Season 2 Episode 12
Caterina Fake, investor, serial entrepreneur

In the world of technology, there is often a prevailing mindset that, 'if it can exist, then it should exist.' But according to serial entrepreneur and tech pioneer Caterina Fake, this may not always be the case. As a maverick in her industry, Caterina asks the question, "Should this exist?" And if so, what is our ethical responsibility for making it available to the world?

Caterina Fake is known for co-founding the ground-breaking photo sharing platform Flickr as well as having played a pivotal role in the development of foundational AI algorithms through her company, Hunch.

As a member of Yes VC Venture Capital Firm, Caterina invests in pre-seed and seed stage companies, making a significant impact on the entrepreneurial landscape.

In today's episode Caterina joins us in-studio to share some of the early stories that shaped her career, mindsets that guide her creative ventures and her unique insights into the future and ethics of technology.

Pioneering as an early web designer

Chris Allen: Hey, welcome to the Entrepreneur’s Studio, Caterina. Thank you so much for making the trek.

Caterina Fake: Yes. Well, I have been enjoying Oklahoma City so far. It’s been lovely.

Chris: Did you try any food last night?

Caterina: That was the thing. I was going to arrive before dinner time, but then my flight was delayed and I got here late. So it was all a mini fridge for dinner.

Chris: Well, there’s much to enjoy. Glad you’re here. Thank you so much for coming. 

I think the thing I got most excited about when I heard the team was able to get in touch with you and that we’d be able to sit and have a conversation was the thought of, “This is somebody who has really helped shape a lot of what we do today.” A lot of the AI stuff that we’re doing today, you were there. A lot of the collaborative sharing and just the cloud, period, you were there. You probably get called this a lot, but you’re a pioneer, right? You’ve been doing development since the 1990s. How did you get started in technology that early?

Caterina: Well, what’s interesting is I didn’t come from a technology background. I have leaned on this a lot throughout my career. I actually think that this is one of my strengths. I come from a background in the humanities. I studied literature. I actually went out to California from the East Coast. I’m from the East Coast originally, and I came out to get a PhD in Renaissance Poetry.

Chris: No way.

Caterina: Yes, at Berkeley. So it’s a very unconventional path. And then, I was almost a little bit nerdy, geeky and I loved computers. I had a personal computer really early when it wasn’t that common. I think it was mostly because my dad had gotten it and I messed around with it and loved it. And here I was in the middle of it all in San Francisco in 1993, 1994 or 1995, and the web was blowing up. My very first job was actually designing CD-ROMs, if you remember.

Chris: Oh, I remember.

Caterina: I said, “Well, obviously this is going on. I’m not going to miss this train.” So I put my PhD on hold. I was like, ”Renaissance poetry can wait. It’s not going to change that much in the next 10 years, but this is happening right now.” 

It was so exciting, and you could feel this was changing the world. You knew it. I felt like I was one of a few people. There were just a hundred people who knew about it. It was kind of incredible. So I hopped on there and I got involved. I was working as a web designer, as one of the very first web designers, and it was before anybody even knew what web design was. It didn’t really even exist. You had to teach yourself by reading source code. And I did that. Then it was just an unstoppable juggernaut.

Chris: You just kept going.

Caterina: Yeah. It was amazing.

Chris: So roles you typically played early, were you truly a coder or technical person, or did you end up being on the go-to market side or operations? Where did you show up when you were starting these companies and they started to get some product-market fit?

Caterina: Well, my background was in design. I came as an artist. I was a fine artist. And I realized I had a lot of skills that could be used in the digital world, but I thought that was very important actually as a product person, which is where I kind of ended up as someone who knows how to code — and we’re talking in the very early days. So it was like basic HTML, JavaScript, CSS, that kind of thing. I could learn that and master that, because I thought it was very important to be able to work with people and understand the way the technology worked. So I never just slotted myself into one area. I always found it was really important that I learn all of the different aspects of it. I didn’t have to be an expert.

I didn’t have to be the one you would hire for that job, but I had to understand it because I was working with everybody on the team. Then gradually, eventually, I ended up being head of product at a couple startups that faded away, and then became the main kind of designer or product designer, creator, co-founder of Flickr. Then at that point, I did everything. I was a jack of all trades. It’s like an entrepreneur’s job. You have to be able to do all the things. So I did all the things.

Chris: You did all the things, and all the things seem to be, a lot of your work has, I would say, a pretty unique intersection. It’s at the center or the intersection of art, technology and community.

Caterina: Yes. I would say that’s true. Creativity, self-expression and then platforms for those things. So yes.

Chris: So for others to take part, and creating experiences is a big thing. If there was a theme in your career, I’d say it relates to your product leadership. Gosh, in the 1990s when UI (user interface) wasn’t even a thing.

Caterina: There was no UI.

Caterina: If you go online and search for internet 1996, you will see one of my very early designs, pre-design, pre-interface, like you say, for

Chris: Oh my gosh.

Caterina: It’s crazy. Yeah. Because one of the very first jobs I had was at Organic Online. They had spun out of Wired Magazine, and they had all of these customers who wanted to have their first website. So it was literally the first website for Levi’s, the first website for McDonald’s, et al. That was what I worked on, these very, very, very early first websites for these companies. Even the Yahoo website.

Chris: Yeah. What were you designing on?

Caterina: You mean the computers?

Chris: Yeah. Today, you have XD—

Caterina: What the heck were we using? We were using Macintosh Quadras, if I’m not mistaken.

Chris: It’s like early Figma.

Caterina: Some people were on Silicon Graphics, which is a really big deal. Those were very expensive, like workstations, but I think we were on those really early Macs.

Chris: Wow. Wow. So it’s cool.

Caterina: And I also remember seeing the first Newton.

Chris: Oh yeah.

Caterina: The Apple Newton. A friend of mine at Organic where I worked, she brought in hers and it was amazing. It was like the first iPod.

What it means to be born an entrepreneur

Chris: Yeah, first time seeing it. Well, the thing I always am interested about with people who have such a, I’m going to say high-impact trajectory like you’ve had, is what is the thing that was the spark? What sort of sparked your trajectory? 

Caterina: It’s like the part of the Bible where it reads, “Some are born entrepreneurs, some are made entrepreneurs, and some become entrepreneurs for the kingdom of God.” So I think I was born an entrepreneur.

Chris: Really?

Caterina: I actually think I was born an entrepreneur. I always heard this from my dad, from a very early stage. He said, “You are a self-starter. You are not governable. Nobody can be your boss. You are self-taught. You are unafraid of going out on the skinny branches and taking risks. You should be an entrepreneur.” He always said this. He’s an insurance executive. He’s kind of the opposite. It’s like the world’s most secure job in the world about security.

Chris: Yeah. Well, we build portfolios. We don’t build technology yet.

Caterina: Exactly. And yet, I manifested a lot of these characteristics really early on. He said, “You should always work for yourself.” And that was definitely true. I would find myself in a job when I was young, and I would be like, “God, how can I get out of here?”

Chris: What am I going to do?

Caterina: How can I be my own? I want to be the boss.

Chris: But see, the thing is you figured out how. You’re like, “How can I get out of here? And then what problem can I solve to help somebody? And how do I monetize it?”

Caterina: Exactly. And if you have that, if you see opportunities and think that for whatever reason… I had that even as a little kid. I remember my mom pointing out that my neighbor’s kid had this business. I was very impressed with this. At the local high school, he had command of his mom’s car, and he was able to drive down to the deli and buy a whole bunch of sandwiches so people didn’t have to eat the somewhat terrible cafeteria food. Then he would sell them at a markup every day to all the people out the back of his mom’s car. I remember being very impressed with this.

Chris: You’re like, “There you go.”

Caterina: I’m like, “Okay, this is how you do it. This is an opportunity.” He was kind of a born entrepreneur. So you see these things and you’re like, “Huh, I could do that. There are some possibilities there.” And you see these kinds of gaps where you can go in and make a difference, and make some changes.

Being passionate about the early stages of startups

Chris: Yeah. You’re a serial entrepreneur, which is just over and over again, but is it the spark of the idea that gets some traction? Or is it seeing something born into the world that’s going to have a legacy or that will last? What’s the thing that you’re like, “Man, this is the part of business that gets me going.”

Caterina: It’s definitely about the very early stages. The very early stages are like that exactly. I mean, I have notebooks full of business ideas that are unrealized because you just see them everywhere. If you’re looking, if you’re spending the time and if your brain works a certain way, you see them all over the place. So you see those early opportunities. Some of them work, some of them don’t. You try them out, they fall flat, they don’t work out at all, the market’s not ready. You’re too early, you’re too late, whatever the thing is. But if you’re on it and you’re seeing it, and you just execute it, then you can make a prototype, and then you can build a team, then you can hire some people, and then you can get some customers. I love that part, the really early part.

And you said pioneer earlier, I’m definitely a pioneer and not a settler. Once it comes time to settle, I’m not good at that. I don’t know. I’m a good advisor. I’m a good board member. I’m a good late-stage strategist. I know a lot of people. I know a lot of people in the business. I can make introductions. I can help raise financing. I’m a VC myself now. And I think the ecosystem can benefit from a lot of those things. The entrepreneurs who I work with can benefit from a lot of that background and the work that I do. But as for myself, I just love the early stage.

Chris: Yeah. A lot of spark there. There’s a lot of spark as an advisor too, right? Because you can come in and have fresh eyes and say, “Hey, wow, here’s a pretty clear thing you could give a shot to.” Right?

Caterina: Exactly.

Detecting areas of need and creating savvy solutions

Chris: And you don’t have to be the person to bring it to life. Well, okay, so let’s just back up, because Flickr, pretty much everybody knows what that is. Talk to us about that stage you just talked about that was so exciting that you still love. Take us back to how Flickr was born.

Caterina: So I came from a background in blogging and online communities. I had been involved in a ton of online communities leading up to this, including old, original gangster (OG) communities like The WELL (Whole Earth ’Lectronic Link).

Chris: Okay. OG.

Caterina: OG. Actually, that may be the OG.

Chris: I know.

Caterina: That may be the original-gangster online community, if I’m not mistaken. Because it was on BBS (Bulletin Board System). It was pre-web. I love that because this was actually where my roots came from. My roots were in online community, and I came from BBSs because when I was in college, I had access to the internet, which was very rare during that era. 

I found online communities around the world. I was really into Jorge Luis Borges, the writer. And I found a community of Borges’ Scholars in Aarhus, Denmark of all things. And so it was online community. It was a magic thing. It was a spark that lit up. I could find people who shared these obscure interests of mine, because I had very obscure interests, and then meet them online. So online community was the main thing. And Flickr was just a natural evolution from blogging to photo sharing. And at the time, the big photo-sharing sites were oPhoto, Shutterfly and Snapfish, all of which were, I would call them derivatives of a pre-digital world. They were like photo albums. They had all these metaphors that came from the real world, so to speak.

Chris: Analog world.

Caterina: Analog world. They were kind of like horseless carriages. The horseless carriage is what they used to call the car, right? The horseless carriage. It was like they were horseless carriages. Whereas I think Flickr was the first digital-native photo-sharing site. That’s how that came about. It came from the convergence of a lot of things. One was that at the time we were building it, Friendster already existed. So people were accustomed to making an online profile.

More than half of cellphones shipped with a camera on it, which was a new thing — even in 2003. Then more than half of US households had broadband, which meant you could actually upload them without using dial-up internet. So those things converged, those things happened. And as a result of that, people did not really know where to put their photos and did not have a place to put their digital photos. And they did not have a way of sharing those photos, other than via these somewhat kludgy, awkward photo-sharing sites.

Chris: Like file transfer, all that kind of stuff. Nobody had access to servers and stuff like that.

Caterina: No, no. I mean, I did because I was a power user. But unless you were too, unless you were a person who knew how to set up a server—

Chris: It wasn’t democratized.

Caterina: No. So that kind of paved the way for all of these platforms.

Maintaining a beginner’s mindset

Chris: Well, I wonder, tell us maybe a little bit more about why maybe collaboration and sharing ideas is so important as it relates to being an entrepreneur.

Caterina: I think it’s crucial. I mean, I think you put yourself in the middle of flows of information and meeting people and being curious and learning. I think being an autodidact and self-taught is a big part of entrepreneurship actually. That’s a huge part of it. I think that’s why I have been successful as an entrepreneur, because I always had that tendency. I was not a good student. I didn’t do well when I was given assignments. The difficulties of raising an anarchist. My dad found it really hard to keep me in school and to care about my grades because I just had all my little side projects. I loved to make things and do things and create things on the side. 

School was just... I benefited hugely from school. I mean, I stayed in school, I graduated from college, I did all the things, but it was not my primary motivation. I didn’t get a lot of satisfaction out of getting good grades. I got good grades-ish when I put some effort in. But I really honestly think that most of the things I learned, I learned on my own. So as a result of that, you can kind of take on anything. I feel pretty confident.

I mean, we’re doing all of these investments now that are not related in any way to our prior work. But if you’re the kind of person who can quickly get up to speed, and you are humble enough to go into learning mode so you don’t feel like you have to be the one who knows, but can be the one who learns…that’s the thing about technology — it’s constantly changing. So unless you have that mindset that you can be the one who learns and not the one who knows and you can look at things with a beginner’s mind, it’s a huge advantage. A lot of the problems with serial entrepreneurs who fail their second or third attempt is because they feel like they know and they don’t know. Because everything changes so fast. Everything changes so fast. And I mean, look at us here today. Last November, chatGPT was released. I mean, look at it. Look what’s going on right now with AI.

Chris: Yeah. It’s all over the place.

Caterina: It’s all over the place. I mean, it’s everything. It’s everything. It’s like climate, carbon removal, RNA therapies, you name it, satellites, space. I mean, it goes on and on. And so unless you’re willing to be constantly learning and constantly changing — if you want to settle rather than be a pioneer, it’s just a different mindset.

Sharing your ideas and learning any way you can 

Chris: Yeah. The connection I’m making in the conversation is that you have notebooks full of ideas, many of which have no action, some of which do, some of which have tried and failed, some of them have succeeded. And if you talk to someone who is a first-time entrepreneur or thinking about it, many of the times that I talk to these people, they’ve got one idea and they are safeguarding that idea, and they don’t want to talk about it or they’re nervous to talk about it because of some sort of scarcity mindset or whatever. So the thing with you is, of all of the side projects and all the things you’re doing, all the things you’ve been able to bring into the world, if you see that kind of behavior, what are some of the ways you would either coach that person or what are some of the ways you would encourage that person? Or what are some of the things you say to early-stage entrepreneurs who are first-time entrepreneurs?

Caterina: Your first idea is rarely your best idea. Sometimes it is, sometimes you have total conviction and you’re like, “This is the one.” But it’s usually somebody who has gone through a lot of ideation already, and then they know that’s the good idea. So they’ve tried out different things. They’ve built, I don’t know, prototypes. I mean, you can do things like Google Ads A/B testing, like this or that, I don’t know. Then you just throw up a webpage for two different products, and you run a hundred bucks worth of Google Ads against them and see which one people actually respond to. Then also at the same time, you can collect email addresses for when you launch and you’re like, “I already have a customer base.” I mean, that’s what I would do. I think that’s the way to get out of that scarcity mindset, and the thought of, “I only have one good idea.” Deliberately and purposefully go into situations where you can say, “I’m interested in this area. I think there’s a lot of opportunity in this vertical or category or industry.” And go put yourself in there. 

Then literally just do a brainstorming exercise. What are the five things that are needed here? Where is there a lack? What is changing in the world that is going to affect this industry, this category, this particular vertical? What is it? Then come up with five ideas or 10 ideas, and then literally do that. Drop a plan for each of them. A/B test them on Google AdWords. I mean, on and on. You talk to your friends, say, “Hey, this, this or this, what do you think?” Talk to them. Go find somebody in the industry online. It’s the internet. You can get in touch with anybody. Like, “Hi. I see that you’re into hydrogen. I think there’s a huge opportunity here. And here’s the thing. What do you think of these five ideas?”

Chris: I love that.

Caterina: I do that. I mean, I don’t know. I used to do this all the time. So I had this brief period when, this was before Flickr, I was kind of sick of startups at that point. It’s interesting. Talking about things like, “Ah, it’s 2000, startups are over.”

Chris: Little did you know.

Caterina: And so I’m like, “Oh God, do I really want to do this anymore? It’s such a struggle. Can’t raise money. It sucks.” So I decided I was going to do something completely different. I come from an arts background. I like materials. I like fashion. I was going to start a fashion company. I realized that actually learning to sew clothing was impossible. There’s no way I was going to learn how to do that.

Chris: I can build web pages.

Caterina: So I was like, “Handbags, I’m going to make handbags. It’s something I can do.” So what I did was I was living in Vancouver at the time. I sent out an email to 10 different clothing companies online. This is how an entrepreneur is. This is how an entrepreneur works. I sent an email out to 10 clothing companies that were based in Vancouver. Nobody responded except for one. I offered myself as an unpaid intern because I never even worked in retail. How do I know how to make clothing? Zero. I said, “I will work for you for free.” This was my offer I sent to these 10 companies. “I will work for you for free for three months, so long as I can attend all your meetings and ask you questions for a half an hour a week.” That was the deal. I will work for you for 20 hours a week for free.

Chris: Labor for information.

Caterina: Yup. So one of them responded. Jacqueline Conoir was the name of the company based in Vancouver. So I go and I work as a shop girl on the floor, in the warehouse. I attend all of their meetings. And by the end of, I didn’t even stay for three months, I stayed for two months because I got all the information I needed. I knew how to source fabrics. I knew how to hire sewers. I knew how to pitch to Bloomingdale’s and all of the department stores, because I had attended all of those meetings. I knew how to do basic design.

I knew how to spot trends. I knew how to address a demographic and a customer base. And I knew exactly how to build a clothing company, a fashion company, which after two years, what was so interesting about that is I also had a bunch of friends who worked as fashion designers in Canada, there in Vancouver. And they were calling me and asking me questions. I was like, “You have been a fashion designer for three years, four years, five years. You graduated from college. You have a degree in fashion. How come you’re asking me?” I started learning this two months ago. Just go do what I did. And so—

Chris: That’s the difference between learning the skill versus learning the business.

Caterina: Right. And whatever, I had the humility to go and get kicked around by all the shop girls. They said, “Steam, iron this, put this on the truck,” whatever. I did all that work. It was like grunt work. But in exchange, I got all of that information and knowledge about how to build this. I never started. I started a handbag company because then I started Flickr, and then that happened. But what I’m seeing is that there is no category that I don’t feel I could learn. I could go into shipping and logistics. I could go into audio equipment design, I could go into satellite systems, etc. And I feel confident I could figure out how to get myself in there and learn what I needed to learn and then start a company in that industry. Do you see what I’m saying?

Chris: Yeah, I do. I do. Basically, you’re like, “I can go digest how to do something in an industry, a category, a vertical,” whatever, because of the skill you’ve learned, which is observation, feedback, synthesis, all that kind of stuff. But it’s basically like—

Caterina: And daring. And daring, because I think a lot of people are afraid to do that. They’re afraid. They’re afraid people are going to reject them. Everybody rejected me. I didn’t care. But somebody said yes, somebody said yes. And all you hear are nos. And when you hear a yes, you go after the yes as hard as you can. Somebody will say yes to you. And it’s important for you to go after your yeses.

Chris: I love that. Well, I think something important I’ve seen as a theme is just, especially with AI coming out, there’s this sort of ethical line that is interesting, and all the exploration, all the discovery you’re saying you’ve been able to do, you’ve done, you’ve actually taken swings and things like that. There’s this kind of undercurrent of are we doing the right thing? Right?

Caterina: Yeah.

Innovating in a responsible fashion 

Chris: So let’s say with Hunch, it’s kind of like a precursor, if you will, and Flickr to Yahoo, Hunch to eBay. What are some of the things you’re thinking about when it comes to AI? And what are some of your concerns or some of the exciting ways we’re using it or how people intend to use it?

Caterina: So for a little bit of background, Hunch was an AI company that was started in 2008. And basically what happened was that Flickr had been acquired by Yahoo. While I was at Yahoo, I started working in search. We knew search was informed by your social networks, this was in 2008, and that it would be much more powerful because we would know what you liked, what you cared about, what was important to you, and then were able to actually serve you things you wanted. So there was a very strong motivation to build products like this. And that was where Hunch came from. That was kind of a lot of the thinking behind it. “We have a hunch that you’ll like it” is where the name came from. But we saw this same technology being abused. This is where Cambridge Analytica came from. This is where Palantir came from.

Basically all of these people harvesting your data and using it in ways you don’t agree to and approve of. And in the very early stages of that company, it was very obvious to us that abuse was very easy to take advantage of. People were naive, people were trusting. Mark Zuckerberg was on the cover of Newsweek. Everybody trusted him. And nevertheless, to me, it was very clear this could be a source of incredible abuse because the things that were happening at that time were that you could pay your way to get in front of somebody. They would suppress the community you had built on Facebook. They would surface things that were the most kind of outrageous or scandalous or sensational in order to get you to come back. So discord, you could make half the country hate the other half of the country.

It was a very kind of terrible time because you could actually see it coming before the rest of the world was catching up. So what we were doing at Hunch, it’s very interesting because we started off from the principle that you own your own data, you can take it and you can remove it. You can see whatever we’re doing with it, and we won’t keep that a secret unlike some of the other platforms. The other thing that was very important was that we didn’t want you to be in a bubble. There’s a book that came out at the time by Eli Pariser, which was called “The Filter Bubble”, where if you just hear things that reinforce your own viewpoint and you never hear any kind of dissenter like, “Huh, maybe that isn’t the way things are,” then you end up with everybody becomes flat-earthers or anti-vax or whatever the thing is. There’s a thousand things. And you can start to have these...what used to be fringe beliefs reinforced and then have them become—

Chris: And then they become mainstream.

Caterina: And then they become mainstream. Exactly. So you could see that happening. When I was building this kind of company very early on, we could feel and sense and see this happening. So built in these things, for example, I had designed this thing, this feature of Hunch, which was called a Wild Card. We knew what your belief system was, your political orientation was, who you were. To get you out of your filter bubble, we would deliberately introduce things that were outside of that. So if you were super right wing, we wouldn’t throw you Bernie Sanders. We would kind of edge you out, kind of edge you out a little bit from where you were, a little bit out of your comfort zone, right?

We would present you with things like, “Here’s another way of thinking about things. Here’s another way of thinking about things.” And it would be labeled as such so that you didn’t think it was broken, right? It’s not giving me the things I thought I was going to get. So it would keep a balance. It was very deliberately designed that way to be the opposite of what a lot of the other social platforms were doing. I thought this was hugely important, and I thought this was one of the things that AI was very dangerously kind of pursuing as a direction and did what I could product-wise to counteract it.

Chris: That’s amazing. And you can really see just the thinking and even some of the ability for something like Hunch to really come about. A big part of your superpower is listening, observation and synthesis.

Caterina: Yes. And being user focused and thinking about the people who are on it, communities, how people work together, how to create communities, how to get people to include people who they wouldn’t normally include. Because that’s what a community can do. It can make room for people who are different or other, or somehow not part of the core. That’s what a community, a good community, a healthy community can do.

Living with purpose and pursuing knowledge as a lifestyle 

Chris: So all the things we’ve talked about so far, we’ve got the art, the community, the technology, we’ve got the ethical approach to business, your superpowers of listening, observation and synthesis. There’s something that’s in the bedrock of who you are. What is that bedrock as it relates to your mindset? 

You mentioned your upbringing, but what’s sort of the thing that you point back to or that you refer back to, which is kind of the undergirding support for all of those things about who you are as a person and an entrepreneur?

Caterina: I think that from my very early life, I have always wanted to engage in, what I would call, noble pursuits. So when I say noble pursuits, it sounds very grandiose. It sounds very like highfalutin.

Chris: It could be purpose, yes.

Caterina: And it is purpose. But I do think I have lived my life in such a way that I have always tried to avoid certain things, especially in the things I think about, the things I interact with, the things I absorb, the people who I spend time with, I have been very deliberate about all those things. That has given me more than can even be explained. An example of that would be that I I came from Renaissance Poetry, but that didn’t start there. When I was about 10 years old, at some point, I had this idea that poetry was perfected language. It was the most beautiful language.

It was the most beautiful human expression, and it was the very height of human expression. So I started memorizing poetry because what I wanted was for the poetry to be part of how I spoke, how I thought, and how I was. It was a pursuit of a kind of wisdom. I started this at the age of 10. I only read books I felt were notable in some way, that had some kind of art to it, that had some kind of nobility to it, that had some kind of hurt to it, that were soulful, that were real. I didn’t read airport entertainment. I only read great works.

Chris: The deep stuff and the great works.

Caterina: The deep stuff. This is what I call — and this is from childhood, a noble pursuit. It’s the same thing with movies, and the same thing with, I mean, everything. I am always learning things. Right now, I am learning French. I decided in my kind-of old age to just learn a new language. I mean, I started it off in high school, so I have high school French, but I started learning French about three years ago. I switched all of my podcasts and all my media and everything, even my newspapers to French media. That kind of thing. And I do that kind of thing all the time.

So whether it be studying languages, studying music, what have you, I have always done that. I can’t even tell you how profound of a difference in my life this has become, because I have read a lot of the Western canon. I have read all of the books. I have read the Gnostic scriptures, I have read the Quran, I have, of course, read the Bible. I’ve read all of Shakespeare. I mean, it’s just like that. This is what I do. And I spend several hours a day on this. And once you have done that, you have such a base of what is important in life, what makes you human, what is important about society, about culture, about community, about technology, about what we’re doing in the world. And once you’ve got that in your system, it just flows out into everything you do.

Chris: Yeah. That’s good. That’s good. I think the synthesis part is really, really huge. And also the thing that you were just talking about is maybe what do people around you, when you make that switch from all of the things you just said to French around you, are the people around you like, “Okay, this is changing”? Are they pretty adaptable?

Caterina: I mean, people who know me well enough, they’re like, “Here she goes again with a new thing. She’s no longer learning how to play the guitar. Now she’s learning how to speak French,” or whatever the thing is. I mean, and I just do that as a habit. If you can create great habits like that, reading an hour a day of something great and hard stuff. I deliberately put myself into situations where I’ll have to do those hard things. For example, three weeks ago, I interviewed Michio Kaku, and he is a quantum physicist. Let’s be honest, I do not know very much about quantum physics. Do not. I never spent any time studying it. But I had been asked to do the interview, and I accepted it because I knew I would be forced to read about quantum physics and have some kind of basic understanding of it so I could interview him properly and have a good sense of who he was and what his work was about.

And quantum computing, of course, his book was about quantum computing, which obviously has a lot to do with our industry. So what I’ll often do is I’ll put myself in those situations where I’ll be forced to, because I remember, as it was approaching, it would’ve been six months before I agreed to do it. As it’s approaching, I’m like, “Oh no. Now I have to read quantum physics for the next two months just to understand what is going on.” 

But it was good. Now I’m conversant in the basics of quantum physics. I went down to Google, I talked to Hartmut Neven, who is the Google head of quantum computing there. I did all that. And it was an onstage interview. It was an hour long. But I felt like I had to rise to the occasion. I had to do a good job, and I had to learn something about it. It only benefited me because now look at me now. I have this further dimensionality. I feel like I could make investments based on quantum computing, the principles of quantum physics. So there you go.

Chris: Well, all the stuff you just said doesn’t have a lot of thank yous or awards. It’s not like you’re a musician and you’re going to be able to win a Grammy Award as an entrepreneur. Right?

Caterina: No.

Chris: You know what I’m saying?

Caterina: Well, that’s the thing too, is that—

Chris: What is the award system for you? What is the thing that’s like—

Caterina: There’s no award. It’s all intrinsic. And I think this is one thing that has always driven all of all the people in the institutions where I work crazy. Because I don’t fight for prizes not worth winning. I don’t see that collecting a lot of trophies and ribbons and awards and this and that are worthy pursuit. It’s nice. I love getting awards. I can’t deny that. I have two honorary doctorates from Rhode Island School of Design and from The New School in New York. And that’s great. I love it. It makes me feel very proud that they would honor me in this way. But honestly, I don’t need those things. I would do it anyway. I would do all of the things I do with no rewards, just because it’s fulfilling and it’s soulful and it’s what makes you human.

Chris: Yeah. It matters to people. We talked about the stages of a business and we talked about the entrepreneur and the single-idea kind of entrepreneur. You have the three stages of startup and then you kind of build it up and then you scale it up. Very HubSpot language, but now you’re a VC. So what are some of the top three or four things that you would say, “Hey, this is the stuff we pay attention to and here’s why, and here’s some recommendations,” that you would make to anybody who’s ready to do a startup? What are the things you look for because I know you talked about themes, categories, things you invest in, but then you mentioned earlier we’re investing in stuff that has nothing to do with our prior work.

Caterina: Zero. Yes.

Using founder resilience to evaluate early-stage startups 

Chris: Yeah. So what are some of the things you kind of look for to say, "You know what? This is worth the investment”?

Caterina: Well, I’d say the first thing is, since we’re early-stage investors, we are very much about the entrepreneur, the entrepreneur, him or herself, and how they think, how they present, the way they are. You gave a really good example of an entrepreneur we would not necessarily want to invest in, which is the one who’s kind of hoarding their information or their idea and hiding it from the world. Because chances are everybody else has had the idea at the same time. There’s thousands of accelerators around the world. Somebody’s creating it. Somebody in Kyoto or in Tel Aviv is actually probably working on the exact same idea, not to mention Silicon Valley.

So I do think that kind of being stingy with your idea is actually kind of a very bad sign. You want somebody who’s kind of expansive, who is meeting people, who is asking questions and then somebody who’s also, I think, very reality based. Like, “Okay, we tried this and it failed and we’re going to try something else.” Because I think a lot of people get attached to their idea. Now, that’s not to say some people don’t let their idea ride out far enough. That’s another issue. They just flip. Other people flip through various ideas, one after another and never settle on one and never really commit. That can also be an issue. But I think that when you find a founder who has founder-product fit, you can feel it and you can also feel it because there’s a feeling of a train, find a parade and get in front of it. There’s a feeling that they’re being propelled by something external to themselves.

And I do think one of the most important things for an entrepreneur is to be working on the correct thing. It’s really funny because you know how they have these little Pinterest things with a quote. One of my quotes, it’s always floating around, is “working on the right thing is more important than working hard”. And that’s so true. I think that a lot of people just think, “If I just use enough brute force, this idea will work.” But maybe you’re just working on the wrong idea. That’s it. Then the other thing too is I think somebody should be sufficiently humbled to be able to know what they can do and what they can’t do, what they’re good at, what they’re not good at, and to do the thing they’re good at. And then finding people to surround themselves with who can do those other things.

Also very important is I think the resilience and the drive that helps those people stay up all night, obsessed with their idea, people who are able to get knocked down nine times and stand up 10, that is crucial. I do not think that entrepreneurship is right for most people. I really don’t. I think there’s a lot of people who it just seems like a cool thing to do, but it’s so hard and it’s so discouraging and it’s so humiliating and it’s so whatever, just beats you down that you really have to want it and you’ve got to really be able to kind of pursue it. Now that said, that is a kind of VC-backable growth stage. You have to be able to build a $100 million, $1 billion-dollar company and you have to want to do that. That is not to say there are not any non-venture backed entrepreneurs. There should be thousands of them. In fact, they should be most of the entrepreneurs who are out there, not seeking venture capital.

Chris: Bootstrapped.

Caterina: Bootstrapping, friend and family funded, funded out of revenue from your bakery or from whatever the thing is you wanted to start your nail salon. It’s not to say that those aren’t equally valid and possibly even more valid companies than the ones seeking venture capital. But I do think there’s a difference. I do think that unless you really want to be in the really hard and brutal world of venture-backed entrepreneurship, you should really reconsider.

Understanding the relationship between timing and success

Chris: I like all the different avenues of investment you just mentioned. I would say venture backed and private equity are really, really hard. And the thing I like that you said really eloquently just a minute ago, is that where you’re looking to invest is less about the idea. And then you’ve got the people and then you’ve got the business and you’re like, “I’m going to invest in the person of the entrepreneur out of the belief that there’s proof or evidence that a business could be born.”

Caterina: Yes. However, there’s one caveat to that basically, which I always think about. This is because it really stuck in my mind. Bill Gross, who started, I forget the name of his organization (Idealab), but he incubated in the 1990s. He had one of the first incubators, it was called an incubator, not an accelerator then. And he started hundreds of companies, 500, 800, I don’t even know, maybe 1,000 companies. Then he went back and he looked at the ones that succeeded and the ones that failed. Of course, it was a small number that succeeded. So he looked at all of them and he thought, “Was it the entrepreneur? Was it the market? Was it the execution? Was it the timing? Was it the funding?” Of these five aspects, I think those are them, which are the things that made them succeed? Do you know what it was?

Chris: Which one?

Caterina: Care to guess?

Chris: All of them.

Caterina: Timing.

Chris: Wow.

Caterina: Number one, timing, more than anything. They had the right idea and at the right time and the momentum around them, this is why I say find a parade and get in front of it, the world is flowing in a certain direction. There is momentum, there are people who want this to happen. There are people who want to work for a company where this is happening. There is a societal push, there’s a culture change. Something is happening in the world that is propelling this idea forward. That is number one. So our job as VCs, I think, is to identify what those things are.

What are those categories? What are the things that have all of this propulsion behind them that you just stand in it and you’ll flow. You’ll go, you’ll be carried away. It’ll be like a river. You need to be good and you can’t just like... Anyone can take the helm when the sea is calm. So if there’s some kind of rushing river of opportunity, you need somebody who can ride it. You need a good entrepreneur and you need a good team, and you need the right financing, and you need the right marketing. And all those things are important. But number one, timing.

Helping co-founders avoid future conflict

Chris: I love that. And I wonder about your conversations with founders... Actually, let me go here first. What’s your stance on founder plus co-founder?

Caterina: I think co-founders are always better.

Chris: Yeah.

Caterina: Yeah. I’ve been both and co-founder’s better.

Chris: You’ve got to have both.

Caterina: And it’s tough. I mean, it’s just tough to find a co-founder. It’s really hard to work with people.

Chris: There are a lot of accelerators that won’t even entertain you to be a part of their program unless it’s founder/co-founder.

Caterina: Yeah, founder/co-founder. I think it’s important. And like I said before, you know what your strengths and weaknesses are, you’ve compensated for them, you are complementary and it can be a really fraught relationship. I mean, at Yes VC, we have a thing called Founder Charter where we actually have everybody sit down. It’s a little bit like pre-marriage counseling where you sit down and you agree on, “Okay, you do this, you do that.” You can get through a lot of the hidden assumptions and places of future conflict.

You can plan things for moments such as what if you have an opportunity to sell it and one of the co-founders doesn’t want to? What if somebody gets very sick? What happens to the company then? Who ultimately decides on the engineering decisions versus the product decisions versus the marketing decisions? You work it all out in advance. We have a list of all of these kinds of things called the Founder Charter, and it’s great and you can tease it out and get through a lot of the things and realize where your areas of disagreement could possibly be and so on. I mean, we actually had founders run through it, and then one of them came by later and said, “You know what? I don’t think I want to co-found the company with him.”

Chris: I mean, it’s a worthy cause.

Caterina: It’s worthy. Anyway, because you’re in it. And this has got to be a person you can go up and down with and have lots of trust in through a lot of chaos.

Chris: You answered it in a pretty good way as it relates to the Founder Charter. I wonder, can you sit in front of an entrepreneur and then how many questions and how much time do you need to know that there’s a there there?

Caterina: One thing that’s interesting, and my partner, Yuri, says this all the time, is that when you meet with a VC, they already know if they’re going to invest with you. They already know if they’re going to invest in your company. Is that true always? No. But to a large extent, if the VC has done their job, they know the category you’re in. They know who you are and what you are like. They understand the industry you’re trying to get into. They’ve seen your deck. And so they understand what your strategy is. So a lot of the time before you even sit down with them... because once you get somebody’s deck and you have kind of a sense of that, you have a really good idea of whether you like this company or not. Then it happened all the time where I’m like, “I’m not going to invest in that.” Then I meet the founder and I’m like, “Yes, I’m convinced. I now understand something I didn’t understand before, or something about the industry I didn’t understand before, some opportunity I missed.”

Chris: Did you give them feedback and be like, “You didn’t sort of make the case in your deck”?

Caterina: Yeah. You kind of changed my mind. The opposite has also happened where I’m like, “Ugh, this is the one. Oh my God, this is great. Where do I sign?” And then you meet them and you’re like, “Nah, I’m backing out of that one.” So it can go both ways. It can go both ways.

Chris: Yeah. Yes VC is up and running. How many investments have you guys made?

Caterina: So the first fund was 23 investments, and the second will be, or in the very last year of the investment period will be 30. So there’ll be 53 companies. Then we’re raising fund three, which will be coming up probably towards the end of this year.

Respecting the value of CEO-board member communication

Chris: Yeah. So you’re doing that and you’re learning French, and then you have a couple of board seats and some advisor seats as well. I think it would be good to just unpack a little bit about those positions. Let’s say there’s a CEO who has to deal with the board all the time and has to get the board to buy in. What are some of the things you would encourage founders and CEOs to really take stock of while they’re engaging with the board?

Caterina: I think it’s really important to be in constant communication with your board. I think you can’t be one of those CEOs who just sends out a deck the week before the quarterly board meeting and then only talks to your board then. You should have a strategic purpose for each of your board members. You should say, “This person is strong in finance. This person is strong in marketing. This person is strong...” You have a board. Know what the strengths are, know how they can help you. Make asks of them and be in constant communication. Before the board meeting, you don’t want everybody to show up and then be like, “Sales are down 37%.” You don’t want that to be a surprise. You want that to have been part of the conversation. “We’re seeing this fall in whatever our revenues for this reason, I think, can you help me with this? What do you think?” You know What I’m saying?

So I do think that kind of back and forth is important. Then I think the worst board meetings are the ones where they’re just kind of passing on information and you’re just looking at the numbers and you’re kind of just being updated. That’s not useful. What you want to do is always have a very strategic purpose of problem solving. Roll-up-your-sleeves, participatory board meeting whenever you can. Not every board meeting can be that way. Not every board member is the kind of board member who can dedicate that much time or energy, and that’s fine. You can also have board members who are more like rubber stamps or there for some purpose because you know they have access to future capital, whatever the reason is.

Chris: Future capital, other relationships.

Caterina: Exactly. They’re exceptionally good recruiters. They have a really good kind of base of knowledge in, I don’t know, space or satellites, whatever the thing is. So not every board member has to be that way, but you should really know how each board member can help you and then use them and really develop relationships with them. Go out to dinner with them, have coffee with them, talk to them, etc. Because it’s a very lonely job to be a CEO, horribly lonely. You’re kind of constantly having to build a team. You’re constantly having to present and be that person everybody’s listening to and trusting and depending on, and it’s a job where you need support and you need people to be able to communicate with and talk to you. Your board should be able to do that for you.

Chris: What is maybe a trait of a CEO you’ve seen over and over again? As in, the successful ones have this factor.

Caterina: Yeah. I mean, I would say this is a huge thing. I’ve been on good boards and bad boards. I’ve been on boards that are super functional. For example, the Etsy board where I was the chairman, that was an amazing board. It was a hands-on board. It was a strategic board. It was a collaborative board, and it was a very active board. We were constantly in conversation. We all knew what our position was. We all played our position really well. And obviously, you can see it came from three kids in a cold water flat in Brooklyn to IPO and $25 billion market cap, all that. I think that was an incredible board and a lot of it was that all of the members of it were very engaged. Very deliberately so.

Chris: So as a board member, are there times where you’re like, “Hey, come on, you need to do this thing, ” or “Hey, why don’t you do that?”, where you’re talking to each other about where certain support could come from?

Caterina: Yeah. Yeah. Oh, for sure. We need this financing. We’re doing this recruiting. We need a CFO, we’re going to go public. All of the stuff like that. When I was chairman, I had never taken a company public like that before, but all of my other fellow board members had, so I leaned on them like, “Help us figure out who the banker is. How are we going to do this? What kind of CFO do we need?”

Supporting your passions and leaving the comfort zone

Chris: Yeah, there’s a lot of maybe giving back you’re doing with that. Obviously, there are often incentives for being a board member, but just kind of giving back via Creative Commons and some of the other stuff you’re doing to give back, what motivates you to do that? Tell everybody what those ideas are and what you’re doing that you’re really passionate about.

Caterina: I’m on the board of, at this moment, I think I’m on the board of three nonprofits. Is that right? I’m no longer on the board of Creative Commons, but I’m on the board of Sundance Institute, which runs a festival, but a lot of other programs for independent film. And I’m on the board of City Arts & Lectures in San Francisco, which is a lecture series that brings together thinkers and writers to do on-stage interviews. That was where I interviewed Michio Kaku, the physicist. And also—

Chris: That was an onstage, live interview?

Caterina: It was an onstage, live interview.

Chris: That makes so much more sense why you had to be super prepared.

Caterina: Yes, yes. And it was being recorded for the radio.

Chris: Unedited, unabridged.

Caterina: Yeah. I mean, winging it was not an option. Then the third one is McSweeney’s, which is a book publisher and they publish a quarterly of short stories and kind of literary pursuits. So all of the things I love, reading and literature and poetry and writing and thinking and big ideas and all of that stuff are contained in all of those things I do. And it’s important for me to be in a position where I can give back to be able to do that. So I just kind of naturally gravitated toward that. I didn’t have a lot of bandwidth many years ago when they started to recruit me for the Sundance board, but eventually I caved and I love that board. It’s lots of fun.

Chris: It’s got to be a good one.

Caterina: The festival is super fun. It’s in Utah every year.

Chris: Yeah.

Caterina: So much fun. Love it. Especially for a skier. I was formerly a skier and rock climber.

Chris: Any favorite mountain?

Caterina: Well, at this point it’s got to be Park City because I have to go there all the time.

Chris: You’ve got to go there all the time.

Caterina: Yeah.

Chris: No plug there. Yeah, because I live in Colorado, so I love Copper Mountain and Vail and all that good stuff.

Caterina: Of course, yeah.

Chris: A lot of good ones.

Caterina: Amazing. I was an East Coast skier too, so I skied on ice.

Chris: On ice, yes.

Caterina: So I was like, I got out here and I’m like, “What is this fluff? I can’t move. This is slowing me down. Give me some ice.”

Weighing the pros and cons of the latest technologies

Chris: Give me some ice. Well, there are a couple things I’m really interested to know in terms of where things are headed.I want to know both sides of the coin. What is the thing you’re cautious, wary, concerned about? And what is something that you’re like, “I am so enthusiastic and excited about this next thing”?

Caterina: Well, one thing that fits into that category very obviously is fear, uncertainty and doubt, AI. Enthusiasm and like, “Oh my God, this is amazing,” AI. So it’s both, right? Because I do think there’s this misapprehension of what AI can and can’t do, or can or should do. I mean, I am a bit of a maverick in the tech industry. I mean, who else goes out there and says, “Should this exist? I have a podcast called “Should This Exist?”

Chris: Yeah. That’s fantastic.

Caterina: I come from a very different mindset, because in the tech world, it doesn’t work that way. It can exist and therefore, it should exist, is kind of the default belief system. We can do this—

Chris: Can we make it work?

Caterina: We can make it work. It’s amazing. It’s cool. It’s a tech-first mindset. Whereas I always came from a mindset of “we’re solving a problem and then you have the technology to solve it”, which is a very different place, to be honest. I do think there’s so much of that going on in the tech world. You figure out how to do something and it’s really cool and then you hunt around for a problem to use it for, which I think is backwards. So I do think AI is being used for all kinds of things it shouldn’t be used for because all of this chatGPT stuff is, I think it’s valid that everybody’s concerned about it. And I’m very happy that everybody’s concerned about it because they should be. And everybody else was kind of, “Sure, kind of harvest and use all of my data. Sure, that’s fine,” before, but now they have this very sensible, cautious approach to technology and what it could do.

So I think that’s actually a good thing that people are being more cautious around the technologies they’re seeing out there. But the problem with AI is when you assume it has anything to do with being human. Because when you have a conversation, we’re sitting here right now, we have histories, we have responsibilities, we have obligations to others. We’re like human beings. And we assume we have intention and that we also live with the consequences of the things we do and the things we say. AI has none of those things. It’s not a person, it’s just an accumulation of a bunch of inputs and data. It’s coming from the internet, which excludes a lot of humanity and a lot of perspectives and a lot of people.

Chris: Selective humanity.

Caterina: Selective humanity, technologists, as everybody knows, are really peculiar and weird people. And those are the people who are actually creating the system. So I think it’s not a very healthy system. That said, there are incredible uses for AI that are tremendous, that can save people a lot of time and trouble and work. And if you use chatGPT for the right things, it can be just like having an extra arm. It’s amazing. So I think finding and realizing and understanding what the correct use cases are is really important. For my new podcast, I have an upcoming podcast, which is called “Ingenious”. I just interview a bunch of teenagers, like 14-year olds about chatGPT and whether or not they’re using it for school—

Chris: Oh gosh, I’ve got to listen to this one.

Caterina: And here’s the thing I thought was great. So we were interviewing them. We asked, “Do you use chatGPT? What do you use it for?” And they’re all like, “Yep, yep. We use it, we use it. We use it for writing papers, we use all this kind of stuff.” Then one of the kids said, actually two of the kids said, “You know what? I try not to use it that much. I really worry it’ll make it so that I can no longer think. I really want to be sure I’m learning something. I really want to be able to think on my own without the help of a machine. So it’s important for me to just use it for the things it’s good at, and then use my own brain for everything else.”

Chris: Dude. Wow.

Caterina: Kids, yes.

Chris: Look at that.

Caterina: Kids these days. Oh my God, they’re so smart.

Chris: Yeah, they’re just dropping wisdom like, “Well, I was raised with values and...”

Caterina: Come on. Even us, old fogeys, there we are. Like we could always plagiarize. You could always plagiarize. Plagiarizing was always an opportunity. You can always do that.

Chris: Yeah. Now you can just do it in two seconds.

Caterina: Yeah. It’s faster.

Chris: Yeah. Well, what’s next for you?

Caterina: Just fund three, more investing, entrepreneurs, pretty soon I’m going to move from A2 French, I’m now borderline between B2 and C1 if you pay attention to those rankings. So pretty soon I’m just going to be, I don’t know, teaching PhDs in French. We’ll see.

Rapid-fire questions

Chris: Well, I have a few more questions for you.

Caterina: Sure.

Chris: But they’re just our rapid-fire questions.

Caterina: Okay.

Chris: Yeah?

Caterina: Shoot.

Chris: Are you ready?

Caterina: Yep.

Chris: All right. What is the most impactful novel you’ve read this year?

Caterina: Novel?

Chris: Novel. We’re hearkening back to English Literature.

Caterina: I know. I’ve read so many novels. Can I open up my Goodreads?

Chris: Sure.

Caterina: I can remember?

Chris: Absolutely.

Caterina: Because the fact is that kind of calling them up is sometimes hard. So here, I’m going to grab my list of books I’ve read this year. You mean in the past calendar year?

Chris: Let’s just say past 12 months.

Caterina: All right, hang on a second. I’m going to open this up, my list. I’m hoping to interview Gabrielle Zevin, who wrote “Tomorrow, and Tomorrow, and Tomorrow”, which is about a bunch of game designers. So I’m reading that. I haven’t finished it yet, so I can’t really—

Chris: You can’t put that on the list yet.

Caterina: I can’t put it on the list. The other thing too is that I homeschool one of my kids, so I teach short stories actually, which has been amazing. Homeschooling, I don’t think people realize, you think it’s for the kids, but it’s 10 times more fun for the adults. I swear to God. If you’re doing it properly, I mean, it’s so much fun. Because I look at this now and I see a bunch of stuff I’ve read for teaching the English class, for teaching like language arts. So there you go. It’s really great. “Trust” by Hernan Diaz. That’s a business book, actually, but fiction, it’s so interesting.

Chris: That’s cool.

Caterina: That’s really good. “Liberation Day: Stories”, by George Saunders. Best thing he’s ever written. Incredible. He’s a Pulitzer Prize winner or National Book Award winner. I don’t remember. He won it for “Lincoln in the Bardo”. Fantastic. Amazing writer. Amazing. I have a book of poetry, “Popular Longing" by Natalie Shapero, which I would love for everybody to read. Really good book. “The Creative Act: A Way of Being” by Rick Rubin.

Chris: Oh gosh.

Caterina: Founder of Def Jam.

Chris: I have been wanting to read that.

Caterina: Read that. Read that. Really excellent. Really excellent.

Chris: I love that he’s been on so many podcasts recently. It’s just been awesome. He’s kind of having a moment.

Caterina: He’s fantastic. I mean, I just read so much. I can’t even go through all of them because here’s a Norwegian writer, “A House in Norway" by Vigdis Hjorth. Amazing.

Chris: Well, when we were putting these questions together, we were like, “We’re going to see, she can get it to one.” I didn’t know whether you were going to rattle them off or if you were going to do something like this.

Caterina: It’s impossible. I mean, I’m just looking at this list and I don’t know, you’ve just got to follow me on Goodreads. One of these books, “The Rabbit Hutch” by Tess Gunty is one I loved. Really great. Sutton, Indiana. It’s kind of a very Midwestern book. It’s great. Yuri Herrera, “Signs Preceding the End of the World”. I have read that book four times. I read it again. I could go on.

Chris: I love it. All right, question two. Are you ready? If you could have any superpower to help in your business, what would it be?

Caterina: I think the ability to see the future.

Chris: Okay.

Caterina: I think it’s pretty clear. What happens next, are guesses correct? Because a lot of what we’re doing in our work is trying to predict the future and trying to feel the vibrations on the ground of the stampede that’s coming and going in a certain direction. Where is it going? So that would be it.

Chris: I like that superpower. Well, what’s one lesson you wish you had learned earlier in life?

Caterina: How important kindness is, and you don’t even realize that when you’re the boss, you can just trample over everybody’s feelings without even realizing it. You can be inconsiderate and say something like, “Let’s do this by Friday.” And you don’t even realize everybody’s going to be working nights and weekends to get that done for you, and you don’t even realize it. Being the boss is a lot more responsibility than it seems. It seems like you can just be the empress of your whole domain, but it doesn’t really work that way. I think I learned that the hard way over the years of being a boss. It’s really that you’re there to support other people. So that’s a big one.

Chris: That’s good. What’s the best piece of advice you’ve ever received about entrepreneurship?

Caterina: About entrepreneurship?

Chris: Yeah. What’s the best advice someone’s ever given you?

Caterina: So this is going to be funny coming from a VC and an investor, but James Currier, who is one of our investors in Flickr, said, “No one can ruin your company faster than your investors.” I can’t even tell you how many times I have repeated that to founders where they’re taking money from people they don’t like or trust because they got a good valuation. You can split up with your co-founder, you can change your product, you can fire and rehire your whole team, but you can never get rid of your investor and your investor is there forever. So if you don’t like or trust that person, it’s done. I always said, “When you’re looking for capital, you look for the partner first, the person you’re going to be actually working with day in, day out. Then you look at the terms you’re being presented and then you look at the valuation, in that order.”

Chris: Love that. What is currently your favorite app you use and why?

Caterina: I know I’m kind of late to the game on this, it’s a little bit embarrassing because we’re also investors, but I have an Oura Ring and I now am addicted to the Oura Ring. I mean, seriously, how long has this been now?

Chris: That it’s been out?

Caterina: Yeah.

Chris: I don’t know. It’s been a couple—

Caterina: Seven years?

Chris: Yeah, it’s been a few years.

Caterina: Long, long time.

Chris: They’re getting traction though.

Caterina: Huge. And I just love it. I’m like, “How did I sleep? Can I sleep better? I should take it easy today.”

Chris: Yeah. So you’ve been—

Caterina: I’m all on it.

Chris: We’ve tried to get their head of product or their CEO on the show. Yeah. It just hasn’t worked out timing wise, but it is amazing to see what they’ve done.

Caterina: It’s amazing, I mean, it’s fantastic and it tells you things you kind of suspected but didn’t know and you start having the Oura Ring and do you have that glass of wine before bed? No. Never again.

Chris: You’re like, “No, it’s going to mess with me.”

Caterina: You just don’t because it really affects you and so it makes you live good through technology.

Chris: Yes. All right. So this is an interesting one, and you can figure out how you want to answer it, but what’s the biggest multiple you’ve yielded in an exit? It could be something you’ve invested in or it could be something you started.

Caterina: Well, I mean, one of the most incredible outcomes I’ve ever had was I was a limited partner (LP) in Chris Sacca’s first fund, which was an insane outcome, seconded only by the outcomes for Founder Collective’s first fund where I was a partner and one of the founding team members. Those were early-stage startups. The vintage was incredible, 2009. When you get to be my age and you’ve been investing for this long, you see vintages come and go and some are better than others. That was just—

Chris: What was one of the biggest names we’d know in that first one?

Caterina: Out of this world, Twitter and Uber.

Chris: Okay. Enough said. All right, well, what entrepreneur inspires you the most or has inspired you the most?

Caterina: That’s so funny because I look at... So for example, I’m half Filipino and all of the women on my Filipino side of the family are just bosses. I mean, watch out. They’re forces of nature. They’re unstoppable, they’re fearless, they don’t give a shit. They are right in there. They’re unafraid, all of them.

Chris: And those are the ones who are keeping it going.

Caterina: I don’t know, just go catch a flight to Manila and meet some ladies.

Chris: Let’s just say that’s a resourceful area.

Caterina: For sure.

Chris: For sure. Well, Caterina, it was such a privilege to have you here. Thank you so much for coming and being on live with us for this conversation. It’s just been amazing to get to know you.

Caterina: Likewise. Thank you for having me.

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