Astro Teller is the entrepreneur, AI scientist, and Captain of Moonshots who has led X, Alphabet’s moonshot factory, for more than 15 years. Under his leadership, X helped incubate Google Brain, Waymo, Wing, and Verily, breakthroughs spanning artificial intelligence, autonomous driving, drone delivery, and precision health. In 2026, Waymo alone raised $16 billion at a $126 billion valuation.

Zachery Dereniowski, better known as MDMotivator, left medical school after the pandemic, a devastating breakup, a torn ACL, and crushing isolation pushed him to the lowest point of his life. Today, his videos about kindness, mental health, and human connection reach more than 50 million followers, have generated over 40 billion impressions, and helped raise more than $5 million for strangers.

Eric Ries created the Lean Startup methodology and wrote "The Lean Startup," a New York Times bestseller that has sold more than a million copies in over 30 languages, teaching a generation of founders the MVP and build, measure, learn. He later founded the Long Term Stock Exchange, an SEC-approved exchange that has raised over $170 million, and just published his newest bestseller, "Incorruptible."

Blaine Anderson is the Shark Tank dating coach for men who built Dating by Blaine from a COVID-forced career pivot into a company with 7,000 clients and over 1 million followers. She accepted Mark Cuban's $100,000 offer on stage and became the first credible female voice on social media telling men the truth about what is actually going wrong in their dating lives.

Daniel Kottke met Steve Jobs at Reed College in 1972, traveled with him to India, and spent the summer of 1976 hand-assembling the very first Apple computers in the Jobs family garage in Cupertino, for $3 an hour. He was among Apple's earliest employees, hand-wired the Macintosh prototypes, and left his signature cast inside every original Mac ever made. Apple is now worth $5 trillion.

Grant Cardone grew up in the bayous of Louisiana with no money, no connections, and no plan, and spent a decade battling drug addiction before rebuilding from scratch. Today, his privately held companies generate $750 million in gross annual revenue, Cardone Capital manages more than 15,000 apartment units, and the 10X brand has shaped how millions of founders think about ambition and scale.

Mark Manson is a three-time NYT number one bestselling author whose book "The Subtle Art of Not Giving a F*ck" has sold more than 20 million copies across 65 languages, hitting number one in 14 countries. He co-wrote Will Smith's memoir and recently co-founded Purpose, an AI mental health startup that hit seven-figure revenue in 12 days.

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.

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.

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 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.

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.

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.

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.

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.

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.

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.

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.

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.

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.