In a candid conversation on "The Twenty Minute VC" podcast, host Harry Stebbings is joined by Christian Lanng, former CEO of Tradeshift, who speaks openly about the personal toll of leading a company from startup to unicorn status, including his battles with burnout and the decision to step down. Lanng reflects on the importance of not compromising on quality hires, the need for a better work experience, and his current focus on AI-native software at Beyond Work. The discussion also delves into the future of AI, its rapid integration into the workplace, and the potential obsolescence of user interfaces and traditional enterprise software. Lanng emphasizes the significance of proprietary data and the role of humans in the AI loop, while expressing excitement and uncertainty about the future of AI and its societal impact.
"There's something really, really wrong when the thing you're supposed to love is actually the thing that you can't bear thinking about it. I almost died of anemia. Grid alone don't make you happy, just get the job done right. But the cost for me was very, very high of getting to that other side."
Christian emphasizes the severe personal toll that founder burnout can take, highlighting that mere grit and determination to succeed are not sufficient for happiness and can come at a high cost.
"I've been CEO, co-founder and chairman for Tradeshift for 14 years... And I think this year especially, I have done a lot of reflection over how the last few years has been and also a reflection of not being happy."
Christian shares his introspective journey leading to the decision to change his role at Tradeshift, emphasizing the importance of happiness and well-being alongside professional success.
"It probably started honestly during the pandemic... 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."
Christian describes how the pandemic revealed his burnout, as he began to detest his work environment and the very aspects of his job that he was supposed to love.
"Absolutely. I mean, I've seen that many times during the spring and this year, honestly. Right. And I think, as I also said right 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, you know what? Once those people follow you, then you have a real responsibility because it's pensions on the line, mortgages, children."
Christian reflects on the weight of leadership, highlighting the moral obligation to prioritize the company's well-being over personal happiness.
"There was a very small circle of people in trade shift that's been around for ten 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?"
Christian discusses the delicate balance between being transparent about his struggles and maintaining the image of a strong leader for the sake of the company's morale.
"And I think for me, even when it was just there, the most sort of prone feeling I had after was just relief. I was so relieved to be able to say, okay, somebody else got this."
The quote captures the profound sense of relief Christian experienced upon deciding to step back from his CEO role, indicating the depth of burnout he had reached.
"I mean, 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."
Christian critiques the popular narrative of persistence in entrepreneurship, suggesting that it is not always aligned with the realities and challenges of being a founder.
"And I think back to the burnout side of things. I was also advising on a few things and I was really getting immersed in everything that was happening in generative AI."
Christian expresses enthusiasm for his new direction, indicating a rejuvenation of his interest and passion in the field of AI and its applications in the workplace.
"I'm lucky. I have, like, two or three people that still talk to me after 14 years. But that's about it. Everybody else is like, we used to know you, but we don't."
The quote highlights the personal cost of pursuing a startup, where long hours and commitment can lead to the loss of personal relationships outside of work.
"I almost died of anemia. I just didn't have time to go to the doctor... I went to the doctor and said, I feel really fatigued... And I went off to Las Vegas to do the RA, and in front of the whole company, I mean, I stepped down from stage. There's a text message from a doctor says, go immediately to the nearest ER and tell them your hemoglobin is 5.4."
This quote illustrates the severe health consequences that can result from the relentless pace of startup life and the neglect of personal care.
"Yeah, absolutely. There's lots and lots of things I regret missing. And, I mean, we all have the right parent school meetings, et cetera. One of my friends said being a parent is to permanently feel guilty. That's just how it is."
The quote conveys the perpetual guilt felt by parents who are also entrepreneurs, as they often miss out on family time due to work commitments.
"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... 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, f you."
This quote shows how coaching helped Lang reframe his perspective on success and happiness, moving away from using anger as a motivator.
"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."
Lang expresses that his intellectual capacity and ability to generate ideas are more valuable than financial wealth.
"Remember you're building relationships for 5678, 910 years in some cases, right. And just min max negotiating on the very first contact if you're about to do something together that might be very suboptimal for the whole length, right."
The quote suggests that founders should consider the long-term implications of their relationships with investors and not just the immediate terms of the deal.
"But the investors that I have a relationship with today are the investors that were there 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."
This quote emphasizes the value of investors who remain supportive during the company's tough times, not just during successes.
"No, 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 good at because that helped build a relationship with people."
This quote emphasizes the importance of leaders being open about their strengths and weaknesses to build trust and rapport with their team members.
"I've also plenty of times shown vulnerability and gotten screwed over hard. Right."
This quote highlights the potential downside of vulnerability, where others may exploit a leader's openness for their own advantage. Despite this, the speaker values authenticity over becoming cynical.
"But if you let yourself become jaded, then you let those people define who you are."
This quote underscores the struggle of staying true to oneself after trust has been broken, suggesting that succumbing to cynicism allows others to influence your identity.
"So when I was younger, I thought, how do we deal with mental health in startup? We just make sure we hire people only like that, right?"
This quote reflects a past belief that hiring only resilient individuals could prevent mental health issues, which has since been recognized as an oversimplification.
"You got to create an inclusive environment without going abroad, and then you're just going to focus everyone on one thing and one thing only, and that's building."
This quote suggests that while inclusivity is important, the primary goal of a startup should remain on building and growing the business.
"One of the things we put into what we're building right now is that we are a team, not a family, because let's be real."
This quote captures the sentiment that while close relationships may develop, it's important to remember the professional context of a startup.
"Never ever compromise on quality. When you hire, you will be so tempted."
This quote emphasizes the critical importance of maintaining high standards when hiring, even during rapid growth phases.
"The more we charge, the faster we closed."
This quote reveals an unexpected correlation between higher pricing and quicker sales cycles, suggesting that pricing can influence perceived value.
"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?"
This quote discusses the desire to innovate and improve the way people work by integrating AI and automation into the workplace.
"Most modern work sucks. 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."
This quote contrasts the dynamic and engaging nature of startups with the monotonous and unfulfilling work found in many modern corporate jobs.
AI is essentially as interesting as saying database, or we have an HTML rendering layer or whatever. It's a set of technologies.
This quote emphasizes that AI is a foundational technology and not just a buzzword. It's part of a larger set of tools used in building applications.
It's about trust. And trust, by the way, is a user experience. It's a design exercise.
Trust is highlighted as a critical aspect of user experience, suggesting that it must be intentionally designed into AI systems.
I think humans are incredibly important in the AI loop.
This quote suggests that human oversight and intervention are crucial in AI systems, ensuring that AI complements human work rather than supplants it.
If we can automate all the trivial stuff, that still requires knowledge. That's actually where the sweet spot of capabilities and models are.
Automation should target mundane tasks, freeing humans to focus on more complex and creative work.
I think we are overestimating the speed of adoption with which we think large corporates will adopt AI.
This quote reflects a belief that the adoption of AI in large corporations will be slower than many anticipate due to various factors, including lack of familiarity with new technologies.
We went from in 60 days trialing to the enterprise going, we want this deployed to 3000 people.
A rapid trial-to-deployment timeline in an enterprise context indicates that with the right trust and validation mechanisms, AI adoption can be swift.
I think it will impact society massively, but in ways we can't really predict yet, even in the short term.
The quote acknowledges the significant but uncertain effects AI will have on society, highlighting the difficulty in forecasting its specific impacts.
Copilots are the last breath from the existing enterprise applications to remain relevant.
This quote criticizes the concept of AI copilots as a stopgap solution for outdated enterprise applications, suggesting that a more direct interaction with AI is the future.
The better solution is to remove the application. That's shit. And just talk straight with AI.
Here, the speaker advocates for a more streamlined and direct interaction with AI, bypassing traditional applications.
The biggest differentiator in the world to come is going to be proprietary data.
Proprietary data is identified as a crucial asset, setting companies apart in the AI-driven future.
You've got to have a full understanding of compliance, regulatory, all of these things.
Understanding compliance and regulation is necessary for companies to leverage their data effectively in the age of AI.
I'm a bit nervous about what's going to happen, but I'm mostly excited.
The speaker admits to mixed feelings about the future of AI, indicating both concern and enthusiasm for the potential changes.
I'm hopefully doing something I'm really enjoying doing and having fun.
Looking ahead, the speaker hopes to continue finding joy and fulfillment in their work amidst the evolving landscape of AI.