Today on the show, I am so excited to be joined by Rebecca Kaden. Rebecca is a general partner at Union Square Ventures, many of you will know USV, the thesis-driven firm based in New York that backs companies changing market structures from the outside in. Over the years, USV has written checks into category-defining companies like Coinbase, Twitter, Stripe, Cloudflare, Abridge, Radiant Nuclear, and Generalist. Before joining USV, Rebecca was a partner at Maven, the consumer-focused early-stage fund, also based here in New York. But she actually began her career far from venture capital as a journalist for Narrative Magazine. She credits that work with sharpening the instinct she now uses to spot breakout companies, understanding how a story comes together before everyone else can see it. Rebecca studied English and American Literature at Harvard and earned her MBA from Stanford. Today, Rebecca and her partners at USV are focused on the next wave of transformation: the rebel alliance forming the new agentic stack, data at the edge unlocking entirely new data sets in the physical world, an application layer built to obliterate markets rather than merely automate them, and programmable energy as the horizontal foundation beneath it all. A native New Yorker, Rebecca has come full circle. She lives in New York City today with her husband and two sons. Let's welcome Rebecca.
Thanks for being here. I'm so excited.
Okay, so we start every interview with a bit of an icebreaker.
You can take it any direction you want, but it is quite meaty. I'm not giving you a softball, okay? So, we talk a lot about the hard paths here. So, when you think about your journey so far, professional or personal, what has been the hardest part of your journey so far that almost broke you?
Ooh, this is a good question. The hardest part of my journey that almost broke me. I don't know if it almost broke me, but you know, I came from a background that had no exposure to this industry, you know, really at all. I felt like a real outsider in it. And I was looking to make this change, and a mentor of mine had said to me, you know, I think you should get into venture. I think it would be a good fit for you. I'm, you know, I'm kind of an innately curious learner. I like the process of learning things over and over. I like people. He thought it'd be a good fit, but I got into it and I, you know, had imposter syndrome times a thousand, right? Because the industry asks you quickly to have legs to stand on, right? Why are you here? What are you offering? And it took me a while to really learn that and to figure it out and to kind of learn on the job what my strengths were that I could offer without, you know, just being the last thing I did in the world. And I'm now very grateful for that because I think that kind of experience and self-reflection, you know, gives you the confidence when you get there, but it was a journey to do it.
Totally. You say the last thing I'll do in the world. And I think a lot of VCs say that, that it's sort of like their final job. When did you realize that? Like I would imagine, and I may be projecting here, but I would imagine like post Stanford, you get your first venture job and you're like, let's see. Like let's see if I like it. At what point in the journey, I think it's been like almost 15 years now, right? Like when were you like, oh, this will be my final job?
Well, I very much think I believe in doing lots of things in the world. I hope I have, I hope I am a core investor for many decades to come and I also hope my future holds lots of different explorations and projects and ways to contribute in all kinds of ways. But on venture, you know, I think it's a little bit addicting, right? Like you get into it and I'm competitive by nature. I'm competitive against myself. I like learning new things and you realize you're kind of on a treadmill of doing that, right? Where your core job is to continuously think about what's around that corner, right? And the investors I admire most are people that pick well and operate well with their founders they work with, but are also experts at seeing around the corner, right? They're investors that I think are excellent at picking up on momentum and running after it. And that is a huge skill and one I admire and, you know, in many ways aspire to do, but I admire more the seeing around the corner, if that makes sense. And I work at a firm with people I think are really excellent at that. But you experience that and you want to do it again and again and again and also these things have long life cycles. It takes a long time to see it through and so you realize, you know, every time you commit, you say, 'Here we go. Like here we're going for a decade, you know?' And that's a long road. So I don't imagine getting off of it and I don't know exactly when it happened. I think, you know, your portfolio adds up and some work and some don't work, but you kind of just get... I love that experience of getting excited about an idea and a hypothesis and starting to pull that thread and keeping it going and going down some kind of false roads, but then going down the right ones and getting finally to that company and having that conversation with the founder where you're like, 'You're who I've been looking for.'
That's amazing and I kind of always want to do it.
I love that. I think this concept too of reframing like venture doesn't work in terms of years, it works in terms of cycles. So like if we say like every fund is 10 years, I'm just generalizing, like you're kind of only like one and a half iterations through.
Yeah, I very much think in terms of like either fund cycles or market cycles of like how many of these things am I going to get to see?
And which do you think you use more? Is it like the fund cycle? Cuz I'll tell you as someone who has gotten to know the firm, I think of you guys as like each fund you really sort of step back and think about like, okay, what's the thesis here? And obviously right through the market cycles, but I would objectively say like fund cycles are how you guys measure time and like how I think about you guys like grounding yourself especially in your writing. How do you think about marking time?
I think a lot about market cycles because especially how can you not right now?
Right? Like I think anyone who has kind of been through the past cycle and then is sitting on this precipice, right? We think a lot about Carlota Perez, right? Which has kind of installation eras and deployment eras. That's her framework. And if you think about the internet, it had a massive installation era, then it had a boom and a bust kind of, but out of that came messiness, but also an incredible deployment era. And you just see really, really shown in that deployment era, right? That's where you got Twitter, you know, that's where you got Etsy, that's where, you know, you got kind of these things that really change how people... What interests me about technology isn't technology itself. It's the hypotheses about human behavior that it enables. And that's where that really happened. And it's, you know, you sit at this moment and you see all of the installation that's happened pretty quickly in the last kind of couple years and then you feel this bubbling of this deployment cycle about to happen and it's pretty exciting. You're like, this is what a market cycle feels like. Let's go. Like it's going to be messy, there's going to be busts, but out of that is going to be the impact of technology that changes how we live. And you know, that's what we're kind of here to do. And so I think about how many of those kind of cycles am I going to, you know, be able to lean into.
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You guys wrote a really interesting piece. So, there's a lot of pieces you've written, but I want to talk a little bit about this like rebel alliance.
Which you guys I feel like are most known for, especially recently. Like this idea that it's not going to be these like big large foundational model companies that'll take up all of the market share, but there's actually a lot of opportunities, especially consumer.
Right? Like you talk about the deployment era. Like there's just so much on the horizon. Can you explain to people who, you know, maybe look at like an OpenAI, where they have an infinite number of downloads and members and distribution built in, how is an up-and-coming startup going to defeat them or compete with them? And talk to me about your rationale, especially on the consumer side, because I think your essay was so well-written and very thoughtful, and I'd love for you to share more of those insights with folks.
Yeah. So, the idea of the rebel alliance is the idea of a stack, and that a consortium can take on the big guys. And if you look at the history of the internet, one thing we love about it is it's built bottom up. It's actually not built top down. And there are things that you would do on the internet if it was built top down that would have been really nice, right? Like packaged neatly, and things would have made sense. But actually, the beauty of the internet are the weird corners, right? Then the weirdness that comes out of it. And these kind of bubbling up products that emerge that only can happen because they're kind of stacked together. And we're looking at right now, and we have in some ways a more top-down technology market than we've had in quite a long time. And that's because of how capital has been deployed, and that's because of kind of fundamentals maybe of how, you know, large language models work. And there's benefits to it, and we're not arguing that those aren't going to work. It would be a weird argument, right? Those are working. And we're benefiting from them. But what we're arguing is there's also room for the consortium, and for the stack, and for the pieces to sit on top of each other, and to take the market as well, in this kind of Rebel Alliance way. And what that means is things like open-source harnesses, or, you know, the or open-source models, or things that can be used without walled gardens around them. And we're seeing a gravitational pull towards it. I think users are interested in it. I think builders are interested in it. And I think there are benefits of control, flexibility, pricing power that come from building in a stack, and not, you know, reliance on the kind of big behemoth in the room.
Which is very exciting as a builder because you're not dependent. Your fate is not in someone else's hands.
Well, I would say it's essential as a builder.
Yeah. Right? And this wasn't always something we thought was, you know, definitely going to be true. Maybe 18 months ago we actually published something else called the four quadrants. We called it the four futures. And the idea was really it's hard to write a piece where the punchline is basically we don't know what's going to happen, but the punchline was basically we don't know what's going to happen. And what we argued in it was we don't know what's going to happen because we're in this time of ambiguity where a lot of it depends on probably two axes. One is how open or closed the models are, and two is how fast the progress is, right? Do we hit asymptotes and limitations that we don't currently foresee, or is past precedent and these just kind of continue functionality smooth. And that really nobody knew. But there is a world in those quadrants where the closed large models win everything. Right? And in that world, the application layer kind of doesn't exist.
Right? It gets totally absorbed.
Did you guys assign percentages to each quadrant? I don't remember seeing that.
Everyone wanted us to. Like every LP wanted us to. Every founder wanted to. But our point was like, we don't know.
But maybe it's like looking at your portfolio because I think this is something that Fred had mentioned was like, so these are our four quadrants, we'll invest in each.
Yes, our punchline was we want exposure to all four quadrants.
Why pick when you don't have to?
No, and our argument was that doesn't, you know, what we were trying to say is what's advantaged in each. And one, the large models are advantaged, but also things like programmable energy is advantaged, right? Because kind of actually the horizontal undercurrent of everything is you need dramatically more efficient, faster, ideally cheaper energy to fuel the ecosystem. So we were saying like, you know, even if the large models kind of win the day and own everything, you're still going to need that energy.
Blanket stuff too that like across all scenarios, it's a smart bet.
Like almost like the umbrella.
And energy's our biggest bet there actually. I think that's now, that's I think kind of a consensus point of view, though I think there's a lot of different angles of energy.
But you guys were definitely early. Like I remember, everyone was saying...
You know, yeah, we launched an energy fund in 2019, I think. You know, and so, you know, we've been very, very excited about new formats of energy, you know, programmable energy, which is really the ability to control and direct energy in new ways with technology, but also new formats of energy generation, like Radiant or Zanskar around geothermal. So, all across the energy stack. But we were scared that if the big large language models won, particularly if really one of them won, there would be no application era. And we thought about that, so we thought, okay, what do we do in that case? And, you know, what do you invest in? But what we've realized, which is part of, you know, for us always theses build on top of each other, they're never kind of on their own. And the Rebel Alliance directly comes out of that. Because what we've realized over time is, despite the large models doing so well, there's still competition, right? And there's actually increased competition for I think a bunch of reasons. One is there isn't one winner. Two is there's increased price sensitivity, right? Those models realized, and those companies realized they want to make money, so they couldn't just do super subsidized, you know, subscription prices across the board. Sad for all of us, really good for the application layer.
Right? Because competition creates opportunity at the application layer, cuz now there's something to compete for that, you know, business to be built on top of. Open source models are, you know, they're now talked about a lot, but they're a real contender, and there's real benefits. And so, there's more competition at the model layer than I think at one point we thought might be true, which has given us a lot of renewed conviction in this application layer and the idea that it wasn't going to be fully absorbed. As has the kind of fundamental truth that we probably should have known all along, which is it's really hard for big companies to do all the things.
And we've learned that lesson in every cycle, right?
This is true, but the behemoth always feels so... I mean like this everything's AI cycle is like never been done before, growing faster than ever. So there's always the what if of and always...
Totally. And yet you see them launch consumer verticals and stuff. And some of them will work and some of them won't work. The same way that that was true at Google and that's been true at Meta.
And that's kind of the nature of large companies and you might argue, and I think we've been talking about that actually, I think the desire for continued capital at scale, which they really need to survive, might force even more focus.
Yeah. You'd hope. You'd hope. I mean you'd think, right? Cuz there's only so much to go around.
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I wanted to ask you about like the alpha you uncover and how much you share versus not. So, you know, you guys have done such an interesting job publishing always since like the dawn of time where you see the world. I think the four quadrants, let's use that as an example cuz you just talked about it. It's like a way people can now talk about scenarios of who's going to win. But in a lot of ways, that is a little bit of your alpha like that you've created these like four quadrants and that your LPs can know, 'Oh wow, they're being more diversified about it.' And so, how do you guys decide what to share, what not to share, and do you ever worry that you're like giving away the secret sauce or do you have more of like an open-source view of it too, where like you want to benefit the ecosystem?
A totally open-source view of it. I actually think our alpha is the opposite.
I think our alpha is public thinking.
And putting our ideas out into the world.
Talk your book. But one of the things I think resonated with me about USV from the first time I've, you know, spent time with the partnership was that idea. That we actually think gatekeeping ideas is a, you know, recipe to lose. That actually, what you get by, you know, effectively open sourcing ideas, right? And putting... We call it public thinking, or often we call it half-baked thinking. If you know, you know, what we really think about and what my partners have really pushed on me is our goal is not to produce the Oracle, right? Or to say this is the answer, or to say this is the ultimate market map of X. It's to say, 'Here are some ideas. We're more sure about some of them than others, but we want them out into the world because we want the feedback, right? Pressure test our ideas. Pressure test them by disagreeing with us, by agreeing with us, by sending the companies that relate to them, which is super helpful.'
Yeah. By you saying, 'Oh, now I know you're interested in that.' Right? Like, maybe, you know, we wrote about data at the edge and a lot about physical world AI. Maybe you were like, 'I didn't know they were so interested about that, and now I do, and so I'm going to meet a founder that's, you know, focused on that, and I know that USV wants to talk about it.' Also, our theses get better. It's that it doesn't happen in an intellectual box. It happens in the real world.
And so, you can only do that by getting ideas out there. So, I actually think the alpha comes by taking those ideas and being better about connecting the dots to how those become investable businesses, not by the ideas themselves.
We're also giving everyone a framework to use. Like, I think that's so much of your public thinking that differs from other firms is that sometimes other firms will just talk about like an exciting launch, and like, 'We want to invest more in this area,' right? But you guys really are like, 'Here's the four quadrants, you know?' And like, this is a framework...
Yeah, you know, I think mostly it helps us because it's just how we think about things, and I find it really... I think about our kind of thinking stack, right? We have a Rebel Alliance stack, which are the pieces of, you know, building agents that are going to launch into the world and change how we live, but if you think about our thinking stack, I think about frameworks. Four quadrants is a framework, right? I think about frameworks, I think about theses, I think about ideas, and then companies.
Right? So, like, frameworks is kind of a worldview of like, how would I make sense of what's going on in a market? A thesis is a hypothesis about where there's opportunity. Ideas pull that into specific verticals, and companies are things you can invest in. And ideally, we want to build all down that stack.
A thousand percent. Okay, so you set me up perfectly for this. Okay. Tell me your process. So, like, do you start with the framework? Do you start with the thesis? Do you meet a brilliant founder building a company and see if it fits something you've already done? Like, what is the process amongst those sort of four levels...
...that you go through? And I know every company is so different, and maybe every partner within USV is quite different, but I'd love to hear your strategy for finding great founders and where you start.
I think it's really evolved over time. I think when I got to USV, it was pretty bottom-up, right? And I would, we would know kind of the theses and the, you know, or the overarching ideas, and then I'd want to meet a lot of companies and see kind of how I can connect the dots. Over time, I spend more and more time really on that thesis...
...because I find that the more I can know what I'm looking for, the more likely I'm going to thread the needle of the right idea and the right team, right? Cuz I really want both. And the more likely I'm going to have a conversation with that founder that, one, gets out the things that I actually think I need to make the right decision, and also differentiates the conversation. Right? So that I'm going into it and saying, not, you know, 'Pitch me a business and I'll tell you if I think it's good.'
Yeah, what do I know, right? And more, I have a hypothesis about how a market works, and you have a hypothesis about how a market works, and you're probably spending a lot more time in it than I am, but we've done our work, right? We've prepared our minds. Let's have a conversation about where we align or don't align. Way more effective.
And way more interesting. Like selfishly, right? It's more about like ideas. Yeah. Yeah.
More likely for I think that I can walk away and say, 'That's a founder I want to get behind,' cuz I think it's better in a lot of ways. And I've really learned that process over time. I don't think I came in with it, but I do think I've learned it. And so I now really, you know, rely on it, but our process in developing the thesis, you know, people ask this question, and I always wish I could give a clear answer, and I can't because it's like everything else for us, it's like pretty bottom-up. You know, it's like we're meeting companies, we're talking all the time. We devote a lot of space within our partnership to talking about ideas, not pipeline or portfolio. We have designated times we talk about pipeline or portfolio, but we also have designated times we talk about ideas, and we prioritize it. And so we kind of pull the thread sometimes an inch at a time and sometimes a mile at a time, right? And it depends, and sometimes it feels like we're not getting anywhere, and then sometimes you're like, 'Okay, it's like coming together.' And we generally write it like when we feel like we've been saying it internally a lot.
Like it comes up three times in a week or something, and you're like, 'Okay, this needs to go out.'
Rebel Alliance is a great example. We didn't start saying those words internally. We also had developed a real perspective on open source harnesses. And now we've made several investments in the category, maybe none of which have been announced, but probably by the time this comes out, they will be.
And that's a piece of the stack, and we'd also, you know, been looking at other pieces of the stack, the consumer layer, you know, open source model, different parts, and thinking about how these come together. We'd also been real builders in it. Right? And we built a lot of kind of an agentic operating system for ourselves and we were seeing how we were doing that and the tools we were using and, you know, what we were relying on and that was informing it, you know, this stack was becoming clear in our mind and finally we're like, all right, we got it. We got to get it out there cuz we want to see more of it and we want to encourage it. And we want that conversation to happen and for us to be a part of it. And so that requires a whole like a hodgepodge simultaneously of us pushing each other on the ideas and we're always like tighter, crisper, narrower, right? Like, you know, shorter, tighter, crisper, like how, you know, less broad, you know, and then when we finally feel like it's clicking, we'll put it out into the world.
I love that. One of the analogies that I use with my writing is I think of it like an album where I have like the headline, like the title of the album and then I have like all these songs underneath it aka additional essays or supplemental, but there's very much like a headline and that usually, I mean, we'll see how long I do this for, but so far it's been like every few years, every fund you sort of have like a new album that you put out.
Like an artist and I'm really inspired by like a Taylor Swift of the world where like at every point in her life she's got like her Red era, she's got her Lover era and you can kind of tie that to like certain focus areas or certain market cycles, if you will. How do you guys think about like the umbrella? Is it just cuz I see it as sort of like you guys just throw smart ideas out, but how do you think about like the cohesiveness of it and bucketing them as like, you know, this is like our 10th fund and so these are like all the things under the 10th fund or...
It's way less neat than that even though that sounds really nice. Like, to us it's actually the same. So we publish new, we've published, I think, four theses collectively as a firm over 20-something years, right? And in our minds, we publish them when we feel like the previous one is no longer articulating the overarching thesis that we're going off of. So, we've said it in different ways. There's been large networks of engaged users, which is really USV thesis 1.0. There's large networks of... They're all building on each other, too. Large networks of engaged users differentiated by user experience and then also the data layer underneath them, right? There's, you know, there's been these kind of iterations. The last one was, you know, changing the structure of markets from the outside in because of kind of structural pressures. Actually, those are all the same thing. Right? And we have these moments where we realize this. Like, I was looking for an old blog post on the USV blog that had nothing to do with this cuz I was trying to pull it up for some founder I was working with. And I came across one that Fred had written, I think in 2014 or '15, that's called Obliterate, Don't Automate. And what Obliterate, Don't Automate is, is don't change markets from the inside by, you know, making it easier for the existing gatekeepers, change them from the outside by changing the structure of the markets involved. And you're like, this is just what I've been saying over and over and over. And it's actually we rephrase it for different moments in the market, which I think we have to do. But the overarching theme of what we're saying, which is how do you change market structure? All markets have gatekeepers. And there's a temptation in technology to build for the gatekeepers, to create efficiencies on the inside, right? Agentic software for healthcare systems. It's not that we don't think that's a good business. It probably is a good business. It's not what we want to do. We want to think about how can you make the system more direct? How can we drive the cost of healthcare in this country to zero? Not by making it more efficient for the gatekeepers to exist, but by eliminating them. How can you structurally change education so that it's not, you know, bounded by geography and cost? You can build direct-to-learner product, right? You know, how can you democratize the internet and give power to the individual versus the platform? You can build a web and an agentic stack versus a centralized force. So, it's all really the same thing applied to kind of different market moments.
It's interesting too because a lot of it is just like philosophy. It's sort of like how you view the world. Like I think a lot of like, I used to joke like...
creator economy and crypto and a lot of stuff. It's all about like decentralized ownership and like it's sort of like there's it's different technology in different eras, but it's you as a firm sort of take a stance on what is your philosophy. And I think it's so cool that 10 years later you can find a piece and it's got that same DNA. I would say a lot of it has to do with the fact that you still have so many of your early partners involved.
Like Fred's now, you know, excited?
Yeah, totally. And and everyone's allowed at USV to kind of have those moments, right? And like reignite, you know, and be like, "This is the moment we've been waiting for." And it's very cool to see that when it happens. Um cuz there's this aligned interest and then these different threads of it that get people excited, you know? As you just said, crypto and agents, you know, and direct to learner education are actually all to us going towards the same goal of a more direct,
personalized, customized, yeah, whatever the words are, yeah.
And so, you're just pulling these different threads towards the same goal. And that when that it doesn't always hum, you know what I mean? But when it hums, it's really good.
There's also the argument though that that is so um one view of the world. Should the funds be having multiple points of view, right? Like I don't know what your take is there. I you know, I know you guys invest like across a lot of different kinds of sectors and obviously we're talking about programmable energy. You guys have done a lot in crypto, social back in the day, like all that stuff.
But is there a take ever internally like, "Hey, we've been sort of like beating this philosophy since the dawn of time. Should we sprinkle some bets in more cuz it feels maybe easier is the wrong word, it's always hard to build a business, but when you think so lofty of like let's just like cut out the middle man and let's do this like let's rethink education from first principles." It's often harder than the like almost like I don't want to say quick hits, but a little bit of the quicker hits of like you know, selling to people that are already there.
But it's pretty fun and interesting. So, a few things. So, you need diversity in lots of ways in a fund, right? You definitely need diversity of ideas, you need I think diversity of categories, right? Like I don't think you need every form of it. And I actually think having unified goals and values matters. Um but you definitely need diversity. I think we we get that because we are pulling lots of threads of this expression. Also, kind of by the definition of being early stage investors, sometimes you invest in things that move around. Do you know what I mean? And so, you're investing and it's like, "It's bottom-up. It's going like towards that view of a decentralized world." Nope, it pivoted, you know, and actually it really hits. My best example of this is always a bridge.
Right? Which we love a bridge. We're thrilled to be in a bridge.
Shiv is a N of one founder.