We burned through $140 million dollars making these mistakes, so you don't have to. 

On this bonus episode, I'm joined by my friend James Beshara, CEO of Tilt, who also recently started Magic Mind. We talk about the mistakes we've made as founders, and our learnings through blood sweat, and tears. Here are some of them:

Check out the full episode for more! (Here's the YouTube version) 

You can find James on Twitter and Instagram.

Go try out Magic Mind and use my code JUSTIN for 50% off. 

A thank to our sponsors Universe and CashApp for making this podcast possible.

THE QUEST MEDIA | CONTENT MEETS SILICON VALLEY | ? YouTube | ? iTunes | ? Spotify | ? Print | ? Bio

I explain the thinking behind some of my best tweets: starting with the product v. distribution debate. 

Check out the tweets here:

Watch this episode in 4K! It's so much more fun: YouTube link. 

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? The Quest Pod in print: https://thequest.media

? Check out The Quest Media: https://bio.thequest.media

Steve Huffman is the founder and CEO of Reddit. I?ve watched his whole journey since we both started as entrepreneurs in 2005: from founding Reddit, getting acquired by Conde Nast, leaving the company and coming back again as CEO in 2015. 

In this episode Steve opened up in a broad ranging conversation that covered the Reddit origin story, his personal growth journey, quitting alcohol, his sometimes contentious relationship to the Reddit community, and more.

Reddit just raised a Series F, bringing its total capital raised to $700M. I think this is a timely moment to revisit Steve's story. You can also check out Reddit's other co-founder Alexis Ohanian's episode here. 

(This episode was originally released as S1:E8 in 2020)

? Stream this episode on YouTube: https://youtu.be/6ZbNt3XZ_fk

? iTunes: https://apple.co/3lU3fZs

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Sasha Grey is one of the coolest personalities on the internet. While she is probably best known for her legendary tenure in the porn industry, she has since found success as an artist. Sasha has transitioned into a writer, musician, and popular Twitch streamer with almost 1 million followers.

Something that really struck me about Sasha is her tenacity and grit, qualities that I think are exclusive to the greatest creators and founders. She went from bussing tables at a steakhouse, saving up a couple thousand dollars, and betting it all on moving to LA to pursue her dream. We discuss her rapid ascent to stardom in the porn industry, why she left it all behind, and the struggle to be taken seriously by people who dwell on the past.

Enjoyed this episode? The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest Pod:

Universe | The best mobile command centre for building your online business and content.

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? Everything Quest: https://bio.thequest.media

Alexandra and Andrea Botez are my favorite content creators in the game right now. The sisters run BotezLive, one of the biggest chess-streaming channels on Twitch and YouTube with over 900,000 subscribers. Since the age of six, Alexandra has fought tooth and nail to earn her recognition and success. These experiences developed the resilience that fueled her professional chess career, and transitioned her into the content creation grind. 

In this episode we dive deep into the gritty reality of what it really takes to become a full-time streamer, lessons from failed startups, learning how to take constructive criticism, and figuring out how to bring authenticity to content creation. If you are an aspiring creator yourself, the Botez sisters have some extremely valuable takeaways - so stay tuned.

Enjoyed this episode? The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest Pod:

Universe | The best mobile command centre for building your online business and content.

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? Watch this episode in 4K: https://youtu.be/AphAW83yano

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?? The Quest Pod in print: https://thequest.media

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I?ve known Alexis Ohanian for almost fifteen years, ever since we were in the trenches together as part of the first Y Combinator cohort. He is best known as the co-founder of Reddit, a fellow former partner at YC, and the founder of his new venture fund, Seven Seven Six. 

Alexis and I became close friends during our time at YC together, and I witnessed the trials and tribulations he went through while building Reddit first-hand. I?ve had the pleasure of watching my friend grow into a great founder, leader, investor, and parent. In this episode, Alexis opens up about his personal struggles during the early days of Reddit, the challenges of modern parenthood, and the philosophy behind Seven Seven Six. I really appreciate Alexis for being so vulnerable in this episode, and I think it is a powerful message that all founders need to hear.

Follow Alexis on Twitter here, and find out more about Seven Seven Six here.

Enjoyed this episode? The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest Pod:

Universe | The best mobile command centre for building your online business and content.

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? Watch this episode in 4K: https://youtu.be/k4x7fF6G2C8

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? Everything Quest: https://bio.thequest.media

Austen Allred is the founder and CEO of Lambda School, an online coding school that doesn?t charge students tuition until they get hired. Growing up Mormon, Austen worked as a missionary and lived out of a car before applying to Y-Combinator. These experiences taught him about resilience, which kept him laser focused on candidate success through media praise and controversy. 

Austen?s mission to democratize education really resonates with me. In this episode, we discuss moving to the Valley, going through Y-Combinator and being caught in the political tensions surrounding free education. We dive into the concepts of ISAs, the future of education and American Dream as a service.

You can follow Austen on his Twitter, and check out Lambda School here.

The Quest x Universe Site-Building Contest (until 17th August):

The Quest Pod is partnering with Universe App to give away $1000 in cash, plus a chance to pitch me your worst startup ideas (and get roasted ) in a YouTube video! The rules are simple:

The entry form is available here.

Enjoyed this episode? The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest Pod:

Universe | The best mobile command centre for building your online business and content.

Cashapp | Spend, save, invest in stocks and cryptocurrency easily

? Watch this episode in 4K: https://youtu.be/Moyq4j4bKBg

? iTunes: https://apple.co/3lU3fZs

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Matteo Franceschetti is the CEO and co-founder of Eight Sleep, a smart mattress company focused on optimizing sleep quality, duration, and recovery through insights and analytics. The company has raised over $40 million since its inception in 2014.

In this episode, we discuss practical advice on improving health and longevity through optimizing sleep, the importance of prototyping your product, and the unique challenges of scaling a hardware company. Matteo recounts the development of his intense competitive drive as a boy growing up in Italy, his pivot into startups coming from a career as a lawyer, the YC experience, learning to be an effective communicator and leader, and the laborious process of finding product-market fit.

The Quest Pod x Universe Site-Building Contest:

The Quest Pod is partnering with Universe App to give away $1000 in cash, plus a chance to pitch me your worst startup ideas (and get roasted ) in a YouTube video! The rules are simple:

Enjoyed this episode? The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest Pod:

Universe | The best mobile command centre for building your online business and content.

Cashapp | Spend, save, invest in stocks and cryptocurrency easily

? Experience this episode in 4K: https://youtu.be/IOpF5W5ufjo

? iTunes: https://apple.co/3lU3fZs

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

When Justin.tv launched in 2007, we had no idea what it would eventually become.

Don?t be fooled; the journey was far from glamorous. In this episode I sit down with my good friends and Twitch co-founders Michael, Emmett, and Kyle to reminisce on the glory days of building Justin.tv and Twitch. We laugh about behind the scenes stories you haven?t heard anywhere else, reflect on the best and worst moments, how we worked well as a team, discuss joy and motivation, and fantasize about solving the problems of tomorrow. 

You?ll hear the importance of building ?bad? things quickly, developing the right mindset for building a startup, and how to stay curious.

Check out the full episode on Justin Kan's YouTube channel here.

Enjoyed this episode? The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest:

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Missed Part 1 of this conversation? Check out last week?s episode, or head over to The Quest YouTube channel for the full episode.

Last week, Conor and I discussed augmenting collective and individual intelligence, evangelical churches, anthropology, and truth-seeking. 

Continuing from where we left off, we dive further into the philosophy behind Roam Research, the concept of networked thought, climate change, empowerment, and self-love. This was a powerful conversation about how communities allow all of us to hold each other accountable, and develop a deeply connected sense of trust.

Enjoyed this episode? The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest:

Universe | The best mobile command centre for building your online business and content.

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? Check out the full episode on YouTube: https://youtu.be/polm57MvmRE

? iTunes: https://apple.co/3lU3fZs

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

You are listening to Part 1 of the episode. The full uncut conversation is available on The Quest Youtube Channel.

Conor White-Sullivan is the founder of Roam Research, a note-taking app that is taking the world by storm. Deeply curious about the ideas of ?networked? and structured thought, Conor spent nine months immersing himself and studying Evangelical Christian communities. 

The first part of our conversation revolves around the topics of Evangelical churches, anthropology and the paradox of choice. We talk about augmenting collective and individual intelligence, and the relationship between community, purpose, and truth-seeking. Stay tuned for Part 2 next week, where we dive into the philosophy behind Roam, networked thought, climate change, empowerment, and self-love.

The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest:

Universe | The best mobile command centre for building your online business and content.

Cashapp | Spend, save, invest in stocks and cryptocurrency easily

? Watch the full episode on YouTube: https://youtu.be/polm57MvmRE

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? Spotify: https://spoti.fi/3srzJwq

?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Gary Vaynerchuck (aka GaryVee) is the truest sense of the word ?entrepreneur? and has established himself as one of the most dynamic and charismatic business personalities on the Internet. Gary is the Chairman of VaynerX and CEO of VaynerMedia; he runs a vastly popular YouTube channel with over 3 million subscribers, and has 20+ million followers across his social media platforms. One thing you can count on is Gary?s uncanny ability to recognize emerging trends in business: he was an early investor in Twitter, Uber, Tumblr, and Snap. As a fellow content creator, I really admire his passionate approach to empowering young entrepreneurs, and his vocalism on topics of consumer behavior and digital markets.

In this conversation, Gary and I talk about everything from his childhood to the idea of living life in a ?cocoon?. Beyond the intense and, at times, polarizing presence he has online, Gary shares the vulnerable moments, stories, and lessons that you won?t hear anywhere else. We share thoughts on materialism, happiness, the power of being an influencer, and the journey to finding what you truly love.

The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest:

Universe | The best mobile command centre for building your online business and content.

Cashapp | Spend, save, invest in stocks and cryptocurrency easily

? Watch this episode in 4K: https://youtu.be/mx8KdSAAxK0

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Robin Chan is a serial entrepreneur, angel investor, and one of my best friends. Last year, we co-founded Goat Capital, a $50 million seed fund. He has been an early investor in some of the biggest companies around the world from Silicon Valley to China, including Uber, Square, Twitter and XiaoMi.

Robin is someone I really admire beyond his business acumen and success. In this conversation, we talk about when we first met while I was still working on Justin.TV, investing in climate change, and meeting Jack Dorsey for the first time. We discuss learning to put yourself in uncomfortable situations, becoming a student of the world, and constantly asking questions. One thing I?ve learned from Robin is the importance of creating an environment focused on giving to others, with no expectations attached. You?ll learn to focus on building meaningful relationships instead of transactional connections.

You can find Robin on Twitter and Linkedin.

The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest:

Universe | The best mobile command centre for building your online business and content.

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? Experience The Quest Pod in 4K: https://youtube.com/c/TheQuestwithJustinKan

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Odunayo Eweniyi is an inspiring and refreshing ambassador for female founders around the world, and I?m very excited to bring you her story. The co-founder and COO of Piggy Vest is a Nigerian business executive and activist. Her accomplishments have earned her recognition in Forbes Africa's list of 20 New Wealth Creators in Africa 2019, Bloomberg 50 2020, and Time 100. 

Beyond her accolades, Odunayo?s entrepreneurial journey was born out of determination and bravery to make a positive change for the world. As we explore her entrepreneurial path, you?ll learn the importance of not internalizing failure, projecting calmness in the face of stress, accepting imperfection, and the strength of patience. She is a reminder to the world that you don?t need to be a ?tech bro? from Silicon Valley to be a successful founder ? you just need the right vision, unflinching determination, and a strong heart. 

You can find Odunayo on Twitter and LinkedIn. 

The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest:

Universe | The best command centre for building your online business and content.

Cashapp | Spend, save, invest in stocks and cryptocurrency easily

? Experience The Quest Pod in 4K: https://youtube.com/c/TheQuestwithJustinKan

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? Spotify: https://spoti.fi/3srzJwq

?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

You are listening to Part 2 of the episode. The full uncut conversation is available on The Quest Youtube Channel. Join the conversation there and drop a comment on what you've learned! 

Picking up where we left off last week, Balaji dives right into the future of Network States and crypto-voting. You?ll learn about the historical relationship between socio-economic ideologies and technological capabilities, and what this means for a crypto future. We discuss how building startups potentiates building cities in the near future, the concept of Crowdchoice, and revolutionizing voting systems with crypto technologies. The new digital frontier is waiting to be conquered, and Balaji is leading the charge.

You can find Balaji on Twitter, and read his personal blog here.

The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest:

Universe | The best command centre for building your online business and content.

Cashapp | Spend, save, invest in stocks and cryptocurrency easily

? Watch the full episode in 4K: https://youtu.be/CHQi1HnCZGY

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? Spotify: https://spoti.fi/3srzJwq

?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

You are listening to Part 1 of the episode. The full, uncut conversation is available on The Quest YouTube Channel. Help us get to 50 comments on YouTube and we will make Part II available everywhere next week! 

It?s Balaji?s world, and we?re all just living in it. If you?ve been hanging out on tech Twitter long enough or listen to any other tech podcasts, then you?re probably familiar with Balaji. He is an angel investor, entrepreneur, and formerly the CTO of Coinbase and General Partner at Andreessen Horowitz. 

In this epic two-part episode, you?ll hear topics ranging from decentralization, crypto, media tech, social networking, China, machine learning, digital privacy and much more. Balaji has one of the most incredible minds I have ever met, and I am excited to bring you along on this journey. 

There is a lot to take in from our conversation, which is why we have decided to release this in two parts. Help us get to 50 comments on YouTube and we will make Part II available everywhere! 

You can find Balaji on Twitter, and read his personal blog here.

The incredible stories on this podcast are made possible by our sponsors, check them out to support The Quest:

Universe | The best command centre for building your online business and content.

Cashapp | Spend, save, invest in stocks and cryptocurrency easily

? Watch the full episode in 4K: https://youtu.be/CHQi1HnCZGY

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

My first company, Twitch, sold for almost a billion dollars. My second one lost $75 million in 36 months. People love talking about success, but today I want to talk about failure. 

Early last year, I announced the closure of my company with a heavy heart. Atrium marks a sinister period in my life consumed by failure and pain, but also one of learning and reflection. Just over a year removed, it is time to be honest and tell the full story behind the fall of Atrium.

In this episode, you will hear about building for purpose, the importance of a clear mission, hiring too quickly, embracing failure, and asking yourself difficult questions. Will you let your failures define you, or emerge a stronger and better person? Read the full article on this topic here, or watch the video I made on this topic here.

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Laura Deming is not your typical VC. She is the founder and partner of The Longevity Fund, a venture capital firm focused on the study of aging and life extension in humans. Home-schooled in New Zealand, she moved to the U.S with her family to work in an age genetics lab at just twelve years old before dropping out of MIT at fourteen following her acceptance as a Thiel Fellow. 

In this episode, Laura and I discuss her journey to become an effective leader, taking risks, dealing with failure, and being motivated to change the world for a better place. Beyond her impressive resume, she is a reminder that great founders can come from anywhere, so long as you have the passion to pursue something relentlessly and are not afraid to step outside your comfort zone. If you are interested in discussions about pushing the boundaries of science, technology, and concepts of biological immortality, you definitely don?t want to miss this episode.

You can find Laura on Twitter and check out her blog here. 

? Experience The Quest Pod in 4K: https://youtube.com/c/TheQuestwithJustinKan

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? Everything Quest: https://bio.thequest.media

Wellbeing in the workplace starts with transparency, vulnerability, and empathy. Mathilde Collin is the co-founder and CEO of Front App, where her mission is to help people everywhere find meaning and happiness with their work. I met Mathilde when she was going through Y Combinator back in 2014, and she has since raised over $138 million in venture capital funding. Mathilde took a leap of faith - she came all the way to San Francisco to pursue her start-up dream from France, despite never having travelled outside of Europe before her interview at YC.

Mathilde is one of the most aware founders I know of. We discuss the importance of viewing founders and CEOs as people, showing vulnerability as a leader. We also discuss accepting change within ourselves and in other people, and its importance in framing ideas of happiness. What I admire the most about Mathilde is how she has been able to challenge the workplace status quo with honesty, empathy and radical transparency. 

You can find Mathilde on Twitter and read her musings here. 

? Experience The Quest Pod in 4K: https://youtube.com/c/TheQuestwithJustinKan

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? Everything Quest: https://bio.thequest.media

Could you imagine what it would be like to suffer a panic attack in front of five million people on live television? Journalist, author, and co-founder of 10% Happier, Dan Harris, was subjected to this terrifying experience as a news anchor on Good Morning America. Since this ordeal, he has embarked on a mission to encourage us to ask an important question: what is happiness, and how can we work towards it? 

I've been following Dan's journey for a long time. His work really resonates with me and I have applied a lot of similar ideas in my own journey to happiness, specifically his advocacy for meditation, exercise, and developing healthy social habits to increase mindfulness. We dive deep into Buddhist concepts, the dangers of extrinsic comparison, the Hedonic Treadmill, rescuing the idea of ?love?, and dealing with depression and anxiety. Despite a world of growing excess, we often still feel like we are missing something. Dan?s mission of encouraging more people to seriously consider happiness is something we need now more than ever. 

His book, 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works, is available on Amazon and everywhere else. You can also find his meditation and wellness app, 10 Percent Happier, on the App Store and Google Play Store.

? Experience The Quest Pod in 4K: https://youtube.com/c/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

This is a story about redemption, pain, forgiveness, and love. Jewel is a four-time Grammy nominated singer, songwriter, actress and author who has sold over 30 million albums worldwide. Behind her incredibly successful career, she has lived an inspiring story filled with spirit and perseverance. 

This is one of the most powerful conversations I?ve ever had, and I am grateful that she was willing to be so vulnerable. In this episode we discuss her rough childhood, resorting to stealing when she was homeless, confronting trauma, and learning to love and forgive. I learned a lot from our conversation, particularly that our pain does not define us, it is how we choose to confront it that shapes us.

? Watch this episode in 4K: https://youtu.be/WWgxyrB1BpQ

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Eric Nam is one of the most exciting powerhouse talents in entertainment. The Atlanta-born talent is a singer, songwriter, TV host, entrepreneur, and K-pop icon, garnering over 300 million streams. Alongside his two brothers, he also runs one of the top podcasts in the industry.

I was told that Eric is one of 'the most loved male artists' in Korea, and now I understand why. While most K-pop idols seem out of our reach, I really appreciate Eric for his down-to-earth personality and authenticity. In our conversation, we discuss his experience growing up as an Asian American, his international non-profit work, struggles with depression, quitting his job, and getting an email the next day to start his K-pop career. 

Eric is an inspiration for me to seize the media space as an Asian American creator. Whether or not you're a K-pop fan, this is an amazing story about finding your calling, chasing after experiences while you're young, knowing when it's ok to quit, building a business with family, and becoming one of the most beloved creators in the world.

This episode was done in collaboration with Subtle Asian Traits, a Facebook group dedicated to Internet discussion surrounding the Asian experience in the West. The Quest team would like to express our gratitude to SAT for helping to source our episode fellow Wooseok, a law student and author of an Amazon Bestseller on K-pop. 

? Experience The Quest Pod in 4K: https://youtu.be/Ol5nu0yw42s

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

On the big screen, the stars of Netflix-hit, Bling Empire, seem larger than life. I was fortunate enough to see the more human side to executive producer Kelly Mi Li, who also stars in the show. 

From living with walls full of rats, to becoming a successful entrepreneur and Hollywood producer, and having $168 million confiscated by her ex-husband in their divorce, Kelly has gone through a lot. She might be known in public by her extravagant personality on-screen, but her lesser-known journey has been one defined by perseverance and hustle.  I have been a fan of Kelly for a while, and this is the first time I got to hear about her come-up story.

Kelly has been a very vocal leader for the Asian community, and I find her especially inspiring as an Asian-American creator myself. In this episode, we discuss the purpose of our work, and what it means to pave the way for others and be inspired by those who came before us. You?ll also hear advice on how to learn to be alone with yourself, and cutting your burn rate to make better financial decisions.

? Experience The Quest Pod in 4K: https://youtube.com/c/TheQuestwithJustinKan

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Garry Tan is a very close friend of mine. The co-founder of Initialized Capital is a veteran entrepreneur, investor, and online content creator. We share a familiar story: a couple of young Asian guys from a family of immigrants in America, building a career in tech, and eventually partnering at Y-Combinator. He also runs a popular YouTube channel, which has inspired me to create my own online content. 

This episode is particularly special to me because of how vulnerable Garry was willing to be, and how deeply connected I felt to him after our conversation. It was his trust in me that allowed us to discuss 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. I am incredibly grateful for the amount of trust Garry has placed in me as a friend. 

This episode is a reminder for me personally that everyone is fighting their own battles. Conversations like this one with Garry represent why I started this podcast: to bring these stories to you.

? Watch this episode in 4K: https://youtu.be/y9ARFwBxz00

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Moses Lo is a survivor. But the co-founder and CEO of Xendit didn?t get there by chance ? he engineered his own luck. I first met Moses through Y Combinator in 2015, and he?s still as scrappy now as he was back then. He had just stepped foot into Silicon Valley, coming all the way from Australia to pursue his ambition. The six week program changed his life forever. 

From an office filled with flying cockroaches, Moses and his team would go on to raise over $80 million and cement themselves as an integral part of payments infrastructure in Southeast Asia. 

I admire Moses a lot, especially his attitude to life. In our conversation, we discuss intentionality and the importance of making choices with conviction. We also talk about what founders can learn from cockroaches: their ability to adapt and survive. You?ll hear about how to make tough decisions, move forward, and design your own luck. 

One more thing: the Asian-American community has recently experienced a surge in discrimination and violence fuelled by hate. Elders have been viciously attacked, murdered and killed on the streets. For this month, we will be highlighting AA community and leaders on this podcast. If you want to help, you can donate here. 

? Experience The Quest Pod in 4K: https://youtube.com/c/TheQuestwithJustinKan

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?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

Molly Bloom started out as a freestyle skier, but somehow found her way into Hollywood through a poker game. Molly had to give up on her Olympic aspirations after sustaining a serious back injury in 2002. During a gap year before law school, she moved to LA and ended up running one of the biggest high-stake poker games in the world (first in LA, then later in New York). Her clientele came from Hollywood?s top 1%, including Tobey Maguire, Leonardo DiCaprio, and Matt Damon. If you've watched the Oscar-nominated movie Molly's Game, you know what happened next: she got robbed at gunpoint and raided by FBI. They seized all her assets, and she became a convicted felon. 

In this episode, we dive into the bigger story: how Molly found her path to redemption, giving up her wealth and status in pursuit of happiness. We talk about the real story behind the movie, her battles with substance addiction, reconnecting with her family and finding closure from her past.

? Watch this episode in 4K: https://youtu.be/STlLk1dC5XE

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? The Quest Pod in print: https://thequest.media

? Everything Quest: https://bio.thequest.media

While many of us were drinking our youth away, Cameron confronted one of the most difficult battles in life: death. He devoted himself to a decade of spiritual pursuit from the age of 20, working at a hospice and preparing for his own death ritual.

He then became a coach, sharing the lessons he learned with business executives in Silicon Valley. He later founded Torch, a leadership development platform teaching empathy, which has raised close to $40 million to date.

I first met Cameron at his clinic. I watched him grow into a startup founder, as I transitioned from building Atrium to beginning my inner journey. In this episode, we sit down to talk about our learnings from both ends of the spectrum: what it?s like to lose a dear friend, being a leader who can empathize with the pains of others, and coming to terms with our own death.

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Transcripts (soon): https://justin.quest?

? Everything Quest: https://listen.justin.quest?

?I don?t know why everything has to happen in f***ing biblical proportions in my life, but it does.?

I resonate with Sophia's story a lot. After bootstrapping her Ebay vintage store Nasty Gal to $28 million in revenue, she was named by Forbes as one of the richest self-made women in America. But in a sudden swing, both her marriage and career fell apart within 3 months. The ultimate dagger: the divorce and bankruptcy news broke while the Netflix show about her life, Girlboss, was aired.

But Sophia didn?t give up. She launched her book, podcast, media company and business class. As a community-college dropout with no pedigree, she proved everyone wrong by going on to start many more businesses, including her newest one, Business Class, which she bootstrapped to a million in revenue in under a year. 

In this episode, we talk about the highlights and lowlights: what happened during that fateful year, how she dealt with the pain and moved forward. Sophia exemplifies what The Quest is about - I am excited and humbled to share our conversation with you.

? Watch The Quest with video: https://www.youtube.com/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Transcripts (soon): https://justin.quest?

? Everything Quest: https://listen.justin.quest?

I started The Quest to share the stories and lessons that I wish I had heard 15 years ago. Building and selling Twitch was an inflection point for me in the past decade. I worked my ass off, made money, took vacations and felt like I was on top of the world. I blew past the goals I had set for myself in the beginning. 

But what was fascinating was that while I felt more accomplished, I wasn?t any happier. I was just holding on to more things. The desire to go bigger and make more nagged constantly at me. After a year and a half at Y Combinator, I left and set out to build another company in the most mercenary way I can think of, then lost millions when it fell apart. 

On this episode, I reflect on the trap of the hedonic treadmill. It led me down a dangerous path chasing material possessions and peer approval - things I thought would fulfil me, but only made me feel perpetually dissatisfied. 

? Watch The Quest with video: https://www.youtube.com/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Transcripts (soon): https://justin.quest?

? Everything Quest: https://listen.justin.quest?

If social media is a game, Josh Richards would have won it before learning how to drive. He isn't just doing the numbers: on top of 24 million followers on TikTok, Josh co-founded an energy drink company, built a creator house and made his name in venture capital as one of the most watched Gen Z VCs. 

But there's much more to his story. Having streamed 4 hours daily for 2 years on a platform that eventually died, Josh grew up knowing the career he chose could end any minute. Though only 19, he has learned his share of life lessons that with a great platform comes great responsibility - despite not having even made it to prom. 

In this conversation we talk about moving to LA, breaking into venture, proving his worth as a board member, and helping shape the creators universe. You can find Josh Richards on TikTok, Instagram and Twitter. 

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Transcripts (soon): https://justin.quest?

? Everything Quest: https://listen.justin.quest?

Born and raised in Germany, Laura Behrens Wu came to Silicon Valley at 22 to intern at a Y Combinator-backed startup. In just 4 years, she decided to 'figure out shipping' and built Shippo, an E-commerce software startup which raised more than $57 million in funding and now serves one-third of businesses exporting from the U.S. 

I met Laura in 2017 and witnessed her incredible growth from a YC intern to a WTO speaker alongside Jack Ma. As the CEO of a 170-person company, she?s had big expectations to live up to. Her struggles as an entrepreneur remind me of the early days of Justin.tv, and her story breaking into the Valley as an outsider is a testament to all young founders worldwide hoping to make it big.

? Shoutout to Asian Hustle Network! We live-streamed this interview with our first community partner Asian Hustle Network, a 70K-strong community empowering Asian entrepreneurial voices. You can check out their podcast here. 

? Watch this episode with video: https://youtu.be/Ew9bmI5aWLc

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Transcripts (soon): https://justin.quest?

? Everything Quest: https://listen.justin.quest?

Mark Cuban needs no introduction. With a net worth of $4.3 billion, he walks around and things just sort themselves out. I have always looked up to Mark as a pioneer in Internet streaming: he was one of the first investors we cold-emailed when building Justin.tv. He did not invest - we were too small for shark food! 

A lot of things changed since then, yet Mark managed to always stay ahead of the curve. His empire grew beyond sports and media into pharmacy, networks and blockchains. He became a father of 3 and considered running for president. I've always wondered how he does it all and I'm very excited to share our conversation with you all. 

? Watch this episode with video: https://youtu.be/4twNOeiZ3XM

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Check out our website: https://justinkan.club?

Carole Robin changed my life. She is my leadership coach and taught the most popular elective at Stanford Graduate School of Business, Interpersonal Dynamics (nicknamed Touchy Feely) for 17 years. Her T-group has helped many of my founder friends, including Jason Tan and Dan Kan (my brother), grow into great leaders at multi-million dollar companies. 

I most admire Carole for her vulnerability-first leadership. Going through her program, Leaders In Tech, helped me learn to label my emotions, and gave me the vocabulary to connect and relate to others without a mask. This is my core mission at The Quest, and I am super excited about her new book 'Connect', where she shares her teachings with the world.

Connect with Carole on LinkedIn and purchase her book here (releasing today)!

Feedback? DM or @ us on Instagram, Twitter, Facebook or LinkedIn

Strapped for time? Sign up to The Quest Digest to get a takeaways summary!

Emmett Shear is my co-founder and the CEO of Twitch, the world's biggest live-streaming platform. Growing up, Emmett and I never lived more than a mile and a half away from each other. We've always wanted to build things: from dreaming of our own Scientology-like religion to launching an experiment with NASA into space (which we actually did as high school students). Many of these experiments failed, one turned out different - and we sold it to Amazon for a billion dollars. 

On this episode, we reminisce on how the past 10 years went. We talk about writing web applications, building Kiko and Justin.tv, what we learned as investors, and whether capitalism works. Being a CEO is challenging - it's especially great to hear Emmett share some of his learnings, many of which I resonate with deeply.

? Watch this episode with video: https://youtu.be/XCzPh-nq4bM

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Transcripts (soon): https://justin.quest?

? Everything Quest: https://listen.justin.quest?

Bryce Hall is the star that Justin.tv (and later Twitch) had hoped to create. At 21 years old, he is a social media phenom with 25M+ followers across platforms such as TikTok and YouTube. Bryce's rise to superstardom started with a yearning for connection: he started live-streaming after being bullied in high school, and in 6 years took over all the headlines and now lives 24/7 in his haters' head, rent-free. 

I knew Bryce from appearing on his podcast, Capital University. I loved his determination and hustle, and invited him to come on The Quest. We talked about making viral content, building a fanbase through the demise of Vine and YouNow, founding Sway House and Ani Energy, and finding TikTok hacks. Bryce is our youngest guest on The Quest, and this was a great crash course on Gen Z for me.

? Watch this episode with video: https://youtu.be/OViNnS2r-20

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Check out our website: https://justinkan.club

Hi guys! The Quest team here. We are supposed to be dropping an episode today on politics, philanthropy and psychedelics. However, that episode is too good that we want to spend a bit more time polishing it up (it's recorded outside, so the audio is not as smooth).

We want to instead launch the first of a mini-series we are doing: Justin's Quest University. Since many of us are attending university via Zoom nowadays, why can't we do it over podcast? We've booked you a 1:1 slot with Justin talking about a Questie-favourite topic: forming habits. In 10 short minutes, listen to Justin's summary of Atomic Habits, a New York Times Best-Seller by James Clear, and his tips on implementing James' tips in your own lives (from home gyms to keto). We hope you enjoy this short tutorial, and will see you again when the semester starts!

? Watch The Quest with video: https://www.youtube.com/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Everything Quest: https://justinkan.club

Jaeson Ma is the most interesting person in the world. He is celebrated as one of the most prominent Asian media moguls of our time, as the founder of East West Ventures, co-founder of 88rising and Stampede Ventures, as well as the Principal of Triller.

But Jaeson is much more: he defies every definition of what the road to success should look like. After selling drugs as a kid, he found Christ, then worked for MC Hammer and later became a missionary and occasional exorcist. He's also recorded an EP with Bruno Mars and led prayers for Jeremy Lin on his first big night before #Linsanity broke out.

Our editor had a hard time choosing what stories to leave out, so we've decided to give you the full Jaeson Ma experience. This is the wildest conversation I've had at The Quest, and I hope you get to enjoy it as much as I did.

? Watch this episode with video: https://youtu.be/VcfrVZSy29s

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Check out our website: https://justinkan.club

LA has always been a tale of two cities. Prophet grew up in the less fortunate one, and spent his formative years in a prision cell. At 16, he served 6 years behind bars, with 9 months in solitary confinement for refusing to stab an inmate.

Luckily, he never lost his soul. Instead, Prophet became an engineer at 22, ran for office at 26 and founded Treehouse, LA's first co-living startup project, at 32. He made it out of the hood - then came back, to build communities, using concrete. For this, he was invited to join First Lady at the State of the Union address in 2015.

I want to kick off 2021 with this story because it is such an incredible journey, and it shows what's possible with hard work, dedication and patience: you get to grow roses, from concrete.

P.S. I did an AMA this week! We've just launched the Quest Fellows application too: you can apply at justin.quest. 

Link to AMA: here. 

Quest Fellows application: here. 

It's finally coming to an end... 2020 has been a crazy year. Going through lockdowns has been stressful, though I spent a lot more time with family and friends I hadn't connected with for a while. I'm glad that many of those moments have been documented on the podcast: my goal is to tell the Justin Kan of 10 years ago what I know to be important today. Doing this gives me peace, and makes me feel happy.

Going into 2021, I want The Quest to evolve with you all. We are launching a Fellows program to co-build the podcast with this community. We want people walking their own paths to be involved in our production process, work with me, and be in the room for when the conversation happens live.

Applications for The Quest Fellows goes live on Jan 5th, 12pm PST. I will be hosting a Reddit AMA at the same time at r/IAmA to answer any questions you might have. Looking forward to what the New Year brings. Happy holidays and stay safe.

? The Quest YouTube experience: https://youtube.com/TheQuestwithJustinKan

? Reddit AMA: link

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Everything Quest: https://justinkan.club

As we head into Season 2 of The Quest in 2021, I want to take you all back to the beginning. I started The Quest to share the stories of those who have found happiness and deeper meaning beyond success. This was inspired by a 15-year journey of my own, often grueling but one which I would not trade for the world.

On this episode, I go back to my roots. I talk to Anne Miura-Ko, one of our first investors in Justin.tv (the company that eventually grew into Twitch) at my alma mater Yale University. We talk about my college days, the experience of being a part of YC's inaugural cohort and working with Emmett and Michael for the first time. We cover the setbacks, the times where I felt lost, and how those times put me on a path in search of fulfillment.

Merry Christmas and I hope you guys enjoy this extra episode.

P.S. watch out for a big annoucement next week for The Quest 2021!

? The Quest YouTube experience: https://youtube.com/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Everything Quest: https://justinkan.club

Amitt Mahajan is the co-creator of Farmville, the single most popular Facebook game that brought in $1B+ in total player purchases. He is also a close friend who introduced me to daily gratitute journaling, a habiting I have kept for two years.

On this epsiode we go through the lessons he learned and unlearned building Farmville, and the path he charted to become the source of his own approval. We talk about lead-climbing for each other, auditing energy and finding our flow machines.

We also announce Kin for the first time in public: the wellness app that Amit and I have been working on for the past six months.

? The Quest YouTube experience: https://youtube.com/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Everything Quest: https://justinkan.club

By popular request: I speak to my brother, Dan Kan about what it was like growing up in the Kan household. Dan is the co-founder of Cruise, a self-driving car company that sold to General Motors for more than $1B.

We talk about the moments from our formative years that set us up as entrepreneurs, founding a company together, learning to talk about emotions, negotiating a billion dollar deal with GM, and much more.

? The Quest YouTube experience: https://youtube.com/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Everything Quest: https://justinkan.club

Matt Gamache-Asselin is one of the scrappiest entrepreneurs I?ve ever met. Five years ago, he was a junior engineer at Facebook, dreaming about startups. Today, he?s the founder of Alto, a digital pharmacy startup that serves tens of thousands of patients and has raised $350M in investment funding. I?ve watched him struggle, survive, and thrive on his journey, and am lucky to consider him a close personal friend.

In the podcast we discuss coming to Silicon Valley and founding Alto, the grind of the early days, conflict aversion, learning from mentors, meditation, and more.

? The Quest YouTube experience: https://youtube.com/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Everything Quest: https://justinkan.club

Janusz Welin is a meditation teacher and the cofounder of Deep Mindfulness Collective. He?s also my meditation teacher, and helped me transform my own life through meditation. Janusz and I talk about his background as an artist, how art relates to meditation, what awakening actually is, how meditation intersects with technology, and much more.

? Check out our YouTube channel: https://youtube.com/TheQuestwithJustinKan

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Everything Quest: https://justinkan.club

I sat down today with my friend Scott Phoenix, founder and CEO of AI startup Vicarious. Vicarious is dedicated to creating Artificial General Intelligence and ushering forth a new golden age of robotics, and Scott has raised over $150m to do it.

Two things I love about Scott: his dedication and focus to a singular mission to create AI, and his adoption of Conscious Leadership, a management philosophy that fundamentally changes the way we relate to ourselves and others. Learning about Conscious Leadership was one of the most impactful things that has happened for me in the past few years. In our conversation we talk about both those things, as well as our relationship with death, the difficulties founding a startup, and much more.

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Everything Quest: https://justinkan.club

Steve Huffman is the founder and CEO of Reddit. I?ve watched his whole journey since we both started as entrepreneurs in 2005: from founding Reddit, getting acquired by Conde Nast, leaving the company and coming back again as CEO in 2015. 

In this episode Steve opened up in a broad ranging conversation that covered the Reddit origin story, his personal growth journey, quitting alcohol, his sometimes contentious relationship to the Reddit community, and more.

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

?? Newsletter: https://thequestpod.substack.com

? Transcripts (soon): https://justin.quest?

? Everything Quest: https://listen.justin.quest?

Arlan Hamilton, the founder of Backstage Capital, a VC firm focused on backing underrepresented minority founders, and one of the most determined people I?ve ever met.

Five years ago, knowing nothing about the technology industry she set out to become a VC no matter what -- even spending time homeless and living out of the SF airport to make it happen. We talk about her new book, resilience and determination, what she?s learned from being an investor in over 150 companies, overcoming alcohol addiction, and more.

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

? Transcripts (soon): https://justin.quest/???? 

? Everything Quest: https://listen.justin.quest/???

A tale of two industries. In this episode we talk to Ranidu Lankage, my cofounder of Whale (among other ventures) and Sri Lankan Pop Artist/DJ. 

In our conversation, Ranidu shared what it was like to grow up in a country during a civil war, his journey of becoming a Sri Lankan pop star, how he got into tech, and all the lessons learned along the way.

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

? Transcripts (soon): https://justin.quest/???? 

? Everything Quest: https://listen.justin.quest/???

In this episode I get ?Closer? with Alex Pall and Drew Taggart, known to the world as the DJ duo The Chainsmokers. I love the energy that Alex and Drew bring to everything they do, and this podcast was no exception.

In a fun discussion, we talk about the early days of hacking Hype Machine to launch their careers, breaking out with Selfie, becoming Grammy winning musicians and DJs, the ups and downs of music and facing depression, and what they look for in founders they invest in. Join us in a first interview and open discussion the duo has had since announcing their social media hiatus this year.

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

? Transcripts (soon): https://justin.quest/???? 

? Everything Quest: https://listen.justin.quest/???

I sit down with Glen Moriarty, psychologist and the founder of 7 Cups of Tea. 7 Cups is a platform that provides online support and has helped over 50 million people. Since I first heard about 7 Cups years ago I loved their mission to connect volunteer listeners with anyone battling loneliness, depression or anxiety, anywhere in the world.

Glen and I talked about wellness startups, getting funded by Y Combinator, the ups and downs of Glen's journey and the power of habits.

? iTunes: https://apple.co/3lU3fZs

? Spotify: https://spoti.fi/3srzJwq

? Transcripts (soon): https://justin.quest/???? 

? Everything Quest: https://listen.justin.quest/???