Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q So do you think that these companies should raise these kind of war chest, I think it's called, war chest funds, where they raise obscene amounts of money because they can? Do you agree with that, even though it might lead to a down round in the future?
A Um, you know, I think it depends on the stage, honestly. Um, you know, if you're at the super early stage, um, you know, most companies don't really have the luxury of raising a huge amount of money, right? They have really the, they're, they're sort of constrained by the market to, um, Unless they have, like, some rock star who's, you know, started a billion dollar company before, um, you know, they're constrained by what the world will do. Now, in the later stages, if you can get that money, um, and you can do it in a way where you don't have to, uh, agree to bad terms, then why wouldn't you take it if, you know, you can grow a little bit faster, you can insulate yourself a little bit better against You know, if there's an economic recession that happens in the near future, because if an economic recession happens, then A, it will be a lot harder to access capital, and B, you know, it'll slow your growth, right? I mean, everyone will start to feel, um, less excited about buying whatever your thing is. So, I mean, the way I think about a down round and worrying about it, or being smart about the way one worries about a down round, is in the nature of the terms of the financing that you're currently considering. And if you're, you know, you need to agree to a full ratchet to get the, uh, valuation that you were looking for, um, then I think either A, you should relax your valua…
AI assessment note: “in the later stages, if you can get that money... why wouldn't you take it”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q And at the beginning, did you have a particular investing strategy?
A You know, at the very beginning, I did not, um, and in some ways, I was very lucky to arrive just as the, as the dot-com crash was really, you know, becoming apparent as to how bad it was, because without a really clear strategy, it's like, you know, getting handed an AK-XVII and told to go shoot some stuff. Like, like, you know, it's crazy, uh, because there's lots of targets to go shoot at, but without a clear strategy, uh, You're gonna get, you know, you're gonna do poorly unless you're just super overwhelmingly lucky. And so it was good that in the first year and a half or so that I was at vantage point, there was, you know, um, not a, uh, a strong desire in the partnership to do new investments, and, you know, there was sort of death and destruction all around, and that really allowed me to, you know, have more deep conversations and develop my own sort of approach to, to venture investing and a real strategy.
AI assessment note: “You know, at the very beginning, I did not”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q And do you think having been CEO of a venture back, or two venture back startups, that that changed your attitude to portfolio companies and entrepreneurs?
A Um, for sure, yes. I mean, no human is, is, uh, is not affected by their experience. Um, I should say it was the founding VP of product management in the, in the first company, not founding CEO. Um, you know, the way I think of it is, um, you know, uh, uh, I had one good outcome and one bad outcome from my two startups that I did. And, you know, on the, in the abstract, um, It's easy for us to all look at, you know, how things are going and be, you know, sort of, um, cognizant of bad things can happen, you know, that's just sort of the randomness of nature, but having lived through, uh, the situation of spending years of time on something that ended up being a zero, it really, you know, brings into, um, high relief, uh, that abstract notion, and, you know, I was fortunate to have some really great board members across those two companies that I learned a Pun from, ah, in doing it. And the two things that I always say to, ah, an entrepreneur or CEO, um, after I've made an investment. The first one is, I'm fully aware that the CEO who's been working 60 plus hours a week in a specific sector for several years knows a lot more about that sector than me as a VC board member who, I mean, really can rarely spend more than five hours a week on a specific company and has only been in that sector for a relatively short amount of time. So 80 plus percent of the stuff that I'm gonna say Ye…
AI assessment note: “Um, for sure, yes. I mean, no human is, is, uh, is not affected”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q And at the beginning, did you have a particular investing strategy?
A You know, at the very beginning, I did not, um, and in some ways, I was very lucky to arrive just as the, as the dot-com crash was really, you know, becoming apparent as to how bad it was, because without a really clear strategy, it's like, you know, getting handed an AK-XVII and told to go shoot some stuff. Like, like, you know, it's crazy, uh, because there's lots of targets to go shoot at, but without a clear strategy, uh, You're gonna get, you know, you're gonna do poorly unless you're just super overwhelmingly lucky. And so it was good that in the first year and a half or so that I was at vantage point, there was, you know, um, not a, uh, a strong desire in the partnership to do new investments, and, you know, there was sort of death and destruction all around, and that really allowed me to, you know, have more deep conversations and develop my own sort of approach to, to venture investing and a real strategy.
AI assessment note: “You know, at the very beginning, I did not”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q And do you think having been CEO of a venture back, or two venture back startups, that that changed your attitude to portfolio companies and entrepreneurs?
A Um, for sure, yes. I mean, no human is, is, uh, is not affected by their experience. Um, I should say it was the founding VP of product management in the, in the first company, not founding CEO. Um, you know, the way I think of it is, um, you know, uh, uh, I had one good outcome and one bad outcome from my two startups that I did. And, you know, on the, in the abstract, um, It's easy for us to all look at, you know, how things are going and be, you know, sort of, um, cognizant of bad things can happen, you know, that's just sort of the randomness of nature, but having lived through, uh, the situation of spending years of time on something that ended up being a zero, it really, you know, brings into, um, high relief, uh, that abstract notion, and, you know, I was fortunate to have some really great board members across those two companies that I learned a Pun from, ah, in doing it. And the two things that I always say to, ah, an entrepreneur or CEO, um, after I've made an investment. The first one is, I'm fully aware that the CEO who's been working 60 plus hours a week in a specific sector for several years knows a lot more about that sector than me as a VC board member who, I mean, really can rarely spend more than five hours a week on a specific company and has only been in that sector for a relatively short amount of time. So 80 plus percent of the stuff that I'm gonna say Ye…
AI assessment note: “Um, for sure, yes. I mean, no human is, is, uh, is not affected”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q So do you get great deal flow just from being where you are, do you think?
A There are two answers to that. Uh, the short and simple one is yes, in a way that you just couldn't get any other place. Um, Because, you know, if I go to my local coffee shop, which I do every morning, I see venture guys in there, right? I mean, that's just, that's the business we're in. The same way that if you're in the, you know, the public market analysis, you know, business, you better be in New York City if you're going to be in the United States, or better be in London if you're in, in the UK, because that's where all those people are. So I think there's a natural sort of, um, uh, economy of, of, There's probably some good word or term for this that I can't remember, but you get an advantage of being around all those people and speaking that language and knowing all those, uh, you know, companies.
AI assessment note: “the short and simple one is yes, in a way that you just couldn't”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q So do you think that these companies should raise these kind of war chest, I think it's called, war chest funds, where they raise obscene amounts of money because they can? Do you agree with that, even though it might lead to a down round in the future?
A Um, you know, I think it depends on the stage, honestly. Um, you know, if you're at the super early stage, um, you know, most companies don't really have the luxury of raising a huge amount of money, right? They have really the, they're, they're sort of constrained by the market to, um, Unless they have, like, some rock star who's, you know, started a billion dollar company before, um, you know, they're constrained by what the world will do. Now, in the later stages, if you can get that money, um, and you can do it in a way where you don't have to, uh, agree to bad terms, then why wouldn't you take it if, you know, you can grow a little bit faster, you can insulate yourself a little bit better against You know, if there's an economic recession that happens in the near future, because if an economic recession happens, then A, it will be a lot harder to access capital, and B, you know, it'll slow your growth, right? I mean, everyone will start to feel, um, less excited about buying whatever your thing is. So, I mean, the way I think about a down round and worrying about it, or being smart about the way one worries about a down round, is in the nature of the terms of the financing that you're currently considering. And if you're, you know, you need to agree to a full ratchet to get the, uh, valuation that you were looking for, um, then I think either A, you should relax your valua…
AI assessment note: “depends on the stage, honestly... in the later stages, if you can get that money”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q Do you think many CEOs have the, the gumption and the courage to stand up to their VCs and say, well, I think this is the 80% that you're not right on?
A Um, the best ones do. And they don't. And it's not so much a gun. I mean, it can be a quiet introvert. Um, it doesn't take some sort of, you know, chest pounding, uh, person to do that. It has to be somebody who says like, so by that, do you mean we should do this? And then, you know, clarify it. And then you, and then, you know, you get to the clarified understanding of what you're trying to communicate. And then I go, that's interesting. I, you know, my, my first Concern would be, you know, X, but let me go look into that, and then they check it, and they come back, and after spending not too much time on it, say, you know, as we looked into it, X really is kind of a killer issue, or that's not practical for a reason why, or whatever it is. But I have seen, unfortunately, the case where, you know, um, there's nothing in the training of somebody who's, you know, been in corporate America, or, you In, but anywhere in the, in the world, that trains you for dealing with a board of, you know, smart, opinionated, um, people who have some control over your life, but aren't speaking of, uh, with one voice, and so it's just its own separate skill and, um, and, and job to learn.
AI assessment note: “the best ones do. And they don't. And it's not so much”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q So do you get great deal flow just from being where you are, do you think?
A There are two answers to that. Uh, the short and simple one is yes, in a way that you just couldn't get any other place. Um, Because, you know, if I go to my local coffee shop, which I do every morning, I see venture guys in there, right? I mean, that's just, that's the business we're in. The same way that if you're in the, you know, the public market analysis, you know, business, you better be in New York City if you're going to be in the United States, or better be in London if you're in, in the UK, because that's where all those people are. So I think there's a natural sort of, um, uh, economy of, of, There's probably some good word or term for this that I can't remember, but you get an advantage of being around all those people and speaking that language and knowing all those, uh, you know, companies.
AI assessment note: “the short and simple one is yes, in a way that you just couldn't”
Answered raw tape
D 5 · C 4 · P 3 · Cm 4 4.05
Q Do you think many CEOs have the, the gumption and the courage to stand up to their VCs and say, well, I think this is the 80% that you're not right on?
A Um, the best ones do. And they don't. And it's not so much a gun. I mean, it can be a quiet introvert. Um, it doesn't take some sort of, you know, chest pounding, uh, person to do that. It has to be somebody who says like, so by that, do you mean we should do this? And then, you know, clarify it. And then you, and then, you know, you get to the clarified understanding of what you're trying to communicate. And then I go, that's interesting. I, you know, my, my first Concern would be, you know, X, but let me go look into that, and then they check it, and they come back, and after spending not too much time on it, say, you know, as we looked into it, X really is kind of a killer issue, or that's not practical for a reason why, or whatever it is. But I have seen, unfortunately, the case where, you know, um, there's nothing in the training of somebody who's, you know, been in corporate America, or, you In, but anywhere in the, in the world, that trains you for dealing with a board of, you know, smart, opinionated, um, people who have some control over your life, but aren't speaking of, uh, with one voice, and so it's just its own separate skill and, um, and, and job to learn.
AI assessment note: “the best ones do.”
Answered raw tape
D 3 · C 4 · P 3 · Cm 3 3.30
Q So how can founders develop that and learn that skill? Is there any books they can read? Is there anything they should Be doing in particular to help them along the way?
A I think I'm just simply understanding the structure of what a board is. Your board is not your boss, right? It's an, and, and, and by the same token, you know, becoming CEO of a young company is not sort of about unfettered, um, open field running either. Uh, a board is an amalgamation of people who have a collective interest and have their own separate Individual interests. And, you know, I don't know that there's a, um, I guess the most useful and valuable advice would be just to recognize the role of a board and what it is, um, and not to treat it as a bumpy, you know, uh, pudding of my, instead of having a single boss, I have these five people as a boss.
AI assessment note: “simply understanding the structure of what a board is.”
Redirected raw tape
D 2 · C 3 · P 2 · Cm 2 2.30
Q So how can founders develop that and learn that skill? Is there any books they can read? Is there anything they should Be doing in particular to help them along the way?
A I think I'm just simply understanding the structure of what a board is. Your board is not your boss, right? It's an, and, and, and by the same token, you know, becoming CEO of a young company is not sort of about unfettered, um, open field running either. Uh, a board is an amalgamation of people who have a collective interest and have their own separate Individual interests. And, you know, I don't know that there's a, um, I guess the most useful and valuable advice would be just to recognize the role of a board and what it is, um, and not to treat it as a bumpy, you know, uh, pudding of my, instead of having a single boss, I have these five people as a boss.
AI assessment note: “I don't know that there's a, um, I guess the most useful and valuable advice”
