20VC Justin Kan on Why We Have To Normalize Vulnerability in Startups Today, Why Attaching Happiness To Future Outcomes Will Only Lead To Suffering & Why It Is Total BS That You Have To Suffer When Doing A Startup



In this episode of "20 minutes VC," host Harry Stebbings interviews Justin Kan, founder and CEO of Atrium, a tech-enabled corporate law firm for startups. Justin, a former partner at Y Combinator and co-founder of Twitch (acquired by Amazon for $970 million), discusses his entrepreneurial journey, the importance of mental health, and the strategies he's adopted for personal growth and self-improvement. He emphasizes creating a sustainable work environment free from unnecessary suffering and the importance of building a conscious company culture. Justin also delves into the significance of surrounding oneself with mentors and coaches, and the impact of his company Atrium, which aims to provide transparent, efficient legal services to startups. Additionally, he touches on his approach to balancing various aspects of his life and the lessons learned from angel investing.

Summary Notes

Introduction to the 20 Minutes VC Podcast Episode with Justin Kan

  • Harry Stebings, host of the 20 Minutes VC, introduces the episode featuring Justin Kan, founder and CEO of Atrium.
  • Justin Kan has a history of successful ventures, including Twitch, and is a prolific angel investor.
  • The episode will explore topics like lifestyle changes, diet, giving up alcohol, and startup culture.
  • Sponsors include mParticle, Calm, and Botkeeper.

"We are back for another founders Friday here on the 20 minutes VC with me, Harry Stebings and what an episode we have in store for you today."

This quote sets the stage for the episode, indicating an in-depth discussion with founder Justin Kan.

"Our guest, an incredible founder who I've been lucky enough to have on the show before but a long time ago and recently he shared a lot about lifestyle, diet, giving up alcohol and I really don't think we've covered that enough on the 20 minutes VC, and so I'm stoked to dive into that today with the one and only Justin Kan."

Harry Stebings expresses enthusiasm for discussing lifestyle topics with Justin Kan, which are typically not covered on the podcast.

Justin Kan's Entrepreneurial Journey and Founding Atrium

  • Justin Kan started his first startup in 2004, an online calendar called Kiko.
  • Kiko was sold on eBay after failing, leading to the creation of Justin.tv.
  • Justin.tv evolved into Twitch, which was sold to Amazon in 2014 for $970 million.
  • After selling Twitch and other ventures, Kan joined Y Combinator as a partner.
  • He left Y Combinator to return to founding startups, leading to the creation of Atrium.
  • Atrium is a full-service corporate law firm for startups, using technology to improve the legal experience.

"I think I started my first startup in 2004, which was an online calendar, kind of like the Gmail equivalent, very similar to Google Calendar. It's called Keco."

This quote provides background on Justin Kan's early entrepreneurial efforts and the beginnings of his startup journey.

"I decided to go back to the thing that drove the most learning in my life, which was being a founder of a startup."

Justin Kan explains his decision to return to founding startups as a means of continuous learning and growth.

The Viability of Selling to High-Growth Tech Companies

  • Justin Kan discusses the strategy of targeting high-growth tech companies as customers.
  • He mentions the importance of legal services in both good and bad economic times.
  • Kan believes in the stability of the legal market and its necessity for business transactions.

"I do think that with legal specifically, it's one of those things that you use it in good times and you use it in bad times."

This quote emphasizes the resilience of the legal services market and its importance across economic cycles.

Mental Health and Burnout in Startups

  • Justin Kan touches on the growing conversation around mental health in the entrepreneurial space.
  • He reflects on his own experience with burnout during his time building Justin.tv and Twitch.
  • The discussion hints at the importance of self-improvement and the reality of burnout in the startup world.

"I remember that every summer, I would get depressed, and I didn't know why."

Justin Kan shares a personal experience with burnout and mental health challenges during his entrepreneurial career.

Early Entrepreneurial Challenges and Coping Mechanisms

  • Justin Kan discusses his struggles with stress and the temptation of escape fantasies during his first ten years as an entrepreneur.
  • He describes his coping mechanism as "white knuckling" through difficult times without adequately addressing the underlying issues.
  • Justin reflects on the relief he felt after exiting his startups and the contrast in stress levels when he joined Y Combinator (YC), which he found more stable and less mentally taxing.

"And I didn't really deal with it super good in that ten year period. I think I mostly just white knuckled it through it."

This quote indicates that Justin did not have effective strategies for dealing with stress during his early entrepreneurial years, instead relying on sheer endurance to get through tough times.

"The time at YC was nice because YC is very stable as an organization... And so the kind of mental burden was way off by comparison to startups."

Justin contrasts his experience at YC with his previous startup experiences, highlighting the reduced mental burden due to YC's stability and established brand.

The Illusion of Security and the Need for Productivity

  • Justin Kan explains that his need for a security net after entrepreneurial success was not for economic or reputational reasons, but rather from a personal need to be productive and contribute to society.
  • He enjoyed the less stressful environment at YC, attributing it to the established infrastructure and momentum of the organization.

"I think it was more I needed something to do because I'm the kind of person who needs something to know... It felt like I was learning at first, but it was also like all the burden of how we operate or what happens or the future of the organization was not sitting on my shoulders."

Justin expresses his personal drive to be engaged in meaningful work and the relief he felt at YC, where the future of the organization did not solely depend on him.

Insights from "The Score Takes Care of Itself"

  • Justin Kan shares his takeaway from the book "The Score Takes Care of Itself," particularly the cautionary tale of Bill Walsh's burnout despite success.
  • He discusses the misconception that achieving milestones leads to happiness and warns against accepting unhappiness in the present in pursuit of future goals.
  • Justin emphasizes the importance of creating a sustainable work environment to avoid burning out, which is detrimental to oneself and the company.

"You can be burned out no matter how successful you are, and you can be unhappy no matter how successful you are."

This quote underscores that success does not immunize one against burnout or unhappiness, a lesson Justin learned from Bill Walsh's experience.

"I think that's actually very toxic in startups, because in startups, you are a very important actor... And if you burn out, you are not doing yourself or your investors, your employees or your customers any favors."

Justin stresses the critical role of the founder or CEO in a startup and the negative impact their burnout can have on all stakeholders.

The Fallacy of Attaching Happiness to Outcomes

  • Justin Kan and Harry Stebings discuss the flawed notion of tying happiness to specific outcomes, such as audience size, wealth, or company milestones.
  • Justin argues that such outcomes are fleeting and that one's baseline happiness quickly re-normalizes after achieving them.
  • He advocates for working towards goals without letting them define one's identity or self-worth, acknowledging that not all aspects of achieving a goal are within one's control.

"The way I think about it is that basically the idea that you can drive lasting happiness from something that happens externally, like some sort of milestones... those events are always fleeting."

Justin explains that external achievements do not provide lasting happiness, and one's baseline emotional state tends to return to normal after the initial excitement fades.

"And I think that's the reason why you shouldn't do it. People think that it's contradictory to actually having a goal, which is not what I'm saying."

Here, Justin clarifies that he is not advocating for a lack of goals but rather for a balanced approach that separates one's happiness and identity from the achievement of those goals.

Detachment from Self and Company

  • Justin Kan reflects on the challenge of separating personal identity from the company, especially for entrepreneurs whose self-worth can become intertwined with their business's success or failure.
  • He discusses strategies for maintaining mental health and well-being, including meditation, to prevent the negative consequences of this entanglement.

"My entire identity was wrapped up in my company. And being an entrepreneur. And so the problem with that is that when things go badly, you feel badly about yourself."

Justin shares his past experience of identifying too closely with his company, leading to personal distress when the company faced challenges.

"I have a timer on my phone every day that actually reminds me to meditate on attachment specifically and to re"

This quote suggests that Justin has implemented a daily practice to remind himself to meditate on detachment, emphasizing the importance of mental health and well-being in his life.

Importance of Detachment from Goals

  • Recognizing that achieving goals doesn't necessarily lead to happiness.
  • Daily practice of reminding oneself not to be overly attached to outcomes.
  • Emphasizes the importance of being present and mindful.

"mind myself that if I achieve the thing that I want, I think I want actually, I'm not going to actually be any happier, whatever that goal is inside the company or even in my personal life. And so just trying to hold that thought and be present with it every day is one step that I've taken, one very small step."

This quote highlights the speaker's practice of daily reflection on the idea that achieving goals may not bring the expected happiness, suggesting the value of detachment and presence.

Analogy of Life as a Board Game

  • Life and goals compared to playing a board game.
  • Engagement during the game versus detachment after it ends.
  • The analogy suggests a balance between striving for goals and recognizing their transient importance.

"And the way I think about it is I kind of think about your goals in life or your company, or as an entrepreneur, or even your entire life as playing a board game."

This quote introduces the board game analogy, comparing the pursuit of life's goals to the temporary engagement one experiences while playing a game, implying that goals shouldn't be the sole source of fulfillment.

Role of Therapy in Personal Growth

  • Therapy as a tool for dealing with stress and self-discovery.
  • The importance of coaches and mentors in expediting learning and self-improvement.
  • Therapy provides a societal construct for support and catharsis.

"I used to think that could learn everything yourself, and now I'm a huge proponent of just surrounding yourself with the best coaches and mentors possible because that's a way that you can just expedite and speed up your learning and your self improvement."

The speaker advocates for the benefits of therapy and mentorship, emphasizing that external guidance can significantly accelerate personal development and learning.

Implementing Conscious Leadership

  • The book "The 15 Commitments of Conscious Leadership" as a guide for organizational culture.
  • Radical responsibility, curiosity, and emotion acknowledgment as key tenets.
  • The application of these principles in a company setting for improved self-awareness and cultural development.

"The first one is radical responsibility. And I think that one was very easy for me as an entrepreneur to internalize because I've always had this radical responsibility in a way, because you're an entrepreneur, there's no one else coming to save you if something's not working or something bad about your company, right?"

This quote explains the principle of radical responsibility and how it resonates with the speaker's entrepreneurial mindset, underlining the importance of self-accountability in both personal and professional contexts.

Transparency and Vulnerability in the Tech Ecosystem

  • The challenge of being transparent in a momentum-based, tight-knit tech community.
  • The importance of public risk-taking to normalize vulnerability.
  • Creating support networks for sharing vulnerabilities and challenges.

"Yeah, that's really hard. And I think that what's important is that people who can take risks take risks publicly, so that people can see that behavior, and we move the bell curve more towards normalizing vulnerability."

This quote addresses the difficulty of being transparent about failures in the competitive tech industry and the need for leaders to model vulnerability to shift societal norms towards greater openness and support.

Importance of Vulnerability

  • Being open and vulnerable about personal and company challenges is vital.
  • Having an outlet for vulnerability is crucial for well-being.

"And I think that having some outlet for that to be truly vulnerable is really important for people."

The quote emphasizes the significance of having a way to express vulnerability, which is essential for personal well-being and managing the challenges of life and work.

Quickfire Round: Startup Misconceptions

  • Justin Kan dispels the myth that suffering is necessary for startup success.
  • Hard work is important, especially when skills are limited, but suffering is not a requirement.

"I think people feel like they have to suffer in order to do a startup, and I actually just disagree with that."

Justin Kan challenges the common belief that starting a business must involve suffering, suggesting that pain is inevitable but suffering is not.

Exercise Routines and Habits

  • Justin Kan maintains daily workout routines.
  • He uses the streak tracking method from the book "Atomic Habits" to stay consistent.
  • Consistency in exercise is achieved by committing to at least one activity every day.

"The streak tracking mechanism has worked really well for me."

Justin Kan credits the streak tracking method for his consistent exercise routine, which involves doing some form of workout every day to maintain his streak.

Balancing Multiple Ventures

  • Justin Kan focuses on his strengths and delegates other tasks.
  • He is involved in culture and strategy at Atrium and maintains energy by advising founders and building friendships.
  • Delegation and focusing on areas of passion help manage his diverse professional commitments.

"So I really try to delegate everything that is not in my zone of genius."

Justin Kan explains his approach to balancing various professional roles by delegating tasks outside of his core strengths and interests.

Angel Investing and Its Impact

  • Angel investing has helped Justin Kan recognize patterns in good and bad business ideas.
  • However, an investor mindset can be detrimental in the early stages of a startup where a hands-on approach is crucial.

"Having invested in about 100 companies, it's much easier to recognize patterns for what may be a good idea and what might be a bad idea."

Justin Kan shares how his extensive experience in angel investing has given him insight into identifying viable business ideas and strategies.

Future of Atrium

  • Atrium aims to continue building a talented team and improving client services.
  • Innovation in operations and technology is a priority.
  • Building a company culture of radical responsibility and a growth mindset is key to Atrium's vision.

"We just need to execute. And I'm feeling pretty good about our prospects there."

Justin Kan outlines Atrium's future goals, focusing on team building, operational and technological innovation, and fostering a strong company culture.

Personal Support and Advice

  • Justin Kan has provided support and advice to Harry Stebings in his personal journey.
  • The importance of mentorship and guidance is acknowledged.

"Justin's provided immense amount of support and advice to me in my journey."

Harry Stebings expresses gratitude for the support and advice Justin Kan has provided him, highlighting the value of mentorship.

Promoting mParticle and Calm

  • mParticle is promoted as a real-time customer data platform.
  • Calm is advocated for as a sleep aid app.
  • Both services are pitched as solutions to common business and personal challenges.

"mParticle is just so crucial, being your real-time customer data platform."

Harry Stebings endorses mParticle as an essential tool for managing customer data, emphasizing its importance in business operations.

Botkeeper as a Solution for Bookkeeping

  • Botkeeper provides automated bookkeeping with AI and skilled accountants.
  • The service offers 24/7 support and insights through dashboards and reporting.

"Botkeeper provides automated bookkeeping support to businesses by using a powerful combination of skilled accountants alongside machine learning and artificial intelligence."

Harry Stebings introduces Botkeeper as a solution for the often stressful task of bookkeeping, highlighting the integration of technology and professional expertise.

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