Initial Public Offering (IPO), distinctions between consumer and enterprise AI, and the implications of Sam Altman's new venture fund, among other topics pertinent to the startup ecosystem.

Key Discussions

  1. Reddit's IPO
  2. Revenue Insights:
  3. Reddit has reported over $804 million in revenue.
  4. Transition from Small Platform to Advertising Powerhouse:
  5. Bryan shares his insights from working at Reddit during its formative years (2015-2019).
  6. Original revenue was less than $10 million, highlighting significant growth.
  • Challenges in Advertising:
  • Discusses the skepticism advertisers had towards Reddit due to its complex user base and brand safety concerns.
  • The panel mentions the evolution of Reddit’s advertising strategy, emphasizing the need for tailored ads rather than generic campaigns.
  • Longevity and Community Engagement:
  • Jason notes that Reddit’s success stems from its consistent focus on community building and user engagement, contrasting it with competitors that tried to innovate too aggressively.
  1. Consumer vs. Enterprise AI
  2. Integration in Businesses:
  3. Conversations about how businesses adopt AI, particularly in understanding the nuances between consumer-focused AI products versus enterprise applications.
  • Market Trends:
  • Michael Downing emphasizes the rapid growth of AI companies.
  • Bryan points out that many emerging AI companies are built by operators with deep domain expertise, leading to innovative solutions.
  • Investment Strategies:
  • Discussion about the structure of AI investments and the importance of technical know-how in early-stage startups.
  • The panel agrees that enterprise AI often has a clearer path to profitability compared to consumer AI.
  1. Sam Altman’s New Fund
  2. OpenAI’s Investment Strategy:
  3. Bryan highlights that OpenAI’s fund has invested $175 million in various startups, providing them with unique insights into emerging technologies.
  • Pros and Cons of Corporate Venture Capital:
  • Michael discusses the potential benefits and pitfalls of involving corporate VCs early in a startup's lifecycle, emphasizing strategic alignment versus operational control.
  1. Investment Strategies and Market Dynamics
  2. Portfolio Construction:
  3. Bryan describes Craft Ventures' flexible approach to investment based on market conditions.
  4. Jason discusses the significance of understanding economic cycles and their impact on fundraising.
  • Raising Capital in the Current Environment:
  • Panelists offer insights into how startups should approach fundraising—balancing between raising sufficient capital without overextending.
  1. Rapid Fire Segment on Recent Investments
  2. Recent Investments:
  3. Bryan shares investments in health tech (Solace Health), an ad tech platform (Agentio), and a venture fund (Alt Capital).
  4. Michael discusses investments in emerging funds focused on unique niches, particularly in defense tech and innovative startups.

Key Takeaways

  • Reddit's Growth Story: Highlighting the transition from a small advertising player to a significant revenue-generating platform illustrates the power of community and user education.
  • AI Investment Landscape: Understanding the distinctions between consumer and enterprise AI is crucial for strategic investment, with enterprise showing more promise in the near term.
  • Role of Corporate VCs: While corporate venture capital can provide validation and strategic advantages, startups must navigate the complexities these partnerships introduce.
  • Market Dynamics in Fundraising: The current economic landscape influences how startups approach funding, focusing on sustainability rather than merely chasing valuations.

Mentioned Links

  • [Northwest Registered Agent](https://www.northwestregisteredagent.com/twist)
  • [DevSquad](http://devsquad.com/twist)
  • [Miro](https://miro.com/startups)

Conclusion This episode provides a deep dive into current trends in the startup ecosystem, especially in AI and media, while also shedding light on investment strategies that adapt to changing market conditions. The insights from experienced founders and investors offer valuable perspectives for those navigating the startup landscape.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00If you take the entirety of unicorn successful companies that have come out of the market over the last 15 years 92 % of those companies had a small funds with a small fund that success of company.

0:20Yes. Almost none. Almost none. Less than 5 % of the time did they ever even participate beyond the C-Sage, which is just, you know, I mean, with some of these companies, it's hard to imagine the value. This Week in Startups is brought to you by Northwest Registered Agent will form your company fast, give you the documents you need to open a business bank account and more. Visit northwestregisteredagent.com slash twist to get a 60 % discount on your next LLC. DevSquad. Most dev agencies only offer developers. Why? Because product management is hard. Get an entire product team for the cost of one US developer plus 10 % off at devsquad.com slash twist.

1:06And Miro helps take ideas from in your head to out there in the world. with its ability to democratize collaboration and input. Sign up for free at Miro.com slash startups. Welcome back to this week's Liquidity Podcast. With me today, I have Brian Rosenblatt of Kraft Ventures, a VC firm founded by Jason Earbesti, David Sachs, which now has over 3 billion AUM. Next, we have Michael Downing of MDSV Capital, emerging manager focused fund of funds that also has a direct investment fund providing managers with follow-on capital. and of course we have jason galagianis from the launch fund i'm your moderator david weisberg co founder of 10x capital today we have a busy episode we have first off reddit officially announced it's going public how companies are using ai there's a new corporate vc in town and family offices are stepping in to fill the void left by many institutional lps and we'll close out with our special segment where we look at the panel's latest investments Let's dive right in.

2:09Reddit officially announced that it's going public via their S1 filings on Thursday. In their filings, Reddit announced that it has over$804 million in revenue. Brian, you actually worked at Reddit for three and a half years between 2015-2019. What was your experience working at Reddit and are you still bullish on the company? Yeah, I mean, I'm incredibly bullish. I was there in 2015, the time Alexis Ohanian had just come back to the company as a chairman. And Ellen Powell was interim CEO. So I joined. It was a small team. The business was tiny. They were doing less than$10 million in revenue.

2:48And it was a wild ride, obviously, the number cited today. But it's an incredible platform. Back then, advertisers did not know how to work with Reddit. It was sort of the wild, wild west. It was scary and dangerous. There were advertisers that would laugh us out of the room. And some of those advertisers are now spending millions of dollars. So incredibly bullish for kind of what's ahead for them. Brian, how did Reddit cross that chasm from being a small$10 million advertising platform to the behemoth that is today? Yeah, I mean, there's a lot that went into it. First and foremost, it was education.

3:24There are so many passionate users on Reddit and communities, but there's a lot of people that it scared off. It was hard to use. And so it took a lot of education because the people that were buying the ads may not be the exact Reddit user. So there was a lot of education of why Reddit, how Reddit, how it compares to other platforms. There was a lot of hesitations around brand safety. We shipped a ton of features to kind of answer those concerns. And we changed the product a lot. We didn't have our own native mobile app. We shipped that. We did a complete redesign of Reddit to make it more user-friendly.

4:01And so a lot of work on the product side, but also in just kind of general education. You're one of these VCs that came from the product side. There's many different flavors of VCs. What advantages and disadvantages are there to going from company side, from startup experience? Yeah, I mean, I think there's a lot. I really came from the sales side. And as a salesperson at Reddit and Twitter, I would have to identify companies that were growing and that would be good targets to kind of spend time with and sell advertising to. And so early on, I was always picking companies that I thought would get bigger and have bigger ad budgets and then develop relationships with kind of those advertisers and marketers.

4:42And I think that crosses over really well into VC, which is also a big relationship business, spotting talented founders, building relationships, winning deals, negotiating. And then also just having empathy around the process of building. As an operator, there's just so much that goes on, good and bad, and it's a roller coaster and the frustrations. And I think when talking to a founder and their team, being able to just understand what that actually means goes a long way versus someone who's only been on the investor side of things. And Jason, you've been around Reddit for quite a while. You guys started kind of in the alternative media space back in the 2000s.

5:25What have you seen and what are your views on Reddit's future? Well, it's incredible. I had Alexis Ohanian on This Week in Startups just a week or two ago talking about the IPO. know, it's just amazing that it survived this long, right? There's something about longevity on the internet. If you remember, there was dig, which was a much fancier Silicon Valley based product, as opposed to this Boston based YC quirky Reddit site, both started at the same time. But dig tried to change their interface, they had this big artificial intelligence machine learning concept early on that they were going to give everybody their own unique homepage, they tried to do what Facebook was doing.

6:01And Reddit didn't change. And Reddit just slowly built community and now i think community has been very hard for people to monetize um it's one thing to have a social network and a feed like twitter x you know tiktok etc but but a dedicated forum and community it was really hard um to actually get one of those to scale and the numbers are amazing you know like almost 100 million people use it every day you have 500 million people using it every month it's it's not throwing off as much advertising revenue as it probably should 800 million, I think, was what they made last year. Because it is challenging.

6:36Advertisers in forums are going to contend with the good and the bad, right? And one of the things that's happened over this rotating set of CEOs, they had, remember they had Alan Powell for a minute. But of course, they got the co-founder to come in and take over the CEO slot, which was great. You know, it's just amazing what you can do if you don't change the interface and you just let something be and you let it grow slowly um now if you were to look at the amount of advertising revenue you know they have less revenue than say uber now has i think uber's at a billion right now is their run rate um and so it's very tiny but it's very influential so that's the thing to keep in mind this is an influential audience you can tell it's an influential audience because when people type in you know some product review or they want a piece of advice, they'll append to their Google search the word Reddit.

7:30Now users don't know like how to use site Reddit or they don't go search on Reddit, they just go to Google, they type it, they search it shows you how strong it is. And if you look at interfaces that have not changed, and how big companies have become, Craigslist, Amazon, and Reddit are the top three that just did not change their interface, and just let it grow organically. So there's a lot to be said for longevity there. Now, the investors, this company was sold once in a fire sale kind of situation to Condé Nast, then it was spun out. Famously, I think Sam Altman used his sharp elbows and great negotiating tactics that we've seen to kind of free it and to get a new cap table gung.

8:11So kudos to him for helping the founders do that. I don't know what the company is worth right now as an advertising business. It's probably not very interesting as an advertising business, and it's very hard for somebody to buy it. because to acquire it, you bring all of those challenging subreddits with you, adult content, spicy content. And remember, they use pseudonyms over there. So people can be anonymous, basically. But what's most interesting is the data. And it was just revealed that they're making, I think,$60 million from Google. And I believe that's a yearly deal. Now, I wonder if there's 10 more deals like that to be had.

8:45And then the$800 million in revenue could be paired with 800 million in licensing data, right? And I think eventually somebody might just buy this thing, like they should buy Stack Overflow or other sites on the internet, Quora, just to let them sit, let them grow, let them service their users, but to feed language models. So I'm kind of shocked that it didn't get bought and that it is IPOing. But sometimes companies will do an IPO in order to force the market's hand, right? They just clean up the cap table. Now it's public. You get price discovery. And then maybe somebody does want to buy it or somebody wants to buy 10 or 20 % of it.

9:22So congratulations to the team over there. Congratulations to the community. I think it's a real testament to the community more than anything. Starting a business used to be a pain. You needed a lawyer. There were hidden fees. It was a mess. Now with Northwest's registered agent, it only takes 10 clicks and 10 minutes. Northwest provides everything you need to start and maintain your business. Every LLC, corporation, or nonprofit at Northwest Forms comes equipped with registered agent service, a business address, a website and hosting, email, a phone number, and this is all covered by Northwest's privacy by default.

9:59Again, your full business identity will be live in 10 minutes and in 10 clicks. So here's your call to action. for$39 plus state fees, they'll form your LLC, corporation, or nonprofit and launch your business in just minutes. Visit northwestregisteredagent.com slash twist today. That's northwestregisteredagent.com slash twist today. Brian, Jason referenced that there were some difficulties with the product in terms of some of the content, but also there's a very different audience, very peculiar. It is Socratic versus other communities. What did you come across when you were selling into advertisers?

10:36I think it's actually, there's a lot of surprises. So I think, you know, you talk about some of the adult content, and maybe people assume like that very nerdy, techie computer programmers that live on Reddit. And that definitely is true. But some of the biggest communities are around like makeup, makeup addiction. And so L 'Oreal and beauty brands are all over that. There's a community called Mommet for moms and Daded for Daded. And so there are these communities that are extremely wholesome. And speaking on the anonymous point, people, unlike these other platforms, people can have really authentic, real conversations when they're not concerned about their neighbor or friend hearing everything that they're thinking.

11:17And so there's a lot of really deep conversations that happen on Reddit that aren't going to happen elsewhere. There's so many subreddits that I think advertisers continuously get really become surprised by how relevant there are, you know, these communities are to their brand. And they get really excited once they get educated about that. And Michael, you've been around, I'm not going to say how long, but you've been around through several market cycles. You've taken a company, you've started a company and then took it public. Like what should the Reddit, how will this transform Reddit as a company being a public company?

11:51Well, I mean, first, to be honest with you, it's like, I'm amazed they're doing 800 a million a year. I mean, that's super impressive for where they've been and just the trials and tribulations that a company's gone through with acquisitions and so on. I think that the bigger challenge here is the backdrop of media and digital media is so tough right now. I mean, I think there was an article that just came out in the last three days that talked about how the publicly traded large media companies are on average down by about 50 % over the last two years. And obviously, this is, you know, a new kind of platform and, you know, different than traditional media.

12:33But I think there's, you know, an advertising or purely advertising based business. It's just a tough time to be to be fighting that fight. And hopefully this training acquisition fee that apparently was$60 million or so from Google, maybe that is a new source of revenue that creates a new layer of opportunity there. But just the overall environment in the ad market is pretty tough at the moment. So it'll be interesting to see how they weather that. Advertising is a scale business these days is what it comes down to. So you just start thinking about the scale. Those are the two major trends in, you know, maybe there's three.

13:14There's scale, there's data, and then there's how close are you to the checkout box. And if you look at those three trends, meta and Google have massive scale. Now TikTok has massive scale. And then you look at the cohorts of Netflix has massive scale and they edit advertising, right? Now you look at the how close are you to the shopping cart? Amazon advertising, Uber advertising, inside the app. you're really and doordash does this as well instacart is an advertising business essentially it seems like instacart doesn't make money or profits at least from delivering groceries it seems like you know the end cap advertising when you're in the instacart app is where they're generating a lot of revenue and so you know reddit doesn't have any of those things doesn't have scale doesn't have the end cap what it does have is influential users and so you know i think when they sell that advertising you know to get a passionate group of people but those people are also cynical and they're not the dopey ad clickers.

14:10One of the secrets of the ad business is there's kind of like dopey, like less sophisticated users in the advertising industry. They have kind of terms for them. I don't remember it, but there are people who are just have a tendency to click a lot of ads. You know, same people might watch a home shopping network or something and buy stuff there. They just like advertising. They like shopping. So like maybe we all don't click on a lot of Google ads or ads in our social media feeds, but those people do the sophisticated Reddit people. I mean, it's hard to get them to click on ads. I think it has to be really well-crafted, creative, etc.

14:44And I think it has to be really targeted. I think you would agree, Brian, right? It has to be like... They're discerning users, right? They're not like Yahoo users or AOL users clicking on every ad. Yeah, it's definitely a platform where it's less of like a copy and paste your Google ad onto Reddit and you're successful, which was a challenge, especially early on, because we have to convince brands not only to spend money on the platform, but to spend the time and energy to develop content and ads that work for Reddit. I do think they've convinced the market to do that now, which has been great.

15:19So I think you are starting to see really interesting, different ads and people taking it seriously. But it took a long time to get to this point. This company would be worth 10 times as much if they just said to the market, we have an ad business, it keeps the lights on. We're building a large language model exclusive to our language model and you can ask Reddit questions and nobody else is allowed to have access to this data, period, full stop. And we're not going to license to anybody. And our LLM is going to be, you know, a great way for you to get answers and they just, you know, put that answer engine when you search there.

15:55and then i think the market street would be really like that story and maybe they put a billion dollars into the ipo for them to buy nvidia servers and gpus and get to work on it seems like maybe they they didn't do that steve maybe just thinks the licensing deal would be better but steve's been very clear that that data is um proprietary and you cannot use it and elon's been very clear about that with x and i think a lot of these people are looking at open crawl they're looking at what open ai did they're looking at what you know microsoft did in collaboration with them and uh what google's doing that that open crawl data set probably has a lot of reddit data in it that is illegally unlicensed in people's models so it's just something to definitely consider um is how much revenue they can make from that too we saw the new york times open ai lawsuit uh how much of a lens do you look at that brian when when looking at ai companies how much is proprietary data driving indicator of value?

16:55The data is so key. I think there's very few companies that have truly, truly unique data at scale. And Reddit is one of those. So that's huge. But when I'm looking at a startup investment, it's a key question. It's like, well, what's the moat? What's the data moat? Why do you have this that someone else can't get? And most of the time, there's not a good answer. Like it's not super unique. But I don't know. one in 10, something like that, there is a good answer for why they have unique access through some sort of partnership or some sort of know-how, or they know this, you know, antiquated industry and have access to this.

17:32And those are absolutely, you know, interesting strategies to invest against. And Michael, you're really, you're really bullish on AI and you invest in a lot of AI only funds. What are you looking for, for early stage funds in terms of AI investments? Yeah, I mean, for us, we think that this is going to develop much the same way in the mid-2000s. You know, when it was mobile and cloud, you had some mobile-specific funds, cloud-focused funds, and then it became clear that that's in everything. And, you know, there kind of ceased to exist, those focused kind of thematic funds. We think the same thing's going to happen here, but for the moment, we do think there's certain folks who have a technical advantage when it comes to AI investments.

18:19And what we've seen is they're typically individuals who were on like ML ops teams for the last five or seven years. And they've got a level of technical expertise that's pretty unique that not only gets them into interesting deals, but also kind of creates a network around them of people who have been doing this for a long time. And so the managers that we've backed that are focusing on AI look like that, a pretty unique technical background. And do you see it like stages, like in crypto, everybody was investing in infrastructure and they have this whole thesis of like three different stages of development.

19:00Do you see the same thing in AI or is it completely different? No, we do. There's kind of the foundational concepts, the infrastructure concepts, and then the many, many apps that are going to get connected. created which has already started um i think open ai said something like there's 70 000 gpt apps or something that have been created but um we're focused in on that infrastructure layer right now because there's there's many opportunities in that category uh we've stayed away from just simple kind of application concepts just because i think as as you guys have discussed before on the pod, there's these extinction events that occur.

19:43If it's any kind of business, it's adjacent to what OpenAI is interested in or any of the other kind of larger companies. And so we've really focused on that infrastructure layer. Brian, how are you playing the game on the field? What is Kraft looking at in the AI space? I mean, we're looking at everything, but it is a crazy game to be playing right now. I was saying this earlier today, like it literally feels like you're driving in the storm and it's you can't really see. It's really hard. And so like what I personally focus on is kind of picking the driver, like focusing on the individual. There's just every single day, every single hour, something changes, completely changes the game.

20:30And so I don't really want to go out and say, this is exactly how I think things are going to go or should be or should be built. I kind of want to go and find the best people, best teams, and just trust them to kind of navigate what's happening. But I think that's what makes this so difficult right now. And so early stage, it's all about the team. And then later stage, we need to see proof. There has to be more than just kind of hype around it. whether you've got an idea or an mvp the next step is to transform it into a fully fledged reliable business that can support a growing customer base and that demands more resources on the product side of course and searching endlessly for a rare developer capable of handling every aspect can be time consuming or you can quickly build a complete product team and start developing and launching your product with our partner dev squad dev squad provides an entire development team brimming with the elite talent from latin america your specialized team will consist of two to six full stack developers technical product manager along with specialists in product strategy ui and ux design devops and q a all collaboratively propelling your sas product towards success quickly form a complete product team align with your time zones and cost 75 less than an equivalent team based in the usa with dev squad you're guaranteed the flexibility of monthly payments without the burden of long-term commitments and the complexities of coordinating a vast network of freelancers.

21:53Choose a team primed for immediate action. Visit devsquad.com slash twist and get 10 % off your engagement. That's devsquad.com slash twist. I think Michael's point is really good. I use the analogy as well, Michael, of mobile and what we all witnessed where when mobile apps came out, that was a chance to displace some incumbents maybe who didn't build a mobile app quickly enough or didn't understand it. Eventually, they all caught up and you know if you use your united app now or your bonvoy app it feels pretty great um but you know it wasn't very good uh you know when mobile apps were first coming out and then what mobile apps would be and how they would monetize change like five times it used to be you would buy an app like a flashlight app for a dollar or two dollars in the app store it was a one-time purchase the app wasn't updated and then they would come out with flashlight two and you would buy it again and it had three new features it wasn't like versions and there wasn't subscriptions and with a company like com.com which we were the first investors in we had put 378 000 into the company um they were charging ten dollars for the app just like everybody else and then they got early access to subscriptions and they changed their model to ten dollars a month uh and consumption went up and when subscriptions came out you know things got you know really really popping and in fact the app store didn't exist in the first iphone nor did gps and so a lot of what we and payments certainly didn't and so it took a while as brian is sort of saying i think that's what's happening brian's right in you know uh ai startups the products like chat gpt gemini as we saw you know this week with all kinds of weird woke you know funny stuff happening on x um that trended the answers are not good and you know verticalized apps can give good answers if you ask it to do something very verticalized, you know, very narrow with a great prompt.

23:41Yeah, maybe you can get close to an actionable, reliable answer. But a lot of these things feel like toys and proof of concepts. So I think we've got three, four or five years of work to do to make these functional apps. So that's something like Robinhood or Uber, you know, those apps, Instacart, DoorDash, etc. It took a while for the sophistication level of the mobile phones to be able to do those kind of apps. It took maybe four or five generations to have something really good on mobile. I think we're in the first generation right now of these AI companies. Now, we're investing in a ton of them.

24:14I'd say more than half the companies we invest in are specifically AI related, and 100 % of them are using AI to build their companies. This is the trend. That much is clear. If you try to do hardware, you missed it. Sorry. NVIDIA is going to run the table. you know uh maybe chmok will do well with grok i suppose he will because he got in seven years ago but you know i don't know how much hardware opportunity there is right now or language model opportunity for that matter i think open source wins that too so i think it's back to the application there i think it's a really good point i mean the one thing we've seen that we feel like has been net new and just very unique to observe out there has been you know because we offer up an opportunity fund to these small emerging managers they bring to us some of their fast growing companies and so we've been able to see just how fast some of these ai companies are growing and to jason's point earlier about the companies themselves are using ai products i mean what we've seen is like very small teams i mean in one case right now like a 16 person company that's doing over 20 million in ARR, which, you know, and they got, they went from 1 million to 20 million in like six months.

25:31And, you know, those kinds of numbers are just really unique and not something that we've seen before. Typically you've scaled out and hired a ton of salespeople and, you know, created a big organization. And, you know, I just wonder if that's going to become more of the norm, smaller teams, fewer people, but they can actually scale these businesses really quickly um largely based on using ai tools themselves internally it's definitely the trend i'm seeing and so the question is if that is what's happening what do cap tables look like over the next five years right like yeah exactly and and when do founders take money if they have 16 people like how much how much investment do they need they're paying everybody if they just say they paid everybody a million dollars a year which i'm sure isn't the case.

26:20Right. Maybe$16 million a year. And if they're making$20, they're making$4 million in profits a year. I mean, the case that everybody references a lot out there right now is Midjourney, which I think has 11 full-time employees and is doing over$200 million a year. So if you just think about that for a second, it's like, that's an entirely different reality for how a startup can scale. So, I mean, it's exciting. It's also a little bit terrifying as far as Do they need VCs anymore at that point? I mean, are they going to need to raise money? What's the answer? I mean, I think they're not going to need much venture capital at that point if they're doing over$200 million.

27:04I wouldn't assume, but it'll be interesting to watch. The contrarian view on that would be that all the resources will go towards the scarcity. So you see the paradox is that all these AI companies are raising tens of billions of dollars because they're all compute. They're all focusing on compute. So it really depends where the bottleneck and where the next scarce resource comes through. Jason, what do you see as a second order effect in terms of, you know, the cost going down for everything? How does that change how you invest? You know, I'm very lucky to be pre-seed and seed. And then I get to work with funds like Kraft.

27:43And, you know, we have 70 companies, our super 70, that we've identified 70 downstream investors. And we focus on sending our companies to, there's about four of them that are, are like fantastic four who are LPs in our fund, and who we give very unique access to our companies. And then the rest of the, the, you know, super 70, we try to put them in touch with them. I don't think it's going to have too big of an effect on series A. It's certainly not going to affect seed and pre-seed because, you know, you need your first 500k, you need your first 3 million. And then why wouldn't you take, you know, a great Sequoia$10 million round or a great Kraft, you know,$5 million round, whatever it is.

28:32but series b and c you know could become my prediction might be we might see an industry brian um and i'm curious your position as a series a primary investor but i know you have a seed group too you know i wonder if series b and c will become buying secondary more than buying primary and so you know if you're a mid-journey and you had this amazing outcome like well maybe you just sell 10 of the company maybe you sell 5 of the company and just give liquidity to your employees and founders. And that's how you liquidate. It's kind of like a direct listing IPO kind of SpaceX secondary thing. I don't know.

29:07What are you seeing on the field, Brian? I am definitely seeing that more and more at this kind of like growth stage, Series B and later. So definitely more funds leading tender offers. The companies just, they don't need to raise more cash, but they want to get their employees some liquidity. And so that works. It's different It's unorthodox. But for us, as a firm, we don't have super hard and fast rules and we try to be opportunistic. So we have partaked in things like that outside of your just typical straight equity round. I think we're going to continue seeing it. I also think if rounds do get smaller, that's okay.

Read the full transcript

29:50The round size has got crazy the last two years. There's so much money, so many investors. Everyone's raising too much money. Founders have too much money and it becomes an issue. So I think it's just the best of the ecosystem. I think it's actually okay to raise less and to need less capital. It's not only okay, it's preferable. because man when a founder is sitting on 100 million or 200 million in cash in their bank account michael you're shaking your head like i think you've experienced this as well like it it f's with your head oh yeah i mean look at that deposit and then you see five percent you see 10 million dollars in interest a year you know 800 000 a month in interest coming in and you're like oh wow i can do crazy things with large piles of cash unnatural things Yes.

30:37You feel like you have to. The crazy off-sites and offices and hiring, and then it's time to get fit. And it's like, wait, we just cut all these things out. And we're actually, not only are we okay, we're actually better. We're moving faster. So it does feel like a drug. Raising too much money can be a real negative. This is back when we had offices. I always knew when a startup was in trouble, when the founders were meeting with architects and, you know, designing the lobby or like the open office areas and stuff like that. I'm like, what does this have to do with the business? Like just find an office space and no, no, we're creating a culture.

31:21We need to have these like pods and we're going to have this area. We have a ping pong table area. We're going to have this room and that room. And I was kind of like, this seems like an awful lot of cognitive load. And you know what? I see it with VC friends. They make some big win. And now they're meeting with architects to build their dream home. And I'm always like, you know what would be really good? Is to just build a home that's already finished. And it may not be my dream home, but close enough. And I can get back to work and back to my family. So prioritization and focus is so key. Yeah, absolutely.

31:51And we just went through so much of that as well. Just too much money in the system and so much questionable judgment. I mean, we feel like we're going to be kind of living through that for at least another quarter or two here. And we certainly see from LPs and institutional LPs, they're still living through the kind of ugliness of that. So it's definitely a challenge. Ryan, you've seen companies kind of get bloated. Have you seen any companies recover or is that kind of just, you know, psychologically they're addicted to the money and they can no longer recover? I've totally seen recoveries. And it's amazing, but it's also frustrating that, you know, that it kind of took, you know, a forcing function of the markets to do it.

32:39But I do think, though, there are some teams and some founders where the money kind of hid the issues. And they weren't able to kind of build an efficient business. Like there just wasn't true product market fit. You know, you have to keep in mind during this like Zerp era, it was just easier to sell. And so, you know, I've definitely... There are startups where maybe we didn't invest, but they were growing like crazy. And then the market turns and not only are they not growing, like they're shrinking. but certainly there are companies that had to get more efficient that did and they're better for it and they're growing into a valuation that was high but won't be that high in another year or so.

33:21How do you have that conversation, Jason? Because a lot of these companies are very hot and you want to get into the next round, you want to get your pro rata. How do you have that conversation with companies around facing reality? Yeah, you know, people who select me as an investor and a partner you know they know that they're getting jacal not to talk about myself in the third person but they know my brand is like candid kid from brooklyn i'm going to give it to you straight and so i tell them like i've seen this movie before and if you start blowing money this quickly and you take that 100 million and you divide it by 18 months we're going to be sitting here a month 12 or 14 and you're going to be regretting this decision instead of saying this is what i need over the next 18 months to accomplish these tasks and then putting the money out of your mind.

34:10And it was the same conversation I had with people about venture debt. Now, sometimes I'm successful. And during this, I would say two out of three times I was not. And so I'll give you the perfect example. Every founder of a company without product market fit wanted to add one to $5 million worth of venture debt on their round. And David Sachs and I had long talks about this on all in and previously i'm just like what is editing boards we were on together why are we doing this before we have product murky fit we got cash in the bank what is the seventh million dollars do we have six million in the bank we're going to add one or two million in venture debt why why are we doing this because somebody called us up and offered it to us i saw venture debt go go really wrong during the great financial crisis and i started go wrong during the dot-com era and And when the covenants start getting broken, even if you have a no covenant thing, when you can't pay back the bills, man, your whole life becomes trying to negotiate with a bank.

35:13And, yeah, you know, I think it took two years in some cases to convince people. And in many cases, we were not successful. They ran the car off the cliff. We told them, that's a cliff, not a bridge. If you keep going that fast, you're going over the cliff. There's not going to be another round of funding for you. We certainly can't do it. We're seed investors. You raised your Series B and you're racing towards a cliff like them and Louise. Like, is this wise? It's not wise. You know, take your time. You know, what's the rush here? And man, I don't know about you, Brian, but it's the ultimate frustration in the last couple of years is watching people blow through cash piles.

35:55And they're like, what did I do? I wish I had the incremental$5 million I blew on nonsense. Yeah. And especially with venture debt, when teams and founders confuse the venture debt as more runway, that always, again, it's another drug. So yeah, for all the reasons you and David talked about on All In, we advise founders to be very cautious with it. And, you know, there are some businesses and times where it may make sense, but for the most part, you know, founders need to know their bank account, their burn. They need to manage it really, really carefully. And I think founders who grew up in the Zurb era, like they didn't realize that until they kind of got smacked in the face with reality.

36:40Yeah. If you have a CFO, like a legit CFO, and the CFO tells you, yeah, you know, we should have a little bit of venture debt. I've worked with these folks before. I negotiated it. This is standard. That's non-standard. But when a 15-person company adds$3 or$4 million in venture debt because they think, well, I'm spending$500 a month, that's an extra six, eight months of runway. That's not what venture debt is for. You have to have profits or the ability to pay back that debt. That's why you would do it. Founders always ask me for pitch deck punch-ups. Well, I have some great news. We worked with the team at Miro, that awesome whiteboarding software, to create an amazing pitch deck template for founders, which you can see if you're watching the video.

37:21This will help bring your pitch from zero to VC ready. And our Founder University participants love this template. They use it all the time. So head to Miro.com slash Miroverse and search for Pitch Deck to check it out. If your team is hybrid or fully remote, Miro is incredibly useful. It's like an old school in-person whiteboarding session, but distributed and asynchronous. Miro lets you brainstorm ideas and collaborate on projects from anywhere in the world. When you think Miro, think zero to one, but faster. And Miro is so much more than a simple digital whiteboard. Your team can collaborate on planning, research, design, and feedback cycles.

37:57And remember, faster inputs equals faster outcomes, and product velocity is how startups win. So here's your call to action. To access our new Miroverse template and thousands of others, sign up today for a free Miro account at miro.com slash startups. That's miro.com slash startups, M-I-R-O dot com slash startups to sign up for free. moving on there's a new corporate venture capital fund in town we've been talking about ai the fund is none other than sam altman's open ai fund axios reported that the open ai fund which was set up in 2021 has already invested 175 million dollars in commitments which includes startups like descript and harvey noteworthy is that open ai's fund has outside lps which include none other than Microsoft.

38:43Brian, what do you think about OpenAI's corporate fund? Well, I mean, for them, it's a no-brainer. They have maybe the best access to developers and founders building within AI. They know the space probably better than anyone. And unlike a lot of corporate VCs, I mean, they have a leader and CEO in Sam who has a proven track record of being a really good investor and picker of people. So I think it's huge. I mean, they also, obviously, they know their product roadmap. So they have this unique insight into what they're building and what they're not building. And they're going to use that knowledge to decide what to invest in or what not to.

39:25I mean, every AI investment decision, I think at every firm, people are going to talk about is, are they going to build this? Is Sam and is OpenAI going to build this, but OpenAI knows that answer and gets to invest based on that. So I think it's a no-brainer for them. I'm sure we would, as a firm, we'll be co-investing with them. And I think, as you said, I don't think they're really raising outside capital, but I'm sure if they were, there'd be a line out the door of a ton of demand. Michael, corporate VCs date back to the early 90s until Capital famously was one of the most active investors in Silicon Valley.

40:02and then corporate VC really evolved with GV, originally called Google Ventures. What's the pros and cons of taking corporate VC for your startup? Yeah, I mean, from the LP position, but also just from being a former operator, I think too often you see founders at too early a stage say, gosh, wouldn't it be great to get validation by having this strategic investor come in this corporate and be part of the cap table? And I think what people forget all too often is, you know, the problem with strategics is they're not going to lead a round. They'll probably require a blue chip, you know, lead to be in the round.

40:42They're only going to come in once. They're rarely going to follow on in any rounds. and you know for the most part except for perhaps google ventures and others you know they're very seasonal meaning when the market is pumping you see a lot of corporate vcs when the market is going into a tough macro cycle you see a lot of those corporate vcs just you know lock the door and and shut down as we're seeing right now and so you know there can be some challenging and awkward moments in board meetings when you have a big strategic if i was right now in this ai space I mean, me personally, and looking at the funds we invest in, I'd rather have founders who are pirates, not people pleasers, meaning go out and scare the hell out of the open AIs.

41:28Don't go partner and take money from them, especially in a market where they're going to eat up a lot of little application companies along the way. So that's how I look at it. A lot of VCs get afraid that having a strategic scares away other potential acquirers. What are the pros, though, of taking corporate VC money? I mean, does it provide validation early on? It absolutely can. And I think that's why a lot of entrepreneurs, a lot of founders, you know, love to have that big name on their cap table. um so i think there there's certainly positives um in my experience the negatives outweigh positives generally especially in such a hyper competitive market like ai and it's the biggest ai company you know in the market who's gonna likely be very acquisitive going forward yeah if you want to have a large sustainable business you want the best venture partner in the world so if you could have your choice and if you think that um um i don't know microsoft's the greatest partner in the world would you rather have microsoft give you your series a series b would you rather have sequoia do it you'd rather have sequoia sequoia is aligned with building a large legendary company that goes public and is sustainable and becomes the next microsoft and competes with microsoft and you know with strategics and we saw this with open ai what it when open ai had problems what did microsoft do microsoft went in and said we'll take the entire team we'll gut it so there is the perfect example we're talking about you know sam's uh open ai fund which is open ai it's not sam's i think axios was kind of playing a little gotcha that it was under sam's name and not you know officially open ai's you know like journals will do it's it's fine um you know i think this they probably just didn't finish paperworking it properly um in the case of sam altman i will say no conflict no interest if i could put money into that fund i would do it immediately uh for the reasons bryant states and more number one they have access to proprietary data they know which apps are getting traction they also have the ability to give you access to software before they give it to anyone else and there was an instance with one of the companies we had invested in and they were like hey we can't compete against this company that um sam waltman and open ai had invested in and they're giving them early access so they can get early access now you'd be like oh that's unfair you know what life's unfair if that startup got that deal and that part of that deal is to get early access and they're giving them equity as we say in the industry no conflict no interest this is conflicted 18 ways to sunday which is why it's awesome you know um now and and who's going to complain about it you know who's getting hurt here i mean i guess arguably some startups that compete and maybe it doesn't feel fair and somebody might call that out at some point the descript competitor right and let's say descript you know can call sam altman up and say hey you know we have this problem with tokens or whatever can i talk to an engineer so yeah talk to joe talk to susan i cc'd them on this email you know and i have a descript competitor in my portfolio i don't but i'm just saying what if i did that company you know uh can't even get access to anybody over there and then those the folks there might be like you know what yeah we don't own shares in your company we're not obligated to give you you know um some competitive edge against the one we have equity in now if you were to think about this well why wouldn't apple do this with their ecosystem why wouldn't google do this with their android ecosystem well the reason is they don't want to have this kind of problem so open ai and chat gpt are too small to have this unfair playing field issue but as it grows, you know, maybe it will become pronounced.

45:13And people will be like, imagine Apple was like, yeah, we're going to invest in Spotify, but not title. We're going to invest in Uber, but not Lyft would invest in DoorDash, but not Instacart, right. And they started picking winners and they own 10 % of them. AOL did that back in the day as well. And Nvidia is doing that now. So conflicts exist in our business, they can lead to great returns. They can also lead to, you know, developers and people feel they can lead to a lot of bad feelings so be careful brian you mentioned you would be an lp in open ai if there's an opportunity would would you counsel your companies to take money from open ai why or why not some of the reasons michael mentioned like what why corporate bcs could be bad i mean what comes to mind to me is if they're asking for these weird special rights they want a rofer on acquisition you know potential mna or they say you have to use us as your preferred vendor.

46:05But if they're coming in with no special rights and they're not going to control the company, they're a minority investor, I think it could be interesting. And I think the companies that they've invested in, like Harvey, I think they may have seeded it, but Sequoia led the A and I think another big firm did the Series B. So I think the way I'm thinking about them is not as like they are the largest shareholder, they're just a part of the cap table. I'll tell you, if you're investing in a company in the legal tech, doing something with a co-pilot for legal, and that company is raising money and raising a Series A and you have a competitor, and OpenAI is going to invest in one of them, would I want OpenAI to invest in my company or the competitive company?

46:52I'd probably want them on my side. They're a special company. I think this is unique. This is different than if it was like Visa, MasterCard sort of thing. OpenAI, I think, just has such a lead and could be such a kingmaker that it's really strategic to have their involvement, even if it's more from a defensive standpoint. You look at the ecosystem, you have OpenAI, you have Kroc, you have Anthropic, you have Google. What's your view on the overall ecosystem and who will be the winner in your eyes? Well, I mean, OpenAI clearly looks like they have the lead, but I think the players you just mentioned, it seems to be like those are going to be the players and there's wild cards.

47:37Obviously, what Elon's doing with XAI would be a wild card. I think with Antropic, Amazon is a huge investor in that. So time will tell, but this kind of goes back to what I was saying before. It's really hard to predict the future. But OpenAI right now has a huge head start. They're releasing so much product so quickly and have such a talented team that it'd be hard to bet against them. What do you think, Jason? I am long open source, especially because of the controls that these players are putting on some of these models. um so you know if you want to i was asking gemini today like just give me a list of trump's legal cases i kind of did this in a trolling way on the all in pod and then i said i asked chat to me give me a list and gemini was like uh you know elections are complex presidential kinds blah blah you should use google search and then you know chat chapti was like here are the six cases where anyone here's a link to a story about each one with citations um i think people are going to want to know how these things work.

48:44And in order to make really elegant applications in verticals, you're going to need to understand how these models work. So I believe if you're going to build something in accounting and tax, you're probably not going to use ChatGPT. I think you're going to wind up using some open source model with some proprietary data. And that's going to be a better solution for that verticalized app. And then I think there'll just be just like there is a long tail of open source projects that do really interesting things. I think there'll be an open source of these models and they'll be faster and better and i think that's why apple you may have seen apple has an image uh open source uh maggie i think it's called so apple just released it it's terrible but i opened my apple uh photos just the other day and i had a picture of my bulldogs and there was that that little ai you know stars and i pressed it and it was like bulldog click here click bulldog it takes me to the wikipedia page for bulldog or the definition.

49:37So even Apple moving slowly, they have an open source image project. And it's basically to edit, manipulate, understand what's in images. And they're going open source. Now, if you're going to build your next app, you're going to use that or you're going to use, you know, Dolly, I think you're going to go open source. So I'm just a big proponent of open source in this case. And I also licensing of data is very much an active discussion between the lawsuit with New York Times and OpenAI, Reddit licensing to Google. So I think a lot of the paid models will have issues that the open source ones won't.

50:10Michael, what do you think about that? You're talking to all the early stage GPs that are investing in AI. What are the models for the future? How is AI going to monetize itself? Yeah, it's interesting. We had a little get together a couple of weeks ago with some of the managers who were investing in AI. And we actually had Blake Samick from OpenAI, who's the head of product operations, come and talk. And some of the kind of interesting things that came up that I wasn't aware of, I mean, if we think about it for a second, ChatGPT just launched in November of 22. So it's only been out there for what is that 14, 15 months total.

50:49One thing that I wasn't aware of, and I think is driving a lot of the investment activity for our managers, is of the$1.7 billion in revenue or so that's happening, in and around open and AI right now, the majority of that is consumer-driven, which was a little surprising to us. We just figured it was enterprise business, people starting to build tools, etc. And so I think that's a filter that a lot of our managers are applying and thinking about, you know, is this first wave going to be more a kind of consumerization of the enterprise type cycle where individuals are going to perhaps adopt tools, start to use them, and then eventually those tools will infect their broader organization or business.

51:41But that data was pretty surprising to us, and we think it likely is going to be important in just how things develop in the market. What does that say about the space? Is the opportunity a consumer or is it still an enterprise well in this case i think it's not so much it's consumer because all these are productivity tools or you know ways to kind of manage multiple applications or create a single pane of glass to you know various various applications that you use in your life and so um the way it got filtered in this discussion and we're talking about it is that you know more and more of these applications may have a kind of yammer-esque approach to the market where they get individuals to sign up for them and start using them first as a kind of life hack.

52:29And then they make their way into the enterprise. Brian, your partner, David, obviously founded Yammer, sold it for a billion dollars to Microsoft, another actor in this player. What percentage of your opportunities are you seeing in consumer versus enterprise when it comes to AI? I mean, we're really focused on enterprise B2B. So it's definitely more in that world. So it may be a little skewed because that's really what we're doing. But, you know, I have been a bit surprised by how few interesting opportunities I've seen in consumer. I do think that's going to change. Elad Gill had a good article.

53:07I think it was him today. But he made the point like chat GPT, it's still fairly new and it's changed a lot of things. And it takes oftentimes it takes six to 12 months for an employee at Google or wherever to decide like they're going to quit their job and go all in on AI and start building. things. So I think the next year is going to be really interesting to see what types of companies get built. I think we're still super early there. Jason, you're looking at startups at the very infancy. Sometimes it's just a couple of people and an LLC. Are you seeing more opportunities today, 2024 in consumer and enterprise?

53:43Yes. I mean, it's, you know, you have second and third time founders really like to go enterprise because they probably did something in consumer and they realized consumers lightning in a bottle one in a hundred figure something out and it becomes really big and then enterprise you know probably you know i don't know one in four or five have a great outcome so i think that's why a lot of people rushed into it it got a little bit too crowded that's why there were too many project management you know you'd have 20 different people going after some narrow SaaS vertical. But I love consumer and we are a power law investor.

54:23We do 100 new investments a year. We'll do 200, 300 names in our fourth fund. And then we'll reserve capital, half the capital for the top 5%, which will be 10 to 15 names. So we'll be super concentrated in those names when they break out. And so we can deal with consumer. whereas most vcs because they're placing 30 bets on a media craft you have 40 bets in a fund i'm guessing you have a billion dollar fund now and they also have multiple vehicles but you know if you're a classic uh 400 million dollar 600 million dollar fund i think you probably have 40 names in it most typically and michael you might know actually um what the the the numbers are now but thinking like um you know mark schuster at up front or fred wilson at um flat iron uh no i'm sorry union square now um and so you know what are the chances of hitting a one in 100 hitting a twitter uh you know listen fred hit it so a lot of people just go for for that for the enterprise ones because the hit rates are so much better but you're not hitting half court shots you're not hitting threes so if you think about this you know maybe enterprise is the layup of venture and uh consumer is the three-point shot and you get paid a much bigger premium if you look at my biggest hits uber robin hood com um those are all consumer thumbtack consumer and then if you go uh thanks for knowing my portfolio no but then i have data stacks and you know grin and uh density all unicorns like and those are in b2b so you know you can play either game i i let the founders tell us where the world is going that's i have that humility in the second decade of being a capital allocator.

56:05It's not about what I think. It's about what these founders think they want to build, how passionate they are about and how well they know the customer base. Brian, Jason called you out on portfolio construction. So let's talk about craft portfolio construction. How do you look at that and how flexible is your portfolio construction? It's flexible. And it changes based on the market. There are times where it makes more sense to be more focused on series A or series B. And sometimes it doesn't. We are always looking at the risk-reward based on the market, based on the space right now. So for example, with AI, personally, I'm probably more excited at the earliest seed stage for growth when there's a lot of more proven metrics.

56:51The Series A and Series B, we're going to do them, but they're harder. Because they're overpriced and without traction. very little traction um overpriced lots of hype everyone has an ai fund everyone's investing in ai it's you know it's it's the craziness again um and it's hard like it's really it's really hard like you know i think the more we learn about ai every day i think i create there's like more and more questions um that that come up it's very different than a lot of other you know areas and sectors where we are we're getting smarter and smarter every day i feel like we're literally there's more questions every day.

57:29So it makes it really hard to pick that Series A stage, especially right now. But when you look at your portfolio construction, are you still kind of general as a billion dollar fund? Are you still looking for one company to return the fund? Do those metrics change with fund size? Yeah, definitely. Because there are companies that sometimes I will see where I like the founder. I think they're going to have a good outcome, but it's not going to be big enough to return the fund. We don't invest in a company unless we think it has the potential to return the fund. So we will pass on things that could be good outcomes for the founder or for smaller funds, but they're not deals that we will do.

58:15Our sweet spot, we will lead C deals, Series A, Series B, and anything beyond that will go into the growth fund. Michael, you're working with much smaller managers. Some of your managers are 20, 30, 40 million dollars. How does that change your portfolio math on your managers? Well, we have a pretty specific approach and a specific strategy that we apply here. You know, we're going into approximately 24, 25 of these small funds. They're all 60 million or or less. Many of them are$20 million,$30 million. They average right around$30 million in size. And there is the allocation to those fund managers.

58:59And then specifically, we have the kind of opportunity fund for the broader community of managers as well, which is basically a direct investment fund for the follow-ons into the outliers that come out of those portfolios. And so for us and for our LPs, it's the combination of these two things that create the opportunity, a really steady, predictable, call it three and a half X return on the emerging manager funds and what we kind of underwrite at a four to six X return on the direct investments that go into the outliers from those portfolios. i'm curious what what is the name for that your type of fund michael because i know a fund-to-fund is and we know what a yeah you know a gp is and we what do you call these funds specifically designed to be a you know we kind of changed it up a little bit because the the fund-to-fund part of it meaning the capital that goes into the small emerging measure funds we charge no fees on.

59:58No management fee, no carry. And so when LPs come in, part of their capital is going to that and part of their capital is in this kind of direct allocation that's just going into the outliers that come out of the portfolio. We're only charging fees on the direct investment part of it. And the reason why we did that is we had feedback from LPs from the beginning. It's nobody likes doubling up of fees or seeing them stack since the managers themselves charge fees. And And so it is a little bit of a different approach. I'd like to say that we invented this, but actually there's a handful of single family offices in Silicon Valley who have been doing a form of this for a number of years where they basically equip an army of small specialist fund managers out there to go find great deals and invest in companies and then they will selectively invest more capital.

1:00:51Go invest, yeah. Yeah, exactly. And they do SPVs for these typically, or you do SPVs for these and then pass the hat, or you have the funds dedicated? So we have dedicated funds for the directs. But the one thing that we do that's kind of unique here to try to create a little bit of a network effect is when a manager comes to us and says, hey, I've got this company, it's doing a series A or series B now, and it's growing fast. And we give them$5 million to do that deal. We actually split the carry with the manager. And so we're helping that$20 million fund manager act like he's a$100 million fund or be able to invest further into the lifecycle of the company.

1:01:29And so a big part of that is, how do you help the small fund managers punch above their weight and get more value out of those companies that they identified early on? so they vet the companies early on they get you a foundation of bets and then you have to then re-underwrite them the best of those and it's the top one percent top ten percent yeah it's like two per fund generally you know they come out and these small funds you know they're making 10 or 12 investments a year so maybe there's 30 in total in that fund and so there's probably two or three that are going to be the real you know significant kind of high trajectory company so So you have to stay in touch with those fund managers pretty tightly to not miss opportunities.

1:02:13We do. I mean, speaking of AI, we kind of built out an analytics system to track those underlying portfolios. So we don't just wait for the manager to tell us how the company's doing. We also try to collect external signal and track the company. And oftentimes, we're approaching the manager and saying, hey, looks like this company's doing really well. Should we talk about a direct larger investment into the upcoming round? and that's how we'll get that entry point. Jason, I'm going to put you on the spot. You were early in Robinhood, Uber, Thumbtack. What was your pro rata? If Michael was around, how much could you have deployed before that?

1:02:49Large amounts because I was also friendly with each of those teams and they would have probably let me go super pro rata as well. So yeah, painful. It was a painful discussion. I mean, that's why after doing a$10 million fund, $11 million fund, I did a 44 and then I'll have this one, which will be 50 or so. um and you know now i have the dry powder to do it um and we could always fire up an spv if we need to to capture that with our lp pool um if there was a huge opportunity yeah i mean we we hear that all the time yeah you've done some you've done some empirical analysis on this what what's what's the opportunity so like uh well so if you if you look at this universe of small emerging manager funds and you look at the last 15 years i mean the really interesting data is if you take the entirety of unicorn successful companies that have come out of the market over the last 15 years 92 of those companies had a small fund like yours jason early in you know the earliest days they were investors there but then if you look at how much did they invest beyond the seed stage yes it is less than almost none less than five percent of the time did they ever even participate beyond the c stage which is just you know i mean with some of these companies it's it's hard to imagine in our first fund it was four point it's 4.9x on paper right now 5x or something and we did an analysis of the four unicorns that came out of it if we had just hit one or two of them with one more bet not two bats not a crazy bet it's like an extra half million or extra million um they would have been 15 20x fund so yeah you i think the way you get those outlier funds is a second there but brian how do you look at second and third bets it's hard to find these big winners and when you when you do you you pile in um but i do think it's could be a trap too um especially for for emerging managers who think like you just have to pile into any any prorata round um so i do think you want to look at it you know you you do want to look at it as a new deal and make sure the excitement level matches like what's actually happening at the company.

1:04:53There's very few companies that are special. And so the bar is really high for when we pile in, but we often will do pro rata and more than that. Speaking of pro rata, we're going to go from the theoretical to the specific. Let's look at everybody's last three announced investments. Brian, let's start with you. Sure. So I'll share a company, Solus, that we invested in. Solace Health. It's a marketplace connecting individuals with healthcare advocates to better their own or their loved one's healthcare outcomes. So the idea is pretty simple. Navigating the medical hospital landscape as a patient is a show for everyone, especially if you're helping an aging parent or a loved one who lives in another city.

1:05:40So these advocates are individuals who have a background in healthcare. They know how to play the game and navigate the system of getting the right referrals to the correct type of doctor, the right treatment, and they match you. So we led their seed. That was recently announced. I'm really excited about what they're seeing demand-wise from consumers, advocates, and health systems. The other one, Agentio, it's an ad platform connecting brands with YouTubers to create sponsored content. The idea being to make it as easy as it is to buy and purchase ads on Facebook, Google, Twitter, Reddit, but for creator-led marketing.

1:06:22I used to work in radio and the best performing ads in radio was when the radio host who had a following would actually do a host-read ad and it was authentic and it worked. So that's what these guys are trying to do. And there's been a bunch of these in the past, but this one got us really excited because the founder built Cameo's business and understands how to work with an onboard talent. The CTO worked on Spotify's ad platform. And then the third one, I'll do a wild card, is personal investment into a VC fund, which is Jack Altman's new fund that he recently announced called Alt Capital. Jack was the founder CEO of Lattice Unicorn in the SaaS, HR SaaS space.

1:07:08I love backing operator-turned-investors and really excited to invest in his fund one and excited to see where this goes. Michael, you're up. Okay, great. Yeah, last three investments we made into funds. The first one is Recursive Ventures, a manager named Idmar Novik. awesome small fund his fund number one was all of one million dollars uh out of that fund he wrote a 50k check into a company that is now doing over 100 million in arr and just yeah yeah and so it marks got a really unique background in that he's been an operator who took a company public but he's also been in the venture world and was briefly with morgenthaler Ventures and just an incredibly smart and scrappy guy who continually finds great deals.

1:08:00The other funds that we've announced, Original Capital, which is actually a generalist fund, but a team with a super interesting background and amazing track record and kind of a unique skill set. I'm glad it popped up even on the screen because that's one of their unique investments that's done really well. But Sumit Ghajri and Ryan Snow are the main partners there um both of whom spent time at carta um sumit uh chief strategy officer over there he was also a chief strategy officer at a company called instabase you guys might be familiar with which speaking of ai tools and fast growing companies and one of the reasons why i love these guys is the special kind of value add that they bring to their portfolio companies is they roll up their sleeves and basically run the financing process for their companies.

1:08:55Meaning when it's time to do a series A, when it's time to do another round, they will step in like investment bankers and run that financing process, which I know for so many portfolio companies is just a massive time-sucking challenge. And so they're an awesome fund. And then lastly, Silent Ventures, which is one of our, who notably doesn't have a whole lot on their website, but this is a really unique manager, Jackson Moses, who has been, aside from having a biblical name, has been investing in the aerospace and defense tech area for eight years. So as we like to say, he was country before country was cool and has developed very under the radar, one of the most amazing defense tech portfolios out there.

1:09:47And in the process has established a really unique point of view on what's happening in that market. And so these were the last three that we've done, all pretty different. Jake, what do you have for cooking? All right, Recall is a toolbar that allows you to take the various web pages, podcasts, YouTube videos, etc, that you visit and then put them into your own language model so that you can use it in the future and search it. So you can think of this, it reminded me of Delicious back in the day or Yahoo bookmarks, a lot of cool Web 2.0 products, Evernote-ish, if you think about that. So we think this is, and it's a paid product and people love it already.

1:10:27there's a lot of nerds out there who like to organize stuff so i could see this really helping people uh figure things out micro one is one of the fastest growing startups we've invested in recently they use ai to vet developers around the world so they can skim the cream of the top one or two percent and then package them up and handle um uh you know pairing them with companies that need projects done and because they use ai they can figure out really who's really good and who's not. And it's growing very quickly, micro one. And then Malengo came out of our last accelerator and got a massive amount of interest from investors and is very successful right now.

1:11:10What they do is they've taken the entire process of designing a hoodie, for example, and they will let you source, develop with AI what you want your hoodie to look like. I want a hoodie with bulldogs on it, blah, blah, blah. It makes the hoodie and then they will help you pick the fabrics etc because they have all of that stuff abstracted in the data from the factories they'll help you finance it and then they'll actually pair you manufacture it and get it to your distribution center so anybody who wants to create products and merch or even a whole business they're going to be like your soup to nuts uh platform for doing that powered by AI.

1:11:50Those are my top three for this week. Excellent. Well, it's been another great episode of the Liquidity Podcast. AI has truly taken over everything. For Brian Rosenblatt, Michael Downing, Jason Calacanis, this is your host, David Weisberg. Thanks for listening.

From the publisher

This Week in Startups is brought to you by…

Northwest Registered Agent. When starting your business, it's important to use a service that will actually help you. Northwest Registered Agent is that service. They'll form your company fast, give you the documents you need to open a business bank account, and even provide you with mail scanning and a business address to keep your personal privacy intact. Visit - https://www.northwestregisteredagent.com/twist⁠ to get a 60% discount on your next LLC.

DevSquad. Most dev agencies only offer developers. Why? Because product management is hard. Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist.

Miro. Working remotely doesn’t mean you need to feel disconnected from your team. Miro is an online whiteboard that brings teams together - anytime, anywhere. Go to https://miro.com/startups to sign up for a FREE account with unlimited team members.

*

Todays show:

David Weisburd hosts Bryan Rosenblatt, Michael Downing and Jason Calacanis to discuss Reddit’s IPO (1:19), Consumer vs. Enterprise AI (22:02), Sam Altman’s New Fund (38:18), and much more!

*

Timestamps:

(0:00) David Weisburd hosts Bryan Rosenblatt, Michael Downing and Jason Calacanis

(1:19) Discussion on Reddit’s IPO and potential as an advertising business

(9:28) Northwest Registered Agent - Get a 60% discount on your next LLC at - ⁠https://www.northwestregisteredagent.com/twist⁠⁠

(10:23) Reddit’s IPO and potential as an advertising business cont.

(16:44) AI Integration in traditional businesses

(20:56) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at http://devsquad.com/twist

(22:02) Consumer vs. enterprise AI

(37:09) Miro - Sign up for a free account at https://miro.com/startups

(38:18) Sam Altman’s venture capital fund and the future of the AI ecosystem

(1:05:06) Rapid fire segment on recent investments

*

Mentioned on the show:

https://www.wsj.com/tech/ai/generative-ai-business-implementation-ac995975?mod=tech_lead_pos4

https://www.axios.com/2024/02/15/sam-altman-openai-startup-fund

https://www.solace.health/

https://www.agentio.com/

https://www.recursiveventures.com

https://originalcapital.com

https://silentvc.com

https://www.getrecall.ai

https://www.micro1.ai

https://www.melengo.com

*

Follow Bryan

X: https://twitter.com/BRosenblatt4

LinkedIn: https://www.linkedin.com/in/bryanrosenblatt

Check out: https://www.craftventures.com

*

Follow Michael

X: https://twitter.com/michaeldowning

LinkedIn: https://www.linkedin.com/in/michaeldowning

Check out: https://www.mdsv.vc

*

Follow David:

X: ⁠https://twitter.com/DWeisburd⁠

LinkedIn: ⁠https://www.linkedin.com/in/dweisburd⁠

Check out: ⁠https://10xcapital.com

*

Follow Jason:

X: ⁠https://twitter.com/jason⁠

Instagram: ⁠https://www.instagram.com/jason⁠

LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis

*

Thank you to our partners:

(9:28) Northwest Registered Agent - Get a 60% discount on your next LLC at http://www.northwestregisteredagent.com/twist

(20:56) DevSquad - Get an entire product team for the cost of one US developer plus 10% off at ⁠http://devsquad.com/twist⁠

(37:09) Miro - Sign up for a free account at https://miro.com/startups

*

Check out the Launch Accelerator: https://launchaccelerator.co

*

Check out Founder University: https://www.founder.university

*

Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

*

Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

*

Check out Jason’s suite of newsletters: https://substack.com/@calacanis

*

Follow TWiST:

Substack: https://twistartups.substack.com

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

*

Subscribe to the Founder University Podcast: https://www.founder.university/podcast

More from This Week in Startups

All 653 episodes
Reddit’s IPO, Consumer vs. Enterprise AI, and Sam Altman’s New Fund and more!This Week in Startups · 1 h 12 min
Listen in VO