Divot

Derek Andersen

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

  1. #37: AI, Venture Capital, Faith & The Future of Work with Mamoon Hamid (Kleiner Perkins)

    2D AGO

    #37: AI, Venture Capital, Faith & The Future of Work with Mamoon Hamid (Kleiner Perkins)

    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: YouTube: https://www.youtube.com/@Divotpod X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #MamoonHamid #KleinerPerkins #VentureCapital #AI #FutureOfWork #Startups #Founders #FaithAndWork #Leadership #DivotPodcast

    1h 2m
  2. #36: AI Shopping, The Future of Commerce & Why Trust Matters More Than Tech

    FEB 11

    #36: AI Shopping, The Future of Commerce & Why Trust Matters More Than Tech

    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/juliebornsteinFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve 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 PulleyManage 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 Else16:03 — Why Stitch Fix Didn’t Work for People With Real Taste18:29 — Selling a Startup: 40K Customers vs 400M Users at Pinterest23:52 — The 3 Reasons She Sold Her Company (Price, Market Crash, Team)26:33 — Why ChatGPT Made AI Shopping Finally Possible30:49 — Why Fashion Search Is Broken (Taste-Based, Not Keyword-Based)34:10 — The Rule Behind Daydream: If the Customer Wins, We Win44:30 — The Legacy She Wants to Leave (Making Shopping Smarter & Better) Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorgHashtags:#JulieBornstein #AIShopping #FutureOfCommerce #ConsumerAI #FashionTech #RetailInnovation #Startups #Founders #Technology #DivotPodcast

    47 min
  3. #35: Investing Before Consensus, The AI Shift & What Makes Great Founders Win

    FEB 4

    #35: Investing Before Consensus, The AI Shift & What Makes Great Founders Win

    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/bonatsosFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve 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 PulleyManage 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 Ecosystem06:18 — Why Founders Keep Chasing the Same Startup Ideas07:37 — Investing Before Consensus: The Real Seed Advantage08:22 — Why Most Successful Companies Don’t Start With the Right Idea09:49 — San Francisco Is Back: The AI Gravity Shift13:24 — Why Niko Invested Early in Snap15:44 — Discord: How a Failed Startup Became a Generational Company18:42 — Talent Is Universal, Opportunity Is Not21:17 — The Signals That Make an Investor Lean In26:49 — Can AI Replace Venture Capitalists?31:30 — The Rise of Tiny Teams and Explosive Growth34:01 — Why Non-AI Companies Are Fighting a Knife Fight38:13 — Leaving General Catalyst: A New Chapter42:18 — Alexander the Great & the Question of Legacy48:19 — “Just Get Started”: The One Idea He’d Give Everyone50:51 — How Niko Measures a Life Well Lived Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#NikoBonatsos #VentureCapital #AI #Startups #SiliconValley #EarlyStageInvesting #Founders #Snap #Discord #GeneralCatalyst #Entrepreneurship #Innovation #DivotPodcast

    54 min
  4. #34: Creativity, Obsession & Building Products That Change the World

    JAN 28

    #34: Creativity, Obsession & Building Products That Change the World

    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/guykawasakiFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve 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 PulleyManage 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 Talent3:49 — Growing Up in Hawaii: Identity, Culture & Perspective6:44 — Everybody Has Something to Hide: Privacy, Signal & Freedom12:44 — Writing 18 Books: Why Most People Shouldn’t Write One16:57 — Build for Yourself: The Origin of Great Products18:20 — Working With Steve Jobs: Mission Over Ego19:40 — Mission-Driven vs Ego-Driven Leadership22:35 — The Halo Effect: Why You Should Be Skeptical of Authority27:22 — Steve Jobs vs Elon Musk: Focus vs Scale30:51 — Don’t Be the Next Steve Jobs. Be the First You33:08 — Finding Your Calling: Loving the Entire “Sandwich”46:31 — Jane Goodall: Purpose Without Retirement52:19 — Guy’s Golden Touch: Finding Gold Early57:24 — Grit as the Real Advantage58:25 — Family, Legacy & Measuring a Life Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#GuyKawasaki #SteveJobs #ElonMusk #Apple #Canva #Entrepreneurship #Startups #Creativity #ProductBuilding #Leadership #Innovation #SiliconValley #Grit #Purpose #DivotPodcast

    1h 1m
  5. #33: Mastery, Craft & Surfing Giants - Shaping Boards That Defined Big Wave Surfing

    JAN 21

    #33: Mastery, Craft & Surfing Giants - Shaping Boards That Defined Big Wave Surfing

    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 X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #BobPearson #SurfboardShaping #BigWaveSurfing #Mavericks #ChasingMavericks #SurfingLegends #LairdHamilton #JayMoriarty #SurfDesign #SurfCulture #OceanLife #MentalHealth #Craftsmanship #Mastery #DivotPodcast

    1h 3m
  6. #32: Risk, Freedom & Building Billion-Dollar Companies Before the World Believed

    JAN 14

    #32: Risk, Freedom & Building Billion-Dollar Companies Before the World Believed

    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/TimDraperFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:DelveDelve 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 Future4:14 — Entrepreneurs Are Superheroes From Day One5:06 — Mindset Beats Talent: Why Entrepreneurship Can Be Taught6:52 — Real Results: Founders Trained, Companies Built, Unicorns Created8:05 — Risk as Identity: When “Crazy” Becomes Your Advantage10:10 — Be Your Own Media Company: Turning Attention Into Power11:56 — Failure Doesn’t Matter: Why Nobody Remembers Your Mistakes13:30 — Boom and Bust: Who Actually Survives Tech Cycles14:24 — The Cost of Inaction: Missing Facebook, Uber & Airbnb17:21 — Buying Bitcoin at $4: Conviction Before Consensus18:55 — Why Bitcoin Survived: The Unbanked, Remittances & Reality20:54 — Predictions vs Regulation: When the Future Gets Delayed25:43 — Bitcoin vs the Dollar: Inflation, Power & Store of Value32:14 — The SVB Wake-Up Call: When Banks Aren’t Safe36:26 — Independent Thinkers Win: Why the 1% Build Everything41:09 — Fixing Broken Systems: Growth, Markets & California48:24 — Raising Independent Humans, Not Followers50:39 — The Core Belief: You Have Your Own Path52:31 — Measuring a Life by Impact, Not Status Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#TimDraper #VentureCapital #Entrepreneurship #Startups #Investing #BillionDollarCompanies #Bitcoin #EconomicFreedom #Innovation #Founders #Leadership #FutureOfTechnology #DivotPodcast

    58 min
  7. #31: How AI Is Transforming Product Building, Leadership, and the Future of Work

    JAN 7

    #31: How AI Is Transforming Product Building, Leadership, and the Future of Work

    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: YouTube: https://www.youtube.com/@Divotpod X (Twitter): https://twitter.com/divotdotorg Instagram: https://www.instagram.com/divotpod TikTok: https://www.tiktok.com/@divotpod LinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags: #DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork

    21 min
  8. #30: How Gusto’s CEO Built a Category-Defining Company - Leadership, Scaling & Long-Term Growth

    12/31/2025

    #30: How Gusto’s CEO Built a Category-Defining Company - Leadership, Scaling & Long-Term Growth

    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/joshuareevesFollow Derek - X (Twitter): https://twitter.com/derekjandersen Timestamps:01:44 – Why Most Startups Fail Before They Even Begin02:27 – The Hidden Cost of Regulation03:48 – Why Payroll and Benefits Matter More Than You Think05:39 – The Real Reason Running a Business Feels So Hard07:44 – The Benefit That Completely Changed Employee Loyalty09:31 – What Sustainable Growth Actually Looks Like11:34 – The Three Metrics That Truly Matter in Business13:58 – Why Chasing Hypergrowth Can Destroy Great Companies15:48 – Building a Company Meant to Last for Decades17:20 – The Leadership Mindset That Separates Great Founders18:54 – Why Being “Busy” Is Not the Same as Making Progress20:21 – How to Identify People Who Will Actually Succeed22:46 – How AI Is Changing the Way Teams Work24:06 – Why Helping Others Is the Ultimate Advantage25:32 – The Life Lessons That Shape Great Leaders27:20 – Gratitude, Perspective, and Staying Grounded29:33 – What Success Really Means (And What It Doesn’t)31:43 – The One Principle That Guides Every Decision33:22 – A Simple Philosophy for a Meaningful Life Follow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotpodTikTok: https://www.tiktok.com/@divotpodLinkedIn: https://www.linkedin.com/company/divotdotorg Hashtags:#DivotPodcast #Leadership #Entrepreneurship #BuildingInPublic #SmallBusiness #FounderJourney #PurposeDriven #LongTermThinking #StartupLife #Grit #MeaningfulWork

    36 min
4.9
out of 5
19 Ratings

About

Divot brings you weekly conversations with the people building the future—founders, creators, athletes, and visionaries pushing the limits of business, technology, sports, and entertainment. We go beyond success stories to explore the real moments that define a journey—the risks, the failures, the breakthroughs, and the lessons that can help you on your path. Stories of people making their mark, and how you can too. New episodes every Wednesday. #DivotPodcast #Business #Tech #Sports #Entertainment #Innovation

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