Recorded on Sand Hill Road at the iconic offices of Kleiner Perkins, this episode features Mamoon Hamid, one of the most influential investors of this generation. Mamoon has backed category-defining companies, including Slack, Figma, Box, Yammer, Glean, Intercom, and more, and now serves as a partner stewarding one of Silicon Valley’s most historic venture firms.

In conversation with Derek Andersen, Mamoon breaks down how great investors evaluate founders, why conviction starts with why, and what separates category creators from incremental startups.

The discussion expands into AI, where Mamoon shares why this cycle is fundamentally different from every prior technology wave. He explains why AI is not just software but labor, how it’s reshaping productivity across professions, and why adoption and monetization are happening faster than ever, from copilots to autonomous agents transforming how work gets done.

The episode closes with deeply personal reflections on resilience, immigration, parenting, faith, and purpose.

Follow Mamoon - X (Twitter): https://x.com/mamoonha
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

Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner

Timestamps:
00:00 — “God Is the Best of Planners” — Faith, Loss & Letting Go of Control
01:40 — Inside the Most Powerful Room in Silicon Valley (Why It’s Rarely Used)
05:05 — What Elite Investors Actually Listen For in Founder Pitches
06:55 — Why Metrics Don’t Matter If You Can’t Explain Your “Why”
10:30 — How Slack & Box Were Backed When the Market Didn’t Exist
14:25 — Why AI Is the Biggest Technology Shift in 30 Years
18:50 — AI Isn’t Software — It’s Labor (And That Changes Everything)
23:30 — The Future of Work: What Humans Will Do Better Than AI
27:10 — Leaving Your Own Firm to Rebuild a Legendary One
31:05 — The Apprenticeship Model That Built Venture Capital Giants
35:45 — Growing Up Between Germany & Pakistan — Lessons in Resilience
39:30 — How Do You Raise Resilient Kids in an Easy World?
42:55 — Why Sports Might Be the Best Teacher of Grit
49:55 — The Hajj: Witnessing the Best of Humanity Under Extreme Conditions
56:20 — Inshallah — Ambition, Failure & Accepting God’s Will
59:35 — How Mamoon Hamid Measures a Life Well Lived

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Hashtags:
#MamoonHamid #KleinerPerkins #VentureCapital #AI #FutureOfWork #Startups #Founders #FaithAndWork #Leadership #DivotPodcast

Before becoming a leader at the intersection of fashion, retail, and technology, Julie Bornstein built her career through persistence, curiosity, and conviction. Early on, she broke into the industry by reaching out directly to designers she admired, setting the foundation for a career that would later span Nordstrom, Sephora, Stitch Fix, and multiple consumer technology companies shaping how people discover what they wear.

In this conversation, Julie shares what she learned building and scaling consumer products and why fashion is one of the most complex categories for technology to understand.

Julie also reflects on the rapid shift now underway in commerce, as AI begins to reshape how people search, discover, and decide. She discusses why traditional e-commerce search fails in taste-based categories, how large language models unlock new possibilities for personalization, and what this moment has in common with earlier platform shifts like social and mobile.

The episode goes deeper into purpose and long-term thinking, exploring trust, incentive alignment, and how technology should serve people rather than manipulate them.

Follow Julie - X (Twitter): https://x.com/juliebornstein
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

Pulley
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Timestamps:
02:18 — She Broke Into Fashion by Writing Letters (No Network, No Shortcuts)
05:01 — The Business of Fashion Explained Simply (How Brands Really Make Money)
06:40 — Why Online Shopping Became Overwhelming (Too Much Choice Kills Confidence)
07:28 — Why Most Fashion Brands Fail (No Point of View, Wrong Pricing)
10:29 — Who Really Decides Fashion Trends? (Luxury, Runways & Fast Fashion)
14:28 — The Nordstrom Leader Who Saw E-Commerce Before Anyone Else
16:03 — Why Stitch Fix Didn’t Work for People With Real Taste
18:29 — Selling a Startup: 40K Customers vs 400M Users at Pinterest
23:52 — The 3 Reasons She Sold Her Company (Price, Market Crash, Team)
26:33 — Why ChatGPT Made AI Shopping Finally Possible
30:49 — Why Fashion Search Is Broken (Taste-Based, Not Keyword-Based)
34:10 — The Rule Behind Daydream: If the Customer Wins, We Win
44:30 — The Legacy She Wants to Leave (Making Shopping Smarter & Better)

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Hashtags:
#JulieBornstein #AIShopping #FutureOfCommerce #ConsumerAI #FashionTech #RetailInnovation #Startups #Founders #Technology #DivotPodcast

Before becoming one of the most respected early-stage investors in Silicon Valley, Niko Bonatsos was an immigrant from Greece navigating academia, visas, and uncertainty while searching for opportunity in the United States. Over the next 15 years, he became a Managing Director at General Catalyst, investing in iconic companies like Snap and Discord and backing technical founders long before their ideas became obvious to the world.

In this conversation, Niko shares what he learned investing through multiple technology cycles and why most successful companies don’t start with the right idea.

Niko also reflects on the resurgence of San Francisco as the center of the AI revolution, how ChatGPT reshaped the startup landscape almost overnight, and why this moment feels similar to the early days of social networking and mobile. From recognizing momentum before metrics to investing in overlooked builders, he offers a rare inside look at how early-stage conviction is actually formed.

The episode goes deeper into purpose and legacy, exploring immigration, perseverance, parenting, and how Niko measures a life well lived. Rather than chasing status, money, or permanence, he explains why helping deeply obsessed builders bring their dreams to life and empowering others along the way is the mark that truly matters.

Follow Niko - X (Twitter): https://x.com/bonatsos
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

Pulley
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Timestamps:
02:42 — Stanford & Silicon Valley: One Intertwined Ecosystem
06:18 — Why Founders Keep Chasing the Same Startup Ideas
07:37 — Investing Before Consensus: The Real Seed Advantage
08:22 — Why Most Successful Companies Don’t Start With the Right Idea
09:49 — San Francisco Is Back: The AI Gravity Shift
13:24 — Why Niko Invested Early in Snap
15:44 — Discord: How a Failed Startup Became a Generational Company
18:42 — Talent Is Universal, Opportunity Is Not
21:17 — The Signals That Make an Investor Lean In
26:49 — Can AI Replace Venture Capitalists?
31:30 — The Rise of Tiny Teams and Explosive Growth
34:01 — Why Non-AI Companies Are Fighting a Knife Fight
38:13 — Leaving General Catalyst: A New Chapter
42:18 — Alexander the Great & the Question of Legacy
48:19 — “Just Get Started”: The One Idea He’d Give Everyone
50:51 — How Niko Measures a Life Well Lived

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Hashtags:
#NikoBonatsos #VentureCapital #AI #Startups #SiliconValley #EarlyStageInvesting #Founders #Snap #Discord #GeneralCatalyst #Entrepreneurship #Innovation #DivotPodcast

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/guykawasaki
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

Pulley
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Timestamps:
1:09 — Starting Surfing at 60: Obsession Beats Talent
3:49 — Growing Up in Hawaii: Identity, Culture & Perspective
6:44 — Everybody Has Something to Hide: Privacy, Signal & Freedom
12:44 — Writing 18 Books: Why Most People Shouldn’t Write One
16:57 — Build for Yourself: The Origin of Great Products
18:20 — Working With Steve Jobs: Mission Over Ego
19:40 — Mission-Driven vs Ego-Driven Leadership
22:35 — The Halo Effect: Why You Should Be Skeptical of Authority
27:22 — Steve Jobs vs Elon Musk: Focus vs Scale
30:51 — Don’t Be the Next Steve Jobs. Be the First You
33:08 — Finding Your Calling: Loving the Entire “Sandwich”
46:31 — Jane Goodall: Purpose Without Retirement
52:19 — Guy’s Golden Touch: Finding Gold Early
57:24 — Grit as the Real Advantage
58:25 — Family, Legacy & Measuring a Life

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Hashtags:
#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/pearsonarrow
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
Pulley
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner

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

Follow Divot:
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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

Follow Divot:
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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