56: Miles Grimshaw - Back Down the Mountain

27:43And I was probably 11 when she did this because we moved when I was 12. And she was saying, it'll be a lot of change and these are the exciting things. These will be the hard things, et cetera. This might be the school you could. I've never seen the school. I had no idea. And that unequivocally, as she finished telling me and thinking about it for me, I was like, we got to go. Let's go. Wow. I'm in. Wow. And she even said, I wrote a note to the tooth fairy. I guess, I forget you still lose teeth maybe at that age. I don't know. But I'd written a note to the tooth fairy that was like, I don't want any money.

28:20Just help my sister get into the school there.

28:22Miles Grimshaw:And I was like, really, really wanted to do it. More than I remember wanting to do it. And in high school, I actually went to the Himalayas in India for six months to a boarding school there, which I had a sort of uncle who's not an uncle. He's my dad's best friend, stepdad's best friend, who he founded a company with. And he was showing me pictures one summer of the school that he went to in the Himalayas in India. He grew up in India and he spent six years there. And I was like, I want to go there. And my mom is an enabler of this as well. She took it seriously, but I remember the history from there as, well, she kind of had it happen.

29:00And she's, again, recently told me because I'm learning about my own son and how determined he is on things he sets his mind to even at four and she goes oh no you were determined to go like you said we have to go and we got a curriculum change so the school would allow me to and all these things and so

29:19Miles Grimshaw:it's funny you have the things we remember in the yeah yeah and so I think that that embrace of a new adventure, the love of it. I often think it's a lot of fun, even though it's painful to learn new sports. You know, windsurfing, kite surfing, skiing, snowboarding. I've learned to do a little bit of a really weird sport. It's called alpine snowboarding, which is longboard, hard boot, like slalom racing, snowboarding. really fun for carving and it's really hard to figure out, no one does it on the mountain basically, but actually my dad did some of it and I saw him do it, I was like, I gotta learn that too and so I just...

30:06Are you comfortable?

30:07Miles Grimshaw:I kind of enjoy it, flying planes I kite surfed for the first time recently and the first three hours, you don't even get it to get on the board. Oh yeah, and just three hours, several days Are you comfortable? Most people don't like to suck are you just comfortable in sucking or are you like confident enough in your learning curve? It is absolutely right. Like it is the painful thing is being able to live in that place of sucking or not knowing. I'm getting dragged around on my face in the water with this kite. I just think it's really fun to figure out a new thing and to learn it. and I think this is where it's probably in the DNA but also I do think that, you know, that's the nature side.

30:57I do think there's a nurture side to it all and I think that the nurture side, the language for that that we all can share as a mental frame now is you kind of get reinforcement learning on the thing. So I have more probably more comfort with it and the reinforcement learning was I have experiences growing up where you ended up in a place that was really uncomfortable, that was totally new, where you totally sucked, and you figured it out, and that was a reward function, so to speak, that you go, okay.

31:30Miles Grimshaw:Yeah, my friend Jason says, I can do that again. Confidence is the memory of success. Great line. I'm going to steal that one. You've spoken in the past quite a bit about this kind of broad frame of companies, sort of the biological approach to companies and the idea of companies having genetics and durable genetics. Um, I think unlike a biologist or a sports scout, which you've made use of that metaphor to people seeing sort of Michael Jordan early on or whatever, um, your creatures aren't just adapting to an environment. They're adapting to an environment that is in like constant and rapid change, especially in the last couple of years.

32:08Miles Grimshaw:Um, so it's like two things are in major flux. And I guess I have a few questions on this note. First, what do you look for in genes that are durable across very dynamic environments? Meaning, are there any genes that are as true for companies as they were 10 years ago or 20 years ago as they are for this kind of new crazy era? It is an appropriate question given the rate of change that's happening. But the environment has never been changing like it is now. 100%. And I think that leads one to question every premise. And in many ways, one should question every premise because maybe things that we have normalized to the assumptions that drove that normalizations have changed.

32:56I think that there's aspects of building software, building software companies that were premised on certain assumptions, the core of which being that building software is hard, really hard, and maintaining software is even harder. And now that input, that truth has changed, things that we took as consequences of that without realizing they were premised on that assumption, we should reevaluate. And so I think it's an important moment to do that. And it's funny, because as you were saying that, I was thinking about a very good investor friend at another firm who, when we were just riffing and catching up the other day, basically said something along the lines of, I'm wondering if I should not be as precious as much about great businesses, business models.

33:46And so, very peak sentiment, but also the all bets are off and maybe it's just... So I think it's right today. That said, I think that there's a fundamental law still, which is you have to create more value than you capture and some version of a customer has to give a shit. And all the marketing mumbo jumbo, all the valuations or whatever that happens, at the end of the day, if you don't deliver something that creates a lot of value for an end user, an end buyer, that you can take a small share of, nothing else matters. Important parts. Most parts are important too. Yeah, yeah. And I have two silly but true questions that have become a bit of a meme at times at Thrive, which is, one, what is it?

34:41And two, who cares? Sometimes I say, who the fuck cares? And what is it is you can say a lot of words, but like what really is it? What is a customer really buying? What is the thing that it is doing for them? And two, like, who cares? Who is that customer? Who is that user? Who is that person on the other end? Who's it for? And I think that those two are like really important to ground oneself in. And I think that I do wonder, in any cycle, I think, you can take the wrong lessons from the successful companies. And so I think Google did a hilarious thing for a bunch of teams, which is Google was so successful in the core thing.

35:37that in some sense, no matter what they did next, didn't really matter, that they then espoused, and so people tried to copy them for this idea of 20 % time, which was, oh, you can have 20 % of your time to do creative things, which did both Gmail and a bunch of other things.

35:54Miles Grimshaw:Also the best business model in the history of the world. The best business model in the history of the world to do it with. But the corollary to where I framed that is, oh, you can only work four days a week. That's what 20 % time really means. Yes, yes, yes. Nowadays, no one works five days a week. They work more, but like, you know, whatever, simple things. And in some sense, it was the wrong thing to learn the lesson of from that company. And, you know, another version of that for SaaS for a little bit was like every software company's revenue is 10x ARR. Just is, like, not true. All revenues created equal, not true.

36:32And then I think for this one, we call them labs. And they are very commercial entities. And Sam is an extremely, incredibly product-minded leader. Sam has great sensibility for products and customer demand and value to customers. and calling them labs belies that product-mindedness, that customer-centricity. And I think that some are learning the wrong, in some sense, a bit of the wrong lessons from that. And the cursor lesson is a better lesson to learn, which is like a relentless focus on delivering an incredible product that will, for a long time, sell itself. You know, we had a very small sales team until the beginning of 2026 this year.

37:28When I first started working with Michael, they were passing many single digits and rapidly, you know, tens of millions in ARR. And they had zero salespeople. And Michael was relentless on, you know, his own team's feedback on that product. They are the customer of the product. And individual end user conversations versus just sales. They have very strong purity to delivering a great product. And I think that that is a truth that you can never lose sight of. And if you ground yourself in that, good things will happen. When it comes to these sort of outliers, especially with the sort of good genes frame, I think one of the most interesting bits of thinking behind the genes frame is that, as

38:25Miles Grimshaw:you also said, that the house cat kitten and the tiger kitten, they kind of look the same early on. There are lots of companies with crazy exponential growth really, really early on. And I think what you seem to be quite good at is identifying which ones have the genes that can go the distance and which ones don't. In the case of the truly, truly outlier companies, as you sort of implied in your previous answer, they sort of defy categorization. And so I'm curious how you think about sort of like, assuming they maybe get those couple of main things, right? Which is like, I know what this thing roughly is, and I know who it's serving.

39:04Miles Grimshaw:How do you think about sort of like being willing to sort of slot some frame on what a good gene is and also tolerate something that like looks like something you've never seen before? Because definitionally, I don't know, I think you've written or spoken in the past about a company like SpaceX or a company like Shopify, like what even is it? It's got a bunch of these different products. How do you identify a gene that you have no prior evidence for its success of? Part of the big part of the sort of genetic lens to it is whether it's early stage or, you know, what people would call growth stage, which we still think about as being early for that company when we're doing growth.

39:47Whatever is measured today is visible today, the product on a spreadsheet or whatever, is a fraction of what should be to come. And it's all backwards looking by and large, like not forward looking. And one is trying to ponder what the genetics of this are so that, you know, at age, so to speak, you know, Michael Jordan being young or whatever, like what does that become? The kitten and the, you know, tiger, you know, when they're both small cats, you know, which one becomes fierce?

40:28Miles Grimshaw:We know what a tiger looks like and we know what a great NBA player looks like. Whereas we don't really know what a - Yeah. And so you're pondering that. So what will that be the full expression of that? I never pondered through the lens of it will be some other thing. It's like, what is its version? What sort of traits does it have that are outlier? What does it have? And eventually those would map to like common business principles, which is it can have high earnings power. Right, but even common business principles. Back to the basics. It will have high earnings power. in a large market. But it's probably not fully expressing that right now.

41:17Rarely is that probably the case. And so I think there are two aspects to that that I think about. One is these are led by a person, and a person is making decisions. Every marginal decision about this company and what it does and the tradeoffs that it faces, And so I think a big part of that is like, where is this person looking? And you can have similar things in different people. They can look the same today and sort of phenotypic expression, which is to say, you know, what you see in the organism, in the company, but they can be looking at very different things, which is to say they're very different genetics.

41:57And I think you can take, you know, Stripe and Braintree. Early on, kind of looked the same, but you talk with someone like Patrick Collison, and he might not have had the words right then, but he kind of has the framing of GDP of the internet. And that will be expansive in nature. And what they have done so far is like a tiny fragment of where they're looking. And so early on, the question is, the job to figure out is like, where's that person looking? Because eventually, in driving and biking, you go where you look.

42:33Miles Grimshaw:Right? Any sport you're learning, the thing you learn is look where you want to go. And I think it's really true for companies too. It's like you go where you're looking. And I think that is a key aspect of it. And so you might see only a bit of it, but where's that founder looking? You know, take, again, to come back to it, Michael of Corsa. When I did an early dinner with him before, just, I don't know, two weeks before we invested, we had a conversation. uh he wasn't looking at the ide he was looking at abstractions of coding making coding easier the ide was the manifestation of it today but he wasn't looking at that he was looking over there um and i think that that is a really important part and the other element that it applies to sort of what's the nature of this product with its customers and the value created and the value kind of capture and the genetics of that.

43:31And many people will look at, you know, an AR.

43:34Miles Grimshaw:Sort of like business model fit? It's sort of almost, if you want to try and put in something, it's like the unit economics. But not economics, unit economic singular version of a customer value proposition in a way and the nature of that. if eventually the companies we work with hopefully are very scalable. And scalability comes from repeatability. And repeatability is that one thing a lot of times. And so what's the nature of that one thing? And how repeatable is it? What's that nature of that one thing? And so many people go like, oh, what's the ARR growth? That's a big thing these days. Oh, how fast was I to 10?

44:13How fast was I to 100 ARR growth? I kind of don't care. that's sort of a phenotypic expression of an end set of genetics and the question is what are those if you have one customer that you suddenly sign or let's say let's be more realistic you have three customers you sign for 50 million dollars a piece and so you're going to say that you're you know 50 million of ARR basically that's just a very different set of genetics than I have you know uh 500 ,000 customers at a hundred dollars a piece I'm not saying one's better or worse I'm I'm not trying to, that's not the question of that. They're just really different.

44:51And the question isn't, which is better or worse? It's where are you looking and what does that, what can that repeated in some sense and evolved become?

45:00Miles Grimshaw:How durable is that to changing the environment and all these other things? And you need to kind of be in some sense an analytical dreamer to this. And so come back to Kirsten on this and you're asking which ones are gonna be, Michael Jordan versus good college basketball player. It wasn't, hey, what's an IDE worth? If you look at the IDE market and you said, what are the genetics of this IDE kind of thing? It's a terrible market. It's mostly free, VS Studio. And the company that had done the best on it, JetBrains, maybe made a couple hundred, like 200 maybe million of revenue, I forget. It's not.

45:37It's not a business you want to be in. But if you get more first principles, about it, you go, what if intelligence is at the core of that idea? And that is a scalable thing that you consume through that idea or through the product manifestation that that eventually becomes because the idea is only one such today's manifestation. You actually now may be a product that has$1 ,000. It's now actually like$10 ,000 of value consumption in that experience. If you said, well, I'm going to take what the world has, that the world has had evolved to so far, the ID market, that's a 200 million. Naturally, because the value of the product can only do so much for you.

46:28But when that product is now like the consumption of intelligence and is supercharging it, we literally put on a piece of paper, we think that could be thousands of dollars, which is definitely undershooting it, of user value. and monetization in that form factor. And so the dream, it's sort of dreaming something new. What is its unique version with a thinking on almost those atomic units with where's that founder looking? Do you think,

47:01Miles Grimshaw:this maybe is a can of worms, but at the time you made the cursor investment, it was probably an implausible conception. But let's say somebody was really thoughtful and they were able to sort of pull forward the conception of something like cloud code hitting the market. It seems conceivable to me that they would be able to make an argument using this sort of frame that says like vertical providers who make the models themselves. And maybe in the end, you could even make the case, I don't know enough to say, I think it makes sense that Cursor teamed up with a big lab in some sense. How important is it to sort of see the end case business model fit versus just project forward like enough potential?

47:41Miles Grimshaw:like are you going to pay for cursor with seats are you going to pay per token like maybe i'm getting caught up on how important it is to specifically see the the sort of unit economic trade there but presumably cursor's business model in a year or two or three might be different than it is now yeah so that's why this is so hard yeah you have to be willing to have confidence in that uncertainty versus trying to have like a deterministic view of it. I think certainly for early stage and even early growth stage, the question, the interesting question, I said this to a candidate I was interviewing once, I was like, I don't need you to tell me more ways this can go wrong.

48:26There's infinite ways this can go wrong that I can enumerate you. Our job is to figure out the one, the path of it going right. And what if it went really right? And if that's not implausible, and if we think this is the unique company for its confluence of factors to get to do that, let's go help make that happen. Not because we know it's a sure thing, but because we want to try and do our best to help make it as sure a thing as we possibly can. and in in in that case the models at that point in time were not good enough yeah to do it all yeah you needed a lot of human oversight and so no question the thing to deliver value on you know for the foreseeable at that point in time future was an inter it was a coupling of the product experience for for the human experience with more and more and more intelligence you know evolving from better autocomplete to then better pseudocode to then better code review.

49:34It was all this stuff that they were very creatively doing and actually doing their own model development for. People forget this, but Cursor's tab model was their own. And so they were full stack from the get-go, from very early on. And obviously, the labs have done incredibly well as the models have gotten a lot better. but the view which Curs is still certainly proving out of the product model combination to unleash the maximum of that intelligence and the team that cared and thought a lot about the craft and the science of the model but the craft of the product in that intersection

50:15Miles Grimshaw:just for that holistic coding experience which was not just an idea it was never where Michael was looking he was looking at code review He was looking at a whole other aspects of the whole software development supply chain to make building software easier. Is a pursuit worth pursuing? And they were at a kind of continuing way in the game. Which is... Exactly. You learn. The other thing I think a lot about to the genetics metaphor is these companies are sort of evolving entities. What are the genetic pressures that are happening? What are the market forces, customers you pick are pressurizing functions for your adaptation?

51:15and being in the game, having great customers like they did early on, like Shopify, like OpenAI was a big customer early on. NVIDIA is one of our biggest customers is incredible adaptive, you know, pressurizing forces. Not theory. For adaptation of like, what do they want? And those are back to the point of not all ARR early on is created equal. It's not about just that number. It's about the genetics. I care far more that you've selected and are working with really thoughtful, avant-garde, demanding customers than just your revenue. Because those are pressurizing functions for you to adapt your fitness, your product, your organization, et cetera, to be well adapted to the most demanding future.

52:08And it's not about the revenue early on. it's about that adapt that adaption to the best version of of what it can be and the best customers like force that and so you know stripe early on you know i think stripe would be a very different company if delta was its first customer not shopify right or left how do you how would you advise a let's say a series a company who's like quote unquote found something like product market

52:41Miles Grimshaw:that they're early on, they're maybe not working with their first customer or two, but they're early. Like how would you advise putting, choosing, like what is choosing a good customer? I mean, obviously it depends so much on the company and the business, but roughly what is choosing a good customer mean? It sounds like maybe a young company that's moving fast, but what else?

53:02What customer will best help you live in the future?

53:08Miles Grimshaw:Of your market. of your market, of your product, of the value you hope to create, of the problems you hope to solve. Yeah, yeah, yeah. And some customer of yours is. Who is that? And don't pick the customer for the ARR. Yeah. Don't pick, at some point you do need oxygen. Yeah, yeah. You just need to have some momentum. We have venture capital for that. So, you know, you need some momentum. And so, you know, there's no strict rule ever. Yeah. But you need customers that help you live in the future. Lyft, I think, was an amazing one. Shopify was an amazing one for Stripe for that. The complexity of their money movement.

53:46Miles Grimshaw:There was actually a leading indicator of how the rest of them - Scale and other things. The complexity of Shopify scale pressurizes, is a company that's willing to take the risk. It's not Amazon taking the risk on you. Very hard to do. It's Shopify taking the risk on you. But the scale and their growth and their demands and their Black Fridays and their - Yeah, that's cool. is superb pressure. And Toby is a developer's developer. And so you know he's going to be understanding and pressurizing. So it's not just like the nature of their business. It's like, who's the person on the other end? And what are they going to be doing?

54:25I want to speak a little bit about the sort of broad sense

54:31Miles Grimshaw:that software, venture-backed software companies are, were certainly one of the most amazing places you could invest money over the last 15 years and where you have spent the vast majority of your time. And a lot of that is being called into question. Maybe a first cut in based on what we were just speaking about would be, have you started to develop a sense of what types of genes are most adapted for this kind of crazy new world and which ones that maybe were previously strong that are now maybe like, I mean, we spoke about it briefly. Like one kind of super obvious thing is we have a thing that used to be scarce that is no longer, which is making software at all.

55:16You have to be questioning of it because that fundamental input has changed. And I think that... Thank you. And people talk about the moats, well, actually, they talk less about the moats of software companies. They tended to talk about the spreadsheetification of software companies. They have all these fancy numbers like magic number and rule of 40 and all these other things. For why a great company was valuable, the sort of visual metaphor I think about a lot of times for explaining some of it is that in many ways, the great software companies basically built a city. and software was hard to do.

55:54And so your wall clock time, it's like just assuming you put resources in there, the wall clock time of having to build this up, you built up this whole like ecosystem of this city. You're banning off and you're building a CRM. Sure, you're building a CRM, but you're kind of building like the city of sales in many ways. And there's an economics term called the agglomeration effect, which is used to describe like why all the butchers are on the same street because it makes no sense that butchers would all be you know or bakers would all be on the same street because you can very easily go to the other baker and get bread from them instead and so wouldn't bakers want to be separate in parts of the city so that if i went there i only went there and i was going to that one versus i could easily walk next door and go to the other one but it's actually rational for everyone who's bake you know they're going to be in the same street because the demand is You're gonna aggregate.

56:46And so theoretically competition is easier, but actually everyone does better with it all there. And I think as a software company, you're kind of building like this city. And yeah, you had clear modes of switching costs and other things. Occasionally you got a network effect business, but it's very rare in software. I think you got a lot of like agglomeration effect and wall clock time. If your city had more people that did that thing in it.

57:12Miles Grimshaw:There's even a mind share element. Mind share element. And if an alien comes down on the planet Earth and is doing sales, they look at the map, they go to Sales City. And it kind of all just went there. And the moat was the wall clock time, which was just the sheer hours that had been put in building that software empire around that thing, building that city around that thing. and what's challenging about what's happened in AI for software is the wall clock time's kind of gotten eliminated. And so you can kind of build that city. You might not have any residents yet, but you can build that city.

57:56Miles Grimshaw:If it took a day to build a city, we'd have more cities for sure. We'd have more cities. And so I think that software though is still going to be really useful. We're going to use way more software. in the future. In some sense, I think the future-oriented lens is to maybe think a little bit about what happened in e-commerce and commerce as a function of the internet and to think about where software might go. We're going to do a lot more transactions. E-commerce - Maybe media as well. Maybe media as well. But in the commerce, I think we're going to consume a lot more things. We're going to buy a lot more things.

58:33Commerce grew, but the nature of it changed. And this is where the city analogy almost bridges, I think, the two in a little bit, which is you could be Radio City or Bed Bath & Beyond or Staples or Blockbuster in the offline, no internet world. because you picked the top 50, top 30 metros in America and you had one or two stores depending on them. And if you'd built Radio City in that city and you're running it well and you're giving value back to customers and being competitive on prices and what have you, like you kind of, why would anyone else start? You had sort of like this wall clock time and cornered resource of the whole thing and that's where it goes.

59:19And so why does anyone else come in? That changed and you couldn't be a specialized retailer you know mid-market retailer for a thing anymore you had to be amazon just like you got really big walmart you got really big or you're like luxury you're lvmh and i think that uh there's been a lot of like radio city bed bath and beyond of software so to speak and i think you're going to need to do a lot because the wall clock time changed you should have way more surface area you should cover way more. You'll make less margin on it all. I make one buying decision.

59:58Miles Grimshaw:But I appreciate it. And you see that in security and some of these other areas that have trended in that direction. I think it'll get way amplified. Or maybe even Salesforce. Salesforce. But you need to put intelligence at the center. You need to totally re-imagine that, too, for the modern age. And in some ways, the retail analogy holds here. The way you thought of retailing had to change, too. Amazon merchandises everything. Radio City picks merchandising thoughtfully. where it puts it in the store mass. This, I merchandise everything. And so it's how I think about supply chain changes. Here, I actually have real working capital issues for staff stocking inventory on shelves and radio city.

1:00:37In e-commerce land, I have no working capital issues. I sell it before I go, I have to pay for it. Negative working capital. So the whole nature of the thing changes. I think the same is true for putting intelligence in the thing. But there's a version of I need to do a lot in my industry, even more so than I ever thought of before, and be that. or I'm some version of a luxury. I'd be scared of saying anything about this company in some sense, because I'm not sure how he thinks about it. But I have a ton of respect for Palantir and obviously they're doing remarkably well. In some sense, maybe they're, you know, luxury.

1:01:12They're like, we're here to help you. And they are the original forward deployed engineers. It's only a forward deployed engineers if it's from the Champaign region of Palantir. Like they're their OGs of engaging with you on it and building it bespoke. Got it, got it, got it. And this mid version of things in software, you would never build bespoke. Building bespoke, if you did that, was a minefield because the maintenance on all of that over the years ahead was going to be brutal. You're going to end up running so many versions of it. But that assumption suddenly changed. I actually think more companies now should say yes to one customer's needed feature.

1:01:59And if you, A, can't get that ship fast, you're probably not using the tools totally effectively. And B, if maintaining that slight version of that N of one feature is a minefield for you, your code base is probably not, your architecture and your decision-making is probably not adapted to literally the ephemerality, disposability, ease of building software. And so I think they might be one of the best ideas I have so far of the other barbell of what could happen if you learn from commerce.

1:02:31Miles Grimshaw:In this sort of luxury frame, or maybe a white glove feels almost even more fit, like what is durable about that? It's just the fact that like, yeah, sure, I could build it myself, but like these guys do it well. They meet our needs really quickly, maybe more broadly. Like what will the actual moats of software businesses be in the end? It's just like, oh, yeah, like to build something at the scale of Salesforce or Amazon would be too much time. And maybe within all this, presumably margins compress. Will there be areas of software where you still have really high margins? I think this can have really high margins.

1:03:10Miles Grimshaw:Okay, the white glove. Yeah, I think there's enormous value that can be just, we're going to consume, we're all going to consume enormous amounts of software, way more than before. Yeah, yeah. Again, like media. Maybe that's the place where - Yeah, yeah, yeah. YouTube consumption versus, yeah. Yeah, it's going to grow massively. And you have millions of creators, but you don't have three mega studio cable network, whatever. And the value created from that is going to be even bigger because you now have - In aggregate. The end result to customers of value created, I think, is going to be enormous.

1:03:45Yes, yes. And that's the ceiling of it all.

1:03:46Miles Grimshaw:Totally. Right? The ceiling of any market - Totally. Is in value customer created. and that with intelligence where it evolved from software that can help you do work to software that can do work, software that helped you make decisions to software that can make decisions, software that helped you coordinate to software that planned and did it, you know, is enormous. And so we're going to consume a lot more and the value from all of it is going to be a lot higher. And that's the umbrella ceiling of it all. And I think someone, you know, like Palantino and like others that will come about are going to create enormous amounts of value and make that very easy, make that very bespoke and make it very curated, custom, tailored to that business.

1:04:35And they're going to get paid very well for that because they're going to create a ton of value. And there will be switching costs to it, you know, that will exist somewhat. There will be trust that will be really valuable as part of that. There will be know-how and knowledge that's sort of imbued in that whole thing that's really valuable and the like.

1:04:54Miles Grimshaw:But you mentioned selling work. In a world where you go from selling products and tools to selling work, do you think there's still place for this software with great craft and with great artistry? Or does that not really apply in a services context? I think it does. I think it really does. The reason I think that values, I really like how Patrick Collison said this once. We're paraphrasing. He said, the reason you should care about craft and attention to detail is that your customers, instead of seeing and feeling that, will trust you more because they'll know that you really paid attention. And so I can't rationally say that one bottom being more beautiful or that one whatever being better.

1:05:44but without maybe knowing that thing, you have a sense of that as a customer. You can also just tell - And that imbues trust where, I'm going to trust a lot of the other stuff.

1:05:54Miles Grimshaw:Seems like they know what they're doing here. Seems like they know what they're doing. And I actually think interior design is an amazing area to develop that as a lay person. You just go through spaces and they feel so different. And developing the perception of that and the ability to sort of see that down to the level of like, what are the switches or plugs that someone chooses to have in a building and in a room, you know, like tell you a lot, like a human being made every single decision around you. Especially in our abundant AI. Yeah. And how intentional were those decisions? And so one, I think I love it because you become more aware of detail in the world.

1:06:35And so I kind of like the craft for just, again, that love of learning and the pursuit of more understanding and awareness. As a total aside in the interior design, I remember feeling like I had no sense of that, and I've tried to work on it in Hone, and I was looking at some couches once, and I sent it to a friend. I was like, what do you think? They're like, well, I don't like the legs on that one, on that couch. I was like, I hadn't even looked at the legs. You don't even see it. After that point, I was way more aware of different legs and the feeling that they gave you between modern to mid-century.

1:07:04and the like. Anyway, do I think that is still true in a world where you're maybe consuming less of a digital interface as we know it today? I think so in the same way that you work with people who you know have more attention to detail, who you know have more thoughtfulness to it, who you know have more dynamic range to - The way they are is craft in a way. The way we are is absolutely a craft. and so I think that will still remain true.

1:07:38Miles Grimshaw:When it comes to actually investing in software, you've done it a little bit, granted mostly through a software lens, but you started to do more in bio too. It sounds like at least as a firm, or certainly as a firm, Thrive is continuing to do a wide range of things. As a career software investor, are you expecting to have to do serious reinvention? Are you like, man, I got to start investing in atoms now? How are you thinking about software broadly as a kind of category, or let's call it the next three years, five years, asked very sort of crudely and without nuance, like, is software over? I don't think, again, I don't think so, to our point of like, we're going to consume a lot, we're going to have a lot more in our lives.

1:08:19Miles Grimshaw:Yeah, through a venture investor context. Yeah. Well, I don't think so, in part because there's a high rate of change right now. Yeah. And change is the oxygen for new companies to get formed because incumbents are caught off guard or incumbents don't serve something. Well, there's a new demand. There's a new infinite game to be played, to build for, to invent for that exists. And so change is, why is there such entrepreneurial zeal right now? Because there was change and change is the oxygen for new teams. um i i love software i just think it's amazing that you know in your dorm room so to speak you can build something where no one can stop you where you don't have to have been insane amounts of pedigreed whatever or no special people or whatever no one no one can there's no gatekeeper you can go build it and if you build something valuable in the world it has zero costs of replication and people can benefit from it.

1:09:28It is a magical thing. I hope that I will not be labeled as a software investor, but rather someone who was a great partner to visionaries achieving their dreams. And a great partner to that when they started small and were not much to really big. And again, that going back down the mountain and finding that, even if it's in different areas, is the joy. And it happens to have manifested so far more through software because it's an amazing medium for that. CUS was a joy of that in many ways. It was like four MIT 20-year-olds who were going up against Microsoft. And I love, I live for the story of the four 20-year-olds who went up against Microsoft in their like bread and butter developer IDE mainline pursuit.

1:10:33Yeah. And did it better and created amazing magic for the world. From that, you know, one of the ones I was most proud of before was working with Tom Blomfield who founded Monzo. You know, he went and said, we could build a better bank in the UK. And that is a nuts thing to say. It was all digital, you know, there's no atoms per se, but like, you know, it's a real world thing. And I think something like a tenth of the UK population like has it as a daily checking account. Like it was a big bank in the UK. And that's awesome.

1:11:13Miles Grimshaw:A few other questions about investing. how does intuition play a role in what you do?

1:11:23Miles Grimshaw:If at all.

1:11:29It's an interesting question because I think over time, I've learned to trust it more. Early on, you know, that gets sort of like the adage, if I had more time, I would have written you a shorter letter. I think early on, you both don't know a lot, you don't know what you don't know, and you definitely don't know how to weigh things. No one should trust you to really weigh any of the factors. If you're lucky, you can lay out all the factors, but oftentimes you have to start by learning what all the factors might be. To my point earlier, you can tell me a thousand ways this can fail. Laying it all out.

1:12:07And then over time, the ability to weigh those is, I think, reinforcement learning in some sense to become good at feeling those. It's gradient descent your way. It's feel, yes. Yeah, gradient descent your way to that. And without some reps, I don't know that you should, you might have the intuition, the intuition might not be right, but I think to get confidence in it for myself, the gradient descent has been important versus trying to be analytical, purely analytical about it. and so it might now align with a lot of my what was my instinct or gut along the way but also you develop more feel for it it's important and I also think to be a productive team member you need to find ways to communicate that instinct yes because I if my partners our team doesn't see something that I see I don't think it's a failure on them I think it's a failure on me because I haven't been able to communicate what I see here as the potential and what's exciting.

1:13:12And if I can't communicate it to the people who trust me the most, who believe in me the most, who know I'm telling the truth, but more than anyone, like how is the rest of the world going to do that? And so like, I have to be able to not just have instinct, but be able to communicate instinct in a way that is legible to our team because otherwise it won't be legible to the world. It's not going to be constructive. And so I've learned to trust that in a way that hopefully can articulate that as well more and more as time has gone on. And I think another aspect of trusting that instinct and leaning into that instinct is, well, I'm biased because this is my view, but I don't know that as humans we're very good at like an absolute perspective on things per se.

1:14:03They may be the very mathy things we are because we can say 10 is greater than 9 and there's rules. But I think in a lot of it, we are far more relative beings. And you need to have been aware of and have a sense of what true greatness is to be calibrated. And I think I feel very lucky in my journey along the way and in Thrive and the teams we've worked with to have been able to work with and have a sense of some of the very, very best, the very, very best. And I think one of the hardest things, if you don't have that, is knowing just how great, great is. And once you do have that, I think it becomes a lot clearer to see that and understand that and have instinct for that.

1:14:55And so the more I've had the fortune of that awareness, the more I also have come to trust instinct. There was actually a team we were fortunate to work with called Mesh Optical that we've partnered with adding corporation. They'd just left SpaceX, three people who'd left SpaceX who'd worked on the laser interconnect for Starlink so that all the sats could communicate data across each other. and we met them basically the week they left through a relationship that was a founder who I never backed but deeply respected and admired and tried to be friendly and a resource for. I think that some of the best young people recruiting out there and we'd stayed very close to that because I deeply admired him.

1:15:52I struggled to get conviction in the product and the company he was building, but like he was a star. So we stayed very close and he was very kind enough to me. This is the, something also I try to hold myself to is who, who has introduced me to things, even if we don't work together and, and try and have that be a great experience. You put just positive, positive out there in the world. Anyway, introduced me to first week they've just left. I do that first meeting with them. It's, you know, Friday afternoon and it hits you in that meeting. they are incredibly authentic they want to build lasers they love building lasers laser interconnect now they want to do optical transceivers for data centers which is lasers it was part of a bigger vision of photonics manufacturing that's where they're looking uh you can tell that they have been very aware of the water that they've been in at spacex and so they're thought about sort of leadership and culture even if they've not honed the words per se for it they've been very aware of the water that they've been in which means they'll be leaders because it's not just to come the product, you got to build a company and lead the company.

1:16:53So you go, wow, on that. So that was a Friday afternoon. Saturday morning, we see them. Sunday afternoon of a long weekend, we have a team call where they pitch the whole investment team. And by Monday morning, we'd agreed to work together in an area, optical transceivers, that we had no business knowing anything about. absolutely zero business knowing anything. But that was instinct and felt confident. And you've always got to be checking your confidence on that because you can get complacent and you can get off tilt over time, potentially on it. You get the wrong exposure. But I think I would personally not have had the confidence to do that five years ago.

1:17:39Yeah, yeah. But the exposure to great people and even what those look like very early and enough of a sense of what a good business can be, so to speak, and thoughtfulness about that and pragmatism around that, not just intellectualism about that, gave us the confidence to do that in two days. And Monday was a holiday and most people would have had partner pitches on a Tuesday and it was all done. That's a great answer.

1:18:08Miles Grimshaw:you've been described to me as being elite at getting up to speed on a domain incredibly quickly and specifically the orientation of like who's like the SEAL team group of people I should meet I don't know if it's five or ten or whatever like as I'm kind of like first kind of like learning a new domain can you speak a little bit about that maybe this goes back to what we were talking about at the very beginning of the conversation which is like I'm going to go learn about whatever probably early on some of this AI stuff or lasers or games or whatever it might be. Like when it comes to like, I don't really know this.

1:18:41Miles Grimshaw:I've got a week or two to kind of crash course. How do you think about that?

1:18:47I think the three most important words for an investor, I don't know. And I think that an investment team and organization that can't say those words to each other is a very dangerous one. And I've thought that for a long time, almost from first principles, I guess. But it was great. I was with a terrific public market investor who had worked for a decade under an extremely esteemed public investor, the sort of investor who has books that are sold out and you have to find deep in the libraries. and he had said, I was asking him questions of working for that person, lessons learned for that person, what that person looked for in people.

1:19:40And he said when he'd interview, when that very esteemed older investor would interview people, he'd give a case study or whatever and then you do a chat on the case and the investment opportunity and you'd just be riffing. And the investor would love going through different areas of it. And the main thing he was looking for was at some point you'd say, I don't know. And he was like, he might go, okay, imagine if we spun out that asset from that company. What would the tax consequences be in the three major jurisdictions it was sold? And if you didn't say, I don't fucking know, let's talk to the tax person, like wrong answer.

1:20:20And I think it's like really important to be able to say, I don't know. And the four really powerful words after that are, I'll figure it out. and a willingness to go try and figure it out. And one, I guess it's interesting you said a week or something. I've never thought of giving myself a clock on it. Sometimes there is a clock of a decision. If we don't get to a place where we feel like we know enough,

1:20:47Miles Grimshaw:you can't make the decision. Yeah. And so learning is like a continuous game in that regard. I think when endeavoring on that I I found that people can get very uncomfortable in those conversations where you're trying to learn something also in those moments so I didn't understand that and I'm just I will preface things I'll say hey I'm really naive here can you help me can you explain this or let me play that back to you I'm thinking, can I analogize it this way? And they worry about that because as you get, as you have some success, you're meant to be really smart. You're meant to know it all.

1:21:34You're meant to, and to walk into areas where you don't and be willing to be vulnerable and say, sorry, I just don't understand that. And kind of try and get to ground truth versus accept people's high level responses or marketing oriented responses versus get a bottoms up understanding is I think one has to kind of, in some sense have a lot of ego because they're saying, I'm going to figure it out. But in some sense be very low ego about it. And that's the disposition I have towards it all.

1:22:12Miles Grimshaw:Obviously a huge part of at least the type of investing you do is being a board member. And so I guess I'm interested in that potentially, but I think the thing I'm most interested in is any advice or thoughts you have on helping companies close great people. Because as I understand, that's kind of actually one of the, when it comes to like, what do VCs actually do? One of the things that you really actually provide a ton of value with. It's kind of, kind of someone has said that. I think that it starts with making investments and committing to teams that you believe in. Like everyone can tell if you're selling something that you don't believe in.

1:22:58Which is why I think that word choices matter. And when we invest, we make a commitment. We don't make a bet.

1:23:09Miles Grimshaw:This is not just a bet. This is not, hey, we put some chips down on a roulette table and one in 10 times it turns up positive or whatever. It's like, no, we made a commitment because we really believe in this and we're committed to helping this company, this organization be the best version of itself and succeed as big as it can. And we stand for that. And so I think in some sense, selling starts before you get on the call. And it starts with, do you know in that and other people knowing that you stand for that. And then I think, again, I said to you earlier in this conversation, the gut question I always ask myself is, can I imagine recruiting for this?

1:23:53I've done a lot of those calls. Not as many as founders do, obviously, but it's a core thing.

1:24:02And that is, when you do those, also being able to be honest about it. And so, you know, it doesn't mean you sugarcoat everything. It doesn't mean you don't acknowledge, like, risk to it all. But you're... And then three, I think one is helping a candidate make... At the end of the day, make the right decision for themselves. If they join somewhere that they weren't really a fit for or that doesn't really match to them, it's actually really unproductive. Because now the CEO and the leadership team has got a management challenge on their hands. They're going to have to move on from that person.

1:24:34Another person is going to opt to leave in a short amount of time. And so it's better to have a fit than a person as well. And so I do approach it a lot from what is this person's goal? Where is this? What should they be doing? Yeah, I guess. And coming back to what I said about the CEO, where are they looking?

1:24:54Miles Grimshaw:I'm like, where's this candidate looking? What's there? They're the writer of their book. What's their book going to say? This is the next chapter in it. Where's that book going? Where's that storyline going? And does this fit that? And can I help them see the degree to which this does fit in that story? I guess the board member piece, I think the job of a great board member, I think the job of an investor, the investor I hope to be, is that a founder would say, Miles helped me, we helped them make better decisions. They are the founders' decisions to make. They never are decisions to make. And if we can give them perspective, resources, input, what have you, for them to have made better decisions on the way such that they have a more successful company, they accomplish more of their dreams, fantastic.

1:25:54Some of that is also recruiting people to the team because it gives them better input on the team, et cetera, et cetera. and there's resources you put around them. And we have an amazing team that works on marketing and finance and sales with all these companies. But one of the core things is helping them, certainly as a board member, because I'm not the one doing the marketing. I might look at a lot of copy or something, but I'm not the one doing that, is to help them make the best decisions. And that's like the ethos one grounds everything too. And it doesn't mean you're always yes to something.

1:26:26In some sense, sometimes I will, and I'll preface it, I'll say, I'm not sure I believe in this, what I'm about to say per se, but you should hear it such that under hearing it, you're still extremely confident in the decision you're making, because this could be another scenario of the world. And if that scenario is some obnoxious edge case, it's not productive. But if there's a real consideration or a failure mode one's seen at other places or a risk or consequence of something that's seen at other places or the positive of that, you want to expose that versus just be like, yeah, of course, great.

1:27:05I'm not here to push an opinion. I'm here to give perspective such that the founder, when they're looking, makes better driving decisions. And that's our goal. The only other thing I'd say is I've actually heard this said from Sir Michael Moritz very early on in my journey, which really kind of didn't mean much to me, but it stuck with me, which is it was said to me that he said. A great board member is demanding in good times and supportive in tough times. And so they're kind of a spring, a shock absorber. They're a shock absorber. Yeah, yeah. and I kind of understood that it sort of made some intuitive sense to me but again to LHS I didn't really have the feel for that and what I've realized is the reason you need to be demanding in good times is because that's when you can like level up to the next area it's when you have the capacity to be the next amazing recruiter so when you have the capacity to walk into a room with a customer maybe you shouldn't be the sort of one serving yet so when you have the capacity to like raise the capital because things are working well.

1:28:11And so in success, like when things are working, you need to like, again, set your eyes further out. Yes. And amplifying the pressure on that in good times, I think is a very important thing for a board member. It's actually, the more I've done it and seen others, the times when usually less attention is given because it's working. and it's actually almost a time when one needs to try and lean in a little more because it is the time to do that and simultaneously when things are not working that founder has thought about all the ways it's not working all the pain of it not working and all the way more than we ever will we ever will and constructive help at that point is probably most fruitful

1:29:06Miles Grimshaw:as I understand it when you joined Thrive, it was not a super obvious decision. I think you also turned down Bridgewater. I was originally. Why did it feel right to you? And more broadly, what do you think went right early on, both for you and for Thrive? The curiosity I had for Bridgewater was not macro trading at all. I don't care for macro trading. There was not an organization I knew of. I was in college, so also didn't know everyone. that put more thought into thinking about people and organizations. And so Ray Dalio's principles hadn't been published, but they were sort of an internal thing.

1:29:48And when you do the interview process and then we spend time with the team, there was like so much curiosity. So like team organization, et cetera. And part one is build a great product to deliver as a company. And then there's build an organization that can build great products is the job of a founder. So I was kind of fascinated by Bridgewater for the latter question, not for anything to do with macro trading, what they did. But what I loved is building, imagining building and thinking about how to build great. Where those opportunities for change was opportunities for new ideas and building products and making sure they succeeded around that.

1:30:32And I know it seems silly now because it's like so understood. But, you know, in my last two or three years, certainly two years of college, I read like TechCrunch most days. It was not as much of a thing, but I read it most days. I read Hacker News. I can relate. Like there's a blog that no one would know now because there's so many blogs on SaaS. But SaaS in 2011, 2012 was really early still. I wish I realized how early it was. You know, you're not aware of the water that you're in at times, but it was so early. It generalizes. And there was a great blog written by David Skok, who was a partner at Matrix called Four Entrepreneurs.

1:31:12It was basically all about the SaaS business model. And no one of this generation would know it anymore, but like, it was amazing. And it was a gift that he put so much of this out there. And he was studying this business model and thinking about this business model and working with HubSpot and some others. And I actually interned at Matrix and I read all of this blog and was like a voracious consumer of it. And that curiosity and love of learning that translated to me meeting Will Gabrick and then Will joined Thrive. And they said, you should come join us. At the time, we were mostly done consumer investing.

1:31:48Bobby Parker, Harry's Instagram was a great success. And I was like, but I think the software stuff is amazing. And that led us to Segment and GitHub and other things. what went well in that sense i think to our earlier comment the early reinforcement learning of what really great greatness looks like i think instagram github josh building oscar was like um really powerful for just seeing how great great can be and and how amazing success what amazing success can look like um and then for myself we josh really leaned into people who had a lot of will, even if they didn't necessarily have any proven ability.

1:32:36And it's something that we've really continued to do. And our most recent member of the investment team joined us when they were 20 years old, so younger than I was by quite a bit at that time. He actually dropped out of college to do it. And I'm extremely grateful for Josh and Will and Chris and Jared for leaning into a lot of willpower and earnest curiosity, even if there was absolutely no reason to believe in it. And it was way more controversial at that point to leave college and going straight into investing. And so I'm very grateful for the risk they took.

1:33:15Miles Grimshaw:A friend of the pod, Jared Weinstein, says, Miles was a punk. And I say that in a complimentary and long on Miles way. What do you think he meant? it's funny I've joked to Jared that the best compliment he ever gave me was Miles is a punk I think again it's sort of probably in that theme of

1:33:44I'm not an A student in the sense of I'm not someone who gets given a you know a test and says I'm going to go now I'm either I'm either fanatical about it or I'm not giving it much attention and picking the things you want to focus on, picking the pursuits you really care about. And in those, I'll also be very honest. Never because I think I have the perfect answer or the right answer, but just the love of that engagement and that dialogue and that journey.

1:34:21and I think that said in a fun jesting way amongst friends is, you know, punkish. And definitely when I was early on, I probably did not communicate in the most effective way at times too.

1:34:33Miles Grimshaw:And so I've learned how to - Or in frustration, you couldn't communicate your intuition. Yeah, it's a great point even actually now. See, my son, my son is definitely sometimes a punk too, but it's also like, he doesn't really know how to communicate the thing that he wants to, you know? And so I went on that journey and I'm grateful for people sticking with me on that journey. One of the great things about Thrive is we're extremely collaborative. And I think the best version of investment team conversations are not a jury trial. It's like being in the music studio making music together. and I think people think of investing in investing committee as like the jury trial yeah it's like I want to do this and your job is to find me guilty yeah you know and that's terrible um and I think the the the best version of it is like we're kind of in the studio jamming riffing figuring it out of which yes we came prepared and we all had sheet music that we what, you know, music beats that we worked on or whatever.

1:35:39But like, we're trying to get at the magic of this, the right answer to this and figuring it out. And I think we've always had that ethos at Thrive. At times as we were all figuring it out because we all started young or figured it out together. You know, it was probably more of that debate than the making music. And, you know, the punkishness is another sort of element of us all learning to communicate and be amazing together. But always a strong belief in that, the better together. the collaboration of that, even when it's maybe not the easiest path.

1:36:16Miles Grimshaw:Most people succumb to inertia or sunk cost when it comes to making decisions. You made two very unusual decisions that create a strange blip on your very thrive looking resume, which is that you chose to leave and join Benchmark. And then not only that, but you chose to leave benchmark and return to thrive. I suspect there were a lot of things involved in that decision, including more strategic thoughts or opportunistic thoughts, also emotional thoughts, humility, all these things. But again, I think most people, certainly having made that decision once, probably don't like do it again. I would love to just hear a little bit about how you made that decision to leave and how you made it to stay and how particularly maybe on the return, you had probably largely the humility to say, I made the wrong decision, or at least this is the right decision for my future.

1:37:14Miles Grimshaw:I'm going to go back. I like your frame because I do think it's actually something an LP once said to me, and I hadn't quite thought of in that light, which is actually a required, in some sense, like a lot of humility and letting go of others' perception and not caring about that and caring about oneself and being honest and true to oneself to say, yeah, it wasn't right. And this was, and I made the wrong call in that regard. I think that to some of our conversation of like loving change and hunting change and being comfortable in new situations and seeking new situations out, you know, a bit of, to myself, it's very, I think it was probably very weird for me to imagine being at one place for my entire life.

1:38:12And it so happened that that, that is true. And that the place I joined, not knowing anywhere else, basically, um, is that place.

1:38:22Miles Grimshaw:Uh, and, and so to my point of some, uh, early of like helping people see, you know, what's our chapters, who are you, what are you writing to the recruiting thing? Sometimes, you know, it's hard to fully know the water you're in when it's, you know, the only water one's had, even though I knew the water was fantastic and I just was heads down all the time on it. And so I think partly I had to go on that personal journey and I'm married as well with two kids third on the way. And I think that I've also come to see, I was always someone who was like leaving and, you know, I left the UK with my parents.

1:38:59I then went to India. I went to China for half a year. I changed majors senior spring, you know, kind of like left one thing, did the other. Like, I'm always sort of like new in that because that's sort of the clearest sense of next challenge, next adventure. And I've come to find a lot more the magic that gets unlocked by like a strong foundation in my personal life, like having my wife like as my rock, you know, unflinching and supportive, like allows so much more adventure than, you know, if that was not there. And I think in Thrive, having that be so strong, all the trust and understanding of each other and being demanding and supportive of each other we built up allows us to do such amazing things.

1:39:48And how in some sense that not being changed and not being an adventure allows for more of this out in the world together. And so I think I've come to mature in that sense. And then you've got to just be true to oneself. The benchmark team is phenomenal. I've learned a ton from them. Eric Vistria, I think, is remarkable at connecting theory to operations and change and execution within a company. He's totally full swing in that regard. I think Peter has amazing wherewithal across consumer and enterprise. It is remarkable. My good friend Jack Altman, who is sort of an entrepreneur's entrepreneur, is like there.

1:40:32And so I have a lot of fondness for that team. But you've also got to just learn what is the right fit for you. And to some of our earlier conversation of Thrive, we are insanely collaborative to that point of just loving trying to figure out and think about reality. and our views towards the future together and the dialogue and debate and discussion of that. I never did debate in school or anything. I thought it was kind of weird and esoteric because like, why do I care about debating that topic? I don't. But like, I love that for Thrive and I rely on the team a ton for their input and perspective.

1:41:12And then we are a group that is always on. And someone once told me they read a book on a DJ, I forget the name, and they said, they recounted this aspect of it where the DJ said he had to sleep with the dryer machine on because it kind of like just needed the noise. Like, I like love the intensity of our team to the turbo puff at 9.30, Monday night, 10 p.m. call. The other weekend after the World Cup final, We're all on a call at 9 EST before Philip and I went to a founder's dinner on Sunday night and then Monday morning straight again. We're constantly calling each other, constantly pulling each other in.

1:42:00There's an idea possible every day. The impatiently patient, like always be hunting. And Josh's incredible in this. I remember after we'd agreed to our investment in OpenAI at$150 billion. and there was a lot of turmoil at that point. Obviously, in general, people forget it, but Greg Brockman was going to leave. I think it's John Shulman was leaving to go to Anthropic and then I guess thinking. So that was not straightforward. And Josh had flown back and forth to the West Coast two times in like three days. And we have Thursday morning deal. We got an agreed Wednesday night. We have Thursday morning, 7 a.m.

1:42:44deal meetings. And Josh has got the three next ideas to the point of be demanding in the good times. I'm someone who I've learned loves getting the call at 7 p.m. on Saturday night. I'm with my family, but I step out for 15 minutes to have the chat with the team or to do the thing. I like that always on nature of things. And so to thrive is just a personal fit.

1:43:20Miles Grimshaw:What's, at least that comes to mind, what's the most important thing you've learned from Josh? So it would be hard to say just one thing. A few things might come to mind. One is, again, to this point of great CEOs and with them looking where they're going, and the way they look, that's ambitious. Josh is insanely ambitious. Look at what he's done. Thrive, founding Oscar, holdings, supporting OpenAI in good and bad moments. and the idea of the person who wants and not necessarily the person who's most credentialed or most experienced and the power of will, a can-do attitude and determination. Like he's a founder and an incredible exemplar of that.

1:44:26And so even more than I might imagine possible, you know, dream bigger. I learned to dream bigger from him. Two, I think he often will say and is imbued in the culture, it's not just winning, it's the way we win. It's not just the business, it's the way we do business. And he has really led with kindness. And so I think he's an amazing exemplar in sort of like being kind and competitive. Competitive might not be against others, it might just be against oneself. the element of drive in the competition part, but the kindness in combination with that, I think he really, really leads by example of, raises the bar in the way we do business, not just the business we do.

1:45:19Miles Grimshaw:Just a couple more things. It's funny, you wrote an old piece for like some Yale review about how education might change, which I thought was quite good. It got me thinking what your kids are, I think the oldest is for, how do you think about what is most important to teach them or prepare them for a very uncertain world? I thought you were going to say, what might that world look like for them? I was just going to say, I don't know. Like, I really have no idea. I think two things probably, although we have never made like family principles or something, which I know some people do or whatever, more organic.

1:45:55I think one, it's really important to be a good, kind person. And so all of that, obviously, although you have to work on that every day and remember that's a muscle and an act. And then two is I think that agency and agenticness, to use the AI version of it all, is more important than ever in many ways. Like you can have all the intelligence you want. What question are you asking? uh, what, where do you want to go? And I think that agenticness is something that I hope to instill in him, you know, a fun version, which we haven't gotten to yet that I've seen on the, on the Instagram reels, love Instagram reels.

1:46:45You can learn a lot is, is, uh, the, you know, get your 10 year old for their birthday to pick the family vacation spot and make a presentation, you know, kind of way it's like, I'm looking forward to having him do a, you know, 10 year, a 10-year-old family presentation of where we're going. But I think it's true for other things. I probably shouldn't tell you this because then recruits will listen to this, maybe. But one of my favorite questions is, what's a relationship, personal, professional, what have you, that has come out of proactive, a cold email, a cold outback, whatever? That's very agentic.

1:47:26Yeah.

1:47:27Miles Grimshaw:It's been the serendipity wheel. Yeah. And constant curiosity, you know, show me the last chat GPT questions that you had. Yeah. Yeah. Yeah. I have, we're registered, so I actually have two phones. And my son asked me the other day, he's very curious. He goes, why'd you have two phones? Well, that's a hard one to explain, I guess, a work phone and postal phone. He goes, do you have two chat GPTs? because we're always asking chat GPT questions. If you ever ask me a question, that's a good one for chat GPT. Let's ask chat GPT that question. We pull up voice mode. And so, you know, I try to cultivate that curiosity.

1:48:06Miles Grimshaw:I think when we first met over Zoom, we were talking about long distance running and endurance and pushing through and so on. You've done, we talked about adventure racing. I think you were a rower as well. This comes maybe back a little bit to what we spoke about at the top, which is, and forgive me, but I think this is something you literally said. I was never faster than anyone else, but I was like, I'll go longer and I'll suffer more pain than anyone else. How do you remember and how would you encourage or advise others to dig deep and have endurance?

1:48:44I think part of it is developing the muscle and the comfort of doing it. Like maybe there's no shortcut. And your mind is something that I think you can train. I did, this is early on, I have no idea, but I did my first marathon when I was 17 because I was like, I was about to turn 18. I was like, I got to do it before I turn 18. And I don't know that I'd run longer than, I'd done the adventure racing stuff, but in adventure racing, like we covered 250 miles, but you're not like marathon pace for that. You're like, you know, hiking and you're ascending 10 ,000 feet more than you're running a marathon.

1:49:30And I was like, I just got to do it. So I basically went two days later, the Abandoned Boston Marathon. But I think more people could probably run a marathon if they just like went out around 20 miles or something. Like once you know you can, you can in some sense. And, you know, the first time you do a 60-hour race, my wife and I did 150-mile race in New Zealand. She's an elite marathoner. She's like, I don't know, top 50 in the US marathoner. She runs a marathon faster than I can basically run a mile, a sub-six-minute mile marathoner. Oh, my God. It's insane. It's insane. But she was like, I'd always wanted to race this.

1:50:15There's a stage race series called Racing the Planet, and they do them in the four major deserts in the world. And then they have a moving race each year, a fifth race. And I found out once we were dating that the fifth race in 2019 was in New Zealand. I was like, New Zealand is like the most beautiful place in the world to get to do this. It turns out it's incredibly hilly. So we ascended and descended about 8 ,000 feet a day, which is absolutely brutal. So it's a very bad thing in that regard. And half the race never even finished. But I was like, we got to go do that together. And also to the point of like having that rock and more adventures, like having someone who would go do that.

1:50:55But when I first brought up with her, we were actually hiking around Mont Blanc. So we did the Tour de Mont Blanc. Uh, but I was like, we, we should go do this 150 mile stage race in Louisiana. She was like, you're out of your mind. Uh, and I think part of it is just like a bit flip and she did it. And now she's like, yeah, you can totally do that. And then I think, I think it was after that she did rim to rim to rim. So she ran across the Grand Canyon and then back. And, uh, she was like, Oh my God, that's so easy. Like we got to go do that. You know? So like, I think once you do it once you develop the, the develop the confidence.

1:51:29And so I think there's as much a mental game as anything else.

1:51:33Miles Grimshaw:That's all I got for you. Thank you. Fun to do. This was a blast. Yeah, appreciate it. Thank you for listening to my conversation with Miles. And thanks again to Notion for presenting Dialectic. As Miles mentions in the episode, we are moving from an era where software helps you do work to actually doing the work. And I really appreciate how thoughtful Notion is about that distinction and where the line should be drawn. Notion remains the hub for all of your documents, databases, and everything else you and your team use to collaborate, to write, or otherwise. And they have thoughtfully integrated AI and agents into the place where you do the actual work.

1:52:10Miles Grimshaw:This includes custom agents, which are little guys who work in your workspace. This can be other agents like Cloud and Cursor that you can tag directly. And it can be more complex things like Notion custom workers and their developer platform. But all of these are integrated in a way that It allows you to automate away the busy work so you can focus more time on the actual work, the work that requires your deep care and focus. Akshay, Notion's co-founder, told me that there are now almost 50 former founders at Notion, and the team is growing across product, storytelling, design, engineering, and more.

1:52:44Miles Grimshaw:If that's you and you would like to join the team at Notion and you think you're a fit, you can reach out to them directly or email me at workatjacksondoll.com. You can learn more at notion.com slash dialectic. And by supporting Notion, you support me in dialectic. Thanks again to them. And thank you for listening. Once again, if you enjoyed the show, please share it with a friend. With that, I will see you next time.