20VC How Being a Founder Almost Killed Me; We Have Lied to a Generation of Founders The Hardest Truths About Being a Founder Revealed Why AI CoPilot is BS, Seat Pricing is Over & User Interfaces are Stupid with Christian Lanng

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.

• Christian Lang discusses the personal cost of relentless work and the danger of burnout for founders.
• He reflects on the romanticization of becoming a founder without understanding the implications.
• The pandemic exacerbated his feelings of burnout due to the isolation and continuous work in front of a screen.
• Christian experienced a growing aversion to his work, despite his commitment to the company's success.

"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.

• Christian transitioned from CEO to Chairman at Tradeshift after 14 years.
• He made the difficult decision to step back after realizing his unhappiness and reflecting on his well-being.
• The decision to transition was one of the hardest in his life, and he found it challenging to find advice on how to exit a company he built.

"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.

• The realization of burnout was gradual for Christian, with the pandemic serving as a significant catalyst.
• His health and work suffered, and it became evident that he was not in a healthy place.
• The return to normalcy post-pandemic did not bring back the energy and excitement he hoped for, further confirming his burnout.

"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.

• Christian discusses the responsibility of leadership and the sacrifices made for the company's success.
• He acknowledges that personal happiness is often set aside for the greater good of the company and its stakeholders.
• The balance between personal well-being and professional responsibility is a complex and challenging aspect of leadership.

"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.

• Christian was selective in communicating his mental health struggles, sharing with only a few long-term colleagues.
• He felt the need to maintain a strong front for the broader company, despite his personal challenges.
• The expectation to be a symbol of strength and resilience often prevents leaders from openly discussing their mental health.

"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.

• Christian's decision to step back was influenced by the relief he felt at the prospect of someone else taking over.
• The realization that he was in a bad place only became clear after he made the decision to let go.
• His post announcing the transition was prompted by the immense relief and reflection on his mental state.

"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.

• Christian believes that the mantra of never giving up is true but problematic.
• The normalization of entrepreneurship has led many to become founders without understanding the true demands and potential for burnout.
• He acknowledges the difficulty in knowing when to continue persisting with a venture versus when to move on.

"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.

• After stepping back from Tradeshift, Christian focuses on building better work experiences through AI native software.
• He finds excitement in the potential of generative AI and the opportunity to apply his experience in a new context.
• The shift to a new venture allows him to redirect his energy and creativity toward something he is passionate about.

"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.

• Startup success often comes with significant personal sacrifices.
• The probability of achieving financial success in a startup is very low.
• Founders may lose connections with family and friends due to the intense focus on their company.
• Christian Lang mentions that only a few people still talk to him after 14 years in the startup world.

"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.

• Christian Lang nearly died from anemia due to neglecting his health while focusing on his company.
• He emphasizes the importance of health and has since taken his well-being more seriously.
• The intense travel and work schedule of startup founders can have detrimental effects on their health.

"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.

• Christian Lang reflects on the challenges of maintaining a balance between work and family life.
• He regrets missing out on important moments with his child and other family events.
• Lang suggests that having children can force a restructuring of priorities and can help address issues like struggling to wake up early.

"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.

• Christian Lang underwent seven years of coaching to help him cope with his emotions and drive.
• He learned the importance of forgiving oneself for failures and not being too hard on oneself.
• Lang also discusses the impact of childhood experiences on his motivation to succeed.

"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.

• Lang's relationship with money is secondary to his curiosity and desire to explore new ideas.
• He believes that following one's curiosity can lead to success and financial gain.
• Lang also discusses the importance of understanding one's true assets, which for him is his mind, not money.

"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.

• Lang advises founders to not over-optimize on valuation during fundraising.
• He emphasizes the importance of building long-term relationships with investors rather than focusing solely on immediate financial gains.
• Lang also discusses strategies for maintaining leverage in negotiations with investors, such as managing the company's runway.

"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.

• Effective communication with investors is crucial, especially during challenging times.
• Lang reflects on the importance of investor support when the company faces difficulties.
• He advises founders to be selective about which investors they bring on board, ensuring they will provide support beyond just financial investment.

"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.

• Showing vulnerability is crucial for building trust as a leader.
• Vulnerability helps to humanize leaders, making them more relatable and trustworthy.
• Being open about one's weaknesses and struggles can strengthen relationships with team members and investors.
• However, vulnerability can also lead to being taken advantage of, which is a risk that leaders must be willing to take.

"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.

• Maintaining one's authenticity in the face of adversity is a significant challenge.
• Experiencing betrayal or exploitation can make it difficult not to become jaded.
• Choosing to focus on building and future happiness is a way to prevent others from defining who you are.

"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.

• Startups are high-pressure environments that can lead to burnout.
• Mental health is a critical issue that needs to be addressed in startups.
• Leaders must find ways to support mental health without adding to the stress.
• There's recognition that everyone, regardless of their resilience, is susceptible to mental health challenges.

"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.

• Wokeness has its roots in legitimate issues but can be challenging to manage in extreme environments like startups.
• Leaders need to create inclusive environments without compromising the focus on building the company.
• Some founders may exploit the high-pressure nature of startups to justify poor behavior.

"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.

• The intense nature of startups often leads to friendships forming among team members.
• Being friends with your team can complicate professional decisions, such as firing someone.
• There is a trade-off between forming close bonds and maintaining professional distance.

"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 compromise on hiring quality, even under pressure to fill roles quickly.
• Charging higher prices can actually speed up the sales cycle.
• Startups must iterate and make decisions quickly to succeed.
• The competitive edge in Silicon Valley and China is attributed to an extreme focus on execution.

"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.

• There is a need to redefine the modern work experience to make it more human-centric.
• Beyond Work is a concept aiming to automate work and make it more efficient and enjoyable.
• AI has the potential to revolutionize the startup landscape, but there is uncertainty about how it will unfold.

"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 considered a fundamental technology similar to databases or HTML rendering layers.
• The focus should be on user experience and trust, which are integral to design.
• Trust in AI is analogous to trust in self-driving cars, which show visual cues for user reassurance.

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.

• AI should augment human capabilities, not replace them.
• Automating trivial tasks while keeping humans in the loop is the key to effective AI integration.
• AI should be applied where the human brain excels, avoiding turning humans into robots.

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.

• There is a discrepancy between the perceived speed of AI adoption and the actual readiness of corporations.
• Trust and strong human validation loops can accelerate enterprise adoption of AI.

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.

• The cost of innovation will decrease, shifting the focus to execution and ideas.
• A new generation of coders will emerge, utilizing AI assistance for tasks like debugging.
• AI will have a profound and unpredictable impact on society in both the short and long term.

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 seen as a temporary measure for existing applications to stay relevant.
• The future may involve interacting directly with AI, bypassing applications.
• There is a potential for the concept of applications and brands to be challenged in the face of AI.

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.

• Proprietary data will become a key differentiator in the future of AI.
• Startups and private companies with significant data and fewer compliance issues are in a prime position.
• Public companies may struggle with data ownership due to compliance and slowness.

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.

• The speaker expresses excitement, nervousness, and uncertainty about the future of AI.
• There is a sense of anticipation for the changes and opportunities that AI will bring.

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.