Divot

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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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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LinkedIn: https://www.linkedin.com/company/divotdotorg
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:
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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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LinkedIn: https://www.linkedin.com/company/divotdotorg
Hashtags:
#DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork