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by Derek Andersen
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- 6 days ago48 min
#49: Success, Loneliness, Ambition & Why High Performers Never Feel Enough | David Spinks
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/DavidSpinksFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmediaTimestamps:03:11 — What Community & Belonging Really Mean04:34 — The Loneliness Epidemic & Social Media Addiction06:40 — What It Truly Means to Feel Like You Belong12:33 — Can Businesses Ever Replace Real Community?15:39 — How Communities Mirror Human Nature & Leadership19:40 — Silicon Valley, Success & the Need to Prove Yourself23:51 — Why Success Never Makes You Feel “Enough”24:19 — The False Tradeoff Between Ambition & Happiness28:00 — Elon Musk, Steve Jobs & the Price of Greatness31:37 — Is Making a Dent in the Universe Worth the Cost?36:20 — Why “Saving the World” Often Starts at Home41:04 — The Hardest Lesson: You Are Already Enough44:22 — The One Idea David Wishes Everyone Believed45:19 — Best Advice for Overcoming Fear & Hard Things46:03 — Fatherhood, Presence & What Really Matters47:27 — Why Measuring Your Life Can Be DangerousFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#successmindset #highachievers #selfworth #ambition #loneliness #mentalhealth #personalgrowth #burnout #foundermindset #divotpodcast
- 1 weeks ago56 min
#48: Wiz, Datadog & The Mindset Behind Billion Dollar Companies | Shardul Shah Index Ventures
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_shahFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmediaTimestamps:02:43 — How a Random Encounter Changed His Entire Life05:16 — Why Great Startup Founders Can Come From Anywhere08:06 — Why Shardul Refuses to Invest Over Zoom13:32 — Why Engineers Are Being Measured By Token Usage14:39 — The Trait Every Billion Dollar Founder Shares20:09 — The Brutal Truth About Boardroom Disagreements24:03 — How Building Communities Led To Billion Dollar Companies27:11 — Why Datadog Looked Like a Terrible Investment29:03 — The Mindset Required To Invest Before Everyone Else33:29 — Inside Wiz’s Historic $32 Billion Acquisition35:40 — The 2 Questions Every Founder Must Answer36:24 — If You Can 10X Your Company, Never Sell40:17 — The Difference Between Your Heart & Your Mind42:00 — The Ancient Philosophy That Changed How He Thinks49:34 — Why Michael Jordan Obsessed Him With Competition52:23 — Dave Chappelle, Nas & The Best Night of His Life54:00 — The Truth About Intuition & Great DecisionsFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#shardulshah #wiz #datadog #venturecapital #startupfounders #artificialintelligence #cybersecurity #foundermindset #entrepreneurmindset #divotpodcast
- 2 weeks ago1h 1m
#47: The 5 Types of Wealth & Why You’re Chasing the Wrong One | Sahil Bloom
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/SahilBloomFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://g.co/futureofgenmediaTimestamps:01:05 — The 5 Types of Wealth That Actually Matter02:09 — Why Chasing Money Leads You Off a Cliff05:16 — Why Success Feels Empty After You Achieve It07:16 — You’ll Always Want More Money (Here’s Why)11:40 — Humans Need a Quest to Feel Alive16:19 — Ambition Without Direction Is Miserable18:21 — Direction not Speed (The Life Rule That Matters)20:15 — Why People Stay Stuck in “Good Enough” Lives27:27 — How to Actually Change Your Life28:25 — The Danger of Winning the Wrong Game50:16 — What Real Confidence Actually Means58:35 — The Best Advice for Doing Hard ThingsFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#5typesofwealth #sahilbloom #wealthmindset #founderjourney #entrepreneurmindset #purposedriven #timewealth #buildingmeaningfullife #personalgrowth #divotpodcast
- 3 weeks ago1h 19m
#46: Elder Neil L. Andersen (Faith Conversation with a Latter-day Saint Apostle, My Dad)
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/AndersenNeilLFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:Google for StartupsEverything you need to build and scale AI agents, from tools to expert guidance: https://g.co/startupagentguideTimestamps:01:14 — The Burden Everyone Carries in Life02:23 — The Real Game of Life: Good vs Evil08:23 — Growing Up on a Farm09:31 — The Experience That Expanded His World11:21 — From Self to Service12:40 — Why Helping Others Creates Meaning16:48 — Faith Is a Muscle23:41 — How to Rebuild Faith When You’ve Lost It27:19 — Why Humility Is the Source of Real Strength30:22 — Speaking About Faith in a Modern World32:54 — What Happens After Death40:01 — The Danger of Ego and Recognition45:08 — The Call That Changed His Life53:04 — Becoming an Apostle57:13 — His Core Responsibility01:03:20 — The Hardest Part: Helping People in Pain01:14:00 — Forgiveness: Why You’re Never Too Far Gone01:18:13 — The One Idea He Would Teach the World01:19:08 — How He Measures a Good LifeFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#faith #faithjourney #forgiveness #purpose #meaningoflife #lifelessons #personalgrowth #selfimprovement #mindset #humility #service #familyvalues #fatherandson #spiritualgrowth #resilience #leadership #divotpodcast
- Apr 15, 20261h 20m
#45: The Mindset That Builds Champions | BYU Athletic Director Brian Santiago
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/bsant25Follow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:Google for StartupsEverything you need to build and scale AI agents, from tools to expert guidance: https://g.co/startupagentguideTimestamps:00:01:31 — Jimmer Fredette & What Real Greatness Looks Like00:04:04 — 163 Shots, Almost No Misses (Inside Elite Competitors)00:06:18 — Why Great Leaders Always Show Up for Their People00:10:14 — The Power of Relationships (This Changes Everything)00:12:34 — Why Most People Stop Seeing Others00:19:57 — 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 Money00:41:27 — 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/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#leadership #highperformance #mindsetshift #personaldevelopment #winningmindset #successprinciples #businessstrategy #divotpodcast
- Apr 8, 202644 min
#44: Why You Feel Disconnected, How She Built a 25,000+ Global Community | Creative Mornings Founder
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/swissmissFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:Google for StartupsEverything you need to build and scale AI agents, from tools to expert guidance: https://g.co/startupagentguideTimestamps:04:32 — Why Creativity Dies When Life Feels Too Comfortable06:36 — The Loneliness That Sparked Creative Mornings07:49 — The Simple Idea That Built a 25,000+ Global Community09:10 — 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 Heal15:17 — 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 Ever25:15 — The Journey From Head to Heart35:17 — The Book That Changed How She Builds Community36:11 — The Hardest Lesson: You Can’t Escape Yourself37:04 — The Limiting Belief That Holds Most People Back41:02 — Redefining Success: Peace Over AchievementFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#communitybuilding #creativemornings #leadershipmindset #personaldevelopment #founderjourney #businessstrategy #networking #divotpodcast
- Apr 1, 20261h 8m
#43: Success Won’t Fix You (What a $4B CEO Learned Too Late)
Before leading a $4B company, Adam Edmunds spent years trying to prove he was good enough. From cold emailing CEOs as a student to building his first company, his journey started with uncertainty and a relentless need for validation.In this conversation with Derek Andersen, Adam shares how he became CEO of Entrata, a platform powering over 20,000 apartment communities worldwide, raising $700M+ and reaching a $4B+ valuation. He breaks down what it really takes to scale a company at that level.Adam explains why relationships are the most valuable currency in business, how great leaders recruit over years, not weeks, and why reputation determines the ceiling of your success. He also shares hard lessons on hiring, culture, and long-term thinking.The episode goes deeper into identity, failure, and self-worth, why success doesn’t fix how you feel about yourself, and how learning to stop seeking external validation changed everything about how he leads and lives.Follow Adam - X (Twitter): https://x.com/adamedmundsFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:Google for StartupsEverything you need to build and scale AI agents, from tools to expert guidance: g.co/startupagentguidePulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride: https://tinyurl.com/PulleyPartnerTimestamps:03:52 — The Power of Starting Before You’re Ready07:41 — Cold Emails That Changed His Life Forever12:58 — Building His First Company From Scratch18:36 — Inside a $4B Company (Entrata Breakdown)24:11 — How Great CEOs Think About Hiring Talent30:27 — Why Relationships Are the Ultimate Business Asset36:48 — Leadership, Culture, and Scaling Teams43:55 — The Hidden Cost of Success and Achievement50:12 — Why Success Doesn’t Fix Your Self-Worth56:34 — Redefining Identity Beyond Business1:01:22 — What Actually Matters at the EndFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#ceomindset #startupgrowth #scalingbusiness #founderjourney #leadershipskills #buildinginpublic #entrepreneurmindset #businessstrategy #personalgrowth #divotpodcast
- Mar 25, 20261h 1m
#42: How Crumbl Founder Built a $1B Cookie Empire From One Cookie
Before building Crumbl, Jason McGowan was a tech founder focused on virality, creating products used by over 120 million people. He then made a bold move: leaving tech to start a simple cookie business.In this conversation with Derek Andersen, Jason shares how Crumbl grew from one chocolate chip cookie into a $1B+ franchise with 1,000+ locations across the U.S. He explains how product-market fit, A/B testing, and viral growth turned a simple idea into a national brand.Jason breaks down why product matters more than marketing, how customer obsession drives growth, and how Crumbl built a viral experience through sharing, weekly drops, and community feedback.The episode also explores leadership, success, and why money doesn’t create lasting happiness. Jason reflects on family, purpose, and what truly matters after building a billion-dollar company.Follow Jason - X (Twitter): https://x.com/jasonmcgowanFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartnerTimestamps:04:32 — Building the Perfect Cookie With A/B Testing07:18 — The Bubblegum Cookie Failure (Hard Lesson)08:54 — The Simple Idea Behind Crumbl’s Viral Growth17:58 — Owning the Customer (Lessons from Facebook)20:03 — How Crumbl Accidentally Became a Franchise22:43 — Why Product Matters More Than Marketing26:18 — Reading Reddit as CEO (Customer Obsession)30:34 — Scaling Crumbl Nationwide34:16 — Weekly Drops: The Genius Behind the Menu44:48 — Money Doesn’t Buy Happiness (Real Talk)46:25 — Family, Purpose, and What Actually Matters54:53 — The Truth About Success and Fulfillment59:26 — Just Get Started (Final Advice)Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#NegotiationSkills #Stanford #BusinessNegotiation #Persuasion #Leadership #Startups #VentureCapital #Entrepreneurship #DealMaking #DivotPodcast
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About Divot
Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment.We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path.Stories of people making their mark, and how you can too.New episodes every Wednesday.#DivotPodcast #Business #Tech #Sports #Entertainment #Innovation
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It's a free AI-powered email that summarizes new episodes of Divot as soon as they're published. You get the key takeaways, notable quotes, and links & mentions — all in a quick read.
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