CEOInterviews.AI
Start App
Rebecca Kaden
Managing Partner, Union Square Ventures

EP11 Rebecca Kaden

📅 Jul 19, 2025 Human Unicorn Pod Official 37 MIN 822 VIEWS 193 SEGMENTS · 2 SPEAKERS
🎙️ Human Unicorn Podcast — Episode Title: "Conviction Over Consensus: Rebecca Kaden on Backing What Others Miss" 📄 Episode Description: In this episode of Human Unicorn, Nihal Mehta talks with Rebecca Kaden, General Partner at Union Square Ventures, about how to spot — and stick with — breakthrough ideas before they’re obvious. Rebecca shares how her path from journalism to VC shaped her investment lens, what it takes for a company to be truly venture scale in 2025, and why some of the most transformative businesses don’t look like obvious winners at the start. They explore: How she define...

Questions asked in this interview

12
  1. 0:00Um why the [__] are you in venture capital?
  2. 3:35... you've been able to work with like through, you know, uh, at Maveron maybe even, but especially at Union Square, like what are some of the, um, you know, the similarities and the core tenants, um, behind some of these most amazing people?
  3. 9:47how many deals do you do a year?
  4. 13:00Um but um like how do you look at your raising your kids uh through that lens?
  5. 17:22Um, and how I guess how were you raised that you uh that you've iterated on in raising your kids or had also maybe stayed consistent?
  6. 22:23Do you have dinner at the same time?
  7. 22:42Um, do you have dinner at the same time as your kids?
  8. 25:36Um what's going on with America?
  9. 29:21... you talked about industrial revolution um in terms terms of AI, you know, if this is the industrial revolution, everybody's like, "Oh my god, we're going to be out of jobs." What is your what is your thinking on what AI does to human?
  10. 30:16Is AI going to replace you and I?
  11. 34:35Um Rebecca, what is your purpose on this planet?
  12. 34:48We, by the way, we we covered a lot of ground today, right?
Nahal 0:00 ↗
Well, now here we are. So, we're back. So, we're back. Um, hey guys, I'm Nahal. Welcome to the Human Unicorn podcast where um I get to uh chat with friends, uh epic friends who are human unicorns and they're human unicorn stalkers and they're human unicorn coaches and they're human unicorns themselves, of course. And [Music] Rebecca, you've been uh a great friend over the past many years. Um we're lucky to have some investments together. Yeah. Um why the [__] are you in venture capital?
Rebecca Kaden 0:44 ↗
Oh, um very accidentally. I um was originally a journalist and in publishing and writing and loved that and thought that was what I would do and then like many people who don't really know what they want to do went to business school.
Nahal 1:02 ↗
Mhm.
Rebecca Kaden 1:02 ↗
And I was at business school and got very close to a mentor there who was a guy named Bill Campbell who passed away a number of years ago but was known
Nahal 1:11 ↗
he's the epic coach didn't he do the coach like Larry and Sergey or
Rebecca Kaden 1:15 ↗
Yeah. Yeah, but he had a fascinating career which is well written about um and he wrote a book and there's books about him but um he started his career as the football coach at Columbia and in this like very winding kind of journey which I love um became chairman of Intuit, only person at the time on the board of both Google and Apple, and this coach to all these big names in Silicon Valley and was known for his style which was um like loving but direct and I like that style.
Nahal 1:44 ↗
Yeah. Um, and he also you are also loving and direct. I'd like to be. Yeah. Uh, you're more direct to me than loving, but you're definitely I could see both sides.
Rebecca Kaden 1:58 ↗
I think I'm loving at least kind. Um, and um, but I do I value directness and I think it's helpful and I always liked that. And he was loving and direct to me. Um, and he he taught at GSB and I got to know him and I went to him really not sure what I wanted to do. I knew I, you know, wasn't going to go back into journalism. I knew I was interested in technology and had, you know, been redpilled at Stanford. Um, I was trying to figure it out and he
Nahal 2:35 ↗
And by red pill, you don't mean Trump.
Rebecca Kaden 2:37 ↗
No, I don't mean Trump.
Nahal 2:38 ↗
Okay. Thanks. Drank the Kool-Aid of technology. Yeah.
Rebecca Kaden 2:43 ↗
As the future. Um, and he was the first person that said to me, "I think you should be a VC."
Nahal 2:49 ↗
And he was an adviser to Maver. Mhm. Great firm on the West Coast.
Rebecca Kaden 2:54 ↗
And he introduced me to Dan Levitan who runs Maver.
Nahal 2:58 ↗
Amazing.
Rebecca Kaden 2:58 ↗
Um, and that was how it all started.
Nahal 3:00 ↗
And that was it.
Rebecca Kaden 3:01 ↗
That was it.
Nahal 3:01 ↗
That was it. Um, I love the journalist to venture capitalist track. Um, aka kind of Mike Moritz. I always say thank God for Mike Morris because it would be a really weird one except people are like well Mike Morris so then it then it's a great track.
Rebecca Kaden 3:17 ↗
Yeah. Um because the things in common and I think about kind of what we're doing every day like all the all the clues, right? Um basically creating like trying to find the truth through all these little glimmers of uh data or hunches or intuitions.
Nahal 3:35 ↗
Totally. I always say, you know, I think it's a couple of things. the the risk tolerance, the output, much of the job is is completely different. But I think most jobs or many are really about people. Um and and one thing I love about venture and love about stories and journalism and writing of all kinds is that it's really about people. And um you know I think the similarity is you're trying to kind of thread together these narratives and stories with you know fewer data points ever than you would like to have and probably more than you need. Um and ultimately build trust where people are going to you before they're going to other people and be that kind of go-to source. And you know you want the scoop of a story, you want to see the investment before others. Yeah, it's oddly similar. Um, and speaking of seeing the investment for others, I'm always so proud of myself. I'm like, "Hey, Rebecca, have you seen this company?" She like, "Yeah, passed on it 3 weeks ago." Um, so, so you do see a lot. Um, uh, I can see the journalistic kind of skills, uh, you know, in in your work every day. You talked about people. Um, in terms of like all the amazing people you've been able to work with like through, you know, uh, at Maveron maybe even, but especially at Union Square, like what are some of the, um, you know, the similarities and the core tenants, um, behind some of these most amazing people?
Rebecca Kaden 5:11 ↗
Um, yeah. I mean, I there I think there's a lot of them and there I I've spent a lot of time I've got I'm so I'm a believer in apprenticeship venture capital. I don't think it's the only way to do it. There are certainly um examples of people who have done it other ways, but I'm a product of it and I'm a huge believer in just the immense value and pleasure of soaking up learnings and knowledge from people who are just excellent at their craft. and I've gotten to do that which is kind of an incredible thing. Um but I think about my partners at USV and um there's so many kind of they're actually all very different and they're unique thinkers which is one of the things I've learned to look for. Um I think it's pride in original thought and the ability to create original thought um and to have perspective. It's an ability to keep pulse of what's going on in the world but also block out noise.
Nahal 6:08 ↗
Mhm.
Rebecca Kaden 6:09 ↗
Um and understand, you know, what's heat seeking and what's actually important.
Nahal 6:15 ↗
Mhm.
Rebecca Kaden 6:16 ↗
That I really admire. Um really good intuition about people and understanding the importance of people in it. Um and this process which USV really cares about which I have learned and super value of what does it mean to develop a thesis to really form a point of view and then go execute on it. And that's not what's going on in the market. And that's not what's the hottest thing out there. It's what is something I believe about where the world is going, right? And how it is going to get there. And really pushing that and kind of being relentless about really pushing that forward until the point of the sphere is sharp enough to act on it. Um I think the other thing is this balance that I think a lot about in venture between um hustle and urgency and patience and that we all kind of have to balance both, right? Where this is an an industry built on impatience in a lot of ways. Like you want to be the first to something. You want to see stuff before other people do. You want to act. You want to go fast on deals when you need to go fast. You kind of always have to be on top of it. The information flow is ceaseless. It's like this constant pace, right, that I like and is also dizzying. And then it's knowing when to be patient, that we don't need to jump at the first thing that we we will wait until our ideas are clear enough um that you know, you have to kind of sit with it sometimes.
Nahal 7:38 ↗
Yeah.
Rebecca Kaden 7:39 ↗
Um and and I think that's hard and I think when I came in, I thought it was hard and they've taught me a lot about the skill of patience. I mean, I think about, you know, my partner Brad, who is one of the founders of USB, who is the most patient investor I've seen, and he just he sits on ideas and he thinks about them and he hones them and he talks to people and he thinks about them and he waits until exactly the right thing and he goes, "Yeah." And his hit rate is incredible.
Nahal 8:09 ↗
Yeah.
Rebecca Kaden 8:10 ↗
Um, and I think about, you know, someone like Fred who just the quality of his ideas Right. And and the the elevation he operates at where, you know, it's easy to go to an aboard meeting and be like, "What are your metrics, you know, like should the CAC be higher or lower? Should our payback be different?" And look, that's all important. That's the heartbeat of a lot of businesses and it's our job to be on top of it. But he's so good at being like, "Sure, sure, sure, sure, sure. Here's the elevation we're operating at. Here's an idea that is needle moving." Right. like this is what's going to really make this happen or not at the level we're talking about, not incremental. And I've learned a lot about that through him.
Nahal 8:52 ↗
Yeah. Amazing. Yeah. The story of uh I think Fred and uh Brad just had an interview on on the founding of USV and obviously legendary and um we you know inspires kind of everybody in the community. So it's amazing you get to learn that craft as as as you know as you said as apprenticeship with so close to those folks. Um, in terms of other people, what about founders? What about qualities in Do some of those same qualities extend to
Rebecca Kaden 9:20 ↗
Yeah, it's interesting because some of the same qualities certainly extend and actually some I think are really different, right, in a founder than an investor. And um I've learned a lot about I think there's there's traits about founders that I think are undeniably important. And then I think I've also learned over time and at USV our style is, you know, high conviction, low velocity.
Nahal 9:41 ↗
Mhm.
Rebecca Kaden 9:41 ↗
We're not going to invest in every company and we're not going to invest in every great company and that's okay. And
Nahal 9:47 ↗
how many deals do you do a year?
Rebecca Kaden 9:48 ↗
One to three, right?
Nahal 9:49 ↗
Per per partner, right?
Rebecca Kaden 9:50 ↗
So it's, you know, it's it's a consolidated model.
Nahal 9:54 ↗
Yeah.
Rebecca Kaden 9:54 ↗
Um, and we spend a lot of time indefinitely with the companies that we back, right? And I've also learned about the founders that are right for me to work with. And there can be awesome founders out there where they're not going to be the right fit for me and I'm not going to be the right fit for them. And that doesn't mean there's only one fit, right? But you got to know what kind of works. And I actually don't think it's the same among our partnerships. So there are people where I'll meet and I'll be like, "You're awesome. You should work with Albert, right?" You know, right? Um which I that's why you have a partnership, right? Um but yes, um I like spikiness. I like people who are super awesome and uniquely brilliant at something even if that means there are deficits.
Nahal 10:35 ↗
Yep.
Rebecca Kaden 10:36 ↗
And that they know it.
Nahal 10:37 ↗
Yeah,
Rebecca Kaden 10:37 ↗
I super value self-awareness. Um, but spikiness plus self-awareness, I think, is a really beautiful.
Nahal 10:46 ↗
Yeah.
Rebecca Kaden 10:47 ↗
Because then we know how to accommodate for, you know, where there are gaps and they're, you know, willing to do so, but they they excel at something. And I So that leads me away from I think there are founders that are awesome that are kind of steady.
Nahal 11:00 ↗
Yeah.
Rebecca Kaden 11:02 ↗
I like people that it's a risk on a little bit that are going to really go for it and spike. Um, I think I value um, ceaseless hard charging hustle a lot. I've learned that about myself. Maybe that's a fault of mine, too. But like I I love relentlessness.
Nahal 11:20 ↗
Just breaking through walls.
Rebecca Kaden 11:21 ↗
I love it.
Nahal 11:21 ↗
Yeah.
Rebecca Kaden 11:22 ↗
Um, I think that matters to me. Um, you know, the more I do it, the more I think pe You can't build a great company without a people orientation.
Nahal 11:30 ↗
Yeah.
Rebecca Kaden 11:31 ↗
um people that can't spot talent, that can't keep talent, that just don't have a feel for it. That is a hard one to make up for with other people around you.
Nahal 11:40 ↗
It has to be at the CEO level.
Rebecca Kaden 11:43 ↗
I can think of examples where it hasn't been in work. So, I know it's possible. I think it's very, very hard.
Nahal 11:47 ↗
Right.
Rebecca Kaden 11:48 ↗
Um
Nahal 11:48 ↗
always be recruiting.
Rebecca Kaden 11:49 ↗
I just think people that are talent magnets have such an advantage.
Nahal 11:53 ↗
Yeah.
Rebecca Kaden 11:53 ↗
Right. Like early on you just get this leg up.
Nahal 11:56 ↗
Yeah.
Rebecca Kaden 11:56 ↗
That others don't and it's hard to replicate that.
Nahal 11:59 ↗
Yeah.
Rebecca Kaden 12:00 ↗
And it really really matters. Um,
Nahal 12:03 ↗
yeah. It's interesting you say that one uh one way when I look at a founder and I when I get to conviction or not, it's like would I want to work for this person
Rebecca Kaden 12:11 ↗
100%.
Nahal 12:12 ↗
You know, and if not, then no [__] way.
Rebecca Kaden 12:15 ↗
Yeah. And it doesn't mean that they have to be awesome at everything. They just there's a magnetism that I think matters.
Nahal 12:20 ↗
Yeah.
Rebecca Kaden 12:21 ↗
Um I think the ability to operate at multiple elevations, right? So there the best founders that I've worked with are just incredible storytellers that like you they talk to you about what they're doing and you're like I see the future and it's real even when so many of the details of that future are so clearly still fuzzy but you're just like I hear it I see it like it's awesome even when you know so much is still to be worked out and requires kind of leaps of imagination and yet then they also talk about their business and they know the details cold and that's hard to do. Um, but playing constantly at multiple elevations I think is challenging and something that I've learned to look for.
Nahal 13:00 ↗
D Mothy 100%. Right. You talk to Dave, the coco of Ghost, and like you're like I see the future of retail and how inventory moves around the world and it's gigantic and you double click on it, you're like there's still a lot of fuzziness to it, right? But like you see it and then you ask him about what's going on today and it is so crisp and he's in the weeds and that's really hard to do. and that company's a talent magnet, you know, and that matters. Um, it's interesting you talked about kind of people that have spikiness and also the self-awareness. Um, so they know they have some superpower that contributing to the world. Um, while they have uh, you know, they're aware that they need to complement those with with other skill sets. Um, you are an incredible mom. I've watched you and by the way, you've got given me some great advice. uh on how to be an incredible mom as well. And uh I'm a dad. Um but um like how do you look at your raising your kids uh through that lens? Do you see them with certain, you know, I know they're super young. Uh our kids are super young, so maybe their spikiness hasn't yet shown yet.
Rebecca Kaden 14:15 ↗
No, I think you see it from the a crazy early age. Um no, I think about this a lot actually. I have two boys who are four and six and they're awesome and they're crazy. Um, yeah, I think about yeah, appreciating who they are and that their talents and individual spikiness can shine. And I've they've actually made me internalize more than anyone that your your best asset comes with your biggest flaw. And that's inherent that if I think about I, you know, my oldest son is um extremely outgoing. I was a I I'm an outgoing adult. I was a wildly shy child.
Nahal 15:01 ↗
Are you introvert or extrovert?
Rebecca Kaden 15:02 ↗
I'm a I'm a trained extrovert.
Nahal 15:04 ↗
You're an ambervert.
Rebecca Kaden 15:06 ↗
Yeah. I'm I'm actually like inherently an introvert and I've trained myself over many years to be extroverted.
Nahal 15:11 ↗
But when you're in a crowd, like when I see you at Well, it's interesting, right? I see you at like a dinner, you're very extroverted,
Rebecca Kaden 15:18 ↗
but I don't like a big conference.
Nahal 15:20 ↗
So, at conferences, you're like, "No way." But like I'd find a crew. But with your crew, you're like, you're the hit. You're you're the head of the party.
Rebecca Kaden 15:26 ↗
I'm very social. I I care deeply about my friends.
Nahal 15:29 ↗
Yeah.
Rebecca Kaden 15:29 ↗
I'm loyal. Um I love being around my friends. I prioritize it in my life, but I also need to get energy from going home, right? Do you know what I mean? Which I think is like part of the I I don't know. I think that definition might be fuzzier than people like it to be. But but when I was young, when I was my children's age, I was so shy. Um my nursery school made my mom record me speaking at home to prove to them that I could talk.
Nahal 15:57 ↗
Oh wow.
Rebecca Kaden 15:58 ↗
Cuz I refused to speak at school. And people who know me now are like, I don't see it. I'm like, I know, but I was really, really shy. And my husband was is kind of an introvert and was an introverted kid. Our oldest son is a wild extrovert. He just he's charming. He's outgoing. He can talk a crowd. Our feedback on him is always that he's, you know, oh wow, he's so charming. Oh wow, he's so conversational. He's not scared to go out to anyone.
Nahal 16:25 ↗
Yeah.
Rebecca Kaden 16:26 ↗
And also his his biggest opportunities to work on things and weaknesses are the same thing.
Nahal 16:33 ↗
Yeah.
Rebecca Kaden 16:33 ↗
And you just it's made me really appreciate that you don't get the spikes in people without the flaws and the things you're going to work on and that those so go hand in hand and that my job is to encourage him to be him and to emphasize those strengths and to lean into them and also to figure out how to manage the weaknesses that come with them.
Nahal 16:58 ↗
Yeah.
Rebecca Kaden 16:58 ↗
but not to change them because I think they would hamper his strengths and and how to do that which I think is easier when a child is a lot like you.
Nahal 17:07 ↗
Yeah.
Rebecca Kaden 17:07 ↗
And harder when they're not. But I've I don't know. I've enjoyed it. I mean, he's awesome.
Nahal 17:12 ↗
Is the four-year-old uh
Rebecca Kaden 17:13 ↗
much more like me. He's not He's not shy.

96 more exchanges in this transcript

Sign in free to read the rest of this interview. No card required.

Sign in to read the full transcript

Cite this transcript

APA, MLA, BibTeX
APA

Kaden, R. (2025, July 19). EP11 Rebecca Kaden [Interview transcript]. Human Unicorn Pod Official. CEOInterviews.AI. https://ceointerviews.ai/interview/3019492/

MLA

Rebecca Kaden. "EP11 Rebecca Kaden." Human Unicorn Pod Official, 19 Jul. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3019492/.

BibTeX
@misc{kaden2025_3019492,
  author       = {Rebecca Kaden},
  title        = {EP11 Rebecca Kaden},
  howpublished = {Interview transcript, Human Unicorn Pod Official. CEOInterviews.AI},
  year         = {2025},
  month        = {jul},
  url          = {https://ceointerviews.ai/interview/3019492/},
  note         = {Speaker-attributed transcript with timestamps}
}