Divot

James Dumoulin built School of Hard Knocks into a 22M-follower business media empire by turning street interviews into a new form of financial education. By 23, he had interviewed 52 billionaires and major icons like Tom Cruise, Tom Brady, and Shaquille O’Neal, after once posting hundreds of times with almost no audience.

In this episode with Derek Andersen, James breaks down the creator economy, the pivot that changed everything, and how he mastered organic content, watch time, hooks, and distribution. He explains why the first 3 seconds decide whether a video survives, why quantity creates quality, and how founders can use content to build real business leverage.

The conversation goes deeper into rejection, courage, and credibility, from asking Mark Cuban for his first billionaire interview to scaling toward one of the biggest business media networks in the world. James shows what it really takes to earn attention before anyone gives you permission.

Follow James - Instagram: https://www.instagram.com/realjamesdumoulin
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:
01:48 — How School of Hard Knocks Started
03:56 — 400 Posts With Only 50 Followers
04:41 — From $100K Months to $1M Months
06:15 — How Small Teams Can Win With Content
09:24 — The Only Metric That Matters Online
10:20 — Why the First 3 Seconds Decide Everything
13:03 — How Travel Shaped James’ Ambition
14:25 — Turning Rejection Into Fuel
15:41 — Interviewing 52 Billionaires by 23
15:52 — How James Got Mark Cuban
17:30 — Tom Cruise, Brady, Shaq, and Bigger Asks
20:08 — Why Business Takes Courage
20:50 — Building One of the Biggest Business Media Networks

Follow Divot:
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LinkedIn: https://www.linkedin.com/company/divotdotorg

Hashtags:
#jamesdumoulin #schoolofhardknocks #contentcreation #goingviral #watchtime #entrepreneurship #businessmedia #founderjourney #creatoreconomy #divotpodcast

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
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:
#justinkan #twitch #siliconvalley #entrepreneurship #startupfounder #mentalhealth #successmindset #founderjourney #personalgrowth #divotpodcast

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
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:
#justinkan #twitch #siliconvalley #entrepreneurship #startupfounder #mentalhealth #successmindset #founderjourney #personalgrowth #divotpodcast

Navin Chaddha is the Managing Partner of Mayfield, one of Silicon Valley’s most legendary venture capital firms with over $3B under management and more than 120 IPOs. A 17-time Forbes Midas List investor, Navin was an early backer of companies like Lyft, HashiCorp, Poshmark, SolarCity, and Nuvia, which sold to Qualcomm for $1.4B.

In this episode with Derek Andersen, Navin Chaddha breaks down why AI may become a bigger technological shift than the internet, why tools like Claude are changing software engineering forever, and why AI agents could replace many traditional SaaS workflows. He explains how companies like Nvidia, OpenAI, and Anthropic are building the new “intelligence grid,” why infrastructure wins first in every major technology revolution, and where founders should focus as AI-native startups begin disrupting entire industries.

Navin also shares why founders who embrace AI-native thinking early may gain one of the biggest advantages of the next decade, while incumbents that resist the shift risk being left behind.

Follow Navin- X (Twitter): https://x.com/NavinChaddha
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:
01:14 — Why AI Is a “100x Force” for Humanity
02:27 — Where the Biggest Value in AI Is Being Created
04:19 — Nvidia, Infrastructure & the AI Gold Rush
06:02 — The Next Massive Opportunities Beyond Compute
08:03 — Why Claude Changed Software Engineering
10:05 — Claude as the “New Browser for Work”
12:31 — AI Agents & the End of Traditional SaaS
15:08 — The Rise of Headless Software Explained
18:12 — Why Everyone Can Now Become a Builder
21:05 — Human + AI Teams Will Replace Old Workflows
23:16 — Navin Chaddha’s Biggest Advice for Founders

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:
#aiagents #claudeai #artificialintelligence #futureofwork #openai #anthropic #saas #navinchaddha #nvidia #machinelearning #futureofsoftware #startupfounders #techpodcast #airevolution #siliconvalley #automation #founderjourney #venturecapital #aiinnovation #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
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:
#faith #faithjourney #forgiveness #purpose #meaningoflife #lifelessons #personalgrowth #selfimprovement #mindset #humility #service #familyvalues #fatherandson #spiritualgrowth #resilience #leadership #divotpodcast

Brian Santiago is the Athletic Director at BYU, one of the most respected leaders in college sports. Over nearly three decades inside BYU athletics, he rose from the coaching staff to Athletic Director, helping lead one of the most competitive and values-driven programs in the country into the Big 12 and national relevance.

But his journey wasn’t just about winning. From losing control as a young competitor to learning how to channel intensity, Brian shares the defining moments that shaped his leadership. From showing up for athletes in their hardest moments to building meaningful relationships across the world, this conversation reveals what it actually takes to lead at the highest level.

This episode goes deeper into belief, identity, and what winning really means. Brian breaks down why we are all born to win, why most people never reach their potential, and how to develop a competitive edge without losing yourself. It’s a powerful reminder that success without character is empty, and that the real game is who you become.

Follow Brian - Instagram: https://www.instagram.com/bsant25
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:
00:01:31 — Jimmer Fredette & What Real Greatness Looks Like
00:04:04 — 163 Shots, Almost No Misses (Inside Elite Competitors)
00:06:18 — Why Great Leaders Always Show Up for Their People
00:10:14 — The Power of Relationships (This Changes Everything)
00:12:34 — Why Most People Stop Seeing Others
00:19:57 — The Jacket Story (Real Leadership in Action)
00:25:12 — Turning an Enemy Into a Fan (The “Snake” Story)
00:27:53 — Why BYU Is “One of One” (Faith, Discipline & Focus)
00:31:05 — Why Top Athletes Choose Purpose Over Money
00:41:27 — We Were Born to Win (The Core Philosophy)
00:42:25 — The Lesson That Changed His Life (Control vs Intensity)
00:46:40 — “I Didn’t Come Here to Watch” (Winner Mentality)
00:59:27 — Find a Way. Never Let Up. (Final Message)

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:
#leadership #highperformance #mindsetshift #personaldevelopment #winningmindset #successprinciples #businessstrategy #divotpodcast

Tina Roth-Eisenberg is one of the most influential community builders in the world, founder of Creative Mornings (25,000+ people, 70+ countries), and the creator behind multiple iconic products like Tattly, TeuxDeux, and CreativeMornings’ global movement. Often called the Michael Jordan of community, she has spent nearly two decades building brands, products, and spaces that bring people together at scale.

Before all of that, she felt completely alone after moving to New York. That experience led her to create a simple, free gathering that turned into a global movement. In this conversation with Derek Andersen, she breaks down why most communities fail, why generosity beats monetization, and how the best communities become self-sustaining.

This episode goes deeper into identity, success, and what actually matters. Tina explains why success won’t fulfill you, how to move from your head to your heart, and why community is ultimately how we heal in a world that has become transactional.

Follow Tina - X (Twitter): https://x.com/swissmiss
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:
04:32 — Why Creativity Dies When Life Feels Too Comfortable
06:36 — The Loneliness That Sparked Creative Mornings
07:49 — The Simple Idea That Built a 25,000+ Global Community
09:10 — When You Know an Idea Has Real Momentum (Google + Mailchimp)
11:11 — The Feeling of Real Community (Why People Come Back)
13:53 — Community Is How We Heal
15:17 — Generosity vs Monetization (Why Most Communities Fail)
17:48 — What Makes a Community Actually Work (Values + Trust)
18:54 — Why People Crave Community More Than Ever
25:15 — The Journey From Head to Heart
35:17 — The Book That Changed How She Builds Community
36:11 — The Hardest Lesson: You Can’t Escape Yourself
37:04 — The Limiting Belief That Holds Most People Back
41:02 — Redefining Success: Peace Over Achievement

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:
#communitybuilding #creativemornings #leadershipmindset #personaldevelopment #founderjourney #businessstrategy #networking #divotpodcast