Justin Kan opens up (Part 1)

'I've always liked engaging in social media for my own entertainment'

I am a chaplain trying to understand the tech world, and to me, that means I need to understand people like Justin Kan.

Who, after all, most “represents tech?” There are the obvious answers: secular deities like Bill Gates, Elon Musk or the late Steve Jobs. Or there are the often-marginalized figures on whom I’ve often preferred to focus in writing this column: the immigrant women of color who built the industry’s physical infrastructure; social workers and feminist philosophers who study how tech really works on a subconscious level, and how to fix it; or the next generation of leaders who represent the future of tech even as they worry about the inequalities they themselves embody.

But you can’t understand what has come to be the power and mystique of tech without also understanding the minds of its enigmatic founders. Justin Kan is a serial entrepreneur and founder who, whether you appreciate his public voice or not, certainly stands out as one of the most interesting examples of that classic Silicon Valley archetype: a tech entrepreneur ostensibly doing much more than just selling technology.

Kan famously started his business career not long after he graduated from Yale in 2005 by creating Justin.tv, a tech platform from which he broadcast his own life 24/7. Fifteen years later, Kan’s original idea seems quaint, given the level of self-promotion and oversharing that’s become commonplace. And yet, as he was arguably the first person to turn surveillance capitalism into not only overt performance art but also a noteworthy career in startups and venture capital, one can’t help but take the idea of Justin Kan seriously, at the very least as a harbinger of what is to come.

But that was then. As the story goes, the young Y Combinator-backed Justin Kan soon opened his platform to what became tens of thousands of fellow “lifecasters,” which led to his next big pivot: ultimately ditching his original idea to build a company around people live-streaming their video game play, or just 3% of Justin.tv’s customers by around 2011, when it spun off Twitch as a new kind of gaming platform. Of course, Twitch was eventually acquired by Amazon for around a billion dollars, and Kan grew not only his own legend but a life as a VC, both at his alma mater Y Combinator and later at his own firm. And then, earlier this year, Kan announced his latest controversial pivot: After founding Atrium, a $75 million venture-backed new model of legal services company some said had the potential to disrupt Big Law, Kan and Atrium have laid off most of the company’s lawyers.

Maybe this newest move, presented as an attempt to emphasize a sustainable business model, will yield Kan and co. another success story rather than a cautionary tale of disruptive hubris. To me, though, it doesn’t really matter one way or the other.

I tend to look at tech’s profits and losses and its changing business models from a distance. What really interests me about these industries, inside of which we TechCrunch readers all seem to have locked ourselves, is the way that living in a world of technology can change our sense of what it means to live a meaningful life. Who are we in private, when tech means a never-ending public life? What is lasting success, when we’re only as good as our latest “like” or Series B round? And what is real wisdom, when countless bytes of prepackaged “wisdom” litter the internet like straws filling the ocean?

And as you’ll see below if you haven’t already, if Justin Kan has been selling any one thing consistently across his many years of evolving entrepreneurship in several very different business categories, it is a certain approach to pursuing (and then live-blogging) wisdom and the meaning of life.

I only discovered Kan, appropriately enough, by algorithm. A year or so ago, while researching this industry to try to understand it, I started to poke around on tech VC Twitter. Eventually the Twitter app started sending me recommendations. Of course, one just scrolls past most of the content on the website that has perhaps been called a “#hellscape” more than any other, but Kan’s tweets were often the ones I couldn’t scroll past. I would sit trying to figure out what they meant, what kind of ethical values Kan represented.

After speaking with him at the 2019 Disrupt conference in San Francisco, I’m still not sure I have an answer. In part one of our conversation below, however, we cover Kan’s personal journey of coping with childhood anxiety, anger and an acute need for approval, through increasing efforts in mindful self awareness and what ultimately struck me as a uniquely tech-informed strain of contemporary Buddhism. So while I don’t agree with or even fully understand all of Kan’s answers to life’s big questions, if you love tech and philosophy, you’re going to want to read and grapple with them.

TechCrunch: Do you have an audience in mind for your tweets? Who do you picture reading them?

Justin Kan: Myself. I’ve always liked engaging in social media for my own entertainment. Before this Twitter phase started about a year ago, a couple of years ago I was making a lot of Snapchats about business for Generation Z. It was something to do to distract myself [while exercising] because I was very uncomfortable doing cardio. I was not yet comfortable in my own discomfort. I needed a distraction. Then I got a lot of positive reinforcement from people: “Hey, that was helpful. It helped me do something in business.”

More recently, I was going through a period of stress about a year and a half ago, so I started writing out these tweets that were things I was learning or observing about my own experience. Writing a tweet, which is a very succinct piece of writing, is a way to crystallize your thoughts down to one atom, an atomic thing. If I want to learn something deeply, teaching it helps me internalize it as part of my identity.

Thanks — that’s similar to what I was picturing while reading you.

It’s not really to get popular. When I was doing snaps or other times in my life I was trying to figure out what would achieve some goal. With Twitter stuff, it’s really not. I do like the positive feedback, of course. Everybody likes positive reinforcement from other people, but I find that my primary audience is me.

All right, so I’m thinking about how to ask you all the questions I have. Maybe I’m going to need to start by approaching this as if you were someone I was working with in a very different aspect of my career: where I was sitting with you as a chaplain, or even as the person who was officiating your wedding. Which of course I’m not doing; this is an interview for TechCrunch, so I recognize that approach is a little artificial.

No, I’d love to do that. Let’s do that.

I don’t know if you get asked about your childhood a lot.

I’ve been thinking about it a lot recently.

Let’s talk about the basic circumstances of your early upbringing. What I’m most interested in, and not in a judgmental sense, is, what were the qualities of, or what characterized your close relationships with the people around you? How do you think they made you into who you are now?

Every person, in my experience, is a reflection of the scars or whatever that they experienced when they were younger. You adapt and either the pendulum swings one way or the other.

For myself, my dad grew up in Seattle. He’s from Seattle. Chinese ethnically. He grew up pretty poor. My mom was an immigrant from Malaysia. Came to the U.S. when she was 17, also very poor. My mom came from a “not enough” environment. She had nine brothers and sisters. The family didn’t have, there was a scarcity mindset that she carried throughout her life, even though my parents actually became pretty upper-middle class. They had good jobs. My mom was a computer science major, was a programmer for awhile and became a real estate agent. My dad was a finance director at the University of Washington, so they were fine economically, but my mom definitely communicated a scarcity mindset.

Another thing is my dad is a very passive communicator and doesn’t show a lot of outward emotion. And when I was a kid, I always wanted the approval of my peers. I didn’t feel accepted in a bunch of ways. I don’t think anything was particularly unique about my childhood experience in that way. That happens to a lot of people, but that resonated very strongly with me when I was younger.

So you have these twin things: a scarcity mindset and a need for approval. I didn’t really have a good sense of “enough,” I think that shaped me throughout my life. And I should say I don’t blame people for this. [It’s] just the experience that I had.

To what extent were you self-aware at the time of the “scarcity mindset” and the need for approval, as you’re describing them now?

I was not aware of it. I don’t think I was aware of it until six to nine months, a year ago. [I’ve been on a] journey of self-reflection that has opened my eyes to who I really am in a way that nothing has ever done in my past. I had tried to shovel all the achievements in the world into this hole in myself, and it never filled. I succeeded beyond my wildest dreams and I was still the same. Which is not like the worst. I’m just average, a normal person, but I never felt like I had enough. Only when I went inside and started focusing on the introvert world instead of the extrovert world did I learn these things about myself.

And these are some of the topics you have been tweeting about these past several months?

That’s right. It really started about a year ago.

I’m sure there’s a lot in between, but to skip forward: What is the most you’re willing to share about what triggered you to become so much more self-aware in this past year or so now than you were for so much of your life?

It was really stress that was the trigger, and then I started figuring out what are other methodologies and techniques to be at peace in my life. And meditation was a big discovery for me.

Which you discovered when?

Starting last year and then when I’m into something, I just go all in. So I discovered meditation and then for the past 260 days I meditated every day for 40 minutes. That made me much more comfortable in my own discomfort.

Did you have somebody who helped walk you through that process?

I had a teacher, a number of teachers. I had a transcendental meditation teacher, John Bright, and then more recently started doing some mindfulness, positive meditation, so I had a teacher around that.

Then there were other mindful practices, like just being more in touch with my emotions, having a much greater understanding of the quality of my emotions and that they were not something to run from. I think I’ve always been someone who’s been an escapist. I mean I’m an Enneagram Type Seven. Someone who’s been chasing new shit and shiny new experiences, then trying to run away from the bad emotions. So that was another big change for me.

Becoming aware of one’s emotions is not generally or often something that happens so quickly, though. I mean you can learn a meditation technique, but what were the ways in which you found yourself actually being more emotionally aware?

It’s just looking at, where is it in your body? Okay, you feel angry. I feel angry. Where is that in my body? Why do I feel angry? What are the triggers? What were the root causes of this anger? What are the things in my past that might make me a person, today, who would get angry because of this thing? How do I want to react now that I know that I’m angry? Do I want to be swept away with my anger or do I want to acknowledge it and choose how I want to interact with people? How can I explain this to people around me? Can I talk out loud about it? And am I comfortable with that?

Just going through that process with everything I feel: the joy, the anger, the anxiety, the guilt, the love that I experience. That has been a life changer because I used to think that if I just get enough success, then I’ll experience love. I’ll experience joy. But you’re a chaplain, you know that’s not true. I know that’s not true now. Human experience is going to involve things that I would think of as negative. Guilt, anger or sadness. Being okay with it, at peace with it, has been one of the things I’m trying to practice.

You’re in a community, or at least a milieu, that includes a lot of startup people, venture capital people, law people. How are people reacting when you share these sorts of ideas?

There are two reactions. One is, “What the fuck is this guy talking about? Is he for real?” And then the second one is “Thank you.” I mean even walking out in San Francisco I’ve got people coming up to me [saying], “Thanks for talking about this.”

I was at a conference and someone [said], “Thanks for making it okay to talk about therapy. I’m seeing a therapist now.”

I do think that’s nice: that [the message is in] the zeitgeist. But I didn’t invent any of this shit. I want to make that super clear. I don’t think I came up with anything unique. These practices have been around. All the spiritual traditions have some core of contemplative meditative practice. And so I just learned the shit from great people who came before me. I’m just bringing it to a community. That might be even too grandiose of a statement. I’m just one voice in delivering it to a community.

Certainly you’re talking about these topics out loud in a tech community in which there aren’t tons of people doing so.

I think that’s right, but even beyond technology, the pendulum of society has swung back and forth and I think lots of people are talking about this now. [For example,] David Brooks’s “The Second Mountain.” Society has gone from this hyper-individualism, me, me, me, the eighties times 100 with Instagram. We’ve built this torture engine where people compare themselves to each other. They have built deep-rooted anxiety and they’re completely triggered by this constant stream of comparison and feeling like they’re not enough.

I was living that and I found some of these practices that are old technology, Buddhist technology, or from other spiritual traditions, to be a salvation. I think other people want that in their lives, whether they’re in technology or not. I actually think it applies well beyond technology to most people living in the modern world. If I can help deliver some of that message to people, then that is very gratifying.

And even in the technology world there’s been a lot made, both recently and in the past, about places like the Esalen Institute which is very non-coincidentally not that far from where we’re sitting right now. Steve Jobs is another classic example, right? He developed this huge passion for the same kinds of traditions and techniques that you’re talking about.

Yeah. They’ve always been here in Silicon Valley. I mean San Francisco has been the center of a lot of bringing Eastern tradition here.

Nonetheless, and correct me if I’m wrong, but despite that, I would say the majority of people in your milieu, or at least the majority of men, but I suppose unfortunately the majority of men would be the majority of people in that group, have a hard time talking about their emotions, their need for approval, and what to do about it all.

I think it extends to all of modern American society. Every industry, every job, people do not talk about this. Tech just has a spotlight because it’s kind of in the zeitgeist right now. Everybody sees young guys like me getting rich or whatever and they want to be here, they want to be at Facebook or whatever, but I think this applies to finance in New York, the entertainment industries in LA. Every industry has this problem. American culture has this problem.

And law. I mean, you’re in the law business.

Yes. Law has it.

Your company could almost be described as a law firm.

Yes. There’s technical reasons why it’s not actually a law firm.

It’s the new model for what a law company could be beyond calling it a law firm. Is that fair to say?

That’s right. It’s like a technology-driven legal services company for startups.

My wife is a lawyer. I’ve always thought she should start something like that. But in any case, lawyers are not known for their emotional intelligence.

No. But I think that that’s a little bit of a red herring. People always say lawyers aren’t, but nobody is. Nobody in modern corporate America. Modern American society really shuts down people’s [emotional intelligence]. It doesn’t give you the tools to understand your emotions and doesn’t encourage you to bring your emotions and your whole self to work. You could suppress your emotions and say, “I don’t have them in my job.” But you’re lying to yourself, you’re lying to people out there in the workplace because you do have those emotions. If you shut them down and don’t bring them to work, you’re discarding very valuable data. And [emotions] become long-standing internal problems for you if you’re not able to express them. I really believe that.

All right. I want to take this in a slightly different direction now. Given everything we’ve discussed thus far, to what extent would you say that you’ve developed a philosophy of life for yourself? When I read your writing, or at least your micro blogging, sometimes I find myself trying to figure out, “what is the philosophy from which this is coming?”

Sure. Once again, I really want to emphasize, I don’t think I’ve invented anything.

No, but there’s a difference between inventing a philosophy of life and having one.

Yeah. So I do think I have one. I think it’s basically Buddhism. It’s a belief that all of my suffering comes from attachment and aversion and freeing myself of attachment and aversion will lead to the cessation of suffering in my life.

I think the more interesting question is, what is the practical way that I’m trying to do that? For me, it’s about the application of certain things. A lot of people have this instinct but it’s very hard for them to actually live it in their lives. And so for me, I try to find what are the ways to make things easier for me to live [Buddhist philosophy] in my life. And that involves a lot of things. It’s social proof, it’s reinforcement of changes in my identity, it’s habit tracking and making sure that I’m consistent. It’s about designing systems where I don’t have to use willpower because I think human beings have a limited amount of willpower. And so just creating healthy systems for myself, where I don’t have to make choices; my default is to do the healthy thing.

So that might be a little bit more like the Silicon Valley aspect of it: How do you create a system or a hack to do it? One day I would like to write all of this into a book for people.

Clearly, it would be a well-written book.


In Part 2, Kan and I will discuss what, for conflict-avoidant people like ourselves, probably amounts to a “Twitter beef” on the ethics of tech, Buddhist philosophy and atheism/secularism/humanism; the potential dangers of mindfulness and the real source of morality; and what a spiritual approach to startups and tech has to say about problematic capitalism.