Today on the show, I am so excited to be joined by Ann Miura-ko. Ann is the co-founding partner of Floodgate, the seedstage venture firm she launched in 2008 with Mike Maples Jr. Since then, Floodgate has written some of the earliest checks into companies like Lyft, Twitch, Octa, Applied Intuition, Hebia, Nooks, Smarter DX among many others. A repeat member of the Forbes Midas list, Ann has built a reputation for backing category defining companies at their earliest stages. Ann holds a PhD from Stanford and has spent years helping founders think through the craft of building enduring companies. Today, Ann lives in Menlo Park with her husband and three children. She is the daughter of a NASA aerospace engineer. Let's welcome an
I have to start with the obvious, this AI pilled organization. This was an essay you wrote that went super viral. Tell everyone what you mean by that. Talk to everyone about the AI pilled organization and these five levels you very articulately put together on, you know, how AI'd you can be.
Yeah. So, the essay started because I had about a year and a half ago one of my CEOs that I get to work with had called me and said, 'I'm having an existential crisis.' And it was around the fact that he'd been using ChatGPT to code and had done a couple of things and had very unexpectedly positive results. And he's a very time constricted CEO. He was able to get rid of a lot of technical debt. He built out an iOS app that the team hadn't built in a long time. And so he was clearing all of this frustration using AI. And this is before everyone was really on to coding in such a autonomous way for someone who wasn't a coder. And this ended up spreading throughout his organization. And one of the things that he was really leaning into was not just enabling an individual, but enabling non-engineers to use AI and then going beyond that and really having the organization use it in concert. And so when I looked through that lens at all of our portfolio companies and then actually beyond, what I was starting to see was that there are AI pilled individuals within every company. There's someone out there who is using agents in some really novel way, but they're kind of on their own. Sometimes some of these individuals are quite secretive about what they do because it gives them a little advantage and so it's hard to have it spread throughout an organization. So there aren't that many groups who use AI in really interesting ways. And so it became sort of this thing where I wanted to find out who was really AI pilled not just as an individual but as a company. And so I started interviewing as many people as I could from a three-person startup to RAMP and Versel and then as big as Wix which is a public company to see what people were doing and it was eye opening to see sort of really interesting innovative companies that are building AI first products that maybe aren't as AI'd as a company that has no AI really inherently within the product, but the organization itself is agentically immersed.
So fascinating. What's wild too is there's these like two use cases. There's like your culture and your how your organization operates. You can use AI to the extent that you know your leadership wants you to. And then there's like the product you're selling and how agentic and AI native it is. And I think people sometimes get confused with that like you said like they can be really far in one category but not in the other and then you know that can cause things. Um, what have you found is most important? Is it most important that your technology itself is super agentic and AI native and that's really pushing the boundaries and you're learning with your customers or is it more important that actually you have this like company brain? I mean, I'm sure you get pitched a lot of those these days, right? Um, that your organization itself is AI pilled. Which one are you seeing matters more?
Yeah, there's a few pieces to it. I think one is obviously the leadership has to be really bought into this and part of the reason is when the leadership isn't bought into it there's a bunch of things that go wrong. So one is the AI actually needs to be able to see things in order to operate on top of it. And so there's this whole question of what is legible to AI? What databases? What emails? What codebase can it see? The more it can see, the more it can do for you. And so that's clearly leadership has to be bought into that. The second piece is that if you're not an engineer, typically a lot of those non-engineer, non-technical folks are a little bit scared of what they might end up doing if they use AI incorrectly. And so there has to be a little bit of permission to make mistakes to try it out and so the more publicly leadership and particularly non-technical leadership uses AI or the technical folks teach others to use AI within the organization then you start to see a lot more adoption and so I think Toby talks about this from Shopify they have this product called river where the default is that you have to leverage these agents in public and I think that's a really great example of how one can learn from other people see what's happening and then the fear decreases culturally totally.
It's funny as you're saying that I actually find that a lot of the non-technical talent tends to be more of the culture carriers as well. Like you know like the friend who's like running marketing that seems to be everywhere at every event and is like so passionate about the product like getting them to adopt it and getting them to be excited about it is the path. What do you think is the biggest barrier other than like fear of failure between you know this like you know AI nativity or you excitement around AI and the non-technical leaders within an organization? what's like the gap and how can we close it?
Yeah. So, if you look at an organization like RAMP, what they have is this product that they've written about called Ramp Glass, which enables someone to come in and on day one actually have everything that they need connected into this basically like co-work environment. So, one of the things if you're non-technical and you walk into this environment, the first thing you need to do is like MCP server into all of these different data sources. And that's actually already kind of a scary step, right?
It's intimidating. Even people are like, 'What is that?'
What is that? Like, and so it would be better if that was already provisioned for you, right? And so in that case, you know that you're not going to mess something up or do something that you're not supposed to do or expose data that maybe is secure. So there's all these fears that you have once you have to do something super technical. Some people don't want to be in the terminal, right? And so command line interface looks a little bit scary. And so the degree to which you can take down those psychological barriers and create an environment where hey this is all legitimate and you can work within this environment. We've already provisioned it for you. I think that reduces the fear quite a bit.
Totally. One thing I've learned talking to GPS on the show and in my own experience as a GP, your back office is a signal. How fast you close deals, how clean the LP experience is, how your K1's land. Investors notice all of it. The more buttoned up you are, the more likely they are to give you more money in the future. That's why I want to talk about Sidecar. Sidecar is the SPV platform built for fund managers who want institutional quality execution without hiring a full back office team. They'll review your deal within hours, handle full secondary transaction support, and give you transparent pricing up front. No platform carry. Also, your LK relationships stay private, which is super important. It is not a marketplace. If you're running a professional fund, your infrastructure should look like it. Sidecar makes that possible without the overhead. Check them out at sidecar.io/partners/trailblazers.
This is getting a little bit more into your investments, which we'll talk about, but because we're starting to lower these psychological barriers and these actual technical barriers to creating software. There is a very exciting wave of like non-technical founders getting into our business and starting companies. What is your take on the future of the nontechnical founder being, you know, the having the potential to be the next great founder? And I say that because our industry has really typically leaned for the like technical founder. Ideally, they're commercially savvy, too. That's a bonus. But really, you need to be able to be technical to build the, you know, the foundational software that we all know and love. But things are changing. So, what's your take on on that nontechnical founder archetype?
Yeah. Um, so I've always loved the combination of a fairly technical, joyful builder with someone I would label as a superinker. And that person may or may not be actually technical, but you actually have always needed that person. And I would say today, even more than previously, you need that person who is an absolute rabid truth seeker. Um, and the reason for that is there's a lot of things that you can now build and there's very low barrier to doing so. But the real question is why? And the real question is who will buy it and why will they care and is there durability? And I think without that added detail, your business has a chance of lasting 3 months, but 3 months from now, we're not sure if you'll have real durability. And so, um, there's probably even more emphasis on that superinker.
Yeah. How do you find the superinkers? I mean, it's sort of a crazy question in venture of sourcing. How do you know, right? How do you know someone has these special traits that's going to make them, you know, the founder of a generational company? Are there certain things you look for to pull out? Is someone a superinker? Are they a truth seeker? Are they going to ask the right questions when they need to?
Yeah, I actually really like to engage with founders. And this makes it hard when when a deal is like super hot. Um, and so that probably means that I can't really engage in um in in a process where it's like, okay, in 24 hours you need to produce a term sheet or not. That's just not my style. Uh, usually I'm engaging with the founder over the course of at least a week and we're going back and forth in terms of here's what I think I understand about your business. I'll even write it down and then I'll have a bunch of questions about that business that I also write down this is not just a conversation. So we'll have the typical 30 minute 1-hour conversation but out of that I need to write down what I know about the business. Everything from this is what I think your product does. This is what I understand about the technology. This is what I think your core insights are. This is what I think inflections you're riding on. These are your competitors. um these are the bets that I'm making. This is potentially the risk that I'm facing. This is what I understand about your background and why it's relevant. And I'm looking to see how an a founder engages with that information. Truth seekers will not always agree with everything that I write, right? And I'm going to get a lot of things wrong because this is just my impression of what you're doing. And so I want to understand how you think. And so in that engagement process, I need that back and forth and I'm looking for that. The other piece is I I I engage a lot in teaching because some of that is you get to see someone in their most raw form when they're a student. And I think as a student, you start to see elements of who actually is a truth seeker or not. How do they engage with information? How do they um wrestle with it? How do they disagree with themselves? How do they change their minds? Those are all things that I'm looking at to see how curious a person is.
I love that. It's like so particularly timely because I think so much of it too, it's whether or not they agree with you is the excitement to engage.
Yeah. you know, like I think, you know, like I sent like a laundry list of a lot of what you're talking about to a founder just yesterday and the founder just like did not engage in the way that I would want. You know, like let's get into it. You know, I think it's this. No, I think it's this. Okay, but we're both right here. And, you know, I think that that like almost like that sparring is so much of the fun of building.
You talked a little bit about teaching. I'd love to talk about that for a second. Um, the Mayfield program at Stanford, iconic.
Tell me a little bit about what made you want to start that. Well, so I wasn't the founder of it. So there's you're just the leader of it now. I'm a co-leader of it. So Tom Buyers, who's been leading it for 30 years, um is the person who founded it. And I think he was so visionary in this that um I think at the time he was trying to understand why why are there all these co-op programs? It's like people go abroad, they go to all these different places, but there's this incredible place that Stanford happens to be in called Silicon Valley. Why don't we have a co-op program right here? And so the vision for it has been, it's a 9-month program. You start with three months where we teach students, and they're all undergraduates, um, ethics, leadership, and entrepreneurship. And then we just finished that quarter in the summer. They all live together in San Francisco and they go to 12 different internships. We actually visit all of those companies and do open houses at all of them. And so it's almost like they all are doing 12 internships at the same time.
Oh, so each intern goes to all of the companies, not just the leaders.
Yeah, we all go to see all these different startup companies just to get a different feel for oh this company looks one way, this company looks another and then the last 3 months which is the fall when they come back they teach each other and they write one paper on an inflection that they see.
Okay, so can I do this program? Like we need this for adults. Sounds pretty epic.
It's really epic. It's 12 students. Um, and I get to know them really, really well, which is really fun.
That's amazing. So, there's a long list of incredible alumni. I know Mike Kger and Kevin Sistro started Instagram, maybe the most famous. What were they like back then? Were they What was it like teaching them as part of the program?
So, they were part of the program before I became a co-director and co-instructor. So, that was sort of the Tom and Tina era.
Got it. Got it. Um, and I also know Josh who started Gusto. Was he part of your era or is he right before you?
But he actually continues to teach every year in the program. So, um, he's someone I know much better in the context of the program. He actually comes back and teaches an entire class on culture and we try to place it at the very beginning of the class because he talks a lot about what values are and how you take values and place them within a company and grow that. How do you think about the values of the company and make sure that's translated into all the things that you do? And so we try to do that for the Mayfield Fellows, too.
That's amazing. Yeah.
So, there's this trend in our industry, speaking of culture, where we back a lot of young people, I may or may not have gotten pitched by a 14-year-old recently, which I have opinions on, but those are mine. Um, and a lot of Silicon Valley likes to back the, you know, the 18-year-old dropouts and sort of these younger um, adults who maybe haven't experienced culture in another company. Um, how do you teach culture? How can you learn culture when you're trying to build it yourself? And I say that because I think that's something that has been hard for me to see as sort of a fly on the wall at times. Sometimes the younger companies struggle with what does culture mean? How do you lead with values? How do you not micromanage or how do you inspire? you know, some of these like very important questions um when they haven't done it themselves.
Yeah. It's I think it's a really sort of foundational question. So part of what we're investing in is when we look at investment, we're not just looking at a product. We're not just looking at a single founder who's going to build a business on their own. We are looking at their ability to recruit, their ability to build a great company. And so there has to be that piece too because I don't think every part of it is observable and teachable by the VC. Um and in fact most of it is not right. Um part of what I look for is um you know my my partner Mike likes to say we're we're investing in people who are time travelers. they are sitting in the future and they time travel back to today to try to get us to help them bend the the curve of the future to where they see the future should be. Um and in order to get there, they have to convince a mass group of people to come along with them. And that that's the movement that they're creating. And a founder, if they can't create a movement, they're just they're just seeing the future. And in some ways, you can say they're not visionary. They're just having visions, right?
And so how do you translate someone who is able to create a movement? I think those people like they manifest in a lot of different ways.
I think those people like they manifest in a lot of different ways. And that's why I think some people feel like leadership has to look a certain way. They'll say, 'Okay, this person was really mean and bossy and so that's the way to create a movement.' I think a lot of it is dependent on what are you trying to accomplish? Who do you need in order to bring that vision to life? Um, and so you'll see like much softer leaders who are incredibly inspirational, but then also drive a very very large business with a huge vision. And I would say like Josh Reeves is a really great example of that. If you ever meet him, he feels like this incredibly driven leader, but someone who is deeply deeply ethical. Um he doesn't feel like he's going to be like someone who yells at a ton of people, but he's quite inspiring. And then on the other hand, you'll read all these stories or watch movies about, you know, Elon Musk or Travis Kalanick and they feel like a very different kind of leader, but also quite inspiring to many people. And so, um I think it's a really hard question of how you assess it. Uh but you you have to get like a good sense of it over time.
It sounds like it's also about embodying the authenticity of the founder and then creating a culture that attracts that type of talent that would thrive there. So like I think there's a different person that's going to thrive at Gusto than is going to thrive at Uber totally and then is going to thrive at SpaceX. Like I think it's and it's figuring out and maybe this is the work that the VCs have to help with especially for the younger founders. How do you clarify what is like authentically your style so that you can create a bigger organization beyond just you? Cuz to your point, if you can't build a movement and you can't attract people, you're just sitting there thinking about the future. You're not actually creating anything, right?
And I've seen people who are, you know, 24, 25 years old and, you know, they've hired someone who is 60 years old and that 60-year-old is like, I can't believe how excited I am to work for this person. I'm like I'm so inspired like my whole career has been building towards this moment and so I think some of it is dependent on what are you building and why does it matter and so therefore what are you doing for your customers that is meaningful and can change the world and so I think those are the things that I really look for.
I love that.
If you're building in public, sharing insights, or staying top of mind with your network, you need a newsletter. And if you have a newsletter, you need Beehive. You know how I always talk about writing essays that change the trajectory of my VC firm? Well, I publish all of them through Beehive. It's my absolute favorite platform because it serves as a blog, a newsletter, and a website all in one, so I don't have to republish or reformat across platforms. Beehive is the creator platform where newsletters actually grow. We're talking built-in referral programs, a recommendation network, and analytics that tell you what's working, not just vanity metrics. Plus, you can monetize from day one through their ad network, paid subscriptions, or boosts. No platform cut eating into your revenue as well. I can speak from my personal experience. I'm always getting ping for new ad opportunities. Beehive has a range of customers from major publishers like Time magazine, Techcrunch, and Newsweek to solo operators earning seven figures from their inbox. It's the same platform that's built to scale with you. If you've been putting off starting your newsletter or outgrowing whatever you're on, now is the time. Go to beehive.com and use code trailblazers30 for 30% off your first 3 months.
So, I have a confession. I used to be a compulsive notetaker. Every single meeting, I'd be half listening and half scribbling and still leaving with gaps on next steps, details that were shared, and more. But Granola completely changed that for me. It's an AI powered notepad for meetings, and it's connected to every single call on my calendar. Before each call, it shows me a well-researched brief so I know who I'm meeting with and the full context going in. During the call, I jot down whatever stands out. Maybe it's a key word or a decision I make. And Granola handles the rest. It'll transcribe in the background on the call and then turns my rough notes into clean, structured takeaways the second we hang up. There's also no bots joining calls. It just works in the background. I use Granola for several things. If I finish a meeting with a potential investor in my fund, I'll ask Granola, 'What could I have done better to get my point across?' If I'm meeting with a founder I like, I'll ask Granola to point out any major green flags or maybe red flags I may not have already caught. For people with a lot of meetings and decisions that require endless context, Granola is a gamechanger. Actually, we're running Granola on today's episode, so you can read the full show notes at granola.ai/trailblazers. New users get 3 months completely free. That's granola.ai/trailblazers.
So, one of your very infamous early investments is Twitter. I guess we'll now call it X. Um, and Jack Dorsey is I would say end of one. Um, talk to me a little bit about first meeting him and deciding to get involved in that company.
So, that was one of Mike's actual early angel investments. And, um, I think the story goes it was actually pre, pre Floodgate. Well, it was pre Floodgate, but it was pre Jack Dorsey really being CEO. Okay. So, this was an Ev Williams investment. Yeah. Because Ev Williams Wow. And so he actually had um he had a podcast app called Odo that Mike had originally invested into and I think that they decided to give the money back to all of the investors at one point and Mike basically said I'll just roll it forward into whatever you're doing next and it happened to be Twitter. And so, um I think like it what's really interesting lessons that we learned from some of those angel investments was that you just don't know what's going to come of these fast-moving product cycles. Another one that Mike invested into that I saw a little bit more closely was he invested into Justin TV um which was basically a it was an app to live stream Justin Khan's life. So he had this sort of contraption on his head where he could video his point of view um and live stream it which doesn't feel like a big investment at the time. I mean, it feels like if someone were to pitch us that now, it'd be like, hm, market might be a little small for just your fan base. Doesn't social accomplish that? It was a really weird idea. And I remember going to meet with Michael Cybel and their team a couple times. And in the last meeting that I remember, Michael Cybel told us that the company was splitting into two. One was called Twitch and it was going to enable people to watch other people who are live streaming gaming. And the other one was called Social Cam. And I remember leaving that meeting and turning to Mike and saying, 'I'm really glad we have Social Cam because who's going to watch another person game?' And then we walked down the street and I remember when I heard how big Twitch was becoming, I was like, 'Well, I'll be darned. I cannot predict what consumers like.'
So funny. And there's so many niches of the internet that like we don't even understand.
Big niches, too. Yeah. Yeah. Huge giant niches.
That's wild. That's uh It's awesome to see that up close, though. I didn't realize Michael Cyel was so involved with Justin's company that early. He's such a legend, though. I mean the world is small also that mafia is quite interesting too.
Okay. Who else is part of it?
So the CEO and founder of Cruz Kyle was also part of that too.
Kyle Voy I think right? Yeah. And so for those who don't know Michael Cable is now you know very involved with Y Combinator and has been sort of like a big prolific VC now for some time.
So another one of your legendary investments Lyft.
Mhm. Um, rumor has it there's like a 10,000x that people talk about. Um, you know, tell me how did you first meet the Lyft team and you know, if you can share how big was that return? So, what was I I think you've had Leah Sullivan, of course, on the podcast, but she was the founder of Task Rabbit, and she was also my very first investment.
Yes. And so, um, when I first started Floodgate, I was actually still finishing up my PhD at Stanford, and I, uh, I promised my mom I was going to finish it. And so, I'm sitting there, I'm married, actually, and I have a 18-month-old. I just started floodgate and then uh I'm still doing this PhD and I think at the 8 month mark oh no actually April so 11 month mark I actually had my second child and 6 weeks after that I defended my PhD thesis and then I think I met Leah in October or so of that year and so that was my first investment so it was just sort was this whirlwind year and Leah was sort of at the end of that.
Uh so she moves out from Boston. She had been part of this found uh was it Facebook fund uh incubator
And so she introduces me to two guys that she had shared desk space with at this incubator and that was John and Logan. And when we met with John and Logan, the crazy part of the story was that there wasn't a single transportation startup that existed at that time. It was called Zimride. And so we had seen cuz John was John's last name. Was like Zimmer or something? No, it came from actually from Zimbabwe. Oh, it wasn't. What are their last names? So it is John Zimmer. But uh Logan Green really started Zimride in the very beginning. Oh, so just a coincidence that his last name looks similar. Okay. Okay. Um John John joined as a co-founder. Um but I think it was after it was named and uh so I I saw the company. We hadn't seen anything in the transportation space. I ended up talking to Scott Griffith who had started Zipcar asking him, 'Hey, I think transportation feels like a really big industry. We haven't seen anything in this space. have you seen anything? And I think it was right before Uber got started. And so he told us, haven't seen anything in transportation, but it feels ripe for something to happen. And their pitch was they were creating a platform in which people can actually exchange rides. And so it was mostly for at the time universities. So, if you wanted to carpool to your school, you could do that. If you wanted to find a one-off ride, you could do that as well. And it was live at Stanford. It was live at most of the UC's and a few other colleges. And the plan was actually go out to a few other companies. We're going to approach Hila Packard, Facebook, some of these other companies. And that's how they grew for a little while. But it became very clear that there just wasn't enough density in the activities that they were doing. So over the course of I think a couple years they really expanded their notion of what they wanted to do. And in 2012 they decided this whole platform was not working. Did a hackathon and then came up with this peer-to-peer. And it was already after Uber had launched but Uber was still black car services. So it was their tagline was ride like a baller and they had that pink mustache too. So they were like funny they had personality. Lift had the pink mustache. Yeah. So I was just saying ride like a baller was Uber's tagline. Oh, so it was more like fancy. They were fancy. Only black car services. And so there was a debate internally of whether or not Uber would come after this peer-to-peer kind of funky space where Lyft in the beginning you put this huge furry pink mustache on the front of your car. The riders would get into the front seat and fist bump the driver because it was supposed to be like your friend was coming to pick you up. And then the drivers also responded by having sort of funky themes to their car. So there was like lift karaoke, there was lift trivia, there were all these different types of drivers that were going around. And so it was a really fun, innovative experience at that time. And so they were very different from the Uber experience. And then within I think six months, Uber started to realize that this was going to be a thing. And they said Travis went to all the different cities we'd launched in said, you know, if you don't shut this down, we're going to also launch our own service. Uh because he felt it was not legal and all these other things. Uh when he realized that the cities were not going to shut it down, he just went live with his own service as well.
It's wild. It's, you know, there's um there's a lot of like famous rivalries in our industry. I feel like you were part of, if not the most iconic, one of the most iconic ones.
Yeah, that was a really wild ride.
I mean, I can only imagine. What's wild about this story is so much of what started to work happened a couple years after you invested. And so then a lot of people ask the question of like, how could you know? It's the same thing as your Justin story. Like, so glad we have social cam. You know, Twitch will be what Twitch will be, but you know, social cam is a thing. How do you explain identifying these opportunities? Is it luck? Is it great founders? Is it like you said transportation swipe for disruption? Like after almost two decades now of investing? Mhm. What's what's the thing that you think makes you pick someone when you know it's still a couple years out potentially and many pivots away from figuring it out?
I think that's like the the question, right? And everyone has their own opinion. I think I've in my old age I've grown a lot of humility. So I I would say there's a lot of lady luck in the process. Uh I've actually in the very early stages I've let go of the idea that the initial product idea matters so much and I invest entirely in people. And when I say people, I think a lot of people have a very loose definition of what they mean when they say, 'I invest in people.' Most of the time it's vibes. I really like this person. They seem really smart or they have the right resume. Uh I'll go back to this notion of superinker and superb builder. And we have very specific questions we're asking. We have very specific internal debates about the qualities of these people. Um the I probably the the only other characteristic I'm really looking for is tenacity. Uh sometimes the the founder just has to outlast everyone. And so if you've just bounced around, you know, 9 months here, 12 months there, I'm just not sure you have that. And so that's another thing I look for. Um, and then there's sort of this I think the vibe I am looking for is um,
Someone once said, 'Oh, that person is inevitable.' And I remember hearing those words and just being like, 'That's exactly the term I'm thinking of when I'm looking at someone.' Um, and it's very like Thanos from Avengers, right? But at the same time, there's something about being inevitable that is so important and I think it encapsulates a lot of different things.
Yeah, it's a really good word. Um, it's a really good word and it ties a lot closely to this movement conversation we were having earlier that like you see the future, you're working towards it, it's inevitably going to happen, you're just convincing people along the way to join you. So, I think that's really clear. I want to make sure I circle back on the lift return question. And I realize we didn't answer that. Can you share like how how big did it get? How well did it do for your firm?
Yeah, it was it was so you're always looking for a multiple fund returner and that was definitely a multiple fund returner. So we got in at a $5 million valuation and we sold a little bit along the way um actually at a price that is even higher than it is today. So, um, we were able to get a good chunk out at that point and then at the IPO as well. Um, and so I can't give you the exact returns, but it was a it was multiple fund. It was a multiple fund returner just on its own. And that that fund also had OCTA. It also had um, Ignite, which is actually interesting. It just got bought by a PE firm and that was also uh, a multiple multiple fund returner as well. So,
Yeah. It's always nice when you have many.
I know it's a power law business, but but the many helps.
The 2026 primaries are taking shape. And if you have a strong opinion about how they're going to go, Koshi lets you actually trade on it. Koshi is the largest prediction market in the US. Federally regulated and available in all 50 states. You're not betting against a house. You're trading against other people in a live market, taking yes or no positions on real world events, elections, federal interest rates, economic data, you name it. Right now in Kelshi, you can trade on the California governor race, Senate outcomes, and a dozen other major political storylines as they develop. As the probability shifts, you can buy in or out of your position in real time. It's a completely new asset class and honestly one of the more interesting ways to have skin in the game on what you're already watching closely. Download the Kelchi app, that's K a l, and use code trailblazers to get $10 when you trade $10. Or go to kshi.com/r/trailblazers to accept this $20 offer. With Kelshi, you can trade on anything. 18 plus only. Restrictions and eligibility requirements apply. Event contract trading involves risk and may not be suitable for all investors. Prices, values, and available markets may differ from those mentioned. For more information, see kshi.com/regulatory. Okay, so a quick experiment. Think about the last long message you typed. Could be a Slack thread, a prompted to claude, maybe it's a detailed email. It probably took you 10 minutes, maybe even 20 to get it right. Now imagine you just said it out loud instead. That is the whole pitch for Whisper Flow. Whisper Flow is voicetoext that actually works in every app on every device. You speak naturally and it outputs clean formatted text that's ready to send. No setup, no integrations, no fixing weird transcription errors. And it works across Gmail, Slack, Notion, Claude, iMessage wherever you type. And unlike the built-in dictation on your phone, Whisper Flow removes all filler words, mid-sentence corrections, and jargon. What I personally love about it, too, is that it perfectly matches my style. So, I often type in all lowercase letters, so it'll type like that. I also say things like LMK, which means let me know in shortand, and it'll auto adjust it from let me know to LMK. Like many of you, I also do a lot of brain dumping into LLM's. So, instead of typing it all out, I actually just speak my windy train of thought into Whisper Flow, which is infinitely faster than trying to get my fingers to keep up with the pace of my thoughts. If you do any serious writing or just send a lot of messages and emails, using Whisper Flow is a no-brainer. Get one whole month of Whisperflow Pro completely free at ref.wisperflow.ai/trailblazers.
One thing that I've been super impressed with you guys is you've stayed very disciplined on fund size. Um, we're saying this as Benchmark is now one of the last to fall. They've raised a much larger fund, which good for them, but they've always been also very disciplined in their own way. Uh, you guys are 18 years in and you still raise solid funds, but they're not multi-stage. And a lot of the other folks in your cohort, I think of you guys as like OG seed funds, you know, with sort of like the first rounds of the world. they've scaled and you guys have stayed diligent. Talk to me about why you've stayed so disciplined on fund size and what your philosophy is on it today because the the market also looks pretty wild and uh there's a lot of arguments about what's the right fund size to deploy.
Yeah, I think it sort of depends on how you want to operate as a venture capital firm. And I think for for me and for Mike, we just really like working directly with the founders. It's just what we love. We love the personal relationships we have with them. We love getting to know who they are, what they're building, why. Uh we actually feel that that's also the way we learn. Uh we do not learn very well when we are hands-off. If we are learning through u another person who is doing marketing, I don't think Mike and I learn very well. And so we need to kind of see the problem firsthand, understand it, talk to the founders, understand that journey, and then only then can we really translate that for other folks. And so part of what someone gets when they invest when they receive an investment from Floodgate is they get our time. They get an and Mike Maples, Mike Heler, Irish Troy, they get the partners and they get all of us actually because we don't do that many investments. We're we're fundamentally not a platform. Um, and as a result, we cannot scale like that. Um, but they know at the very least that that is what they are getting. Um, when they get us, they also get, you know, between Mike and I, we each have basically 20 years of experience of seeing companies go from zero to one. We've seen that done really well. We've seen that done really poorly. We've seen all of the mistakes. And the thing about going from 0 to one, I wish it was a science scientific experiment, right? I think growth in many ways is science, but 0ero to one is a series of anecdotes. And so you're you're sort of looking for patterns, but you're also looking for what's unique about this particular situation. And you're trying to provide the CEO, the founders with the right coaching for that particular moment. And if you don't know the details, if you're just sort of a an observer at the highest level, I think it's really hard to give the right advice at the right time. And so that's why we've chosen to be more pure play in terms of do we build out a gigantic platform to do all the things that we want to do. um it's just not the right mechanism for how we learn and how we impart that knowledge to to our portfolio. Um it's also just sort of I don't know like our personalities work better that way. A lot of people describe Mike as the fun uncle. I'm sort of tiger mom and so you know you kind of know what you're getting when you receive an investment from each one of us. So I think that's that's point one.
Point two is um in this world I think what we've seen is that there are really um you can have optionality in different ways but you can't have optionality in all ways. And so in what ways do we not have optionality? Well, we only invest at preede and seed and and so we have no entrylevel optionality. If we miss something, we can't come in at the A or the B or the C. So that's the only moment at which we can enter into a working relationship with the founder. So that puts some pressure. If someone wants to work with us, it's the only moment where we can really find that opportunity. And so other folks, they could choose to work with them in the next round of financing or even after that. But this is the only moment where we can really work together. So that's hard on one hand, but it also forces a choice.
Um the second is though we have exit optionality because we are a small fund. There's a few things. Number one, the small check we're writing will be a dent maker in our fund. And that's why an and Mike and Mike are all writing the checks themselves because we're not going to pass it off to an associate to write the check. that $1 to5 million check really matters for us. Um, and because we only make four to six investments per year per partner, if that one doesn't make it, it's not just sort of a, oh, well, it didn't make it, it actually really matters to us, too. And so, I feel like we're really aligned with a founder in terms of incentives. And then the last piece is that um because we're a small fund, a relatively smaller exit will actually really matter for us. And so I'll give you one example which is um for for us we recently had an exit with a company called Smarter DX. For us it was a great $1.2 billion outcome. It happened in less than four years,
Which by the way, the time horizon matters a lot in our business.
Yeah. And so, you know, usually you're holding out for like 10 15 years. This happened in less than four years. Um, greater than a billion dollars. And so, we ended up returning 2/3 of our fund in that moment. And because we were still in the investing phase of this fund, it was the first first investment and I made out of the fund. We actually returned more capital than we had actually invested at that point. And so it was a for a lot of folks these days, a billion dollar outcome just doesn't even start to matter. which is crazy if you think about it as a founder, it actually if you think about it as an investor too, right? A billion dollar invest a billion dollar outcome should matter cuz it's a big deal and for us it actually really does matter. And so it that was like to me really interesting because our exits we have a lot more optionality. Um, we can even participate in secondaries too, right? Because if if Floodgate sells some portion of our investment, that's not seen as as big a deal as if one of the multi-stage actually starts to sell their position. And so, uh, and often times we're actually asked to sell some part because the multi-stage can't have as much ownership as they need to. um
They always want to gobble it up as the company's grow
