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
Before the cloud powered the modern enterprise, it started with a college dorm, a borrowed garage, and a vision to make work simpler.
In this conversation, Aaron Levie, co-founder and CEO of Box, shares how he turned a college project into a billion-dollar SaaS company. From building during the early days of the internet to leading through massive technological shifts, Aaron reveals the lessons behind Box’s evolution from a storage startup to a global platform used by 70% of the Fortune 500.
He reflects on the rise of AI, how it’s reshaping the software industry, and why this moment mirrors the early days of cloud computing. From the changing economics of software to the new era of AI agents, Aaron explains what it takes to stay relevant and keep innovating when the rules of business change overnight.
A masterclass in resilience, adaptability, and leadership from one of Silicon Valley’s most curious minds, proving that innovation is less about technology and more about the people who dare to rethink it.
Follow Aaron - X (Twitter): https://x.com/levie
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 – Welcome to Divot: Making Your Mark on the World
0:19 – From College Project to $4 Billion Company
1:31 – Free Rent, Big Dreams & Dropping Out
2:43 – The Birth of Box and the Cloud Idea
3:49 – The Pivot That Changed Everything
6:45 – AI Disruption: Startups vs Incumbents
10:56 – The New Economics of AI and Software
13:07 – What Clay Christensen Still Teaches Us
15:31 – AI Agents and the Future of Work
20:17 – Managing Teams in the AI Era
26:10 – How Box Shifted to an AI-First Company
40:41 – Leadership, Abundance Mindset & Life Lessons
Follow Divot:
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Hashtags:
#AI #FutureOfWork #Leadership #Startups #Entrepreneurship #SaaS #CloudComputing #AIInnovation #AaronLevie #Box #TechLeadership #DivotPodcast
Before Radical Candor reshaped how leaders give feedback, it began with a simple idea, that caring personally and challenging directly can coexist.
In this conversation, leadership expert Kim Scott, bestselling author of Radical Candor and Radical Respect, reflects on how honesty, empathy, and courage transform the way we work and lead. She shares the real story behind creating Radical Candor, coaching top CEOs at Dropbox and Qualtrics, and how her experiences at Google and Apple University shaped her approach to management and life.
You'll learn how to give feedback that inspires growth, build teams rooted in respect, and create cultures where truth replaces fear. From her first lessons in Moscow to building global impact in Silicon Valley, Kim reveals why clarity is kindness, and why radical candor is the foundation of lasting trust.
A timeless conversation for founders, creators, and leaders searching for authenticity, courage, and connection in a noisy world.
Kim – X (Twitter): https://x.com/kimballscott
Follow Derek – X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 – Love and Truth: The Heart of Radical Candor
0:32 – Meet Kim Scott: Redefining Modern Leadership
1:09 – From Google and Apple to a Global Movement
5:07 – From Moscow to Silicon Valley: An Unlikely Journey
10:20 – The Birth of Radical Candor with Dan Pink
13:22 – The “Bob Story”: When Kindness Becomes Cruel
20:15 – The Radical Candor Framework Explained
24:25 – Why the Feedback Sandwich Doesn't Work
31:15 – Speaking Truth to Power: Feedback Up, Down & Sideways
39:00 – Radical Respect: Humanity over Hierarchy
50:07 – Coaching Tech CEOs and Building Trust
58:42 – Radical Candor at Home and Final Reflections
Follow Divot:
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Hashtags:
#RadicalCandor #Leadership #FeedbackCulture #HonestLeadership #RadicalRespect #WorkCulture #StartupLeadership #EmotionalIntelligence #LeadershipDevelopment #DivotPodcast
Before Netflix changed entertainment forever, it began with a small idea, mailed in an envelope, and a lot of doubt.
In this conversation, Marc Randolph, co-founder and first CEO of Netflix reflects on how experimentation, rejection, and persistence shaped one of the world’s most influential startups. He shares the real story behind challenging Blockbuster, creating the first subscription model, and learning why curiosity often matters more than certainty.
You’ll hear rare insights on how to test ideas quickly, stay optimistic through failure, and build a lasting culture without losing yourself in the process. More than a story of business success, this is about designing a meaningful life, where ambition and balance can coexist.
A timeless reflection for founders, creators, and leaders searching for clarity, courage, and direction in their own journey.
Marc - X (Twitter): https://x.com/mbrandolph
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 - Intro & Early Lessons - Learning to love the hard parts of the journey
1:00 - Founding Netflix - The idea, early experiments, and the DVD-by-mail breakthrough
8:00 - Beating Blockbuster - Finding product-market fit and using subscription to win
17:00 - That Will Never Work - Rejection, optimism, and lessons from failure
26:00 - Customer Obsession - Testing, talking to users, and learning fast
35:00 - Subscription Revolution - Reinventing media and business models
44:00 - Disruption Strategy - Why big companies can’t pivot and how startups win
54:00 - Looker Story - Building again, scaling a B2B SaaS, and selling to Google
1:03:00 - Redefining Success - What truly matters after billions made
1:12:00 - Work-Life Balance - Designing a life that scales with your ambition
1:20:00 - Founder Mindset - Focus, intuition, and ignoring noise
1:27:00 - Legacy & Wisdom - Optimism, empathy, and success beyond work
Follow Divot:
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Hashtags:
#NetflixStory #Entrepreneurship #Innovation #Leadership #StartupLessons #WorkLifeBalance #Resilience #SiliconValley #BusinessGrowth #FoundersJourney #Inspiration #StreamingRevolution
The journey from playful ideas to world-changing companies is never simple.
Known as the father of the video game industry, the founder of Atari, and Chuck E. Cheese has spent five decades at the intersection of play, technology, and entrepreneurship. In this episode, he shares how fun, innovation, and relentless curiosity shaped Silicon Valley, and why the future of learning depends on making it fun.
From pioneering the first home video games and building Atari into a cultural phenomenon, to creating Chuck E. Cheese and inspiring a generation of entrepreneurs, including Steve Jobs, he has shaped industries and defined eras. Today, his focus is on AI and education through his new venture, Exodexa, which he believes can transform how children learn by turning school into play.
He reflects on the happy accidents that led him to Atari, the unconventional culture that made Atari thrive, and why playfulness is essential to creativity and innovation. He opens up about raising eight children, the lessons he learned from mentors like Intel's Bob Noyce, and why persistence and relentlessness have been his greatest tools in overcoming challenges.
This is a raw and inspiring conversation for entrepreneurs, creators, and leaders who want to shape the future by rethinking what's possible.
Nolan - X (Twitter): https://x.com/nolbushnell
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 - Introduction
3:10 - Childhood & influence of play
7:30 - The early “happy accidents” that led to Atari
12:45 - Chuck E. Cheese origin & branding
17:50 - Short fun vs long fun in product design
22:30 - Culture at Atari / Silicon Valley roots
27:15 - AI's future and reinvention of education
31:40 - Passion, intensity, and entrepreneurial mindset
36:55 - Thoughts on raising eight children
41:20 - Lessons from mentors, especially Bob Noyce
45:30 - Advice on persistence and relentlessness
50:10 - Legacy: fun, learning, and transformation
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#Entrepreneurship #Leadership #Atari #ChuckECheese #ArtificialIntelligence #Education #Startups #Resilience #Innovation #SiliconValley #Gaming #FutureOfLearning
Work is changing fast, but how do you build cultures and teams that thrive through it?
In this episode, Anne Raimondi, COO and Head of Business at Asana, shares lessons from two decades leading fast-growth companies like Zendesk, SurveyMonkey, and TaskRabbit, serving on boards including Gusto and Patreon, and teaching leadership at Stanford GSB.
She opens up about growing up as the child of immigrants, why curiosity became her leadership superpower, and how she balances ambition with humility. You'll hear her talk about building resilient culture, using humor in high-pressure rooms, navigating perfectionism, and bringing AI into teams with trust and clarity.
Follow Anne Raimondi - X (Twitter): https://x.com/anneraimondi
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 - From San Jose roots to Asana's COO
1:13 - Childhood lessons from immigrant parents
2:21 - Seeing herself as a problem solver
2:46 - Curiosity as a leadership superpower
4:12 - Building advocacy with customers and employees
5:15 - Staying lighthearted in high-pressure rooms
7:19 - Using humor and honesty to diffuse tension
9:03 - Leading without yelling: turning up the right "dials"
11:04 - Rallying teams around the customer's voice
13:03 - What makes someone have outsized impact
14:34 - Healthy ambition vs. territorial behavior
17:24 - Why fun and joy matter at work
18:26 - Defining culture: mission + values + norms
20:17 - How to evaluate a company's culture
23:01 - Can you change culture or must you choose it?
24:34 - Leadership training and conscious leadership at Asana
26:07 - Serving on boards: how she got her first seat
29:07 - How board work makes you a better operator
33:49 - Why she wanted to be in the boardroom
33:57 - On being a "recovering perfectionist"
34:54 - Balancing family, career, and letting go of perfection
35:57 - What her kids might say about her work
39:45 - Privilege, gratitude, and immigrant perspective
39:45 - AI's impact on how teams are built
42:02 - How to bring AI into a resistant culture
43:19 - Asana's "AI first" approach
46:07 - The leader she most admires
48:16 - The one idea she'd implant in everyone's mind
49:08 - Hardest accomplishment: 30-year marriage
50:20 - Her best advice on resilience and bouncing back
50:55 - What she's most proud of in her career
52:02 - The measure of a life well lived
53:11 - The impact she hopes to leave on the world
Follow Divot:
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Hashtags:
#DivotPodcast #Leadership #Culture #Curiosity #JoyAtWork #Asana #Entrepreneurship #Resilience #TeamBuilding #AI
In this episode, Neal Harmon, CEO and co-founder of Angel, reveals how he went from a dairy farm in Idaho to building one of the fastest-growing entertainment companies in the world. Angel is behind global hits like Sound of Freedom, The Chosen, and Dry Bar Comedy — all chosen and funded by audiences, not executives.
Neal shares the painful story of surviving a Disney lawsuit, why The Chosen split was harder than Disney, and how resilience, faith, and community helped Angel scale against all odds. He explains the secrets to viral storytelling, why constant testing wins, and how community-driven content is rewriting the rules of media.
This is a story of resilience, disruption, and purpose, a blueprint for every builder, leader, and creator who wants to build something that lasts.
Follow Neal Harmon - X (Twitter): https://x.com/nealsharmon
Follow Derek - X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 - Intro: from Idaho farm to Hollywood disruptor
2:30 - Why Angel gives audiences the power to greenlight stories
6:00 - Building hits like Sound of Freedom, The Chosen, and Dry Bar Comedy
10:00 - Lessons from AuraBrush, Squatty Potty, and viral ads
15:00 - Surviving Disney's $62M lawsuit and crowdfunding $11M in 5 days
21:00 - Why lawsuits can build resilience, not break it
26:00 - The pain of The Chosen split and lessons learned
33:00 - Angel Guild and the future of audience-driven entertainment
38:00 - Preparing for AMGX: scaling with community investors
44:00 - Family, faith, and raising 10 kids while building a company
50:00 - What makes Angel Studios different from Hollywood
55:00 - Neal's advice: why failure isn't real until you quit
1:00:00 - Final reflections: leadership, humility, and legacy
Follow Divot:
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LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#DivotPodcast #Entrepreneurship #Leadership #Resilience #AngelStudios #SoundOfFreedom #TheChosen #DryBarComedy #DisruptHollywood #BusinessStrategy #StartupStories #CommunityBuilding #FaithInBusiness
The journey from startup to global brand is never easy, but it’s the moments of crisis that define true leaders.
In this episode, Jeremy Andrus, CEO of Traeger Grills and former CEO of Skullcandy, shares how he transformed two consumer brands into icons. From taking Skullcandy public to reinventing Traeger into the world’s number one wood-pellet grill company, Jeremy reveals the resilience and grit required to lead through chaos, culture shifts, and the toughest year of his career after going public.
We dive into the formula for building products people love, why culture and community fuel legendary brands, and how Jeremy redefined success from chasing money to creating meaning. He also opens up about raising a family of six, designing daily habits for strength, and why joy, not status, is the ultimate measure of life.
This is a raw and inspiring conversation for entrepreneurs, leaders, and anyone who wants to build with purpose and lead with resilience.
Follow Jeremy Andrus – Instagram: https://www.instagram.com/jeremy_andrus/
Follow Derek – X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 – Intro: turning products into experiences
2:00 – Food, community, and the emotional power of brand
6:00 – Why Traeger is about more than grills
10:00 – TVAC: the formula for building products that people love
13:00 – From financial pressure to purpose-driven leadership
18:00 – Sharing success with your team and rewarding loyalty
26:30 – Surviving IPO challenges and leading through 2022
28:30 – Finding happiness while going through pain
34:00 – Ego, humility, and separating identity from success
40:00 – Family, partnership, and redefining balance
48:00 – Morning routines, mini-habits, and building daily strength
57:00 – Teaching grit and tenacity to the next generation
1:03:00 – Core principles for building an authentic brand
1:09:00 – Culture, community, and scaling values worldwide
1:13:00 – Rapid fire: best advice, resilience, and measuring life
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags
#DivotPodcast #Leadership #Entrepreneurship #Resilience #BusinessGrowth #BrandBuilding #WorkLifeBalance #PersonalGrowth #CommunityBuilding #Success #Traeger #Skullcandy
The world is changing fast — and there’s no going back.
In this episode, legendary Silicon Valley investor Navin Chaddha (Managing Partner at Mayfield) lays out a powerful prediction: “Every business will become an AI business — no exceptions.”
We dive into what that really means for founders, industries, and the future of work. Navin introduces the concept of “vibe coding”, where 8 billion people can become builders — simply by describing what they want. He shares why SaaS is dying, how vertical AI models will dominate entire industries, and why physical AGI will transform the real world — from robots to logistics to healthcare.
He also explains how billion-dollar companies will soon be built by teams of two or three people, thanks to the power of AI-native architecture.
This episode is a wake-up call for every founder, builder, and leader who wants to stay ahead in the new AI era.
Follow Navin Chaddha – X (Twitter): https://twitter.com/NavinChaddha
Follow Derek – X (Twitter): https://twitter.com/derekjandersen
Timestamps:
00:00 - Introduction
00:38 - The Excitement of AI Technology
02:10 - The Future of Coding and Development
04:20 - Collaborative Intelligence in Action
05:00 - The Era of 8 Billion Builders
06:01 - Democratizing Entrepreneurship with AI
07:42 - The Impact on Venture Capital
08:54 - The Renaissance of Hardware
11:44 - AI's Role in Physical Applications
13:50 - Disruption in Home Appliances
19:20 - Barriers to Physical AGI
20:52 - Reimagining Industries with AI
26:15 - The Great Equalizer of AI
Episode Partners:
Salesforce
Start faster with Salesforce Starter Suite.
https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAO
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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Instagram: https://www.instagram.com/divotdotorg
TikTok: https://www.tiktok.com/@divot.org
LinkedIn: https://www.linkedin.com/company/divotdotorg/
#DivotPodcast #AI #VerticalAI #AGI #FutureOfWork #NavinChaddha #MayfieldFund #VibeCoding #StartupStrategy #Innovation #TechInvesting #SaaSIsDead
How do you build an AI company trusted by the world's top enterprises, while surviving political oppression, hacking a country's internet, and rewriting the future of work?
In this episode, Waseem Alshikh, co-founder and CTO of Writer, shares his extraordinary story. At 17, he launched his first startup in Syria — only to be imprisoned when the government tried to steal it for one dollar. In retaliation, he shut down the country's internet and fled to Lebanon. From there, he taught himself English, built groundbreaking NLP tools, and eventually launched one of the world's most trusted AI platforms.
We explore how Writer built its own LLMs to serve enterprises like Uber, Deloitte, and Spotify; how AI agents are replacing outdated internal tools; and how a new generation of founders is reshaping pricing, trust, and innovation in the AI era.
This episode is a masterclass in surviving chaos, scaling with focus, and building AI-first from Day One.
Follow Waseem Alshikh - X (Twitter): https://x.com/waseem_s
Follow Derek Andersen - X (Twitter): https://twitter.com/derekjandersen
Timestamps:
00:00 - Introduction to the Syrian Regime Collapse
00:49 - Early Success with Digital Mapping
01:42 - Government Takeover and Jail Experience
04:00 - Hacking the Internet for Revenge
05:36 - Escape to Lebanon and New Beginnings
06:44 - Learning English and Computer Science
08:08 - Transitioning to AI and Open Source
09:22 - Building Generative AI Models
10:15 - The Challenge of Language Localization
12:44 - Why We Built Our Own AI Models
13:30 - Enterprise Solutions and Customer Trust
18:04 - The Role of AI in Productivity
24:11 - Evolving Business Models in AI
28:35 - Future of AI in Regulated Industries
32:29 - Open Source vs. Proprietary AI
34:08 - Starting an AI Company Today
38:11 - The Journey from Startup to Growth
Episode Partners:
Salesforce
Start faster with Salesforce Starter Suite.
https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAO
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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LinkedIn: https://www.linkedin.com/company/divotdotorg/
#DivotPodcast #AI #Innovation #StartupJourney #EnterpriseAI #MissionDriven #Resilience #WriterAI #FutureOfWork #Leadership #CTO #SaaS #DerekAndersen
How do you choose the right quest — the kind of mission that truly matters, and can survive in today’s world of regulation, politics, and entrenched incumbents?
In this episode, Founders Fund General Partner and Anduril co-founder Trae Stephens shares his philosophy of “Good Quests” — and what entrepreneurs must get right when tackling hard, meaningful problems. We dive deep into how AI will transform defense and national security, why the future of warfare is distributed and AI-driven, and how entrepreneurs can navigate government sales and political opposition.
From raising capital to surviving regulated markets, this is a tactical and inspiring conversation for anyone building in ambitious, frontier spaces.
This episode is a masterclass in mission-driven entrepreneurship, AI strategy, and playing to win in a changing world.
Follow Trae Stephens – X (Twitter): https://twitter.com/traestephens
Follow Derek Andersen – X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 - Introduction: The Naivety of Building Products
0:20 - Welcome to Divot and Episode Overview
1:10 - Guest Introduction: Trae Stephens
1:32 - The Concept of Good Quests for Founders
3:50 - Identifying a Good Quest and Its Importance
6:40 - Market Size and Its Relevance to Good Quests
8:42 - Governance and Board Seats in Venture Capital
10:02 - Coaching Founders on Ethical Considerations
11:21 - Founding Anduril: Early Data Points and Insights
14:58 - Raising Capital: Strategies for Founders
17:55 - Selling to the U.S. Government and International Markets
21:18 - The Role of AI in Defense and Future Implications
Episode Partners:
Salesforce
Start faster with Salesforce Starter Suite.
https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAO
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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Instagram: https://www.instagram.com/divotdotorg
TikTok: https://www.tiktok.com/@divot.org
LinkedIn: https://www.linkedin.com/company/divotdotorg/
#DivotPodcast #AI #Innovation #DefenseTech #Entrepreneurship #GoodQuest #MissionDriven #StartupLessons #Regulation #Leadership #TraeStephens
In this inspiring conversation, we explore how AI will transform the future of business and work, and what it means for us as humans. You’ll hear why AI will soon perform 80% of 80% of human jobs, why full AI-first tools will surpass today’s co-pilots, and why most of AI’s impact will happen outside of tech.
But this is also a powerful life masterclass. From building billion-dollar startups to raising a family and staying energized at 70, we dive deep into resilience, happiness, and living an internally driven life.
You’ll learn how to power through failure, lead through change, balance ambition with presence, and why the most significant measure of life is doing what you love.
Follow Vinod Khosla – X (Twitter): https://twitter.com/vkhosla
Follow Derek – X (Twitter): https://twitter.com/derekjandersen
Episode Partners:
Salesforce
Start faster with Salesforce Starter Suite.https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAO
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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LinkedIn: https://www.linkedin.com/company/divotdotorg/
#DivotPodcast #AI #FutureOfWork #Entrepreneurship #Resilience #Leadership #SmallBusiness #Innovation #AGI #Mindset #Success
In this episode, Kobie Fuller invites us into his home gym — and into the mindset that’s driven him through elite athletics, startup investing, fatherhood, and personal growth. From sprint workouts to 24-hour fasts, Kobie shares how he uses physical discipline to sharpen mental clarity and lead with purpose.
He breaks down two core ideas that changed his life: “It takes what it takes” and neutral thinking — frameworks he learned from late mentor Trevor Moawad to overcome self-doubt, pressure, and negativity.
We explore how Kobie handles failure, centers his faith, coaches his kids, balances ambition with presence, and defines what it truly means to win. This is a masterclass in mindset, emotional leadership, and how to build a life that actually matters.
Follow Kobie – X (Twitter): https://x.com/kobiefuller
Follow Derek – X (Twitter): https://twitter.com/derekjandersen
Timestamps:
0:00 – Introduction
1:40 – Inside Kobie’s gym: how fitness drives clarity
2:00 – Track workouts, aging, and athletic self-awareness
5:16 – Why the 800 is the most brutal race
6:13 – Coaching his kids, and what youth sports reveal
8:20 – “It takes what it takes” – the mindset behind greatness
11:25 – Neutral thinking vs. toxic positivity
14:18 – Road rage, emotional discipline, and living by the Golden Rule
20:47 – Teaching neutral mindset to his kids
22:11 – Preemptive emotional mapping with Trevor Moawad
25:18 – Balancing work, presence, and guilt as a founder & father
28:00 – Monday fasts, spiritual resets, and weekly discipline
31:10 – Building long-term investor-founder relationships
32:30 – Having a spouse who helps you stay grounded
33:17 – Trusting God’s plan when life doesn’t go your way
35:37 – Accomplishing hard things: track, leadership, and family
40:45 – Privilege, pressure, and staying grateful
42:49 – The person he admires most: Jim Lowry
43:44 – What he’s most proud of (it’s not Harvard)
44:30 – Meeting God and leaving the world better
45:05 – How he will measure his life
Episode Partners:
SalesforceStart faster with Salesforce Starter Suite.
https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAO
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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LinkedIn: https://www.linkedin.com/company/divotdotorg/
#DivotPodcast #MindsetMatters #ItTakesWhatItTakes #NeutralThinking #EmotionalDiscipline #Fatherhood #Faith #Leadership #KobieFuller