Caterina Fake on Her New Podcast, Should This Exist? With Kat Manalac

by Y Combinator2/21/2019

Caterina Fake hosts the podcast Should This Exist? which is about how technology is impacting our humanity. It launches today on iTunes. She also cofounded Flickr, Hunch, and Findery and is an investor at Yes VC.

Kat Manalac is a partner at YC.

You can find Caterina on Twitter at @Caterina and Kat at @KatManalac.


00:00 – Caterina’s new podcast, Should This Exist?

2:00 – Is there a process for considering if something should exist?

3:30 – Who should be part of these conversations?

4:45 – Wait But Why and the Human Colossus

6:50 – Episode 1 of Should This Exist?

9:45 – Having conversations before things exist

11:10 – How might employees think about their role in whether or not something should exist?

14:00 – Caterina reflecting on her creations and if they should exist

18:30 – Considering whether things should exist as investors

23:00 – Cofounder charter – What you will and won’t do

25:30 – Questioning the VC model

26:50 – Working on Wall St, feeling herself change, and quitting

30:50 – Caterina as a student

33:30 – Peculiarity and entrepreneurship

34:50 – “Don’t fight to win prizes that aren’t worth winning”

38:00 – What was once fringe is now mainstream

40:20 – Kat looking up to Lea Salonga

42:10 – Evgeny asks – How did she get her first 100 paying users?

48:55 – How does she advise founders to find investors?

54:15 – What questions should founders ask themselves while making something?


Google Play


Craig Cannon [00:00] – Hey, how’s it goin’? This is Craig Cannon, and you’re listening to Y Combinator’s podcast. Today’s episode is with Caterina Fake and Kat Manalac. Caterina hosts the podcast Should This Exist?, which is a show about how technology is impacting our humanity. It launches today on iTunes, and I’ve linked it up in the description. She also cofounded Flickr, Hunch, and Findery, and is an investor at Yes VC. Kat, who you’ve heard on the podcast before is a partner at YC. You can find Caterina on Twitter @Caterina, and Kat @KatManalac. All right, here we go. Caterina, you are starting a podcast. What’s it called?

Caterina Fake [00:35] – Indeed, I am. It is called Should This Exist? It’s been in development for several months now, and we’ve been working on it. It will be 10 episodes starting on the 21st, which I think is when this will go live. Basically, it’s about so much of what we do as entrepreneurs and as Y Combinator knows better than pretty much anybody is basically making the business case for your product, service, startup. We found in recent years especially that the conversation has turned to not can this exist, or how can we enable this to exist, but should this exist, right? A lot of the things that we’ve seen kind of come out in the world in the past several decades, sometimes they may not have been not necessarily what the founders intended, right? It may not have been what society wanted or needed, or even individuals wanted or needed. If there were a slight course correction, or if the founders had just been kind of asking themselves that question, should this exist, it’s a very important question to ask. Just flat out.

Caterina Fake [01:54] – Should this exist? Should this feature exist? Should we plan this company a little bit differently to address underrepresented groups? This has potential for kind of increasing bias, or inequality, or a thousand things that we can look at that are kind of these outcomes of our paths. As we all know, when you’re doing a startup, you’ve already been in existence for five years, it’s much more difficult to change your course than it is at the very outset. Those are the questions that we’re hoping to introduce into the conversation should this exist?

Kat Mañalac [02:30] – Is there a process that you go through when you’re trying to take apart an idea and figure out whether or not it should exist?

Caterina Fake [02:38] – Well, most of it comes out in conversation. A lot of it comes out in the conversational process that you engage in, not only with your team, right, as a founder, and as a creator, inventor. Actually, a lot of the people that we have on the show are inventors and scientists.

Craig Cannon [03:01] – People who are kind of just taking maybe some research or some new technology, and bringing it out into the world and productizing it. And a lot of the time, there’s a lot of questions out there. There’s a ton of, for example, groups that are kind of asking ourselves, what are AI effects? How do we manage the potential very great downsides of say CRISPR? There’s a lot going on right now, crypto. It’s like a very, we’re kind of going into realms in which we just don’t have a good ethical framework to discuss them even.

Caterina Fake [03:46] – Just making the kind of question the part of the conversation very important.

Kat Mañalac [03:52] – I think about this a lot, because I read thousands of YC applications. And some of them are for really incredible technology that I’m like, “Wow, this could have a huge impact.” Who should be part of that conversation when you’re trying to decide whether something should exist? Is it founders, investors? Or like how? How do you see that convo coming together?

Caterina Fake [04:10] – I honestly think that it’s a matrix, right? There’s a lot of people that should be involved in that conversation. I do think that one of the benefits of this show, and one of the things that we’re hoping to do with this show is to bring people in that are not necessarily normally part of the conversation, right? You want to bring in sociologists. You want to bring in historians. You want to bring in psychologists, people who actually study a lot of the different processes. And not all of us, computer scientists, user experience designers. Everybody starts off with the best of intentions. Nobody thinks that they’re going to do something destructive when they start off. As you kind of read in the poetry of like Baudelaire, “The descent to hell is by small steps.”

Caterina Fake [04:57] – You just kind of see that happening over and over again. You want to prevent the kind of the Theranos outcome. You want to prevent all of these things that you kind of get there.

Craig Cannon [05:11] – Have you ever read the blog, Wait But Why? It’s Tim Urban.

Caterina Fake [05:15] – Yes, I have. Yes.

Craig Cannon [05:16] – Tim talks about this idea in the context of what he calls the Human Colossus. Basically, he says we have this divine destiny, and that humans will just build. But it seems like you probably disagree. The market doesn’t necessarily push a product to a certain place.

Caterina Fake [05:35] – It’s one of the great things about humankind. Where we’re kind of homo faber, right? The maker, right? It’s like we are the makers. And we honestly just can’t help ourselves.

Craig Cannon [05:51] – Exactly.

Caterina Fake [05:52] – I honestly think it’s one of the best things about us is that we’re just endlessly curious. We like to develop new tools. We are kind of full of possibility and vision, and we see something that can be changed, and we want to change it. Right? I think it’s one of the best parts of our nature. But when we do that without a sense of some of the possible outcomes, or even being aware of them, and nobody knows. I mean, that’s why they’re called unintended consequences, right? Because they’re not intended. Sometimes if you sit down and you really look at it, you can see them. You can see, like if you had just kind of like taken the time, made this part of your conversation that you could put things on a completely different trajectory if you stop to think.

Caterina Fake [06:39] – And you know, it’s actually amazing how hard that is to do. Without exception, the entrepreneurs that we’ve interviewed so far for the show have been, they’ve all said, “We are so grateful for the opportunity to ask these questions and to have these conversations, because in our daily work, we never have. We aren’t asked these questions– By our investors. We aren’t asked these questions.” It puts them on much firmer ground themselves. Sometimes even exposes or kind of shows them possibilities for their products that they hadn’t previously seen. That’s super exciting when that happens.

Craig Cannon [07:25] – Well, so maybe we should be more concrete. What’s the first episode about?

Caterina Fake [07:29] – The first episode is about, it’s coming out today. If today is February 21st. It’s about a neuropriming headset that makes you learn faster.

Craig Cannon [07:42] – It’s like The Matrix.

Caterina Fake [07:45] – It’s actually was invented by Daniel Chao, who is a neuroscientist. He had actually done devices that were implanted in your brain that required literally–

Kat Mañalac [07:56] – Oh, wow.

Caterina Fake [07:57] – Opening up your head. He’s the real deal. He realized that this was an extremely frightening procedure for obvious reasons. His prior product had been called NeuroPace, and it was addressing epileptics, epileptic, kind of the medical treatment of epileptics using the electricity in your brain, right? Which makes sense.

Caterina Fake [08:23] – But had been, it was very difficult to get people over that hump of putting literally, like cutting your skull open– And implanting a device in your brain. And so he decided to go with a new product that you can still affect the brain, right, but you don’t have to be as invasive. Super interesting. A lot of ethical implications. It’s specifically designed around sports. And if it works, so much learning could happen. It’s almost science fiction. It’s like almost science fiction. Like there’s this movie from the ’70s called Fantastic Planet. It’s a French movie. And literally, the people in it in the science fiction movie put on a headset.

Caterina Fake [09:11] – And boom, learn everything, right?

Craig Cannon [09:14] – Yeah, I know judo.

Caterina Fake [09:15] – Right? And so it’s kind of sci-fi– In that way, right? I was always a big science fiction fan. Part of the reason that I love, frankly, these conversations is because they’re all about that kind of possibility. What if, what if? And you know, whatever, science fiction also has a very strong utopian–

Craig Cannon [09:37] – Of course.

Caterina Fake [09:38] – And dystopian–

Kat Mañalac [09:38] – Yes.

Caterina Fake [09:41] – Kind of interest. It focuses on those two potential outcomes frequently.

Kat Mañalac [09:47] – That’s one of the things that I’ve learned recently that has been so interesting is that big companies are starting to hire science fiction writers–

Caterina Fake [09:54] – Oh, really?

Kat Mañalac [09:55] – To map out these possibilities.

Caterina Fake [09:57] – Exactly. Because that is what they have been doing. That’s kind of what their job is–

Kat Mañalac [10:02] – Right.

Caterina Fake [10:03] – As science fiction writers. They’re just kind of future scenario planners.

Kat Mañalac [10:06] – Right, exactly.

Caterina Fake [10:06] – Right? Yeah, no, it’s amazing.

Craig Cannon [10:07] – This is kind of reframing the show to me. I previously thought it was more about criticizing things that currently exist. Is that happening? Or is it more about future ideas, and like–

Caterina Fake [10:19] – No, no. It’s more about kind of taking something that–

Craig Cannon [10:23] – That’s leading edge kind of.

Caterina Fake [10:23] – Right, that’s actually leading edge. And is something that is coming soon.

Craig Cannon [10:28] – Got you.

Caterina Fake [10:28] – And is even in market. Sometimes they’re in market. Sometimes they’re still in the kind of early development stage. But having those conversations at the very early side of those.

Craig Cannon [10:40] – Got you.

Caterina Fake [10:41] – Because there’s a lot of criticism online of things that already exist.

Craig Cannon [10:44] – Of course.

Caterina Fake [10:45] – If you read your op-ed of kind of your daily paper, you will find a lot of that. But what we’re trying to do is really kind of start it where we are. With new products. In some ways, it’s kind of the most fun.

Craig Cannon [11:02] – It’s also way more optimistic.

Caterina Fake [11:04] – And it’s more optimistic.

Craig Cannon [11:04] – Which is for me.. The dystopian stuff can be kind of–

Caterina Fake [11:07] – You could just sit around and criticize the existing technology all day long. It’s actually very gratifying to do that. In some ways. But I’m not sure what–

Craig Cannon [11:16] – In like a mean, putting down celebrities kind of way.

Caterina Fake [11:19] – I think that the goal of this show is actually much more about possibility than shutting stuff down.

Craig Cannon [11:30] – This is a little bit of a side note, but I did have a question about current existing technologies. If you say were an employee at a company where you’re like, “I don’t know if this should exist?” How do you think about that idea now? Because it’s no longer like if you’re working at a hardware store 50 years ago, and you’re like, “I don’t know, I just sell like screws, and hammers, and nails, and whatever.” Kind of like doing no harm.

Caterina Fake [11:55] – User-neutral.

Craig Cannon [11:57] – Yeah, it’s neutral.

Caterina Fake [11:58] – They’re not harming anybody. you can harm somebody with a hammer

Craig Cannon [12:00] – Right. Maybe you’re like, “Oh, I sold screws to a serial killer” sure. But, but now you’re like, okay, I think maybe five years ago, people might say like, “I don’t know, I’m just an employee at this company, and I’m just whatever.” This is a fine salary.

Craig Cannon [12:20] – Not so easy to say today.

Caterina Fake [12:18] – Right. One of the great things about millennials, and what are we calling the people that come after the millennials?

Kat Mañalac [12:30] – Gen Z.

Caterina Fake [12:32] – Gen Z? And then there’s the one that like, there’s like, after it. Kids today…

Craig Cannon [12:38] – The youth.

Caterina Fake [12:40] – Youth, whatever you call them these days. Are super engaged, and want to know that the things that they’re working on have merit, are putting things on a good trajectory, have positive impact, and not negative impact. You see this happening over and over again. You saw recently the Google walkout. You see organizations rising up to help people inside of organizations communicate with each other and figure out how to communicate this to senior management, et cetera. It’s a huge movement. And I think that people have started to realize as employees of large companies that they also have the power to say no.

Caterina Fake [13:25] – No, it should not exist this way. Maybe it should exist this way. And actually be part of that influence, and conversation, and– And kind of actually set the trajectory of their work.

Caterina Fake [13:40] – Because it’s their work. It’s really it’s the work that you to do every day, and you have to feel good about that. We all recognize that where a lot of the time, those of us who are so lucky to earn paychecks working in technology, right, which is a privilege, right? And most people do not have this privilege. We should consider ourselves extremely lucky. Are able to with our work, and you can kind of see, change the world, right? And kind of this has always been the promise of Silicon Valley. We’re here, we’re going to change the world, right? There’s tons of that. Are you trying to change the world for the better? Yes, you’re changing the world, right? Everybody’s changing the world with their work every day.

Caterina Fake [14:20] – A little bit by bit. Right? Are you changing that world for the better or not? You want to be always making sure that you bring your moral compass to work with you.

Craig Cannon [14:34] – Absolutely, and you have a choice. Because I know many people at companies who feel like they got lucky.

Caterina Fake [14:40] – Sure.

Craig Cannon [14:40] – And they just ended up there. And they’re like, “Oh, I don’t know. I might be part of this machine, but I don’t know if I can be part of another machine anymore.” Like this might’ve been one hit.

Caterina Fake [14:48] – Right.

Craig Cannon [14:49] – And so they get locked in.

Caterina Fake [14:48] – Right.

Craig Cannon [14:50] – But I think as people start to think about stuff, they do end up moving on. But I was curious about you as a founder, do you ever look back? And maybe even on projects where you’re like, “I don’t know. I don’t know if I should’ve made that.”

Caterina Fake [15:03] – Like if that was a decision that should’ve been made? Well, sometimes you can’t see the consequences of it. For example, if you go back to my Flickr Photostream. To around 2004, you’ll see the design, I posted it up there, I think 2008 or something like that, of the first activity feed. I never call it a feed. I called it recent activity. Because a feed always reminded me of like animals at a trough.

Craig Cannon [15:26] – Which might be more accurate.

Caterina Fake [15:28] – Which may be more accurate, right? Subsequently, right? This was a significant thing. Right? It was not invented by me. It was just really invented. It was kind of reverse chron that we had seen in blogs. The difference was it included activity from other people in your social network. It was the first time that this had actually kind of appeared. You would see people liking your photo.

Caterina Fake [16:01] – You would see when your friends had posted a photo, and all of that kind of thing. And you could just basically see activity as it was happening on the system. And it’s interesting because this was then adopted by Facebook subsequently. But the changes that were made there were very significant. And we could see it all the way along the way. We could see that, oh, suddenly, they’re reordering things based on people’s attention. Not on chronology, right? This is super significant. We saw that, and we’re like, “Whoa, that is not good, right,” because suddenly, if you have somebody, it’s kind of the same thing on kind of television. What gets your attention is not necessarily the thing that you should be paying attention to. It’s a security hack of your biology is kind of how I think about it. Because you’re just kind of as an human animal, you see naked people, you are not going to not look at that.

Caterina Fake [17:09] – You see a car accident, you’re not going to not look at that.

Craig Cannon [17:11] – It goes back to the early days of newspapers. If it bleeds, it leads.

Caterina Fake [17:14] – If it bleeds, it leads.

Craig Cannon [17:14] – That’s what they used to say.

Caterina Fake [17:15] – Right? And so once you start organizing things not based on, simply, I am interested in following this person, right? I’m interested in what they have to say, exciting or boring, right? Or I trust this news source, et cetera. And then kind of making it so that not only is it the most attention-getting things are promoted, but you can buy your way there.

Caterina Fake [17:46] – A recent activity, reverse chron list, is actually just, I don’t think there’s that much wrong with it. Until you start adapting it in these somewhat nefarious ways.

Craig Cannon [17:59] – Right.

Caterina Fake [17:59] – You see kind of some of the inventions that you–

Craig Cannon [18:02] – Well, but then you go back. You could look at, I forget what year it was, but then there was the rise of things like Upworthy. So they gamed it in a different way.

Caterina Fake [18:12] – Sure.

Craig Cannon [18:12] – So that was like the early days.

Caterina Fake [18:12] – Sure.

Craig Cannon [18:13] – “Oh, we can sensationalize positive things and get in the feed.” Because as soon as you switched to paid promotion of your Facebook page–

Caterina Fake [18:23] – Right.

Craig Cannon [18:23] – It changed the game.

Caterina Fake [18:25] – Sure.

Craig Cannon [18:25] – You didn’t get any activity in the feed unless you bought your way to the feed.

Caterina Fake [18:29] – I know. And it was kind of a tragic thing to see a network that was yours. Right? Like these are your people. Like this is your cousin, and your sister, and your coworker, and your friend.

Craig Cannon [18:40] – And you don’t even see it.

Caterina Fake [18:41] – And then suddenly like– They’re gone. And so I mean, yes, you can sensationalize– Worthy things as well. But I think that the problem is in the verb sensationalize, right? Attentionify.

Caterina Fake [19:02] – It’s an issue.

Craig Cannon [19:04] – But now both of you guys are doing this as investors. Kat, you sit in interviews at YC. How do you think about, “Oh, I don’t know… Maybe this shouldn’t exist?”

Caterina Fake [19:16] – Do you put your money behind it? Because like honestly, it’s super interesting. I was talking to a guy recently. And he was introduced to JUUL really early.

Caterina Fake [19:29] – Which is the cigarettes, right? And the way he was pitched this was it’s a great product. It will reduce smoking, right? Fewer people will smoke as a result of using JUUL. And he was kind of like, “Okay, well, that’s a interesting claim. But then why would you start a smoking company to have there be less smoking,” if you know what I’m saying. And so and then he kind of looked into it, and he was like–

Craig Cannon [19:55] – No.

Caterina Fake [19:56] – In no way are they actually explaining the addictive properties of nicotine. It’s now, what? There’s five million new smokers because of this single product, this single product. They recently got investment from Philip Morris. He could have at the very early stages of JUUL, because he happened to meet them really early. Have invested $250,000 in this company, which would now be worth $25 million. That 250,000. He said, and I thought that this was super interesting, “I never had put a price on my ethics and integrity before. But I now know–“

Craig Cannon [20:39] – It’s 25 million.

Kat Mañalac [20:40] – Exactly, it’s 25 million, at least.

Caterina Fake [20:43] – Because that’s just where it is now. Yes, you can totally get rich by burning down the rainforest, and kind of creating sexist media, and all kinds of things that you can invest in, right? Do you invest in them is the question.

Caterina Fake [21:02] – At Yes VC, I’m an investor, and my firm is called Yes VC. We have generally certain categories that we won’t invest in.

Craig Cannon [21:14] – Which is true for a lot of funds, right? The LPs have rules–

Caterina Fake [21:15] – It’s true of a lot of funds, right?

Craig Cannon [21:16] – Like you can’t invest in guns.

Caterina Fake [21:18] – Right, but we don’t invest in gaming, right? We don’t invest in a lot of games, and the reason that we don’t is because it’s like a lot of the time it’s like it has all the same mechanisms as addictive gambling and things like that. And a lot of times, it’s just like Las Vegas for children. And you realize that the same mechanisms that are the same security exploits, frankly, that social media has taken advantage of are, which that’s a whole nother conversation that we can have about my opinions of social media. We just don’t want to be in that kind of atmosphere if it has those kinds of properties. Right? Those compulsive, addictive properties. It’s just a category that I’m not against games, you know? I’m like a give me some Settlers of Catan any day.

Caterina Fake [22:11] – But I’m not in the business of creating these addictive-like behaviors. The gaming category is full of that.

Kat Mañalac [22:24] – That’s why I like the concept of this show that you’re doing a lot, because I think more of those conversations about should we fund this, should we be part of this? Oftentimes, since we’re so early, we’re the first check, we’re the first money in. That is pretty powerful. So it’s like–

Caterina Fake [22:42] – It’s so powerful. Because you’re basically putting the Y Combinator– Seal of approval on every company that you invest in. We, too, we’re like putting the Yes VC seal of approval–

Caterina Fake [22:56] – On every company that we endorse. It’s an endorsement.

Craig Cannon [23:00] – Of course. Tricky things have happened at YC, absolutely, where a company pivots, and you’re like, “Oh, boy. That was not the intended consequence of the 120 grand–“

Craig Cannon [23:10] – At the time.”

Caterina Fake [23:10] – Exactly. Right, and you can kind of disavow them. Try to go in and coach them and whatnot. Part of the Y Combinator conversation should be in the should this exist direction. It’s important. And I think it’s also important, another thing, too, is that we have a, we wrote this thing called the Cofounder Charter, which is a conversation that cofounders have, and I’m sure that Y Combinator has some version of this as well, where you kind of set out your expectations, your hopes and dreams for the company, and where you would want to go. But I think it’s really important, also, to put down in that document what you will and won’t do, like where are the limits? If you’re in AI, or you’re in CRISPR, or you’re in one of these kind of emerging categories, it’s like an ethical minefield. Where you will and won’t go.

Kat Mañalac [24:12] – Do you make all of the founders that you invest in fill out this charter?

Caterina Fake [24:16] – No, no, we don’t. It’s kind of offered. And we kind of have the conversation. We encourage that conversation, it’s not required. But I think that our founders tend to be of a certain kind. If you look at all of my prior companies, my prior investments, they do have a certain flavor. There’s a certain ethos that they have common. Flickr was an online community. They were kind of it was a very human community. Very creative. Very communicative. Other companies that I’ve been part of include Etsy, where I was like the fourth or fifth person there on the founding team, and then became the chairman up through its…

Caterina Fake [24:59] – And then, you know, other companies that I have funded like Kickstarter, they have a very I think human ethos.

Kat Mañalac [25:09] – Absolutely.

Caterina Fake [25:10] – And the kind of technology that I’ve always hoped to build. And part of the reason I’m doing this podcast is that I’ve always seen a big part of my job as me, Caterina Fake, is actually to humanize technology. Because it can dehumanize us, and it has a tendency to do that if it goes in certain directions. To constantly bring it back to the human, to the relational, to the interpersonal, to the communitarian, to the creativity, all of those things about us.

Craig Cannon [25:37] – There are also all these structures that you’re working within. Because I think people could say like, well, VC is inherently prone to being susceptible to all of these vices, right?

Caterina Fake [25:47] – Yes.

Craig Cannon [25:47] – ‘Cause you have the money. You’re like, here, I’m going to give you x amount of money for y percent.

Caterina Fake [25:52] – Sure.

Craig Cannon [25:52] – And it assumes a certain amount of hopefully infinite growth, right? And people will just beg, borrow, and steal to get that number.

Caterina Fake [26:00] – Right.

Craig Cannon [26:00] – So they can keep increasing the valuation.

Caterina Fake [26:01] – Right.

Craig Cannon [26:00] – So they can keep raising, so they can exit.

Caterina Fake [26:04] – Right, yeah.

Craig Cannon [26:05] – But you exist saying, and I think YC’s in a similar boat. That doesn’t necessarily have to be true.

Caterina Fake [26:11] – Right.

Craig Cannon [26:11] – But it’s painted that way often.

Caterina Fake [26:12] – There’s so many conversations that are going on right now about the VC model.

Craig Cannon [26:18] – Of course.

Caterina Fake [26:18] – That I think are great. Everybody questioning the unicorn blitzscaling, 99 must die for one to succeed model. Which I think that for decades has been taken as the single path to a successful Valley venture-funded company. Which is why you end up with the venture-backed sociopaths, and these, truly.

Craig Cannon [26:47] – Yeah, of course.

Caterina Fake [26:48] – It actually kind of puts you in the position where you have to become a worse person, right? You have to change your goals, and your desires, and who it is that you become. And I worked on Wall Street for six months. It’s as long as I could actually hack it.

Craig Cannon [27:07] – Was that when you were the door assistant? You mentioned this on another podcast I listened to. You were like writing a novel, or something.

Caterina Fake [27:15] – I was a receptionist.

Craig Cannon [27:16] – You were reception.

Caterina Fake [27:18] – This is a long story. I was a painter. Like literally a painter making like nothing, literally nothing. I was living on, like there’s this place in New York that it was called Gray’s Papaya, where famously you could get a 99-cent hot dog.

Craig Cannon [27:36] – Near my house, right? A 99-cent hot dog and a soda. This was like the lowest–

Caterina Fake [27:42] – Great deal. Lowest nutrition period of my life. I’m not sure how I survived it. I was like thin as a rail. But I was a painter, and I took all these temp jobs. I had a temp job at a investment bank. The managing director of this department came to me, and he said, “Ooh, kid.” I was only like in my 20s, super young, early 20s.

Caterina Fake [28:05] – And, “You’re really smart. You could be an analyst here.” And I’m like, “Well, I’m a painter, and it’s kind of not my desire.” And he’s like, “Yeah, but I’m going to pay you a six-figure salary.” And I’m like, six-figure salary? What? I’m like literally I’m living on like 99-cent hot dogs at this point. I’m like, “Okay, I think I can take you up on that.” I went out and I bought myself like, literally, I bought myself a suit, like a power suit.

Craig Cannon [28:30] – Wow.

Caterina Fake [28:30] – And like some shoes, right? Because I’m workin’ on Wall Street. I can’t look like a receptionist anymore. I’m like an analyst, I’m like the real deal. So I step in, and within six months, I found myself becoming a different person. This was the thing that I noted in myself. I was surrounded by, and it was all guys, right? It was like me and a bunch of guys, right? And I was as tough as any of them, right?

Caterina Fake [28:53] – I was just tough as any of them. They were so impressed by me. They started calling me brass balls. This is Wall Street, right? This is very Wolf of Wall Street kind of environment. Totally Wolf of Wall Street environment. I could be just as obnoxious as them, and that’s what they liked about me. I didn’t like that that was what they liked about me. They didn’t like my kinder, gentler, more thoughtful, poetic, painterly qualities. They liked the fact that I could just rise up or down, lowered myself down to their level.

Caterina Fake [29:28] – I could kind of meet them where they were, and just be like, I can give as good as I get here. Then I realized what was happening to me as I, so literally, that was like six months of that experience where I was just becoming the wolverine of Wall Street. I didn’t want to become that. What happened was I got off the subway on Fifth Avenue in New York where I was living, and was on my way to work, and I remember I had just become so angry all the time. And that I was walking down the street, and I was refusing to move aside for other people, right, because I was just like in this world of, I don’t know, I was some kind of elite, entitled person. It was awful. Truly, I was transforming into just the most horrific person. It was actually when I was standing there on the sidewalk unwilling to move aside for other people that I realized that I had to quit. I walked in, and I quit that day, because I was just like it’s not worth it. This is the end of you. Like you have become a monster.

Craig Cannon [30:37] – That’s very self-aware. A lot of people do 20 years before they figure that one.

Caterina Fake [30:40] – I was going to say, you realized that pretty quickly. And I was back to 99-cent hot dogs within 24. Actually, I was good at saving.

Caterina Fake [30:51] – So that’s not entirely true. But you know, right? And so that was kind of a big moment.

Craig Cannon [30:59] – I think it’s dangerous, right? You get part of a certain culture, and then you want to be good at the game. And we see this in the Valley, right?

Caterina Fake [31:06] – Yes, exactly.

Craig Cannon [31:06] – You’re like, this is the game I’m in.

Caterina Fake [31:08] – Right.

Craig Cannon [31:08] – And I’m going to mold myself to make it work.

Caterina Fake [31:09] – That was the game. And I’m good at the game. I can always figure out the game.

Craig Cannon [31:13] – Exactly.

Caterina Fake [31:14] – I can always figure out the game.

Craig Cannon [31:16] – Right.

Caterina Fake [31:16] – That’s one of my special sauce is that I would get in a system. For example, school.

Craig Cannon [31:24] – We should talk about this.

Caterina Fake [31:26] – Because I was a horrible student. I was a great student, and I was a horrible student. I liked to learn, but I didn’t like to be taught. And so I had this, you know. I would go to class, I would, for example, eighth grade geology. I was like, “Oh, this is great. I’ve been collecting rocks my whole life. I’m so into this.” I sat down and read the geology textbook.

Caterina Fake [31:49] – And I was like, “Oh, I love this subject. This is so great.” I showed up for class, the second class, and I realized that the teacher was just going to read out of the textbook, which I just read. And so I’m like, “This is horrible.” I’m not going to bother doing this, so I left. And they, I kept on getting marked absent. I was a truant. My parents had to come in and talk to the principal, and all these kind, they made me go back into class again. In order to get around this, I would read. I would check out of the library. I’d get interlibrary loan. I would get all of the books of the bibliography of each of the chapters in my geology textbook, and I would read them.

Caterina Fake [32:28] – And then I would sit in the front row, and the teacher was like, “Hey, blah blah blah, blah blah blah blah blah blah blah, plate tectonics this.” And I was like, “If you had read,” I would raise my hand, “If you had read the seminal paper in plate tectonics, you would realize that, blah blah blah.” And I was like the most obnoxious.

Craig Cannon [32:41] – That went over really well. I’m sure.

Caterina Fake [32:43] – It went over incredibly poorly. Which is kind of a design. Then I was excused from class. She kind of took me aside and said, “If you just show up for the exam, I will not report you absent anymore.” I did all of these weird workarounds, and then I kind of just would, and it wasn’t like I was off smoking dope behind the bushes. I was actually in the library–

Caterina Fake [33:04] – Reading. It wasn’t like I was a bad student. I was truly… Institutions and I have never gotten along well and I was always like that. I discovered that if you did really well on standardized tests, you were good. I was one of those students where I had straight Cs. Then occasionally, I would get A-pluses in a class where I had a really stellar teacher, and I just loved them, and I would do everything that I could. Then I had all these Cs, and I was always on the verge of getting kicked out. Yet, I was like a National Merit Scholar.

Caterina Fake [33:42] – I had this peculiar relationship to school and to education. There were a lot of people there who had so much better grades than I did. I did not get good grades in school.

Craig Cannon [33:56] – But it worked out okay for you, so now–

Caterina Fake [33:59] – Right.

Craig Cannon [33:59] – Do you feel that school is doing a disservice to many people, or are you just a small percentage of the world where you’re like, “I don’t know, I was never going to fit in here, and so I can succeed as an entrepreneur”

Caterina Fake [34:13] – I do think that that nature, right– That peculiarity is actually very common– Among entrepreneurs.

Craig Cannon [34:22] – I think so, too.

Caterina Fake [34:22] – Right? That tendency to look at existing frameworks in which you’re being forced to fit, and just say like, I don’t fit into this framework.

Kat Mañalac [34:33] – Right.

Caterina Fake [34:33] – This framework is not serving people. How can we upset it–

Craig Cannon [34:37] – Well, you can also–

Caterina Fake [34:40] – Or change it, or somehow adapt in a different way, and forge your own path. And you have to kind of be, like I said, have a lot of initiative, right? Like you can not go to class because you don’t want to do the work, of you can not go to class because you read all of the books in the bibliography on plate tectonics. You know I’m saying? Like you can…

Kat Mañalac [34:59] – Right.

Caterina Fake [35:01] – There’s different approaches, right? There’s different reasons to not go to class.

Craig Cannon [35:03] – Yeah, yeah, yeah.

Caterina Fake [35:04] – And if you’re not going to class for the right reasons, in the end, I think it will serve you. Right?

Craig Cannon [35:10] – It’s hard to have that confidence when you’re younger, right?

Caterina Fake [35:12] – Of course, oh, God.

Craig Cannon [35:12] – To step back, and be like, “Dude, this is all like, all these rules are made up.”

Caterina Fake [35:14] – I know, but I think that you have to look into yourself really deeply, and ask yourself, is this something that’s actually truly worthwhile, and to not fight to win prizes not worth winning.

Craig Cannon [35:30] – Right.

Caterina Fake [35:31] – So much of life is that.

Craig Cannon [35:34] – Yeah, and switch it up. I’m actually curious about both of you, who did you look up to when you were younger? Was there someone– Where you’re like, “Oh, man, I could be like them.”

Kat Mañalac [35:44] – Oh, that’s a good question. Do you have an answer? I’ll think about it.

Caterina Fake [35:51] – You know, it’s funny.

Craig Cannon [35:51] – Because when I think about it personally, and I’m like, school, I always did fine. It was no problem. It was not particularly difficult to get a B or an A-minus, whatever. But I was like, I don’t think I want to win this game. Yeah. And this is not where I fit in. And so I would just look around, and see like, “Oh, Spike Jonze is like, he’s making videos. He’s making skateboard videos.

Craig Cannon [36:13] – But he’s also starting a company.” And he’s doing all this creative work, that’s so awesome. So there is a model, right?

Craig Cannon [36:20] – And so I’m wondering if you guys–

Caterina Fake [36:21] – That’s right. And it’s interesting, too, because there, like you say, Spike Lee is kind of a great example of that.

Craig Cannon [36:29] – Spike Jonze.

Caterina Fake [36:30] – I’m sorry, Spike Jonze. It’s okay, Spike Lee, too.

Craig Cannon [36:32] – Spike Lee, also.

Caterina Fake [36:33] – Yeah, Spike Lee’s awesome.

Craig Cannon [36:33] – Yeah, yeah, yeah, why not?

Caterina Fake [36:33] – Actually, sorry. But Spike Jonze, and it’s so funny, because when I was living in New York around that same time, Spike Jonze was living down in Alleged Gallery. Down on the Lower East Side on Ludlow Street. I used to go hang out with those guys. They were publishing a magazine called Dirt.

Caterina Fake [36:55] – Do you remember this?

Craig Cannon [36:55] – I’m aware.

Caterina Fake [36:57] – Were you aware of this? And so we thought that this was the coolest thing ever, because it was. And I remember one of the things that I learned from that was how to deface, it’s illegal, how to deface a Canadian five to turn the, the old white dude–

Caterina Fake [37:17] – On the $5 Canadian bill– Into Leonard Nimoy’s– That’s great. Mr. Spock.

Caterina Fake [37:25] – Right, which was so, I remember that. It was actually from an early issue. And they had so many things like that that were quasi-illegal in Dirt. I don’t know if you ever saw an issue of this thing. Like how to drill a hole in a quarter so that you could use it repeatedly at the laundromat.

Craig Cannon [37:45] – I definitely know about that one. Sure.

Caterina Fake [37:48] – Just like a thousand things like this, and I’m like, “Can you publish things like?”

Craig Cannon [37:56] – And for me, it’s like, “Oh, there are these fringe examples of how it works.”

Caterina Fake [37:59] – Right. Right.

Craig Cannon [38:01] – And so–

Caterina Fake [38:02] – What’s interesting, though, and here’s the thing that’s kind of interesting. Is that what was, and this always happens, right, what was on the edge became the center.

Craig Cannon [38:11] – Totally.

Kat Mañalac [38:13] – 10 years ago. All the things we’re doing with startups and– Having individual founders being able to build enormous companies, they just didn’t happen.

Kat Mañalac [38:22] – And also, kind of culturally, rebellion was actually rebellion against a system, and now you’re kind of in, you’re on the inside.

Caterina Fake [38:32] – You know. You’re kind of being asked to disrupt. Right? And that’s a complete change, I think, in culture. Obviously, it’s been happening since, I don’t know, since Levi’s– Became like, like $600 jeans, right? You know I’m saying?

Caterina Fake [38:53] – It used to be just totally rebellious, actually rebellious to wear Levi’s.

Craig Cannon [39:00] – I mean, now.

Caterina Fake [39:00] – It’s kind of hard to say, right, but…

Craig Cannon [39:02] – I think I’ve heard the comparison multiple times that Facebook jobs are the same as a Goldman job 10 years ago. I think it’s kind of true.

Caterina Fake [39:10] – It’s kind of true. I mean, how much does an entry-level Facebook employee make?

Craig Cannon [39:14] – Six figures, I assume.

Caterina Fake [39:15] – Yeah, six figures. Right? I mean, you get a painter. You know.

Caterina Fake [39:22] – Sitting behind a reception desk at a investment bank. In the late ’90s.

Craig Cannon [39:31] – It’s so funny.

Caterina Fake [39:32] – It’s not that different.

Craig Cannon [39:34] – Do you have answers? We move on?

Caterina Fake [39:36] – Do we have answers?

Kat Mañalac [39:37] – Oh, about who we looked up to as kids. I don’t think, I’ll get back to you on that. I mean I know there’s so many.

Caterina Fake [39:44] – It’s super interesting, too. Because I think that there’s kind of cultural, Spike Jonze being a great example, there’s kind of cultural icons– That are not necessarily people you’re going to like, you didn’t become–

Craig Cannon [39:58] – No.

Caterina Fake [39:59] – A skateboarder filmmaker–

Craig Cannon [39:58] – No.

Caterina Fake [40:00] – Kind of media person, right? But you recognized in certain people a spirit– That you felt was something that you related to– And wanted to follow, or emulate, or you kind of just took his inspiration.

Craig Cannon [40:16] – As you are homeschooling, is that something that you try and set up for your kids?

Caterina Fake [40:24] – You kind of have to find those yourself.

Craig Cannon [40:25] – Yeah, okay.

Caterina Fake [40:25] – You know what I’m saying? You can’t just–

Craig Cannon [40:28] – But like set them up for the pursuit.

Caterina Fake [40:29] – It wasn’t like your parents were just kind of like–

Craig Cannon [40:30] – Here are your available options.

Caterina Fake [40:32] – Here, Mick Jagger.

Kat Mañalac [40:32] – You would’ve been like, no, thank you.

Caterina Fake [40:36] – No, I do think that you have to provide a rich environment in which those possibilities are there, present.

Kat Mañalac [40:46] – What I’m really thankful for today is that I was thinking through all the people that I looked up to, and only one woman comes to mind from being a kid, right? I really liked Lea Salonga, who was this, I’m Filipino. And who was this Filipino artist and performer.

Caterina Fake [41:03] – What’s her name?

Kat Mañalac [41:04] – Lea Salonga, she was the voice of Princess Jasmine.

Caterina Fake [41:07] – We should note for the record, I’m 1/2 Filipino.

Kat Mañalac [41:10] – Oh, you are. Oh, my gosh, how exciting.

Caterina Fake [41:14] – My mother is a Filipina.

Kat Mañalac [41:15] – Ah. Oh, my gosh.

Caterina Fake [41:16] – To say it the right way.

Kat Mañalac [41:17] – This is huge. Huge news.

Caterina Fake [41:19] – Yeah, no, no. No, it’s true, actually.

Craig Cannon [41:21] – Really?

Kat Mañalac [41:22] – I think that there’s, and I think what it was is just seeing a Filipino woman who was successful out in the world.

Caterina Fake [41:28] – Oh, yeah.

Kat Mañalac [41:29] – Put on a pedestal, and people really appreciated her work. I didn’t know any other Filipino women–

Caterina Fake [41:33] – Right.

Kat Mañalac [41:33] – That were featured anywhere. It’s so great now that there’s way more women in all industries that are highlighted and featured.

Caterina Fake [41:41] – Some of whom are 1/2.

Kat Mañalac [41:42] – Yeah, some of who are. And so that’s something that means a lot to me is seeing someone who looks like you. Or represents sort of the background that you came from them.

Caterina Fake [41:52] – Right.

Kat Mañalac [41:52] – Owning it.

Caterina Fake [41:53] – I think this is really important, honestly, if you’re an underrepresented group, right?

Kat Mañalac [41:57] – Yup.

Caterina Fake [41:58] – To see your kind of Latinx hero, to see your– Filipino hero. I think it’s important.

Craig Cannon [42:07] – Yeah, yeah, absolutely.

Kat Mañalac [42:08] – Now I have another Filipina here.

Caterina Fake [42:12] – Here we are.

Craig Cannon [42:13] – This is the most ever on one of our podcasts.

Kat Mañalac [42:13] – It’s exciting. The most Filipinos on–

Caterina Fake [42:14] – This is Filipino town. Where’s Diane Eisner? We need to–

Craig Cannon [42:18] – We can go get Jollibee together. It’ll be great.

Caterina Fake [42:21] – The Jollibee used to be a couple blocks away from here.

Kat Mañalac [42:23] – Yes.

Craig Cannon [42:24] – But is no longer.

Caterina Fake [42:26] – Do they have banana ketchup at the Jollibee?

Kat Mañalac [42:30] – I don’t think so.

Craig Cannon [42:31] – I could never get into the sweet pasta situation.

Caterina Fake [42:35] – It’s a thing, you have to grow up with it.

Craig Cannon [42:37] – It might be an acquired taste. We have some questions from Twitter– That I thought would be kind of fun to cover.

Caterina Fake [42:42] – Yeah. Okay, good.

Craig Cannon [42:46] – We have many questions. This could be kind of interesting. How did you get your first 100 users? But now you started three separate companies.

Caterina Fake [42:57] – Right.

Craig Cannon [42:57] – There’s Flickr, Hunch, Findery.

Caterina Fake [42:57] – Right.

Craig Cannon [43:01] – Did you apply the same strategies for all of them?

Caterina Fake [43:04] – They’re very different. It gets easier as you go along. I started on, maybe I didn’t kind of start from second base, but I started from first base, at least. I was already on base. Like in that I had a, I had a blog.

Caterina Fake [43:20] – That had a lot of followers. I had started this very early on. It was literally drawing from my existing community, and the people that I already knew who then were invited to and participated in. You have to, you start small. You start where you are with what you’ve got. I had the advantage of having been very gregarious online for several years before starting Flickr, which is where our initial– Our initial user base came from specifically.

Craig Cannon [43:57] – You were just blogging?

Caterina Fake [43:59] – I was blogging. I started a blog in 1998.

Craig Cannon [44:02] – Nice.

Kat Mañalac [44:03] – What platform did you use?

Caterina Fake [44:05] – It was on the first one was actually just written in HTML.

Kat Mañalac [44:14] – Oh.

Caterina Fake [44:14] – Actually.

Craig Cannon [44:16] – You just put up a page every time you had a new post.

Caterina Fake [44:17] – It was literally in HTML. And then sometime around that time, there’s blogging software appeared. Which was kind of a revelation. They were always things like Geocities and… This is starting to sound like kind of grandpa in the creaking rocking chair talking about when I was a kid, but it was like Geocities, and Diaryland, and all these kinds of things– That were like back in the olden days. Then Blogger came out.

Craig Cannon [44:43] – Yep.

Caterina Fake [44:46] – And then Movable Type.

Craig Cannon [44:47] – Yup.

Caterina Fake [44:48] – Which eventually became WordPress. I started using both of those actually. I just found my Blogger archives online, which was kind of amazing to find.

Craig Cannon [44:59] – That’s great.

Caterina Fake [45:00] – And so I’ve had this blog. I’ve had the blog, which I maintain to this day at, which I had started in circa 1998, roughly around then when I got my handwritten– Reverse chron.

Kat Mañalac [45:15] – Right.

Caterina Fake [45:16] – Blogs, literally. There wasn’t any blogging software at the time. Not only that, but the blogging community was actually very small. We all knew each other. I knew Mena Trott from Movable Type. I knew Ev Williams from Blogger. I knew all of these people. And it was just a very, very small, and very rich community, actually. Very close, we all read each other’s stuff, and so it was a really great core community to start with. Not only that, but they had the ability to talk about new things including your photo-sharing product, too. But it’s interesting, because one thing that I should note is that the way that Flickr really took off– Was that it was at the time thought to be extremely expensive to serve photos. It was. But we knew that the cost of storage was declining, and the cost of serving photos was declining, and more people had broadband at their house. We’re talking about like circa 2003.

Caterina Fake [46:31] – It seemed counterintuitive to allow people to hotlink, “your photos” to your blog. We realized that actually it wasn’t going to be that expensive, because the costs were just declining month over month. The way that Flickr really got going was when we allowed people to embed their photos on their blog. Because Blogger and Movable Type, neither of them had the ability to serve photos. One crucial thing happened is the number one question that was asked on the Blogger FAQ was where do I host my photos? And the guy who wrote the FAQ wrote Flickr.

Craig Cannon [47:17] – Wow.

Caterina Fake [47:17] – Flickr is the place that you can put your photos. Then people started using it.

Craig Cannon [47:22] – Did you guys have some watermark-type thing going on?

Caterina Fake [47:24] – Yeah, yeah. We said we’re happy to host your photos– So long as you link back to Flickr.

Craig Cannon [47:32] – It’s what happened with Imgur and Reddit. Same thing.

Kat Mañalac [47:34] – Same thing.

Caterina Fake [47:36] – I think that that was tremendous, because suddenly we were on blogs all over the place. People like, “Oh, well, obviously, if you’re going to have a photo.” And eventually, they did enable people to upload photos to Blogger. But it was a long time coming. In that intervening several months, we just grew like crazy.

Craig Cannon [47:55] – Interesting. I heard the same thing about Twitch writing their own encoder. They realized there was this massive cost savings at this certain point in time, and that’s what allowed them to become profitable.

Caterina Fake [48:08] – Sure.

Craig Cannon [48:08] – To become this gigantic company.

Caterina Fake [48:09] – Right. Because you could kind of see the cost of storage and bandwidth declining like this. You could just see it happen, and you kind of knew what that trajectory was going to end up at.

Caterina Fake [48:21] – You’re losing money now, but you won’t be losing money later.

Craig Cannon [48:25] – Interesting. Basically, you created your own little personal brand like back in the day and that’s what–

Caterina Fake [48:34] – I would never call it a personal brand.

Craig Cannon [48:35] – I know, I’m kidding. But you know what I’m saying.

Caterina Fake [48:38] – Let’s not go there.

Craig Cannon [48:41] – I know what you’re saying. Because people ask this stuff all the time.

Caterina Fake [48:43] – Sure, sure.

Craig Cannon [48:43] – And you being, I guess, designer, historically trained, right?

Caterina Fake [48:46] – Yeah, historically I was. That’s kind of how I got into the internet. Because like I was this painter who failed at Wall Street for various reasons. Then moved to California, because my sister was out here. The web was happening. I thought to myself, “Oh, well, I can parlay my synthetic skills into a design job.”

Caterina Fake [49:07] – I already knew how to code. I was always very nerdy kid. I had my own computers, and I knew how to kind of really do very basic programming. But I always had a interest in, an interest in it. That’s how I got started. I kind of was self-taught.

Craig Cannon [49:24] – What about when you’re an investor, what are the things you’re looking for in founders? These are kind of ways as a founder you might be able to attract more users. But how as a founder, or as an investor now, do you attract investors? Is it just as simple as make something people want, make something great?

Caterina Fake [49:43] – Yes and no, because you can actually make something that people want desperately, and it won’t work out. I think a really instructive study was done by Bill Gross. Of Idealab, who I don’t know how many, like 500 companies have gone through there. And at some point, they had a fairly large pool of companies that they had incubated there. Kind of it was like Y Combinator before Y Combinator. It was like ’90s, not Y Combinator. He looked at the companies that had succeeded and those that had failed. They looked at a bunch of different aspects that you could measure the companies in. Was it in a large market? Did it have a very strong founding team? Were they execution-oriented? Was their timing right? Were they first to market? All of these different things that investors had historically looked at as leading to the success or not of this company. He found that, without a doubt,

Caterina Fake [50:44] – the single biggest factor of the success of the companies was not the individual contributors, their business plan, their market, but their timing. I know this because Flickr came out at a point when Friendster had already gotten people used to the idea of putting their pictures online and having an online profile, number one. Number two, more than 1/2 of US households had broadband, could download a photo, like literally. Three, more than 1/2 of the cell phones were shipping with a camera. It was unstoppable, it was a juggernaut. It grew so fast. Its timing was perfect. It was perfect timing. I know this, too, because other companies that I have built, Hunch, I think Hunch was about five years too early.

Caterina Fake [51:45] – Findery was about two years too late. It’s super interesting how these things work out. When we’re investors at Yes VC, when we look at investments, we try to find what we’re calling movements. We looked at those companies that I mentioned earlier, Etsy, Kickstarter, Cloudera was an investment. And what was happening around them? What was timed right? Etsy came to kind of represent the DIY handmade, anti-big box retail movement. It was a movement. And it’s funny, because I took it all around the Valley, and I took it to all these kind of big-name investors, all of whom you’ve know well and have heard of. And they’re all kind of like, “Wait, so let me get this straight. It’s a bunch of women sitting around knitting sweaters and selling it to each other.” And I’m like, “Exactly.”

Craig Cannon [52:48] – It’s going to be huge.

Caterina Fake [52:50] – Right? They could not see it. Right.

Caterina Fake [52:53] – But you got to understand there’s this like groundswell. And it literally the next decade– Was about handmade this and artisanal that.

Kat Mañalac [53:01] – Right.

Caterina Fake [53:02] – I was an investor in Blue Bottle Coffee. It was the same thing. It was like artisanal food was just like the decade was about that. Cloudera was open source. Kickstarter basically came to represent crowdfunding. When you actually look at the cultural changes that are happening around your product, if you have the ability to spot a movement like that, a big cultural movement like that, everybody’s traveling in the same direction. The reporters and the journalists want to report on that. People are suddenly becoming conscious of the fact that they can have artisanal pickles. Really? We don’t need artisanal pickles, but suddenly, everybody’s desiring them. You see what I’m saying? There’s this sort of groundswell of movement. You’re a surfer.

Caterina Fake [53:50] – You see the big wave, and you’re like, I’m on that wave. Being able to kind of see that, hone your kind of eye in your heart. All of your kind of senses towards that is tremendous. Because everything around you wants you to succeed. And so if you can find that, as an investor, that’s–

Craig Cannon [54:21] – That’s it.

Caterina Fake [54:21] – That’s an amazing thing.

Craig Cannon [54:22] – As a founder as well.

Caterina Fake [54:22] – That’s the thing as a founder as well, honestly. Figure out the thing. Not just make something that people want, because a lot of time, you can make something that people want, but not enough people want it, or they’re not aware that they want it, or the culture’s kind of gone beyond it, or ahead of it, or like–

Craig Cannon [54:39] – Well, especially if you’re taking VC.

Caterina Fake [54:41] – Yeah, especially if you’re taking venture–

Kat Mañalac [54:44] – Funding.

Craig Cannon [54:45] – Wrapping up, people can find Should This Exist? on iTunes.

Caterina Fake [54:50] – Yes.

Craig Cannon [54:50] – And we’ll link it up.

Caterina Fake [54:51] – Excellent.

Craig Cannon [54:52] – Cool, I’m sure it’s going to be great. But if I’m a founder, what questions should I ask if I should maybe, should this exist? Should I make this thing? What would you suggest as like an exercise?

Caterina Fake [55:07] – There’s a really good kind of framework for asking these questions. I honestly think it’s not just a single question. It’s not at a single time. It’s something that you just have to build into your process as founders and as employees, actually, because there’s more people joining startups than founding startups, so I think it’s the responsibility of a lot of people on the team, like you mentioned earlier, to be just asking that question, should this exist? It can be the same question, at different points in the game. If I make this decision about the design of the recent activity so-called feed– Should this exist? Is this a feature that people want or need? Is this going to end up, let’s do a thought experiment. Let’s just sit down, and kind of imagine if this thing becomes the thing–

Caterina Fake [56:05] – That millions of people use. Just like think it through. Put on your kind of doomsday scenario hat.

Kat Mañalac [56:15] – You’re a science fiction author.

Caterina Fake [56:16] – Your science fiction, dystopian novelist hat. Let’s say I’m just the most pessimistic person on the planet. Find the pessimists around you. We’ve all got them in our lives. They especially stand out to entrepreneurs, because they really– They’re looking at things this way, and we’re looking at things that way. Bring them in, and say, look. Those people who are just kind of like, “No, no, that’s bad, it’s going to be bad,” listen to them.

Caterina Fake [56:47] – And kind of figure out– Are they right? Are they right? Could this end up there? Sometimes just seeing it for the first time is enough to be like, “Ooh, we’re going to change that feature,” or “We’re going to build an admin function that prevents that from happening. We’re going to take a totally different data set and feed it into our AI, so that we don’t have that outcome.” That’s it.

Craig Cannon [57:16] – That’s great. Well, thank you for coming in.

Kat Mañalac [57:18] – Thank you.

Craig Cannon [57:19] – Thank you so much. This has been fun. All right, thanks for listening. As always, you can find the transcript and video at f you have a second, it would be awesome to give us a rating and review wherever you find your podcasts. See you next time.


  • Y Combinator

    Y Combinator created a new model for funding early stage startups. Twice a year we invest a small amount of money ($150k) in a large number of startups (recently 200). The startups move to Silicon