20VC: Benchmark General Partner, Miles Grimshaw on The Five Pillars of Venture Capital, Why Data Can Be a Trap When Early-Stage Investing, Investing Lessons from Missing Figma and Plaid & The New Business Model for AI & Why Co-Pilot is an Incumbent Strate

22:42Do you think most VCs do? Often people say on the show, VCs do more harm than good. Do you think that's fair? I'd say, two, one, you should always have the hypocriticals. Do no harm. I've been in some board meetings where investors don't really get the product, don't really get the strategy, it has to be pursued. A trino apply, procedures and checklists, you know, versus strategies specific to the instance. It becomes a reporting structure, it becomes a distraction, it becomes a management but for the founder and so yeah, Hippocratico's. The second is though, I think that it's not that you always have the answer.

23:17Part of it is I found a trust to you to say, I'm working on this and come to you with it and you're working it together. I don't think you have to always, in fact it would be dangerous I think to assume you've always got like the perfect answer and opinion and everything so much is to say, with that context, with that trust, with high velocity communication, you can go work through it. I'm so enjoying this. So I had Sam lesson on recently and he was like, the best founders, they don't need me. When you look back at your best founders you've worked with, do you agree with that statement? The best founders don't need you.

23:47They will have done great things absent and investing partners sure. Can it further supercharge that? I think so. But you can't co -tight. Gotta have it. And so yeah, I think the very best are very capable. But I think the very best with a great trusted partner as well, deeply committed to them can add to that. You'll look at even the very best, I'll look at Jeff Bezos, but he's still got a board And he still got partners who've been with him that entire journey. I always say to my mother, it's like an ice cream with hundreds and thousands of years. Sprinkles on top. No, ice cream's still great without the sprinkles.

24:16But it makes it a bit nicer and better. The idea, okay, so we've got servicing as number two. We've got, so that team's number one was three, four and five as we go down the chart. This sort of pageantry of signing, winning, whatever is, if you think of investing as betting, I think you spend a lot more, you know, a lot more energy on the funnel and winning the first psychic place and chips on a Rulat table. And I don't think of it that way. I really think of it. The work we do is making a commitment not a bet. And if you were to sit around our partnership meetings and the like, you really wouldn't hear the word bet come up very much in that regard.

24:53And I think if you listen to many people in the industry talk, you'll hear the word bad. I bet on this. I bet on that. You know, that's a bad bet all the time. And I think if you're more wired that way, you think of it more sort of as that funnel, sort of the sourcing funnel and coverage, you know, to make sure you get exposure to the best bets and sort of the signing of them being kind of the end of it is the most important. So those would be after the other two for me in which order I'll let others tell me. No, listen, I totally get you. I'm always oscillating between these and I think you've kind of come to a rubric myself, but there's founder, market, and then there's kind of traction.

25:26When you think about kind of weighing these three up, how do you weigh them? There's no right or wrong, but everyone has their own approach. How do you think about that root break between founder, traction and market? It's the integration of it all. Well, I thought it was interesting. Nickel was like, I can't do anything pre -traction. If it's pre -any data, I just don't know. Yeah. I'm comfortable doing it. And in fact, I used to do more growth investing, later stage investing. And I actually would always push myself and the team on the idea that we should have a point of view of what data should look like, we should be able to have strong theories absent any data, we should always start from like products and customer not data.

26:07And data should be in some sense validation, not learning. Simply said maybe like data second investor. And so I'm quite happy doing that personally. I actually even think at all these stages like data can be a trap. And I often say with companies I work with or companies I'll meet with like they're always buying to get to you know, X million of revenue so we grow at Y percent for the year. And I'm usually much more like what do you really want to prove in the year? What do you really want to have loved in the year? What would be the right custom adoption in the year? Often cases I'd rather take less growth in the right ways than more growth in the wrong ways.

26:39So I don't personally see it that way. The revenue is always an annoy one for me because it's now put metric. I'm like was the input metric that you got you that was the seediest bandstunner? We can't ignore it by any stretch of the imagine. But when you're in these early stages, I'd call early suddenly even tens of millions of revenue, not just like one. You're setting up systems, you're setting up learnings and systems for the future for to repeatability and scale in the right way. All the success and certainly wherever you can be empty calories. If you think about it as a diet, like you want to make sure you got a good diet, not empty calories.

27:09And so anyway, back to the sort of aspects of it, I really think about as an integrated system. And so the real question I think about a lot, which gets to that sort of holistic nature of it is, how do I imagine recruiting for this? If you think about the journey after investing, I'll probably do many hundreds of recruiting calls between exact interviews as they change exact teams on that journey between individual ICs that I might help out with early on. If you then add in other investors you're going to have talked to about the company, you're going to have like pitch the company hundreds and hundreds of times.

27:41And so they just apply to the recruiting, which is the core bulk of that. No recruit is like just on, well, how much money can I make? That's a very mercenary recruit too. And so the mission matters, like really walking form matters and the team and it's called, and so the recruit is thinking about it in a holistic way. And so we actually just had a partner me the other day. One of my partners was that, literally, before asking any other question, we asked my other partner, can you recruit for that? Like are you excited to recruit for that? Really is a cool one for me. If you say, okay, Miles, what do you really look for when you're making in your investment more with Investors Speak?

28:13I think the biggest one is what's changing? Where's there a gap? what's new either from their perspective, what's a gap in the market that's opening up and change gets the opportunity for new, but gets the opportunity for dislocation. And then you've got to have a founder who is authentic to that strategy that can get on the field and work in interesting ways with that business model that you think can be valuable upon success within that, but that change or the ability to, when a founder comes to a creative act to sort of try and make change is the core of being able to really get going. And so, so actually it's market timing, even more to me.

28:46You might call it that. I don't partially think about it as much from sort of a timing lens, so much as the investigation and the thinking of like, what's different, what's new, what's a dislocation, what's emergent. We're going to take adoption risk. I mean, I think, you know, I had Vinalcosa on the show before and he's like, you know, I'll take all the market timing risk in the world, but I won't take adoption risk. I think it's dangerous to this sort of like, I don't know if you go back to sort of philosophy and economics as this idea of like normative versus positive right normative how things should work positive is like how they do work.

29:20I think it's dangerous in many ways in a vista sort of to think other world should work this way and now I'm looking for people who also think the world should work this way but don't really have the strategy from cracking that open or there's not dislocation that opens up the window for that to happen. So I think that can be on the flip side sometimes you think the world should work a certain way and a company's got an advantage in a moment in time with which it isn't working that way, sometimes that also doesn't happen. Like the world doesn't correct itself. And so I think that can be dangerous.

29:47Coming back to the user, working backwards sort of from that, I think can put you in that mindset of that adoption question and like timing can sometimes be how can you reach those sorts of things? I think you can sort of puzzle through that in a way. Force of will can do a lot, but you're going to feel like the dominoes got tilted over. You know, you're looking here, but the domino chain is sort of happening conceptually in the market. And so I'll sort of happily take that and go on that journey. If you feel like the Domino's are starting to really falling. What was speaking about going on that journey, how do you bring the partnership along with you in your excitement in a deal?

30:21Do you tag teaming up at Banch? What were you saying? Hey, Chathen, let's get on this together and then you discuss it as a partnership, but you and Chathen leads. How do you bring everyone with you in your conviction for a company? Here we do, we do a lot of that. Hey come join us, hey let's go and meet together. There's ultimately one person who takes a bullet seat, right? But it is a, again, we're an equal partnership, so it's a whole firm commitment. No person is incentivized to help more one thing versus another. A founder really gets a whole partnership, but obviously they have a principal relationship, a dominant relationship with one person, but we're constantly pulling each other and actually just before I came here, a founder who works with Bill Girlade, spent some time with recently and sent me a text like remembering something I'd said to him in a line because he was using it again and again.

31:05And so we're always pulling each other into current investments, future investments. It's interesting, you said it was about being data second. I actually think reserves are financial mismanagement. Fundamentally it's better case on data, most often like immediate traction, and next six to 12 months post -investment. And when you look at it and then apply it to the benchmark portfolio now, but like the docker of the world, you would have not invested in and subsequent rounds of Docker, because of tradition misleading you. How do you think about reserves management today, given data can mislead you?

31:38We really don't think about it very much. She would hit the spreadsheet of our investments. Almost all the capital we invest is the very first time we partner. And yet we have reserves, tough times happen. Oh, who knows what, right? Like we certainly have reserves, but we don't reserve with a mindset of buying more later. We don't reserve with a mindset of, Hey, we started, we got some ownership now, we're gonna try and buy some later. We're either fully in and it's a whole commitment and that's what we're doing, or we're not in. And so we don't reserve with a future investment orientation. I wish I could just, I mean, as you can see, I wish I could record that and play that 12 piece because I say very similar, but it is recorded so that's the other one.

32:20The one thing, if I'm not picking holes by any means, but a benchmark could like, famed on being the series A and master. And then you actually look in your like airplane .dev, which I think it's announced, was like the first money in and then I add Table was like seriously. We had how he on the show the other day. How do we think about where benchmark sits in landscape given moving to first money in in Seriously, I think it's something like 50 60 % of all the investments we make were the first partner. 30 % were literally the first investment. You know, we don't use the term incubation, but I think probably about a third of investments all out of inception.

32:59It's not to say that's really the focus. There are occasionally exceptions. You worry in terms of positioning then, in terms of competing with a very busy and vibrant seed ecosystem. What I mean by that is I'm sure we both know a feeder at Blossom in London, but she very specifically doesn't do seed because she always wants to be non -compassitive to seed players. By doing 50 to 60 % as first institutional capital, you know, that first kind of firm check, you all can pass the right yes to seed managers. Like, I don't think it's zero sum by any stretch of the imagination. The end of that in a given year, even for that percentage, is like three companies, right?

33:35And so it's not like we're doing 30 that way. So the end is small, and there's a lot of you companies formed each year. I don't think of us as competitive, I think to our point earlier, some people maybe think of us later, And there's no such thing as too early for when we invest there's no such thing as not enough traction My question to you is we learn a lot from successism failures when you think about your biggest wins What have been your biggest lessons or takeaways when you reflect on those wins because they do ingrain lessons. Yeah, I think if you realized it probably get helpful segment if you look at unrealized Maybe a benchling or a monso and so I'm benching on monso is funny a lot too very different things Benchling really is a visceral, felt story of the power of someone perfectly matched to a totally new market and a story of what could maybe seem like a small market because it's a vertical market getting opened up and being the leading provider to grow with that market.

34:31If you want a positive feedback loop to small, but growing markets with, you know, high degrees of market share in them and a found a perfectly matched to dominate that market and what could be possible, It gives you a feedback loop for that lived reality. Mons are the exact opposite in many ways, in that it's banking. It's a UK, some for many outside the UK audience, that might not have barely heard of Mons are, because it's a UK phenomena, but in the UK there's something like 60, 70 million cool checking account users in the UK. Mons are now has 7 million accounts, it's like a tenth of the British population has signed up to this thing.

35:08And both of these, by the way, Like, Benchling was five people. Monzo was probably like 30 people, but about like 5 ,000, maybe kind of test accounts. It didn't even have the full banking license yet. But it's a feedback loop right to strengthen confidence in the idea that a ferocious founder with a no -hole back, all the elements attack on a market can break through a ways you did an unimaginable in many ways. Tom like really did that, you know? He did everything from get a full banking license to build out all the technology from scratch. And this is where, for me, it's a story of a founder, again, incredibly mission -driven, incredibly mission -driven, and ferocious, where it's all against that.

35:49Like, there's so many marginal and incremental decisions that teammates, and like, they're all that way that sort of totality of mission ever found at a breakthrough. And to me, it's like a feedback loop on how special that can be as well. On -founded detection errors. My biggest error is when a salesman found that was saleswoman founder is very good at selling and actually that execution doesn't align to the quality of their sales. That would be my biggest founder detection error. What would you say you were biggest is where you thought you saw something that wasn't there? The greatest regrets I have are where I thought someone was really really special and I got two hesitant on market.

36:25What was an example? I give you three Dylan, a figma, zacka, plaid, and Alex's scale. Got to know us for real. Really early and I just, I started, you guys know figmen because There was that intersection with the A1, Johnnie did the A. Product was developing, but there was no rules and release. Yeah. I spent time with Dylan at the round the client I ultimately did. Also again, I went to Core invested. It was definitely the one I am most mad at myself for. So on Figma, the hesitation I had, I didn't think designers was a particularly large N. I think if you went and asked how many designs there were on many of your companies, certainly relative to engineers would be a tiny fraction.

37:00I think N of design is relative to accountants some latest issues of startups would be tiny. So what makes you yeah what I missed the adoption for far more users into the product and I know are you conceptually new but I didn't wear it enough at the time and that's what eats at me the most because I think about doing this when I look at products and be product first is what's that nature of the product and the nature of design inside a company of digital product like really brings copyrighters come in marketing people come in product managers come in engineers need the There's a lot of people that all bit that asset inside of a company, that workflow inside of a company.

37:34I was like stupidly, myopically thinking of it as a design seat, as design software. And what I should have been thinking about is the nexus of collaboration for digital product, of which design is the core stakeholder, but all these other people orbit it in a very involved. It's if you go and look at the data, the time it actually was there. It was in front of me. Sometimes maybe not being data first enough is a miss. There was the data that showed it. There was revenue wasn't, I remember when the public, but they were four million there or when Andrew did them 400. Everyone was like, yeah. Dylan had showed charts.

38:05It didn't sit in my mind properly enough at the time of all the other non -design users inside the companies using it and as active seats, them as paid seats. And I think now, if you go ask for their spend on Figma, many of them probably spend more than Slack, which was wild to think about. And I would never have guessed when you think, First, principle about it, the nature of that product, it sort of makes sense. And so, how that actually plays out is probably a third of the company for my surveying, has paid seats inside of Figma, and they pair our three times as much as they would for something like Slack.

38:37And so, the bill and the revenue they're driving is enormous. I didn't appreciate that. So, it's a lesson for me in really thinking about and sort of inspecting, getting to know and understand, like, what's unique? What's sort of counterintuitive? Anytime you're getting to know a team and thinking about a product, even post that, if something seemingly unintuitive is happening that's potentially caused for a lot of excitement and certainly to be a student of and I like to think of myself there where it's the one that grates me the most because it was right there when I didn't wear it enough. My maple set's like, what secret do you believe that the world doesn't see yet?

39:10And I always tend to ask that question, what do you miss with plaid? This to me would be a story of the world doesn't necessarily work the way it should work. in that plaid really solved Oauth for bank accounts. But the idea that Oauth in general was a hard problem was like not that hard. Like Reddit I think probably has an Oauth system. Like you can build an Oauth system. Conceptually the world that should work is every bank and there's by the way highly concentrated in the US, so like five banks control over 50 % of accounts in the US. The idea that those five banks couldn't offer an Oauth system to get account and routing numbers.

39:44That's all you need two numbers out of them to authenticate. In my mind it should work. They have no incentive to do that because if they let you do that, it's easier to move money out. And they don't want you to move money out because they make money on you, storing money there. That's how it back works. And so no bank has an incentive to actually offer this. And so again, you think you use a first economic incentives in the system. It sort of shouldn't work like this, but it's not a complicated technical product and then you're asking, so it should work like that. And I got too intellectual about it.

40:10And again, amazing founders like people I feel lucky to still call friends and just people who even then I knew I wanted to just work with. and that's the magic of this journey, so those are the big regrets. The thing that strikes me when I hear you discuss those, and then also think to it, that I'm chaining and then some of your hits including segment, as well as you mentioned earlier, and GitHub is actually the breath, the breath of material and landscape you need to cover, and I actually spoke to the dips he found us before this. And they said, I was came about specialist first as generalist because he is able to be so broad, unlike many others.

40:43How do you think about that breath in generalist first as specialist? Firstly, I can't help myself. Maybe, you know, too much curiosity. That said, I thought I had a lot of curiosity and then they really got to know my partner, Peter Fenton, he, I think, he has, like, clinical curiosity. Even my curiosity has a ways to go to catch up. What makes you say that about him? He just cannot stop. Yeah, just sort of insatiable desire to learn. I think most people I know, most friends and others would say that's true of me as well, but when you see someone with it even more so, it puts you in your place.

41:14But in some sense, why the breadth is just curiosity pulling me into different places, and usually in many ways very found or driven. You have an inkling of interest in an area and you meet someone like Tom and you go, you want to walk with Tom. You meet someone like Dylan, you meet someone like Zach, you meet someone like Saji at Benchling. In some sense, I think myself is a sure gem -less, really ending up being a specialist in helping founders like that accomplish their dreams to make the very best decisions. And I think of most health as becoming a specialist in not in the same degree, but in many ways in their companies and their situations and Specialists in helping them connect up that strategy and vision into the sequencing and to the organization And I would say that many of the almost all the great companies are not like a carbon copy replica of a Playbook from some other prior either.

42:03There are lessons absolutely learned from the past But I don't think it's a stamp bit out assembling line process, right? that, stride does not pay bow at segment. There was a lot of pressure and we did, also in the positive way, learn lots of lessons from stride, but we were very different to stride. And too much of the stride lesson was detrimental actually to being at the best version of ourselves. And so I don't think greatness is a carbon copy either. And so I think in order to be the best partner to a founder making the very best decisions, you become a specialist in theirs, but it's about applying strategies and learning from strategies, not learning procedures.

42:34And I think the more you become a theoretical specialist, where the more the temptation is to say, here's a procedure, here's a checklist. And I think they're very best at not that. I can't help it. Do you feel insecure when I sit down with our mutual friend, Nico? And Nico just comes out with the most rigorous benchmarking on tax for consumer subscription companies. And I'm like, shit, I'm not as deep as that. Do you get insecure when you hear specialist speak in the debt that they do and go, fuck, I can never be that? Yeah, absolutely, but I think hopefully can help people get connected to those people for those expertise if that's really what makes it.

43:07And there's a lot else that goes into building a company. And there's moments probably where there's metrics of the wrong things, right? Like where benchmarking perfectly to the playbook of that vertical, like you're gonna break it in some ways, gonna look different in some way. The generalist being a biologist versus a physicist. And I think the specialist can become a bit more physicist. Like here's the playbook, here's the rules. And I think of myself as a biologist in that you're constantly looking for like new adaptations and new variants and curious that, which is why the figma thing annoys me so much of myself, right, so new adaptation.

43:39That's the sort of psyche one applies it to. If you want to deploy capital, being a specialist is probably good, because you say, hey, if I pass enough of these rules and I have a lot, why enough portfolio, it'll be good enough, but I just don't think like that. You said about new variants that. I think I do wanna ask is, you know, obviously you've had the line chain deal. One of the hottest and most competitive deals, I think when you've added and then subsequent round, my question to you is, and as you hear us, How did you first get into A on LLM when you did? Yeah, so I was spending time sometime in 2022.

44:10You saw the first versions of things which were sort of spitting out content, right? But you started to see in mid -2022 or so this idea that the models had some amount of reasoning capacity. And there's two things I might point to in that one. One is they can do things like know which colors are like each other, which things are to be a ability to do math. Now, in some sense, that's learned from the language and statistics at the end of the day, but the fact that those properties were kind of there was fascinating. And then you got things like the React paper, which was sort of this reasoning and action and the model kind of giving it feedback to itself.

44:44And you started to see, at least I started to see when I saw those, is like, there might be so much more here. It might be a sort of new computing paradigm in a way. And there's more power in this than just sort of marketing copy. And you combine that with another aspect that I felt could be possible and proving out to be true is that ML had been in many ways reserved for ML wizardry. The folks who knew how to build the models, changed the weights of the thing. Many teams had ML folks on the team, just for their application, just to be suffering with their data. But it was sort of like a separate group than every engineer.

45:19And you start to feel, and I started to think in mid or so, 2022, that every engineer would become an AI engineer. AI would be a part of it all. And there wouldn't be, you know, hugging face, you've got a hugging face. It's for the ML wizards. It's like which variant of which model, which, you know, weights. And instead it would be part of every application engineers like core thinking. And so you would get tens of millions of engineers would become AI engineers versus like hundreds of thousands of ML scientists. And that that would forget the need for an application sort of framework for AI and tooling for that computing environment, which is very different.

45:58Like, that's sort of stochastic. There's randomness to it. How do you measure excellence of it and a many model world as well? And there's an opportunity for built and power every engineer becoming that, which is what you sort of saw happening and certainly what led to partner with Harrison flanking. Do you set before the comparison to mobile, which many have made, many have said that actually this is similar to mobile and actually the incumbents will need to shift to it like they did to mobile? You said before maybe that's not the right analogy. Why do you think the comparison to mobile is not the right analogy?

46:26Yeah, I think as shifts happen, we want to analogize. And no analogy is going to be perfect. I'll compare it more to the idea of what the internet enabled, the mobile enabled. But like both of those were also new distribution channels. And this is not a new distribution channel. So both of them are fundamentally flawed in that way. I'd also argue though, if you think about distribution is closer to the internet and that the internet was a distribution channel, it also catalyzed the buying. It catalyzed the idea of sort of buying an internet native solutions, right? You think back to the story of Microsoft.

46:56often. 95 Bill Gates wrote sort of the Paul Harbour member of like we need an internet native kind of like strategy to write it was a catalyst for consumption and sort of change within those organizations more so than most but none of them are perfect. The reason why I think mobile is a more flawed way to think about it is that mobile really was the same architecture and business model as what was before it. The way we architected applications didn't really change. The business models associated with them was pretty much the same. And those things can really lead to disruption, can lead to new startup competing.

47:28And most of the incumbents before mobile were the successes in mobile. For the new people that won really took advantage of native consumer experience with a ton more time that got unlocked by mobile because mobile unlocked a ton of consumer time. All of what was really enabled by GPS on mobile. And so you get Snapchat and Instagram on the native consumer time getting unlocked, but it was kind of the same in that way. But we're really going to look to us geolocation services so things like Uber and DoorDash. You might also argue if you want to get really specific, that gaming did get really unlocked by mobile and it was because a whole new business model really got supercharged, which was free to play as a distribution strategy mobile again with consumer time.

48:10Unlocked a huge amount of consumer time, so distribution into that with a free to play mechanic that could change. The internet though really changed the architecture of business model. We went from on -premise license -based SaaS, used to install it, you managed it to SaaS 1 .0, which was we managed it for you by monthly access to it. That forgot Cable becoming Salesforce, that forgot people's soft becoming Workday, and that was total disruption. There was an old architecture and an old business model, and we have a new architecture and a new business model. You then unlocked with that new business model, an ability to reach new segments that wasn't maybe as possible.

48:43Before SMB starts to open up, you get things like HubSpot, ProSumer starts to open up, you know, just say, for you get all sort of PLG companies. But that's enabled by that architecture and business model. And I think if AI is to be the force that it can be, I think you will get a new architecture and new business model emerging from it versus what we only see right now, which is kind of a sustaining architecture, which is just that of a co -pilot, which fits on top. What is the new architecture and what is the new business model? I think the way to encapsulate would be this idea of selling the work not the software.

49:17And it will move from a paradigm where you might think of it as moving from what we see right now as a copilot and moving to what I think about as a control center, where we'll sell an SLA on work, not an SLA on uptime. And so we'll move from a world where we all, as users of software, kind of like monkeys doing data entry, usually like most most software, it's a database with a form on top of it for users to manage information, put information, and get information out. And so an example is you set your objectives on your marketing spend and what you want in terms of cacking up TVs and then actually as marketing efficiency engine will go across channels spend and deliver you back results.

49:57The stab might be an example, right? And so we'll move from a world where the users are doing all this work to a world where the application is doing a lot more of the work, right? Where the AI, the notion of agents inside of it, etc. is doing it. And we're right now, like you would have any SLA for any software you get up time, you get support SLA's for questions and things like that. I think there's a world where in the future where like an SLA maybe almost looks more like a BPO would in some sense. An SLA will be you wanted a efficiency of X on your market, we delivered that. You wanted this many leads from an SDR team like we do that.

50:31You wanted this sort of accounting and books closed by two days at the end of a quarter. We'll give you an SLA on that, not on the software's up. You'll go from copar to controls and it'll be a UX for a worker, which is dominant to UX for managers. You'll go from a seed add -on to software and labor, and you'll go from SLA on like the liability to SLA on outcomes on work performance. That's what can be offered up by this. You see very little of it so far. I think it AI is offering the potential for that architecture shift, and if we get that, that the whole seat model, the whole of the work, it does it in the product paradigm, the distribution in terms of who you can reach changes because ACVs change.

51:11And in that way, I think it will be very different to mobile, which was mostly another UX, but the same architecture, same business models. Do you think the supply side is ready for that business model change? And do you think the demand side is ready supply side, obviously, being the providers, the teams that we work with? Or do you think they're just layering on traditional science models? And do you think actually the buyers, is large enterprises, I think about a new business model for the technology that they buy. Most of what we've seen has been co -pilot stuff. And I think co -pilot is an incumbents strategy.

51:42Incumbents own distribution, they own data, they own the UX, and they own a business model that all aligns to a co -pilot. Co -pilot has GitHub co -pilot, right, like in line, suggestions, think of it like how most go to any Microsoft product right now. Every Microsoft product now is a co -pilot experience instance of a sidebar, an auto fail, things like that, right? Where the UX, the core product, it's a layer on top of it, right? It's immediately added in, which is also totally incumbent strategy. And it's still about sort of supercharging that work, but still where every user has a seed and every user doing most of the work.

52:15And it works probably, you know, if you think about the evolution here, the models, most of what's rolled out, might not be good enough for some of this yet, right? But that's what will come around the corner. You know, if you think back to Salesforce, disrupting Seable, Salesforce launched like five years after Netscape launched. It might take a moment for that to happen, but the co -pilot, this idea of, I'm still the pilot, I'm still the user controlling everything, and it's giving me assistive suggestions like GitHub, co -pilot, fits into the UX of incumbents, fits into the business model, having incumbents, and they already control that distribution.

52:46The opportunity offered up to a startup, being a co -pilot for something else probably won't be that amazing. There might be pockets of it where it can really work, but the opportunity to disrupt is to be off for our gnal to the incumbents. Right? Not a UI, we're sort of a transitionary period. And what I mean by that is I saw a company the other day that's I'm just changing it to say AI for legal, where it's a copilot for anyone in the legal industry. But then through the proprietary data acquisition that they get from different user inputs and different user modeling, they're able to then sell the work over time, or they say they will be able to.

53:21Is it a transitionary period where you do copilot to then be able to sell the work? or do you think we'll see a shift? I think there's so much holistically in a company that gets wrapped up around a business model, right? And if you have a copilot business model, your product is wrapped up around that way, your distribution model is wrapped up the way, that way sales education is wrapped up around it. And that's why I think business model, which encapsulates product and distribution and markets, if you can be orthogonal to that, to an incumbent strategy there, and obviously you have to be correct.

53:51It is the means being orthogonal to an idea idea that you would have a UX not for work or UX for manage it, the idea that you'd sell work and outcomes not software, right? Like at the idea that you're sales force, right? Selling cloud subscription managed by us for a seabull selling an on -premise license you install you manage you get cash for like that's orthogonal, right? There's so much wrapped up in the art fundamental business is in company architectures and all the systems internally and all their operating around that that it's really hard to just change. That's why it's ends up being asymmetric competition.

54:22It's not to say they can't and they won't, but it's a lot more painful of work to be done of organizational change to enact. And so I think a startup's opportunity is to build their strength and build from scratch that strength in a way that is really orthogonal to those incumbents. And I think it's this idea of this more all -encompassing change in architecture and business model that AI enables in the way that the internet really enable to totally, you know, enable SaaS 1 .0, enable it to totally different architecture product model and business model and distribution. Do you think in Convent see this?

54:54I think in Convent can have a lot of cake with a co -pilot idea right now, and that'll be the focus. I wasn't around for it, but when Salesforce launched, I think there'll be some entrepreneur, or if you want to, in the coming year or so, let's say, who channel maybe the Mark Benioff 1999, like No More Software. If you sort of study that time period, Salesforce Benioff like, picketed outside of Seabull's conference right no more software end of software right was a rallying cry I think there'll be someone who will who will channel that in the coming year it looks small it might start in SMB's you know it might start in people who couldn't hire workers to do some of that and instead of the upstarts the challenges and so in that proverbial like it looks like a toy to start it might look a little that way but I think it is the mental model and a strategy that encapsulates a more holistic to attack, to steal shit and expand market because I think this is a way for a market to expand that relative to every incumbent is doing a co -pilot.

55:52Well, we think about adoption. I think the biggest thing is that you mentioned Slanky Aryan and Spandons like in particular, there are so many companies that have never heard of Slank, especially in Europe. The reason I say that is because I think we especially in the tech space and doing what we do, think so much further ahead just by nature of what we do, I think people will grapple with go copilot for 10 years and to price side. If that's the case, investing in selling the work will be a massive market timing problem. First of all, you don't need as a startup too much market or too much market changing hands really fast can be dangerous.

56:27As a startup, you could only take on so much. You can only grab so much market share and the grand scheme of things. And if there's enough market being dislocated up for grabs in a year, for you to fully satiate yourself quite frankly in that year in terms of what's possible and you get that sticking as that's how your power crews. 60 % of the available market share, 60 % of the market share, 60 % of the market share, and over 60 % of the time is a bit bigger absolute number and so that's all growing. And you look back and suddenly of the market size of the now he's this for this sort of an offering, you've got like 60, 70, 80 % of it and it's locked in and you're the main vendor and you're going to get 70, 60, 80 % of the next year is available and anyone who compete with you can't get all that moved.

57:07And there's only gonna be able to try and compete you away for 20 % of what's in -commendative available. And you've got all of the cash flow from having won their customer, funding your innovation, your marketing and your work. And so how much is available is that enough to sort of chase yourself and building strength that way as actually all you really need is a startup? And two, I think this idea of sell the work not the software. We're all gonna have to retrain ourselves. Sell the work not the software, have an SLA on and outcomes not on reliability. It is gonna be a great for having a proposition.

57:35I'm sure since you run a very successful fun and media company you have a CFO and CFO Maybe if they're full time has external parties that do stuff for them, right? Imagine someone comes along with a brand you can trust, right? Where they say use me instead of that external firm for like half the price You sort of be negligent not to switch. Hey, you have to go do some of this work now and you've got it Okay, that's not gonna work But if I say I'm gonna my SLA will be on the same performance same outcomes Maybe better, but cheaper and more pleasurable to deal with, etc. Like I think it'll be a very powerful proposition.

58:10You worry about the side to where I'm at locations. I agree that we can see that. And actually, what a little toss that could be replaced early can take out quite a lot of work. Do you worry about that? Definitely. I think the human spirit is indomitable and like pretty good at adjusting. Not amazingly fast sometimes, but like we adjust and I trust it'll sort of work itself out. In that way, it creates abundance and I don't think we should sort of constrain the technologies pursuit of that. There may be consequences there in terms of redistribution and taxation and such of other things. And why about the abundant aspects when you think about the abundance of content that it will create in terms of the availability of people to create 100 short form videos from one long -wreld form video that suddenly expands your competition by 100 days.

58:52Then discover a really sickle problem and content to get a risk of problem. What's the solution to that and how does the next generation of media companies win in not wild by that alien from this media company. Facebook's doing a pretty good job. I'm happy to take your 100. There we go. And find micro pockets for it all. I do think, though, that trust, we'll forget it immediately, specifically, different building software. I do think trust comes into question a lot as a function of both imagery and language models. If any, investors as AI has a big opportunity, and many of them also say in comments or advance, they're just so do you think in comments have this co -pilot advantage, right?

59:23But I do, but I think that there's an opportunity for startups in this new architecture. But if they do say those things, I say those things, they should probably have an interesting late stage public company, even public company kind of like pick in some ways. So to the media on actually the New York Times is an interesting patient who's going to be the arbiter of trust anymore. You're still going to need new information and you're still going to need incredibly trustworthy. And I think for existing media brands, it'll actually be a good thing. I think as a function of LLM's trust centralizes and there's huge economies of scale to subscription businesses and advantages and so fun idea.

59:55but if we're in media, I think that some do put a buy on the New York Times. Yeah. Yeah, no, no, I agree with you. I think the interesting thing is just how do you think about a business model that works in a world of other items and content publishers? Because the other items don't want to be the content publishers, but they are in many ways. The public. And I've spoken to some of the largest news publishers in the world and they're saying, fucking chat GPT is taking all of our visitors. Yeah, yeah. I just think it's, you go spend some time with, which I have folks with big companies. is clearly a little media.

1:00:26And again, to this idea of a new architecture, they constantly go, but like, where was this pool from the database? And they're like, which database was this in? It's such a new mental model to break from. Is that normal because of libel, though? That's so much of like, especially news. And I spoke to the, we can't name them, but like, one of these media magnets in the world, and he was like, they'll never be able to touch us because libel. Put aside like, why you might think that way in terms of like, why that's a good thing for your business, but just mentally, The idea that this doesn't exist in some database somewhere that was queried when you put in that query and it retrieved and got that thing is like a total change in all Application architects how applications were mental models that we have but it's like such a break that I think is what is also exciting There's something that I just have to ask because there's a lot of like tropes that venture ambassadors are thinking about AI I say which I didn't often know how to respond to a lot of like They're all just rappers on top of large language models and just rappers on GPTAs.

1:01:22How do you respond to that? I think there are some obviously ones that are not that already, right? And so think about what's happened in some, I'd point mostly probably to imagery, things like mid -Journey or Runway or Mal and video and some of these other things, right? Clearly kind of not rappers in those ways. A lot of what has happened in SAS is certainly what you see the most of in the news because in comfort to doing is the co -pilot, and I think co -pilot is an incumbent strategy. Is that a wrapper around the model sort of in a way? I think they're doing a bunch of other stuff to it for this new application paradigm, but it's that.

1:01:55We at Benchbog are starting to see what we're really excited about. Is what we're just talking about, this idea of this new architecture, this idea of sell the work, not the software that you have an SLA on outcomes, not reliability, UX for the manager, not the worker, etc. to sort of fundamental change. And we're starting to see those ideas really calculate. A lot of it though is things that are kind of just becoming available, you do need better models for it. You probably need some fine tuning around it, fine tuning available to start up is only just starting to happen, right? You could have been a savant and maybe take it open source models, but the open source models weren't that good until you alarm a tumor recently.

1:02:30And so you were fine tuning, not good enough. Now you could fine tune better and fine tuners of service is available. or how to wrangle this stochastic thing is hard. People have kind of had like nine months to do that now, so it's still nascent in it all. And so when you want to sort of offer up a totally new experience in this way, you need time to figure it out, right? And so I think we're starting to see that, boots on the ground, more anecdotes of it. But in some sense, not surprised that we maybe haven't yet, right? Like go back to history. As I said, LA sales force five years after, you know, the internet came about, Even in mobile, you know, Facebook didn't launch a native mobile app until 2012, right?

1:03:10It was post IPO, wasn't it? I think the IPO was around, I forget where it was pre -oposed, but it was 2012. And so give it a take around that time period. You want a story of like Microsoft, Microsoft acquired no cure in 2013, right? Like, it's not just sort of fun history, but I'm not surprised if we just look at this specific situation in the factors that it might take a moment to really embrace what's fully possible with its new architecture. When I think that all job was invested is basically where do we think value will occur, most significantly, and then intersect with those opportunities.

1:03:42When I look at it, there's application where and there's infrastructure layer, and then I think about actually where do I think value occurs? I think it's actually more infrastructure layer for the time being, which is democratization of fine tuning security, democratized data acquisition for startups as well, and cleansing. Do you agree with me that actually infrastructure layer AI is what it's most exciting right now? We suddenly think that and then to the Lanching point that the idea that every developer is going to come to building AI native AI and able applications like Cumbants are gonna enable it new companies are gonna fill in bracelet and they're needing you tooling and new frameworks for that environment like I think is absolutely happening.

1:04:22I think in the arc of time if it is a shift like the internet was the applications. It might not look like an applications right in the way that we think of them but might look more like you know this control center idea will have profound amounts of value to them and will probably also pull through even better infrastructure in the way that Facebook became some of the biggest contributors you know to my sequel a bunch of open stuff like it pulls through the infrastructure that I think will be in the arc of time. Do you think the majority of dollars going to new AI I've managed deals today will go to zero.

1:04:53Maybe a bit to my common early on diet. Like I think there can be a lot of high -fruits corn syrup of adoption. Like there's an amazing magical moment in a while, right? When you go experience chat to you for the first time or some of the imagery models for the first time, that the rate of adoption of like signups to some of these things is just astounding. Some investors have been trained again with a data first, deal flow, rules, checklist mindset, there. And to the point of thinking about like some of these like are off the charts on some of those. If you think from that paradigm, like they're amazing.

1:05:28I think when you think about sort of enduring need for some of these and long term solutions, you can make the argument they look a little more like a high -fructose concerted diet. 2BD if they go to zero, right? Great teams will reinvent. Great teams will use that to maybe do something else. So situation specific, but I think if your mindset was a little more like it beat the metrics and other things. You always want to get lucky, but you'll definitely be hoping you get lucky, potentially an evolution of them. When it came to line chain, haven't that deal good down? I would say to a point earlier, right?

1:05:58Like more than half of what we do is the first partner, you know, probably a third kind of an inception, as one was exploring more of what was possible with things like sort of reacting to the agent ideas and this idea that every developer would become an AI developer versus just the ML wizardry. You know, Harrison, and very definitely without grandiosity, put out an open source library with the beginnings of abstractions for making agentic behavior and now a lot more around retrieval and other things easier. And we just started spending a lot of time together. Probably three or so months before we ended up actually investing.

1:06:29Talk about what was happening. We talk about his framework. We talk about, you know, sequence, it was sort of strengths to be building now, etc. and just build that relationship. And I never pressured him to say you got to start a company. There were some people who pressured him to say you got to start a company, but like that's going to be a founders calling. It's a real responsibility and so he then said, hey, I want to go do this and I said great. Let's partner You know, Prevulage Journey since you worry about too much money too soon I know they obviously subsequently raised another ramp pretty quickly after yours I saw a nut like what done?

1:06:57Look, gosh, do you worry about too much money too soon? Definitely we probably could have taken more Probably could take more now, you know, at Langtrain obviously like we have more capital than we need right now But the bottom next being like hiring great people and the initiatives we want to work on and that's driving investment and pace investment versus We have the capital so why not? Final one before we touch on my marathon, so I just have to set on so excited for that one. What do you think the venture world believes or sees that you think they've got wrong? What's a misconception that venture has about the AI world?

1:07:29About the AI world, and the current landscape. Everyone says to me, what I've learnt now is that actually the incumbents are going to win. I think that co -pilot isn't in common -scanement, we're seeing a lot of co -pilot, but I don't think I think that misses what is possible. And I think that the new architecture, a new business model associated with it, is starting to happen as around the corner to make work, will be very orthogonal. It won't be new distribution like the internet was a way to reach customs, it couldn't otherwise reach, right? Or mobile and say it's not going to be a distribution opportunity, but it'll be a real architectural shift and holistic company shift that I think great founders are starting to take hold of.

1:08:06And so I think that's the opportunity that's there that maybe is beneath the surface of just the co -pilot ideas. But if you just played on that, it's not a distribution opportunity. What if it is? What if you sell the work and not the service? That changes entirely the value of UI and it may remove or create a cousin between the device and the user entirely, which may create distribution opportunity in the real world. That could happen. I think I could also think it could unlock segments, which is different to sort of being the means of distribution, right? But the change of business, I'll say, might unlock segments that were previously not served as well in the same way that an architecture of SaaS allows you to sell to SMBs and do PLG in a way that's very different, right?

1:08:49Sort of SaaS 2 .0. And so that might be possible here, but unlike the internet, which literally allows you to reach customers through this one means in a way that you couldn't before, it's not quite the same in that way. But I do think it could be an catalyst for consumption and enable those new market segments to reach if you fully cut it and embrace it I want to talk about running we do a quick fight. What's your pre -run nutrition? Nothing but like before 10, 15 mile like weekend, hell run or whatever Yeah, and my secret to life is a chocolate croissant most days. Well, so probably a chocolate croissant on coffee Why am I not being read that's just shit?

1:09:24I've chocolate croissants are wonderful items and give great joy and And how could you be sad if you had a chocolate question each morning? Do you have a training schedule? No. I was very fascinated in high school or college by the question of like just how far can you go really? That book born to Rondin Kanazaz, the sport -coded adventure racing which is multi -sport -orientering. And I do like 60 hour races. I do like ultra marathons. I'd run 150 mile multi -day stage race thing. And so I was just really fascinated by how far can you go. and I wasn't the fastest for sure, but I usually thought I could outlast someone.

1:10:00I enjoyed all of that, and there's just a challenge of that question. I would spend a lot of time on nutrition in those days, so pre -race, the paleo diet was big at the time, so I did a lot of paleo diet. You've got to make sure if you're doing long triathlons, I did sort of like a half iron man, and I never did an iron man, but a half iron man triathlon. I'm out of salt you're doing and other sorts of things, I'd try and find like, I really ended up like honey stingers and brand for like jell and stuff. And so I spent a lot more time on that than the best person to ask now would be my wife who's a marathoner Probably like the hundred fastest marathon in the US like qualifies for the limper trials for women And she's like got all of the stuff down these days I've ever cared and I'm a recreational runner So I don't add extra stress for it by having rules.

1:10:44I just go out to enjoy it 60 hours you mentioned what you doing this was from Chris Pike What do you do when your body just says no? What does your mind tell yourself? So mine says just one step more. Can you do one step? What do you tell yourself? One more step. Keep going. Yeah, that's 60 hours we did. We're probably like 250 miles or so. You can go through two nights. And so the first night, you're in northern, northern Maine, like right by the Canadian border. One team actually got arrested because they crossed over, they got lost because you're in the woods with a map encompassed, no GPS.

1:11:13And one team got lost and ended up crossing the cannon or got arrested. We ended up in a small town the first night and a McDonald's opened up at 5am as we passed through and we slept on the benches of McDonald's for an hour. I've never felt worse waking up from that. And then the next night, there were sort of man checkpoints where there's staff and you actually physically check in and like if you're gonna drop out, there's probably a car that can take you if you're out later, like back to the town and other things. But there's some that they set up fires or warmth and stuff like that. So we slept on the ground and you do it as a team.

1:11:43So I had two teammates race, when we like spooning each other, you know, with an emergency, he blanket like on the ground for like an hour and a half and you never want to get up. But you just get up and you start walking or get on the bike. Yeah. That's what I mean. I mean that's just extraordinary. Listen, I want to do a quick fire where I say short statement, you give me your immediate thoughts as I'm okay. Great. Okay. So you mentioned that, you know, having your first child, what do you know now that you wish you'd known when you had your first child, you can call yourself up and give yourself that advice?

1:12:13I think we're all really relational beings. I've noticed myself, I think, change in response to my son I think he brings out a better version. He makes me more present. He makes me more patient and if you know, in part, he just doesn't give two crabs about what's going on with my day, right? And I think that's a good thing in many ways and as maybe a better person and I think the idea that my son unintentionally can do that speaks to sort of the relational aspect of humans and we're all doing that to each other every day in our own ways, right? It's made me more vigilant to, you know, how I show up to people and that.

1:12:49So that's probably how it's, I don't know, it wouldn't be advice for myself before I had it, but it would be the way in which it's affected me so far. What was most striking example of their interest right environment in your mind? I'm sure we could list out a bunch. I would say that the more exciting thing is how the leadership to learn from a house I've changed and reacted posted. And so we can all, you know, name the lists of the 2020 and 2022 timeframe and some of the silliness. But I think the more interesting lessons to learn is from how great leaderships react it. And so for Toby, it's Shopify to make an acquisition and then divest it.

1:13:27Within a year, maybe it was a year and a half, like not very long, for an organization to make a big move and say, nope, we made the wrong decision. That fast and not get locked into it, not get locked into the ego of having made the call and wanting to look right, but to be so true seeking to be able to recognize they made the wrong decision and correct it at that scale. That's something for everyone to learn from. Changes like this offer the opportunity, I think, to take lessons like that. Which less well -known firm do you most respect? He might hate me for. He's so less well -known by intention that mentioning him and may piss him off, but I hope not.

1:14:05He used to be at Sakura and Ensakura has a full website with lots of information and and every investor has a profile with questions and he never did the questions and I think has just said, get in touch. But he is both a great investor and has taught me a lot. I've been very kind to me. So I have a lot of thanks and gratitude for him but Michael Abramsson and he's able to do back of the envelope math to sort of distill complexity into the few things that matter and have real clarity of thought. I've learned a lot from him on that and by example, and so I'm very grateful to him, he tapens to now a firm.

1:14:36So he fits your question but that would be the person. Who's the best ballman that you've started on a ball with? My partner, Eric. I think there are two expressions in venture. I don't like and think differently about. And I think he embodies the way I think you should think differently about them in a context of a board too, in a relationship. One is founder friendly. I don't think you should be founder friendly. Not do you shouldn't be friendly, obviously. But I think the higher purposes like founder respect. And friendly can imply like cheerleading, being yes, person, etc. to auto and respect a great founder means sharing truths.

1:15:10Maybe not saying the easiest thing to be saying, maybe saying the uncomfortable thing to say. That is respect. So I kind of like found a respect and found a friendly more. And the other would be, I think first call is a very reactive mindset. So VentureWare is talking about wanting to be the founders first call. I think it is first to call and being proactive, right? Obviously not obnoxious. It's not your company, right? But being proactive versus This is just reactive. First, call implies lots of reactivity. I think Eric is, if you looked up his phone and looked at who he's called in the last couple of days or whatever, he'd have called a lot of his founders and maybe with ideas, maybe with follow up on things, but being active, proactive and having real respect for their greatness and what's possible and so deeply come into that.

1:15:56Magnum's steak his hands are not on the steering wheel. He's like in the pit crew and the founders very much driving the car. But I think the trust he builds and the manifests to that point of helping founders make great decisions to sort of dent that curve I'm very impressed with. It's been the hardest part of getting used to the benchmark partnership. To the point of having deep curiosity, I can't help myself, but sometimes think about later stage things or like flexibility probably comes with the curiosity in many ways. And entirely, Right? Having one main manifestation of that channeled into early stage partnership.

1:16:31There's pain in being focused in a good way, right? Like I think Steve Jobs has famous saying that I really like, which is you only know its focus when you're deeply troubled by all the things you're not. You're saying no to where they feel like such good ideas, but you're still saying no to them. Speaking of Toby and responding to Zub, I think he also said like, The main thing is keep the main thing, the main thing, and it's really hard to do. The force is excellence and is productive pressure. So that's probably the biggest thing. Final one, Females, was the most recent company investment, and what did you get so excited?

1:17:04Lankshin, there's tens of millions of developers becoming AI developers, and it's sort of a new computing paradigm. Right? Like it's not retrieving from the database. It's generative, and the framework to build AI apps for every developer, and the tooling around that new paradigm is the focus. And I don't know, you could look back to, you know, if you want sort of trying to analogize recently, you know, you might look at things like next jazz and for sale, you know, in that journey, if you want to go to the past, you might think about rails and things like new relic around it, which were tooling and monitoring.

1:17:36You might analogize and think about things like DACA, which made a lot of development much easier by DACAizing them. There was a new framework for doing it all and empowered. I think there were quite literally tens of millions of developers with, you know, darker accounts now, a way of building applications containerized, that will happen for AI apps and I think that's the exciting opportunity to chase. I mean, this only took six years to happen, so thank you so much for joining me today and it's been such a pleasure, man. Thank you, man. Good to have you. As I said at the beginning, I met Miles seven years ago.

1:18:08He's been a dear friend and supporter of mine ever since. I so appreciate the relationship that we have. If you want to see this show and the full episode in visual you can find it on YouTube by searching for 20 VC, but before we leave you today, this episode is brought to you by Tegas, the go -to research destination for bold investing. Tegas curates expert in -size analysis and financial data to give you powerful perspective for your investment decisions. With lining fast access to over 60 ,000 transcripts across 20 ,000 companies, you'll discover a wealth of unique insights to fuel your fundamental research, gained perspectives, synthesised information and even model outcomes all on Tegas.

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