Skip to content
20VCOct 1, 2020

What Is Founder Narrative Fit and How to Detect and Invest In It

How To Avoid Consensus Thinking When Investing, Price Sensititivity; When To Pay Up vs Stay Disciplined & From New York Times To General Catalyst; Why Venture and Journalism are Not S

With Harry Stebbings · Katherine Boyle

Full transcript · 47 min · 11,246 words · 2 speakers

Cold open

This is the twenty minute VC with me, Harry Stebbings. And on Monday, we have Palma Lucky on the show, founder at Anduril. And I mentioned this week’s shows are connected because our guest today invested in Palma’s seed round with Anduril. I also wanna take a minute to say, you’ll hear her quality in the show, but I think she’s one of the most under the radar talents and future stars of the venture community, really one of the best of the best. And so with that, I’m so excited to welcome Katherine Boyle, partner at General Catalyst, one of the leading venture firms of the last decade with a portfolio including the likes of Stripe, Snapchat, Airbnb, Canva, Cazoo, the list really does go on. As for Katherine, at GC she’s led deals in game changing companies such as Anduril, Nova Credit, Spring Discovery. Prior to GC, Katherine entered the world of venture with Founders Fund and before that spent an incredible four years at The Washington Post where she investigates entrepreneurship in many different forms. I also wanna say huge thank you to Hemontanesia, Jeff Lewis, Trae Stephens, Misha at Nova Credit, and Rachel at Guild Education for some fantastic questions and suggestions today that really did make such a difference. But before we dive into the show today,

Harry Stebbings0:00
· Sponsor read0 min · 442 words
Harry Stebbings

I’m sure you’ve heard me talk about it before, but I love Carter. Carter simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carter.com/20vc to get 10% off. More than 800,000 employees and shareholders use kartar to manage hundreds of billions of dollars in equity, and kartar now offers fund administration so you can see real time data in the kartar platform and work with kartar’s team of experienced fund accountants. As I said, head over to carter.com forward slash two zero v c to get 10% off.

And speaking of a transformational product like Carter there, 2020 has been a year full of unexpected changes, but one thing that’s remained very constant. The most important part of a company is its people. In a world with distributed workforces, it’s more important than ever to align, engage, and develop employees. And that’s where Lattice comes in. Lattice is rated the number one people management platform by real users to help companies develop engaged and performing teams. And because Lattice is trusted now by over 2,000 companies like Reddit, Slack, and Postmates, you can trust Lattice to build a high performing culture.

Companies who leverage the Lattice platform see improvements in retention, engagement, and productivity. And Lattice is the only solution that connects performance management, employee management, and now very excitingly with the launch of brand new Lattice Grow career development in one unified platform for people strategy. Our remote teams need more support as we all navigate to find our new normal, so head over to lattice.com/20vc to find out more. And do you ever wish that you were in some of the best performing IPOs of 2019 and 2020? R crowd investors were, and now you can join them in what’s next.

With r crowd, accredited investors have access to invest directly, easily, and most importantly, early. R crowd investments have IPO’d like Beyond Meat or been bought by companies like Intel, Nike, Microsoft, and Oracle. And today, you can join investment in Mimic. Mimic explains that their tiny robotics allows surgeons to be less invasive and safely perform gynecological surgeries so women heal faster and have less scarring. Mimics is a much needed innovation in the rapidly growing multibillion dollar robotic surgery market. You can get in early on MEMIC and other unique opportunities at rcrowd.com/vc.

If you’re interested in investing, you need to join rcrowd. The rcrowd account is free. Just go to rcrowd.com/vc. That’s ourcrowd.com/vc. But now it’s time for the show, and I can’t wait to introduce Katherine Boyle, partner at General Catalyst. 3210. You have now arrived at your destination.

Conversation

Harry Stebbings3:35

Katherine, I’m so happy to be doing this one. I’ve heard so many good things from Jeff at Bedrock, from Palma Evangel, and from Rachel at Guild. So thank you so much for joining me today.

Katherine Boyle

Thanks so much for having me, Harry.

Harry Stebbings

Not at all. I’ve been looking forward to this one, but let’s start with a little bit on you. And I always believe that journalists make the best investors for obvious bias reasons, but I do wanna start on a little bit of that. And how did you make your way into the world of venture and come to be a partner to stay at GC?

Katherine Boyle

Well, I’ve definitely had a circuitous path to venture. I began my career as a general assignment reporter in the feature section of The Washington Post. And really, the only requirement for that job is just that you have to be extremely curious about everything and be able to write on deadline. So I begin my week by doing an investigative deep dive into the finances of the Smithsonian Institution, Institution, and I end it by hopping on a plane and going to California to write a 5,000 word piece on Carol Burnett, who’s the godmother of sketch comedy.

So it required sort of this rabid curiosity about everything in the world and really a love of the adrenaline rush of having a new assignment every few days. So I probably would have been a journalist the rest of my life had it not been for just a terrible business model when I was at the Post. So I was there from 2010 to 2014, and it was really dire Straits. It was before Jeff Bezos bought the paper. And I actually had an editor pull me aside and say, Katherine, you’re young enough.

You can do something else with your life. You should probably leave. And I was really somewhat despondent about that, but I had a good friend who was at the Post, and her husband had just gotten out of the Navy. And she said, my husband just left the navy, and he’s going to Stanford Business School. You don’t have to know anything about business. You should apply there. So that sounded great to me. It sounded like a nice life raft. And so I applied and was was fortunate enough to get accepted and moved out to California.

And I quickly became somewhat bored by the business school experience, so I just started reading as many books as I could about technology in Silicon Valley and everything that was happening in this world. And I stumbled upon a book called Zero to One by Peter Thiel, had just come out. And that book changed everything for me because I was used to these airport business books, and that book is truly a philosophy book. So I emailed Peter, and he responded, he put me in touch with Trae Stephens, who was a partner at Founders Fund at the time.

And we got to having many conversations about the meaning of venture and what startups mean. And after every conversation, I sort of asked him, can I work at Founders Fund this summer? And he said, absolutely not. We have no idea what we would do with you. But after, I think, multiple conversations and me prodding everyone on the team, they finally said yes. So I worked at Founders Fund for seven months, and it was really the ultimate kind of experience and venture. I was a true outsider at the time, knew very little about it meant to be a venture capitalist, and it was really the ultimate gift to kind of see their thinking and be immersed in that world.

And when my internship ended, I was sort of convinced that I had to be a venture capitalist, and I couldn’t do anything else. So I talked to 45 different firms in Silicon Valley and had a lot of figurative doors slammed in my face. It was quite a trying time. But then I met Heymantir and Nico Benazoo at GC, and it was so striking because it quickly became clear that they were really interested in my quality of thought. And they weren’t interested in was I investment banker or did I come from the right company.

They were very interested in how journalism would actually help me in this career. And so I was really lucky again. Joined as an associate in 2016, and I’ve been there ever since.

Harry Stebbings6:30

It’s so funny you say about that because when I was 18 and I was desperate for a job in venture, there was one person who was the most active in wanting me to join the industry and kind of proactively talking to me about working together, that was Nico who completely ignored my lack of credentials and lack

Katherine Boyle

He’s wonderful like that. Absolutely.

Harry Stebbings

So I’m totally aligned there. I do wanna ask a couple of things, unpack the background there, and it’s you mentioned the journalism. It’s a rare background going into venture. So why is it, do you think, that you believe venture is like journalism? I’ve heard you say that before. Why is venture like journalism?

Katherine Boyle7:00

Yeah. Well, I always joke that they’re the exact same job, except in journalism, you write a story, and in venture, you write a check. But you really are hunting for the same things. So the three components of a great story are strong protagonists, a contrarian hook or thesis that really makes people’s eyes light up, and sort of this why now question or the macro change that’s happening that’s leading for the story to be relevant. And that’s exactly what we look for as early stage venture capitalists.

Beyond that, the day to day is actually pretty similar too. You have sources that are on rotation that you’re constantly texting, trying to get the scoop from. You’re competing against hundreds of other people who are trying to usually get into the same story. You’re doing diligence, and you’re making snap judgments based on very limited data. I’d say the biggest thing I took away from journalism that has helped me in my investing career is this understanding of what conviction looks like. I very much believe that investing is this unique combination of reason and revelation, and that understanding that mix is sort of the key to being a great investor, and I think it’s also the key to being a great journalist.

So I definitely feel like that was something that I got my journalism training. But there’s also a lot of differences. I mean, I’d say the biggest difference is the probabilistic thinking that you have to have as an investor. That’s definitely not something that journalists think about in terms of looking at upside or looking at opportunity. So that was probably the big shift that had to happen in my kind of mental framework.

Harry Stebbings8:11

Katherine, I have to ask. When you said about reason and revelation there, can you unpack that for me? I haven’t heard that before, which is quite rare considering I’ve done over two and a half thousand episodes. What do you mean by reason and revelation?

Katherine Boyle

Sure. It’s kind of wonky, but I studied political philosophy for a very long time, and that was what I studied in college. There’s this one great philosopher named Leo Strauss who talks about sort of human beings being this combination of reason, which is very much defined by Athens, the city. And Jerusalem is where we define ourselves in terms revelations. There’s sort of these gifts and secrets that we try to look for in the world that we don’t know where they come from, but they’re insights that all of humanity feels.

And I do think that that is early stage investing to a t. It’s this rare human combination of you look for as much data as you can and you try to build these logic trees, but at the end of the day, you’re making these instinctual choices based on sort of revelation. And I think, you know, other investors will call it secrets or they’ll say they’re looking for a hook that other people don’t see or or sort of contrarian narrative. But I really think it comes down to just this weird balance of what makes us human.

Harry Stebbings9:06

I’m also interested. You said about kind of the element of conviction there, and it’s a word bandied around quite a lot in venture. And a lot boils down to the investment decision making process. Founders Fund is quite famous for having quite a a loose investment decision making process, not with the kind of traditional partner meetings every Monday. In terms of conviction and investment decision making, how do you think about the two and avoiding consensus thinking with the unanimous investment decision making?

Katherine Boyle

How do you think about that? It is probably the hardest part of the job because once you have to constantly be optimistic and be thinking about, okay. Do I actually believe what I’m hearing is true? But you also have to be kind of practicing skepticism and questioning your own assumptions. And I think that’s what’s really interesting about investing is that you are doing this sort of as a solo practitioner. You have to have sort of this internal dialogue of, is what I’m hearing true in the same way that a journalist would sort of say, okay.

Are these facts correct? Is it checking out? But you have to also be able to sort of dream the big picture and really do you believe. And that’s more of a faith question. And that’s where I think the partnership model really helps because the people that you spend the most time with and venture are really gonna press you on. Do you actually believe what you say you believe? Are you falling into biases or traps about what you tend to prefer to see in a founder or a company?

So I think it’s definitely an art, but in terms of building conviction, for me at least, it’s a very personal thing, and it’s very much this balance of faith and reason. And then I love having my partners who can test me on whether I actually believe what I’m saying.

Harry Stebbings10:25

In terms of kind of challenging your thinking, I think, you know, Founders Fund would probably be the firm that stands out for kind of challenging one’s thinking. Such a unique firm. I’m intrigued from your time there. What were your biggest takeaways? Because it was such also an impactful time in your kind of venture career being the first exposure. How did it impact your investing mindset?

Katherine Boyle

It’s interesting because I think the biggest takeaway for me from Founders Fund is also something that I really love about GC, and it’s that they both believe as firms that there’s no one right way to practice venture. Everyone at these firms takes pride in the fact that they allow different strategies and styles of investing to prevail among their investors, and I think that’s so important. I’ll give you a few examples because I think I’ve worked with two of some of the best investors that are practicing right now in the valley, and they practice very different.

So I’d say, Hey, Monteneja is the best proactive investor in the business. He’s someone who can see the future ten years out and build companies from scratch as a cofounder with them and see them come to fruition. I think Livongo is a perfect example of that, that you saw the future ten years ago, and now you’re seeing this incredible health company at a time where no one could have predicted what we’re going through. I put Trae Stephens in that bucket as well as the cofounder of Anduril as someone who really understands how to see the future and build companies.

The flip side of that is someone like Brian Singerman, who I think is one of the best reactive investors in the Valley, where he has no theses, doesn’t think about the future, and just listens to the founder and the story and uses his own frameworks and is able to invest across a wide array of sectors. And so I think the big takeaway from my thinking there is that, you know, he was the first person to tell me that investing is much more like a multiplayer strategy game than it is like any other asset class.

And so you really have to be wedded to your own strategy and really focused on making sure that you practice in a way that’s gonna make you successful.

Harry Stebbings12:01

Can I ask, when you thought about that then and kind of carving your own path, how did you think about whether you want to be reactive or proactive, and how would you analyze what you are today?

Katherine Boyle

Yeah. I mean, it’s a great question. And I think part of being an investor is that you get to experiment with all sides of that. I’m probably more on the reactive side, to be honest. I love thinking about thesis and love thinking about the future, but at the same time, I’ve never built a company. I’m not a builder, and I’m not the sort of person who is going to partner with the founder side by side and kind of I don’t have that sort of experience that I think people like Trae and Haymont have.

But I’d say in terms of the reactive model, you’re really listening. And I’d say that the core superpower of a former journalist or the core superpower of many investors is to just listen to the story and actually decide whether you believe the story to be true. And then be kind of a helpful, almost Socratic guide to the founder on their journey to make sure that you’re pressure testing their belief in their own conviction throughout the ten year journey that you’re on together.

So that’s sort of the role that I like to play, and I think it’s much more natural for me given the fact that I’ve always been the sort of person who’s much more of a chronicler in life than the sort of person who’s gonna go out and be kind of front and center and build the future in the way that we see so many great founders do.

Harry Stebbings13:05

You mentioned the power of listening there and kind of it originating from the roots in journalism. Obviously, Mike Moritz roots in journalism also. And I spoke to Jeff Lewis, a mutual friend of both of us, an incredible investor, huge, huge admirer of Jeff’s. But if he asked specifically for you, how would you define your views and strategy vis a vis Mike Moritz?

Katherine Boyle

That is, like, the most Jeff question. Because I probably know more about Jeff’s strategy than I do about Mike Moritz. But, actually, I had a conversation with Mike Moritz maybe a year before I became a venture capitalist, and I asked him whether he thought that journalists could still become great investors given the kind of change in technology. And he was very honest. He said no. He said it’s too competitive. It’s too technical a field, and that too much a changed. And, of course, I told him that I fundamentally disagreed, and he said something that really stuck with me.

He said, no one took me seriously for the first seven years of my career because I was different. And if you go into venture capital, you have to be ready for the fact that very few people will take you seriously. And to me, that was some of the most liberating advice that I had received because this field is so mimetic, and so many young people start at their careers wanting to impress other investors. And they’re desperate to get into the hot deals because other people say they’re hot.

And when you let all of that go and you invest on your own conviction, you get to invest in things that other people overlook. And I’d say, like, in 2017, Anduril was a perfect example of that. There were very few traditional firms that were looking at defense or looking at a company with that big of a vision. And so I actually think it’s a true competitive advantage if you can kind of let go of what are other investors doing, what are sort of the hot sectors that we should be in, and really focus on your own conviction.

Harry Stebbings14:32

Can I ask sorry? I’m using this completely as my own advice platform here, but you can always be better. How do you avoid that? Because it is very tough to not get caught in the cyclone of hype, the cyclone of preemptive rounds, quick up rounds bluntly, and actually stick to thesis when so much of the surroundings aren’t.

Katherine Boyle

Yeah. I mean, I think I have a pretty strong framework for what I’m looking for in terms of I invest almost solely in what I call founder narrative fit, where I’m really, really focused on kind of certain traits in a founder. And I spent a lot of time kind of digging into that. And what’s interesting is that I’ve seen a pattern in my own thinking where the founders that I’m really impressed by, whether it’s Palmer and Brian at Anduril or Misha Nova Credit or Rachel at Guild, they’re people who are so obsessed with a sector that the deeper you dive into it with them, the more questions you ask them, it’s like going down a rabbit hole together.

And I’d say there’s very few founders that have that quality. So I haven’t had a hard time kind of straying from my own conviction that that’s exactly what I’m looking for in people. But I think it’s hard. I think it means that I don’t spend that much time with other investors. I have a small group of people that I spend time with, and I really look for founders who have sort of a deep understanding of the problem they’re solving. They may not have the solution yet, but they’re obsessed with the problem.

And I’d say that’s sort of what kept me really focused on sort of a framework that I have. Can

Harry Stebbings15:43

I ask, in terms of that obsession and I don’t mean this disparagingly timeless at all, but a lot of people can seem obsessed, but actually when you dig, you know, five layers deep, they’re not actually as obsessed as you think they are? And also combined with the fact that, bluntly, I don’t know much about defense really deep down or community colleges as I’m sure few VCs do. How do you think about what are the signals that to you derive founder narrative fit and true obsession?

Katherine Boyle16:05

I ask a lot of how questions. I think often the questions that we ask in sort of a thirty minute pitch meeting are, tell me about the problem, tell me about the solution, the what, how are you thinking about metrics. I think there’s nothing more valuable than time in this business, and the more time you can spend with founders really digging into how. How are you going to do this? How have you thought about this? Have you thought about the chessboard? What is the strategy? What does six months from now look like?

A lot of those how questions are more revelatory on how deep the founder has gotten into their own thesis. Usually, if a founder has a really compelling thesis, it’s something that you haven’t heard before. It usually goes against a dominant narrative or kind of a dominant belief, and they usually have so much data or so many examples that back up that sort of contrarian narrative because they’ve had to defend it so much. So I think those are the things that I really look for in sort of the founder story.

And the way it manifests itself in a lot of the companies I work with often that leads people to build in spaces that other people just aren’t building in. Often, these are very n of one companies. With Nova Credit and Misha, there really isn’t another credit reporting agency built for immigrants. No one else is building in that sector. There are very few companies, and particularly in 2017 when Anduril was founded, there wasn’t anyone in Silicon Valley building a new defense contractor that wanted to compete with Raytheon and Lockheed Martin.

And you’re right. Like, the thing about being a generalist investor is you’re probably going to learn so much from these founders. Like, if you’re investing in the right teams, they know a lot more about the space than you do. And I think that’s a good thing, but you can still test them on how they think about things. And I kind of see it in my own excitement when I feel like I’m really deeply learning from a founder. That’s a really good sign.

Harry Stebbings17:32

Totally agree in terms of that learning moment. I guess the question is you mentioned time there being so crucial, and the unpacking that really is two different elements. One for me is the compression of fundraising timelines means that when you used to have two weeks to a month to really unpack, to go five layers deep across multiple meetings with the founder, with the team, you name it, but really just engage in the process the way you’d like to. You don’t have that anymore, and it goes in a week sometimes.

And so my question to you is, how do you feel about the compression of fundraising timelines? And does it not make that discovery process so much more challenging?

Katherine Boyle18:02

It certainly does, but I also think the graciousness of founders to give you their time is part of the dance of fundraising. So whether you’ve met the founder years before or a few months before or even a week before, being able to ask the founder for their time and to ask the questions that let the founder continue to teach you, I think that is so much part of the strategy now. Because founders know when there’s deep interest and when they’re not wasting their time, just having diligence call after diligence call.

Like, there’s a huge difference between, let’s just go through your numbers or teach me the sector that you’re excited about. And I actually think that’s somewhat of the audition that investors are going on. Even if it’s only a three day sprint with the founder, the more that you can demonstrate that you are learning and the more that the founder is willing to teach you, to me, that is probably the most important part of the fundraising process.

Harry Stebbings

I totally agree in terms of kind of how much they’re willing to teach you. The other element of time that’s super important is, bloody, market timing, and it’s something that I’ve always said I don’t like to take market timing risk. I find there’s so many different risks in this business. Adding market timing and kind of consumer adoption on top of that fundamentally scares me in many respects. How do you think about market timing risk?

Katherine Boyle19:05

You know, I think market timing risk is very difficult, but I think it’s different than sort of these macro tailwinds or secrets that I look for. With macro tailwinds, there’s a real force accelerating a trend that might have been there all along, and I’ll give you an example of this. I think we’re seeing and I think every person with children right now is seeing this that, like, there is a huge change happening in k through 12 education because of COVID. And the two things that I think have really changed are parents are now aware of how their kids are learning, but they’re also aware of what their kids are learning.

I think that’s actually the biggest kind of shock that’s happened to parents during this five month process. And it’s not that devolution of k through 12 education wasn’t happening six or twelve months ago. I think if you invested in a company twelve months ago that was building infrastructure for k through 12 education, you could have built a massive business despite what happened with COVID. But the macro tailwind actually just accelerated a trend that was already in existence and sort of illuminated it for us and sort of raised different questions about it.

So I think there’s a difference between pure market timing risk, which is will we be able to see autonomous vehicles on the street within the next five years? Or the trend of we’re building infrastructure for a trend that’s a cultural trend that people care about and that’s actually emerging in society, but there might be some sort of market change or sort of macro event that leads to an acceleration of a trend.

Harry Stebbings20:17

I totally get you in terms of the acceleration of a trend. I think my question there is kind of durability and how sustainable that trend is. And that, in some ways, kind of relates to a big question that I have, which is especially kind of when you look at a lot of your companies around regulation and defensibility. Mine being like, how do you think about defensibility through regulation? I know Brian at Founders Fund talks about kind of complex coordination, especially around regulation being Mhmm. Like, the secret to defensibility.

How do you think about kind of the relationship between the two?

Katherine Boyle

Yeah. I mean, the reason I love regulation, to be frank, is that I think it’s a proxy for market size. But I think you have to look at the right regulated markets. So oftentimes, see Silicon Valley investors putting a lot of money into a company where they’re expecting a regulatory change to happen, and that goes to your question about market timing. That can be terrifying. You can totally misread Washington. But I actually like these markets like aerospace and defense where the board is set, the regulation is set, and there is a massive, massive market on the opposite end of that regulation that’s been in place for fifty years.

And if you can get through the regulatory hurdles or the procurement hurdles and see that market on the other side, you are competing against the slowest moving incumbents because they have had an effective monopoly for decades. That’s true of education. That’s true of defense. It’s true of credit reporting. And so I love companies that are really, really focused on these stodgy industries where, yes, there’s a lot of regulation in the front end, but no one has really tried to get through it recently. And if you can get through that front end regulation, there’s a massive market waiting for you at the back end of it.

Harry Stebbings21:40

Matt, when do you like to insert yourself? And what I mean by that is, like, do you have to, from a price inflection standpoint, insert yourself preregulatory approval? Help me out here. Where’s optimal from an investor’s perspective?

Katherine Boyle

I like to use example in deep tech. A lot of people were investing in autonomous vehicles a few years ago, and they were making this prediction that there’s going to be some sort of regulatory approval. Same thing with drones. There’s going to be changes in the FAA that allow for markets to open up. I think that’s really, really hard. But I think there’s a huge difference between the drones and the autonomous vehicles of the world and the SpaceXs of the world where all of the regulations were set that SpaceX went through.

They really just had to win procurement, and that’s more of a sales problem than it is we are waiting for government to approve this type of regulatory change so that we can operate. So I tend to look for markets like that. Anduril certainly are operating in a regulated market, but the rules of procurement have been set, and they’re an incredibly effective team in terms of being able to give customer what the customer wants within the confines of a highly regulated system. So I tend to look for companies like that where a regulatory approval process isn’t going to be the binary make or break of a company.

There are companies that have been successful off of pure regulatory change, but I think that often leads to a lot of people running towards a regulatory change, and that’s not sort of the way that I invest.

Harry Stebbings22:51

No. I think it’s really helpful for me to actually think about, like, the prebate industries, like you said, that with kind of military and defense where it’s prebasing. It’s not changing, but as you said, autonomous vehicles is very much in flux. So I know that’s super helpful for me to think through. I think, you know, you mentioned Andrew all that, and a big question that I’m always faced with by a lot of founders is we’re seeing more and more multistage funds really getting aggressive at seed.

You know, I have Joe from Loom on the show recently, which is a GC company that he did at seed. Amazing, by by the way. That’s gonna be a great return for you guys. Great one. But my question to you is, like, how do you advise founders when it comes to taking multi stage money at seed?

Katherine Boyle23:24

I love that you brought up Anduril because Anduril was a very special case and that this team is so excellent. I mean, it really is. I think everyone’s watching the last dance, and it really is the 98 Chicago bulls. I mean, this is such an extraordinary team that had worked together before. Everyone operating at a level of excellence that you really just never see. The real need for a company that’s going after such a big space, that really is a company that’s gonna follow in line with the Palantirs and SpaceXs of the world, is capital.

And so even at seed, I’m not sure how beneficial a seed fund would have been to Anduril in terms of really being able to help them sort of achieve this mission. But the second point, even on Anduril, for seed founders that I’m constantly stressing is that you really need to find someone who’s mission aligned. I think one of the things that founders do is they sometimes optimize for brand or they’re optimizing for round dynamics in a way that can be harmful if you find someone who’s at a certain firm that is really mission aligned with you.

And I think the biggest thing that I’m predicting will happen in the next ten years to founders is that if you plan on being a successful founder, you are going to have a target on your back. It doesn’t matter whether you are building a defense company or whether you are building a d two c shoe company. You are going to have a target, and you are going to need a board and particularly investors around you who have your back, who will run to the fire with you.

And I think that’s something that if that person happens to be at a seed fund, fantastic. If that person happens to be at a multistage firm, great. But you should really, really optimize for someone who’s mission aligned because you are putting that person on your board, and they are with you for a very, very long time. So the thing that I think founders should really focus on is who are the investors who have courage, and who’s mission aligned to stay with me for the long haul?

Harry Stebbings24:53

People always tell me, Harry, you’re such a nice British guy, but you never debate and push back. So I’m trying my best to be more discerned. What I would argue back is, like, bluntly, if multi stage funds right now is the way that I see it is, like, completely price insensitive. I’m doing deals now where I end up not doing them because bluntly, they’ll pay 40,000,000 pre when everyone else is paying 15 because they just don’t give a shit because they wanna pay a 100,000,000 at the a and gobble up more ownership there.

And it’s just kind of an ownership consumption in multiple rounds game. And then there’s also the challenge of signaling risk, which I think is very real too. And then I think there’s also the challenge of, like, price optimization, which is, like, if you take a seed firm, a stage specific seed firm, they’re aligned in terms of optimizing the price for the next round versus a multi stage firm coming in at seed who then wants to take more of the a. You’re not aligned in terms of the price optimization, they’ll wanna cram down because obviously they want the best price.

That’s how I think about it.

Katherine Boyle25:44

Oh, no. Totally. Those are all valid things that a founder should weigh. The the argument that I always make, though, is that I don’t think founders think enough about these issues of personality and courage and mission alignment. I think that’s something that really needs to be clear to a founder from day one. And the good thing about a multistage firm, and I’m not saying that founders shouldn’t work with seed firms. We’re very collaborative with seed firms, particularly at Theorelists of Stages because we see the value they can bring.

And I think that there’s many great seed investors and seed firms that we love working with, but you should always be also focusing on the long term. In a lot of cases, there’s benefits to taking capital from multistage firms because they’re aligned with you throughout the journey. They’re going to be able to continue capitalizing you, especially if you’re in a capital intensive field. That’s something where I invest in a number of companies that are pretty capital intensive, and that’s been a helpful thing that a firm like GC can bring to the table.

But I definitely think that the thing that founders should most focus on is finding the partner or the person who is really mission aligned with you and has the courage to have your back should anything go wrong. Because I think these ten year journeys, they are hard to predict, and that is what you really, really want when you’re choosing a board member.

Harry Stebbings26:46

Totally agree with you in terms of that kind of personality and that being kind of front and center. You mentioned that about kind of having essentially the capital to double down and to reinvest. I’m really interested. How do you think about the reinvestment process when thinking about reserves and whether to do the next check and bluntly, whether to lead the next round, whether to do pro rata, whether to do the minimum that you can kind of get away with without being looked at dubiously? How do you think about that reinvestment decision making process?

Katherine Boyle27:08

Yeah. No. So it depends on the company. So I’ll say, like, mean, this is a great example, but with Anduril, we invest in the seed. We also invested in the a, but we didn’t lead around until the series b when we co led with Founders Fund. And so I think the benefit there of being flexible as a multistage firm is knowing that you can build ownership over time and being flexible with the founders about what they are looking for. So I think that’s a perfect example of when you have a multistage firm and when you’re looking at companies that are capital intensive, you can be more flexible as to their needs.

I often say in the fields that I work in, it’s a lot easier to invest in seed and series b than it is to invest in a, and there’s a reason for that. And that’s because a lot of the companies I work with are deep tech companies or they’re engineering driven, and there is little traction at the a. So the company will look very similar at a series a versus a seed when you’re really betting on team and story. And so it’s hard to make that series a bet.

But at series b, usually, a lot of these companies that are either selling to government or that are working in highly regulated spaces have a significant amount of revenue where you can actually make the investment based on company traction. Traction. And so I think the benefit of being a seed through series b investor is that you can really think about when is the right time to invest. And founders also have to think about that as well, where if you are building a company that’s going to take more capital, it makes sense to raise a larger seed because you know that it’s going to take you much longer to get those series a milestones and those series b milestones.

Harry Stebbings28:24

I totally get you there in terms of kind of the larger seed and kind of the challenge of inserting yourself at the a. I think a question for you when I think about that is kind of on pricing. How do you think about pricing? I mean, I see some pretty crazy pricing say more than ever, actually, I think today. How do you think about your own price sensitivity, and how do you determine when to stretch versus when to be disciplined?

Katherine Boyle

It’s a great question. And I think if you look at interest rates and the $4,000,000,000,000 cash infusion we just had and where investors are parking their money, it’s very clear to me that that private market prices are what they are, and we can’t sort of long for the good old days anymore. I’m focused on early stage. So in this environment, I think you have to be very confident that you’re picking the right companies. It’s hard to have a lot of price sensitivity at seed or series a in this environment.

That said, I’m always amazed at investors who mock other investors for paying up for companies. And I think there’s far more shame in losing on price than winning on price. And no one really wants to say that. But I think if you are going to have that sort of mantra of, okay. This is how the world is. There are macro events that are happening that make it very difficult for us to have some price discipline. You have to be very selective, and you have to pick the right companies and be very thoughtful in your conviction.

Harry Stebbings29:26

I love that in terms of kind of the winning on price element. A lot of people say they’re not only winning on price, though. They’re also winning on time with that kind of aggressive preempting of rounds. How do you and, you know, this is kind of more and more prevalent. How do you think about judging the right time and knowing when to lean in versus when to hold back and wait?

Katherine Boyle

I think founders often set that tenor for investors, and I I usually like to put the ball in the founder’s court. I personally become obsessed with companies, I think, long before they’re raising, and I like to prove myself to the founder before working with them. And I think that’s an important part of sort of the auditioning process, if you will. But I think it’s company dependent. And if you get to know a founder really well and you have conviction before the process begins, great, especially if the founder is excited about that.

But if not, then I think they’re sort of respecting the process and respecting the founder’s wishes. So it’s very much a founder driven decision.

Harry Stebbings30:13

Totally get you in terms of being a founder driven decision. I do wanna ask one final thing before we move into the quick fire, and it’s in terms of the team and the partnership. I spoke to before the show, and he said about your ability to get completely obsessed by certain things. And he said most recently, it’s been the changes in media and journalism. So which is fine. Katherine, what and why have you become so obsessed with it?

Katherine Boyle

I’m very mindful that you’re the twenty minute VC, and we don’t have much time to

Harry Stebbings

Rebranding for the four hour VC.

Katherine Boyle

Yeah. No. I I’d be on that one, but I’d be happy to talk about media. The broader thesis that I have is that we are watching this incredible global decline of institutional trust. And it’s not just media. It’s the US government. It’s Brexit. It’s university education, the Catholic church. It’s any institution that used to hold power where transparency has crept in and led people to distrust it. And I really think that this has been the summer of a grand media devolution that’s been happening for a while, but it’s sort of finally bubbled up.

And I think there’s three causes for it. The first is this movement away from institutional credibility to personality driven news. And this has been driven by Twitter. I mean, if you are a journalist today, the most valuable thing that you can have is Twitter followers and prove to your employer that you have a following so that you can get book deals, so that you can appear on MSNBC. This is basically the massive change that’s happened to reporters. And I think that that’s had a great shift on how people think of their brand and people think of their personality.

And then second, there’s been a massive business model shift over the last fifty years. I mean, when you think about how a newsroom is built, it was built to deliver a paper. So you have people on staff who are very good at laying out page one of a paper. There’s tons of middle managers who are just looking at copy. There’s people over them who are deciding editorial decisions. I mean, when I was in it and even when I’m outside of it now, all I see is bloat.

Because the real product that people are buying is the stories. And there’s so much that goes into putting those stories together that I think is antiquated sort of business that really doesn’t make sense for the twenty first century. And so we’ve really seen sort of the devolution of that. And then the third is this amazing cultural tailwind that happened this summer that I really think is driving adoption of new media, which is the fear that you cannot write what you believe. There is so much preference falsification among reporters right now, and we’re seeing it across reporters, opinion writers.

This summer, a number of very, very smart and thoughtful people have left the New York Times or New York Magazine like Andrew Sullivan and Barry Weiss, and they’ve said, we’re going to Substack because we can say what we believe, and we can monetize this independent following on infrastructure that makes a lot more sense for the twenty first century. And so when you combine those sort of three facets of what’s happening both culturally and also from a business model perspective, you get amazing companies like Substack and Patreon and other creator led companies that allow the creator to make more money than they could in these bloated institutions.

So I just think we are going to see so much infrastructure built for this devolution trend. And finally, you’re giving tools to creators, and you know this better than anyone, Harry. I mean, look at what you’ve built. You don’t need a radio station in order to put out something that’s really captured people’s imaginations. So I think we’re just going to see more of this, and it’s a great trend for creators.

Harry Stebbings33:06

Totally. I was a kid in London with $50. So totally aligned to you there. And my questions to you are kind of twofold, and this is a very heavy question, probably the hardest question on 20 BC ever. You said that about him not being able to say what you think or feel. I don’t think we fundamentally live in a democracy anymore because I know I don’t, and I know that pretty much everyone around me is too afraid to say how they truly feel. Do you think we really live in a democracy anymore?

Katherine Boyle

It’s interesting that the question of whether we ever lived in a real democracy is is a good question. There’s a great book called Why Liberalism Failed by Patrick Deneen that I’ve been reading during quarantine and a number of books about sort of what we’re experiencing in this moment. And I think the big question that people have to ask themselves is whether we were ever really living in a society that valued free speech, and what are sort of the factors that have led people to really reframe how they’re thinking because they’re worried about sort of this authoritarian backlash.

There’s another great book about preference falsification called Private Troops, Public Lies, which is about authoritarian regimes and basically how people can’t say what they believe if they’re in a dictatorship or if they’re in a place where they have to fear that if they say something, they’ll lose their livelihood or their life. And we’ve seen sort of that current that was really in existence under the former Soviet Union move to what we call democratic countries. But instead of that being influenced from kind of the state, it’s been influenced from companies and from other people and from Twitter.

And so I very much believe that we’ve entered a time where it’s very difficult to say what you believe. And that’s why these narrow communities and these you know, whether it’s a substack newsletter or whether it’s a signal channel where you can talk to a small group of people, we’re seeing the narrowing because it’s become harder and harder to say what you believe in a broad audience.

Harry Stebbings34:35

My subsequent question, the final one before the quick fire. So what does that mean for the future of media? Does that mean like, had Chris, founder of Substack, on the show, and he said that he fundamentally thought we’d see massive behemoths like your New York Times or Wall Street Journal’s continue and prevail and be strong, and then you would see this incredible kind of long tail of creators on Substack, obviously, who would kind of persist and write their own incredible content but to very niche, verticalized audiences.

Do you think it is this kind of tiny and then huge and there’s no no man’s land? How do you think about that?

Katherine Boyle35:01

I do think that we’ll see the middle fallout first. I mean, we’ve already seen the middle fallout in terms of sort of small metro papers, and so 100%, I do think we’re going to see that trend. But what has been shocking this summer is to see the number of very famous writers who used to have their brand in their cache from the New York Times or from the universities that they’re working with. And when you look at this population, this population actually makes its money from being the chair of a journalism department and from being an op ed writer.

And those are the two institutions that I think have really fundamentally changed. One, because of COVID with the university education, and then two, the news media, just many readers and many people that used to have great trust in these institutions just no longer trusting them. So I do think you can see a shift even at the top, even at The Washington Post and The New York Times where people will opt out of those premier institutions because they value the freedom to monetize their following, and they also value the freedom to say what they think.

Harry Stebbings

Do you think it’s quite sad for humanity that we’ve kind of lost all trust in these traditionally well regarded institutions?

Katherine Boyle

Yes and no. To me, it’s probably the natural order of things that institutions become very large. And in some ways, think that people just misunderstood what was going to happen with transparency. Most of these institutions, it’s incredible to watch whether you’re talking about media or universities or even US government, sort of the use of responding directly to your consumer or responding directly to your constituent through Twitter. Sort of this transparency that we were all looking forward to over the last decade to make things just much more elucidated to us.

And I think what we’re seeing is that, actually, that transparency breeds a lot of mistrust. These institutions only have their power when there really isn’t real transparency into what they’re doing. And so I think it’s sort of a natural order of things that you would see a lot of these institutions fail or crumble and that you would rebuild new institutions for a different time period. You know, I talk a lot about the privatization of government, and that is certainly a trend that I’ve been investing on for a very long time and that a lot of institutions in government can’t actually perform civic functions anymore.

And it’s important that we have incentive structures like venture capital and like start ups that can rebuild for a new society in a much more robust way and actually provide civic services that are needed to people.

Harry Stebbings36:56

Very last one. I’m really sorry. I just have to ask it. You said that about kind of siphoning off the government elements. When you think about, like, the verticalization of traditionally kind of horizontal players like government, say, and you say, take this specific task, and there’s a company innovating in that realm. How do you think about, like, how big the market has to be for you to get excited? Do you know what I mean? How do you approach market sizing when you’re unbundling bundled propositions?

Katherine Boyle37:17

In the case of government, I mean, I think the markets are huge. I mean, you could talk about education, health care, defense and security. These are massive markets, and it’s actually pretty easy to size these markets because the federal government or the budget is public. So you could see how much the government is spending, and you can see, okay. If we add technology to this, how large will the market actually be, and will people actually pay? The big question for me is not necessarily market size because I think these are civic services that people will pay for.

The the big question is, can you deliver a product that makes the experience much more delightful and that people will pay for it? And what is that entry point? So in the education, I mean, you look at something like Guild Education and Rachel’s company. I mean, we’ve been talking about upskilling the American workforce for decades since offshoring has become the way that we’ve built. And it took a company in Denver that’s five years old to actually figure out how you align the incentives so that you can upskill the next generation of the American workforce, of the adult workforce.

And so to me, these markets are so large. It’s just figuring out how to align the incentives and how to make sure that you’re delivering a good service. Same thing with creating new defense companies like Anduril. For thirty years, the government has not been able to figure out how do we build new technology and how do we incentivize Silicon Valley to work with us. And Anduril has figured out how to align the incentives and make sure that the best technology is getting in the hands of our men and women in uniform.

These are really big markets. They’re really important missions, and you really can’t expect government to be able to do it alone. It has to work with technology.

Harry Stebbings38:37

And welcome to the four hour twenty minute VC. I’m so sorry, but now we will do the quickfire. I promise because Oh gosh. I could go on all day. So quickfire. So I say a short statement. You hit me with your immediate thoughts. Sound good? Perfect. Perfect. Yeah. I’m quite nervous to ask this you seem to have read every book, but what’s your favorite book of why?

Katherine Boyle

I think there’s books you read and there’s books you study. So my favorite book is actually one that you study, which is Plato’s Republic. But I’ll give you one that I haven’t mentioned today that I think everyone should read. I mentioned Denis’ why liberalism failed, and this is sort of the flip side of that. It’s a book that I really love by Ross Douthat called the Decadent Society, and it came out during quarantine. And it’s really about stagnation, being a robust affluent society with no meaning, and how you get out of that stagnation.

And it sort of takes the Peter Thiel approach that you have to invest in technology and you have to kind of get society excited about building for the future again. And when you compare it to the Indeed book, which is much more Alexis de Tocqueville, we have to go into the woods and create these small communities that are aligned in terms of their values. I think those are two prescriptions and two solutions that we’re actually going to see coming out of COVID. We’re going to see people building these intense infrastructure projects, I hope we do, you know, sort of the Mark Andreessen, it’s time to build.

But we’re also going to see people going into small communities and kind of rebuilding communities and living community together in a way that’s really beneficial for people, and that’s aided by remote work. That’s aided by the technology that you and I have been invested in for the last five years. And so I’m really excited to see what comes out of COVID, and I think that there are solutions that both philosophers and technologists are putting forward.

Harry Stebbings40:05

What’s the hardest element of your role with General Catalyst today?

Katherine Boyle

Oh gosh. I think the hardest moment right now is just that we’re quarantined in our houses. We’ve talked a lot about finding ground truth today, and it is really, really difficult to be a great investor when you’re only listening to mononarratives and things happening online. I actually think you have to get out and speak to people and really know what’s going on on the ground. I actually flew to my hometown in Northern Florida a couple months ago and spent about six weeks there with my family and just really did it because I wanted to find out what’s actually going on in the rest of the country.

And I think that’s so important for investors. So the thing that keeps me up at night is that we’re gonna be quarantined for a lot longer and not be able to get to this sort of ground truth because we are stuck in our homes.

Harry Stebbings

Totally agree with you. All I would say is you just listen to the twenty minute VC incessantly to get you through that time.

Katherine Boyle

I have been. Trust me.

Harry Stebbings

Tell me. What’s the biggest mistake you see founders make when raising?

Katherine Boyle

It goes back to what we’ve discussed. I think people optimize too much for brand and price and sort of short term effects, and they’re not looking solely for mission driven people who are mission aligned with them, who will have their back and have courage when things get tough.

Harry Stebbings41:06

What would you most like to change about the world of tech and venture?

Katherine Boyle

I actually think venture is actually a very great ecosystem. It gets a lot flack, but I think when you look at stagnation over the last fifty years, venture has actually been one of the few asset classes that has led to productivity and growth and new technology. So I think most of the things about venture are great. The thing that I would change slightly is the incentives are really great for software. It’s really hard to build large projects with large time horizons in the venture asset class.

And so I think that there are some changes that could be made, actually small changes in the incentive system that would probably have to be made either through tax changes or government doing some sort of incentive system that would make it better for companies that are really solving civic needs of government or building infrastructure that’s very much needed for American renewal.

And I know that that’s probably a lot to ask of government that they might add some incentives or change some sort of tax structure to make that possible, but I think that that would be the thing that I would change the most is just allowing for these large infrastructure projects or companies that are building hardware and software to be able to operate in the venture ecosystem.

Harry Stebbings42:04

Do we need to change fund structures, fund lifetimes, when you look at such ambitious plays?

Katherine Boyle

The time element is one play, but I also think whenever you are doing the analysis of whether it’s more advantageous to invest in software or hardware, you’re always going to come out saying or nine times out of 10, you’re going to say we need to invest in software. So I think that there are more tax incentives actually that I would add on that or something where the government could say, here are the five areas of interest where we know we have to work with with technologists, and we’re going to make incentive structures that allow for the returns to look somewhat similar to software.

But I think it’s hard for venture capitalists to do it alone. I actually think that this is gonna have to come from government. And I’m I’m not hopeful that that will happen anytime soon, but if I were queen of The US, that’s what I would do.

Harry Stebbings

I mean, we could just do vote Katherine for president. I mean, but then final one, tell me, what’s the most recent publicly announced investment, Katherine, and why did you get so excited and say yes?

Katherine Boyle

So publicly announced is a company called Ophelia Health, and they are building a telehealth platform for medication assisted treatment for patients who are suffering with opioid addiction. And this is a space I read a book that I recommend to everyone called Dreamland about the opioid epidemic in this country and and sort of the origins of it. And I looked for two years for a company that was solving this problem in a way that I thought could actually help people get access to Suboxone treatment, which is the only treatment that we know works most effectively for people who have long term opioid abuse disorder.

And there’s a number of companies working on it, but the difference between Zach Gray’s thesis at Ophelia was so many people focused on the assisted of MAT, which is medication assisted treatment. He was focusing on the medication. How do we get Suboxone in the hands of the most people because we know it’s effective? And so I am so excited. They’re doing incredibly well and performing a very important service during COVID, and I’m really excited to be part their story.

Harry Stebbings43:40

Katherine, as I said, I had so many great things before the show. As you could tell from me going completely off schedule and completely flunking twenty minutes. I so enjoyed this. So thank you so much for coming. This was an awesome episode.

Katherine Boyle

Thanks so much, Harry.

Harry Stebbings

As you can tell, I just absolutely love that, and I think Katherine is just one of the most under the radar stars in the venture ecosystem. You should follow her on Twitter at k t m Boyle. That’s at k t m Boyle. Likewise, it’d be great to welcome you behind the scenes here. You can do so on Instagram at h Stebbings nineteen ninety six with two b’s. However, before we leave you today,

· Sponsor read0 min · 435 words
Harry Stebbings44:11

I’m sure you’ve heard me talk about it before, but I love Carter. Carter simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carter.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity, and Carter now offers fund administration so you can see real time data in the Carter platform and work with Carter’s team of experienced fund accountants. As I said, head over to carter.com/20vc to get 10% off. And speaking of a transformational product like Carter there, 2020 has been a year full of unexpected changes, but one thing that’s remained very constant, the most important part of a company is its people.

In a world with distributed workforces, it’s more important than ever to align, engage, and develop employees. And that’s where Lattice comes in. Lattice is rated the number one people management platform by real users to help companies develop engaged and high performing teams. And because Lattice is trusted now by over 2,000 companies like Reddit, Slack, and Postmates, you can trust Lattice to build a high performing culture. Companies who leverage the Lattice platform see improvements in retention, engagement, and productivity. And Lattice is the only solution that connects performance management, employee management, and now very excitingly with the launch of brand new Lattice Grow career development in one unified platform for people strategy.

Our remote teams need more support as we all navigate to find our new normal, so head over to lattice.com/20vc to find out more. And do you ever wish that you were in some of the best performing IPOs of 2019 and 2020? R crowd investors were, and now you can join them in what’s next. With r crowd, accredited investors have access to invest directly, easily, and most importantly, early. R crowd investments have IPO’d like Beyond Meat or been bought by companies like Intel, Nike, Microsoft, and Oracle.

And today, you can join investment in Mimic. Mimic explains that their tiny robotics allows surgeons to be less invasive and safely perform gynecological surgeries so women heal faster and have less scarring. Mimics is a much needed innovation in the rapidly growing multibillion dollar robotic surgery market. You can get in early on Mammic and other unique opportunities at rcrowd.com/vc. If you’re interested in investing, you need to join rcrowd. The rcrowd account is free. Just go to rcrowd.com/vc. That’s ourcrowd.com/vc. As always, I so appreciate all your support, I can’t wait to bring an incredible episode this coming Monday with Arlen Hamilton at Backstage Capital.

↑ Top