Divot

Derek Andersen

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

  1. #55: The Best Lessons From 50+ Divot Conversations | Special Recap

    9h ago

    #55: The Best Lessons From 50+ Divot Conversations | Special Recap

    After more than 50 episodes of Divot, Derek Andersen celebrates conversations that have inspired, educated, and reached millions. This special recap features Doug Leone, former Global Managing Partner at Sequoia Capital, the legendary venture firm behind Apple, Google, YouTube, Airbnb, WhatsApp, Stripe, and Nvidia; Justin Kan, the Twitch co-founder behind a nearly $1B Amazon exit; Charlie Rocket, the brain-tumor survivor who lost 120 pounds and became a Nike athlete; Marc Randolph, the Netflix co-founder and first CEO; and James Dumoulin, the School of Hard Knocks co-founder who built a 22M-follower media empire. You’ll also hear Guy Kawasaki, the former Apple evangelist and Canva chief evangelist; Tim Draper, the legendary venture capitalist known for Tesla, SpaceX, Skype, Hotmail, and Bitcoin; Liz Wiseman, the bestselling author of Multipliers and one of the top voices in leadership; Brandt Andersen, the Hollywood filmmaker and producer behind Lone Survivor, Everest, American Made, Silence, and I Was a Stranger; Tina Roth Eisenberg, the CreativeMornings founder who built a global movement around creativity; and Dave Bell, the creator behind Dave’s Auto Center and a voice for craftsmanship, faith, family, and legacy. In this special recap episode, Derek Andersen revisits the wisdom behind the journey: showing up before anyone is watching, taking risks before the outcome is clear, building through rejection, finding meaning beyond money, leading with humility, and keeping faith, values, family, and purpose at the center. These are the moments that capture the heart of Divot so far. Follow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:00:00 — The Wisdom Behind 50+ Divot Episodes01:05 — Celebrating More Than 50 Episodes of Divot02:18 — Doug Leone: The Discipline to Show Up03:52 — Justin Kan: Why Success Doesn’t Solve Everything06:02 — Charlie Rocket: The Winning Streak Mindset08:30 — James Dumoulin: When Rejection Becomes Fuel11:53 — Guy Kawasaki: Stop Trying to Be the Next Steve Jobs15:05 — Tim Draper: Ideas That Can Change the World17:57 — Liz Wiseman: How Great Leaders Actually Change20:50 — Marc Randolph: You’re Living the Good Old Days23:36 — Brandt Andersen: Why Hard Things Shape Us26:03 — Tina Roth Eisenberg: The Lost Art of Being Human28:08 — Dave Bell: Keep Your Feet Moving 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/divotdotorg Hashtags:#DivotPodcast #DerekAndersen #Entrepreneurship #Founders #Leadership #StartupLessons #WorldClassBuilders #BusinessWisdom #PurposeDriven #FaithAndFamily #VentureCapital #Creators

    31 min
  2. #54: The Human Data Engine Training Smarter AI Models | Micro1 CEO

    Jun 24

    #54: The Human Data Engine Training Smarter AI Models | Micro1 CEO

    Ali Ansari is the founder and CEO of Micro1, the human data engine helping AI labs train foundational models and enterprises build better AI agents. With more than 5M people screened, Micro1 provides expert data, frontier evaluations, reinforcement learning environments, and contextual agent evaluations for the next generation of AI systems. In this episode with Derek Andersen, Ali explains how large language models actually learn, why human judgment still drives AI progress, and why real-world company data may become one of the most valuable assets in the AI economy. He breaks down long-horizon tasks, compounding errors, post-training, AI agents, and the “infinite last mile” of intelligence. Ali also shares what it feels like to build at the center of the San Francisco AI boom, why AI will create new categories of high-value jobs, and how his journey from immigrating to the U.S. from Iran to building Micro1 shaped his founder mindset. This is a conversation about AI, human expertise, and embracing the chaos of a once-in-a-generation technology wave. Follow Ali - Instagram: https://x.com/aliansarinikFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:01:32 — Building Micro1 in the Center of the AI Boom06:57 — A Once-in-a-Lifetime AI Opportunity08:44 — How Micro1 Helps Train Smarter AI Models10:43 — Why AI Models Never Stop Learning14:56 — Why AI Still Needs Human Experts17:49 — The Model Is Not the Product21:23 — Who Wins and Loses in the AI Era27:25 — When AI Agents Become Team Members29:19 — The Talent War for AI Researchers33:38 — Why Your Company Data Is Training AI38:35 — From Iran to the American Dream44:33 — Why Taking a Unique Path Can Win48:04 — Embrace the Chaos49:50 — Why AI Will Create New Jobs53:02 — How Ali Measures His Life 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/divotdotorg Hashtags:#AI #ArtificialIntelligence #FutureOfWork #AIData #AIAgents #MachineLearning #Startups #DivotPodcast

    55 min
  3. #53 Part 2: Charlie Rocket on Manifesting Backwards, Winning Streaks & Making Impossible Dreams Real

    Jun 17

    #53 Part 2: Charlie Rocket on Manifesting Backwards, Winning Streaks & Making Impossible Dreams Real

    Charlie Rocket believes your dream may already be done; time just has not caught up yet. In Part 2 of this conversation, the Dream Machine Foundation founder explains how the things that light you up can become a signal, a direction, and a reason to move before the world gives you proof. In this episode with Derek Andersen, Charlie breaks down manifesting backwards, speaking the future before it exists, and building a winning streak in your mind. He shares why he walked away from a $15M business to chase becoming a Nike athlete, how writing things down makes the invisible feel real, and why words can shape the reality you move toward. The conversation goes deeper into dreams, miracles, faith, identity, and the courage to live inside possibility. Charlie shows that life can change faster than most people think when you stop waiting for certainty and start acting from the future you believe is already on the way. Follow Charlie - Instagram: https://www.instagram.com/charlieFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:01:32 — How to Find the Dream That Lights You Up05:06 — Why Charlie Walked Away From a $15M Business06:01 — How to Manifest Backwards11:37 — Speaking the Future Before It Exists15:53 — Charlie’s Nike Manifestation Story17:19 — Why Writing Things Down Makes Dreams Real19:28 — How to Start Seeing Miracles22:23 — Derek’s Scotty Cameron Miracle Story27:15 — You Weren’t Derailed, You Were Delivered28:11 — The Pain That Built Charlie’s Success36:25 — The Winning Streak That Changed His Life37:35 — How to Overcome Hard Things38:57 — Measuring Life in Possibilities39:53 — What Charlie Hopes God Says 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/divotdotorg Hashtags:#charlierocket #delusionaloptimism #manifestingbackwards #winningstreak #impossibledreams #dreammachine #manifestation #mindset #personalgrowth #reinvention #miracles #purpose #possibility #entrepreneurship #divotpodcast

    40 min
  4. #53: Brain Tumor, Losing 120 Pounds & Becoming a Nike Athlete: Charlie’s Delusional Optimism Formula

    Jun 10

    #53: Brain Tumor, Losing 120 Pounds & Becoming a Nike Athlete: Charlie’s Delusional Optimism Formula

    Charlie Rocket helped create major cultural moments in hip hop, working with artists like 2 Chainz, contributing to Grammy-winning campaigns, winning an Emmy, and managing some of the biggest names in music. But after facing obesity, depression, burnout, and a brain tumor, Charlie reinvented everything: he lost 120 pounds, became a Nike athlete, ran across America, and turned Dream Machine Foundation into a global movement for impossible dreams. In this episode with Derek Andersen, Charlie breaks down his Delusional Optimism Formula: how to turn pain into proof, proof into belief, and belief into action. He explains why the key to changing your life is building a winning streak in your mind, collecting constant proof that you are winning, and training yourself to see setbacks, rejection, and failure as signs that life is still working for you. The conversation goes deeper into reinvention, identity, manifestation, gratitude, viral content, and the courage to believe your life can change faster than you think. Charlie shows that impossible dreams are not built by avoiding pain. They are built by turning every loss into momentum, every setback into a lesson, and every small win into proof that your dream is already on the way. Follow Charlie - Instagram: https://www.instagram.com/charlieFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:00:00 — Charlie Rocket’s Delusional Optimism Formula00:36 — From Hip Hop Success to a Life-Changing Brain Tumor00:56 — Losing 120 Pounds and Becoming a Nike Athlete05:08 — Why You Are Undefeated09:28 — Turning Every Loss Into a Win12:37 — What Delusional Optimism Really Means17:33 — Proof Creates Delusion, Delusion Creates Action30:02 — How to Become a Delusional Optimist34:59 — How to Reinvent Yourself35:33 — Kobe Bryant, Black Mamba, and the Alter Ego Effect40:57 — Charlie’s Viral Content System42:16 — 20M Views and 200K Followers in 45 Days44:43 — How to Build a Winning Streak Every Morning57:48 — How Fast Your Life Can Change 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/divotdotorg Hashtags:#charlierocket #delusionaloptimism #nikeathlete #dreammachine #reinvention #mindset #manifestation #winningstreak #personalgrowth #impossibledreams #brainTumorSurvivor #entrepreneurship #founderjourney #motivation #divotpodcast

    1h 1m
  5. #52: He Built a 22M Media Empire by Interviewing Tom Cruise, Shaq, Brady & 52 Billionaires

    Jun 3

    #52: He Built a 22M Media Empire by Interviewing Tom Cruise, Shaq, Brady & 52 Billionaires

    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/realjamesdumoulinFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:01:48 — How School of Hard Knocks Started03:56 — 400 Posts With Only 50 Followers04:41 — From $100K Months to $1M Months06:15 — How Small Teams Can Win With Content09:24 — The Only Metric That Matters Online10:20 — Why the First 3 Seconds Decide Everything13:03 — How Travel Shaped James’ Ambition14:25 — Turning Rejection Into Fuel15:41 — Interviewing 52 Billionaires by 2315:52 — How James Got Mark Cuban17:30 — Tom Cruise, Brady, Shaq, and Bigger Asks20:08 — Why Business Takes Courage20:50 — Building One of the Biggest Business Media Networks 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/divotdotorg Hashtags:#jamesdumoulin #schoolofhardknocks #contentcreation #goingviral #watchtime #entrepreneurship #businessmedia #founderjourney #creatoreconomy #divotpodcast

    23 min
  6. #51: Justin Kan on Success, Happiness & Why Achievement Never Feels Enough | Twitch Founder

    May 28

    #51: Justin Kan on Success, Happiness & Why Achievement Never Feels Enough | Twitch Founder

    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/justinkanFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps:01:40 — Justin Kan’s Tattoo About Gratitude02:46 — Why Success Still Creates Comparison03:36 — Why Money and Fame Don’t Create Happiness06:55 — Why Achievement Only Feels Good for a Moment10:51 — The Habit That Rewired Justin’s Brain16:39 — AI, Mental Health, and Social Media18:10 — Why Justin Isn’t Chasing the AI Gold Rush21:49 — The Founder Trait Justin Looks For Most23:19 — Why Justin Invested $8 Million After a Cold Plunge26:20 — Why You Shouldn’t Chase the AI Crowd26:44 — The Next Big Frontier After AI 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/divotdotorg Hashtags:#justinkan #twitch #siliconvalley #entrepreneurship #startupfounder #mentalhealth #successmindset #founderjourney #personalgrowth #divotpodcast

    28 min
  7. #50: Claude, AI Agents & the End of Traditional SaaS | Navin Chaddha

    May 20

    #50: Claude, AI Agents & the End of Traditional SaaS | Navin Chaddha

    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

    28 min
  8. #49: Success, Loneliness, Ambition & Why High Performers Never Feel Enough | David Spinks

    May 13

    #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/derekjandersen Episode Partners:Google for StartupsGrab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia Timestamps: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 Dangerous 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/divotdotorg Hashtags:#successmindset #highachievers #selfworth #ambition #loneliness #mentalhealth #personalgrowth #burnout #foundermindset #divotpodcast

    49 min
See All (57)

5
out of 5
23 Ratings

About

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

Information

  • Creator
    Derek Andersen
  • Years Active
    2025 - 2026
  • Episodes
    57
  • Rating
    Clean
  • Copyright
    © Derek Andersen
  • Show Website
    Divot

You Might Also Like