Divot

Justin Kan helped build Twitch into one of the most influential companies in internet history, changing gaming, streaming, and creator culture forever. After selling the company for nearly $1 billion to Amazon, becoming one of Silicon Valley’s most recognizable entrepreneurs and investors, Justin realized something uncomfortable: achievement alone does not create fulfillment.
In this episode with Derek Andersen, Twitch co-founder Justin Kan breaks down the hidden psychology behind ambition, money, status, comparison, and happiness. He explains why success quickly becomes your new baseline, why social media quietly destroys mental health, how gratitude journaling completely rewired his brain, and why many founders spend their lives chasing goals that never truly satisfy them.
The conversation goes deeper into identity, self-worth, and the emotional cost of ambition, why intrinsic motivation matters more than external validation, the traits Justin looks for in great founders, and why the next generation should build where nobody is looking yet.
Follow Justin - X (Twitter): https://x.com/justinkan
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Google for Startups
Grab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia
Timestamps:
01:40 — Justin Kan’s Tattoo About Gratitude
02:46 — Why Success Still Creates Comparison
03:36 — Why Money and Fame Don’t Create Happiness
06:55 — Why Achievement Only Feels Good for a Moment
10:51 — The Habit That Rewired Justin’s Brain
16:39 — AI, Mental Health, and Social Media
18:10 — Why Justin Isn’t Chasing the AI Gold Rush
21:49 — The Founder Trait Justin Looks For Most
23:19 — Why Justin Invested $8 Million After a Cold Plunge
26:20 — Why You Shouldn’t Chase the AI Crowd
26:44 — The Next Big Frontier After AI
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#justinkan #twitch #siliconvalley #entrepreneurship #startupfounder #mentalhealth #successmindset #founderjourney #personalgrowth #divotpodcast

David Spinks spent years building one of the most respected communities in Silicon Valley, co-founding CMX, advising top companies on belonging, and helping define an entire industry around community building. But beneath the success, achievement, and ambition, he still felt empty.
In this episode with Derek Andersen, David Spinks breaks down the hidden emotional cost of high performance, why so many ambitious people struggle with loneliness, burnout, self-worth, and fulfillment, and why success alone never creates lasting happiness.
He explains the dangerous relationship between ambition and identity, the loneliness epidemic affecting modern society, why high achievers often never feel “good enough,” and how startup culture conditions people to tie their worth to achievement, productivity, and external validation.
The conversation goes deeper into belonging, emotional safety, purpose, fatherhood, mental health, Silicon Valley culture, spirituality, enoughness, and what it actually means to build a meaningful life without sacrificing your well-being, relationships, and inner peace.
Follow David - Instagram: https://x.com/DavidSpinks
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Google for Startups
Grab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia
Timestamps:
03:11 — What Community & Belonging Really Mean
04:34 — The Loneliness Epidemic & Social Media Addiction
06:40 — What It Truly Means to Feel Like You Belong
12:33 — Can Businesses Ever Replace Real Community?
15:39 — How Communities Mirror Human Nature & Leadership
19:40 — Silicon Valley, Success & the Need to Prove Yourself
23:51 — Why Success Never Makes You Feel “Enough”
24:19 — The False Tradeoff Between Ambition & Happiness
28:00 — Elon Musk, Steve Jobs & the Price of Greatness
31:37 — Is Making a Dent in the Universe Worth the Cost?
36:20 — Why “Saving the World” Often Starts at Home
41:04 — The Hardest Lesson: You Are Already Enough
44:22 — The One Idea David Wishes Everyone Believed
45:19 — Best Advice for Overcoming Fear & Hard Things
46:03 — Fatherhood, Presence & What Really Matters
47:27 — Why Measuring Your Life Can Be Dangerous
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#successmindset #highachievers #selfworth #ambition #loneliness #mentalhealth #personalgrowth #burnout #foundermindset #divotpodcast

Shardul Shah has backed some of the most important technology companies of the last decade. From Datadog to Wiz, his investments have helped shape the future of cybersecurity, cloud infrastructure, artificial intelligence, and enterprise software.
In this episode, Derek Andersen, Shardul Shah, partner at Index Ventures, breaks down the mindset behind billion-dollar startups, how elite founders think about AI, venture capital, acquisitions, intuition, ambition, and building category-defining companies.
He explains why most startup founders misunderstand venture capital, why imagination matters as much as execution, and the two questions every entrepreneur must answer before selling their company.
The conversation goes deeper into trust, relationships, founder psychology, ego, and purpose, why the best investors study people more than markets, how intuition shapes billion-dollar decisions, and what separates iconic founders from short-term operators.
Plus, the untold stories behind Wiz’s $32 billion acquisition, Datadog’s early days, Michael Jordan’s influence on competition, Nas, Dave Chappelle, and the investing philosophy behind some of the most successful startup outcomes of the last decade.
Follow Sahil - Instagram: https://x.com/shardul_shah
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Google for Startups
Grab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia
Timestamps:
02:43 — How a Random Encounter Changed His Entire Life
05:16 — Why Great Startup Founders Can Come From Anywhere
08:06 — Why Shardul Refuses to Invest Over Zoom
13:32 — Why Engineers Are Being Measured By Token Usage
14:39 — The Trait Every Billion Dollar Founder Shares
20:09 — The Brutal Truth About Boardroom Disagreements
24:03 — How Building Communities Led To Billion Dollar Companies
27:11 — Why Datadog Looked Like a Terrible Investment
29:03 — The Mindset Required To Invest Before Everyone Else
33:29 — Inside Wiz’s Historic $32 Billion Acquisition
35:40 — The 2 Questions Every Founder Must Answer
36:24 — If You Can 10X Your Company, Never Sell
40:17 — The Difference Between Your Heart & Your Mind
42:00 — The Ancient Philosophy That Changed How He Thinks
49:34 — Why Michael Jordan Obsessed Him With Competition
52:23 — Dave Chappelle, Nas & The Best Night of His Life
54:00 — The Truth About Intuition & Great Decisions
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#shardulshah #wiz #datadog #venturecapital #startupfounders #artificialintelligence #cybersecurity #foundermindset #entrepreneurmindset #divotpodcast

Sahil Bloom grew up with one scoreboard: money. He worked his way into top private equity firms, built a career most would envy, and still felt hollow, until he started questioning what wealth actually means.
In this episode with Derek Andersen, Sahil Bloom, NYT bestselling author of The Five Types of Wealth, breaks down the framework redefining how millions think about success, time wealth, social wealth, mental wealth, physical wealth, and financial wealth.
He explains the arrival fallacy that traps high achievers, why ambition without direction destroys more lives than failure ever could, and how building a "margin of freedom" early determines whether you'll ever actually escape the golden cage.
The episode goes deeper into identity, purpose, and what a good life actually looks like, why your quest matters more than your goals, how to stop living by someone else's design, and the one conversation with his wife that changed everything.
Follow Sahil - Instagram: https://x.com/SahilBloom
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Google for Startups
Grab the new Google for Startups Future of AI report at https://g.co/futureofgenmedia
Timestamps:
01:05 — The 5 Types of Wealth That Actually Matter
02:09 — Why Chasing Money Leads You Off a Cliff
05:16 — Why Success Feels Empty After You Achieve It
07:16 — You’ll Always Want More Money (Here’s Why)
11:40 — Humans Need a Quest to Feel Alive
16:19 — Ambition Without Direction Is Miserable
18:21 — Direction not Speed (The Life Rule That Matters)
20:15 — Why People Stay Stuck in “Good Enough” Lives
27:27 — How to Actually Change Your Life
28:25 — The Danger of Winning the Wrong Game
50:16 — What Real Confidence Actually Means
58:35 — The Best Advice for Doing Hard Things
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#5typesofwealth #sahilbloom #wealthmindset #founderjourney #entrepreneurmindset #purposedriven #timewealth #buildingmeaningfullife #personalgrowth #divotpodcast

Before becoming a global spiritual leader, Neil L. Andersen was a farm boy learning discipline, responsibility, and faith long before the world ever knew his name. For Derek Andersen, this isn’t just another interview, it’s a conversation with his father.
In this conversation, he shares his journey from building a successful business to serving worldwide as a member of the Quorum of the Twelve Apostles, traveling across 50+ countries, and speaking to millions about faith, resilience, and purpose.
He explains how faith is built like a muscle, why humility is the foundation of real strength, and how serving others creates a deeper sense of fulfillment than success alone. He also shares lessons on leadership, discipline, and making decisions that align with what truly matters.
The episode goes deeper into identity, forgiveness, and meaning, why achievement won’t fix how you feel inside, how to navigate suffering, and what people realize actually matters at the end of life.
Follow Neil - Instagram: https://x.com/AndersenNeilL
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Google for Startups
Everything you need to build and scale AI agents, from tools to expert guidance: https://g.co/startupagentguide
Timestamps:
01:14 — The Burden Everyone Carries in Life
02:23 — The Real Game of Life: Good vs Evil
08:23 — Growing Up on a Farm
09:31 — The Experience That Expanded His World
11:21 — From Self to Service
12:40 — Why Helping Others Creates Meaning
16:48 — Faith Is a Muscle
23:41 — How to Rebuild Faith When You’ve Lost It
27:19 — Why Humility Is the Source of Real Strength
30:22 — Speaking About Faith in a Modern World
32:54 — What Happens After Death
40:01 — The Danger of Ego and Recognition
45:08 — The Call That Changed His Life
53:04 — Becoming an Apostle
57:13 — His Core Responsibility
01:03:20 — The Hardest Part: Helping People in Pain
01:14:00 — Forgiveness: Why You’re Never Too Far Gone
01:18:13 — The One Idea He Would Teach the World
01:19:08 — How He Measures a Good Life
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#faith #faithjourney #forgiveness #purpose #meaningoflife #lifelessons #personalgrowth #selfimprovement #mindset #humility #service #familyvalues #fatherandson #spiritualgrowth #resilience #leadership #divotpodcast