The Exchanges

Q How did you see the fundraising Christian change and develop over those thousand pitches from the very nervous young chap, I'm sure, in 2008 to the much more honed Christian CEO and founder of trade shift in, in most recent fundraisings?

A Yeah, I think, you know, the first thing when I started out, I was very much in awe of these investors, you know, they were famous. One of the very first guys I ever pitched, and I think, you know, I forgot it. It was together when Morten Lund was, was Danny Reimer from, from Index, right? And I was kind of nervous and trying to sort of, he's a big guy, well-known, and you don't want to insult anyone. And I think Morten pretty much opened the meeting by insulting him straight up and saying, hey, I know you only have half an hour, but you want to spend an hour because this is the best thing you've ever seen. And I think what I learned from Morten and what I learned from, from myself also is, look, you know, you got to believe more even than the VC that you are the best, right? And so, and these guys are so used to being, I mean, honestly, honestly, they're so used to be just sucked up So if you want to stand out, be confident in what you have and, and believe in, uh, believe in that, right? I think as you look at the different cycles and how we developed, I mean, obviously as you move from, from C to D round, it's all about the data, right? I mean, that's going to be the huge differentiator over time. You need to really know your numbers. You need to know your metrics. You need to know your industry. You need to understand how your valuation game works long-term. You need to und…

AI assessment note: “when I started out, I was very much in awe of these investors”

Q Can I ask you the first question, which is like, I think a lot of people misuse the word burnout or actually have it, but don't know they have it. When did you first realize that actually the feelings that you had were not maybe right?

A You know, it probably started during, honestly, during the pandemic, right? We were, you know, I'm a very, um, I'm a very social person. I love to coming into office. I loved having all of the engagement, everyone, seeing the creativity of what we're building, and suddenly I was just sitting, you know, for 14:16 hours in front of a screen every day, no breaks. I remember having to sort of, like, schedule bio breaks just to be able to run to the restroom, and the rest was just one continuous stream, and I remember, this sounds bad, and for everyone who works at TradeShift, don't think about it that way, but, like, I end up hating Looking at that screen. I end up hating, ah, I mean, even seeing at some points the logo, right? And, and it doesn't mean I don't do the work and I didn't, you know, believe in the company and, and didn't want to get home. Like I have so much drive towards that, but there's something really, really wrong when the thing you're supposed to love is actually the thing that you almost like, you can't bear thinking about it, right?

AI assessment note: “it probably started during, honestly, during the pandemic, right?”

Q Did you ever have that, where you actually quite liked almost feeling the pain?

A Um, yeah, that's a really good question, by the way, Harry. I think there was this pride of just being able to, you know, keep going. Um, we, we used to have a Skype group, and Skype was a thing of a few people in the company that was called, Late night motherfucking XYZ. And that was because at two AM we were all sitting, solving some problem, getting something done, getting somewhere, and we were proud that we were in that group, right? And then again, that's maybe not the healthiest sign. And so, so I, I do think there's something about enjoying That you can do what other people can't, maybe? Like, you can, you can tough, you can be a little bit more tough, you can last a bit longer, you can get more stuff done. I can go straight from a customer meeting and then make a keynote in the car, and I came back at four a.m. the night before because I was out with customers, and for most other people, that would just mean that they would be destroyed. But how long can you do it, and, and, and what are the consequences of doing it?

AI assessment note: “I think there was this pride of just being able to, you know, keep going.”

Q Do you ever think that your happiness doesn't matter? I was talking to someone yesterday and it was like, it doesn't matter that I am happy. What matters is the machine of Harry and Harry's brand keeps It's going because the money that the machine makes funds so many other things, funds mothers, brothers, fathers, teams. Who the fuck cares if I'm happy?

A Yeah, no, I think, I mean, yeah, absolutely. I mean, I've been thinking that many times during the spring and this year, honestly, right? And I think, you know, as I also said, right, like in the beginning, when you try to figure out what it means to be a leader, you think, Oh yeah, it's about having people follow me. But then you realize, like, you know what, once those people follow you, then you have a real responsibility. Because, you know, I mean, it's pensions on the line, mortgages, children. Like, at that point, you make some choices where you say, my happiness is not what's most important. I mean, I made some decisions where I could have gone a different path, I could have gone a very different path, and probably You know, had a very different outcome and been happier, but it would not, I mean, it would have been a disaster for the company and for everyone involved. Kind of have to sort of eat that, ah, bit of medicine, but I think the flip side of that is with happiness comes also great work, comes great creativity, and, and so on. So, it really depends. I feel like Most founders are people who can't quit, and that's both a blessing and a curse, but happiness is not a given.

AI assessment note: “at that point, you make some choices where you say, my happiness is not what's most important.”

Q Did that sink into you? I mean, that's quite-

A No. At the time, it didn't. I, and, and that's actually really, really sad, right? Because the risk of dying of a heart attack when you have that little, Hemoglobin is very, very high. And so, so yeah, you absolutely sacrifice your health over, over this process. And it's stupid stuff like thinking you don't have time to go to the doctor. And it's like, oh yeah, I'm always tired. I'm a little tired anyway. It's like, what's a little bit more tired means, just means drink, you know, some more Red Bull or some more espressos and so on. So that actually, in one sense, it was a wake up in the sense that I really, really started caring about my health and feeling healthy and being healthy. Um, but I don't think it's sunk in Why I got to that point. I, I realized I needed to be healthy, but just so I could perform. I didn't realize that I got so sick because I, I was so focused or, if you will, obsessed. Yeah.

AI assessment note: “No. At the time, it didn't.”

Q If you could advise founders, you know, we have, gosh, like, 700,000 people that listen, I think 200,000 founders. If you could advise founders listening on what you know now about fundraising venture rounds, what would you say that you wish they had known, you'd known?

A Yeah, I think the first one is don't over optimize on valuation. Um, it's current market's also pretty easy advice. Um, I, I think the second one is Fundraising is, and nobody will admit, it's a game. Don't reveal all your cards up front. Like, you know, I used to always take out one or two slides of the deck, like I'll make the perfect pitch deck, and then I'll remove the team slide. All VCs will then ask the question, but what about team? And that's the question I want them to ask instead of asking some stupid question about architecture that they don't know about anyways, and they just want to sound smart. Because you've got to remember, VCs will always want to have a question that makes them sound smart. So it's much better, uh, they ask about something you have full control over, and they'll say, oh, team. And then they'll show, like, this Kick ass team that done it like three times before and everybody was, was very senior and so on. Remember, it's a little bit of a game and, and make sure that you control the conversation a bit of, of where, you know, do you want to go? And then, and then lastly, I think, remember you're building relationships for five, six, seven, eight, nine, 10 years. Just min, max negotiating on the very first contact. Like if, if, if you're about to do something together, that, that might be very suboptimal for, for the whole length, right?

AI assessment note: “I think the first one is don't over optimize on valuation.”

Q day with, uh, when I was doing my research on you, I came across a tweet on your profile that was simply too enticing for me not to ask you, and it says, we currently talk about the globalization of jobs. The discussion should be about the globalization of technology, so I was too intrigued as to ask, what do you really mean by this? Yes, let's start with that.

A I mean, there's this big global political discussion going on right now around trade and, you know, how we create jobs. I mean, obviously, in UK, you had the Brexit discussion here in the US. We've just been through what we can call the Trump discussion, but it's essentially a wave all over Europe, right, in the world. And I think while we talk about globalization, we forget that technology is actually the biggest driver in changing the job market. 80% of the jobs that disappeared in US manufacturing did not Go to China. They went to technology. And technology behaves very different from trade. So I think we should really have the discussion around what are we doing in a world that is becoming rapidly more globalized when it comes to technology. And there's a lot of leveling of the playing field right now. For instance, automated manufacturing is expensive. It's heavy. It's hard to do. Very soon, that will be completely commoditized. And again, AI will do the same to manufacturing that it's doing to software. So I think This is sort of the big movement of our time, and I don't think we have enough discussion, and I think a lot of the protectionism and a lot of the sort of reaction we see is just a symptom to try to understand this, and we're not really having the real discussion, and I find it very fascinating.

AI assessment note: “technology is actually the biggest driver in changing the job market”

Q day with, uh, when I was doing my research on you, I came across a tweet on your profile that was simply too enticing for me not to ask you, and it says, we currently talk about the globalization of jobs. The discussion should be about the globalization of technology, so I was too intrigued as to ask, what do you really mean by this? Yes, let's start with that.

A I mean, there's this big global political discussion going on right now around trade and, you know, how we create jobs. I mean, obviously, in UK, you had the Brexit discussion here in the US. We've just been through what we can call the Trump discussion, but it's essentially a wave all over Europe, right, in the world. And I think while we talk about globalization, we forget that technology is actually the biggest driver in changing the job market. 80% of the jobs that disappeared in US manufacturing did not Go to China. They went to technology. And technology behaves very different from trade. So I think we should really have the discussion around what are we doing in a world that is becoming rapidly more globalized when it comes to technology. And there's a lot of leveling of the playing field right now. For instance, automated manufacturing is expensive. It's heavy. It's hard to do. Very soon, that will be completely commoditized. And again, AI will do the same to manufacturing that it's doing to software. So I think This is sort of the big movement of our time, and I don't think we have enough discussion, and I think a lot of the protectionism and a lot of the sort of reaction we see is just a symptom to try to understand this, and we're not really having the real discussion, and I find it very fascinating.

AI assessment note: “80% of the jobs that disappeared in US manufacturing did not Go to China.”

Q I do have to ask. We see co-pilots everywhere. Miles, you mentioned co-pilots earlier. How do we feel about the rise of co-pilots? Are they an incumbent strategy? How useful are they? Christian, I want to start with you. Christian Lang, over to you. How useful are co-pilots and are they an incumbent strategy?

A I mean, who wants a co-pilot? I want to be a pilot. Like, and I want to have a pilot. Like, I don't want to have a co-pilot. I don't want to be inside an application. I don't care how many co-pilots you have. The problem is not to have an AI help you navigate an application that's shit. The better solution is to remove the application that's shit, and just talk straight with AI. And I think the co-pilot metaphor, right? I mean, what happens when we have 10,000 Clippys all just talking to each other? And for you to work, you have to go and work in all of these Clippys, and you're gonna have to tell Clippy A to go talk to Clippy B about that thing you have over in Clippy C. I mean, it's gonna be worse than it is now.

AI assessment note: “The better solution is to remove the application that's shit, and just talk straight”

Q I do have to ask. We see co-pilots everywhere. Miles, you mentioned co-pilots earlier. How do we feel about the rise of co-pilots? Are they an incumbent strategy? How useful are they? Christian, I want to start with you. Christian Lang, over to you. How useful are co-pilots and are they an incumbent strategy?

A I mean, who wants a co-pilot? I want to be a pilot. Like, and I want to have a pilot. Like, I don't want to have a co-pilot. I don't want to be inside an application. I don't care how many co-pilots you have. The problem is not to have an AI help you navigate an application that's shit. The better solution is to remove the application that's shit, and just talk straight with AI. And I think the co-pilot metaphor, right? I mean, what happens when we have 10,000 Clippys all just talking to each other? And for you to work, you have to go and work in all of these Clippys, and you're gonna have to tell Clippy A to go talk to Clippy B about that thing you have over in Clippy C. I mean, it's gonna be worse than it is now.

AI assessment note: “The better solution is to remove the application that's shit, and just talk straight with AI.”

Q Is your health just in the shitter in those moments? I mean, that, that travel is just brutal.

A Oh, absolutely. I mean, I mean, this is probably too much, but like, I mean, I almost died of anemia, actually, because, um, I just didn't have time to go to the doctor. You know, I felt really fatigued. I felt really tired. And, you know, just before, Annual sales kickoff. I, I, I went, I went to the doctor and said, I feel really fancy. He's like, let's, let's take a blood sample. And we did, and I went off to Las Vegas to do the rah, rah, rah, and, you know, in front of the whole company. I mean, I stepped down from stage. There's a text message from a doctor that says, go immediately to the nearest ER and tell them your hemoglobin is So, I remember being, I'm sort of in a blur going to-

AI assessment note: “Oh, absolutely. I mean, I almost died of anemia, actually”

Q Is there anything that's helped you do that?

A Yeah, I did coaching for seven years. I had an amazing coach. Uh, in the very first session I had with her, I said, look, coaching is bullshit. I don't want you to take my anger away. I'm angry about all the bullshit from my childhood, and it's just like, I want to build and show everyone what I can create. And she just looks at me and she says, Christian, what makes you think, ah, that it's not a bigger revenge to be happy and successful? And I was just like, F you. So that was the start, but I think one of the things she taught me is, it's okay. Like, it's okay that you're failing at certain things. I also think it's about creating maybe a family life and a, where you are aligned in what you want. Uh, and you know, you can build together. For instance, this is what I'm doing now. And in that way, it's not a constant talk of force of, of, of time, right? And it's more like you're pushing in the same direction. Now, that's very, very hard to find, of course, but, but that's at least what works for me.

AI assessment note: “Yeah, I did coaching for seven years. I had an amazing coach.”

Q Is that unhealthy? Like, cause I don't mind.

A No, I mean, I used to also don't mind, but I think I also learned that I also don't mind actually being happy. Did a bit of the edge go off? I think you should ask my competitors about that. They'll probably say no. And that's the thing. I think inside your head, you think it's really, really important and it's what drives you. But what I found is like, even when it goes down a little bit and you feel less of the anger or less of the motivation from that, I didn't lose my drive. One thing you might be depriving yourself of is, is figuring out that you have the drive because you have the drive and it's not necessarily with something external. And I mean, that's awesome. That just means you're a creative driven person with, with a high amount of willpower, right?

AI assessment note: “I also learned that I also don't mind actually being happy.”

Q How did you get over the thought that, ah, it's just COVID, and actually I'll get over it when we get back into the real world?

A Yeah, no, I think that's actually, I mean, it sounds bad. I think that's almost what broke me, right? Because, you know, the moment then COVID was over, you're like, okay, finally, we can get back. Finally, you have this hope. I mean, that's, that's very famous saying, like, the most dangerous thing in the world is hope, right? Because then you get back and it's not there. The energy is not there the same way, right? And I think at the same time, um, I mean, obviously COVID was an extremely challenging business environment, as you can guess, also every unicorn, we're, ah, struggling massively, right? We, we moved from a world where there was 40, 60 X revenue multiples to a world where there's seven X, right?

AI assessment note: “I think that's almost what broke me, right? Because... you get back and it's not there.”

Q And people often ask the question, like, how do you know when to give up versus when to persist? And I always say it's when you are no longer excited to try anything new with that venture. There's no new projects you want to do. There's no new hires. There's nothing that you're excited to do.

A No, and I also think, like, it's like, you see the same strategy for the seventh, the 17th time, and people are like, hey, we have this great idea. It's like, yep, been there, and I, I realized, like, in the early days of trade shift, we always said, like, be critical, not cynical, right? Like, critical is to try to improve an idea and to, to pressure test it to make it as good as possible, and cynical just means you've given up before you even try, and I realized, like, I'm the cynic in the room, right? Like, I'm the last one who should be the cynic, and I'm the cynic, and I, At the same time, I was, you know.

AI assessment note: “cynical just means you've given up before you even try, and I realized, like, I'm the cynic”

Q I hope it's okay for me to ask, do you, were you there for your child in the way that you wanted to be, and how do you feel about that?

A Um, first off, I would say COVID was the biggest blessing in that regard because, uh, so I have an eight-year-old son, and, uh, during COVID, uh, when I was working home, I got to spend two really amazing years where You know, we hung out every day. We built Minecraft. We did a lot of stuff, because also remember, I was sort of, Really having a hard time engaging with a lot of the primary stuff. And so, so this stuff became really, really good. You know, time will tell. Um, I think I always tried to be honest with my son about what I do and why I do it. I always tried to be honest that I work a lot and, but I also tried to include him in what is the work. My, my son and my girlfriend's daughter, we were, um, we were on vacation this summer and we did, uh, called it a business summer camp. Uh, and, and they both had, like, they made a startup, like a rocket company and a candy shop, and in a way, you, you have two choices if you want to do this, and you have kids, right? You can try to, Shield them and, and, and keep them away from it, or you can try to include them so they can see what it is. And again, as I said, time will tell, right? Um, but.

AI assessment note: “COVID was the biggest blessing in that regard because, uh, so I have an eight-year-old son”

Q Is there anything that's helped you do that?

A Yeah, I did coaching for seven years. I had an amazing coach. Uh, in the very first session I had with her, I said, look, coaching is bullshit. I don't want you to take my anger away. I'm angry about all the bullshit from my childhood, and it's just like, I want to build and show everyone what I can create. And she just looks at me and she says, Christian, what makes you think, ah, that it's not a bigger revenge to be happy and successful? And I was just like, F you. So that was the start, but I think one of the things she taught me is, it's okay. Like, it's okay that you're failing at certain things. I also think it's about creating maybe a family life and a, where you are aligned in what you want. Uh, and you know, you can build together. For instance, this is what I'm doing now. And in that way, it's not a constant talk of force of, of, of time, right? And it's more like you're pushing in the same direction. Now, that's very, very hard to find, of course, but, but that's at least what works for me.

AI assessment note: “Yeah, I did coaching for seven years. I had an amazing coach.”

Q Sure. So my point being like, how do you feel about your relationship to money today? And did that change?

A So for me, money has never been the goal. Um, it's kind of weird. Like I always just been a very curious person. Like I actually didn't really like, I mean, I always just stumble into things that sort of pique my curiosity, and then I start digging at them, digging more at them, and what I found is that if I follow my curiosity, it tends to follow that, you know, success and, and, and money and so on, but I think also in my later years, right, like, it's, it's easier when you don't have any kids and it's just you, you know, like, I mean, what is risk really then? Like, risk is just all the investors and, you know, especially when they want to, Extract a bit better terms or, you know, bully you in a down market or whatever, right? They will tell you, like, oh, we would lose you. We'd hate to see you lose everything, right? But the reality is, my everything is my mind, right? They can lose some money, but I can, I cannot lose my mind. I can still, you know, tomorrow go out and think about what's next. And so I think for me, money is later in life, now that I have a family and people, like, of course it's important that you can support everyone, but It's never been the goal. It's really nice. Like, I mean, people who say money can't buy happiness haven't tried. You can definitely make things nicer, and you can make life nicer, but I think it gets very hard to sustain that drive if…

AI assessment note: “So for me, money has never been the goal.”

Q Did you do things that you wouldn't have done otherwise?

A I mean, if you think about it, right, and this is, this is, as I said, 14 years ago, we raised our A round at a hundred million dollar valuation. Uh, we did our B round at a 140, C at three 50, right? So these were hefty numbers 14 years ago. We could, because we had a strong vision and a strong product and, and, and strong customers, but it also meant that when real SaaS metrics started emerging and the market started normalizing, and then it was really, really tough, right? Because Uh, we had to catch up to that and we had to do some creative structuring of financing into the interim because you couldn't go out and raise necessarily say market or you would be forced into a down round and so on. So I think I got like a PhD in, in, in finance, uh, as well in, in the last 14 years.

AI assessment note: “we had to do some creative structuring of financing into the interim”

Q Did you manage your investors well? No one teaches, like, founders, like, investor management, do they?

A I, I think for every investor I have to listen to this, they said we probably liked a bit more shareholder updates, and a bit more, like, it's hard when you feel like you're just running from, I mean, You know, for the first seven, eight years, it's just up and hypergrowth, and then you are, like, in turbulent waters, and you're just running from fire to fire to fire. That's hard. Like, sometimes I was writing an update, but by the time I was done writing the update, everything had changed. And you're like, how do you keep catching up? And, and so, but like, for the last parts of this process, we had to have a really tight coordination between the shareholders to pull it off, and, and we did that by having very frequent calls and trying to explain everything, what's It's going on to everyone. I would like to think in a future life I could do better.

AI assessment note: “I would like to think in a future life I could do better.”

Q Do you think, one thing I've been thinking a lot about actually is like, does it actually remove the importance of user interfaces?

A Completely. I mean, user interface, okay, I'm going to say something that's blunt. User interfaces are stupid. It's only because we only had that metaphor, right? We, we create screens with buttons, and I mean, every year, every enterprise vendor is forced to come up with more screens with more buttons. Why? They sell user licenses by the seat. Guess what? Is there incentive to make the application more complex or less, less complex, right? They only go one way. So, why would you need that? If you can just say, hey, I'm gonna take two weeks of vacation, could you please update the, uh, company record? Or, if you could say, I, I would like to generate a vendor database based on this folder, uh, Google Drive folder that's just true at you, With invoices. Natural language, of course, is far more efficient, but we can't just do prompt. We can't just like, I mean, everybody's like, well, you can do anything you want with chatty. Well, I mean, 99% of people use it as Wikipedia, and that's it, right? So we need more. We need the ability to, you know, be able to push buttons. We need, but we need to have a completely different experience. When mobile came, it took five years before we really started having the concepts of responsive mobile web design, user interfaces emerge. And I think we're seeing the same right now. There would be a new generation of user interfaces that haven't ful…

AI assessment note: “Completely. I mean, user interface, okay, I'm going to say something that's blunt.”

Q Can I ask, what were those reality checks? I think everyone talks, you know, was there like a moment when you were like, I have to change this?

A I think one thing was, you know, like, I'm just, As I said, going around during COVID and, and, you know, I mean, realizing, you know, I'm thinking every day more about what food I'm going to cook tonight, what hike I'm going to do. Like, that sounds innocent, but like, at some point my girlfriend, she's like, you know, you know, you like literally only want to talk about things that are not traditional. If you don't want to, you know, if I talk about like, even for a second, you change topic. You don't want to, like, meet anyone. You don't want to go out. You're just sitting at home. You either want to play computer games or cook or, and you used to be this insanely social person. And, you know, realizing that my whole personality was almost, like, flipped around was, was, was a big part of it. And I mean, she kicked my ass also and said, like, look, this is not who I saw. I mean, she's like, I fell in love with. You're like a different person, right?

AI assessment note: “realizing that my whole personality was almost, like, flipped around was, was, was a big part”

Q Do you think that's normal? Like, I'm, I'm the cynic in 20 BC. It's, you know, why? It's getting fucking weathered. I've been doing this for nine years. I've seen this shit before. I've lost money.

A I think it's really, really important that you push yourself to not be the cynic, or figure out how not to be the cynic, because if you don't look at stuff with, with fresh eyes, like, I thought all of the crypto stuff was absolutely BS. I still think, like, most, I, I've done transactions and, Supply chain infrastructure and payment infrastructure my whole life, right? So I had a little bit of knowledge and background to look at it from. I was like, there's no way this makes sense in any world. But then a few people challenged me and I challenged myself to say, no, no, try to look at it as if you wanted to build something in this space. And you know, like I was not a big fan of, of a lot of the community and so on, but I, I tried because I don't want to be that cynical and say, okay, this is just BS, right? Ultimately it was just BS and I'm happy I didn't build something in this space.

AI assessment note: “it's really, really important that you push yourself to not be the cynic”

Q How did you see the fundraising Christian change and develop over those thousand pitches from the very nervous young chap, I'm sure, in 2008 to the much more honed Christian CEO and founder of trade shift in, in most recent fundraisings?

A Yeah, I think, you know, the first thing when I started out, I was very much in awe of these investors, you know, they were famous. One of the very first guys I ever pitched, and I think, you know, I forgot it. It was together when Morten Lund was, was Danny Reimer from, from Index, right? And I was kind of nervous and trying to sort of, he's a big guy, well-known, and you don't want to insult anyone. And I think Morten pretty much opened the meeting by insulting him straight up and saying, hey, I know you only have half an hour, but you want to spend an hour because this is the best thing you've ever seen. And I think what I learned from Morten and what I learned from, from myself also is, look, you know, you got to believe more even than the VC that you are the best, right? And so, and these guys are so used to being, I mean, honestly, honestly, they're so used to be just sucked up So if you want to stand out, be confident in what you have and, and believe in, uh, believe in that, right? I think as you look at the different cycles and how we developed, I mean, obviously as you move from, from C to D round, it's all about the data, right? I mean, that's going to be the huge differentiator over time. You need to really know your numbers. You need to know your metrics. You need to know your industry. You need to understand how your valuation game works long-term. You need to und…

AI assessment note: “as you move from C to D round, it's all about the data”

Q What would you most like to change about the world of AI?

A I mean, actually not a whole lot. Like, I mean, one of the things I was talking to, um, Steve Krasn, who's, um, Krasn, he's, uh, a former head of product at DeepMind, and we were both talking about the same thing, which was, he's like, if you go back five, six years, it was like, AI was made by these, the cathedrals, like Google, and it was like, really serious scientists doing really serious stuff, and now people are hacking and LM models on Discord, and, and so, so we have this underground that's now just, Hacking and building everywhere, and I think that community is really, really fun. I mean, we are part of a number of, like, other startups, and everyone is in Discord, by the way, now. I mean, it's so crazy, like, nobody is on Slack that I know in this environment. It feels very, very different from anything I've ever been part of, so I wouldn't change a whole lot. I mean, maybe slow down the papers a little bit so we can have time to read them, because it's, it's like, like a hundred new papers every day, and, and, yeah.

AI assessment note: “maybe slow down the papers a little bit so we can have time to read them”

Q I want to bring in a new voice here, Christian Lang. You're the former founder of TradeShift, now the president or co-founder of Beyond Work. I have to ask, how do you think about this consumption model pricing versus seat based pricing question in the future?

A But I do think the world is changing. I think we're going to absolutely move to consumption based pricing. It's the only way I think it's going to be very hard to hold the moat on, on recurring revenue as it is today, because customers will want to see more value, and they'll want to see a more soft ramp up to that value. But I also think on the work piece, look at the demographic problem, like most of the people I talked to, even if they wanted to replace the workers they haven't just yet serviced us today, one to one, they can't, because that generation of young people, they don't want to go in and sit in front of a computer and type formulas into work day every day. So, so we got to completely change the work experience. In next five to 10 years, so we're gonna run out of people to do the work.

AI assessment note: “I think we're going to absolutely move to consumption based pricing.”

Q Like, what, why, why is that? I'm a board member.

A Yeah, no, I think maybe, I mean, depends, right? But look, if you think about the type of funds and capital managers and people you deal with at, at a late stage growth startup, I mean, there's probably as much space to have that mental health conversation as there is on Wall Street in general, which is not a lot, right? And I think, um, you know, we all agreed that it was best I stepped aside, and we made space for, for, for, for the next generation, and I think, for me, the, the most sort of prone feeling I had after was just relief. Like, I was so relieved to be able to say, okay, somebody else got this now. Somebody else has the job of, Driving it further and, you know, getting it to the next stage, and that's what, you know, as a hindsight, it's twenty-twenty, right? That's when I really realized, holy shit, I've, I've really, really been in a bad place. Because to feel that immense relief of letting go of something I'd done for 14 years, And then not seeing it while you're in it, right? So that's actually what prompted me to write the post, and I was really in doubt, like, do I want to write this, right?

AI assessment note: “there's probably as much space to have that mental health conversation as there is on Wall Street”

Q And people often ask the question, like, how do you know when to give up versus when to persist? And I always say it's when you are no longer excited to try anything new with that venture. There's no new projects you want to do. There's no new hires. There's nothing that you're excited to do.

A No, and I also think, like, it's like, you see the same strategy for the seventh, the 17th time, and people are like, hey, we have this great idea. It's like, yep, been there, and I, I realized, like, in the early days of trade shift, we always said, like, be critical, not cynical, right? Like, critical is to try to improve an idea and to, to pressure test it to make it as good as possible, and cynical just means you've given up before you even try, and I realized, like, I'm the cynic in the room, right? Like, I'm the last one who should be the cynic, and I'm the cynic, and I, At the same time, I was, you know.

AI assessment note: “I realized, like, I'm the cynic in the room, right?”

Q Are they actually trained on the same data? When you actually speak to those engineers, They're super happy to tell you about their models, super happy to tell you about their models. The minute you go to, like, underlying data, sorry, that's not something we discuss.

A Yeah, no, and I think obviously because people are afraid of the copyright issues, I think the copyright issues are trending in a direction where I don't think it's going to be a major problem. I mean, fair use, I think, is, is, is, is covering this fairly well, but look, it doesn't matter if you have 10% different data if you train on one trillion parameters. It doesn't matter because it's such a big data set that that actually is such a small, Rounding error in, in what you get out on the other side. But what matters is, if you have 15 years of proprietary data on how to manufacture certain enzymes, or biology, or if, you know, because that's the stuff.

AI assessment note: “it doesn't matter if you have 10% different data”

Q So when we see the removal of brand?

A I think actually that one of the biggest impacts of AI and LLM is that most application-based brands are going to be really struggling because the brand is the UX. If you're not actually touching the button, so why are they making copilots? They're making copilots because they need you into it. In fact, everybody's talking about the big problem Google have in search with AI and their revenue stream. Nobody's talking about what it means for enterprise application. I'm so sorry, but Salesforce is just a database. And LLMs are really good at talking with databases and querying data. You don't need 15 layers between you and that database to do it. And so I think that's where the real challenges are gonna come and they're gonna be, I mean, it's gonna be fun to watch.

AI assessment note: “most application-based brands are going to be really struggling because the brand is the UX”