Justin Kan: The Philosopher CEO – Below the Line

Justin Kan is a repeat entrepreneur who co-founded Kiko, Justin.tv, Twitch, Socialcam, and now Atrium.

Key Takeaways

  • As a founder, you’re constantly put into situations outside your comfort zone – no matter what happens, you’re going to have to learn
  • Your greatest strengths are also your greatest weaknesses
  • Your emotional state and baseline happiness will NEVER change in a lasting way from ANY outcome or external circumstance
  • As it turns out, most failures aren’t the end of the world. We just build up so much fear and anxiety about imagined worst-case scenarios because we have so much attachment to the outcome.
  • We don’t fear the unknown as much as we fear losing the known
  • Practices that have helped Justin increase his baseline happiness:
    • Gratitude journaling
    • Meditation
    • Negative visualization
    • Therapy
  • Implement systems and rules that prevent your willpower from even playing a role

What’s Justin’s favorite thing about being a founder?

  • He started his first company in 2005
  • “The best part about it is it forces you to grow”
    • As a founder, you’re constantly put into situations outside your comfort zone – no matter what happens, you’re going to have to learn
      • What specifically? – Mainly self-awareness, sales, and recruiting skills
  • Having raised a total of ~$150 million in his career, Justin has an interesting way of looking at his experiences
    • It’s sort of like a 9-figure business school (raising money and then spending it to build a company, all the while learning along the way)

Justin’s Core Skill

  • “The catalytic energy to get ideas moving”
  • But just know – “Your greatest strengths are also your greatest weaknesses”
    • How so? – When you have a lot of energy for new ideas, focus can be a big problem/it’s easy to get distracted
    • As another example – James’ impatient personality led him to start Tilt since he couldn’t find a good job

But what about the downsides of such a long entrepreneurial career?

  • “The human mind can create anxiety, fear, and pain out of situations no matter where you’re at. Whether it’s 1 company over 14 years or 10 companies over 14 year, you’re going to experience a lot of stress, anxiety, and fear.”
    • EVERY entrepreneur, at times, feels like they’ve let their employees/customers down – it’s just something you have to overcome
    • Even if you build a successful/stable company, you’ll still have these feelings
  • The typical cycle
    • An entrepreneur creates a company
    • They then create attachments to what they think will happen to the company (like becoming a billion-dollar startup)
    • Their ego then ties into those outcomes taking place – and this will ALWAYS cause you pain (no matter what the outcome)
      • “Your emotional state and baseline happiness will NEVER change in a lasting way from ANY outcome…any external circumstance”

What’s something Justin thinks a lot about but doesn’t get a chance to talk about?

  • (All the above)
  • “It took me so long into my career before I realized I was optimizing for all these external things, but it wasn’t really giving me anything”
    • The key learning now – you’ll create stress out of any situation if you don’t work on your mental game

Justin’s Quest to Increase His Baseline Happiness

  • The first thing Justin started doing was gratitude journaling every morning with The Five Minute Journal
    • In short – all you do is list 3 things you’re grateful for in addition to 3 things you plan to do to make the day a great one
    • Justin says this exercises really helps re-contextualizes everything going on in his life (all the day’s seemingly huge stressors shrink in importance)
      • It makes you realize how incredibly lucky we are just to be able drive to a pharmacy for something like cold medicine (which would have been impossible 1,000 years ago)
      • “Everything you’re stressed out about today, a year from now you probably won’t even remember”
  • Then Justin started doing a negative visualization exercise
    • What is it? – You just imagine (and write down) the worst-case scenario(s)
    • What does it allow you do? – You’re able to realize:
      • The worst case scenario isn’t all that bad (compared to something like getting a really bad form of cancer)
      • Even if it occurs, you’ll more than likely be able to work your way out of it and adapt
      • As it turns out, most failures aren’t the end of the world. We just build up so much fear and anxiety about imagined worst-case scenarios because we have so much attachment to the outcome.
        • “It’s much bigger a problem in your mind than it is in reality”
  • Justin has also been experimenting with meditation (~40 minutes a day)
  • And lastly, Justin has been seeing a therapist
    • The biggest takeaway – creating space between emotions and your self (not identifying with them)

Loss Aversion

  • “We don’t fear the unknown as much as we fear losing the known” – James
  • “But if you really think about it, you will eventually lose EVERYTHING you have in your life”
    • Fame… gone
    • Health… gone
    • Your life… gone
  • “Change is constant… you can fight it, or accept it. The sooner you accept it, the better off you’ll be.”

Ditching the Phone

  • Justin first tried to get rid of his phone and just use his Apple Watch (which didn’t quite work out well)
  • He recently deleted all the entertainment and email apps off his phone (including the browser) AND locked the ability to install new apps
    • How? – You can delete the app store and put a passcode lock on it for re-installing (which only his wife knows
    • To add – he permanently put his phone in grayscale mode
    • Because of this, Justin has been reading a lot more
  • James has been experimenting with “No Screen Saturdays” in which he only uses his phone for absolute musts

Willpower – Just Remove the Choice Altogether

  • Justin says he actually has really low willpower 
    • As an example – Prior to doing all the above with his phone, he’d frequently have a screen time score of 5 hours+ per day (granted, some of this was email)
  • To combat this, Justin is focused on implementing systems that prevent willpower from even playing a role
    • For example:
      • He exercises every day no matter what
      • He’s now eating a ketogenic diet (so he can’t even think about eating carbs)
    • “It’s about removing choices so you no longer have to make these types of decisions”

Authenticity

  • “I’ve always connected really well with ideas… I love learning about new businesses and technology and new ideas, but I’ve always struggled connecting with other people”
    • Because of this – Justin is working hard on authentically connecting with those around him and genuinely expressing his feelings
  • “In society today, we really don’t tell others how we feel about each other… it feels awkward or we’re scared to express it” – But it shouldn’t be this way

How Lucky We Are

  • There are ~100 billion people who have ever been on this planet
    • “I think in terms of any measurement, whether its security or opportunity or access to resources or education or relationships, I’ve got to be in the top 10 million, which is 0.01%. What a blessing.”

The Stories That Shaped Justin’s Life

  • Getting into Y Combintaor (Justin describes this as one of the luckiest breaks of his life)
    • This is where Justin met his Twitch.tv/Justin.tv co-founder Emit Shear
  • Selling Twitch to Amazon for $970 million
    • Side note – The deal closed while Justin was at Burning Man (how Silicon Valley)
  • About 1.5 years ago, Justin almost drown in the Pacific Ocean
    • He and his wife were learning to spearfish/dive in Sonoma Country
      • The water was fairly choppy so they decided to get out of the water, but the waves kept knocking them off the boat ladder
      • This turned from a minor annoyance to a severe problem to getting tired to yelling for help and thoughts of death
        • “It was the first time I was ever confronted with a situation like that where I really thought it was game over”
      • Sure enough – they managed to get back on the boat and survived 
    • “That was a huge life inflection point for me because it really opened my eyes to the fact that you will die someday.”
      • “Every day is a gift, you’re living on borrowed time”

Additional Notes

  • What is Justin NOT so good at?
    • Mainly operational skills/giving people consistence 
  • “You have to realize that as a founder, you don’t control the outcome entirely. There are lots of things that can happen that are completely out of your control.”
  • You make time for what you care about in life – no matter what it is
  • Check out Justin’s interview with Ryan Hoover
  • ~21% of Americans are dealing with or will deal with depression at some point in their life
    • Only half of these people will at some point seek help through a therapist
  • “Results don’t actually make you any happier”
    • You might be happier for a minute, an hour, or a week… but success doesn’t change your relationships with other people or change your access to doing things that give you joy
  • Model the behavior you want to see in the world
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