Therapy, masks, and destructive expectations


Welcome to The Quest Digest

Read the mind of Twitch co-founder, Justin Kan 🧠. From startup & business advice, to wellbeing, and everything in between.

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In this issue:

  • Quest Minutes: Garry Tan, co-founder of Initialized Capital

  • Blackbird VC x Startmate Fireside Chat

  • The (almost) $1 million Yahoo! deal

  • The Quest is on YouTube!

📹 Quest Minutes: Garry Tan

Designer, Engineer, Investor, Human:

Garry Tan is the co-founder of Initialized Capital, a veteran entrepreneur, investor, and online content creator. Coming from an immigrant family, he has built a successful career in tech and is a former Partner at Y-Combinator. He also runs a highly popular Youtube channel with a focus on providing startup, business, and life advice.

This episode shows an incredibly vulnerable side of Garry. He touches upon topics he hasn’t revealed anywhere else – growing up with an alcoholic father, going through therapy, learning to pull back the mask, and recognizing when expectations can be self-destructive and harmful.

Generational Trauma [2:45]

“The reason why I go that back that far is just that I’m kind of shocked at how far back the pain in my life went back to pain inflicted from many generations back in my family history.”

Garry’s turbulent childhood was shaped in significant part by his father’s alcoholism, the source of many unassuming traumas he would experience throughout his life. With his family’s paycheck gobbled up by either rent or booze, the fearful mindset of scarcity was seared into his mind at a young age.

A painful path descends through his family tree. Garry’s father grew up in a broken home himself: his own father left their family early on and his grandmother was heavily addicted to opium.

Masks [18:25]

“The comments are often like, ‘Garry, you're so Zen. I love your super calming voice, you must meditate a lot’ and I was like, are you kidding? Oh my God. Deep down it's a mess, I am the most self-critical person.”

Throughout Garry’s life, extrinsic markers such as good grades, success, shopping sprees at Banana Republic, and even his YouTube channel have curated a performative version of his identity. This mask was a defense mechanism, a thin protective barrier against the painful world around him.

Letting go of this mask was a terrifying, but necessary step for Garry. Embracing vulnerability and trust was what allowed him to truly connect with others and accept himself in a genuine manner.

Meeting Expectations [24:21]

“If he (Garry’s father) didn't do all of those things, if I didn't walk through frankly, that abuse, but also his expectations and then it's not like he didn't love me… it became very hard for me to learn how to love people the right way, because I had all of these other things attached to love.”

Living up to expectations was a huge driving force in Garry’s success. But it can be incredibly difficult to distinguish when expectations can be harmful or emotionally destructive, especially when it comes to those we love.

Having reconciled the motivations behind his father’s harsh expectations on him, Garry is now striving to find the balance with his own children.

Catch the rest of the conversation with Garry here:

Key Lessons:

  • Start therapy work early. Both Garry and Justin wish that they had started therapy at 22. It took them years to realize that those simple narratives that we tell ourselves aren't always true. The earlier you get to work on yourself, the better. Book in a therapy session and start on that process.

  • It is okay to let down your mask. Behind every mask is a story, and knowing that story helps us to truly connect with each other. Garry has always had a mask on, and he thought letting it down would mean sacrificing his career. But his experiences have taught him that when you are upfront about the battles you are fighting, you gain more respect and affinity as a leader.

  • Expectations can be destructive. A lot of things that are baked into the Asian psyche is the desire to acheive and excel. We often get this from our parents, but slowly they become internalised, and we don't realise it anymore. Garry was really hard on himself when his videos weren't doing well, and he saw how this played subconsciously into the way he interacts with his kids. Knowing how dangerous expectations are, both for ourselves and for other people, is extremely important to finding happiness for yourself and people around you.

Blackbird VC x Startmate Fireside Chat

If you missed Justin’s Fireside Chat event with Blackbird VC and Startmate, make sure you check it out above!

Blackbird is an Australian venture capital firm whose mission is to invest in wild hearts, with the wildest ideas, right at the beginning. You can learn more about them (or apply) here.

The (almost) $1 million deal

If you don’t know the story behind Kiko, Justin’s first company (a calendar app), be sure to check out last week’s newsletter issue to catch up to speed. Alternatively, you can watch the story on YouTube here.

This is the story of how Yahoo left Justin on ‘seen’.

Picking up from where we left off last week, Kiko had just raised $60,000 from an angel round. Through a connection with Paul Graham (PG), Yahoo expressed interest in Kiko as a rival solution to the highly anticipated Google Calendar app.

Things were looking good: Justin and Emmett flew out to the Bay Area, where they got a full VIP tour of the Yahoo campus, and despite a rocky interview due in large part to Justin’s self-admittedly terrible knowledge of programming, Yahoo eventually expressed interest in buying Kiko.

Unfortunately, things started going south from there. Yahoo offered to acquire Kiko for $1 million, a number Justin and Emmett desperately agreed to, despite initially valuing their own company at double the amount. With bated breath, the founders eagerly waited for a call.


The weeks fluttered by, but the promised paperwork never appeared. Yahoo had just effectively ghosted Justin and Emmett. Worse yet, the pair were invited to speak with Google’s development team around this time. This may sound good on paper, but instead of an interview or expression of interest in acquisition, they were essentially interrogated for information about their app, its features, and ideas. Too excited and eager to speak with a big name company like Google, they spilled all the beans, and never heard from them again.

Months later, Google Calendar was released: a much more refined and polished calendar application that also integrated email functions. In the span of a few short months, Kiko’s small existing user-base eventually all jumped ship over to Google.

Key Lessons and Takeaways:

  1. A deal is not done, until it’s ACTUALLY done.

Approach everything with a mindset that is present and grounded. Treat any promises or potential deals as hypotheticals until you’ve signed on the dotted line. Yahoo made a verbal commitment to the $1 million deal, but “deals fall through.” Companies are influenced by a huge spectrum of political or economic variables that may alter the decision making process in any given second.

Deals can fade into thin air, and it can be devestating - be mentally and emotionally prepared.

  1. Don’t necessarily tell people EVERYTHING

If you’re talking with other companies, be careful with how much you reveal about what you’re working on and take it with a grain of salt. Sharing too much information can be detrimental, especially in a competitive market. Play your cards close and only reveal what is absolutely necessary.

The Quest w/ Justin Kan - YouTube Launch

You may have noticed that we’ve been pretty quiet on our social media platforms recently. That’s because during the month of April, Quest HQ has been going all-in on getting our YouTube channel up and running!

We’ve been producing short clips, episode highlights, and editing full-length episodes to be posted on our channel, so make sure you’re subscribed and turn on notifications so you don’t miss anything!

Here’s a clip from one of our most popular episodes with 88rising founder, Jaeson Ma:

The full episode with Jaeson is available on our channel now!

👀 Coming up next…

Kelly Mi Li - star and executive producer of the Netflix reality show Bling Empire, one of the most popular Netflix shows right now! From babysitting at 12, living with rats in her walls, to having $168 million confisticated from her ex-husband after a divorce. It’s a wild ride.

Catch the episode when it drops @ 20 April 9AM PDT. If you’re subscribed to this newsletter, you’ll recieve an email notification, as well as the full transcript as soon as the episode is live! See you there. 👋🏼

Felix Wong is the Editorial Lead & Writer at The Quest with Justin Kan.

You can connect with him via LinkedIn and Twitter

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