Jun 21, 2019 · 34m · 20vc
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
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings speaks with Twitch co-founder and Atrium CEO Justin Kan about his entrepreneurial journey, Atrium's legal business model, and the crucial importance of founder mental health, non-attachment, and conscious leadership.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 31.5% of the talking time here. How this is scored →
Harry as informed peer 2.8 Guest teaching 2.5 Guest disagreement 0.8 Harry pushing back 1.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 26:44 Calling BS on mandatory startup suffering
Justin forcefully rejects the widespread tech narrative that founders must suffer to build a company, calling it total BS while distinguishing hard work from unnecessary martyrdom.
Hardest push from Harry ▶ 24:41 Challenging the feasibility of startup vulnerabilityHarry pushes back on Justin's call for transparency, arguing that founders cannot easily admit severe struggles in a momentum-based ecosystem reliant on constant fundraising.
Biggest teaching moment ▶ 7:00 Educating on legal service resilienceJustin educates Harry on why corporate legal services differ from standard startup software, explaining that legal counsel is required during both good times and bad times.
Harry holds his own ▶ 6:25 Citing Paul Graham on startup customer basesHarry demonstrates industry knowledge by bringing up Paul Graham's writing on selling to high-growth startups and questioning the long-term viability of that economic model.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Justin Kan's Founder Journey from Kiko to Atrium | 1 | 1 | 0 | 0 | Harry welcomes Justin back and asks an open-ended introductory question about his founder journey from Kiko to Twitch and Atrium. Justin provides a lighthearted summary of his career without any conflict or technical pushback. | |
| Business Model and Economic Resilience of Atrium | 4 | 3 | 1 | 2 | Harry asks an off-script question citing Paul Graham's thoughts on selling to startups, challenging whether focusing on high-growth tech startups as a customer base is viable during downturns. Justin explains that legal services remain essential in both economic expansions and contractions. | |
| Reflecting on Safety Nets and Lessons from Bill Walsh | 3 | 3 | 1 | 2 | Harry probes why Justin needed the safety net of YC after achieving significant financial and reputational success. Justin gently clarifies that YC was not a financial or reputational safety net, but rather a structured activity to prevent boredom without total executive weight. | |
| Detaching Self-Worth from Outcomes and the Board Game Analogy | 3 | 3 | 1 | 2 | Harry asks whether detaching self-worth from outcomes contradicts having a clear corporate mission and vision. Justin elaborates using a board game analogy to demonstrate how one can play to win while keeping personal ego separate. | |
| Therapy, Executive Coaching, and Conscious Leadership | 2 | 2 | 0 | 0 | Harry asks about therapy and specific leadership frameworks, referencing the book 15 Commitments of Conscious Leadership. Justin details his adoption of radical responsibility, radical curiosity, and processing emotions at work. | |
| Normalizing Vulnerability in the Tech Ecosystem | 4 | 3 | 2 | 3 | Harry pushes back on the idea of full transparency, asking if founders can truly be vulnerable in a tight-knit fundraising ecosystem where momentum is everything. Justin agrees public transparency is difficult and rejects the myth that startup founders must suffer to succeed. |
Statements from this episode (13)
Kan: Learning as a startup founder is an inherently painful process
“When you're the founder of a startup, you are forced to learn things. The thing I forgot about that process is that when you're learning is actually mostly a painful process. And what I mean by that is it's mostly involves failing at things until you finally g…”
Kan: Incumbent law firms are heavily incentivized not to innovate
“Found a lot of things that I thought were like broken about the legal market and legal industry that created incentives for the incumbents themselves. Not to change.”
Kan wanted to quit Twitch and Justin.tv every single summer
“When I was in my first section of my entrepreneurial career, you know, building Justin TV and Twitch, I remember that every summer I would want to quit and go get a job or do something else.”
Kan: Y Combinator is so stable you "can't fuck it up"
“And the time at YC was nice because YC is very stable as an organization. It's a brand. People want to go there. You know, you kind of like can't fuck it up really. And so the kind of mental burden was like way off by comparison to startups.”
Kan: Founders have a fiduciary duty to investors to avoid burnout
“And if you burn out, you are not doing yourself or your investors or your employees or your customers any favors. You need to like retain yourself. And so you need to create a situation inside your company where you are going to be retained for a long time. I …”
Kan: The happiness of selling Twitch for $1B lasted a week
“When we sold Twitch, Almost a billion dollars. Like I was very happy for one day, two days, even a week. But after that, I was just, I remember, you know, kind of just went, okay, that's the new normal. And now I'm back here at my baseline.”
Kan: Tying your entire identity to your startup guarantees burnout
“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. You transpose those feelings that you might have about what's happening in your company onto y…”
Kan uses a daily phone alarm to meditate on non-attachment
“I have a timer on my phone every day that actually reminds me to meditate on attachment specifically and to remind myself that, you know, 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…”
Kan uses a therapist, two CEO coaches, and leadership groups
“So now, today, you know, I have a therapist, I have a CEO coach, I actually have two CEO coaches, I have different conscious leadership groups that I'm part of”
Kan: Naming emotions at work helps diagnose underlying operational issues
“Being able to name your emotions enables you to actually drive into the deeper issues for what might be triggering them in you”
Kan: Silicon Valley culture makes sharing negative company events nearly impossible
“And even I can't advertise like super things that might be perceived as super negative events. It's really tough to do in our society.”
Kan: It is a myth that founders must suffer to build startups
“I think people feel like they have to suffer in order to do a startup, and I actually just disagree with that. I don't think you have to suffer. You're going to experience pain, definitely. Things aren't always going to go right, but you don't have to suffer.”
Kan: Treating Atrium like an investor was my biggest early mistake
“I think I approached Atrium with a little bit too much of an investor attitude in the beginning, which was a little bit too much like hands off. Like I'm just going to build a team and the team is going to do everything without like really myself getting in th…”