Divot

• #23: The Box Story: Startup Lessons, AI Disruption, and the Future of Work

  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/levieFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 – Welcome to Divot: Making Your Mark on the World0:19 – From College Project to $4 Billion Company1:31 – Free Rent, Big Dreams & Dropping Out2:43 – The Birth of Box and the Cloud Idea3:49 – The Pivot That Changed Everything6:45 – AI Disruption: Startups vs Incumbents10:56 – The New Economics of AI and Software13:07 – What Clay Christensen Still Teaches Us15:31 – AI Agents and the Future of Work20:17 – Managing Teams in the AI Era26:10 – How Box Shifted to an AI-First Company40:41 – Leadership, Abundance Mindset & Life LessonsFollow 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:#AI #FutureOfWork #Leadership #Startups #Entrepreneurship #SaaS #CloudComputing #AIInnovation #AaronLevie #Box #TechLeadership #DivotPodcast

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• #22: The Radical Candor Mindset: Honest Leadership, Feedback, and the Power of Truth

  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/kimballscottFollow Derek – X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 – Love and Truth: The Heart of Radical Candor0:32 – Meet Kim Scott: Redefining Modern Leadership1:09 – From Google and Apple to a Global Movement5:07 – From Moscow to Silicon Valley: An Unlikely Journey10:20 – The Birth of Radical Candor with Dan Pink13:22 – The “Bob Story”: When Kindness Becomes Cruel20:15 – The Radical Candor Framework Explained24:25 – Why the Feedback Sandwich Doesn't Work31:15 – Speaking Truth to Power: Feedback Up, Down & Sideways39:00 – Radical Respect: Humanity over Hierarchy50:07 – Coaching Tech CEOs and Building Trust58:42 – Radical Candor at Home and Final ReflectionsFollow 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:#RadicalCandor #Leadership #FeedbackCulture #HonestLeadership #RadicalRespect #WorkCulture #StartupLeadership #EmotionalIntelligence #LeadershipDevelopment #DivotPodcast

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• #21: The Netflix Story: Building, Failing, and Finding Balance from the Early Days of the Streaming

  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/mbrandolphFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 - Intro & Early Lessons - Learning to love the hard parts of the journey1:00 - Founding Netflix - The idea, early experiments, and the DVD-by-mail breakthrough8:00 - Beating Blockbuster - Finding product-market fit and using subscription to win17:00 - That Will Never Work - Rejection, optimism, and lessons from failure26:00 - Customer Obsession - Testing, talking to users, and learning fast35:00 - Subscription Revolution - Reinventing media and business models44:00 - Disruption Strategy - Why big companies can’t pivot and how startups win54:00 - Looker Story - Building again, scaling a B2B SaaS, and selling to Google1:03:00 - Redefining Success - What truly matters after billions made1:12:00 - Work-Life Balance - Designing a life that scales with your ambition1:20:00 - Founder Mindset - Focus, intuition, and ignoring noise1:27:00 - Legacy & Wisdom - Optimism, empathy, and success beyond workFollow 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:#NetflixStory #Entrepreneurship #Innovation #Leadership #StartupLessons #WorkLifeBalance #Resilience #SiliconValley #BusinessGrowth #FoundersJourney #Inspiration #StreamingRevolution

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• #20: Founding Atari & Chuck E. Cheese, Shaping Silicon Valley, and Reinventing Education with AI

  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/nolbushnellFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 - Introduction3:10 - Childhood & influence of play7:30 - The early “happy accidents” that led to Atari12:45 - Chuck E. Cheese origin & branding17:50 - Short fun vs long fun in product design22:30 - Culture at Atari / Silicon Valley roots27:15 - AI's future and reinvention of education31:40 - Passion, intensity, and entrepreneurial mindset36:55 - Thoughts on raising eight children41:20 - Lessons from mentors, especially Bob Noyce45:30 - Advice on persistence and relentlessness50:10 - Legacy: fun, learning, and transformationFollow 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:#Entrepreneurship #Leadership #Atari #ChuckECheese #ArtificialIntelligence #Education #Startups #Resilience #Innovation #SiliconValley #Gaming #FutureOfLearning

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• #19: Leading with Curiosity, Building Culture, and Finding Joy at Work

  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/anneraimondiFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 - From San Jose roots to Asana's COO1:13 - Childhood lessons from immigrant parents2:21 - Seeing herself as a problem solver2:46 - Curiosity as a leadership superpower4:12 - Building advocacy with customers and employees5:15 - Staying lighthearted in high-pressure rooms7:19 - Using humor and honesty to diffuse tension9:03 - Leading without yelling: turning up the right "dials"11:04 - Rallying teams around the customer's voice13:03 - What makes someone have outsized impact14:34 - Healthy ambition vs. territorial behavior17:24 - Why fun and joy matter at work18:26 - Defining culture: mission + values + norms20:17 - How to evaluate a company's culture23:01 - Can you change culture or must you choose it?24:34 - Leadership training and conscious leadership at Asana26:07 - Serving on boards: how she got her first seat29:07 - How board work makes you a better operator33:49 - Why she wanted to be in the boardroom33:57 - On being a "recovering perfectionist"34:54 - Balancing family, career, and letting go of perfection35:57 - What her kids might say about her work39:45 - Privilege, gratitude, and immigrant perspective39:45 - AI's impact on how teams are built42:02 - How to bring AI into a resistant culture43:19 - Asana's "AI first" approach46:07 - The leader she most admires48:16 - The one idea she'd implant in everyone's mind49:08 - Hardest accomplishment: 30-year marriage50:20 - Her best advice on resilience and bouncing back50:55 - What she's most proud of in her career52:02 - The measure of a life well lived53:11 - The impact she hopes to leave on the worldFollow 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:#DivotPodcast #Leadership #Culture #Curiosity #JoyAtWork #Asana #Entrepreneurship #Resilience #TeamBuilding #AI

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