Divot

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/pearsonarrow
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Episode Partners:
Delve
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Timestamps:
1:27 — Working 7 Days a Week
2:08 — Shaping 100,000+ Boards
4:54 — Surfboard Design Is Logic
5:38 — Every Board Has Tradeoffs
6:07 — 100+ Ways to Shape a Board
7:07 — From 5ft Boards to Big Wave Guns
7:19 — Why Top Surfers Work With Bob
9:47 — Collaboration Beats Guesswork
11:54 — When Mastery Actually Begins
16:04 — Finding Mavericks Before the Hype
18:14 — Chasing Mavericks & Meeting Jay
25:18 — The Iconic Wipeout Explained
29:56 — Injury, Fear & Healing in the Ocean
38:07 — Bells Beach & Teaching in Australia
40:26 — Surviving Sharks in Big Surf
43:58 — Bali Before Surf Tourism
48:20 — How to Handle Conflict in the Water
55:05 — One Idea for the World
1:01:40 — The Mark Bob Wants to Leave

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Hashtags:
#BobPearson #SurfboardShaping #BigWaveSurfing #Mavericks #ChasingMavericks #SurfingLegends #LairdHamilton #JayMoriarty #SurfDesign #SurfCulture #OceanLife #MentalHealth #Craftsmanship #Mastery #DivotPodcast

Before becoming one of the most influential venture capitalists in Silicon Valley, Tim Draper built a career defined by early conviction, independent thinking, and a willingness to back ideas long before they reached mainstream belief. Over decades, Tim has invested in and supported some of the most transformational companies of the modern era, shaping how the world communicates, moves money, explores space, and builds technology.

In this conversation, Tim reflects on backing category-defining companies, including Tesla, SpaceX, Skype, Hotmail, Twitch, and Robinhood, investments that went on to create hundreds of billions of dollars in enterprise value and permanently change global industries. He also shares the impact of Draper University, where thousands of founders have been trained, leading to thousands of companies launched and multiple billion-dollar outcomes.

The episode dives deep into Bitcoin and economic freedom, tracing Tim’s early belief in decentralized systems, his experience buying Bitcoin as early as 2011, and why he views it not as a trade but as a long-term technological shift with global implications, especially in a world of inflation, fragile banking systems, and unstable currencies.

Follow Tim - X (Twitter): https://x.com/TimDraper
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Episode Partners:
Delve
Delve 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/divot

Timestamps:
1:50 — Making a Divot: Entrepreneurs, Impact & Building for the Future
4:14 — Entrepreneurs Are Superheroes From Day One
5:06 — Mindset Beats Talent: Why Entrepreneurship Can Be Taught
6:52 — Real Results: Founders Trained, Companies Built, Unicorns Created
8:05 — Risk as Identity: When “Crazy” Becomes Your Advantage
10:10 — Be Your Own Media Company: Turning Attention Into Power
11:56 — Failure Doesn’t Matter: Why Nobody Remembers Your Mistakes
13:30 — Boom and Bust: Who Actually Survives Tech Cycles
14:24 — The Cost of Inaction: Missing Facebook, Uber & Airbnb
17:21 — Buying Bitcoin at $4: Conviction Before Consensus
18:55 — Why Bitcoin Survived: The Unbanked, Remittances & Reality
20:54 — Predictions vs Regulation: When the Future Gets Delayed
25:43 — Bitcoin vs the Dollar: Inflation, Power & Store of Value
32:14 — The SVB Wake-Up Call: When Banks Aren’t Safe
36:26 — Independent Thinkers Win: Why the 1% Build Everything
41:09 — Fixing Broken Systems: Growth, Markets & California
48:24 — Raising Independent Humans, Not Followers
50:39 — The Core Belief: You Have Your Own Path
52:31 — Measuring a Life by Impact, Not Status

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Hashtags:
#TimDraper #VentureCapital #Entrepreneurship #Startups #Investing #BillionDollarCompanies #Bitcoin #EconomicFreedom #Innovation #Founders #Leadership #FutureOfTechnology #DivotPodcast

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/aparnacd
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
01:44 – “This Time Is Different”: Why AI Adoption Is Unprecedented
02:13 – The Brick Phone Story: How Slow Adoption Used to Be
03:32 – The “Scanned Brochure” Moment: Early Web vs Early AI
04:27 – AI Agents at Work: Prompts as the New PRDs
05:37 – Designers Are Unlocked: Building End-to-End With AI Tools
06:26 – The “Barbell Team”: Model Whisperers + Product Builders
07:31 – How Aparna Stays Ahead: Build Things (No Shortcuts)
09:55 – Thin Steps vs Fat Steps: What Got Easy, What Became the Bottleneck
11:17 – Making AI a “Contact Sport”: Building Reflexive AI Habits
14:33 – 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 Signals
17:45 – Small Teams That Ship: Why ~10 People Can Build Fast Now
18:42 – Startup Opportunities: Rewriting the Web for Agents

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Hashtags:
#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/joshuareeves
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
01:44 – Why Most Startups Fail Before They Even Begin
02:27 – The Hidden Cost of Regulation
03:48 – Why Payroll and Benefits Matter More Than You Think
05:39 – The Real Reason Running a Business Feels So Hard
07:44 – The Benefit That Completely Changed Employee Loyalty
09:31 – What Sustainable Growth Actually Looks Like
11:34 – The Three Metrics That Truly Matter in Business
13:58 – Why Chasing Hypergrowth Can Destroy Great Companies
15:48 – Building a Company Meant to Last for Decades
17:20 – The Leadership Mindset That Separates Great Founders
18:54 – Why Being “Busy” Is Not the Same as Making Progress
20:21 – How to Identify People Who Will Actually Succeed
22:46 – How AI Is Changing the Way Teams Work
24:06 – Why Helping Others Is the Ultimate Advantage
25:32 – The Life Lessons That Shape Great Leaders
27:20 – Gratitude, Perspective, and Staying Grounded
29:33 – What Success Really Means (And What It Doesn’t)
31:43 – The One Principle That Guides Every Decision
33:22 – A Simple Philosophy for a Meaningful Life

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Hashtags:
#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_Andersen
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
1:39 — Who Brandt Andersen Really Is & Why His Story Matters
3:03 — The Skydive That Should Have Killed Him
8:47 — What Facing Death Taught Brandt About Life
14:02 — The Wild Childhood Stories That Shaped Him
18:10 — The Banksy Above His Fireplace & His Dark/Light Identity
22:30 — From Startup Exit to Hollywood Storytelling
28:41 — Producing Everest, Lone Survivor & American Made
32:12 — The Real Families Who Inspired I Was a Stranger
36:55 — Inside Syria: Crisis Through Human Eyes
41:38 — “Don't Judge People by Their Worst Day”
45:52 — Haiti Earthquake: Chaos, Hunger & Purpose
52:10 — The Moment That Changed His View of Humanity
1:12:03 — Trapped in the Malibu Fires With His Son
1:29:45 — What Brandt Ultimately Wants People to Understand

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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/davidmeltzer
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 — David’s Life: The Fall That Saved Him
2:21 — Akron Roots: Scarcity, Survival & a Single Mom Who Never Quit
4:58 — The Dream Life That Almost Destroyed Him
7:06 — His Wife’s Warning: The Sentence That Changed Everything
8:44 — Rebuilding the Man: The Four Values That Brought Him Back
10:51 — Losing $100M: The Collapse He Was Finally Prepared For
13:02 — The Habits That Saved His Marriage, Mind & Future
17:47 — Failing Faster: Why Losing Is the Only Way to Win
22:06 — Emotional Alchemy: Training His Reactions Every Single Day
29:32 — “Stop, Drop & Roll”: The Method That Resets His Entire Life
34:39 — Ego, Pain & Perspective: Understanding the Chemistry of a Breakdown
42:18 — Turning Trauma Into Purpose: How He Rewrote His Story
53:17 — The One Lesson He Wants to Leave Humanity
55:38 — “What I Hope God Says to Me When I Arrive”

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Hashtags:
#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/iamsquint
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 Introduction & how Squint became a visual storyteller
3:48 First camera at age five
5:17 Running a TV studio at eight
6:44 Deciding at ten to do this forever
8:09 The list he wrote at age 12
9:46 Shooting Nas for the first time
12:12 How he processes rejection
13:46 The Killers story
16:30 Identity vs his work
18:47 What makes a great picture
20:31 Reading emotion through the eyes
22:37 Atmosphere vs the subject
26:13 Black and white vs color
28:41 Training his eye
32:59 Mastering relationships in the industry
35:32 Showing people how he sees them
48:53 Steph Curry’s discipline & ego
50:20 Losing his father & rebuilding
56:01 What makes a great dad

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Hashtags:
#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_tsai
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 — Early Curiosity, Identity & Finding Her Path
3:12 — Lessons From Google & YouTube's Early Days
6:58 — The Decision to Build a Global Investing Platform
10:45 — Launching 500 & the Chaos of the First Years
14:40 — How Early-Stage Investing Changed Over a Decade
18:26 — The Traits She Sees in Exceptional Founders
22:51 — Speed, Humility & the Signals That Truly Matter
26:33 — Surviving Cycles & Leading Through Volatility
30:55 — What Backing 3,000+ Founders Teaches You
35:18 — Global Perspective: Why Innovation Comes From Everywhere
39:07 — Leadership Moments That Define a CEO
43:50 — Legacy, Purpose & Why Relationships Are the Real Scorecard

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Hashtags:
#GlobalFounders #VentureCapital #StartupLeadership #EarlyStageInvesting #FounderMindset #ScalingStartups #GlobalInnovation #WomenInVC #LeadershipLessons #BuildingEnduringCompanies #Entrepreneurship #500Global

Before helping lead the transformation of Salt Lake City’s urban core, Mike Maughan’s journey was shaped by discipline, faith, service, and a belief that leadership is defined by integrity above everything else.

In this conversation, he shares how he built his career across organizations with massive community impact, from Qualtrics to Smith Entertainment Group, and the lessons behind navigating billion-dollar city projects, activating live experiences, and helping bring an NHL team to Utah. He breaks down the principles that great leaders use to build trust, make clear decisions, and “never get blocked,” even in environments filled with complexity.

He reflects on the power of in-person connection in the age of AI, the importance of working with good people, and why ego and humility must coexist for leaders to scale. From frameworks for choosing what matters to the truth about toxic cultures, he explains why solving meaningful problems creates better careers than chasing passion.

A grounded masterclass in clarity, purpose, and impact, proving that real leadership is built on service, courage, and the commitment to make things happen.

Follow Mike - X (Twitter): https://twitter.com/MikeMaughan
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 — Why Being Different Beats Being 10x Better
1:25 — Transforming Salt Lake City’s Urban Core
5:26 — The Value of In-Person Connection in the AI Era
8:42 — A Framework for Choosing What Actually Matters
10:02 — Working With Good People & Recognizing Integrity
14:15 — The Cost of Toxic Environments
19:03 — Don’t Chase Passion — Solve Big Problems
25:05 — Ego + Humility: The Rare Leadership Combo
31:01 — Building Five for the Fight & Meaningful Causes
36:23 — Service as a Competitive Advantage
43:36 — How Great Leaders Deliver Hard News
57:44 — Bringing an NHL Team to Utah & Making Vision Real

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Hashtags:
#Leadership #PurposeDriven #ScalingImpact #CommunityBuilding #HighPerformance #AIandHumanConnection #SportsBusiness #FoundersMindset

Before leading global teams and raising more than $170 million to back exceptional founders, this journey started in a crowded home on the West Side of Detroit filled with Motown, discipline, and faith.

In this conversation, she shares how she went from Detroit public schools to Cass Tech and Wharton, then entered Silicon Valley and scaled teams from 14 to more than 1,000 at Google. From global leadership assignments to becoming a first-time CEO, she breaks down the lessons behind leading with conviction, humility, and principle.

She reflects on navigating high-stakes decisions, building trust at the executive level, and helping guide a major strategic transaction with one of the world’s most iconic companies. From serving on public company boards to investing at the Series A and B stage, she explains how operating experience shapes venture judgment and why she built a fund designed to support underestimated talent at scale.

A masterclass in purpose-driven leadership, discipline, and belief, proving that success does not require sacrificing values, family, or faith, and that building with integrity is not a weakness, but a competitive advantage.

Follow Stacy - X (Twitter): https://x.com/sbp04
Follow Derek - X (Twitter): https://twitter.com/derekjandersen

Timestamps:
0:00 — Growing Up in Detroit: Faith, Family & Strong Women
2:18 — Motown Culture, Community & Early Joy
4:01 — Hard Things Young: Grit & Gratitude in Scarcity
5:47 — “God Will Make a Way”: Faith in Difficult Moments
6:58 — Two Things Can Be True: Effort vs Surrender
8:32 — Education as Escape: Earning a Shot at Cass Tech
10:12 — Wharton Dreams Without a Roadmap
12:45 — Breaking Into Tech & Entering Silicon Valley
16:22 — From 14 to 1,000 Employees: Learning to Lead at Scale
19:06 — Leading in India: Humility, Culture & Listening
22:54 — Becoming CEO: Pressure, Confidence & Faith
28:30 — The IKEA Deal: Inside a Transformational Acquisition
33:44 — How Great Boards Really Work (No Surprises Rule)
48:10 — Building Cherry Rock Capital & Investing With Purpose
50:20 — How She Chooses Founders & Helps Them Scale
1:11:26 — Mind Over Matter: Overcoming Hard Seasons
1:12:12 — Marriage Strength & Building a Life Together
1:12:42 — Legacy: Faith, Kids, Meaning & Life’s Real Scorecard

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Hashtags:
#Leadership #SiliconValley #WomenInTech #TaskRabbit #Google #VentureCapital #FaithInBusiness #Entrepreneurship #FounderMindset #ScalingStartups