YouSaid · the spoken record

Katherine Boyle

lines on the record: 214
first: 2025-08-30
most recent: 2025-08-30
sittings or episodes: 1
sources: podcast

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“Silicon Valley and like actually have an outpost there. So he started DIU as an experiment. It's now, you know, it's now much bigger.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Silicon Valley likes winners. So the minute that they started seeing winners, it's like, oh, okay, like you can make money doing this. And so that kind of brought along, I'd say, the rest of the ecosystem. People who maybe weren't as interested in DOD, but they started seeing things change. And then on the DOD side, I mean, I would actually say that this movement was really created by the DoD, like former Secretary of Defense Ash Carter in 2015 launched DIU. And he was the first person, I think, inside, it was during the Obama administration, he said, you have all these incredible engineers in Silicon Valley. None of them know anything about the military. Like they don't see anyone in the military. We're not out there, right? Like in Washington, DC, if you live in DC, you go on the metro. You see people in uniform. They're headed to the Pentagon. It's part of your life. So you're not as weirded out by defense culture. It's part of daily life. Silicon Valley, they don't see anything. And a lot of these people, you know, many people are new to America.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“And people started realizing, oh, there are examples of companies that have just really taken off. Andrew will change this for defense, where in the early days it was controversial. But the minute that Andrews just started just getting all of the great engineers, really just crushing it on the contracting side and just building really cool products. Silicon Valley just loves to be around cool things. And the thing that I think Elon did for the rest of the ecosystem is he made hardware manufacturing. He made space. He made these really difficult things cool again in a way that no one had ever, I mean, aerospace before him was just like a backwater. No one was majoring in aerospace engineering in colleges. No one wanted to work at those companies. And the first 10 years of SpaceX were hard. But like by 2015, 2016, they were, you know, relanding rockets. They were doing some really cool stuff. They were about to, in 2019, they were about to, you know, start star a link, which was, you know, kind of this crazy idea that no one thought was going to work and look at it now. So it's like.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“A lot has changed. And I think it was multiple things changing at the same time. So the first thing that changed is Silicon Valley likes winners. We're very memetic. You know, it's like VCs will feel very strongly about it. I don't want to work with defense company in 2017. And those same VCs will be begging to get in and around three or four years later. So things move very fast in Silicon Valley. People will completely update their knowledge. And so what I think happened is SpaceX became an extraordinary company. Palantir went public.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Serious insight. I mean, at that time, I mean, you just brought it up, but there was a strike at Google. I mean I mean, whatever you want to call it, anti Trump, but anti. It seemed like anti US. Nobody wanted to upgrade our defense tech. I mean, you're on the precipice of that change. What was it that changed? I mean, it seems like Silicon Valley's done a complete 180 now. Yes.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“You must really, you know, you're really on that mega train. Just like the horrible things people would say. And it's like, I care a lot about my country. That's why I'm doing it. And I think there's a business opportunity here, right? It's not just, oh, I'm a patriotic capitalist and I'm throwing money away. Like I think this is the biggest business opportunity of our time. And it's sitting right in front of my face and no one's looking at it. And so I'm going to invest in it. And I'm going to be the first call of these people who want to work here.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Started writing very publicly about it. A lot of people weren't even talking about it, right? Like people were still afraid of it. There were firms that still couldn't invest in it because their limited partner agreement, the sort of governing docks of how the funds they operate said they can't touch weapons. So there were firms in Silicon Valley that could not invest in Androil because their limited partners wouldn't let them. But even after in 2019 like when I made that investment, The number of founders who said like one, you're an idiot, like that's a dumb investment. They're never going to make it. Like that was common. But there was another class of people who said like, wow, you're a fascist too. You're a bad person.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Best thing you can do is an early stage investor is to build relationships with people who are director of technology. Have no idea that that's on their horizon, but you know they're going to be a great founder. And so you start building a relationship for them so that when they do leave, you're their first call. And so it actually has a lot, you know, there's a lot in common with intelligence operations where you know if someone's going to flip after you're spending years of time with them or months of time with them, right? You know if someone is going to give you good information even before they know. And it's the same thing with sourcing and reporting. Like you can spend a lot of time with the source and them give you nothing and then six months into building the relationship. They have a story they want to give you. The best reporters are like that. Same is true of venture capitalists. It's figuring out who are the people who matter and making sure that they call you first. And so that then became, I'd say after Andrew, one after Andrew, it became clear that like Catherine's going to invest in this stuff, right? Like it's like, this is what she cares about.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“And almost maniacally focused on it. I want to know their story. I want to know who they know. I want to know their network. I want to map their network because I want to know who their first 10 hires are. I want them to tell me who their first 10 hires are so that I can verify those people are probably going to join them. Like I want to understand sort of the network node of who these people are and how it's going to expand. And I always say like early stage investing, the best early stage investors are building relationships with someone who's going to build a company before that person even realizes that they're going to build a company. Like it's in some ways there's a lot.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“So a lot of it comes from the people, and that's like, I don't know much about technology, right? Like I've never built anything in technology. I'm not a technologist by nature. I've learned a lot having been in the industry for 10 years, but that's not how I make decisions. There's a lot of venture capitalists. They always say that venture capitalists have sort of three different dimensions they judge. They judge the market, how big is the market size. DOD has a very big market. Small market for startups, but a very big market. It's, you know, 800 billion and growing every year, right? It's a massive, massive budget. The product, so a lot of technologists, people who are really, really good at, they've worked at Facebook or Google or these different companies. They come out, they become VCs, and they always want to talk about the technology. How does it work? How does it operate? And those are people who, you know, oftentimes their genius level. We have a lot of them on our team, but they just, they know how technology works and they have a theory of where technology is going. I don't care about any of that. Like all I care about is the people.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I've done that before. I've changed my career. I've done things before. But if indeed this goes through and we end up leading this investment into this company, like this will be my mission, investing in America. Like this is it. This is all I care about. And like these are the companies I want to invest in. This is what America needs more than anything. Silicon Valley doesn't get it yet, but they're going to. And the minute I leave that church, you know, walking back home five minutes later, I get a call from one of the managing partners and he's like, you have the green light. Go give Palmer a term sheet.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“An ethical company. I mean, just things you shouldn't have to do, right? Like if you're in Washington, DC, if you're in a place that understands defense, you should not have to explain why supporting the DoD is good. But this was right after Project Maven. It's right after the Google employees walked out and said, we are not supporting the Trump administration and the DOD. And I haven't told this story before, but I had this moment where they were debating the ethics and I was asked to leave the room because I wasn't one of the managing partners and it was the partnership was going to make a decision. And I walked down across the street to this church in St. Dominic's in San Francisco. And I just kneel down and I prayed to God. I was like, okay, like there's a reason why I've spent a year and a half on this company. Like this is like the most important thing I've ever done, trying to get capital into this company. And if it doesn't happen, I'm going to walk in there tomorrow and I'm going to quit my job because you don't want me in venture capital. Like this is not where you want me to do. I'll figure out something else, right?”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. And that was how they were viewed across a lot of Silicon Valley. It's like too much headline risk, too much fear that Palmer is a little bit of a wild card, but also it was like, we're not going to support the Trump administration and the things that we can't do that. We're Silicon Valley. Like we'll lose our shirt. Our LPs will be upset, right? And it took to the credit of the firm I was at, like it took maybe three days where I said, no, no, no. These guys understand ethics. They understand just war theory. I ended up writing like a 16 page memo in addition to like the investment memo that talks about like the numbers and how big this company can get on just war theory on like you know why this is an ethical product like how the how the dod thinks about ethical products um you know tray got on the call with um with all the partners and he has the theology background as well and was talking about you know how how why they why they're you know seeing this as”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Diligence and meeting with as many different types of customers and operators, anyone who could possibly talk about what their tech was doing and to really showcase it to our firm. And the kind of crazy thing that happened was the story of, I think it was like 2019 when they went out to raise Palmer pitches what they've done. And they already have, you know, towers on the border that are actually working. Like they're already selling to the Department of Defense. They've moved exceptionally fast. And he goes into the room after I've done, you know, all this work to try to show that this is an incredible investment. And one of the partners kind of raises his hand at the very end and says, like, are you ever going to build missiles? Or are you ever going to build weapons? And Palmer says, of course, like we're going to build with the DoD wants us to build to protect the warfighter. The great answer, like he leaves the room and people are like, we cannot invest in this company anymore. We cannot invest in this company because.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't want to say throwing away their money, but it's like this is kind of a crazy, it's a huge crapshoot, and then it was about like a year and a half of like really working with them because I was, you know, I was young. I was enthusiastic, but I, you know, you know Joe Lonsdale, who had already sold multiple companies, he was involved in the company. There were a handful of other people involved. But for the first, you know, the first big round that they were doing about a year and a half later, I was like, I want to lead this round. I want to put, like, I want our firm that I was at to do the big investment into your company. And it took, you know, six months of.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Like a couple million dollars, and they had raised what was at the time a very big C round. It was a $17 million round. And people thought that was insane. I mean, now you're seeing seed rounds of hundreds of millions of dollars, but this was because Palmer was extraordinary. He was an extraordinary founder. He had an extraordinary exit. But there was definite concern, particularly among the early investors of, okay, like, is this a company that's even going to be able to raise capital? Because no one actually believes that you can sell in the Department of Defense. Maybe the border security thing can happen, but like, this is so crazy. Like everyone felt like they were, you know, kind of.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“But it was like Palmer Lucky? The guy who just got fired for the Hillary Billboard, like the fascists, the fascist guy in Silicon Valley. And what's company do? Well, they're building a border security company. Oh, they're building a border security company to help ICE. You know, like, I mean, it was immediately I was sort of outed in my firm as, or Catherine's kind of insane, but they're like, we're not like, we're not going to do that. And it was pushing, I pushed a bunch and finally we got a tiny little check-in. And the conversation wasn't even about the company. The conversation was about, well, if it's this small of a check, like, you know, like, like we'll see what happens, right? But it sort of like kind of, you know, skirted in a small check into the seed round. But that kind of gave me entree.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I want to be an investor in it. I want our firm to be an investor in it. I'm going to get it done. Of course, I can't make that promise because I'm nobody, right? But I immediately, you know, drive home, call the partners and say like, I'm or lucky starting this company. And we need to be a part of it. And usually in Silicon Valley, they'd be like, oh, that's great.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes. Oh, yeah, because you come out of school and then you're the junior associate who's there to take notes, write memos, you know, you're there to learn the trade. It's an apprentice job. You can ask questions, but like you, you know, you're there to source too. You're also there to find companies and to be the first person to touch a company and bring it in. And so it's actually a funny story. I was with Trey at InQutel, which is the CIA's investment arm. They have a big conference every year. And we were at that conference. And he's like, we're starting the company. It wasn't even named Andrew yet, but he's like, we're starting the company. I knew what that meant. He's like, Palmer has just been fired from Facebook. He cares a lot about defense. I think we can convince the head of engineering at Palantir. I think we can convince some of these guys to join. And we're going to start it. And I just said, I don't care. And of course, I didn't have the authority to say this, but I said, I don't care whatever you're doing.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“So when I left business school and I ended up working at another venture capital firm, that was right when Palmer and Trey and Brian and the guys were founding Androil. And so it had the luxury of spending a year with these people really understanding how well they understood the mission, understanding how valuable Palantir talent is to people who've actually worked with the government and sort of that model. So I was probably six months into the job at this new fund and again like lowest on the totem pole. Like, you know, like.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Philosophy of how they take bets on the future, like that completely transformed and sort of catapult to me into venture capital.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“She's like, You need to take that off. I'm going to get you a SpaceX hoodie. Like, you need to wear jeans. You need to blend in here. Like, this is not going to work if you can't blend in. And I like, I'm very grateful for that because it's like she's right. Like you're learning a new culture. Like you were learning like how to operate inside of an ecosystem that's nothing like what you've experienced before. And when you understand it, then you can start being, you know, kind of yourself. You can start being a little more flamboyant when you're accepted, when people accept you as one of their own. But when you're learning the culture, like you're there to listen and you're there to work your ass off. And that's kind of what I did. And it was an incredible gift to be able to see how companies that are, you know, so iconic that no one believed in, even 2015, SpaceX was still seen as, oh, well, how big can that company become? It wasn't what it is today. And so to see people how they make bets on the future and sort of the...”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Like veterans will email me and they'll say, Miss Boyle. And I'm like, do not call me Miss Boyle. Call me Catherine. Like, you call a 70 year old famous venture capitalist by their first name. Like, you have to shed whatever you have learned in your previous life and realize you're going into a totally new culture and you have to blend in on that culture. Like you have to learn the culture. Like that's what your first year in Silicon Valley should be. And you should go to a crazy early stage startup or a venture firm that's totally different than anything you've seen and you should just listen. Because once you learn the culture and once you learn the language, then you can be an operator. But you have to learn the culture. And you have to respect it. So, you know, first day at Founders Fun, actually one of the EAs came over to me. I was wearing heels. And I can dress like this now because I'm a Florida lady, but I was in San Francisco and I was wearing heels and, you know, like nice, like I dressed like I was going to a nice internship.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I helped Trey just look at company. So I sat in on every pitch. We were just kind of surveying the landscape of which companies are operating in the defense space. Are there any sort of government companies that are actually interesting? We met the Shield AI team. Like, you know, like there were a handful of people in and around the space, but not very many. And I always say it was like a gift, right? Because it wasn't like I was giving them anything, right? Like they would tell me, hey, like maybe look for some companies or whatever. And I would try to find things that could be relevant for the national security mission. But it was really a gift. And like that, that is, frankly, that's how all of tech works, where someone gives you a break. And if you show up early, you're the first person there. You work your ass off like you do any job they want you to do. Like that, that's often what it's like to be in a startup. And I always tell, you know, I coach a lot of veterans because I have so much empathy for you're coming from a culture that is so different.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Just hit it off talking. And I said, you know, I'm really bored in business school. I need to do something this summer, but I'd also love to like just work for you guys. Like, can I just intern with you? And again, to the point of people will not say no more than five or six times. He said no, probably five or six times. He's like, we don't have a job for you. Like, what are you going to do here? Like, you don't, you don't know anything about technology. You literally just showed up, you know, like it's nice. Like we could talk. I could try to help you and things, but like you really should work at a company. Like we can't have you in our firm. And I just kept emailing like, hey, you know, like I don't really want to work in any of these companies. Can I please work for you? And after about like four or five no's, he finally said, okay, fine. Like you can, you can come work at Founder's Fun. So, you know, Founders Fund's a pretty iconic venture firm. I didn't know it at the time. But, you know, they've invested in SpaceX. Trey would go on to be the chairman of Andrew. He would go on to incubate that company with Palmer.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“About the Facebook IPO and things. So I knew who he was, but I didn't know he was as big of a deal as he has now become and kind of is in Silicon Valley. So I reached out to Peter Thiel. And what's crazy about this is, again, I wasn't expecting a response. I was very good at reaching out to people, but not everyone would respond. And I didn't get a response from him, but he had forwarded my email to one of his kind of junior partner's principals at his firm Founder's Fund named Trace Stevens. And Trey and I had overlapped in school. He had actually been at one of the agencies. And whatever I said in my email or whatever kind of context he had, you know, Peter thought we would hit it off. And so I started talking to Trey, who was brand new in venture capital. Peter had brought him on from Palantir to really look at national security and defense. And, you know, I kind of told Trey my story. I was a former reporter. It turns out he had 1.1 wanted to be a reporter in his life.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“No, and it's interesting because I know Dino has been on your show and he talked about what it was like as a veteran going to business school, right? Like you go to business school and you think, oh, I got two years to figure it out. It's like you get to business school and like recruiting starts immediately for jobs. I had no idea. You know, I was like, what do you mean? I have no idea what I'm going to do. I'm a former reporter. So there was sort of this like kind of, you know, you feel like you're on sort of really shaky ground. But I, you know, my personality is I do very well in those situations. Like I do very well when I have no idea what I'm going to do and I have to make a next move. So crazy story of how I ended up in venture capital is it was 2014 in the fall and I always joke no one in business school reads books and they have a library at the business school that has only business books but they don't have real books and I'm a reader and I walked into the library one day and there's this new book called Zero to One. It's on the on the shelf and it's by this guy named Peter Thiel. And I heard of Peter Teal because I was a reporter and I had like, you know, read.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“So, you quit your job. Just inserted yourself in the middle of Silicon Valley and just started emailing people And did you have any idea what your business was going to be, what you were going to do? You just immerse yourself in it to figure it out”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“So a young person with no experience with a Stanford email emailing you saying, hey, I'm a former reporter and I'm really interested in your job or I'm really interested in your company. Can I sit down with you for 30 minutes or get coffee or get on the phone and just hear about what you do? People will pick up that. Like people will take that call. And so that's kind of what I did. I was like, I am so confused. Like I was the worst culture shock of my life. Like I, you know, I'd been around the world, but I had not experienced sort of that insular culture of how tech companies are built. And I'm always impressed with how many people picked up that call.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“This was 2014 So, is right sort of it's funny when I arrived, and this is like a funny thing people always say about Silicon Valley, they say, you know, you always feel like you're too late, like you missed the big ones. So I missed Facebook. I had missed Airbnb. You know, it was these paland here. It felt like I had missed Palantir in 2014, which is comical because, you know, even last year, you couldn't have missed Palantir, right? It's like that company is a rocket ship. So in some ways, it's like you always feel like you've missed the boat. But when I got out there, you know, in some ways not knowing anything was really helpful because I just was sort of this, you know, former reporter emailing people, just trying to figure out what's going on. And you and I talked about this earlier. Silicon Valley's for all of its weirdness. The best part about Silicon Valley is everyone is afraid they're going to miss the next thing.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Out here and understand this culture. I don't know nothing about it. I've never met anyone who's worked in Tech or Silicon Valley. But it's clearly having an impact. And this is like the biggest story of our time. And I'm a reporter. Like I should go out and kind of figure out what's going on out there.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“So, I mean, Silicon Valley was more of okay, the biggest story that I'm writing about, you see patterns in the stories you write and the stories you write every day sort of tell the story of the country, of the ethos. I was actually a culture writer too. So I would write, I had a really broad swath of things I could write about, but a lot of things I was writing about were how technology is impacting this industry or how technology is destroying another industry and just the conversation at the Washington Post day in, day out was we're all going to lose our jobs because Facebook is gaining momentum and everyone wants to read their news on Facebook like there's no business model. And so there was something I really want to like to me this is the biggest story of my life like tech is the biggest story I don't understand it and a lot of the Washington Post people I worked with they hated tech right like they were like tech is what's destroying their livelihood and they have every right to hate it But me I was like I want to understand it like I want to go”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I've never, you know, it's like even in my business career, I was never interested in things that didn't have like where you're negotiating with people, which is a lot what BC is. I know we'll get into it. But there's something about the human component where I think that's what I wanted to do. And it was also, I don't know, I was probably so dejected. I didn't have that many mentors where I didn't have people who were like, oh, well, you should go this path or you should do this or talk to this person. It was more like, okay, they rejected me. Like there must be a reason. And maybe I'm supposed to be doing something else.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, you know, it's interesting. The woman, the mentor who had been at CIA, she was like, do not go to CIA, go to state. And I was like, that sounds boring. I don't want to go to the state part of it. There were certain things where I was just like, that's not going to be interesting. And I also think when I look back at my career, everything I've done has been like information trading, but it's been very human-centric. I wasn't interested in NSA. And I like the human connection.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“To do a story, I was like, this is the story I'm working on. And I think it's relevant to the class because of this. And I think after enough annoying emails, and this is a really important life learning, but there's a, if you're the most annoying person. Any admissions group, but like really to any company, if you're just like constantly pounding down the table or any customer, like people just finally give in. Like people will not say no 25 times. So it was, so I got in last minute and it was sort of, it was like, okay, I'm going to Silicon Valley. I'm just going to figure it out.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Had to leave. And when she told me that her husband got in, I was like, well, I'm different. I know nothing about business. If it's really, there's really no, you know, you just have to, you know, get a decent score on a test and write a good essay. I'm like, I know I can write an essay. That's like probably one of the few things I can do. So I got really, really lucky. I got off the waitlist last minute. I actually found out I was on the waitlist on a reporting trip to Beirut. I was like, I was on the, I was on the plane and I was like checking my phone and you're supposed to get a phone call from the dean of the school and like no one's ringing. And as I'm like taking off to go to Beirut from DC, I'm like, I'm not getting in. Like I'm just going to be a reporter forever. And I land and see the email. And it's like, you know, you're on the wait list. And I'm like, okay, that's not a no. It doesn't mean they want me, but it's not a no. And so I just sent a letter pretty much every day. I was like, I'm in Beirut. You know, every time I would go to a new place.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Ego, it's desperation. I don't want to lose my job. We're bigger than this. We're the Washington Post. We're the brand. We're like everyone needs us. But I think this is true of humans that are in these kind of grand institutions. They can't recognize when something's crumbling. You see it happening with universities today where these universities are sort of in some ways in major crisis because of what the students are doing and they just can't ever see that things need to be reformed. Federal government too can't see that things need to be reformed. But that was certainly like a learning for me where I saw it because I wasn't wedded to it. I hadn't been there during the heyday where everyone was getting to fly wherever they wanted. They could be bureau chief of any country. They wanted to be bureau chief of. I mean, we had shuttered all of our international bureaus by the time I had gotten there. So it was a paper that was clearly in decline. And I saw it. For me, it was just, okay, this is a job. I can learn something. And I original gene didn't work out. But I knew it.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“So I kind of knew it was going to be a temporary thing just because of how bad the business was. I mean, it was all we talked about was, you know, this was before Jeff Bezos bought the paper. And I actually decided to leave right as he was buying it. And a lot of people, you know, said that was the saving grace of the paper. One of the richest men in the world buying it, putting money into it so that it wouldn't go down the drain. But what happened actually was my best friend at the Washington Post. She was the religion reporter. Her husband was in the Navy, and he had just left the Navy and he was going to Stanford Business School. And I knew nothing about business school. I was stunned he got in. I was like, I didn't know your husband knew anything about business. I thought he was in the Navy. And she's like, no, no, no. Like the business schools take like 5% of their class every year. They call them not.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I think you can get dropped into any culture and learn it very quickly. If you know the types of people that are going to talk to you and if you're actually willing to listen.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“And they're desperate to get that type of attention. And so it really, like in some ways, I think the reporting thing was easier than when I got to Silicon Valley and was nobody, right? It was like I was a Washington Post in Washington, D.C.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Knows nothing and you call someone and you say, Hey, this reporter from the Washington Post, can we get coffee? You know, I just love to hear more about what you know. Can you show me what I should know about this beat? Like the, like you do that over and over and over again. And people will tell you what you need to know. And then they start seeing your name in the paper. And then they know that you're the person who's going to write the story about something. I also think there's something to some people are really good at listening and it's a gift growing up in a big family was probably that. Allowed Irish family. I learned how to listen. But I'm always amazed at like the stories I would break. It would just be someone coming up to me at a cocktail party or a book party or something. Not even necessarily knowing that I was a Washington Post reporter, finding out and then just kind of sharing, just like just getting it off their chest and me saying, you know, that's actually a really important story. Can I write it? But I think people are desperate to talk.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, yeah, I mean, it's a good question because it's also what venture capitalists do. Like, how do you get dropped into a culture you know nothing about, which was the case with VC, and start meeting people and start building up relationships. And I think like, you know, the interesting thing about doing it as a reporter is they give you a beat. Like my beat in the beginning was like retail and the business of, you know, like almost like the business of arts and culture. And then it moved on to like nonprofit investigations. So I started researching like the Smithsonian Institution and all of the government funded agencies in Washington, D.C. and art agencies and different things and sort of where they were getting their money from and kind of follow the money but of the nonprofit areas. But it started out as like, okay, like you get your assignment and then you just start calling people. And the thing I know you know better than anyone else is like people just love to talk. People will tell you anything if you will sit there and listen. And when you're a 24, 25 year old”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“In your newspaper, no one's reading the physical paper anymore. They still had it and they still had subscribers that were reading it. So it was actually a great time to go in and just be like, okay, like I'll work for basically very little and I'll work a lot and I'll fill your paper. And so after about a year of that, they brought me on full time as a staff writer because I was breaking stories and things as someone who really wasn't affiliated with the paper. But it was not what I wanted to do. It was not like my dream was to be, you know, a reporter, but there was something about just being in that place at the right time where I was like, okay, I can make something out of this major setback or this thing that I thought was a major setback. And I can learn a new trade even if it's not the thing that I thought I would be doing.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, I mean, just the business of media with the internet Everyone thinks that the media really started declining like maybe 2014, 2015, 2016. But the first wave of real layoffs were like 2008, 2009, where there was just an understanding that Google and then Facebook, but Google really was just eating the lunch of these companies. The business models of every major newspaper up until this point of regional newspapers were classified, you know, subscriptions and then syndication. So syndication, sending out the story, people paying to have to reprint it. That was Google. Google completely took that, right? Like, so all the stories would go on the internet for free. No one was paying for the digital copy. The Wall Street Journal figured it out, but none of the other papers did. So they were just hemorrhaging subscribers. And then the advertising, it was like, well, if people are advertising online, like, why am I going to advertise my store in your?”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I just have to convince them to let me do it. And turned out to be the most opportune time to be in media for a young person. Yeah, because I was cheap. I was making $30,000 a year. And I would write as much as they wanted me to. I'm like, I have no obligations, right? I can come in on Sundays. I can do whatever store you want me to do. So I found an editor inside the Washington Post and she's like, you can write as many stories as you want. We just need people to fill the actual physical paper because they were slashing the people who were well-known reporters left and right because the business was going under.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“And then do what I need to do for my real career, my real job, right? You know, I was so convinced that was going to happen. And so when I got the letter, I was like, wait, wait, I'm just right now. I'm just a copywriter at, you know, the lowest person on the totem pole inside the Washington Post without a byline, without anything. I'm not even a real reporter. Like, like, what am I going to do? Like, what am I going to do? I should probably figure out if I can actually make this a real career. So I sort of, you know, I sort of convinced myself that intelligence isn't that different than reporting, right? You have sources. You have to have a network of nodes and people who are telling you information about whatever you're covering. You know, you have to be really good at asking questions. You have to be good at listening. Reading people, knowing what's true, knowing what's false, making decisions very quickly. And part of me was like, okay, if I can't do that as in the agency, I could do that at the Washington Post.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I think she did me a favor. But it was definitely like coming out of college 24, no idea what I was going to do with my life. And it was sort of serendipitous how I ended up at the Washington Post because I had taken a job and I had friends who were already sort of in and they're like, you got to be in D.C. Just take a job, like take any job you can get. And so I got this kind of ridiculous like copy editor job, but it was at a newspaper called The Express. So if you've ever been in DC and you've gone on the metro, it's the free metro paper that the Washington Post hands out. And everyone, you know, who's ever been on the metro members' paper loves this paper, it's sort of the snarky, you know, free newsletter thing. And they needed someone who was just good at writing but unbyline so you don't have a record that you work there or whatever. And I was like, that sounds great. Like I can just, you know, just write during the day for, you know, three to six hours or whatever.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“So it's on me. And they're right, right? Like, I am not the, even today, it's like my colleagues are like, it's amazing you can actually work at a company, right? You're such a disagreeable, and they mean that lovingly, but like I am not someone who doesn't say what I think. I'm not someone who takes orders very well. So I think they probably looked at my character after, you know, it's like spikes in certain areas, like probably very good at getting information and meeting people talking to people, you know, doing the things that you need to do, but also probably not going to be able to deal with the culture.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“I just can't stand not knowing. And of course, that's like the wrong answer. And to the lady who was interviewing me's credit, she was like, honey, you think you're going to know in here? You think you're going to come in here and you're going to know anything? And again, it's like, okay, you have 23 year old, like little girl who's never been told, like, get out of here about a joke.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I had done multiple interviews. Yeah. So it wasn't, it was, yeah. I mean, they did, you know, multiple rounds of interviews. And I look back on it. It's so funny. I'm like, I know exactly why they didn't pick me. I am not an easy person. I am a disagreeable person. You know, it's like after, you know, eight-hour interviews where they're really trying to get to know you. There's times where I'm like, I know exactly what I said wrong. Like you're supposed to answer the question of like, why are you wanting to do this? Right. The right answer is you want to serve your country, which is the right answer, right? And I said it multiple times, but by like the fifth time they ask it a different way. I said something that was probably the through line of my life, which is I just can't stand not knowing.”
2025-08-30 · a16z Podcast · Katherine Boyle on Shawn Ryan · IDENTIFIED FROM THE TRANSCRIPT · source