Divot

Before becoming one of the most influential evangelists in the history of technology, Guy Kawasaki was part of Apple’s original Macintosh team, working directly with Steve Jobs during the early days of personal computing. His career has been defined by independent thinking, deep curiosity, and a lifelong commitment to building and evangelizing products that truly matter.In this conversation, Guy reflects on working with Steve Jobs, the difference between mission-driven and ego-driven leadership, and why the best products are built by people solving problems for themselves. He shares hard-earned lessons from Silicon Valley on creativity, obsession, grit, and what it really takes to build things that last.Guy also discusses his role as Chief Evangelist of Canva, the global design platform democratizing creativity for millions worldwide, and how recognizing great products early shaped his journey. From writing 18 books to advising startups and founders, he explains why authenticity consistently outperforms imitation in entrepreneurship and product building.The episode goes deeper into purpose and legacy, exploring learning later in life, embracing setbacks, redefining success, and measuring impact not by status or money, but by one simple idea: empowering people.Follow Guy - Instagram: https://www.instagram.com/guykawasakiFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divotPulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartnerTimestamps:1:09 — Starting Surfing at 60: Obsession Beats Talent3:49 — Growing Up in Hawaii: Identity, Culture & Perspective6:44 — Everybody Has Something to Hide: Privacy, Signal & Freedom12:44 — Writing 18 Books: Why Most People Shouldn’t Write One16:57 — Build for Yourself: The Origin of Great Products18:20 — Working With Steve Jobs: Mission Over Ego19:40 — Mission-Driven vs Ego-Driven Leadership22:35 — The Halo Effect: Why You Should Be Skeptical of Authority27:22 — Steve Jobs vs Elon Musk: Focus vs Scale30:51 — Don’t Be the Next Steve Jobs. Be the First You33:08 — Finding Your Calling: Loving the Entire “Sandwich”46:31 — Jane Goodall: Purpose Without Retirement52:19 — Guy’s Golden Touch: Finding Gold Early57:24 — Grit as the Real Advantage58:25 — Family, Legacy & Measuring a 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:#GuyKawasaki #SteveJobs #ElonMusk #Apple #Canva #Entrepreneurship #Startups #Creativity #ProductBuilding #Leadership #Innovation #SiliconValley #Grit #Purpose #DivotPodcast

Before becoming one of the most respected surfboard shapers in the world, Bob Pearson built his craft through obsession, experimentation, and more than six decades of hands-on learning. Since shaping his first board in 1964, Bob has remained committed to one belief: mastery is never finished.Over his career, Bob has shaped more than 100,000 surfboards, becoming a defining force in modern surfboard design and big wave surfing. From his factory in Santa Cruz, California, he has worked closely with legendary surfers including Laird Hamilton, Jay Moriarty, Jamie Mitchell, and others who pushed the limits at waves like Mavericks, Jaws, Waimea, Sunset, and Nazaré. His boards were featured throughout the film Chasing Mavericks, shaping the equipment ridden in the movie.The episode also explores Bob’s friendship with Jay Moriarty, the mindset required for big wave surfing, and the deeper meaning of surfing beyond performance, connection, community, mental health, and joy. At 77 years old, Bob still works nearly every day, driven by curiosity, gratitude, and a lifelong passion for the ocean.Follow Bob - Instagram: https://www.instagram.com/pearsonarrowFollow Derek - X (Twitter): https://twitter.com/derekjandersenEpisode Partners:DelveDelve uses AI agents to handle SOC 2, ISO 27001, GDPR, and more - Divot listeners get $1,500 credits to get started: https://delve.co/deals/divotPulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartnerTimestamps:1:27 — Working 7 Days a Week2:08 — Shaping 100,000+ Boards4:54 — Surfboard Design Is Logic5:38 — Every Board Has Tradeoffs6:07 — 100+ Ways to Shape a Board7:07 — From 5ft Boards to Big Wave Guns7:19 — Why Top Surfers Work With Bob9:47 — Collaboration Beats Guesswork11:54 — When Mastery Actually Begins16:04 — Finding Mavericks Before the Hype18:14 — Chasing Mavericks & Meeting Jay25:18 — The Iconic Wipeout Explained29:56 — Injury, Fear & Healing in the Ocean38:07 — Bells Beach & Teaching in Australia40:26 — Surviving Sharks in Big Surf43:58 — Bali Before Surf Tourism48:20 — How to Handle Conflict in the Water55:05 — One Idea for the World1:01:40 — The Mark Bob Wants to LeaveFollow 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:#BobPearson #SurfboardShaping #BigWaveSurfing #Mavericks #ChasingMavericks #SurfingLegends #LairdHamilton #JayMoriarty #SurfDesign #SurfCulture #OceanLife #MentalHealth #Craftsmanship #Mastery #DivotPodcast

Tim Draper, a pioneering venture capitalist and founder of Draper Associates, dives into his journey backing groundbreaking companies like Tesla and SpaceX. He shares insights on the evolution of Bitcoin, emphasizing its potential as a transformative technology that aids the unbanked. Draper discusses the importance of independent thinking in entrepreneurship and reflects on the ups and downs of tech cycles. With a mission to reshape education and governance in California, he inspires others to forge their paths and embrace challenges.

In this episode of Divot, we sit down with Aparna Chennapragada, Chief Product Officer for AI at Microsoft, to explore how artificial intelligence is reshaping the way products are built, teams collaborate, and companies scale in an increasingly automated world.Aparna has spent her career at the intersection of technology and human behavior, from leading product at Google and YouTube to shaping Microsoft’s AI strategy today. In this conversation, she shares how the rapid acceleration of AI is compressing years of innovation into months, forcing leaders to rethink how they build, experiment, and make decisions.We discuss what it means to design AI-native products, why traditional development cycles no longer apply, and how the best teams are adapting to constant change. Aparna also reflects on leadership in an era of uncertainty, the importance of curiosity over certainty, and what it takes to build systems that genuinely help people work better.This episode offers a thoughtful look at the future of work, product development, and the mindset required to build responsibly in an AI-driven world.Follow Aparna - X (Twitter): https://x.com/aparnacdFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:01:44 – “This Time Is Different”: Why AI Adoption Is Unprecedented02:13 – The Brick Phone Story: How Slow Adoption Used to Be03:32 – The “Scanned Brochure” Moment: Early Web vs Early AI04:27 – AI Agents at Work: Prompts as the New PRDs05:37 – Designers Are Unlocked: Building End-to-End With AI Tools06:26 – The “Barbell Team”: Model Whisperers + Product Builders07:31 – How Aparna Stays Ahead: Build Things (No Shortcuts)09:55 – Thin Steps vs Fat Steps: What Got Easy, What Became the Bottleneck11:17 – Making AI a “Contact Sport”: Building Reflexive AI Habits14:33 – Why Startups Win Next: Rethinking Workflows Beats “Just Add AI”15:54 – The Data Flywheel Problem: Designing for “Learnability”17:16 – The Next Phase: Products That Improve via UI Reward Signals17:45 – Small Teams That Ship: Why ~10 People Can Build Fast Now18:42 – Startup Opportunities: Rewriting the Web for AgentsFollow 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:#DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork

Josh Reeves, co-founder and CEO of Gusto, shares how he built one of the most trusted platforms for small businesses, and what it truly takes to scale a company with purpose.In this episode, Josh breaks down the realities of building and leading a high-growth startup, navigating regulation, designing products for long-term impact, and maintaining culture as teams and responsibilities scale. He explains how focusing on customers, discipline, and long-term thinking has shaped Gusto’s journey and why sustainable growth matters more than chasing short-term wins.This conversation is a deep dive into founder mindset, leadership, and building enduring companies, essential listening for entrepreneurs, operators, and anyone serious about building something that lasts.Follow Josh - X (Twitter): https://x.com/joshuareevesFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:01:44 – Why Most Startups Fail Before They Even Begin02:27 – The Hidden Cost of Regulation03:48 – Why Payroll and Benefits Matter More Than You Think05:39 – The Real Reason Running a Business Feels So Hard07:44 – The Benefit That Completely Changed Employee Loyalty09:31 – What Sustainable Growth Actually Looks Like11:34 – The Three Metrics That Truly Matter in Business13:58 – Why Chasing Hypergrowth Can Destroy Great Companies15:48 – Building a Company Meant to Last for Decades17:20 – The Leadership Mindset That Separates Great Founders18:54 – Why Being “Busy” Is Not the Same as Making Progress20:21 – How to Identify People Who Will Actually Succeed22:46 – How AI Is Changing the Way Teams Work24:06 – Why Helping Others Is the Ultimate Advantage25:32 – The Life Lessons That Shape Great Leaders27:20 – Gratitude, Perspective, and Staying Grounded29:33 – What Success Really Means (And What It Doesn’t)31:43 – The One Principle That Guides Every Decision33:22 – A Simple Philosophy for a Meaningful 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:#DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork

Before he became an award-winning filmmaker and humanitarian, Brandt Andersen built a tech company from scratch, scaled it to tens of millions in revenue, and sold it before moving into filmmaking, where he went on to produce major films like Everest, Lone Survivor, and American Made. But behind the success is a life shaped by extremes: a skydiving accident that nearly killed him, surviving the Malibu fires with his son, and years spent inside war zones helping people in crisis.In this conversation, Brandt shares the real stories behind I Was a Stranger, his new film inspired by the Syrian refugee crisis. He explains how meeting smugglers, soldiers, parents, and children across Syria, Turkey, Jordan, and Haiti reshaped his understanding of judgment, fear, and humanity.This episode is also deeply personal. Brandt is Derek's older brother. Together, they revisit the moments that forged their bond: childhood chaos, life-or-death situations, and the lessons Brandt passed down through the way he lives. Their conversation reveals the heart, flaws, courage, and philosophy of a man who has spent his life running toward the fire for others, and the profound impact that has had on Derek.Learn More About Brandt - Wikipedia: https://en.wikipedia.org/wiki/Brandt_AndersenFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:1:39 — Who Brandt Andersen Really Is & Why His Story Matters3:03 — The Skydive That Should Have Killed Him8:47 — What Facing Death Taught Brandt About Life14:02 — The Wild Childhood Stories That Shaped Him18:10 — The Banksy Above His Fireplace & His Dark/Light Identity22:30 — From Startup Exit to Hollywood Storytelling28:41 — Producing Everest, Lone Survivor & American Made32:12 — The Real Families Who Inspired I Was a Stranger36:55 — Inside Syria: Crisis Through Human Eyes41:38 — “Don't Judge People by Their Worst Day”45:52 — Haiti Earthquake: Chaos, Hunger & Purpose52:10 — The Moment That Changed His View of Humanity1:12:03 — Trapped in the Malibu Fires With His Son1:29:45 — What Brandt Ultimately Wants People to UnderstandFollow 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:#BrandtAndersen #IWasAStranger #Filmmaking #Storytelling #SyrianRefugeeCrisis #HumanitarianAid #WarZones #Resilience #Courage #PurposeDrivenLife #LoneSurvivor #Everest #AmericanMade #Leadership #PersonalGrowth #DivotPodcast

Before he became chairman of the Napoleon Hill Institute, David Meltzer lived a life driven by scarcity, ambition, and the need to prove himself. Raised by a single mother in Akron, he chased success to change their future, eventually becoming a multimillionaire and CEO in the sports world. But behind the achievements was an identity built on ego, bad habits, and external validation, leading to the breaking point that forced him to confront who he’d become.In this conversation, David shares the mindset shift that saved his marriage, the four values that rebuilt his identity, and how losing over $100M became the foundation for a healthier, more purposeful life. He explains how faith, gratitude, sleep discipline, and time mastery helped him recover, along with the frameworks he teaches today to serve his mission of empowering over a billion people. From stop-drop-and-roll to emotional chemistry and using failure as fuel, David breaks down the tools that rebuilt his life from the inside out.A vulnerable and practical look at reinvention, this episode reveals what it truly takes to grow through loss and rebuild meaning. If you’re navigating change, recovering from setbacks, or redefining success, David’s story offers perspective, resilience, and a blueprint for living with intention.Follow David - X (Twitter): https://x.com/davidmeltzerFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 — David’s Life: The Fall That Saved Him2:21 — Akron Roots: Scarcity, Survival & a Single Mom Who Never Quit4:58 — The Dream Life That Almost Destroyed Him7:06 — His Wife’s Warning: The Sentence That Changed Everything8:44 — Rebuilding the Man: The Four Values That Brought Him Back10:51 — Losing $100M: The Collapse He Was Finally Prepared For13:02 — The Habits That Saved His Marriage, Mind & Future17:47 — Failing Faster: Why Losing Is the Only Way to Win22:06 — Emotional Alchemy: Training His Reactions Every Single Day29:32 — “Stop, Drop & Roll”: The Method That Resets His Entire Life34:39 — Ego, Pain & Perspective: Understanding the Chemistry of a Breakdown42:18 — Turning Trauma Into Purpose: How He Rewrote His Story53:17 — The One Lesson He Wants to Leave Humanity55:38 — “What I Hope God Says to Me When I Arrive”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:#DavidMeltzer #Reinvention #Resilience #Mindset #LifeLessons #PersonalGrowth #SelfImprovement #OvercomingFailure #EmotionalIntelligence #SpiritualGrowth #Leadership #DivotPodcast

Before becoming the photographer trusted by the world’s biggest icons, Squint built his path on discipline, creativity, and a lifelong commitment to mastering storytelling. Raised in Palo Alto and shaped by years inside a TV studio before he turned 18, he grew from a kid with a camera into a filmmaker and cinematographer behind iconic portraits of Nas, Michael B. Jordan, Dave Chappelle, Draymond Green, and Steph Curry. As co-creator of the New York Times bestselling book Shot Ready, his black-and-white, emotionally driven style reflects a belief that great photography comes from patience, intention, and truly seeing people.In this conversation, he breaks down the ingredients of a powerful photograph, motion, eyes, framing, intimacy, and explains why rejection became his greatest superpower. He shares how he wrote a list of dream subjects at age 12 and photographed every name on it, how fatherhood reshaped his purpose, and why staying in the Bay Area defined his career more than any move to LA or New York. Squint reflects on rediscovering black-and-white photography after losing his father and earning Steph Curry’s trust through consistency, humility, and discipline.A grounded masterclass in photography, vision, resilience, and legacy, showing what it takes to create work that endures. This episode is a reminder that great art is built on love, discipline, and showing up, especially when the world tells you no.Follow Squint - Instagram: https://www.instagram.com/iamsquintFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 Introduction & how Squint became a visual storyteller3:48 First camera at age five5:17 Running a TV studio at eight6:44 Deciding at ten to do this forever8:09 The list he wrote at age 129:46 Shooting Nas for the first time12:12 How he processes rejection13:46 The Killers story16:30 Identity vs his work18:47 What makes a great picture20:31 Reading emotion through the eyes22:37 Atmosphere vs the subject26:13 Black and white vs color28:41 Training his eye32:59 Mastering relationships in the industry35:32 Showing people how he sees them48:53 Steph Curry’s discipline & ego50:20 Losing his father & rebuilding56:01 What makes a great dadFollow 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:#PhotographyMasterclass #VisualStorytelling #BlackAndWhitePhotography #CinematicPortraits #ShotReady #StephCurry #CreativeDiscipline #IconicImages #ArtOfSeeing #LegacyAndPurpose #CreatorsJourney

Before helping elevate the rise of global entrepreneurship, Christine Tsai, CEO & Founding Partner of 500 Global, built her path on curiosity, consistency, and an instinct for spotting potential early. From her beginnings in tech to guiding an investing platform that now reaches founders across dozens of countries, her journey reflects a belief that great companies can start anywhere, and that humility, resilience, and long-term thinking still define the world's strongest leaders.In this conversation, she breaks down the traits she's seen across exceptional founders, the realities of building companies through cycles, and how early-stage investing has evolved over the last decade. She shares lessons on ownership, clarity, adaptability, and speed, and why the most enduring teams evolve faster than the markets around them. Christine reflects on backing thousands of founders worldwide, what she looks for in leaders under pressure, and how a global perspective shapes better decisions and more intentional company building.A grounded masterclass in global insight, founder psychology, and building with purpose, offering a rare perspective on what it takes to scale, endure, and create lasting impact in a rapidly shifting world.Follow Christine - X (Twitter): https://x.com/christine_tsaiFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 — Early Curiosity, Identity & Finding Her Path3:12 — Lessons From Google & YouTube's Early Days6:58 — The Decision to Build a Global Investing Platform10:45 — Launching 500 & the Chaos of the First Years14:40 — How Early-Stage Investing Changed Over a Decade18:26 — The Traits She Sees in Exceptional Founders22:51 — Speed, Humility & the Signals That Truly Matter26:33 — Surviving Cycles & Leading Through Volatility30:55 — What Backing 3,000+ Founders Teaches You35:18 — Global Perspective: Why Innovation Comes From Everywhere39:07 — Leadership Moments That Define a CEO43:50 — Legacy, Purpose & Why Relationships Are the Real ScorecardFollow 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:#GlobalFounders #VentureCapital #StartupLeadership #EarlyStageInvesting #FounderMindset #ScalingStartups #GlobalInnovation #WomenInVC #LeadershipLessons #BuildingEnduringCompanies #Entrepreneurship #500Global

Mike Maughan, an executive with Smith Entertainment Group and co-founder of Five for the Fight, dives into the essence of impactful leadership. He discusses his transformative work on Salt Lake City's urban core, emphasizing the importance of community in billion-dollar projects. Maughan shares insights on the growing value of in-person connections amidst AI's rise, and the necessity of integrity and collaboration in leadership. He argues against chasing passion, instead advocating for solving meaningful problems, and highlights the importance of humility in leadership.