Interview with Justin Kan

In a captivating interview with Colin and Samir, entrepreneur and investor Justin Kan delves into the extraordinary journey from live-streaming his entire life to selling a company for nearly a billion dollars. What began as a wild, perhaps even foolhardy, experiment transformed into a global phenomenon, but the true story, as Kan reveals, lies not just in the milestones, but in the profound personal shifts and discoveries made along the way.

The Origin Story: 24/7 Reality TV

Back in 2007, fresh off the failure of a web calendar startup named Kiko (which Google promptly crushed), Justin Kan and his co-founders found themselves pitching new ideas to Y Combinator. Kan unveiled a concept so audacious it bordered on absurd: Justin.tv, a 24/7 live reality show where he would stream every moment of his life. In an era before Instagram Live or Periscope, this was technically challenging and socially unprecedented. Paul Graham's partner at Y Combinator, sensing the spectacle, quipped, "I'll fund that just to see you make a fool of yourself, Justin," handing them a $50,000 check with no clear technical path forward.

Despite the initial discomfort – Kan admits he was "very uncomfortable" and woke up the night before launch thinking, "oh sh*t what did I get myself into" – the project exploded into media sensation, landing him on The Today Show and MTV. The core idea, that "people follow people," was a powerful, if unrefined, instinct. Yet, the content itself was often mind-numbingly boring, leading to viewer comments like "your content is extremely boring" and even bizarre incidents like being swatted or having pizzas delivered to his location. However, this raw, unfiltered exposure inadvertently fostered a burgeoning community, as viewers soon asked how they could create their own streams, laying the groundwork for a revolutionary platform.

Key Insights:

• Groundbreaking ideas can come from unconventional, even "foolish," experiments.
• Early content may be "terrible," but the underlying "story of the idea" can still captivate.
• Discomfort can be a catalyst for personal growth and unexpected opportunities.

Key Learnings:

• Embrace the chaos of public feedback; it can reveal unmet demands (viewers wanted to stream themselves).
• Even boring content can build a nascent community if the format is novel and interactive.

The Pivot to Twitch: Finding Focus

Despite its initial media splash, Justin.tv, as a general live-streaming platform, eventually stalled and began a slow decline. Recognizing the impending "cliff," the co-founders searched for a pivot. It was Justin's co-founder, Emmet, who suggested a radical shift: focus entirely on gaming. This was met with skepticism; gaming constituted a mere three percent of Justin.tv's traffic, and to many, "the only content that he actually liked to watch on our site" seemed a flimsy basis for a strategic pivot.

They decided to test the idea, going all-in to support gaming streamers with resources for growth and monetization – the very things content creators seek today. This focus ignited a powerful "flywheel" effect. The rebrand to "Twitch" was a masterstroke, giving the platform a clear, defined identity and audience. As Kan explains, "Justin.tv was kind of a muddled story because it was like, okay, it's... everything from people chatting to like people to sports to... random international content... When we focused on Twitch, it was a lot clearer of a story." This targeted approach not only attracted a dedicated community but also simplified advertising and growth. The results were immediate and staggering: they crushed their goal of 10 million monthly active users, a target set against the biggest gaming video site at the time, in just six months.

Key Changes:

• Transitioned from a broad, undefined live-streaming platform to a niche-focused gaming platform.
• Shifted from being "everything to everyone" to a specific, branded offering for a dedicated community.

Key Learnings:

• Defining a clear audience and value proposition is crucial for growth, both for startups and content creators.
• Focusing on a passionate niche, even if small initially, can unlock explosive growth.

The Billion-Dollar Deal and the Search for Meaning

The journey culminated in 2014 with the sale of Twitch to Amazon for a staggering $970 million. Kan recounts the almost surreal moments of the deal: closing it while at Burning Man, then watching the money hit his Bank of America account while at a wedding in Italy. "Boom there's like more money in bank I didn't even know Bank of America could fit that amount of money," he vividly remembers. It was a moment of immense triumph and relief, shared with his co-founders.

However, the immense success didn't bring the lasting fulfillment many might expect. Kan confesses, the sale "didn't solve my like every problem that I ever had or continue to have." He found himself on the "hedonic treadmill," constantly looking for the "next" bigger achievement, comparing himself to friends who built even larger companies. This led to a profound "crisis of purpose," prompting him to ask a friend, "what is the point of life?" The answer – "you just make your own meaning" – initially pushed him further into extrinsic pursuits, believing he just needed "a bigger company." This period was marked by an unconscious drive for external validation, unknowingly seeking the approval he felt he lacked in his past.

Key Insights:

• Significant financial success does not automatically equate to lasting personal fulfillment.
• The "hedonic treadmill" can lead to a continuous, often unhealthy, pursuit of "more."
• External validation can be a powerful, often unconscious, motivator for ambitious pursuits.

Key Learnings:

• Purpose is not discovered but created; an external outcome won't provide intrinsic meaning.
• Be aware of extrinsic motivations; they can lead to continued dissatisfaction even after achieving major goals.

Justin Kan 2.0: The Intentional Creator

The turning point came during a challenging period, leading Kan to an ayahuasca experience. This deeply introspective journey "cracked me up into all the reasons that I've been an entrepreneur and everything I'd done in my career was always to try to get the approval of other people." It was a profound realization that allowed him to accept this part of himself and then question if that's how he wanted to continue showing up in the world. A pivotal moment during the experience, where an assistant shaman calmly told him, "just breathe and be calm," became a lifelong reminder that "I have the capacity to be calm no matter what is happening on the outside world."

This experience sparked a fundamental shift from extrinsic to intrinsic motivation, leading him to ask, "what do I wake up excited to do that gives me joy?" His answer? Creating content and storytelling. Starting with a podcast purely for intrinsic joy (and consequently, very few views), he eventually met YouTube producer Jen Lee, who encouraged him to bring his stories to YouTube. Now, through his YouTube channel, Kan embraces "edutainment," sharing authentic stories about his journey, including challenges like anxiety and depression, and wellness routines. He admires creators like Emma Chamberlain for their raw, engaging storytelling, which he sees as "Justin.tv 2.0" – an edited, refined version of sharing one's life. His channel's mission is to offer relatable insights, openly stating, "I don't think of myself as like the smartest guy out there or like the hardest working or with the best insights or anything like that. I think of myself as just some sh*t guy." His ultimate message to aspiring entrepreneurs and creators is one of perseverance: "If we could make it and be successful, you have no excuse... we just stuck with it, we didn't give up."

Key Practices:

• Embrace self-reflection and introspection to understand deeper motivations.
• Shift focus from external validation to intrinsic joy and purpose.
• Prioritize wellness routines like meditation to cultivate inner calm.

Key Learnings:

• Authenticity and vulnerability resonate deeply with audiences.
• Storytelling, even without elaborate production, is a powerful tool for connection and education.
• Perseverance and continuous learning are more critical than initial genius or a perfect plan.

"I have the capacity to be calm no matter what is happening on the outside world." - Justin Kan