Benchmark General Partner

led investments in Airtable, Monzo, Lattice, GitHub, Segment, Slack, and Benchling to name a few. But before we dive into the show’s

A pleasure to finally do it. A long time coming.

Worth winding the clock back a little further than just that, sort of where the motivation, the inspiration kind of in in incepted in many ways. I actually grew up in The UK. We’re here recording in The UK. And I went to The US because my parents remarried. And my stepfather, who’s very much a father to me, was an entrepreneur. He founded one of the very first ecommerce software companies, taking that public in the .com. And when we moved over to The US, he was starting another company out of our our living room, our our kitchen table, actually.

And it was, like, two people, him and a friend, and then three people, then four people, and five people. And I didn’t really know what it was in many ways, but it was, like, really inspiring to come home from school and see him working with friends and working hard and talking about new ideas. It was ecommerce software again. And so at that point, in many ways, the American dream was his lived experience. He’s a Korean immigrant. American dream was sort of mine, in some sense, coming to The US from The UK.

And that love of being around people like him and his friends who were creating kinda just got into the blood in many ways. And then fast forward, you know, I didn’t know what the job was to to do things with those sorts of people per se, but I knew that was really intoxicating. And fast forward to tail end of college, New York City and sort of app development, you know, was having a really vibrant moment. In some sense, it was sort really early in cloud, obviously.

This is, like, 2010, 2011, 2012. So it was, Tumblr days. Tumblr days. Four Square. Four Square, you know, in New York City at the time, Warby Parker, Harry’s, Mapbox, GroupMe, and a number of others. The movie of the time of inspiration was probably was the Facebook movie. The Social Network. This is what inspired me to venture. Yeah. Exactly. The idea that, know, you could be a kid and you could build something in college. You sort of felt like you got handed all these superpowers and could use.

And there was this question at the time of, could you have a Silicon Valley? Could there be tech built outside of the Valley? And I was on the East Coast. I spent a lot of time in New York. And I got to meet Josh and this guy, Will Gaborick, and they were sort of setting up Thrive. And we just started spending a lot of time together, talking about ideas, pursuing them, trying to help founders. And it was infectious, that excitement. And so they invited me to join the team as I finished up, serendipity met, and been running ever since.

One would be, I knew it at the time, but if you don’t have as much historical context, it’s sometimes hard to necessarily really fully appreciate the wave in terms of context and history and specialness that you’re on. If you go and look, call it 2012 to, like, twenty twenty two ish time frame, cloud spend went from, like, 10,000,000,000 to $3,400,000,000,000. There’s a chart that, you know, the banks put out. Right? It’s sort of like McKinsey. This is AWS spend and, you know, Azure spend they cut, so and all of the cloud SaaS.

Like, 10 to, like, 300. But over that 10 period, that’s what happened. And that is just a tectonic shift. And I knew I was spending a lot of time in cloud developer products, cloud application products. But, you know, I remember at one point, wrote this sort of analysis of, like this was before they went public. Shopify versus Etsy. And it’s funny enough, actually. Harley, the COO of Shopify, actually emailed me, cold emailed me, having read this little post saying, hey. You wanna come, like, work at Shopify?

I was at a conference the other day spending some time with him, and I showed I reminded him of this, and he dug up the email. He was like, yep. You know, I was like, it’s a lesson I give to so many founders now. Like, you should always be proactively recruiting. This was 2014, and so it wasn’t like Shopify was small anymore. So it was be practically recruiting. But anyway, with Shopify versus Etsy, there should never be a versus. It should just always, in some sense, be and.

Like, there was there was such a big force that so much was still coming online. You tell yourself, don’t try to be too smart in many ways and some of it all. I am so with

Absolutely. And obviously, there’s relative in it. But the element of, in many ways, all of these were still sort of being first. The thing I remind myself if it was 2013 and 2012 again is, like, it’s so early in all of that. I think another connected, though, to that other piece would be advice and sort of reminders I give myself always, but reminders I give other people really getting into venture is there can be so much terminology, so many frameworks, SaaS metrics this, at MAO, DAO ratios that.

Do you feel like there were all of these kind of rules and vernacular and jargon? The most important thing is always who’s the user and why do they care? And if you ground yourself in that always, instead of sometimes whirlwind of other framings from investing, it’ll probably serve you pretty well. Certainly, company I recommended to, and all investors should sort of do it, is that you get started with investing books, which are useful, obviously. But the book, like, Working Backwards, which is about Amazon’s culture, which is working backwards from the customer, serves all teams well in almost all cases.

And in investing, you know, that simple idea of, like, writing the product launch announcement, like, there’s a version of that in many ways, working backwards as an investor where if you lose sight of the user, you get lost. That’s that really should be the tether to reality, and that would be a big constant reminder and certainly emphasis to an early investor.

Maybe I’d say three things that jump out to me as lessons from Josh. And one from Josh would really be kindness and competitiveness don’t have to be oil and water in business. And sometimes the cliches treat those as, you know, opposite poles of a magnet. You’re either, you know, pushover or you’re, you know, doggedly he really showed that they can be in harmony, and that’s a really special thing. So kindness and competitiveness. Another would be sort of this idea, like, yes. You can. Belief in someone’s potential and someone’s possibilities is such a amazing gift.

He suddenly gave me that gift, and I’ve watched him give many others that gift, many founders that gift of, yes. You can. Real belief in their potential. It’s a beautiful thing to give someone, and it’s an amazing way to go through the world and keep with you.

I think an appreciation of wheel over skill. It’s really a gift of a confidence in someone’s work ethic and determination. And, yes, they have to have the mental capacity and the intellectual capacity and all those things. Right? But you you can know that in someone. But the person who will love it and is passionate about it, you know, I have six younger siblings. Sometimes I think about what lessons I’d like to potentially impart as I go sort of on them, and and you think about these days, everyone talks about follow your passion.

And I kinda believe that for sure, but I believe it for the reason not where everyone else necessarily talks about it, but you should follow your passion because you’ll just work harder. If you think about compounding ten extra hours a week, fifty hours a year, five hundred hours, you know, not far into the future, you’ve learned more, you’ve caught up, you’re, you know, you’re better, and you’re always improving yourself. And so that belief in, yes, you can, that belief in sort of will over skill in many ways, leads to a really powerful compounding of individuals’ abilities.

it. Yeah. I just saw a quote, I think, of Stephen King on writing. The best it’s not that they’re necessarily better. They just start.

The third one, again, the greatest gift to things you sort of carry with you as ways of being, what I might call impatiently patient, a duality that almost shouldn’t exist. Why not now? Why not yesterday? Like, hyperactive all the time, but still a really high standard and really patient for the long term? And so that combination of fully present, fully engaged, new and active, but also, like, high standards and not rushed. And that duality, he really lives. And having a a mentor like that early on who can show you that through their lived experience is a really powerful thing to carry with you.

Yeah.

There wasn’t sort of, like, entry indoctrination or, you know, or whatever. In many ways, it was probably like, you be you. Be you totally kind of unfiltered and as authentic as you are, and and the best version of you will be the best investor. Trust in that. And I think in many ways, when you get rid of structure, there’s no, like, level to be had or nothing like that. Just be yourself is, in some sense, the hardest. And if anything, you’re sort of the freedom and the push to really be there.

Well, we have no deal flow list, no sheet, there’s no memos, there’s no data room presentations, there’s no agenda, there’s just a time block, conceptually about 10AM to about 3PM or so, and we just hang out. Bizarre in some sense. You’re used to you know, in any other format, any other company, you might say, who owns this meeting? What’s the agenda? But it’s a chance really to come together and share the learnings from the week, obviously talk about new opportunities and new things we’re seeing, inviting entrepreneurs to come and meet with us.

But there’s kind of a trust in free flowing trust in each other and a trust in just having that time block and therefore learning in it together, sharing in it together. And if something’s important, we’re gonna get through it. We don’t necessarily need to put it the agenda. So in many ways, very different, but very freeing in that sense.

I call them the five s’s. Because you mentioned four, and there’s actually a fifth.

So it is. You can make it an s. Sourcing, selecting, signing, supporting, and then I think of it as summiting. There’s no such thing as an end summit, a peak summit. You could call it separating. But, actually, there is it’s only a great investment at some sense when, you know, shares are distributed to a broader shareholder base in terms of distribution or the like. In the push for forever funds and forever, you know, people forget that an investment actually sort of is consummated at some point.

Maybe not the company, obviously, is not finished, but that’s the responsibility. The piece I like the most of those is really that connection of spending the time on connecting up strategy into sequencing of the company into sort of structure and organization to operations is that work of specific company thinking and execution. I really do think that starts and there’s a harmony between that notion of that sort of in diligence and getting to know someone and and the work afterwards. In some sense, we make a full total commitment, and so we’re not reassessing.

But you’re constantly working on strategy, which is that work of selecting in many ways. And in diligence, I think it should not feel like an examination. It should feel more like looking ahead at the future together and stepping into shoes together, which is a sort of work you’ll be constantly doing with a founder. It should feel like planning an adventure, not a colonoscopy. And I use planning an adventure because when you plan an adventure like a real expedition, there are serious topics you’ve gotta grapple with.

What are your resources? What are the plans? Like, which people do you need on the team? Like, on the side helping, you know, maybe an HQ and sort of back it down the mountain. Like, this real serious questions that you have to grapple with. And so it’s not like you shouldn’t take it seriously, but it should feel like planning an expedition, which is the work you’ll keep doing, versus that examination. And so that’s really where I get my energy.

I think you can create even if it was at a short amount of time, you can create that feeling. When we’re our best, every founder who spends time with us should really be able to say they got a lot out of that meeting. And I’d encourage all founders to take advantage of us. Right? Like, sometimes, I’ll only pitch Benchmark when I got the perfect pitch. Like, that that’s silly. That doesn’t need to be the case. We’re also unique in that you might end up pitching other investors multiple times because they have growth funds across it and all this other stuff.

We’re only early. Then you get sort of a chance of it, but also we’re not gonna rejudge you in the future based on what you told us now, whereas other funds might. And so take advantage of us, and it should feel like we really work hard in the spy to have it feel like the founder got a lot out that meeting. And the way they get a lot out of that meeting, hopefully, is you really stepped into their shoes together. There’s a certain amount of, obviously, context you’ve got to assimilate quickly.

Right? Like, what what they’re working on, who their customer is, who who their aspirational customers, etcetera. But very quickly, trying to move to being in the shoes together, planning that expedition, looking forward. And, of course, you don’t know exactly how the expedition’s gonna go and the metaphors. But, like, it should be looking forward, not an examination of, like, state of today. The the examination of today is only a means of of sort of taking stock to think about where we’re going. That’s the experience that should be felt, and I think you can feel that and and engage in that in any sixty minute conversation.

And if it’s great, the founder, you know, should say, let’s do more.

I certainly think it is a challenge. I’ll share two thoughts around it. One is a fun story and then how to how we think about, in some sense, the very best founders. That was a fun story. We had a founder came and pitched us, came to the partnership, and presented a while back. And we were talking we were talking about strategy going forward and how to think about it. And one of my partners sort of goes, oh, when you think about kind of the LTV of a a customer, the important thing might be to and the founder goes, sorry.

What’s LTV? And you might say, wow. That’s, like, kind of embarrassing. Like They didn’t know what LTV was. Yeah. But they’re an engineer, and this was a company in its infancy. But the fact that they’re willing to say, I don’t know, and quickly learn and grok it is really, I think, like, the most important thing, that rate of learning. And in fact, I’d say most of us saw it as a strength after that pitch. It would be easy for us to say, speak of imperfect pitches.

Right? It’d be easy for us to say, that was like a no go. They don’t know what that is. They haven’t lived in that world, and that’s okay. Like, they’re gonna learn it fast. And I think the rate of learning and the willingness to engage in that discomfort. Right? Learning is an exciting thing, but kind of an uncomfortable thing to be not knowing very much. And my partner, Eric, has this great saying, which I really like, around this, which is that the very best entrepreneurs are always making mistakes.

The really great ones are just making new mistakes each time. And I think there’s a lot of truth to that, and so that slope and pace is the most important.

It’s not acceptable. But, you know, regardless of whether we did or didn’t make the investment kind of thing, we we won’t share anymore. It’s not a binary condition for me now. There’s all sorts of situational costs. If the person’s 35, okay. We’ve got a different situation I have. Right? They’ve had thirteen years stereotypically in a career at that point. If the person’s 21 It’s different. I get you. And they’ve spent their entire We’ve come out of university there as CS grad. Grow doing CS and then an amazing engineer.

And if I went into their world on architectures, languages, frameworks, technologies, I wouldn’t know some of the latest stuff they might know about. And simultaneously, though, if someone was dismissive of that idea, right, of customer retention. Right? If they were dismissive of that idea and didn’t care for the concept, obviously, or whatever else, okay. We’ve got a problem. If they know that to be true, just don’t necessarily know some of the terminology yet because they haven’t done that, and they’re willing to acknowledge that versus hide it, that’s a superpower.

If you were to pocket it, I’d then say it’s selecting Yep. And supporting. And that’s where I derive all my energy and and and spend all my time. Do you think VCs really add value? I see the aspiration and and the job as really helping a founder make the very best decisions. It’s always their decisions, and it’s them making the decisions. A couple really important decisions over the course of each year times 10 over the course of ten years, round number. You move those odds a little each time, that really adds up.

To do that, I think you really need trust. Trust is the foundation of that. To do that, I think context, high amounts of context and high amounts of high bandwidth communication really filters in. Without trust, though, you can share stuff, and they’re never gonna listen. They’re always gonna doubt it. So but I think trust with context, with high bandwidth communication, tilting those odds each time, leading to a more successful company through their decision making. But where they’d look back and say, that partner really helped them get clarity, maybe helped them see slightly differently, that that maybe added more clarity, slightly tilted a decision, I think really happens, and that’s certainly what I aspire to.

I’d say two. One, you should always have the Hippocratic Oath. Do no harm. I’ve been in some board meetings where investors don’t really get the product, don’t really get the strategy that has to be pursued. They’re trying to 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 burden for the founder. And so, yeah, Hippocratic oaths. The second is, though, I think that it’s not that you always have the answer. Part of it is a founder trusts you to say, I’m working on this and come to you with it, and you go work on it together.

I don’t think you have to always in fact, it’d be dangerous, I think, to assume you’ve always got, like, the perfect answer and opinion and everything so much as to say, with that context, with that trust, with high velocity communication, you can go work through it.

They will have done great things absent an investing partner. Sure. Can it further supercharge that? I think so. But you can’t coach height. 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. Go look at even the very best. Go look at Jeff Basil for it. He’s still got a board, and he’s still got partners who’ve been with him that entire journey.

This sort of pageantry of signing, winning, whatever, is if you think of investing as betting Sure. I think you spend a lot more, you know, a lot more energy on the funnel and and winning the first like, you’re placing chips on a roulette table. And I don’t think of it that way. I really think of it the work we do as as 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.

And I think if you listen to many people in the industry talk, you’ll hear the word bet. I bet on this. I bet on that. You know, that’s a bad bet all the time. And 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 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.

It’s the integration of it all.

Yeah. I’m comfortable doing it. And in fact, I I used to do more growth investing, later stage investing. Yeah. 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, product and customer, not data. And 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 early stages, like, data can be a trap. And I often say with companies I work with or companies I’ll meet with, like, that 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 wanna prove in the year? What do you really wanna have learned in the year? What what would be the right customer adoption in the year? Often cases, I’d rather take less growth in the right ways than more growth in the wrong ways.

So I so I don’t personally see it that way.

can’t ignore it by any stretch of the imagination. Sure. But when you’re in these early stages, and I 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. Other success can certain revenue can be empty calories. If you think about it as a diet, like, you wanna make sure you got a good diet, not empty calories. And so, anyway, back to, you know, 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 exec interviews as they change exec teams on that journey, between individual ICs that I might help out with early on. If you then add in other investors you’re gonna have talked to about the company, you’re gonna have, like, pitched the company hundreds and hundreds of times and suddenly just apply it 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. So the mission matters. Like, who are they working for matters, and the team, and it’s called and so that, like, a recruiter’s thinking about it in a holistic way. And so we actually just had a partner meeting the other day. One of my partners was at literally did 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 a new investment? More with investor speak. I think the biggest one is what’s changing? Where is there a gap? What’s new either from their perspective? What’s a gap in the market that’s opening up? And change begets the opportunity for new, begets the opportunity for dislocation. And then you gotta have a founder who is authentic to that, a strategy that can get on the field and work in interesting ways with that business model that you think could be valuable upon success within that.

But that change or the ability to for 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 You might call it that. Yeah. 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.

I think it’s dangerous to there’s sort of, like I don’t know. If you go back to sort of philosophy and economics, there’s this idea of, like, normative versus positive. Right? Normative, how things should work. Positive is, like, how they do work. And I think it’s dangerous in many ways in investors to to think, oh, the 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 for cracking that open, there’s not a dislocation that opens up the window for that to happen.

And 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 of 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 Coming back to the 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 them, 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 gonna feel like the dominoes got tilted over. You know, you’re looking here, but the domino chain is is sort of happening conceptually in the market. And so I’ll I’ll sort of happily take that and go on that journey if you feel like the dominoes are start you know, really falling.

Yeah. We do we do a lot of that. Hey. Come join this. Hey. Let’s go meet together. There’s ultimately one person who takes a board 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 the whole partnership, but, obviously, they’ve they have a principal relationship, a dominant relationship with one person. But we’re we’re constantly pulling each other. And, actually, just before I came here, a founder who works with Bill Gurley, I’d 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.

And so we’re, you know, we’re always pulling each other into current investments, future investments.

We really don’t think about it very much. If you would hit the spreadsheet of our investments, almost all the capital we invest is the very first time we partner. And, yeah, we have reserves. Tough times happen. Yeah. Or 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 that’s what we’re doing, or we’re not in.

And so we don’t reserve with a future investment orientation.

think it’s something like 60% of all the investments we make, we’re the first partner. 30 odd percent, we’re, like, literally the first investment. You know, we don’t use the term incubation, but, like, I think probably about a third of investments all at inception. It’s not to say that’s really the focus. There are occasionally exceptions.

Like, I don’t think it’s zero sum by any stretch of the imagination. The n of that in a given year, even for that percentage, is, like, three companies. Right? And so it’s not like we’re doing 30 that win. So the n is small, and there’s a lot of new companies formed each year. I don’t think of us as competitive. I think to a 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.

Yeah. I think if you realized, it’d probably GitHub or Segment. If you look at unrealized, maybe Benchling or Monzo. And so Benchling or Monzo, it’s funny. You learn two 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. If you want a positive feedback loop to small but growing markets with, you know, high degrees of market share in them and have found a perfectly match to dominate that market and what could be possible.

It gives you a feedback loop for that lived reality. Monzo, the exact opposite in many ways in that is banking. You know, it’s a UK for any outside The UK audience that might not have barely heard of Monzo because it’s a UK phenomena. But in The UK, there are something like sixty, seventy million core checking account users in The UK. Monzo now has 7,000,000 accounts. It’s like a tenth of the British population has signed up to this thing. And both of these, by the way, like, Benchling was five people.

Monzo was probably more like 30 people, but about, like, 5,000 Yeah. Maybe, could have 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 hold back, all the elements attack on a market can break through in ways you that are 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. Like, there’s so many marginal and and incremental decisions a team makes, 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.

The greatest regrets I have were I thought someone was really, really special, and I got too hesitant on market.

I’ll give you three. Dylan at Figma, Zach at Plaid, and Alex at Scale. Got to know all three of them really early,

Yeah. I spent time with Dylan at the round that Kleiner ultimately did. Also, again, at at when Sequoia invested. It is definitely the one I am most mad at myself for. So I’m thinking about the hesitation I had, I didn’t think designers was a particularly large n. I think if you went and asked how many designers were in many of your companies, suddenly relative to engineers, it would be a tiny fraction. I think n of designers relative to accountants or some later stage startups would be tiny.

So what did you miss there? What I missed, the adoption brought far more users into the product. And I know I conceptually knew it, 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 copywriters come in, marketing people come in, product managers come in, engineers need the handoff.

There’s a lot of people that orbit that asset inside of a company, that workflow inside of a company. I was, like, stupidly, myopically thinking of it as a design seat, as design software. And what I should have been thinking about it is the nexus of collaboration for digital product, of which design is the core stakeholder, but all these other people orbit it and are very involved. It’s if you go and look at the data at the time, it actually was there. It was in front of me.

Sometimes maybe not being data first enough is a miss.

Dylan had showed charts. It didn’t sit in my mind properly enough at the time of all the other nondesign users inside the companies using it and them 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 is was wild to think about, and I would never have guessed when you think first principled 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 from my surveying has paid seats inside of Figma, and they pair out three times as much as they would for something like Slack.

And 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 cause for a lot of excitement and and suddenly to be a student of. And I like to think of myself that way, and so it’s the one that grates me the most because it was right there when I didn’t wear it enough.

This to me would be a 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, they just can build an OAuth system. Conceptually, the way the world should work is every bank, and this, 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, that’s all you need, two numbers out of them to authenticate. In my mind, it should work. Then now 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 a bank works. And so no bank has an incentive to actually offer this.

And so, again, you think user first, you know, incentives in the system. It sort of shouldn’t work like this, but it’s not a complicated technical product, I think, asking, so it should work like that. And I got too intellectual about it. And, again, amazing founders, like people I feel lucky to still call friends and just people who even then I I knew I wanted to just work with, and that’s the magic of this journey. So those are those are the big regrets.

Yeah. Firstly, I can’t help myself. Maybe, you know, too much curiosity. That said, I thought I had a lot of curiosity, and then I really got to know my partner, Fenton. He I think he has, like, clinical curiosity. Even my curiosity has a ways to go to catch up. What

Yeah.

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. But I in some sense, well, have I why the breadth? It’s just curiosity pulling me into different places. And usually, in many ways, founder driven. You have an inkling of interest in an area, and you meet someone like Tom. And you go, you wanna work with Tom. You meet someone like Dylan.

You meet someone like Zach. You meet someone like Socket at Benchling. In some sense, I think myself as sort of generalist, really ending up being a specialist in helping founders like that accomplish their dreams to make the very best decisions. And and I think of myself as becoming a specialist in in not in the same degree, but in many ways in their companies and their situations, and a specialist in helping them connect up that strategy and vision into the sequencing into 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.

There are lessons absolutely learned from the past, but I don’t think it’s a stamped out assembly line process. Right? Stripe is not PayPal at Segment. There was a lot of pressure to and we did also in the positive way learn lots of lessons from Stripe, but we’re very different to Stripe. And too much of the Stripe lesson was detrimental actually to being the best version of ourself. And so I don’t think greatness is a carbon copy either. And so 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 but it’s about applying strategies and learning from strategies, not learning procedures.

And I think the more you become a theoretical specialist, well, the more the temptation is to say, here’s a procedure. Here’s a checklist. And I think the very best to not that. I can’t help it.

Yeah. Absolutely. But I think, hopefully, it can help people get connected to to those people for those expertise if that’s really what makes it. And there’s there’s a lot else that goes into building a company, and there’s moments probably where those metrics are the wrong things. Right? Like, we’re benchmarking perfectly to the playbook of that vertical. Like, you’re gonna break it in some way. It’s gonna look different in some way. The generalist being a biologist versus a physicist. And I think the 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, new variants, and curious that, which is why the Figma thing annoys me so much of myself. Right? It’s a new adaptation. That’s the sort of psyche one applies it to. If you wanna deploy capital, being a specialist is probably good because you say, hey. I If pass enough of these rules and I have a lot wide enough portfolio, it’ll be good enough. But I just don’t think like that.

Yeah. So I was spending time sometime in 2022. You saw the first versions of things which were sort of spitting out content. Right? But you started to see in mid twenty twenty two or so this idea that the 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 ability to do math. Now in some sense, that’s learned from the language, and it’s just 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 actioning and the model kind of giving a feedback itself. And you started to see, or 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, change the, you know, weights of the thing. Many teams had ML folks on the team, right, just for their application, just doing stuff with their data. But it was sort of like a separate group than every engineer. And you start to feel, and I start to think in mid or so twenty twenty two, that every engineer would become an AI engineer. AI would be a part of it all, and there wouldn’t be you know, Hugging You go to Hugging Face, it’s for the ML wizards.

It’s like which variant of which model with which, you know, weights. And instead, it would be part of every application engineer’s, like, cool thinking. And so you would get tens of millions of engineers who would become AI engineers versus, like, hundreds of thousands of ML scientists. And that that would forget the need for an an application sort of framework for AI and tooling for that computing environment, which is very different. Like, it’s sort of stochastic. There’s randomness to it. How do you measure excellence of it in a many model world as well?

And there’s an opportunity for Bill to empower every engineer becoming that, which is what you sort of saw happening and and certainly what led to partnering with Harrison LangChain.

Yeah. I think as shifts happen, we want to analogize. And and no analogy’s gonna be perfect. I’ll compare it more to the idea of what the Internet enabled and 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, it’s closer to the Internet in 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 you think back to the story of Microsoft. And ’95, Bill Gates wrote sort of the Pearl Harbor memo of, like, we need an Internet native kind of, like, strategy to it. Right? It was a catalyst for consumption and sort of change within this organization more so than mobile. But 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. And most of the incumbents before mobile were the successes in mobile. 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, or what was really enabled by GPS on mobile. And so you get Snapchat and Instagram on the native consumer time getting unlocked, it was kind of the same in that way.

But what really got unlocked was 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 Yeah. As a distribution strategy. Mobile, again, with consumer time, unlocked 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, you install it, you manage it, to SaaS one point o, which was we manage it for you, bimonthly access to it. That begot Siebel becoming Salesforce. That begot PeopleSoft 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 you then unlocked with that new business model an ability to reach new segments that wasn’t maybe as possible before SMB starts to open up.

You get things like HubSpot. Prosumer starts to open up. 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, a new business model emerging from it versus what we currently see right now, which is kind of a sustaining architecture, which is just that of a copilot, which sits 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, and that we’ll move from a paradigm where we 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 are like monkeys doing data entry usually. Like, what’s most software?

It’s a it’s a database with a form on top of it for users to manage information, put information, get information out.

That 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, etcetera, is doing it. And where right now, like, you go to any SLA for any software, you get uptime, you get support SLAs for questions and things like that. I think there’s a world where we move to 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. You 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 Copart to to Control Center. It’ll be a UX for a worker, which is dominant, to a UX for managers. You’ll go from a seat add on to software and labor, and you’ll go from SLA on, like, reliability to SLA on outcomes on work performance.

That’s what can be offered up by this. It’s do 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 the worker does it, and the product paradigm, the distribution in terms of who you can reach changes because ACVs change. And in that way, I think it will be very different to mobile, which was mostly another UX, but the same architecture, same business models.

Most of what we’ve seen has been CoPilot stuff. And I think CoPilot is an incumbent’s strategy. Incumbents own distribution. They own data. They own the UX, and they own a business model that all aligns to pilot. Co pilot as GitHub Co pilot. Right? Like, line suggestions. Think of it like how most go to go to any Microsoft product right now. Every Microsoft product now has a Co pilot experience. It’s of a sidebar, an autofill, things like that. Right? Where the UX, the the core product is 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 worker, but still where every user has a seed and every user doing most of the work. And 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 c Siebel, Salesforce launched, like, five years after Netscape launched.

Like, it might take a moment for that to happen, but the copilot, this idea of I’m still the pilot, I’m still the user controlling everything, and it’s sort of, like, giving me assistive suggestions like GitHub Copilot fits into the UX of incumbents. It fits into the business model of incumbents, and they already control all that distribution. The opportunity offered up to a startup, being a copilot for something else, like, probably won’t be that amazing. And there might be pockets of it where it can really work, but the opportunity to disrupt is to be orthogonal to the incumbents.

I think there’s so much holistically in a company that gets wrapped up around a business model. Right? And if you have a Co pilot business model, or your product is wrapped up around that way, your distribution model’s wrapped up the way that way, sales education’s wrapped up around it, And that’s why I think business model, which encapsulates product and distribution and end markets, if you can be orthogonal to that, to an incumbent strategy there, it and and, obviously, you have to be correct. It is so being much orthogonal to an This idea that you would have a UX not for a worker.

You’d have a UX for a manager. The idea that you’d sell work and outcomes not software. Right? Like, the idea that you’re Salesforce. Right? Selling cloud subscription managed by us versus Siebel, selling an on premise license. You install, you manage, you get patched for. That’s orthogonal. Right? There’s so much wrapped up in the arc fundamental business is in company architectures and all the systems internally and all their operatings around that that it’s really hard to just change. That’s why it ends up being asymmetric competition. It’s not to say they can’t and they won’t, but it it’s a lot more painful of work to be done of organizational change to enact.

And so I think a start up’s opportunity is to build their strength and 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 a toll you know, enable SaaS one point o, enable a totally different architecture of product model and distribute and business model and distribution. Do you think incumbents see this? I think incumbents can have a lot of cake with a CoPilot idea right now, and that’ll be the focus.

I wasn’t around for it. But when Salesforce launched, I’m you know, I think there’ll be some entrepreneur or a few entrepreneurs, hopefully, in the coming year or so, let’s say, who channel maybe the Marc Benioff 1999, like no more software. If you sort of study that time period, Salesforce Benioff, like, picketed outside of Siebel’s conference. Right? No more software. End of software. Right? It 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 SMBs.

You know? It might start in people who couldn’t hire workers to do some of that and and sort of the upstarts, the challenges. And so in that proverbial, like, 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 attack to steal shit and and expand market, because I think this is a way for for market to to expand relative to every incumbent that’s doing a copilot.

First of all, you don’t need as a startup, too much market or too much market changing hands really fast can be dangerous. As a startup, you could only take on so much. You can only grab so much market share in the grand scheme of things. 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 stickiness, that’s how real power accrues. 60% of the available market share, 60% against, 60% against, 60% and over 60% each time is a big absolute number, and so that’s all growing.

And you look back and suddenly of the market size that now exists for this sort of an offering, you’ve got, like, sixty, seventy, 80% of it, and it’s locked in, and you’re the you’re the main vendor, and you’re gonna get seventy, sixty, 80% of the next years available. And anyone who compete with you can’t get all that moved, and is only gonna be able to try and compete you away for 20% of what’s incrementally available. And you’ve got all of the cash flow from having one net customer funding your innovation, your marketing, and your work.

And so how much is available? Is that enough to sort of satiate yourself? And building strength that way is actually what you really need as 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 is gonna be a great value proposition. I’m sure since you run a very successful fund and media company, you have a CFO. And CFO, maybe if they’re full time, has external parties that do stuff for them.

Right? Yeah. 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 you’d sort of be negligent not to switch. Hey. You have to go do some of this work now, and you’ve got a 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, etcetera. Like, I think it’ll be a very powerful proposition.

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 technology’s pursuit of that. And there may be consequences there in terms of redistribution, taxation, all sorts of other things.

Happy to take your 100 There we go. And find micro pockets for it all. I do think, though, that trust if we go to media specifically different from building software here, I do think trust comes into question a lot as a function of both imagery and language models. If any investor says AI has a big opportunity, and many of them also say incumbents are advantaged, so do you think incumbents have this CoPilot advantage. Right? But 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 or even public company kinda, like, pick in some ways. So to the to the media one, actually, The New York Times is an interesting question. Who’s gonna be the arbiter of trust anymore? You’re still gonna need new information, and you’re still gonna need incredibly trustworthy. And I think

I think as a function of LLMs, trust centralizes. Yep. And and there’s huge economies of scale to subscription businesses and advantages. And so fun idea, but if we’re in media,

Yeah.

They’re popular.

Yeah. Yeah. Yeah. I also think it’s you go spend some time with which I have sort of folks at big companies, including a little media. And, again, to this idea of a new architecture, they constantly go, but, like, where was this pulled from the database? And they’re like, which database was this in? It’s such a new mental model to break from.

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 work, mental models that we have. But it’s, like, such a break that I think is what is also exciting.

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 Midjourney or RunwayML and video and some of these other things. Right? Clearly kind of not wrappers in those ways. A lot of what has happened in SaaS and certainly what we see the most of in the news because incumbents are doing it is the Copilot. And I think Copilot is an incumbent strategy. Is that a wrapper around the models sort of in a way?

Right? I think they’re doing a bunch of other stuff to it, right, for for this new application paradigm, but it’s that. You know, we at Benchmark 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, you know, reliability, you know, UX for the manager, not the worker, etcetera. Right? This sort of fundamental change. And we’re starting to see those ideas really percolate.

A lot of it, though, is things that are kinda 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 an open source model, but the open source models weren’t that good until, you know, Lama two more recently. And so you were fine tuning not good enough. Now you could fine tune better and fine tune as a service is available.

How to wrangle the 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 we are starting to see that, boots on the ground, more anecdotes of it. But I’m, in some sense, not surprised that we maybe haven’t yet. Right? Like, go back to history. As I said earlier, Salesforce 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? It was post IPO, wasn’t it? Was it I think the IPO was around I I forget whether it was pre or post, but it was 2012. And so give or take around that time period. You want a story of, like, Microsoft? Microsoft acquired Nokia in 2013. Right? Like, this is not just sort of fun history, but I’m not surprised if we just look at this specific situation, the factors, that it might take a moment to really embrace what’s fully possible with this new architecture.

We certainly think that. And and to the LangChain point, the the idea that every developer is going to come to building AI native, AI enabled applications. Right? Incumbents are gonna enable it. New companies are gonna fully embrace it. And that that needing new tooling and new frameworks for that environment, like, I think is absolutely happening.

I think in the arc of time, if it is a shift like the Internet was, the applications, which 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 MySQL and a bunch of open stuff. Like, it pulls through the infrastructure. That, I think, will be in the arc of time.

Maybe a bit to my comment early on diet. Like, I think there can be a lot of high fructose corn syrup of adoption. Like, there’s an amazing magical moment in a wow, right, when you go experience ChatGPT for the first time or some of the imagery models for the first time. The the rate of adoption of, like, sign ups to some of these things is is just astounding. Some investors have been trained again with a data first, deal flow, rules checklist mindset. 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. I think when you think about sort of enduring need for some of these and long term solutions, you you can make the argument they look a little more like a high fructose corn syrup diet. TBD, 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 you always wanna get lucky, but you’ll definitely be hoping you get lucky potentially in evolution of them.

Yeah. I would say, to a point earlier, right, like, more than half of what we do is the first partner, you know, probably a third kind of at inception. As one was exploring more of what was possible with things like sort of React and the agent ideas and this idea that every developer would become an AI developer versus just the ML wizardry, you know, Harrison 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. Talk about what was happening. We talk about his framework. We talk about, you know, sequence strengths to be building now, etcetera, and just build that relationship. And I never pressured him to say, you gotta start a company. There are some people who pressured him to say, you gotta start a company, but, like, that’s gotta be a founder’s calling. It’s a real responsibility. And so he then said, hey.

I want I wanna go do this. And I said, great. Let’s partner.

Definitely. We probably could have taken more. Probably could take more now. You know, at LangChain, obviously, like, we have more capital than we need right now, but the bottleneck’s been, like, hiring great people and and the initiatives we wanna work on, and that’s driving investment and pace of investment versus we have the capital, so why not?

I think that copilot is an incumbent’s game. We’re seeing a lot of copilot, 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 customers that you couldn’t otherwise reach, right, or mobile and say, it’s not gonna be a distribution opportunity, but the opportunity to be a real architectural shift and holistic company shift that I think great founders are starting to take hold of.

And so I think that’s the opportunity that’s there that maybe is beneath the surface of just the CoPilot ideas. But

That could happen. Do see what I mean? Yeah. Think that but I also think it could unlock segments, which is different to sort of being the means of distribution. Right? But the change of business model here might unlock segments that were previously not served as well in the same way that, you know, an architecture of SaaS allows you to sell to SMBs and do PLG in a way that’s very different. Right? Sort of SaaS two point o. 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 a catalyst for consumption and enabler of new market segments to reach if you fully kind of embrace it.

Nothing. But like before 10:15 mile, like, weekend hill run or whatever. Yeah. My secret to life is a chocolate croissant most days. Wow. So probably a chocolate croissant on coffee. Why? I’m not being rude. That’s like, just shit. Chocolate croissants are wonderful items and give great joy. And how could you be sad if you had a chocolate croissant each morning?

No. I was very fascinated in high school or college by the question of, like, just how far can you go, really? Yeah. That book born to run the incarnation as the sport called adventure racing, which is multi sport orienteering. And I do, like, sixty hour races. I do, like, ultramarathons. I’d run a 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.

I enjoyed all of that, and there’s just the challenge of that question. I would spend a lot of time on nutrition in those days. So pre race, the sort of paleo diet was big at the time, so I did a lot of a paleo diet. You know, you gotta make sure if you’re doing long triathlons, I did sort of like a half Ironman. Never did an Ironman, but a half Ironman triathlon. The amount of salt you’re doing and other sorts of things. I’d try and find, like I really end up liking Honey Stinger as a brand for, like, gels and stuff.

And so I spent a lot more time on that than then. The best person to ask now would be my wife who’s a marathoner, probably, like, the hundredth fastest marathon in The US, like, qualifies for Olympic trials for women, and she’s, like, got all of the stuff down. These days, I have a kid, and I’m a recreational runner. So I don’t add extra stress for it by having rules. I just go out to enjoy it.

One more step. Keep going. Yeah. That that 60 we did, we probably did, like, 250 miles or so. We go through two nights. And so the first night but you’re in Northern Northern Maine, like, right by the Canadian border. One team actually got arrested because they crossed over at they got lost because you’re in the woods with a map and compass. No GPS. And one team got lost and ended up crossing into Canada and got arrested. We end 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 at McDonald’s for an hour.

I’ve never felt worse waking up from that. And then the next night, there were there were sort of man checkpoints where the staff and you actually physically check-in. And, like, if you’re gonna drop out, there’s probably a call that can take you a few hours later, like, back to the town and other things. But there’s some they, you know, set up fires or warmth and stuff like that. So we slept on the ground. And you do it as a team, I had two teammates racing with me, like, spooning each other, you know, with a emergency heat blanket, like, on the ground for, like, an hour and a half.

And you never wanna get up, but you just get up and you start walking or get on the bike. Yeah.

I 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 of me. He makes me more present. He makes me more patient. And if, you know, in part, he just doesn’t give two craps 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. So that’s probably how it’s it wouldn’t be advice for myself before I had it, but would be the way in which it’s affected me so far.

I’m sure we could list out a bunch. I would say that the more exciting thing is how the the leadership to learn from of how some have changed and reacted post it. And so we can all we can all, you know, name the lists of the 2020 and 2022 time frame and some of the silliness. But I think the more interesting lessons to learn is from how great leaderships reacted. And so for Toby at Shopify to make an acquisition and then divest it within 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 truth 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.

He might hate me for he’s so less well known by intention that mentioning him may piss him off, but I hope not. He used to be at Sequoia, and and Sequoia, you know, has a full website with lots of information, and every investor has, like, a profile with, like, questions. And he never did the questions, and I think he’s just said, like, get in touch. But he is both a great investor and has taught me a lot and been very kind to me, so I have a lot a lot of thanks and gratitude for him.

Michael Abramson, and his ability 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 happens to now have firm. So if it’s your question, but that would be that would be the person. Who’s the best board member that you’ve sat

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 the context of a board too and a relationship. One is founder friendly. I I don’t think you should be founder friendly. Not that you shouldn’t be friendly, obviously, but I think the the higher purpose is like founder respect. And friendly can imply, like, cheerleading, yes, person, etcetera. To honor and respect a great founder means sharing truths.

Maybe not saying the easiest thing to be saying. Maybe saying the uncomfortable thing to say. That is respect. So I kind of like founder respect and founder friendly more. And the other would be, I think first call is a very reactive mindset. So venture always talks about I wanna be the founder’s first call. I think of it as first to call and being proactive. Right? Obviously, not obnoxious. It’s not your company. Right? But being proactive versus just reactive. First call implies lots of reactivity.

And I think Eric is, if he looked up his phone and looked at who he’s called in the last, you know, couple days or whatever, he’d have called a lot of his founders and maybe with ideas, maybe with follow-up on things, you know, like but being active, proactive, and having real respect for their greatness and what’s possible and so deeply committed to that. And and make no mistake, his hands are are not on the steering wheel. You know? He’s, like, in the pit crew, and the founder’s very much driving the the car.

But I think the trust he builds and they manifest in to our point of helping founders make great decisions to sort of dent that curve, I’m very impressed with.

To the point of having deep curiosity. I can’t help myself, but sometimes think about later stage things or, you know, like, flexibility probably comes with the curiosity in many ways. Not entirely. Right? Having one main manifestation of that channeled into early stage partnership. There’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 Zurp, I think he also said, like, the main thing is keep the main thing the main thing, and that’s really hard to do. And the force is excellence and is productive pressure. So that’s probably the the biggest thing.

LangChain. 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 you might look at things like Next. Js and Vercel, 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.

You might analogize and think about things like Docker, which made a lot of development much easier by Dockerizing 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, Docker accounts now, a way of building applications containerized. That will happen for AI apps, and and I think that’s the exciting opportunity to chase.

But before we leave you today,