Divot

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
Follow Divot:
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X (Twitter): https://twitter.com/divotdotorg
Instagram: https://www.instagram.com/divotpod
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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
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
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)
Follow Divot:
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Instagram: https://www.instagram.com/divotpod
TikTok: https://www.tiktok.com/@divotpod
LinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:
#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
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
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
Follow Divot:
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LinkedIn: https://www.linkedin.com/company/divotdotorg
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
Manage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner
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
Follow Divot:
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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
Follow Divot:
YouTube: https://www.youtube.com/@Divotpod
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Instagram: https://www.instagram.com/divotpod
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LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#BobPearson #SurfboardShaping #BigWaveSurfing #Mavericks #ChasingMavericks #SurfingLegends #LairdHamilton #JayMoriarty #SurfDesign #SurfCulture #OceanLife #MentalHealth #Craftsmanship #Mastery #DivotPodcast