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Q&A with Elizabeth Zalman and Jerry Neumann, coauthors of Founder vs. Investor: The Honest Truth About Venture Capital from Startup to IPO

.Thinking in Bets is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Elizabeth (Liz) Zalman and Jerry Neumann have together (or, more accurately, versus each other) written Founder vs. Investor: The Honest Truth About Venture Capital from Startup to IPO


Thinking in Bets is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Elizabeth (Liz) Zalman and Jerry Neumann have together (or, more accurately, versus each other) written Founder vs. Investor: The Honest Truth About Venture Capital from Startup to IPO, which came out last week (September 12). Zalman is a two-time founder of venture-backed startups. She is the Founder in the book. Neuman is a 25-year veteran of venture capital. After investing at earlier and earlier stages, he now identifies his specialty as “zero stage, because pre-seed is now too late for me. If you’ve raised money, I won’t even look at it.” He also teaches entrepreneurship at Columbia University. Neumann is the Investor. A venture investor introduced them 12 years ago, and Neumann has invested in both of Zalman’s companies.

Why I love this book

Founders and venture capitalists start as collaborators, united in the quest to create breakthrough products and phenomenally successful new businesses. But the relationship can collapse under the friction created by each side’s differing perspectives and goals. Zalman and Neumann surface that friction in this important and exciting new book, drawing on their own experiences with the founder-VC relationship.

Notably, they don’t reconcile or unify their positions, instead exposing the conflicts and letting them hang there.

The uniqueness of the book’s approach: The VERSUS

Annie: As you point out in the opening of the book, there are a lot of books written from the investor’s perspective and lots of books written from the founder’s perspective. Your approach seems very different, taking the two perspectives and not really merging them together, not trying to come to agreement, but showing how founders and investors do things and view things differently. A pair of related questions for each of you: Why didn’t you write your own book? And why did you decide to come together from these two disparate perspectives and write this book?

Jerry Neumann: After doing this for so long, every time I read something that has been written about venture capital or startups, I feel like I’ve read it before. There’s a lot of advice out there from both sides, from the venture capitalists and from the entrepreneurs, and everybody’s trying to make it nice. They’re trying to remain in the middle and seem reasonable, but that’s not how it really works. When you’re sitting across the table from the founder or sitting across from your venture investor, everybody’s not always trying to be reasonable. People have their own points of view, and the literature doesn’t give you an understanding, when you sit across from the other person, of why they’re acting the way they are.

Liz Zalman: From my side, it’s twofold. To the playing-nice point of view, people don’t actually say what’s on their mind most of the time. They care about other people’s feelings, and they don’t want to become uncomfortable themselves. I think that’s why people ghost you when you’re dating and break up. I wanted to put truth out into the world. That’s number one.

Number two, as a founder, I will always have a co-founder or multiple founders. I work better as part of a team. That was maybe one of the more stressful points of us being friends in this book. Jerry tends to work alone, and I tend to work as part of a team. That was something we had to figure out how to do together as part of authoring the book. As Jerry says in the first chapter, we’ve had some of the biggest fights in our relationship trying to get this done together and we’ve become stronger for it. Those two things came together when the idea for the book came up.

Annie: The conflict between your perspectives – founder versus investor – really comes through in the writing. I found it interesting because when people are writing a book together, they’re usually trying to unify a point of view. Obviously, you’re not doing that. It’s not that you don’t have points of agreement, but it feels that what you’re trying to do is to surface the different points of view on the founder-investor relationship, the purpose of that relationship, and how that relationship is supposed to develop. And then you’re willing to let it hang there, without coming to some kind of tidy resolution. How did you come to that as the approach to the book?

Jerry Neumann: It was one of the principles of the book that we insisted on together. The whole thing started when I wrote this blog post about founders getting fired, “Your Board of Directors is Probably Going to Fire You.” From the pushback I got from other VCs contrasted with what I heard in talks with Liz and other founders, I realized the two positions were somewhat irreconcilable, so why not talk about that?

During the writing, there were times where Liz and I, who are friends, would alter our writing to agree with the other person to some extent. I pushed back on Liz sometimes when she’d say, “Well, I guess you’re right.” I’d press her on whether she really believed I was right, and she’d say no. And she did the same to me. We were pushing each other to be true to what we believed and not be agreeable.

Liz Zalman: There’s a quote on the back of the book that shows us we were successful: “’Super problematic…over the top.’ Venture capitalist name withheld.”  

In the book, the opinion we embody is that he’s very much an investor and I’m very much a founder. The truth actually is that we’re both much more in the middle. I am pro-investor in many cases, even so a lot of what I say feels so inflammatory and so incendiary. When has a founder ever said in public, “My board meetings are a fucking waste of my time and I hate doing it. It’s all pomp and circumstance”? And when has an investor ever said, “I need returns and this is what my distribution of all of my investments needs to look like for me to make money and be able to raise my next fund”? I’ve never heard an investor say that publicly.

That blurb is the reaction that we wanted. These truths that are out there and they exist just below the surface, but nobody talks about them or gives weight to those voices in real life.

Jerry Neumann: Founders and VCs don’t talk about it with each other. VCs will talk to other VCs about returns, and founders probably talk to each other about how useless they think their board meetings are. But it is interesting because there are things that Liz said in the book where I was surprised and sometimes a little bit hurt because I am “one of the people” she’s talking about. I’m like, wow, you never said that to me.

Things they said that surprised or hurt each other

Annie: Jerry, what was one of the most surprising things Liz said?

Jerry Neumann: At one point she said to me that I’m not vocal enough or insistent enough in my advice, so she doesn’t hear it as advice. I’m like, “I was just trying to be helpful and useful and give you advice without being directive. You’re the CEO.” And she’s like, “You say these things and I don’t even remember you saying them.” That’s fair criticism that somebody should have given me 25 years ago.

Annie: What was the most hurtful thing she said?

Jerry Neumann: That venture investors have no useful input in terms of where the company’s going or how it should be run. I like to think she wasn’t thinking of me when she wrote that.

Annie: Liz, what’s the most surprising thing that Jerry said?

Liz Zalman: Jerry is very pro-founder in real life and has publicly stated that he believes that when the founders are no longer part of the company, the company tends to go to zero. I think he’s right, but I was surprised to hear him say that there are more moments than I would think that it is okay to replace the founder as CEO. That was surprising to me because he is so pro-founder, but in that moment, he is somebody who’s trying to make this thing have outsized returns and, tactically and operationally speaking, this person isn’t cutting it. That was a little more exacting and precise. Definitely devoid of emotion.

Annie: And what would you say was the most hurtful?

Liz Zalman: That might be also the most hurtful thing, because it’s so personal and so intimate. One of the hardest things that founders have to deal is when somebody says, “You are not good enough to do this thing.”

Why are so many relevant subjects off limits between investors and founders?

Annie: I get that founders think board meetings are a waste of their time, and that investors are focused on generating returns. But it doesn’t seem either side is completely oblivious to these things. Why do people think these subjects are, as the unnamed VC said, “super problematic”? Why don’t founders and investors, in the course of their business relationship, want to even mention these seemingly relevant subjects to each other?

Jerry Neumann: With VCs, it’s more than just that you have to have returns because that’s your job. Every company has that. Everybody who earns a salary focuses on making money. I think that’s acceptable and almost doesn’t need to be said. But in venture capital, there’s a difference, which is the people who make the most money are the best VCs. If I want to be one of the top VCs in the world, if I’m a competitive person, then that’s measured in dollars. I want to be good at what I’m doing, so there’s more motivation for that, and that makes it sound kind of crass in a way. I’m making money, not that I need it to pay the bills, but because that’s how I’m measured.

Liz Zalman: With the founder there, the VC never explicitly states that out loud. And if they did, it would be conflated with this image that they’re trying to give, which is, “I can be so helpful to you.” Their job is to make more money, and yet Jerry’s money is just as green as the next person, so he needs to sex it up. Why do I want Jerry’s money over somebody else’s money?

And so they promise founders the world. “I can help you do this. I can get you these customers, I can help you hire.” Most of them, in my experience, tend to be good at one thing and one thing only. And most founders don’t try to go and figure that out. They just assume that the VC can deliver the world because that’s marketing, that’s how VCs get you to take their money. That’s the start of where things actually break down, with that original premise, way back in fundraising, which is, “I’m going to help you build this amazing thing by giving you all this help and all this stuff.” Then, once the docs are signed, the founders are like, “What are you doing for me?”

Should market forces align some founder-investor conflicts?

Annie: I think it’s interesting because, as I listened to you talking about it, it seems to me that there’s less conflict in that than there necessarily needs to be. Aren’t there market forces between founders and investors that would help to bring those things into alignment?

Jerry Neumann: I think there’s a different incentive. For me, and probably more so for other investors, a 5% chance at a $10-billion-outcome is much more valuable than a 50% chance at whatever the equivalent expected value would be. It still rankles a bit that because of one investment I didn’t make, I’ll never be on the Midas list, and not that the investment would have changed the outcome so much for me.

Back in 2000, I remember giving a founder advice that was, basically, go big or go home. You should definitely do this thing, spend this money, hire these people, and go after this market. Then, the dot-com bubble collapsed and a lot of our customers went away and the company failed.

I think I partially contributed to that by telling her to spend the money at the exact wrong time. But for me, it was like, “Look, you’re either going to be a big company or who cares.” I’ve tried not to do that since, or at least to be able to tell the founder, “Here are the risks as well as the rewards,” and not to just push my own risk-taking agenda onto the founder. But the reason I did it was because it made sense to me. It totally fed my objectives at the time. I don’t think it really fed that founder’s objectives.

Annie: Have you received advice like that, Liz?

Liz Zalman: Yes. It comes in a little bit softer. This example is in Chapter 6, Exits. At my last company, we had a cash-and-stock offer, I think for $50 million. The cash, essentially, paid back the investors at cost. The stock portion would’ve been life-changing for the founders. The company that we were talking with ended up becoming one of the biggest tech IPOs. I talked to one of our seed investors about it, and he said, “Yeah, but why would you do that? Look at the market trajectory. Look at where you’re positioned. Wouldn’t it be better if you were to go on? I see a path to five times that valuation on your next round. You’ve only been at it for five years. It’s really a 10-year journey.”

So I’ve heard it, that very soft pressure. What was happening in his mind is that we were well set up to be one of the fund returners and he had already figured the math and gamed it out. And I know because I was one of the speakers at his firm’s LP conference, the marquee chick leading an infrastructure company.

I’ve heard it from Jerry, actually in different terms. There’s an excerpt in the book in which he sat me and my co-founder down, and he outlined how far behind we were in hiring and already behind the valuation that we had just closed on. He was essentially saying, “You need to go big or go home, and you’ve already made the decision to go big and shame on you for not having thought this through and spent this money.” Jerry was absolutely right in that moment. I was not being a very good CEO.

Jerry Neumann: Can I say one thing about that VC that was pushing Liz? I don’t think that he was being disingenuous. Knowing VCs, he was probably thinking, “Why would you settle for that amount of money? I don’t want to settle for that amount of money. I’m sure we think the same way, right? I’m sure that I’m thinking we could make five times that amount of money. Why wouldn’t you want that as well?”

Do founder and investor goals start aligned and later diverge?

Annie: Don’t you think also that part of the issue is that your values and your goals can start off aligned and then diverge? And when they diverge, people aren’t necessarily realizing that the divergence has occurred. The way that I would think about it is, if you’re creating a company and you’re bootstrapping it, then probably what you as a founder would consider a great outcome is going to be different than if you are going the venture-backed route. Obviously, if you’re going the venture-backed route, you’re giving up equity in exchange for accelerant in the form of money. It seems to me that, as a founder, if you’re going the venture-backed route, you’ve already made a statement about go big or go home.

If that’s the case, then at the moment of investment, particularly when it’s early, maybe the values are aligned on that. Then, you get into a situation later where where someone wants to acquire you and the investors are going to get their money back and the stock for you might be life changing. Your values, previously aligned, have changed and the misalignment gets exposed in that moment. Does that sound reasonable as part of the issue?

Jerry Neumann: Maybe. I think you’re giving too much credit to founders, frankly.

One founder I was talking to six months ago said, “I’ve got this company, we’re using this technology, nobody’s doing this. We already have customers who are interested. We’re signing them up. We’re going to be a $30 million company in two years.” I said, “Great. And then what?” He’s like, “Then we’re going to be a $30 million company.” I was like, “Okay, but that’s not venture scale. I can’t invest in that.” He’s like, “Why not? It’s like a 100% chance at $30 million. Why wouldn’t you do that?” I said, “That’s not what I do. I mean, if it’s a 100% chance, go get a bank loan.” But he was angry at me for not understanding how great his business was. It’s just not what I do, but he wanted venture money. I was like, “Why are you even taking venture money? It’s crazy to take venture money. You can own 100% of your $30-million-a-year company. Why would you give some of that up?”

He really did not understand what it looks like from my shoes.

The (rarely questioned) attraction of founders to venture capital

Annie: Liz, you’ve been a founder yourself, and you’re also in the founder community. Is it the case for founders that it’s just become so normal to want to get into Y Combinator, to go the venture route? Are founders thinking, in advance, about what the scale of the company is that they want to create and whether it makes sense to go the venture route or not? Is this something that, in general, you think the community is thoughtful about? Or do you think that there is a misunderstanding between VCs and founders about this particular issue?

Jerry Neumann: I want to point out that you’re talking the one person who’s probably ever said no to YC.

Liz Zalman: True. And then, to their credit, they said that nobody who’s ever turned down YC has gone on to become a billion-dollar company and there are no outcomes between zero and a billion.

I’m going to agree with Jerry, for a slightly different reason. I think there is little to no thoughtfulness in the founder community, especially today, and it’s been worsening. Somehow, some way – and I think this happened because of the explosion of YC and Techstars and venture studios and the proliferation of accelerators everywhere – venture capital is now the default way to start a business, any business. Not a single founder with whom I’ve spoken in the past 24 months has paused and said, “I wonder if I need this,” or, “I wonder if I can bootstrap to something or maybe I can take out a loan against my house, like my grandparents did when they were starting their company.” It’s venture capital or nothing. They simply reach for it and because they’re reaching for it and there’s no thoughtfulness, they get to the other side of it and all of a sudden they realize they’ve made a deal with the devil and they’re like, holy shit.

I hate to agree with Jerry, but I do.

Annie: If you’re being thoughtful about whether you’re creating the type of business for which venture makes sense, then don’t you kind of move yourself out of that feeling like you made “a deal with the devil”?

Liz Zalman: I’ll speak from personal experience. I’ve started two companies. In the most recent company, I raised a million dollars for the pre-seed round. I don’t know that I sat there and thought, “I think there’s a billion-dollar business here.” I definitely said it in the fundraising deck. I’ve definitely said it in every round since. That company is certainly in a market and attacking it, and it is very clear how that could become a $10 billion company. But I reached for venture capital because one of my co-founders couldn’t afford to leave his job and we needed to pay him a salary. And the other one also had very little money in the bank, and I was the only one who would be able to work without a salary for a year or two. That was the option, and I knew that I could tell a good enough story. I also knew that because I had a track record the probability of getting a raise done was high. In those moments, I reached for the thing that I knew could catalyze the company into existence, and I also believed in our ability to figure it out.

Jerry Neumann: A lot of founders, instead of thinking that venture investors invest in companies that become big, think that companies become big because venture investors invested in them. You can see how there’s the correlation there, but businesses don’t become big because venture investors invested. That’s not how it works. Venture investors choose companies that can become big. I think people have an idea that, if they want to be big, they have to get venture capital, which just elides the fact of whether or not they can become big at all.

Promoting empathy and understanding between founders and investors at the outset

Annie: At the core, some of the disagreement might be reduced if we were more transparent about what makes a company reasonable for venture backing. In your case, Liz, you knew why you were going to get venture capital, so you understood that there might be some misalignment because part of the reason you were going that route was so that you could get the full focus of your co-founders. But if most people aren’t being as thoughtful going into it it, then part of the value of this book is to say out loud that the problem isn’t that either size is evil or unreasonable or too demanding.

If you enter into it understanding what you’re entering into, then it helps the relationship along afterwards. We may have gotten to a place where, to your point, Liz, that it’s just become the default. People aren’t actually thinking about it, and this is one of the things that I love about this book. What is a VC? What are they actually trying to do? What are their expectations? How do they think about a business or their portfolio? If we could expose that more and be explicit and not have VCs or founders having those conversations only among themselves, if VCs and founders have these conversations together, it might help on the entry, which would then take out some of the friction.

Jerry Neumann: That is the hope. That people will read the book and not have the preconceptions that we fight against afterwards.

Liz Zalman: I was invited to sit in on one of my investors’ portfolio review sessions. They went through every single one of their funds and every portfolio company in each fund. The partner that had done the deal gave a 30-second summary. The process was long, it was tedious, and it took two days. And it was so enlightening for me because I realized in that moment that their bet on me was 1/10th of a percent of their deployed capital and maybe 2% of the fund. I saw how they broke down growth capital and follow-on capital after initial investments, how they analyzed companies, and how the composition of funds was shifting, especially as crypto came to light. I was mesmerized because that’s their business. My business is building this piece of software that people log into. Their business is building a portfolio of businesses like mine and constructing that portfolio well.

I almost wish that founders – and that I – could be a venture capitalist for a day. I wish that were a mandate. You have to sit in a board meeting from the investor perspective, you have to look and read board materials. You have to sit in on internal partner meetings. It would have allowed me much earlier on to see the other side of the equation, which was incredibly opaque to me. In many ways it still is, but I’ve been able to pull back the curtain slightly because I’ve had so many years of being exposed to various things. I wish we had a bootcamp for founders to appreciate what it’s like to be an investor. And I say that being very pro-founder.

The conflict between portfolio holder and individual in the portfolio

Annie: What you’re saying makes me think about something which is a problem across a lot of different sectors and verticals. There’s always a conflict between the portfolio holder and the individual in a portfolio. We can think about, for example, decisions that a coach makes for a team. The coach is working with a team of individuals, but in some ways the coach is a portfolio holder, trying to generate the highest returns across the portfolio. And that may conflict with what one particular individual on the team wants or what is best for them in the long run.

It feels like that what you’re talking about. You got a glimpse into how the portfolio holder is thinking, and it’s a little bit jarring. Your perspective is, “I’m an individual in your portfolio and you should have all your focus on me.” Then, you find out that only this tiny fraction of the portfolio has anything to do with you.

Jerry Neumann: It’s such an interesting way to look at it. When I was in grad school, I worked my way through grad school coaching. I was the coach of the rowing team, and people would say, “I don’t understand why you’re not in that boat.” And I’d say, “Because I want to win.” And they would be like, “okay.” They might not feel good about it, but there was never any mystery about why I was making decisions. It’s interesting, I think, because founders don’t really see that when you say, “But I’m doing this for this reason and that’s why I’m making these decisions.” And founders often just don’t get that.

Annie: Do you think that founders don’t get that, Liz?

Liz Zalman: I think there is no separating the founder and the operator or the founder and the company. It is just intensely emotional. You and Jerry both gave sports analogies. You show up, your body shows up, and your body is either in tune enough or it isn’t. Your brain either knows the angles of the court or it doesn’t. Success there is black and white. With startups, it is gray. It is a hundred different gray decisions a day that’s going determine whether you make it or not. Guile or muscles is just not enough.

That is, again, another source of the tension, which is why I wish somebody would say to me, “You’re doing a really bad job at this particular thing. You are a micromanager. I understand that you have a desire to do the things that you now have a team to do because you love being in the nitty gritty. But Liz, you have a decision to make. You’re either going to zoom out or you’re going to fail as a CEO. Which do you want? You want to be a CEO? Great. Let’s now talk about how to make sure that you can walk the walk that you’re embodying. I gave you this title. You’re not doing so well. Let’s make sure you can sit in the title.”

That sort of tough love would work on me because then I can put together a plan. If I don’t execute the plan, then it’s very clear that I haven’t been doing the work. But to be surprised by it or to have somebody say, “Oh, you’re doing a great job,” it just doesn’t work.

Fundamentally, how do we get people to tell each other the truth?

Annie: This goes back to a theme of the conversation and a theme of the book. I feel the reason that you wrote the book is to surface this stuff. If we could surface this stuff, then we’d all be happier. If you really understand from a VC’s perspective what type of business they’re expecting you to become, then you can make a more reasoned decision about whether you should take venture money. If you understand the difference between the portfolio holder and the member of the portfolio, which you, Liz, did when you sat in on the portfolio review, that would take away some of the tension.

So, how do we surface these differences? This is something that I’ve written about. It’s very difficult to get people to tell you the truth, and it sounds like something you’re frustrated by. The thing about getting people to tell you the truth is that you have to be very clear that the truth is what you want. On the investor side, they should have a motivation to tell you the truth, even if it’s going to be hard and it’s not something that you want to hear. And on the founder side, you have to be very clear that you want the actual truth. Don’t tell me I’m doing a good job if I’m not. I want to know as early as possible, in the harshest possible terms, knowing that you’re saying it with love, that I’m a micromanager and I’m going to have huge churn with top talent because they’re not going to want to work under me.

To me, it’s about permission giving. I’m giving you permission to tell me something awful. Then, on the investor side, they have to be willing to take that permission and actually go with it. I think that’s something that’s hard for people to do, maybe for the same reason that you felt the need to write this book, that people don’t say those truths out loud as much as they should.

Jerry Neumann: As an added difficulty, from my point of view, I look for founders who are extremely talented, really good at what they do, driven people who can make things happen. Yet they’re also people who don’t seem to be able to hold a job. They’re different. They’re not always the easiest person to tell the unvarnished truth to. There’s an anecdote in the book where I talk about a VC who was like, “I kept calling this founder and telling him he was doing it wrong, that he needed to change this, he needed to change that. And after a few weeks of this, he just wouldn’t take my calls.” The investor was right, by the way, and that company ended up going out of business. But you can’t tell people the truth if they stop listening to you.

Annie: I think that’s why permission giving at the start of the relationship is really important.

Liz Zalman: Somebody asked yesterday if I had ever gone to therapy with an investor, and I said, no. I’ve definitely been to founder therapy though. I’ve been with my co-founders, certainly with family members, and I see a therapist weekly. But a few years ago, during one of my fundraises, I tried to get investors a clause added as part of the docs. It was essentially a code of conduct. If this set of bad things happens, myself as well, any director is off the board. It was things like if you’re accused of a crime – murder, rape, anything like that. They agreed to some of it, but it was carved back a lot. It had to be convicted of a crime, and the list of crimes was carved back. At the time, the people that we were dealing with were on the boards of public companies, but it was crazy to me that their funds wouldn’t commit to something which seemed very simple, that I would’ve signed in a heartbeat. I love the idea in spirit, a non-binding commitment. I commit to you that I’m going to do these things and you commit to me, like marriage vows essentially.

Annie: I’m not talking about a formal commitment. I’m just saying, “Hey, Jerry, you invested in my company. Can you tell me when you see that I’m really screwing up? I actually want to hear it.”

Jerry Neumann: People say they want the truth, but they don’t really. I tend to be more careful, and I think I did misread Liz about that. I think Liz actually could take the truth. But there’s also the fact that you have successful people who have all these weird ways of doing things. If you’re a venture investor for any length of time, you can’t say, “I know the one right way of building a multi-billion-dollar company,” because I’ve seen people do it in one way, and I’ve seen people do it in the exact opposite way. I don’t have a monopoly on truth. I can’t come and be like, “Here’s the truth.” I would never say that. I’m careful about giving advice. I know I can never be wrong. If I’m wrong once, they’ll never listen to me again. I need to go in there, and if I think I know the right way, then I need to convince them that that’s the right way. I need to walk them down that path. I can’t just walk in and be like, “Here’s how you do it,” except in very simple things.

One last question for Liz

Annie: This has been a super fun conversation for me. I hope it’s been fun for you. I’ve taken a lot of your time, so I have just one last question for each of you. Liz, would you take venture again?

Liz Zalman: Yes. I know for certain that I cannot be satisfied with a $30-million-a-year business. For my next one, I’m not touching enterprise software. I think it’s got to be something very black or white. It’s not going to be a flying car, but with a flying car, you either deliver a car that flies or you don’t. There’s not going to be a car that crawls. For that, venture capital is the choice. However, I hope that I will be able to use the experience that I have and the years under my belt and the relationships that I’ve built to adjust some of the rules in the contract to help mitigate the risk of things that I’ve experienced.

One last question for Jerry

Annie: Jerry, can you share something you learned from writing the book with Liz that will change how you do things in the future?

Jerry Neumann: On this same issue, I’ve been doing this for a long time, and yet I will do things slightly differently from now on having read Liz’s section of the book. When you’re an investor, founders just don’t tell you certain things because it wouldn’t be worthwhile for the founder to tell the investors. Over the years you’re thinking, “I’ve said this thing and they seem fine with it, so we’re all moving on,” not realizing that maybe they’re not fine with it, and they’re just not saying it. It’s opened my eyes a bit to what people weren’t telling me. I’d like to say that’s humbling, but “humbling” is not the right word. Maybe the word is “annoying.” It’s annoying that, after doing this for 25 years, I didn’t realize that I might go into a board meeting and think we all left agreeing on the course, and the founder is probably going back and saying, “This is ridiculous.” It probably behooves me to understand what they’re thinking a bit more.

Annie: While reading the book, I felt this tension between the two sides, but at the same time it seems like it’s going to make everybody better because these points of view are getting surfaced. If people actually pay attention and read it, the ecosystem will function much better.

This is just such a fun book, which is maybe a strange way to describe it because it is also uncomfortable in a truly necessary way. Thank you both for writing it.

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