The Knowledge Project with Shane Parrish - #113 Sarah Tavel: The Value of Intellectual Rigor

Episode Date: June 15, 2021

Sarah Tavel has spent the past four years as a general partner at venture capital firm Benchmark, after previously serving in the same role with Greylock Partners and as the first-ever product manager at Pinterest. In this episode Shane and Sarah how studying philosophy helped in her career as a venture capitalist, the value of intellectual rigor, her concept of the net-present value of pain, why every strength has a corresponding weakness, where executive boards go wrong, assessing the performance of a CEO, lessons of rapidly scaling at Pinterest, and so much more. -- Want even more? Members get early access, hand-edited transcripts, member-only episodes, and so much more. Learn more here: https://fs.blog/membership/   Every Sunday our Brain Food newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/   Follow Shane on Twitter at: https://twitter.com/ShaneAParrish Learn more about your ad choices. Visit megaphone.fm/adchoices

I'll describe what you see for the people who do scale. The founders who are not afraid to be vulnerable, they understand that they are works in progress, and then figure out the ways to constantly grow, evolve, and push their own abilities. And it's the people who aren't willing to admit to themselves or whomever they work that they don't know something or they're not letting themselves have that learning moment

of accepting that they don't know something. something, that they tend to just hold themselves back and not scale as a company scales. Welcome to the Knowledge Project. I'm your host, Shane Parrish. This podcast sharpens your mind by helping you master the best what other people have already figured out. If you're listening to this, you're not currently a sporting member. If you'd like special episodes, access before everyone else, transcripts, and other member-only content, you can join at fs.blog slash podcast. Check out the show notes for a link.

My guest on this episode is Sarah Tavill. Sarah's a general partner at Benchmark. This conversation is interesting because not only is Sarah an investor, but she has significant operating experience in scaling as an early employee at Pinterest. We talk about how studying philosophy helped her as a VC, her concept of the net present value of pain and how it applies, why every strength has a corresponding weakness, where boards go wrong, assessing the performance of a CEO, lessons from rapidly scaling Pinterest, and so much more. It's time to listen and learn.

You studied philosophy and not computer science or business. How is that shaped the way that you approach your job as a VC? Yeah, you know, it's funny. Like, I think most people misunderstand what philosophy is. I think that people probably, when you say that you studied philosophy, they imagine a bunch of, you know, guys in three-piece suits, sitting around a table, drinking cognac and pontificating on the meaning of life. but it is a little different.

You know, of course, philosophy is this big umbrella, but the type of philosophy that I studied in college was a very analytical version of philosophy where, you know, it's underpinned by logic. And you learn a level of intellectual rigor that you don't even realize, it's kind of like you think you can be rigorous and you're thinking,

and then you have to write a philosophy, or read a philosophy essay where you have to, you know, you're, you're breaking things down into premises, you have to think through thought experiments to imagine all the corner cases and preempt like any objections that someone might have on your argument. And the level of rigor that you learn actually has made such a difference in my life. Like when I was doing product, a Pinterest, you know, a product document where you're making a recommendation on a product is actually very similar to, a philosophy proof. Like you have hypotheses, you know, about how users behave, how they'll accept

a different, you know, a new feature, what, you know, what their, what their intent is on the product. And you, you underwrite that with, you know, user research, experiments, analyzing the data that you already have. And it's, you know, if all these hypotheses are true, then the conclusion is that you should ship the product. And that's, it's a philosophy proof, but for product. And I think investing is the same thing. Like when you're writing an investment recommendation or thinking about a potential investment, you also, you know, really what it comes down to is a proof in the same way where you have the premises, which may be a belief that you have about the future, the kind of product market fit, the founder market fit, all these things that you once again underwrite

by, you know, understanding the competitive landscape, talking to customers, looking at the data, all those things and trends. And if you believe all those hypotheses to be true, all those premises, then it follows that you should make the investment. And so it was one of those things that I never would have anticipated, you know, when I studied philosophy, it wasn't with intent to go into venture by any way or to go into technology even, but if it ended up being an incredible place to learn how to be good at this job.

Speaking of Pinterest, you led some acquisitions while you were there. What was that process like? can you walk me through sort of like the end to end all the way from identifying the acquisitions to integrating the cultures? Yeah, you know, well, the acquisitions that I worked on, it was super early in Pinterest time. I think I did three kind of the first acquisitions that we made there. And so they were primarily with one exception, more just the talent. I have a hypothesis that I believe that founders are just a unique type of person. You know, they are, it's part of why I love to do what I do.

It's, I think that it's just such a different DNA of person. And what tends to happen in a company and a startup, or, you know, a company like Pinterest that's going through hypergrowth is that you're constantly recruiting. And you have a recruiting team and the recruiting team is doing everything they can to find the Google engineer, the Facebook engineer, the Twitter person, whoever it may be, and to have them come into the company. But it's all the same type of DNA. It's the type of person who joins a company at a stage where it's more secure, where you have a more specific role.

You know, you're looking for a little bit more certainty and structure versus the person who's a founder. Like they, you know, risk-loving, responsibility-seeking, it's not about what my job is. It's about what the company needs, you know, action-oriented, high degree of urgency. And so I think it's so important to constantly inject that type of DNA into a company through the entire life cycle of a company. I'm a huge believer actually in talent acquisitions for this reason because it's just very, very difficult to recruit founders because they're leading their companies. And so the idea with the talent acquisitions was let's find this type of DNA. Let's bring it into the company, particularly in, you know, types of strengths that we needed. For example, one of the acquisitions that I was most proud of was this visual search company.

They had developed some computer vision technology, and that was something that Pinterest needed. We had no computer vision DNA, and bringing in that type of kind of founder orientation, it was incredibly impactful for the company. What are some of the lessons you learned about scaling Pinterest that apply outside of Pinterest after you left? Oh, gosh, Shane, there's so many. You know, the first thing, and this is one of the things that the founders with whom I work hear me talk about all the time is that kind of what you measure matters. So, you know, I remember at Pinterest at one point, our growth team decided that the metric that they were going to base their success on, their OKR on, was monthly active users,

you know, so this lowest common denominator thing. If someone, a user comes to your product once in the month, they, count as an MAU. And OKR is objective and key results. It's just a way for a company to have a team say, this is our main objective for a quarter as an example. And the key results are the key projects that will move the metric on that objective. And what happens is that if you choose the wrong metric, so in maus in this case, you actually end up optimizing for the wrong thing. You know, the product that you build, like you end up deciding on different features that you're going to build that optimize for something that's on top of the funnel base as an example here. All startups are incredibly resource constrained, right?

Like there's even despite that there being so much capital of chasing startups, at the end of the day, you're still a capital constrained environment where as a founder you have to make sure that you're allocating your dollars in the way that will generate the most equity value for the company long term. And you just waste a lot of effort. It's a shame, really, when you're focused on the wrong things. When the growth team realized this and ended up changing their OKR to be what we called weekly active pinners, you know, actually making someone who signs up for Pinterest not just come to the site once in a month, but actually pin something once in a week, their entire roadmap changed. And we were able to make the users that were signing up far more successful and happier

and better long-term engaged users. So what you measure matters is huge. And I have an allergy for vanity metrics. I can see a vanity metric a mile away. And it's one of those things that I just think it's, you know, it's back to that intellectual rigor of really being honest with yourself, of what you're measuring and is it really the right long-term thing. Org chart matters too.

Like, I think people sometimes see org changes as, as a bug, you know, as a, uh-oh, something must not be going right with my company, the company that I'm at because we had to change the org chart and now I'm reporting to someone else or, you know, they had to change these leadership teams. But it's actually a sign that the company is growing. And sometimes I think of it as like setting a bone. Like you have to, like as you're growing, you have to be able to set things in the right way so that the company is set up to be successful, to grow quickly, to have the org chart, the org chart actually be aligned with the strategy. And so it's just another one of those things where so many times I would see

situations where the way that the organization was structured actually created a tax on our ability to execute. Td Bank knows that running a small business is a journey, from startup to growing and managing your business. That's why they have a dedicated small business advice hub on their website to provide tips and insights on business banking to entrepreneurs, no matter the stage of business you're in, visit TD.com slash small business advice to find out more or to match with a TD small business banking account manager. Hey, double click on that. So one example I'd give, the growth team wasn't reporting to the product team, to the product

leader. And so there was a point in time when the growth team at Pinterest was actually reporting to the marketing team. And so you had a team that was separate from the product team that was making changes to the product and wasn't actually aligned with what the product strategy was going to be, what the priority features were for the product team. And it meant because we were all making changes to the same products, we had to have a lot of meetings to coordinate. You know, there was no single leader who was the one who was, you know, making sure that everybody's strategy and tactics were aligned. And so it got a push down to the rest of the team, a lot of overhead, a lot of

meetings, a lot of people with different incentives pointing in different directions, and it slowed everything down. And so when the org changed so that the growth team reported to the head of product, everything just got streamlined and more aligned, and we all executed a lot better. Talk to me a little bit about some of the considerations of integrating founders into an existing culture because that sounds like it's really good or really bad. Like, can you have a team of founders? How does that work? It's a good question.

I think you'd be lucky to have a team of founders. All people that work in a company are on a spectrum. On one side, you have the founders where their identity is the company. They don't ask what their job is. They ask what the company needs. They work nights and weekends. It's like it's an all in pursuit versus on the other side of the spectrum, you know, to be as, you know, almost as hyperbolic as possible. It's like the mercenary, the person who will just go wherever they're paid the most.

And when you find those people who are super impactful on the founder's side of the spectrum, what is really important is that their identity, they want their identity. identity to be the company. And so you have to make sure that they're really, really aligned with the mission of what you're doing because then they're going to go all in on it. But if it's just grafting someone on because they want a soft landing for their company, but they don't really care about what your company is doing, then that feels like it's not a path for success. I'm curious, from the outside, looking in a lot of these tech companies, especially ones that have gone public recently, don't seem to generate any.

cash for their shareholders. In fact, they consume cash for their shareholders. How do you think about this? How do you feel this plays out? Like, what are your thoughts on this? Because you have a very different vantage point than I do from the outside looking in. You're the inside looking out. There's kind of two things that I think about there, Shane. The first is that there's a cash flow thing that you have to look at, which is it may be that up front you have to invest money in marketing and sales, whatever it may be, in order to sign a customer that will become very, very profitable for you over a longer period of time. And so even though there's burn up front that you have to accept over a longer period of time, it's a profit-making machine. It's a machine

that you can put a dollar in and get five, $10, whatever it may be back. And when you have that type of machine, you want to be as aggressive as you can at growing. because it's going to be a positive IRR for you. And it leads to the second point, which is that, you know, something that I think a lot about and in the companies that I look to invest in is companies that can escape competition. You know, the companies that escape competition ultimately are the ones that get to a place where they're incredibly profitable. They generate a lot of cash for their shareholders.

They are able to create great experiences for their customers. But you're not going to be able to escape competition overnight. There's going to be a lot of investing that you have to do in sales and product, in the engineering side. And more and more you have competition. And they're going to be doing the same thing. They're going to be investing heavily. And if you have a more efficient machine where you're able to, again, take that dollar

and make $5, $6, whatever it may be out of it, if not more, then you should be burning as much money as you can't. do efficiently to keep getting further and further and further away from the number two in the market. And so it's a very rational thing to do, assuming that you have that machine that I described. There's a lot of people who think that they will have that machine. I know that there's a little bit of, you know, believe me, that can happen where you don't quite see the contribution margin and someone might think, oh, if we get to enough scale, then the economics will start to work.

tend to be trickier. And there's a lot that you have to believe in terms of how the competition's going to spend money, whether the economies of scale or network effects that they describe will actually come true. And those are trickier. How do you? Let's dive in there just a little bit because I'm curious how you determine the companies that are sort of using money to grow with this sort of like pain today, again tomorrow versus companies that are using money to acquire customers but don't actually have a viable product. They're giving it away for free or the incentives are just so huge that customers are signing up for it, but they can't quite figure out that there is no runway there. How do you think about that? Or am I thinking about that wrong? So number one is that

you're looking for early evidence that what the founder believes will be true, which is that the contribution margins will expand over time or that the cost to acquire a new user will go down or whatever it may be so that you can get to a place of profitability on a customer level, you're looking for evidence that that actually is starting to happen, that it's getting better, that you can see, you can extrapolate from the points that you do have, that there is a path there. The second thing is really just the founders understanding numeracy of their business. You know, there's a very big difference.

between a founder who may, you know, they wave a little bit that this is the way it's going to be and then actually seeing the reality of the numbers and they're not being a great connection between what the founder understands of their business and the facts, the brutal facts on the ground. And by the way, that kind of really facing the brutal facts, I think that's a Jim Collins concept that I love is so, so important. And then there's the founder I remember this with Francis, the CEO of Sonder, a company I invested in, that he just knew every number in his business, like cold, and he knew exactly how he was going to make them better over time. And there was just a little bit of this feeling that here is a founder who is just

a freaking animal, and they're going to keep on going up this curve, and you can extrapolate from where they are that they're going to make it happen. What are the things that you see yourself saying over and over again across the different boards that you're on? So one of the things, one of the first things I say is this kind of concept I call the net present value of pain, which is, you know, when you're running a company, there's so many decisions all the time that you need to be making and so many optimizations. And a lot of times, there are some decisions that you kind of want to procrastinate on, you know, it may be a decision to cut a product that you had loved and you don't pursue more often than not, it's people things, you know, someone who's not scaling in their role and has to be leveled or let go. And what I always remind founders is that pain today postponed until tomorrow is

going to be harder. It's like taking a loan out on the pain. And particularly in the early stages of a company, if you have the wrong head of product and you know it, but you're like, hey, I'm just going to wait a few more months until I get this other role right before I address this thing, the compounding problems that happen, that you ship the wrong things, you hire the wrong people, like the problem, you have to nip these things in the bud, otherwise there's these cascading effects that happen that make it a bigger and bigger deal when you actually get to that decision. Another thing I always remind people of is something I learned from my partner at Greylock, Reed Hoffman, which is that every strength has a corresponding weakness. You know,

it's one of these things where I think a lot of times, you know, people in a company, one of the examples I always give is the difference in an org structure, as we talked about before, between an org structure that's more centralized, you know, where there's more of a command and control, everybody is moving to the beat of the same drum versus a decentralized org where you have more autonomy at the edges of an organization. They can move quickly. It works a lot for companies that have more local businesses like an Uber. But there's a corresponding weakness to both of those types of organizations. For the decentralized org, what tends to happen is people aren't coordinated and they end up building some of the same things

or potentially have conflicting things. Every team is building the same marketing acquisition engine where if you brought that centralized and maybe you'd have some economies of scale. And on the centralized thing, it can feel like there's no redundancy in the things that people are working on, but it's slower. And what sometimes happens in a company

is that employees, and I remember this at Pinterest, feel this the weaknesses of the approach instead of the strengths you might not realize you take for granted that the decentralized org is helping the company move really quickly and and and like have very time as teams that are very focused on the local situation but instead what you feel as an employee is the chaos of oh my god we're all building the same thing that's slightly different like isn't that a waste of resources and and so it's it's it's how helping people take perspective that the strength of an approach has a weakness that you can't separate. I think it's also, you know, when we think about ourselves as people, you know,

I used to always think, oh, God, I can't remember people's names. You know, I'm like really bad at trivia and remembering facts. And then I realize that actually, Myers-Brigg helped me realize this that it's, you know, I'm not an S, I'm an N. You know, like the, and is the abstract thinker. Like, that's my strength. I'm an abstract thinker. And the strength of being an abstract thinker comes with the corresponding weakness

that I'm terrible at people's names and you'd never want me on their trivia team. And for founders, they have these things all the time where the founder who is incredibly operational and like just, you know, a machine in terms of executing may not be the most strategic person and the other way around. And so it's always, you know,

accepting and realizing these two things come hand in hand. And then as a founder, just surround yourself with people who have the strength that you don't, and you're going to have a great team. One of the things I want to come back to that you said was sort of identifying people that can't scale in their role. What are the early warning signs that people aren't scaling in their role, that there's problems on the horizon, that action is necessary? I'll describe what you see for the people who do scale. which is they're just learning machines, you know, it's such a growth mindset thing where

everybody has different ways of learning. Like I have, one of my founders is a PhD, and he's someone who his way of learning and pushing his horizons and what he's able to do is to read, is to study, is to kind of, you know, he's a learning machine from whatever he can consume in terms of content. Some people, you know, their way of learning and pushing their own envelope is to surround themselves with CEOs that are a step ahead of them and find great mentors who push them and hold them accountable. Some people might, you know, find coaches, you know, that actually help them through that. But the founders who I see, the founders and leaders are not afraid to be vulnerable, like that they understand that they are works in progress.

and then figure out the ways to constantly, constantly grow, evolve and push their own abilities. And it's the people who, I think, aren't willing to admit to themselves or whomever they work that they don't know something or they're not letting themselves have that learning moment of accepting that they don't know something, that they tend to just hold themselves back and not scale as a company scales. A couple of podcasts ago, I was talking with Chris Cordell, who is the chief of staff to Stewart Butterfield at Slack. And she mentioned something, and I'd love to hear your opinion on this, where when you identified somebody who didn't fit the role, she said, just let them go. Don't transfer them internally. Don't give them another job. What's your reaction to that?

I would say that's right, 95% of the time. Like all rules, sometimes you should break it. particularly, you know, at the early, early stages of a company when you're going through hypergrowth, you're bringing in these athletes. And the company gets more specialized over time. And so roles have to evolve. But I absolutely agree, you know, the 95% scenario, there is a non-confrontational weakness to this kind of transfer, which is that you're telling someone, hey, not that I don't think that you're scaling with the company, but hey, let's find another role for you in the company and you can become someone else's problem or, you know, it's one of my partners, Eric Visria, has told me this framework that he had at LoudCloud

when they were hiring, which was that they would interview people and they would rate someone on a scale of 1 to 10. And you had to be an 8, 9, or 10 average in order to be hired. And the thesis was that sevens kill companies. And what that means is that, you know, when someone is a four, you just know they're not doing the job, they're not up for it, and let's take them out of the system. But the problem with the seven is that you don't get to that point, because that person will have glimmers of being able to do the job. Maybe they'll be super cultural carriers. They'll have these things that are redeeming. But because they have those things, two things happens. One, there's an opportunity cost of that seat, of course. Like when someone

that's a seven is holding the seat, it means that you don't have a nine having that seat. And two is that, and I see this all the time, is that the execution of a team is often brought down by the weakest link. And so an entire team can be brought down by that seven. And so kind of back to that point of transferring someone, if they were a seven or worse for that, role, you know, the probability that they're going to be a nine somewhere else, like you have to really be, you have to have real conviction that that's going to be true. Otherwise, the most likely thing that you're doing is trying to avoid a hard conversation that you just have to have. So you're avoiding the brutal facts. I like that that's sevens. Sevens kill companies. And

if you think of that, it's almost multiplicative, right? So the difference between a seven and a nine is huge. If you think of it instead of addition, you think of it as multiplying the people that they work with. Yeah, absolutely. And especially when they're hiring people. Because, you know, it's kind of that classic, A's higher A's, you know, B's higher C's. Like it's just the, when you're a nine, you're going to, people who are eights, nines, and tens want to work with that person. But the seven is just not going to bring that same level of team to the table. And so it does. And so it does, does create this cascading challenge in an organization that you just have to be hyper vigilant about.

I want to come back a little bit at a higher level to the role of boards. Where do you think boards go wrong with startups with all companies? Oh, how much time do we have? One of the things that I always tell founders is you have to make sure that the board members that you bring on are as much on the same side of the table as you about the future, like where the company is headed and the future of the company. Because, you know, people, whomever you have around the table in the boardroom, even an observer, you know, I think people kind of think of it as, oh, board of director, like this person's on the board and this one's an observer, so the observer

doesn't matter. That's so, so wrong because things rarely come to a vote. It's always about what's that conversation around the table. And someone who has a seat at the table is participating in whatever strategic conversation you're having can really change the direction of a company. And so you want to make sure that the judgment of the people that you bring around the table is like super high and that they're going to push you in the ways that you need to be pushed and want to be pushed and that they're aligned on the vision and the mission of the company. Otherwise, it just creates another tax on your execution where you end up having to spend

time convincing someone who maybe was never on board with the direction of the company that you're going in. And so one is just like finding those people who aren't cheerleaders, like will help, we'll show you the brutal facts, but at the same time are all marching in the same direction. That's number one. Number two is, you know, and I've seen this, is kind of the micromanagement that can sometimes happen. And this is sometimes the weaknesses that X operators have when they transition into investing is thinking, oh, I can do this, and I'm going to dig in the company and get, you know, help them with growth or help them whatever it may be. And it ends up acting as a crutch to the CEO. And so instead of the CEO hiring the person that they should

hire, so they have that inside the company, you know, like working on a 24-7, you have this person who thinks that they're really good at whatever functional level, whatever function it is, coming in and really causing more pain where then the CEO feels like they have to have this person who's not living and breathing the company every day, you know, opining on different product directions or, you know, what the compensation is going to be for the sales team. Like that's not productive. And then I'd say the third thing is just when there's distrust that happens with a, the board and the founder, then you can't have the conversations that are important. You can't have the, you can't hold the mirror up to the founder because they don't want to

hear it and you're not going to be, you're probably not having good intent if you're, if there's a trust breakdown already that's happened. Sometimes founders describe a board that can get toxic and it tends to be in that circumstance where there's just a trust breakdown and the board isn't able to perform the duty that it has, which is to, there's the kind of fiduciary duty, of course, but then there's, I think, the more important stuff, which is, are we focusing on the right things? Are we pursuing a strategy that will lead to, you know, tremendous equity, value creation, all those things. Talk to me a little bit about how that trust breaks down and what it looks like when it's happening. You know, one of the things that I've tell my companies is you can,

take as long to you can wait until the board meeting to give good you know good news but you give bad news as fast as possible and there's that is a classic trust breakdown from the founder to the board where the board feels like hey why are we just finding out about this now what else don't i know and so that's that's an easy way for things to break down the other way that happens from where the board loses the CEO's trust is usually if the CEO doesn't feel like the board member is acting in the best interest of the company. If an investor ends up investing in a competitive company, if they recruit someone to a different company, if they end up just optimizing for their own equity in the company instead of

like helping make a financing successful, all those things can break down because ultimately when you're the CEO, you want to bring on a board member who is going to be doing everything they can to make the company successful. That should be their optimization function. And when there's a breakdown there, that can really hurt trust. You strike me as a very structured thinker, process-oriented person when it comes to making decisions. Can you peel back the curtain there a little bit and walk us through maybe your personal process for making decisions, whether it's to invest in a company or even at a board level? How are you structuring those things in your mind. Yeah, you know, I think it's it's kind of the way my brain is. And it's why,

you know, one of the things that I try to do a lot is synthesize the world in a way and reduce it so that I can have a framework from which to reason. You know, it is this kind of building patterns so that you can see the topology of the world in a way that is higher resolution then if you didn't have some of those mental models from which to reason. And so for me, like, you know, I asked myself, like, I meet with a lot of social products all the time, and you can see them growing really quickly. And one of the first frameworks that I actually wrote about to help me figure out which are the ones we should invest in is this thing I wrote called the hierarchy of engagement, which is how do I know if something's growing really quickly,

if it's actually going to be something that endures. For marketplaces, like, you know, I see a lot of companies. There's so many founders who orient themselves towards hitting this $1 million of annualized GMV. You know, there's kind of these ideas that go around, which is that to raise your Series A, you have to hit a certain metric. There are ways to hit milestones that are more vanity metric than the actual kind of authentic, real intellectual rigor around kind of, am I really doing the hard work to get to this milestone? And so it was a similar thing of like, how do I look at these companies

and understand, are they orienting in the right way to build enduring value? And then as a board member, then how do I also help kind of pull the future into the present and help align the strategy with a way that I think will create maximum value? So I'm, I'm, always trying to put structure around decision, help me think through something in a way that I hope gives me an edge in making the right decision at the time. Well, just like Michael Jordan, we can get some insight into that, but nobody's going to listen to this and become Michael Jordan. So maybe you can go into some more detail on sort of what are the mental models that, what are some other mental models that you're thinking about or frameworks that you're using

when you're sort of internally structuring your decision. I imagine opportunity cost is one of them. But what else keeps coming up over and over again? What are the timeless ones? Well, opportunity cost is such a huge one. You know, at Benchmark, our model of investing is that we have decided that we're not going to scale our business. You know, we haven't grown our fund size. And it's just five general partners right now.

And it's kind of this rare structure of an equal partnership. And we don't delegate any part of our job. Kind of our aspiration for any company that we are on the board of is that we are the hardest working, most impactful board member that you have around the table. And so there's no talent partner to whom I can delegate a search for. There's no associate who's going to dig in on your model for me. there's no marketing person who's going to help you think through PR.

It's you got me and the rest of my partnership. And so it means that when you take a board seat, the level of commitment that kind of promise you are making to the founder is I really think at a very different level than other people. I'm on seven boards right now and I am on these talent calls every week for in my companies where we're doing a search for a CRO as an example. And it will always be me and then the talent partners of the other firms as opposed to the partner itself. And it's just a very different level of service. And I think when it's me on the call, helping kind of figure out the right profile person to go after, interviewing people, closing them, that we're going

to have a better outcome. But it does mean that that opportunity cost, The commitment you're making is a very big commitment. And so it's always when you make an investment, not just are we gonna make money, but of all the places where I can spend my time, is this the place I should spend it? This idea I described before of escaping competition, you know, that is something that is fundamental

to all the companies that I invest in. Is this a company that is always gonna be fighting tooth and nail with another collective of companies for an incremental point of market share? Or is this a company that can really dominate a market become just so much better than any substitute that they become the de facto standard in the space? How do you think about that?

Because what you're really trying to do is, like, what we know from history is the only thing that gets us out of sort of trench warfare is asymmetry and weaponry, right? So how are you dictating, like, how are you determining escaping this competition? so that you have an asymmetric outcome where maybe there's one or two players and they play nicely, maybe it's a winner take-all market, or how do you work through that? Yeah, there are different flavors of working through it. So the strongest, strongest sign is a network effect. And that's why I spend a huge amount of my time looking at social companies or our marketplaces

because they both have network effects. And you just have a dynamic with those companies where if they're able to get their flywheel spinning fast enough, they're able to tip a market. And once you tip a market, the space between you and the competition just gets wider and wider. The other type of company that doesn't necessarily have a network effect,

but I also love, are companies that, actually go after a space that is underestimated from the outside. And because it's underestimated, it actually doesn't invite competition. So, or the competition isn't strong competition. So, you know, I'm on the board of a company called Chainalysis. And chain alias is, it's in the kind of blockchain crypto space where they have built a technology that lets law enforcement agencies, government agencies investigate transactions on any of the current blockchains, the Bitcoin blockchain, Ethereum, et cetera, and make sure that there's no illicit activity. And then the companies that are regulated and want to participate in this cryptocurrency

ecosystem, but have to make sure that they're not in the middle of some money laundering. They need a tool, and so they use chain analysis. And so chain analysis has become this de facto standard in the space. It just got into a space before other people saw the opportunity. And because they were the leader, they were able to build more and more technology. You know, they're able to go across any blockchain now, where as they got bigger, they got amortized the cost of their engineering efforts across a broader and broader revenue base, which let them reinvest in the business and pull further.

and further away from any competition. And so now, you know, it's kind of a, that's one of those winner-take-most dynamics without a explicit network effect, because they were there first, they executed really, really well, and just got so much bigger than any of the competition that they could keep on making their advantage bigger and bigger. I like these smaller sort of niche ideas, too, where it's a smaller market and maybe you're an A player and you go into a B market and you can just dominate that B market. And then I'm curious as to where these things start to go wrong. So VC is, you know, starting a business is necessarily valuable in and of itself.

And so there's an expected sort of failure rate. And then there's things that you do that maybe increase the odds of that failure rate. So across your aperture, all the companies you have exposure to, all the companies in the benchmark portfolio, all the companies that you get pitched. What are the mistakes you see CEOs making over and over again that increase the odds that they're not going to be a success? The thing that chain analysis got right, you called it a B market. I'll change that. Oh, yeah, I wasn't trying to be derogatory or anything. But I think there's a nuance here that's really important, which is that it actually is a B market in the beginning. It's really small. No one cared about it. That's why

there is no competition. The important thing is, you know, markets are like rivers, you know, where you want to be, you're like a canoe on the river. And if there's a great current for you, it's going to keep pushing you. And so it might be that the market is small, but the current is increasing. And it's getting bigger and bigger and bigger. And that's going to help you build something really, really valuable. We have another company called Benchling that has just done a phenomenal job executing in this kind of biologic space, which again, there was a current that they saw that other people didn't see that was creating this really, really big market. But in the beginning, someone else might have thought it was a B market. For the failure scenarios,

a founder's ambition blinds them in not picking a small starting place to really, really execute and get incredibly strong product market fit. Their ambition blinds them to wanting to take on a really big problem with a blunt product that tries to be a little bit everything for everyone versus accepting something that might feel small in the beginning but opens up into something much bigger. I love the way that we're talking about this because we're really at the heart of it, I mean, we're using a little bit of different vocabulary,

but we're really talking about mental models. When you're on the call doing this talent scouting, you're touching the territory. When you're not delegating that work, nobody's giving you a map on the other side of it. You're in the weeds. You get to know what's going on. When you're talking about sort of the B market, for lack of a better term, it's really contrast, right? You want to be the best player in a market with weaker competition. And so you're talking about how do we generate the most contrast?

Because there's a lot of value to be created in that contrast. Whatever market you're in, whether you're in the A market, you can be the A plus person. but you really want to be the A-plus person in sort of a market without a competition. You know, I think about these two companies, DoorDash and Postmates, a lot. You know, it's such a beautiful case study in a way because Postmates was recently acquired by Uber, incredible team, and they were the first actually to realize that there was an opportunity for them as this kind of on-demand player to interpret. introduce delivery for any small business.

So it had been that before you had Grubhub, which was Grubhub and Seamless, were the two innovators, incumbents in the space, that realized that they could create a marketplace where they would get restaurants that had their own delivery to list on their marketplace, and then they would help those restaurants get more demand side for their delivery. And what Postmates realized is that if you just live, limit the supply side to restaurants that have their own delivery, that's actually constraining the market beyond what is possible. And so Postmates realize, hey, we'll provide, we'll create a third side to this marketplace, which is the delivery on-demand side, and we'll let any business,

you know, restaurants, cafes, retailers, will provide delivery for them so that we dramatically expand the supply side, and that creates a much stronger value proposition for the demand side, which is true. DoorDash had the same insight, but followed them kind of a year and a half later, so maybe inspired by Postmates. And they both use incredibly similar techniques in the beginning to get the demand side flywheel spinning. But the difference was, is that Postmates went after San Francisco. There was already competition there. You know, I always think, that you have to be just so much better than the competition, that it's obvious that you're the way to go.

But that wasn't as obvious for Postmates when they were going into this big city because the incumbents weren't necessarily like doing the same playbook, but they had a pretty good product that they were offering. DoorDash on the other side went after the suburbs. You know, they went after a market where everybody else thought it was,

terrible and not, you know, economic to provide delivery in the suburbs. And so they went to this desert for food delivery. That almost sounds like Walmart-esque, right? Yes, yes, yeah. And so they went after this market where everybody else had, you know, is a desert. People were like, oh my God, you're providing delivery. Like that's this new thing. And it also was a lot easier for DoorDash to get to a very, very big percentage of the market in the suburbs, because again, the restaurants weren't being attacked by 50 different vendors trying to get their attention. DoorDash was probably the only one knocking on their door. And there aren't that many restaurants in the suburbs relative to a city. Yeah. You know, I would say Postmates could

be executing a 10x DoorDash's execution, but because DoorDash had a strategy that let them just be, you know, so much better than any substitute, because it's a lot better. to be better. It's a lot easier to be better than the competition when you have no competition. Your competition's really crappy. And so it just got them to be able to be in the zone where they could tip a market before Postmates did. And I kind of describe it as like Postmates, I think, optimized for GMV for maximizing GMV. And they try to boil an ocean. Whereas DoorDash really optimized for tipping this market, what I think of as like happiness. And they boiled a, thimble. And you can see, I mean, I don't know, I haven't checked DoorDash's market cap recently,

but it is an astoundingly successful company with a very, very different strategy in the incumbents. Do you think that there's something to the notion there that if you can figure out your business in the hardest conditions, then the easier conditions, which would be the city, are going to be much easier. If you can make it work in the suburbs where there's, you know, deliveries are more complicated. Signing up people might be easier, but the whole network and the operations are going to be a lot more complicated, then that translates into it working in the city, whereas in this case, working in the city might not translate to working into the suburbs, or am I thinking about this wrong? No, that's absolutely true. I mean, you see that in so many different industries.

I remember I was lucky to observe the board of diapers.com. And those guys started by selling diapers, wife's, and formula. It's like a 2% gross margin business. But if you can get really good at making the economics work for a business that has that level of gross margin, and then you start to add more, you know, higher gross margin products to the basket, the DNA of the company, the habits of the company get forged in this really, really resource-constrained environment that only creates benefits from there. That said, I wouldn't say that you should choose a market necessarily to pick the hard thing. I actually think that you want to pick something that is easy to win, to tip the market.

You know, and there was ways in which going after the suburbs was harder than going, like, operationally harder, harder probably from a economic perspective, although I'm not positive, than like going after the city. but it was ultimately easier to get to that tipping point. And that's what I think you really want to maximize for. Do you think that there is an interesting notion. We just talked about sort of margin and increasing margin over time. Do you think there's an interesting way that are there businesses that go after, you know, Amazon would be an example, I think, where they have a low margin and then they lower it over time.

And that's how they get bigger and bigger and bigger and bigger. And then you can't really compete with them if they're constantly lowering margin, and at least playing that game, how do you think about that? Back to the concept I articulated before of tipping a market. One of the wonderful things that happens when you tip a market is that your organic growth starts to explode. You know, because your value proposition relative to any other substitute becomes just so much better that you would be stupid as a buyer not to go.

You know, it's almost an IQ test. Where are you going to buy from? And so what the beauty is of, you know, a company like Amazon that's able to articulate a flywheel very clearly is that they don't have to spend money on the acquisition side. And they have, of course, because they have so much more inventory that they can make their margin off of a very, very, every skew that you could possibly want versus any individual product. And it's just, I mean, how do you compete with that a flywheel that's spinning at that magnet? It's, it's, you end up, you know, it's just a very, very difficult thing as we, as we've seen over the last 10 years. So, so where does this go wrong?

How does this, like, these business model, I mean, ideally, I'm probably, Amazon's not going to be the champion in a century from now, but they have a really good model, and the model has this runway that's incredibly long. Does that go wrong through complacency? Does it go wrong through greed? Does it go wrong through bringing the future into the present? and sort of like increasing the margins. How do you think about that?

I think the number one thing that I see is complacency, although from what I can tell, Amazon is not a complacent company by any means. But certainly there are plenty of examples of companies that got leapfrog, that got disrupted in some way by a new company. I'll give eBay as an example. I mean, eBay, which, you know, Benchmark was lucky to be the early investor, and so it's been, you know, just a phenomenal company. And yet at the same time, you can't help but see that that company is being unbundled by new startups, that, you know, there are vulnerabilities. The hard thing about being a horizontal platform like an eBay is that you have to try to be everything for everyone, you know.

And what that forces is this kind of lowest common denominator product. Whereas, you know, I take Goat as an example here where Goat was a company. I don't know if you're a sneakerhead. No. It's a, it's a marketplace for sneakers, secondhand sneakers and now new sneakers. If there's that pair of Yeezys, you've been eyeing, you can go there, Shane, and get them. Definitely. And the experience, you know, the company started what I, you know, the,

the foreclore, at least, is that the company started because the founder had been working on another startup. It was, you know, running on fumes, looking for a new idea. And he had ordered a pair of sneakers on eBay, you know, Jordans or something, opened the box. And it was a pair of counterfeit sneakers. It was, you know, they were not authentic sneakers. And that was the light bulb for him that there was this vulnerability to this huge, huge marketplace that had hundreds of thousands of skews for Nike sneakers, but it was that people didn't know, had to do a lot of work in order to make sure that they weren't going to get counterfeits. And that, and they didn't always trust that if they were going to buy something, that it would be authentic. And so Goat went

after that vulnerability, first by creating like, you know, a policy that it was always always good that they were going to vet all the inventory to make sure it was authentic. And then they also created a product that was focused on this white hot center of the sneaker vertical that was mobile first and had features that eBay just couldn't build because the eBay wasn't for just sneakers that let them disrupt eBay and leapfrog what they were doing. And so there's there's kind of this, what's that saying that there's only two ways to make money, bundling and unbundling. The creative destruction that is, you know, part of what we love about startups. And certainly, I think that any big horizontal platform, while they have this

incredible strength, which is their scale, there's also a vulnerability there that we might, you know, see evolve. Well, what's the most interesting thing that you've seen, or a most surprising thing that you've seen recently in terms of startups? Well, you know, the, The thing that has just been so fascinating over this past year is, you know, is kind of the effect of shelter in place. It is transformative in so many different ways. You know, there's a class of companies where the future has been pulled forward, you know, or things that would have been on that three to five year roadmap become on the, like, we need to do it now roadmap, you know, the kind of like and there's you see that in the in the success of a lot of these software businesses right now

and it's you know we've seen the benefit of that and it's and it's it's just transformative and then of course there's this change to the way we work where we had always you know the default answer had always been we're going to have an office and we're all going to be co-located and we're going to go into a room together and we're going to you know get through that you know roadmap planning together and like that's the way we're going to work. That was the default. And now, of course, everything's changed. You know, we are, we are in a place where the default has been completely changed to the mirror image. And we're having to make decisions now, all these companies of will the new default that we have now persist post-shelter in place? Or does it revert back?

Right. And what, and like, you kind of feel that it's not, it's not going to go to the way things were. Like there are, you know, we've seen an acceleration in the technologies that we have now to make it so that when you're working remotely, it can actually be better, more productive than it used to be when we were in the same place. And in a way, like you had technologies like Slack and Zoom that I think facilitated a new way of working, which was the ability for us to be remote, but aren't actually native to the way we are working when you're working remote. And so you're seeing a new generation of companies that are native to this either fully remote or, you know, future hybrid work spaces that I think are going to be transformative for the way

that we work with each other and collaborate across functions. So that I think is incredibly exciting. And then there's also the consumer world, which is, you know, Right now, you're just seeing, you know, if it had been for the last three years, this, you know, it always felt, rather not the last three years, you know, pre-COVID, that consumer was just, it was owned. It was owned by Facebook and Amazon and Google and Apple. And, you know, and if you wanted to build a consumer company, you were pushing against a rope.

Right now, because of shelter in place, people can't spend time. time in the real world. All these ways that we used to spend our time are no longer available to us. And so because of that, it has created this new gold rush or a land grab, really, for all these minutes that used to belong to offline minutes are now suddenly fair game for all these digital products, mobile products. And it's created this, you know, wonderful new renaissance for these consumer social companies. And so that has been really interesting to see. And then, of course, the question is what persists, what thrives once, you know, you and I are able to be in a conference room together or give a friend a hug. Yeah, that's a really interesting question because it's like

the longer it goes, the more your habits will probably change. They're probably not going to change fully to where they are now, but you're probably going to get more takeout than sitting at a restaurant. You're just used to, I mean, that you develop that pattern of behavior. And It really is huge. And it's, you know, I, like the longer that we are in this suspended state, the stronger these new habits will be. And, you know, you, of course, there's the, they're good and the bad. There's the good, which is how people are collaborating with each other and connecting in this kind of global maxima states where the geography becomes, you know, not as important. then, you know, just being able to connect somehow. And then there's the bad, which is that, you know, I do think I'm, I didn't, I never knew

if I was an extrovert or an introvert. And now I know I'm an extrovert. Like, I think people, you know, miss each other and should spend time together. And like, you know, how can you not, like the physical presence? And there's, you know, there's a, there's a lot of people who that habit, especially when you're younger and you get, you know, more and more engaged with, you know, games and other things, changing back to the world, the way things were, you know, it's going to be some give and take, and I'll just be really interesting to see how that evolves. Thank you so much for your time today, Sarah. That's a great place to end this conversation. Thanks so much for having me.

Hey, one more thing before we say goodbye. The Knowledge Project is produced by the team at Fernham Street. I want to make this the best podcast you listen to, and I'd love to get your feedback. If you have comments, ideas for future shows, or topics, or just feedback in general, you can email me at Shane at fs.blog, or follow me on Twitter at Shane A. Parrish. You can learn more about the show and find past episodes at fs.blog slash podcast. If you want a transcript of this episode, go to fs.s.com slash tribe and join our learning community. If you found this episode valuable, share it online with the hashtag the Knowledge Project or leave a review. Until the next episode.