Divot

Greg Isenberg is the entrepreneur and AI strategist behind Late Checkout, a portfolio of AI-native businesses powered by agents and online communities. He founded FiveBuy, acquired by StumbleUpon, and built Islands, acquired by WeWork. Through Idea Browser, Greg's Letter, and the Startup Ideas Podcast, Greg has shared over 2,000 startup ideas with millions of followers and advised the world's largest brands on AI strategy.
In this episode with Derek Andersen, Greg explains why AI is only as good as the context you feed it, how to find validated startup ideas through trend data rather than intuition, and why the age of the multi-preneur has arrived. He breaks down his ACP framework, the builder-distributor advantage, and how to build a business from scratch in 90 days.
The conversation goes deeper into what it truly means to become AI-native, why 1,000 hours of practice separates those who win from those who don't, and the formative baseball rejection that taught Greg the hardest truth: not everything is in your control. Greg shows that when the gatekeepers are gone, creativity and distribution become the last real competitive advantage.
Follow Greg - X (Twitter): https://x.com/gregisenberg
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Google for Startups
If you’re building applications with generative media or considering it, Google just released brand-new technical guide. You can download it at https://goo.gle/genmediaguide
Timestamps:
00:01:52 — The $2/Hour AI Co-Founder
00:03:21 — How to Find the Right Startup Idea
00:07:38 — Why Your AI Keeps Giving You Bad Results
00:11:26 — What AI Will Replace in the Next 18 Months
00:14:46 — Why Creatives Win the Age of AI
00:18:45 — The Age of the Multi-Preneur
00:24:56 — The Builder-Distributor Advantage
00:26:32 — How to Run a Startup on Autopilot
00:30:30 — 3 Hours vs. 6 Months: What AI Changed
00:33:06 — Why AI Just Killed the Startup Gatekeepers
00:41:32 — The 1,000-Hour Rule to Master AI
00:43:34 — Build a Business in 90 Days: The ACP Framework
00:47:00 — The Rejection That Changed Everything
00:55:12 — "He Helped Me" — On Legacy and Purpose
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:
#GregIsenberg #LateCheckout #MultiPreneur #AIStartup #AICoFounder #StartupIdeas #AIPodcast #Entrepreneurship #BuilderDistributor #VibeCode #StartupStrategy #BoringBusiness #AIAge #DivotPodcast

Nick O’Neill is the entrepreneur, software developer, and creator behind Choose Rich, the provocative online character that transformed crypto commentary, luxury satire, and internet outrage into a media business generating millions of dollars a year. After one yacht post exploded to more than 45 million impressions, Nick discovered how attention spreads, how perception shapes reality, and how to build a business around internet culture.
In this episode with Derek Andersen, Nick opens up about his Hodgkin lymphoma diagnosis after nearly two years of unexplained symptoms, the mindset helping him face chemotherapy, and why he believes, “I’m basically a statistic.” He also shares how he intentionally turned internet hate into viral growth, what most creators misunderstand about attention, and why optimism is ultimately a choice.
The conversation goes deeper into selling Bitcoin and Ethereum too early, engineering viral marketing stunts, overcoming panic attacks, separating real blockchain innovation from crypto speculation, and building a media company that generates millions. Nick shows that resilience is not pretending life is easy; it is choosing what defines you, making people smile, and making the most of every single day.
Follow Nick - X (Twitter): https://x.com/chooserich
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Google for Startups
If you’re building applications with generative media or considering it, Google just released brand-new technical guide. You can download it at https://goo.gle/genmediaguide
Timestamps:
01:43 - Nick Opens Up About His Cancer Diagnosis
07:41 - “I’m Basically a Statistic”
14:11 - What It Means to Say, “I Ran a Good Race”
16:06 - How Choose Rich Became a Viral Business
18:27 - The Yacht Post That Reached 45 Million People
21:27 - The Viral Yacht Stunt That Fooled the Internet
26:12 - Selling Ethereum at $11 and Bitcoin at $150
32:26 - Why Crypto Adoption Is Happening Quietly
44:24 - The Failure That Sent Nick to the Hospital
48:45 - Why Cancer Did Not Define Him
59:21 - How Nick Measures a Successful 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:
#NickONeill #ChooseRich #CancerJourney #HodgkinLymphoma #Chemotherapy #Optimism #Resilience #Entrepreneurship #GoingViral #ViralMarketing #ContentCreator #CreatorEconomy #Crypto #Bitcoin #DivotPodcast

Ed Catmull co-founded Pixar and helped build the creative engine behind some of the most beloved films of the last 30 years, including Toy Story, Finding Nemo, The Incredibles, Ratatouille, WALL-E, and Up. Long before Pixar changed animation forever, Ed helped pioneer 3D computer graphics, build RenderMan, and partner with Steve Jobs and John Lasseter to create one of the most influential creative companies in history.
In this episode with Derek Andersen, Ed reveals how Pixar really became Pixar: the 14-year path to making Toy Story possible, why Steve Jobs stayed out of the Braintrust, how Pixar protected creative honesty, and why getting the team right matters more than getting the idea right. He also shares lessons from Creativity Inc. on long-term thinking, failure, leadership, disagreement, and building a culture where the best ideas can survive.
The conversation goes deeper into the stories behind Pixar’s success, from almost losing Toy Story 2 to choosing hard films like Ratatouille and Up when they did not look commercially obvious. Ed shows that Pixar’s real secret was not one perfect idea, one genius leader, or one lucky movie. It was a culture strong enough to turn impossible ideas into stories the world never forgets.
Follow Ed - X (Twitter): https://x.com/edcatmull
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:
01:39 - Why Great Companies Fail to Think Long-Term
07:35 - Why VR, Oculus, and Tech Hype Got Ahead of Reality
19:13 - The 14-Year Math Behind Toy Story
24:57 - Why the Right Environment Creates Pioneers
37:34 - Why Steve Jobs Let Pixar Publish Everything
42:26 - Steve Jobs’ $54M Bet on Pixar
44:53 - Why Great Teams Create Great Ideas
54:20 - Why Pixar Did Not Call Every Mistake a Failure
59:08 - Why Steve Jobs Stayed Out of Pixar’s Braintrust
01:03:06 - Why Powerful Leaders Should Speak Last
01:15:03 - How Pixar Made Steve Jobs a Billionaire
01:21:15 - The Steve Jobs Transformation Most People Missed
01:24:17 - Why Ed Catmull Believes He Is Wrong Half the Time
01:33:10 - Ed Catmull Was Removed as Pixar President Twice
01:37:27 - Why Creativity Inc. Was Really About Building Great Teams
01:42:26 - How Pixar Almost Lost Toy Story 2
01:46:36 - How Pixar Became a Repeatable Creative Studio
01:47:19 - Why Ratatouille and Up Should Not Have Worked
01:49:13 - How Ed Catmull 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:
#pixar #stevejobs #edcatmull #toystory #creativityinc #pixarbraintrust #findingnemo #theincredibles #ratatouille #walle #up #creativeleadership #storytelling #innovation #divotpodcast

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 Startups
Grab the new Google for Startups Future of AI report at https://goo.gle/futureofgenmedia
Timestamps:
00:00 — The Wisdom Behind 50+ Divot Episodes
01:05 — Celebrating More Than 50 Episodes of Divot
02:18 — Doug Leone: The Discipline to Show Up
03:52 — Justin Kan: Why Success Doesn’t Solve Everything
06:02 — Charlie Rocket: The Winning Streak Mindset
08:30 — James Dumoulin: When Rejection Becomes Fuel
11:53 — Guy Kawasaki: Stop Trying to Be the Next Steve Jobs
15:05 — Tim Draper: Ideas That Can Change the World
17:57 — Liz Wiseman: How Great Leaders Actually Change
20:50 — Marc Randolph: You’re Living the Good Old Days
23:36 — Brandt Andersen: Why Hard Things Shape Us
26:03 — Tina Roth Eisenberg: The Lost Art of Being Human
28:08 — Dave Bell: Keep Your Feet Moving
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:
#DivotPodcast #DerekAndersen #Entrepreneurship #Founders #Leadership #StartupLessons #WorldClassBuilders #BusinessWisdom #PurposeDriven #FaithAndFamily #VentureCapital #Creators

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/aliansarinik
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:
01:32 — Building Micro1 in the Center of the AI Boom
06:57 — A Once-in-a-Lifetime AI Opportunity
08:44 — How Micro1 Helps Train Smarter AI Models
10:43 — Why AI Models Never Stop Learning
14:56 — Why AI Still Needs Human Experts
17:49 — The Model Is Not the Product
21:23 — Who Wins and Loses in the AI Era
27:25 — When AI Agents Become Team Members
29:19 — The Talent War for AI Researchers
33:38 — Why Your Company Data Is Training AI
38:35 — From Iran to the American Dream
44:33 — Why Taking a Unique Path Can Win
48:04 — Embrace the Chaos
49:50 — Why AI Will Create New Jobs
53:02 — How Ali Measures His 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:
#AI #ArtificialIntelligence #FutureOfWork #AIData #AIAgents #MachineLearning #Startups #DivotPodcast