The Exchanges

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 →

Harry Stebbings argument clarity score 3.9/5 from 55 exchanges on raw tape · average scores: directness 3.5 · coherence 4.2 · precision 4 · compression 3.8 record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q building or schmoozing, but I, you know, there's a lot of the best founders, you know, they just want the same guys that are in Figma, the same funds that are in Figma. They do. Right. And And 20 VCs above the line, but it's not, it doesn't have the storied history of, uh, of benchmark. What do you think, Harry? That's why I'm not sure I would leave benchmark.

A I think people greatly over-exaggerate the impact that this has on Benchmark, and I don't mean that rudely to Victor, but I don't think any firm has played AI in the last 18 months as well as Benchmark have done, despite the team churn that they've had. Let's just go through this. McCaw over a hundred million in ARR. Hey Jen hitting a hundred million in ARR. Fireworks a hundred and forty million in ARR. Sierra with Brett Taylor over a hundred million in ARR. Manus AI, the best Chinese AI team there is. Lagoor are the best European AI team there is in many respects, all with double digits ownership in one single fund. Hell, how do I be an LP in that fund?

AI assessment note: “I think people greatly over-exaggerate the impact that this has on Benchmark”

Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q always look to buy a terrestrial asset on the cheap, right? And, and, and, and tack on eight figures of revenue. This has been true since the dawn of the internet. Um, but they didn't pick you. That's the problem. They didn't pick you, did they? They're not going to, it's not durable revenue in any way, shape or form, right? So it's financial engineering is all in most cases.

A I would actually push back on both of you. One of my fastest growing companies has gone from zero to thirty million in revenue in two years with a pure roll-up play, which is helped by AI tooling. And to your point on like the customers, uh, not picking you, the customers are all pretty much identical. It's a real estate management product. Um, they are identical in the service that they require, the product that they engage with. There is zero ambiguity. And so the ability to roll out to a uniform customer base makes it a very efficient model actually. Uh, and so the things that matters most then is just acquisition price. Can you acquire it effectively at a good enough price? What's your speed of turnaround in terms of your payback? And what's your margin juicing? Like we go from five to 40% in six weeks. That's a big increase in a short time.

AI assessment note: “the customers are all pretty much identical. It's a real estate management product.”

Answered produced feed D 5 · C 5 · P 5 · Cm 5 5.00

Q always look to buy a terrestrial asset on the cheap, right? And, and, and, and tack on eight figures of revenue. This has been true since the dawn of the internet. Um, but they didn't pick you. That's the problem. They didn't pick you, did they? They're not going to, it's not durable revenue in any way, shape or form, right? So it's financial engineering is all in most cases.

A I would actually push back on both of you. One of my fastest growing companies has gone from zero to thirty million in revenue in two years with a pure roll-up play, which is helped by AI tooling. And to your point on like the customers, uh, not picking you, the customers are all pretty much identical. It's a real estate management product. Um, they are identical in the service that they require, the product that they engage with. There is zero ambiguity. And so the ability to roll out to a uniform customer base makes it a very efficient model actually. Uh, and so the things that matters most then is just acquisition price. Can you acquire it effectively at a good enough price? What's your speed of turnaround in terms of your payback? And what's your margin juicing? Like we go from five to 40% in six weeks. That's a big increase in a short time.

AI assessment note: “to your point on like the customers, uh, not picking you”

Answered raw tape D 5 · C 5 · P 5 · Cm 5 5.00

Q want to have like X number of managers that look like you, We've invested in two or three of them, and so we have another, like, you know, four or five to go, right? Like whatever the numbers are. Um, so trying to get that, that feel, I think is really, really valuable. Um, and whatever questions it takes to answer that, I think is, is what you're looking for.

A I always ask about geography. I find if you're the first in a new geography, it's probably very unlikely. I always ask, like, on check size, like you said there about the ones that are massive checks, like, if they write twenty-five million dollar checks and you're raising a 30, forty million fund, you're pretty much qualified out straight away. I do check size, geography, existing portfolio for them, and then I always like to say, I think you can be quite bold in your fundraise, and so I always say, like, listen, I'm really optimizing for long-term partnerships, and I think trust is built over time. Can you talk to me about how you think about how you support your portfolio in the long term? And then if you're like, actually we take a case by case basis, you're like, oh, okay.

AI assessment note: “I do check size, geography, existing portfolio for them”

Answered raw tape D 5 · C 5 · P 5 · Cm 5 5.00

Q But you've also interviewed some of the best in the business, from Peter Fetter to Brad Feld, and with that in mind, what have been some of the most prominent takeaways for you?

A So I think I've obviously learned a ton from interviewing so many great VCs. I think if we start with what it takes to get into the industry, Pat Grady said to me that never has the rate of decay on operational experience been greater. I think now there's an element of diminishing returns almost. With regards to having operational experience due to the sheer advancement in technology, what one might have as experienced as an operator 10 years ago is now a different world with the ever-decreasing cost of starting a business, the rise of AWS, the changing funding environments, proliferation of distribution channels. Of course, there's still a huge amount to be taken from time in operations from a managerial perspective, but I don't think it can necessarily be held in this holy grail regard as the only way to enter the industry. I remember when I was debating getting into VC, Peter Fenton said to me, there's only one way to Be a great VC, and that's to be a VC and learn and iterate. So I think from that VC entrant perspective, that definitely taught me a lot. On the investment side, I really learned a lot from Roger Ehrenberg at IA Ventures on the importance of investing with strict discipline. At IA, they take a very artisanal and precise strategy approach, looking for high ownership with strictly concentrated portfolio. So Roger definitely taught me a lot with regards to the imp…

AI assessment note: “Pat Grady said to me that never has the rate of decay on operational experience”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q you would pass on an opportunity. But I'd say, by and large, if you're the one instigating these rounds and you're the one that's preempting these rounds, you can kind of help figure out what the right price is for a company at any given moment. And I do think you want to think about it last because, again, These generational companies, it's almost never too late for them, right?

A I agree with that, that we have a very kind of clear litmus test, which will make us make many mistakes, and which is why we should change it immediately. But it's like, when we think about our entry price, it's true. When we think about our entry price, do we think that we are able to three X that entry price within the next fundraising round? And so if the company says, hey, we're going to be at, are we going to go from one to ten million by the end of this year? And because of that, we're going to be able to raise at three 50. Great. Well, we're paying 70 for the A. I can totally see my three X there. Or it's like, well, actually we're only going from one to four because we're a slow enterprise sales cycle, but we're paying one 50 for this incredibly hot A. One to four, I'm not raising it 300 if that's the case.

AI assessment note: “do we think that we are able to three X that entry price”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q you would pass on an opportunity. But I'd say, by and large, if you're the one instigating these rounds and you're the one that's preempting these rounds, you can kind of help figure out what the right price is for a company at any given moment. And I do think you want to think about it last because, again, These generational companies, it's almost never too late for them, right?

A I agree with that, that we have a very kind of clear litmus test, which will make us make many mistakes, and which is why we should change it immediately. But it's like, when we think about our entry price, it's true. When we think about our entry price, do we think that we are able to three X that entry price within the next fundraising round? And so if the company says, hey, we're going to be at, are we going to go from one to ten million by the end of this year? And because of that, we're going to be able to raise at three 50. Great. Well, we're paying 70 for the A. I can totally see my three X there. Or it's like, well, actually we're only going from one to four because we're a slow enterprise sales cycle, but we're paying one 50 for this incredibly hot A. One to four, I'm not raising it 300 if that's the case.

AI assessment note: “I agree with that, that we have a very kind of clear litmus test”

Answered produced feed D 5 · C 5 · P 5 · Cm 4 4.85

Q well. The interesting thing will be they, will they continue to work for the next, you know, three to four years if in fact, you know, dollars get a little more scarce? I mean, how do you, I mean, how do you guys two guys think about those kind of, you know, whenever, how do you think about investing a company that logically only has four or five big customers?

A Specifically on the data labeling market, this is one where I've interviewed the founders of Turing, Scale, McCaw, Invisible. I've pretty much interviewed all of them. Surge, um, And the one thing that made me actually feel incredibly comfortable investing in the category was understanding the specialized data requirements that the large providers need. I hadn't quite thought about the very verticalized data requirements, whether it's surgical data, whether it's bookkeeping accounting data, that all of these different players are going so deep into, and it's so specific and in some cases strange and weird that the large Customers are never going to churn or pull away from them because they are so verticalized. And when I got comfortable with that, I was like, oh, I'm okay to take this risk and underwrite it because I don't think they're going to churn.

AI assessment note: “large Customers are never going to churn or pull away from them because they are so verticalized”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q where the rubber is going to start to meet the road, right? I think there is this assumption that from a, from a fund standpoint, not a company standpoint, we're always going to be able to raise. We have the brand. Investors are always asking to You know, get into our funds. I think that is the part of the cycle that we haven't gotten to, right? We haven't gotten.

A I don't think we're going to get there, Jammin. We're not going to get there. We're not going to, you're going to get there with a couple of shit ones, I admit. But you know, when you're looking at your Andreessen's, your general catalyst, your Lightspeed, I know you guys don't like to name names. I'm happy to. But, ah, like, you know, with these guys, as they scale, you just move into pension fund world, sovereign world, and they're looking at six, seven percent nets. And so these guys come in and say, hey, we'll give you 10, maybe 11%. And they go, ah, inshallah, take our money, take our money. And so, I don't think it does hit the road. And then you've got NASDAQ booming, and so their publics are looking better, and actually it offsets the denigration in private performance. I don't think it's gonna change.

AI assessment note: “I don't think we're going to get there, Jammin. We're not going to get there.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q more time to understand, has this been de-risked enough? Is this an appropriate time to lean in even more to actually do your pro rata or get more ownership? So that's kind of, kind of what I'd say. Ownership always matters, by the way, on these exits, particularly in a world of lower Uh, multiples, but you've got to be careful about with that, uh, how much you lean in.

A I take a different approach to pro rod and reserve some most people. And I think many LPs are shocked by this. I think actually it's often predicated on very misleading signals and immediate traction doesn't signify sustainability over the longterm. If I were to invest according to the signals, I would have put the most money into clubhouse hop in. Be real. They were like the outperformers within the first year of investing. They weren't the most sustainable. Sneak is not the most sustained, is not the most outperforming in that first year. And so I find most managers invest, observe for a year, and then double down on what's working. But what's working often is unsustainable, and it's your sneaks, your figmas, your big IDs, which actually may take a bit longer. But you wouldn't allocate to them if you were doing it on traction.

AI assessment note: “it's often predicated on very misleading signals and immediate traction doesn't signify sustainability”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q thought was like, oh, like, we'll talk to our friends that are, like, doing interesting things in AI, and it'd be fun to do a low-effort content project together, and, like, it has been fun, but, like, you would know, like, you know, one of the hardest-working people I've ever met, but it's, there's no such thing as anything that is, like, a high-quality, low-effort project, right? So, like, Duh.

A Yeah, it doesn't exist, but you can do fewer, and the hard thing is actually in the beginning, you need to do more. This is what people forget, like, you know, we did three a week when we started, I mean, we do three a week now, because I like the advertising revenue, but, um, like, it's really important to get those numbers out in the beginning. I remember, you know, Sarah, when we started, you know, the importance of reviews, um, that you really want to get reviews out, because it will pump you up in the organic download charts, because it'll put you higher and higher in the rankings, new and noteworthy, featured. I remember going with three friends to a football stadium, and having 500 Diet Coke cans strapped in, like, drinks, rucksacks, and saying, we'll give you a free Diet Coke, if you'll give us your phone for a review. And we spent, like, like, the 50 P each, so like, at 250 dollars, And we got 500 reviews. We were like number two behind the BBC in the UK.

AI assessment note: “Yeah, it doesn't exist, but you can do fewer”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Awesome. And you decided to make the jump yourself last year, and I have to ask, why did you decide it was the right time? And also, you know, why did you choose Atomico?

A Yeah, why the right time? I think the right time, my learning had slightly plateaued, in all honesty. I think the interviews were fine, and they were going as well as they had done before, but I didn't actually have a deeper understanding of venture, how raising funds worked, how LPs sort. And, and really what it takes to, to be internal within a fund, and be part of a team, and part of the investment decision making, and bring deals to the table. And so, I, I really wanted to learn that, and I thought it was the right time. You know, I was getting pretty old at that time. And so, I thought it was the right time, and I looked at London's landscape in all honesty. I think you'll probably agree, it's a, it's a shallow landscape, and they're clear winners to me. And very, very nicely, I was Offered a number of opportunities, and Atomica was by far the most exciting. I think it's got a phenomenal brand, one, and it's got a global brand, which is quite unlike maybe other European VCs. Um, and then you look at the team, you know, in all honesty, I met with you, I met with Siraj, I met with Alexis, and it was a case of, one, shit, these guys are really smart, and two, if Matthias can get this team together of incredible people, wow, I've got to be a part of that. Like, that's something special. If these guys are willing to give up their time for this mission, man, I've got to do the s…

AI assessment note: “I think the right time, my learning had slightly plateaued, in all honesty.”

Answered raw tape D 4 · C 5 · P 5 · Cm 5 4.70

Q froth in the private market for AI for two or three years. And probably the public market is saying, I'd like to get on, get in on the game. And this is one of the few ways to play it. So I agree. It's frothy. Is it more frothy than any of the things you're seeing or I'm seeing? I don't know. Who am I, who am I to judge?

A The one, the one thing I, I do think is important. We mentioned the margin element. I have never before seen such lack of investor diligence on anything except top line revenue growth. Ever. Astonishing. Where it's not included in updates, hundreds of millions of dollars wide, without a discussion on margin. Number one. And then number two, it's just like growth is amazing until it doesn't grow anymore. And when you look at this for OpenAI to pay this, if they two X between now and July, 26, and then two X again between July, 26 and 20, 27, they'll be at forty eight billion and still twelve billion short per year to do this. At some point, the growth does taper.

AI assessment note: “I have never before seen such lack of investor diligence on anything except top line revenue growth.”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q What do you think that, that thing is where you take it and make it positive and, and, and some people take it and make it negative. What, what is it you think that made you, was it, for example, supporting your mum? Was it an external factor you think? What was it?

A I, I think it was twofold. I think it was one, having a mentor that could actually redirect me in the right way. And I think it's two, the ability to end the day. And what I mean by the ability to end the day is like, When you have a shit day, go to bed knowing, my mother always quoted Scarlett O'Hara from Gone With The Wind, which is, tomorrow is another day. Do not let the prior day impact the next day. Always come at it with a fresh mind. I think the woe is me, one day will lead to another series of bad days, is very dangerous. Yeah, big, big lesson for me that I always think of is like, if you have the ability to be miserable for no reason, you also have the ability to be excited and optimistic for no reason. Embrace it.

AI assessment note: “I think it was twofold. I think it was one, having a mentor”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What do you, what do you suggest? I'm looking to you as the, you know, interim chief marketing officer at, uh, at Cognition.

A The thing I think that's nice with your product is actually that you fall into the Nike bucket. And what do I mean by the Nike bucket? The Nike bucket is that success was they make you feel like a superhero. They tell you that everyone is an athlete, that even if you don't have the skills, you are able to do things you never could before. And I think that you and Devon fall into that similar bucket of kind of human enhancement. Um, And so I think you should tell the stories of that much better, and then I think you should, bluntly, very clearly tell the story of your own growth much more deliberately. People want to be part of a rocket ship, and gossip is very vicious, and it happens when you don't shape the narrative yourself. If you shape the narrative, gossip doesn't really happen, because I can't say you're at twenty million in revenue when you're not, you're much higher. And so don't let other people shape your narrative for you.

AI assessment note: “I think you should tell the stories of that much better”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q We are. And, and yes, sure. Our, our CIOs adding an AI budget or this and that, but they're clear it's net zero. We've learned it's net zero at this point, right? Not an, so if you haven't, if you haven't pulled yourself out of now, I, you know, man, I mean, I don't mean to agree with Sam Lesson, but you might be utterly irrelevant. It's probably too late.

A I think it consistently goes back to one of Rory's most pressing statements, which is, are we able to transition labor budget into technology budget in the next wave of AI? And if we are, let's make, hey, markets are huge, and if not, then it's net zero. It's funny how I read it. I think the thing that I just think about is, like, being AI native is such an advantage. We are in a company that is similar to superhuman, uh, that will be at More than their revenue in nine months for what it took them eight years to go to. And that's no discredit to superhuman, just the benefits and the tailwinds that come from being AI first versus layering on is massive.

AI assessment note: “and if not, then it's net zero. It's funny how I read it.”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q to position yourself with for when they, when they do decide to raise. And, and, and then ultimately when they do decide to raise, being able to like reinforce that, like, hey, did I pick the right person to spend time with or not? Or am I just running away with this because I've spent so much time on it, which is a whole nother bias you have to manage.

A It's so funny. I have so many LPs who asked me this question, and I actually disagree with you on the picking element there. I don't think domain specialization particularly helps you pick. I think generational defining founders are quite obvious respectfully. That said, I think to your point, they choose you because you're the smartest. So it doesn't help you pick. It helps you win because they go Bucky, to your point, made me think about it in a different way. And Harry was super nice, but he didn't make me smarter. And he didn't know the market like Bucky did. And so totally to your point, it helps you win. Can I ask you one, do you even need to pick, my friend? You're now at light speed. You can just wait. I mean, part of me as a friend would say to you, just wait until the C, pay up like Vince did at Thrive for the, you know, thirty billion round, and ride it, baby.

AI assessment note: “I actually disagree with you on the picking element there.”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q literally. Uh, I mean, I've had two deals that were done in one day, like hot deals, and how do you get a deal done in one day, right? How do you guarantee you win? You check all the boxes. If you check so many boxes, there's even an argument the valuation doesn't even matter, right? At some level, because you've made, you've done, you've checked all the other boxes.

A This is, this is what worries me so much though with growth funds today is they assume that the outcomes are aqua, aqua probable in size. And what I mean by that is they're going, okay, I know X company is great and only worth two billion, but if I pay three billion, And I put in two hundred million. I know it's a ten billion company, so I'll get a little bit of a compression on my outcome size in terms of multiple, but it's a ten billion. What they don't understand is that if I stuff Rory with two hundred million before Rory's ready for two hundred million, that ten billion outcome size will be a four billion outcome size.

AI assessment note: “This is, this is what worries me so much though with growth funds today”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q are going to get, uh, see their values reduced. I think there's a lot that ultimately aren't going to be successful and go out of business. Um, and we haven't really had the wave of that happen yet. It feels like that's still to come. I don't know. I'd be interested in your perspective as a, you know, as a VC as well. How are, how are you seeing that?

A Well, I mean, I, I think, you know, the thing that we see from the data that we have, which is a lot, is the chasm in values that different people have in their books. I mean, just extraordinary chasms in value. I was looking at one today and one was valued at eight hundred million and the other person had it at 10.2 billion. That's a fair wedge of difference between the two. And so I, I feel for LPs because I think it's really difficult to get a fair grasp of what is the true value of your underlying book, and I think that's very hard. So, and I definitely agree with you, the managers who don't need to posture and present a brilliant facade don't need to.

AI assessment note: “the thing that we see from the data... is the chasm in values”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q where the rubber is going to start to meet the road, right? I think there is this assumption that from a, from a fund standpoint, not a company standpoint, we're always going to be able to raise. We have the brand. Investors are always asking to You know, get into our funds. I think that is the part of the cycle that we haven't gotten to, right? We haven't gotten.

A I don't think we're going to get there, Jammin. We're not going to get there. We're not going to, you're going to get there with a couple of shit ones, I admit. But you know, when you're looking at your Andreessen's, your general catalyst, your Lightspeed, I know you guys don't like to name names. I'm happy to. But, ah, like, you know, with these guys, as they scale, you just move into pension fund world, sovereign world, and they're looking at six, seven percent nets. And so these guys come in and say, hey, we'll give you 10, maybe 11%. And they go, ah, inshallah, take our money, take our money. And so, I don't think it does hit the road. And then you've got NASDAQ booming, and so their publics are looking better, and actually it offsets the denigration in private performance. I don't think it's gonna change.

AI assessment note: “I don't think we're going to get there, Jammin. We're not going to get there.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q So when you meet three, so you've got three. Um, what in your mind in those three, what are the odds you're going to do each deal? Like, what do you think? Are you already favorably disposed? Are you in the middle? Like where, where, how are you thinking about these three? Like where's the next stage of your funnel?

A Honestly, I don't like to preempt like how I'm going to do because then I think it positively sways it. I think the thing that I really try and resist is like this came from X person. So I'm 90% inclined. Like, yeah, I really try and go in with a fresh mind. I know that sounds kind of bullshit. But I really try not to be swayed and to go in without a, I'm positively or negatively inclined because I think the hardest thing as an investor is mental plasticity between deals. I've lost money in healthcare before. Doesn't mean all healthcare deals are crap. I've made money in enterprise before. It doesn't mean all enterprise is good. And so I really try and not be swayed positively or negatively. And I think that's very hard to do.

AI assessment note: “I don't like to preempt like how I'm going to do”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q want to have like X number of managers that look like you, We've invested in two or three of them, and so we have another, like, you know, four or five to go, right? Like whatever the numbers are. Um, so trying to get that, that feel, I think is really, really valuable. Um, and whatever questions it takes to answer that, I think is, is what you're looking for.

A I always ask about geography. I find if you're the first in a new geography, it's probably very unlikely. I always ask, like, on check size, like you said there about the ones that are massive checks, like, if they write twenty-five million dollar checks and you're raising a 30, forty million fund, you're pretty much qualified out straight away. I do check size, geography, existing portfolio for them, and then I always like to say, I think you can be quite bold in your fundraise, and so I always say, like, listen, I'm really optimizing for long-term partnerships, and I think trust is built over time. Can you talk to me about how you think about how you support your portfolio in the long term? And then if you're like, actually we take a case by case basis, you're like, oh, okay.

AI assessment note: “I always ask about geography... I do check size, geography, existing portfolio for them”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q there when things go, go, go, go negative. Um, but I think VCs can always, you know, opt out or, or be opportunistic to just focus on what's going well. And where they see value in their portfolio, where founders have this one shot at that moment in time that they need to get right. And I guess that's, that's a bit of a misalignment. How do you see it?

A Uh, I think around liquidity, um, is probably the biggest whereby, especially I think in the next years it'll be really prominent, which is whereby you have a venture funds with not a lot of DPI. And they know that they need DPI more than ever to raise their next funds. Uh, liquidity opportunities come about in secondaries, in sales, in PE sales. And actually, it is suboptimal for the founder to have them sell a large portion of secondary, or it's suboptimal for the founder to sell now, um, but the board absolutely want it, or the VCs absolutely want it. I think that's, to me, the biggest by far. Um, and so I think, I think that's the one I worry about, especially over the coming years.

AI assessment note: “I think around liquidity, um, is probably the biggest whereby”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q when he spent too much money. And, uh, but I would say the majority of the time I've had to be the ass kicker. The relationship is damaged permanently and not with the best ones, right? Not with the Algolias like we're talking about, but, uh, with more than I would have expected Harry. And is it worth it? I'm not sure. I'm not, I'm not sure it's worth it.

A I just want your thoughts. So when you go to an enterprise customer and you fucked up or the products, SSO is not working or whatever permission is not working. They're going to kick your fucking ass. And if you are a child and can't take that, well, you're not going to have very good enterprise division. You're going to have great engineers, great employees who are going to advise you on your leadership and how it could be improved. If you can't take that, you're not going to be a very good leader. So stop being like, help me. Like that's indicative that they just can't take feedback. And then, you know what? Fine. We'll point to anomalies like Steve jobs and Elon Musk, but predominantly, especially in B to B, That's actually just a sign of a bad leader.

AI assessment note: “That's actually just a sign of a bad leader.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q mind and be willing to say what, what your mind has on it. Um, you know, we, we can talk more about values later, but, but I think that, um, I think it's like fundamentally, the talent search algorithm is fundamentally like not that hard. People just get focused on the wrong stuff. Like, have, have you led a customer success team at scale before? Like, that's the wrong question.

A Okay. Can I, can I, and this is where, like, I used to remember I started when I was like, 1718, and so I just agreed with what everyone said because I didn't know anything. Um, you know, if I look now, I've built a media company over eight years. If you hired me as your CMO, say, I would know a lot because I've been doing it for eight years. If you hired someone fresh into marketing, they would have no idea about how to think about distribution, flywheels, channel by channel optimization, all of the hard yards that it's taken me eight years to learn. Same with sales, same with CS. Do you not think that experience has value in, in that way?

AI assessment note: “Do you not think that experience has value in, in that way?”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q will change. The product will definitely change. And to me, it's more, are they ambitious? Are they clear eyed? Do they believe in themselves and what they're doing? And, you know, sure, if they're going after a tiny market somewhere that doesn't make sense, and they're, they're totally, that's all they want to do, then maybe it's not the right investment. But in most cases, it's all about the founder.

A I get you. I, I have one learning recently, which is I lost money, um, on a deal, and it's because there were negative externalities associated with the market that could render the company bust, essentially. And now I take market first. Market is the single most important thing. If there are externalities that can kill a company that you can't control, no matter how good the founder is, it's not gonna work. And actually, when you think about, like, pivots, I know Twitter was a pivot from podcasting, obviously, to social network. But they're all in the realm of the same sector. They're all in the realm of a recruitment marketplace, a customer success solution. And so I'm like, actually, I've got to like the narrative direction of where this is going. You know, it's like the wave will change, but the tide is still the same. Do you know what I mean? Do you agree with that or are you still like, nah?

AI assessment note: “And now I take market first. Market is the single most important thing.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q the world, one of the most well-run businesses that, that I can see. I think they do. I think they've, I mean, back to like my, my, my, my five questions on enterprise value, like is arc of history in their favor? Absolutely. And it, and it, and it always has been. Will the world work in a way that's advantageous to them going forward? Yeah, I, I think absolutely.

A Do you agree? So I, I, I'm totally with you. I, I would have said the same. It's annoying because I often agree, and now I try and be more different. Um, uh, but, um, I, I agree, but I, I always think, like, success in venture is cyclical. Do you agree with that? It's like, you know, great firm gets great company, which leads to more great entrepreneurs wanting great company. It's this self-fulfilling flywheel, I often think, and I said that to Doug Leone when he was on the show, and brilliantly, humbly, he was like, huh, I would love that to happen, but people don't just go, oh, Doug, Here you go. Take my unicorn, future company. It's a fight.

AI assessment note: “I'm totally with you. I, I would have said the same.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q And what have you learned from those 70 or so people that you've been talking to? Are there a couple of sort of common trends or themes that come out from your discussions with not just venture capitalists, but angels and people working in the technology space?

A I mean, it's always a really interesting mix when you actually talk about the investments and what drives them. Um, cause you've got two clear strands of thinking within investing from what I've seen. You might correct me on this one, but it's people who believe in the team and the importance of the team and people who believe in the idea and the importance of the product. And those are the two that have really come out, uh, in terms of kind of really diverse strands. Um, I'm not, you know, it's an interesting one, and then also, obviously, the size of the market is always a massive player. You know, VC is all about finding that unicorn, the billion dollar company, so the market has to be really big enough, and that is always a uniting feature of all the VCs, definitely.

AI assessment note: “two clear strands of thinking within investing from what I've seen”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q That's good. So, you've spoken to a lot of venture capitalists, and you sort of spend a bit of time in these, in these buildings, um, and you sound pretty confident about its future. Do you think that's shared across the industry, and where does that, where does that sort of confidence come from?

A I think, I think it is shared across the industry. Um, you know, I've spoken to people at the NVCA, and we see that VC asset allocation is going, well, it's steady, and in some cases even going up, which I think is indicative of, um, a real future for the VC industry. So I, I'm extremely confident, um, and I think, I think so is the ecosystem. I think startups, there's a reason startups still go to venture firms and Funding, and it's because they are aware of what they bring to what other alternative methods of finance don't. Um, and so yeah, I'm inherently positive about it, and you know, I wouldn't be pursuing a career so savagely unless I thought it was a career of longevity and sustainable future.

AI assessment note: “I think it is shared across the industry. Um, you know, I've spoken”

Answered raw tape D 4 · C 5 · P 5 · Cm 4 4.55

Q are going to get, uh, see their values reduced. I think there's a lot that ultimately aren't going to be successful and go out of business. Um, and we haven't really had the wave of that happen yet. It feels like that's still to come. I don't know. I'd be interested in your perspective as a, you know, as a VC as well. How are, how are you seeing that?

A Well, I mean, I, I think, you know, the thing that we see from the data that we have, which is a lot, is the chasm in values that different people have in their books. I mean, just extraordinary chasms in value. I was looking at one today and one was valued at eight hundred million and the other person had it at 10.2 billion. That's a fair wedge of difference between the two. And so I, I feel for LPs because I think it's really difficult to get a fair grasp of what is the true value of your underlying book, and I think that's very hard. So, and I definitely agree with you, the managers who don't need to posture and present a brilliant facade don't need to.

AI assessment note: “chasm in values that different people have in their books”

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