"How Being a Founder Almost Killed Me"; We Have Lied to a Generation of Founders

Thank you so much for having me.

Yeah. Look, I’ve been CEO, cofounder, and and chairman for for Tradeshift for years. It sounds crazy even saying that number. It was inseparable from my life, I think, in every way. And I think this year especially, I have done a lot of reflection over how the last few years has been and and also reflection of not being happy. And I think as founders, we think we just have to keep doing the job no matter what. For me, it was really important to get to the company to a place where was really good shape. but I also made the decision, I think earlier this year that I would find and figure a transition and and, you know, move to what’s next.

It’s probably the hardest decision in my life, and I had no clue how to do it. There was very few people you can talk to about how do you do this? How do you exit this thing you built?

You know, it probably started, honestly, during the pandemic. right? We were you know, I’m a very social person. I love coming into office. I loved having all of the engagement of everyone, seeing the creativity of what we’re building. And suddenly I was just sitting 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 and the rest was just one continuous stream. And I I remember this sounds bad. 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 even seeing at some points the logo. Right? And And it doesn’t mean I don’t do the work. and I didn’t believe in the company and and didn’t 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?

No, I think I just like, you know, not just like, oh, I don’t like this meeting. This content here is not good. But then you start realizing it’s across the board, right? And it’s like a bit like the frog getting boiled slowly. right? You You don’t see it when you’re in it. And it took sort of some pretty big reality checks both on my health and and on my work that made me realize, no, you’re not in in a healthy place. Right?

I think one thing was, you know, like, as I said, going around during COVID and, and, you know, I mean, realizing I’m thinking every day more about what food I’m to cook tonight, what hike I’m to do. Like and I mean, it sounds innocent, but, like, at some point, my girlfriend, she’s like, you like, literally only want talk about things that are not Tradeshift you don’t to, you know, if I talk about, like, even for a second, you change topic. You don’t to like, meet anyone.

You don’t to go out. You’re just sitting at home. I don’t to play computer games or cook. And you used to be this insanely social person. And, you know, realizing that my whole personality was almost, like, flipped around was a big part of it. And And I mean, she kicked my also and said, like, look, this is not who I saw. I mean, she’s like, I fell in love with you. You’re like a different person, right?

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, all the energy and you have this hope. I mean, this this 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 at the same time, I mean, obviously, Covid was an extremely challenging business environment, as you can guess.

Also every unicorn were struggling massively. Right? We We moved from a world where there was 60x x revenue multiples to a world where there’s 7x, x. right? And so you have to restructure financing in that environment. You have to go out and all the shareholders who’ve been loving what you’ve been doing up until that point really do not like to have those conversations. So it’s also you move not just from environment where think you’re to be you’re be creative, you’re going be fun, but also to an environment where every single conversation you have is just hard edged.

It’s tough negotiations, and that’s fine. that’s the job. But it’s also, I think, at some point, you to get the job done. I feel like you owe to employees, you to actually shareholders to everyone that you get the company to the other side. But grit alone don’t make you happy. Just get the job done. Right? It just gets you to the other side. But the cost for me was very, very high of getting to that other side.

Yeah, absolutely. I mean, I think 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. So I think 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. So you kind have to sort of eat that 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 people can’t quit, and that’s both a blessing and a curse. But happiness is not a given.

Yeah. Like, there was a very small circle of of people in Tradeshift that’s been around for 10 years. And I told a few of them, look, I am really, really, struggling, and I’m trying. But it’s also, as the leader, like, you’re a symbol in a way, right? You can’t go in a town hall in the whole company and say, listen, guys, I’m actually getting severely depressed at doing the work or, like, you know, I’m I’m suffering from burnout and I’m not sure I can go the distance.

And Can you not say that? Maybe I could. I don’t know. That’s a great question. I chose not to. I chose to say, no, no, we can get through this. Right? Because also felt like a lot of other people were, of course, struggling. Right? Like, you know, we were going from a world of growth to, you know, margins and profitability. Right?

Like the work environment was also changing a lot for everybody in trade Tradeshift. and we went through layoffs like everybody else, right, Like, you know, to improve profitability and so on. so I think in all of that, if you then stand up as a leader and say, and by the way, I’m also feeling slightly depressed and burned out, I think I might have gotten like nephew from good chunk of the company. Right?

Absolutely. And I think it is some stupid male stuff, Probably just ego. It’s interesting, right? Because my partner now, she’s like, I don’t need you to carry me. I don’t need you to help me. Like, I’m a strong, strong person. And I think that had made me reset a lot of how I approach this and why I’m doing stuff. And I’m allowed to just do it for myself. I’m allowed to do it because it’s fun. I don’t have to carry someone, and I think that’s freeing.

It’s also something I’m really still trying to get used to. But you get kicked from time to time and try to learn from it.

I knew the transaction had to be done. Ultimately, then it was down to figuring out how long and when and where to put the focus.

No. I mean, brutally honest here. Right?

Yeah, I know. I think if you think about the type of funds and capital managers and people you deal with at at a late stage growth startup, mean, I 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. And I think we all agreed that it was best I stepped aside and we made space for the next generation. And I think for me, even when it was just there, like 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 getting it to the next stage. And that’s what hindsight is hindsight is,, right? That’s when I really realized, holy shit, I’ve really, really, been in a bad place. Because to feel that immense relief of letting go of something I’ve done for 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 to write this?

Part of me would have like, there should be this voice telling me that’s bad and you know, you should care more for the people. you should fight some more. But I was just like, I am so done. Like, this was not just a marathon. It was an ultramarathon times 10. And right now I I can’t imagine anything better than I don’t have to do this right now. And that’s just both great and in some side incredibly sad because this is my life. Right?

No. And I also think, like, it’s like you see the same strategy for the the 17th time, and people are hey, we have this great idea. It’s like, been there. And I I realized, like, in the early days of Tradeshift, we always said, like, be critical, not cynical. right? Like, critical is to try to prove an idea and 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.

I think it’s really, really, important that you push yourself to not be the or figure out how not to be the cynic. Because if you don’t look at stuff with fresh eyes, like I thought all of the crypto stuff was absolutely BS. Still think like most, 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. It’s like, there’s no way this makes sense in any world. But then a few people challenged me and I I challenged myself to say, no, no, Try to look at it as if you wanted to build something in this space.

I I was not a big fan of of a lot of the community and so on, but I tried because I don’t to be that cynic and say, okay, this is just BS, right? Ultimately, it was just BS and I’m happy I didn’t build something in

Some or put in another way, I think for me personally, did I leave something behind? Probably. But I also, I think, you know, learned so many lessons. Like, we were kids. Like, me and me I was joking the other day. I was I was talking to business, like, people are like, oh, SaaS metrics should be this, and this should be your margin and rule of 40 and all of this. Like, are you aware that none of this existed years ago? We were making it up as we went along.

It’s like, what should be great metrics for a SaaS companies Like, nobody knows. Right? So I think, you know, it’s it’s really important to understand that all of those lessons that today, it’s just a machine. It got be like this. Here’s the metrics. Here’s the thing you to hit. All of that. We have to experiment, experiment, and build and learn. I mean, one of the things that excites me today is to say, wow, I can take all that knowledge, I can take all those ideas and I can approach completely from fresh.

Yeah. No, absolutely. I mean, ultimately, there’s also a chance to make a lot of new mistakes if you haven’t tried to make sure. So But we’ve eliminated a world. Could make them faster and I can learn faster. Right. And I think back to the to the burnout side of things, like I was also advising on a few things, and I was really getting immersed in everything that was happening in in generative AI. I I studied as a sociologist with language as as a primary, like, public system and language.

So everything was happening in generative AI was piquing my brain a lot. And when you’re figuring out every time, like, that once a week you’re listening into that team meeting or hearing or seeing what they’re building, that’s the most exciting moment in in what you’re doing. And you know, what you’re doing every day is the thing you just gotta fight to do. then I think your energy is also flowing differently. And I think that’s also why the idea of of being able to sort of have a bit of a blank slate and think differently and build differently and and use all of my experience, that’s really exciting.

I mean, I think it’s true, unfortunately. So I honestly think a big problem over the last six to seven years is we started telling everyone they should become a founder. At the same time, we didn’t tell them what that means. And I think the people I know who persisted, right? Like the people who, for instance, for like the Danish mafia, the early, you know, Zendesk, Unity, all these guys, none of us are normal people. None of us with extremely unhealthy life work balances. Right? And and so I don’t think.

I don’t know. I’ll try to see if it can be different this time. Like, I’ll try, but I don’t know. And and I have a feeling once I’ve really pulled into the idea, it’ll be hard. right?

Yeah. No, I think there’s a lot of things. I mean, the the the first thing is for 99% of startups, no offense, but VCs is going own most of your company by the the time you have worked for six or seven years, and your salary will probably be less than if you had worked anywhere else combined. And that’s if you’re lucky. Right? 99% of you just.

Exactly right. And And the second thing is also just like that, as you just said, it’s just about surviving, etc.. Like, are you willing to really think through what that means on the cost of your family life, your connections, your friends? Like, I I’m lucky. I have like two or three people that still talk to me after years, but that’s about it. Like, everybody else is like, we used to know you, but we don’t. Right.

People outside the company at the time. Right. And Just because you lost friendships? Yeah. And and and the only friendships I sort of retained over that long time in in the end happened to be people I was working with.

Yeah, I think absolutely, actually. What would you

I I mean, I don’t know. right? I mean, it’s so weird, right? Because sort of a side story. I used to play a lot of poker. And, I mean, again, back to that Asian theme or your things that pick out rain. But then my friends is like, why don’t you play poker anymore? It’s like, well, once you’re done a million funding round and you’ve just stared each other down at that table. And I’m I’m not saying founders sometime bluff, but sometimes we do and and sometimes we take it home.

It’s really hard to get excited that sitting at the table and, know, playing about a $100, like even if it’s more. And And so I think our lives become so different. What do you talk about? Like, well, I’ve been traveling around the world. Honestly, like there were many years I did between 150 and and 200,000 miles a year. I was looking at my average. I think I spent around four years in hotels over years. You lose, in a way, connection with reality. I mean, what are you to talk about? it’s like, yeah, this this is what happened this week. and we went to work.

So I think you got find ways to find those common threads and remain. Is your health just in the shitter in those moments? I mean, that that travel is brutal. Oh, absolutely. I mean, this is probably too much, but like, I mean, I almost died of anemia. I just didn’t have time to go to the doctor. You know, I felt really fatigued. I felt really tired. Just before annual sales kick off, I went to the doctor and said, I feel really fatigued. 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. And I stepped down from stage. There’s a text message from my doctor that says, go immediately to the nearest ER and tell them your hemoglobin is 5.4. So I remember being sort of in a blur going So you went back on stage, finished the talk. I delivered the talk. arrived arrive in the ER tell them, hey, my doctor told me my hemoglobin is 5.4.

And she’s like, no, it’s not because you’ll be you’ll be laying in a coma on the floor. And then I said, no. And I showed a text message. The next thing I knew, I had like a bag of blood in my arm and, you know.

At the time, it didn’t. And that’s actually really, really, sad. right? Because the risk of dying of a heart attack when you have that low hemoglobin is very, very, high. 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. It’s like, 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 some more Red Bull, some more espressos and so on. so in 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.

But I don’t think it 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 obsessed. Yeah.

Yeah. no, absolutely. I started exercising four five times a week. took my health very seriously, you know, monitored, I would say, my health condition in general and, you know, probably one of the best things that came out of the last years.

Yeah.

Yeah. That’s a really good question, by the way, Harry. I think there was this pride of just being able to keep going. We used to have a a Skype group, and Skype was a thing of a few people in the company that called late night motherfucking XYZ. z. That was because at 2AM, were all sitting, solving some problem, getting something done, getting somewhere, and we were proud that we were in that group. Right. And in 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 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 4AM 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 what are the consequences of doing it?

You know, time will tell. I think I always tried to be honest with my son about what I do and why I do it. I always try to be honest that I work a lot, but I also try to include him in what is the work. So in a way, you you have two choices if you to do this and you have kids, Right? You can try to shield them 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? Do you regret missing things? Yeah. absolutely. There’s lots and lots of things I regret missing. And, I mean, we all have the right parents, school meetings, etcetera. I mean, one of my friends said, though, being a parent is to permanently feeling feel guilty. Like, that’s just how it is. And I mean, to your point about getting up early in the morning, I mean, if you have a problem with that, just get kids because that solves the problem.

Again, I mean, that’s another, like, thing. It ends up costing family time, and it end up costing, you know, with your family.

Yeah. Yeah. Yeah. I think it’s really, really, important to learn to forgive yourself. It taken me. I’m I’m still struggling with it, but it, Taken me a very, very, long time to do that.

Yeah, I I did coaching for seven years. I had an amazing coach. In the very first session I had with her, I said, 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 to build and show everyone what I can create. And she just looks at me and she says, Christian, what makes you think that it’s not a bigger revenge to be happy and successful? And I said, 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. So I think forgiving yourself and taking some of the hats off, honestly. I also think it’s about creating maybe a family life where you are aligned in what you want. 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 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 that’s at least what works for me.

Yeah. No, of course. And I think, I mean, I I think you’ll have a hard time finding a founder that don’t have something that they’re motivating them. Right? Because as said earlier, like, founders are extreme people. What is it for you? Is it

It was that. And I think over the last seven years, it moved from being that to being.

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, less of the motivation from that, I didn’t lose my drive.

So I think one thing you might be depriving yourself of 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 are a creative driven person with with a high amount of willpower. right? You don’t need to let somebody else who was, you know, a dick in your childhood define you. right? Like, that’s Yeah.

Yeah.

So for me, money has never been the goal. I always just been a very curious person. I always just stumble into things that sort piqued 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 success 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, What is risk really then? like all the investors and, you know, especially when they to extract a bit better terms or, you know, bully you in a down market or whatever.

Right? They will tell you like, we hate to see you lose everything. Right? But the reality is my everything is my mind. They can lose some money, but I cannot lose my mind. I can still tomorrow go out and think about what’s next. And so I think for me 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. People say money can’t buy happiness haven’t tried. You can definitely make things nicer and you can make life nicer, but it gets very hard to sustain that drive if if it’s the only thing.

There got be something you you you want scratch at a peak at or that that particulars your mind enough that you have keep going.

think one of the things that we were lucky early on is that we have a lot of investors that were actually in a way, they were thinking evergreen. They did not have to have necessarily an in three, four, five years, especially because we as when we talked nine years ago, massively underestimated how hard it would be, how long it would take. But I think, I mean, what are some of the things you see? right? I think one

Yeah, of course. But I also think VCs get pissed off when founders use exactly the same strategies as they do. right? And I’ll I’ll take an example right In the latest financing round for for Tradeshift and for all the Tradeshifters out there, remember to remind your investors of this. I refused to sign the papers until the employee stock option pool got moved from common to pref pref two because I did not want all of our employees to be underwater in any potential transaction in the future.

And that did not include stock. This is the thing where people understand waterfalls, understand the games, they understand the leak prefs. they understand how everything flows. Probably not made me the most friends in the in the world at that time. And And I did wait quite late because I knew if I was bringing it up, you know, nine months before, would be hard. But but, you know, when the transaction about to happen And It’s

And Exactly right. And And And this is the other thing, right? Like, runway works both ways. Runway is is an excellent tool to make sure you also are are able to have some leverage in that negotiation because the reality is if if your company is doing well and if you’re great, then if the runway is is shorter, then then everybody needs to come to a conclusion faster. And And that can work both for the founder and for the VC. So I think there’s a lot of stuff where VCs are not your friends, but the best VCs can help you get a great and much better outcome.

And I think one of my regrets, I mean, I think early on, we were too focused on valuation and we probably made some other choices then and spent a lot of time. What would you have done differently? Probably taking some low valuations and not having to fight as hard to catch up to those numbers, to be honest. But

Yeah, I think it’s a very classic trap. Right.

I mean, if you think about it, right, I mean, and this is this is 14 years ago, we raised our a round at at $100 million valuation. We did our B round 140, C at $3.50. Right. So these were hefty numbers 14 years ago. And 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 we had to catch up to that and and we had to do some creative structuring of financing into the interim because you couldn’t go out and raise necessarily the same 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 as well in in the last years.

No, I I think you’re both right. I think he’s right in the sense that you do need. And And in fact, our argument for raising at those valuation were nobody has done this before. Nobody has built a global network for trade just like you build a Facebook. It didn’t exist. And I mean, to be honest, we no freaking clue how to do it. We We have a lot of ideas and we we need to iterate. So my argument was always, we if we get more capital, we have more shots and we can try more times. right?

And also, I of always dislike the whole, you should pick us as a VC. We know it’s a 40% discount to the other guys, but we are smart, like the smart VC story because the reality is, like, if if I need to give a 40% discount because the VC is so smart that they will make up fun value, like, then I probably shouldn’t be the founder. The VC should probably be the founder.

I agree it is. You just to be sure that when you get that name, you also get that attention. Because you’re right. If that brand is behind you, but then also give you that attention to push, then absolutely right. You to be a bit careful with the big names. I mean, they’re really, really, great. and I know a lot of people there. I think they’re amazing. But what you’re going to ensure is you have the attention for the right people. and then what you said will happen.

It’s hard when you feel like you’re just running from, you know, for the first seven, eight years, it’s just up and hyper growth. 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 and by the time I was done writing the update, everything had changed. And you’re like, how do you keep catching up? 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 going on to everyone.

I think I would like to think in the future life I could do better.

Yeah. I think the first one is don’t overoptimize on on valuation. It’s current market’s also pretty easy. I I think the second one is fundraising is and and nobody will admit it. it’s a game. Don’t reveal all your cards up front. I used to always take out one or two slides the deck. I’ll make the perfect pitch deck and then remove the team slide. Because all VCs will then ask the question, but what about team? 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 to sound smart.

Because you to remember, VCs will always to have a question that makes them sound smart. So it’s much better they ask about something you have full control over and then they’ll say, oh, team. And then I’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 make sure that you control the conversation a bit of where, you know, do you to go? And then and then lastly, I think, remember you’re building relationships for five, six, seven, eight, nine, ten years in some cases.

Right. And just min max negotiating on the very first contact. Like if you’re about to do something together, that might be very suboptimal for the whole length. right?

I have investors where I have this relationship with. Right? Like, I mean, a bunch of our investors also wrote me after my post. I mean, some were were happy with the results of the round, which just did. Some were unhappy, but they still wrote me. And And so that meant a lot. But it is clear, right? Like, of course, investors are in it for the money. So to some degree, most degrees, I think founders are as well. But I do think it’s better when there is an understanding.

And I mean, there’s the old saying, like, you know if an investor is good if they show up when shit is hot. Right? Like, everybody is just cheering when it’s like, up, up, up, It’s like, yeah, go faster. But the investors that I have a relationship with today are the investors that were there when when stuff was really, really, hot or when something blew up in a way we didn’t expect or whatever, and they were still there. And so I think, you know, as an investor, probably have some control in the that you show up for for for your founders when everybody else is about to bail on them, for instance.

Right.

No. I mean,

Yeah, Yeah, No. And I I think actually this is part of that used to be part of the leadership principles in Tradeshift, which one of the very first things I taught all our leaders is show vulnerability. And the reason I say that is, you know, in American business culture, you just got be perfect. Like, it’s like, hey, what do you think about this? You have an answer, right? Actually, that’s why ChatGPT is of screwed because it just want give a perfect answer to everything, and it can’t say, hey, could you clarify?

I don’t know or whatever. But I told my leaders that, no, know, people will actually trust you more if you show vulnerability. If you say, hey, this is an area I’m bad at as a leader, this is an area I’m good at. Because that helped build a relationship with people. And I think the same is true as an investor. I think it’s absolutely the right strategy to show vulnerability and say, look, I’ve struggled with these things and so on because it makes you a human.

No, that’s spot on. Like, you know, I I think I failed at at the first leadership principle I I taught most of our leaders. and that’s right. Maybe they’ve gone differently if I had. But I think still, like, I think to try to be real people is very, very, important. And I think vulnerability is actually one of the biggest trust building things you can do. The hard part is I’ve also plenty of times shown vulnerability and gotten screwed over hard. Right?

Just because people take advantage. They see an opportunity. They see money. And and. then it’s really hard the morning after to wake up and say, I don’t want to become a fucking cynic. I’d rather have one more time where you say, okay, I was vulnerable and I got effed, but it was more important that I don’t lose who I am now. people around me probably say, yeah, that’s true, Christian, but you could be a bit more. you could still be a bit more skeptical and a little bit more critical of people.

And yeah.

It is. It is the hardest thing in the world. But if you let yourself become jaded, then you let those people define who you are. Look, I have people out there right now that I really like. They just to exploit the situation and they want hurt me. But what I want focus on is like, I don’t give them any energy. I don’t wanted think about I to think about what I’m building now. I will think about where I’m going in the future. I to think about being happy because back to the point about happiness is the best for mention in the world.

Yeah, it is really, really, effing hard.

Yeah, no, I think, I mean, talk about mental health and startups is wow, That’s that’s a big one. It’s hard, right? Because I believe myself. have the hustle, call I don’t stop. I can just keep going all of those things. Right? So, you know, when I was younger, I thought, like, how do we deal with mental health and startup? We just make sure we hire people only like that. Right? Like, I mean, the the first job like, we we don’t need an HR department because everybody here is just here to work and, you know, fuck it.

We’ll just go full speed. But I think if I can struggle, then anyone can. And if if I can out, then anyone can. And I think startups is 99% people. That is the primary asset. If the wrong person goes down at the wrong time, that can be a very, very big destruction of value. Right? So I think we got find better ways of thinking about it. it. should definitely not be that we now have to all do our journaling and a lot of other woke things that I think probably just contribute more to stress than than that actually helps solve things.

So

I think a lot of the things that were the sources behind wokeness probably have grounding. It’s extremely hard to discuss that within some very extreme environments like startups, because they are extreme machines. They are extreme environments. On the other hand, there’s also been a lot of founders out there that are exploiting that and said, look, it is an extreme environment, so I can do whatever I want. I can be, you know, a psychological terror or whatever. Right? So you you to create an inclusive environment without going abroad, And then you’re just going focus everyone on one thing and one thing only, and that’s building.

I like what David Heinemeier says, like he banned politics in signals, And And I think that’s absolutely right. We shouldn’t sit around the table discussing all this stuff. We should just build something and make it work. And if we’re allowing everyone to be the best at building, then then we’re doing it right.

One of the things we put into what we’re building right now is that that we are a team, not a family. Because let’s be real, like, some of the hardest things I’ve had to do, I I fired a person that I’ve known since high school. I worked with for ten years who moved to California as part of the journey. At that moment, you really do not to be friends with the person, the people you work with. On the other hand, I think it’s very, very, hard to do something as intense and wild and crazy as a startup without becoming friends with these people because you have all these war stories, you have everything you do together.

So one of my good friends and early advisors, he always said, look, absolutely go work with your friends or become friends with who you work with. Just know you might have nine really good years and then the breakup is probably horrible. But why not have five really intense good years with someone when most friendships, to be honest, is we meet in the pub and we talk bullshit about the game. It’s a trade off and I don’t have the answer.

First off, never ever compromise on quality when you hire. You you will be so tempted when you’re in the hypergrowth stage. Everybody will be screaming at you that they need people on this function or this function or this function. And I think Do you think you can have like a plus players in every role? Essentially, it’s just a question of pain. how much pain are you willing to endure to get the right people on the team? Because when everything is scaling like crazy, if you don’t fill that role, it means everybody else is in more pain.

But on the other hand, if you start filling those roles with people who are not the same level of quality, then then you have a challenge. right?

Yeah. But I’ll give you an example. It’s a very real example is, like, at one point, we fired 50% of the VPs in Tradeshift, and there was no drop of productivity. And I I really thought to myself, what the fuck have we been doing? Who the fuck are all these people? Right? And And I mean, that’s real. Like, so operational lessons is that I think the other one is just I mean, this is said so many times, whatever you charge, double your price. We found out in Tradeshift very early on that there was an inverse relationship between price and speed of sales cycle.

The more we charge, the faster we closed. People are afraid of that. People are afraid of saying really large numbers, especially if you come from outside this world. I think another operational lesson that is really, really, important is just you just to iterate faster and you you to kill stuff faster. You’re to kill. Everybody thinks that you can kill stuff fast, but it’s not fast enough. The very best operators, like you mentioned Parker Conrad and people like that, they are so insane at the iteration speed, and that’s why they win.

And I think there’s an ability to understand that. I think in Europe, we don’t really still understand. I was years in Silicon Valley. I don’t think we still understand how much better that most really good San Francisco startups or Silicon Valley startups are compared to the Europeans.

We just honestly like vacation a little bit too much. We like coming home at five with the kids. Like, we starting to have other things that are other benefits, right? Because the very best people in the world in, say, AI or engineering or whatever, they want life quality, right? So Europe can offer a lot on that. But the extremity of execution is something I only ever seen in Silicon Valley. Actually, one other place is China.

I remember, you know, when I first came to Silicon Valley, was Reid Hoffman who actually told me, he said, like, within two square miles of where you stand, there’s 5,000 startups. Within three months, 95% of them are to be dead. And everybody there are to be into new startups, recycling all the knowledge, cetera, right? So you have just to start with, the whole machine recycles knowledge much faster. But the second thing I think within the startups is that shit just get done. Nobody stops until they’re like, I mean, the idea that you work or don’t work on weekends, it’s it’s just not a thing.

And, you you know, if you’re doing a startup and it’s early stage, you just work. You just build, you just do. And I mean, I know it’s ironically to praise that right here as we started the conversation on burnout. That’s probably the paradox. There is no good ways to combine all of these things.

Absolutely right.

Yeah, Yeah, Yeah, But I also think just look broader, right? Most modern work sucks, right? Why do people go to startups? Because it’s exciting, because it’s great, because it’s fun, because you’re doing something with your mind. If you go to most corporate work, 90% of it is like, copy something from this page of this spreadsheet into this field, type this form, click this button, you have no idea what it does, then update this and then keep going. It’s so far removed from who we are as humans. mean, we are animals.

We get a kick out of defending the village, you know, hunting for stuff, raising children, like so it’s very hard to get excited about clicking update lead source four. per CD4. four. Exactly right. And I think so with this new thing, like with with Beyond Work, one of the things that I’ve really been thinking hard about is, can we try to redefine the modern work experience? Can we make it so it’s not the applications that define how you work? Why should it be Salesforce or Workday or SAP, all these systems that make you into a robot?

Why shouldn’t it be you who can just work the way that your brain works? and all these systems should be in the background? So what is Beyond Work? Sorry. Yeah. So Beyond Work is.

Beyond Work is essentially the idea that we should be able to automate any work we want as regular people, and we should be able to take any task and combine it and collaborate with other people around it without having to log into applications. Imagine you have a problem say, hey, I to create a vendor database based off all these invoices. Then the user interface just appears and show you that, and it goes away. So

Exactly right. But it’s centered on humans in the center. Salesforce don’t have a human in the center. Salesforce makes you into a robot that has to click buttons in a certain order. And why on earth should you learn that? Why should you spend 10% of your brain storing information that’s completely useless for anything you do? What you really to be doing is to look at that data and, you pull out conclusions or figure out like, who’s our top 10% salespeople. And we have some amazing powerful tools right now, like, of course, the new large language models, but they don’t really solve the problem with work.

They just give us some power. give us some some stuff we can do in an engine. But what I’ve really been thinking about is how can we put all of this together in a new way? How can we generate a completely new work experience? And the funny thing is, took it out to to a few of my friends who who are like C-level executives in some of the largest companies in the world. And they were almost like, holy shit, how fast can we get this? I think we’ve forgotten.

Just some simple numbers, right? IT corporate budgets, they went from 300 billion to $780 billion in enterprise software over the last years. At the same time, we doubled the amount of people in shared services, 8 to 16 million. and we doubled the amount of people in corporate IT, 4 to Why? We’re buying all of this amazing software that should make everything better and more efficient and more productive, but instead we just become less efficient and we hate our life more.

Absolutely. right. And I think that’s actually where I mean, to me, building a startup today that is AI first is as pivotal or revolutionary as it were years ago to build the first cloud companies. And I’m not talking about ChatGPT and all that. I mean, that’s amazing. And they’re probably gonna invent either superhuman intelligence and we’re all going die according to Elon Musk or it’s to be totally fine. and they’re to be almost as good as self-driving cars, but they’re to fail some of the time.

Right? But what I’m talking about is what are the companies built on this architecture going look like? And years ago, there came something completely new, cloud computing. And suddenly we could make software in a whole different way from on prem and change the world. It changed the enterprise world. And And I think today there’s a new generation of startups that’s to come over the next five, years, and they’re to be built on an AI first architecture. what I personally find exciting is nobody have an idea what it looked like yet.

Well, I think you right when you talk about consumer. And I think, by the way, everybody will be making make a big mistake if they count Apple out of the AI race. They’re going come with 100 miles an hour. I mean, they come in will it will be really, really, good. But if you think about those winners, what they really provided was platforms. We went from having SaaS 1 thousand to 35,000 SaaS companies in ten years. And if you look at the explosion of unicorns, for instance, a very good chunk of them were SaaS companies. right?

Because enterprise is a multipolar world. It’s not winner takes all. I mean, Peter Thiel’s power laws works really well in consumer. But in enterprise, there’s so many modes. I mean, compliance, regulatory, incompetence. There’s just layers of layers of layers of stuff that makes decisions happen differently. And I think the other thing is, if you look at the next generation of stuff about these modes, if you ask me last year, I’ll say somebody like OpenAI is be like the AWS of AI. But nine months later, I was running on my laptop a model that was as powerful as ChatGPT three and a half that was released as open source by Facebook.

So I have never in my life in computing seen something that moves this fast. And you know what’s really, really, exciting? I have no clue how this is to turn out. I don’t know if the incumbent’s going win or somebody else. I don’t care. I just to build something that’s valuable for for people. But I think it’s really exciting that we don’t yet know how it’s to play out.

a lot about actually is like, does it actually remove the importance of user interfaces? Completely. User interfaces are stupid. It’s only because we only had that metaphor, right? We create screens with buttons. 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. Why would you need that if you can just say, hey, I’m gonna take two weeks of vacation.

Could you please update the company record? Or if you could say, I I would like to generate a vendor database based on this folder Google Drive folder I just showed at you with invoices. So natural language, of course, is far more efficient, but we can’t just do prompt. We can’t just like, I mean, everybody said, well, you can do anything you want with chativity. Well, I mean, 99% of people use it as Wikipedia and that’s it. yet. So we need more. We need the ability to be able to push buttons.

We need but we 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 fully been invented yet. But we will look at all of the screens of applications we use every day as dinosaurs in less than three years. We’re like, holy shit, why were we sitting with thousands of buttons and thousands of screens?

Completely. The point is think think about like your your HR system. That’s the head of HR that buys that It’s not you as a worker who sits every day. Same for your system. Same for any system. Whoever made a set of tools, platform for you as a worker. It’s like, I mean, if you were, you know, a forester you’re cutting down trees, would have a chainsaw as your daily tool. Right? But all these systems have been made by somebody else who’s judging by the license, by the user, bought by people who don’t use it.

And then we wonder why the people sit in the middle, they’re miserable. And I think, by the way, like, demographics,

I mean, product led growth is is definitely one way, and I think that’s much healthier than the sort of SaaS revenues of classic enterprise software. Sorry to to the people I sold for the last fourteen years. But I do think the world is changing. I think we’re to absolutely move to consumption based pricing. It’s the only way I think it’s to be very hard to hold the moat on on recurring revenue as it is today because customers will to see more value, and they’ll to see a more soft ramp up to that value.

But I also think on the work piece, look at demographic problem. Like most of the people I talk to, even if they wanted to replace the workers they haven’t their yet service centers today one to one, they can’t because that generation of young people, they don’t to go in and sit in front of a computer and type formulas into Workday every day. So so we to completely change the work experience in next five to ten years, we’re to run out of people to do the work.

Most likely. Two things. I think we are right now both 99% of the money going in is going be lit on fire, and two, we are underestimating the impact of AI. And I think both are true at the same time. But I think we got get at least one or two cycles in to start really seeing what’s happening.

Most likely. We need to do the experiments. But I think the other thing is like, in Beyond Work, we banned talking or using AI as as something we talk about. Like AI is essentially as interesting as saying database or we have a HTML HTML rendering layer or whatever. It’s a set of technologies. And I think what is really, really, important, and I think most people right now that are rushing into, as you said, AI is missing is I think it’s about the user experience. I think it’s about trust.

And trust, by the way, is a user experience. It’s a design exercise. You know, everybody’s like, got have AI stop hallucinating. Well, hallucinations, the more powerful the model, the more powerful the hallucinations. Maybe it’s more about showing why and when.

For us to really truly trust AI in the work environment, we need to have cues and we need to feel we can trust them as coworkers. And that is absolutely a user experience that needs to be designed. Like if you drive a Tesla that’s self driving, it renders everything that’s on the road, right? You don’t have to. I mean, it’s driving. It don’t need to show you. So why is it showing you? Trust. What would it mean? Right now, if you ask chatgpt a question, say, hey, you know, who won second world War?

They’ll give you a a prompt. But what if it said, could you please clarify? Do you mean in this context or from literature or whatever? Right. In fact, some of the things we’ve been playing around with is we we call it if in doubt, ask. We sometimes ask when we already know the answer.

Definitely apply that to marriage.

think humans are incredibly important in the AI loop. Everybody who’s pushing for AGI level AI right now, they’re to be sorely disappointed. I think it’s an asymptotic curve, and I think we’re to end up with way more style cars, meaning you almost have a lawyer, but not quite. And the 5% you don’t quite have, it’s going to be really, really, bad. So I’m not sure there’s a big market for almost lawyers or almost designers almost whatever. I think what’s very interesting is all the trivial stuff we do every day.

All the trivial stuff, like, as you said, even in VC, right, you have to, you know, get these documents over here then you have to correlate and you to run an IR. If we can automate all the trivial stuff that still requires knowledge, that’s actually where the sweet spot of capabilities and models are. and we don’t need AGI to get there. And then the second piece, back to the human piece, which is, I think people ignoring the obvious. Just have humans in the loop to validate it.

Just have humans in the loop to look at. You know, you don’t have to go and find all the information. You don’t have to go search and obscure and click on really bad buttons and some UI you didn’t even understand to to get your job done. The AI can do all of that for you, pull all information, correlate and then you can validate. You can use your brain for what you’re good at. So I think it’s more about when I say changing the work experience, it’s actually about putting the human brain in the place in the loop where it’s the very best and stop trying to make humans into robots.

I think that’s again about back to the trust question. I I saw a pilot recently where we went from, in sixty days, trialing to the enterprise going, we want this deployed to 3,000 people. And it’s because the guardrails around the trust side and the human validation loops are so strong that essentially they say there’s no downside because we have humans validating at everything. Back to the impact on society and and the timeline to it, I think, as I said, it’s it’s almost like we always you know, underestimate the future in the long run and overestimate in the short run.

Like if I see another agent demo on Twitter, I’m just to like, I mean, I I cannot see any more of the hype demos of AI and anyone who’s building real stuff have to do enterprise grade stuff, cetera. we know how many problems there are that needs to be solved. But I think still, when I’m seeing stuff, like I I made a game with my son in a weekend in a programming language I never programmed in. That’s real. Like that’s real world stuff. That is not overestimating anything in the future that happened.

I would not have been able to do that last same time. So in less than twelve months. And so so I think what we also see is the cost of innovation will drop rapidly. Will it go to zero? Probably not. But it’d be much more about execution and ideas and necessarily having the best coders. And I mean, a good friend who was a programmer his whole life, he said to me, look, there’s to be a whole different generation of coders. I’m I’m a I’m a very shitty programmer because I don’t have patience.

Right? So I thought when I learned programming, it’s like, this gonna be fun. I’m some great things my mind and, you know, whatever. And then you learn programming is 90% debugging, and I hate debugging with such a passion. But now I just throw my code at chat and say, hey, where’s the problem? Right? So I do think it will impact society massively, but in ways we can’t really predict yet, even in the short term.

pilots are the last breath from the existing enterprise applications to remain relevant. But they’re startups. Yeah. That’s even worse. Like, I mean, who wants a copilot? I I want be a pilot. Like, I don’t want have a copilot. I don’t want be inside an application. I don’t care how many copilots 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. The copilot metaphor, right?

I mean, what happens when we have 10,000 clippies all just talking to each other? And for you to work, you have to go and work in all of these clippies and you’re gonna have to tell Clippy A to go talk to Clippie B about that thing you have over in Clippie C. I mean, it’s to be worse than it is now.

Just imagine a thousand of them and none of them completely understand each other. And, you know, so so I don’t think that’s a model for the future. I think it’s one of those weird things that happens when we transition from one paradigm to the next one.

I think it is a necessary step for anyone who tries to still make enterprise applications to remain relevant. Even the idea of an application is to be challenged quite hard. right? If you can just tell your phone that you to buy two tickets to go to Barcelona and, by the way, book this hotel and, by the way, can you play this music? Why did you need to know about Spotify, Booking.com, all of this? Why do need to know about any of this?

This is very, very, like, I think actually that one of the biggest impacts of AI in LLMs is that most application based brands are going be really struggling because the brand is the UX. If you’re not touching the button so why are they making copilots? They’re making copilots because they need you into In fact, everybody’s talking about the big problem Google have in search that they are and and their revenue stream. Nobody’s talking about what it means for enterprise application. I’m 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. That’s where the real challenge is going come and they’re going be, I mean, it’s to be fun to watch.

I mean, we were talking about it the other day. I I think, like, it’s almost like the idea of an app almost becomes like TikTok. It’s like, here’s the flavor of the second, you know, Have you tried this thing? Somebody made this really good prompt that generate this fun thing or whatever. So I think in consumer, it is to be absolutely pandemonium. And to try to build a consumer tech brand and hold on to any population of users is to be very, very, very, hard in a world where innovation is almost free and LLMs can make anything.

In enterprise, again, it’s said it’s to be different because there’s so many modes. There’s so many layers of of complexity, regulation, that there’s still a lot of space. And then the last bit is the biggest differentiator in the world to come is to be proprietary data. I’m sorry, but like with a few exceptions, right? OpenAI, BART, all of these are trained on the same set. the public data. Okay. Google have a bit more proprietary data on where you are and your travel email. Meta has some other stuff and so on.

But it’s all the same consumer world.

Yeah, no, and and 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 to be a major problem. I mean, fair use, I think, is covering this fairly well. But I do think it doesn’t matter if you have 10% different data if you train on 1 trillion parameters. it doesn’t matter because it’s such a big set that actually is such a small rounding error in what you get out on the other side.

But what matters is if you have years of proprietary data on how to manufacture certain enzymes or biology, you know, because that’s the stuff.

No. And and I think, look, it’s also the same with, I mean, Tradeshift, absolutely, but also with Beyond Work, which is we know how to build enterprise grade data isolation, security, how to load in these models. mean, look, I’ve spent years convincing the largest companies in the world to give me their supply chain data, put it in the cloud. The first time I did that, people were like, you’re insane. That is never to happen. Do you think that some of the largest phone manufacturers in the world are to give you all the supply That’s the tax got to pay to get to those proprietary data.

And to pay that tax, you’ve to have a full understanding of compliance, regulatory, all of these things. But you’re still not you can’t be Google or whatever because then you just have too many lawyers that’s to say no.

All of the above, I think.

Yeah, Yeah, yeah, yeah, I mean, you can at least, if anything else, you can probably license your IP to have some AI keep doing the podcast. so

whether they’re to like remove it. I know, but that world is to be blown up completely. And I, you ask me, am I scared? I’m a bit nervous about what’s to happen, but I’m mostly excited. I think it’s fun when things are up in the air and we don’t know.

That’s a really good question. I would love talk to Steve Jobs I think he would be one of the most brilliant people to have a discussion with.

Yeah. I mean, I think there will still be a lot of money going into the long tail, but you’re right that concentration will happen in the top. But I think ultimately there’ll still be more companies getting funded just because some of the smartest people I know are just starting to boot up on it now. They spent a year or two thinking, looking a little bit at the hype, and now they’re really getting into it. And I think those startups are to really crush it and avoid a lot of the early generation mistakes.

Yeah. I mean, look, I think it’s interesting, right? Because, I mean, you’re seeing even very big names scrambling to get access to deal flow. At prices. Yeah. And so so I think that’s to be really, really, hard. think for the market, like, what’s to happen? I I mean, look, if you were there when the world switched from on prem to cloud and you could have written the checks, there was a few people who did. Right. Like, Reid Hoffman, he just walked around in San Francisco and looked for any startup that has survived 2008 and just gave them money.

There’s to be something similar, and probably we need a good calling first, but I do think there’s to be something similar happening in this paradigm shift here.

I mean, actually not a whole lot. Like, I mean, one one of the things I was talking to, Craston, who’s Grason, he’s a former head of product at 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 was like really serious scientists doing really serious stuff. And now people are hacking LLM models on Discord. So we have this underground that’s now just hacking and building everywhere, and I think that community is really, really, fun.

We are part of a number of other startups and is in Discord, by the way, now. I mean, it’s so crazy. Like nobody is on Slack that I know in in this environment. And it feels very, very, different from anything I’ve been part of. So I I wouldn’t change a whole lot. I think maybe slow down the papers a little bit so we can have time to read them because it’s like a new papers every day. And And yeah.

That’s a good question. I mean, from, of course, 20VC, VC. But I I think I’ll probably pick somebody like Moonfire, and and it it has a lot to do with the philosophy and how they’re optimizing. Again, I have very mixed record as a seed investor myself, but yeah, I haven’t picked one yet.

It’s a classic thing, like just because you have a great product and a great business model. I mean, if the market is wrong, the market is wrong. And it doesn’t matter how much you pound, like a a fight or whatever. Market traction founder. Yeah.

One, because that is sort of my primary. I mean, you know, if I have a hidden I know and I typically had invested in startups coming out of Denmark because the small network and a lot of them go to San Francisco and so on. as a founder is first because if I know who they are and I know what they’ve done, and I invested in quite a bit of the Tradeshift alumni. Right? So I know those guys. That’s a that’s the first. But then today, I would say I would say market, and I probably flipped it before and traction and market.

I’m hopefully doing something I’m really enjoying doing and having fun, And I’m not thinking about why I hate my work or why I need to just take a break. Yeah, I I don’t know what that is. And and actually, that is exciting. I’m completely open to what that could be.

Thank you so much, Harry. I really enjoyed it.