Divot

Aaron Levie, co-founder and CEO of Box, transformed a college project into a billion-dollar SaaS platform. He dives into the lessons learned from Box's evolution and discusses the current AI disruption. Aaron explains why startups may thrive in new markets while incumbents should focus on adaptation. He highlights AI's potential to enhance productivity and the necessity for human oversight in automated processes. Plus, he shares insights on the changing role of CEOs in the AI landscape and emphasizes the importance of maintaining human relationships in business.

Kim Scott, New York Times bestselling author and leadership coach, dives into the principles of Radical Candor. She shares how her experiences at Google and Apple influenced her feedback-driven approach. Scott explores the origins of Radical Candor, emphasizing the balance of caring personally while challenging directly. She critiques the ineffective feedback sandwich and highlights the importance of honest communication in fostering trust. Valuable insights are offered on applying these ideas not just at work, but also in personal relationships.

Marc Randolph, co-founder and first CEO of Netflix, shares his entrepreneurial journey from a simple idea to challenging Blockbuster. He discusses the importance of experimentation, revealing that failure can lead to unexpected breakthroughs. The conversation touches on customer obsession, rapid-testing ideas, and cultivating a positive culture without losing personal balance. With insights on defining success, Marc emphasizes that ambition can coexist with a meaningful life, highlighting the moments that truly shape our paths.

Nolan Bushnell, the visionary behind Atari and Chuck E. Cheese, reflects on the playful origins of his groundbreaking companies. He delves into how fun and innovation shaped Silicon Valley, shares his thoughts on the importance of game-based learning through his venture, Exodexa, and explores the impact of AI in education. Nolan discusses lessons from mentors, the concept of 'marinating' ideas, and offers candid parenting advice. His insights reveal why creativity and persistence are crucial in facing challenges and shaping the future.

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

In this episode, Neal Harmon, CEO and co-founder of Angel, reveals how he went from a dairy farm in Idaho to building one of the fastest-growing entertainment companies in the world. Angel is behind global hits like Sound of Freedom, The Chosen, and Dry Bar Comedy — all chosen and funded by audiences, not executives.Neal shares the painful story of surviving a Disney lawsuit, why The Chosen split was harder than Disney, and how resilience, faith, and community helped Angel scale against all odds. He explains the secrets to viral storytelling, why constant testing wins, and how community-driven content is rewriting the rules of media.This is a story of resilience, disruption, and purpose, a blueprint for every builder, leader, and creator who wants to build something that lasts.Follow Neal Harmon - X (Twitter): https://x.com/nealsharmonFollow Derek - X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 - Intro: from Idaho farm to Hollywood disruptor2:30 - Why Angel gives audiences the power to greenlight stories6:00 - Building hits like Sound of Freedom, The Chosen, and Dry Bar Comedy10:00 - Lessons from AuraBrush, Squatty Potty, and viral ads15:00 - Surviving Disney's $62M lawsuit and crowdfunding $11M in 5 days21:00 - Why lawsuits can build resilience, not break it26:00 - The pain of The Chosen split and lessons learned33:00 - Angel Guild and the future of audience-driven entertainment38:00 - Preparing for AMGX: scaling with community investors44:00 - Family, faith, and raising 10 kids while building a company50:00 - What makes Angel Studios different from Hollywood55:00 - Neal's advice: why failure isn't real until you quit1:00:00 - Final reflections: leadership, humility, and legacyFollow 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 #Entrepreneurship #Leadership #Resilience #AngelStudios #SoundOfFreedom #TheChosen #DryBarComedy #DisruptHollywood #BusinessStrategy #StartupStories #CommunityBuilding #FaithInBusiness

In this discussion, Jeremy Andrus, CEO of Traeger Grills and former CEO of Skullcandy, delves into his journey of transforming brands into cultural icons. He shares insights on overcoming crises, particularly after Traeger's IPO, and emphasizes the shift from financial success to meaningful leadership. Jeremy also explores building products that foster community, the importance of daily habits, and how he instills tenacity in his six children. His candid perspective redefines success as creating joy and connection, not just profit.

The world is changing fast — and there’s no going back.In this episode, legendary Silicon Valley investor Navin Chaddha (Managing Partner at Mayfield) lays out a powerful prediction: “Every business will become an AI business — no exceptions.”We dive into what that really means for founders, industries, and the future of work. Navin introduces the concept of “vibe coding”, where 8 billion people can become builders — simply by describing what they want. He shares why SaaS is dying, how vertical AI models will dominate entire industries, and why physical AGI will transform the real world — from robots to logistics to healthcare.He also explains how billion-dollar companies will soon be built by teams of two or three people, thanks to the power of AI-native architecture.This episode is a wake-up call for every founder, builder, and leader who wants to stay ahead in the new AI era.Follow Navin Chaddha – X (Twitter): https://twitter.com/NavinChaddhaFollow Derek – X (Twitter): https://twitter.com/derekjandersenTimestamps:00:00 - Introduction00:38 - The Excitement of AI Technology02:10 - The Future of Coding and Development04:20 - Collaborative Intelligence in Action05:00 - The Era of 8 Billion Builders06:01 - Democratizing Entrepreneurship with AI07:42 - The Impact on Venture Capital08:54 - The Renaissance of Hardware11:44 - AI's Role in Physical Applications13:50 - Disruption in Home Appliances19:20 - Barriers to Physical AGI20:52 - Reimagining Industries with AI26:15 - The Great Equalizer of AIEpisode Partners:SalesforceStart faster with Salesforce Starter Suite.https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAOFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotdotorgTikTok: https://www.tiktok.com/@divot.orgLinkedIn: https://www.linkedin.com/company/divotdotorg/#DivotPodcast #AI #VerticalAI #AGI #FutureOfWork #NavinChaddha #MayfieldFund #VibeCoding #StartupStrategy #Innovation #TechInvesting #SaaSIsDead

How do you build an AI company trusted by the world's top enterprises, while surviving political oppression, hacking a country's internet, and rewriting the future of work?In this episode, Waseem Alshikh, co-founder and CTO of Writer, shares his extraordinary story. At 17, he launched his first startup in Syria — only to be imprisoned when the government tried to steal it for one dollar. In retaliation, he shut down the country's internet and fled to Lebanon. From there, he taught himself English, built groundbreaking NLP tools, and eventually launched one of the world's most trusted AI platforms.We explore how Writer built its own LLMs to serve enterprises like Uber, Deloitte, and Spotify; how AI agents are replacing outdated internal tools; and how a new generation of founders is reshaping pricing, trust, and innovation in the AI era.This episode is a masterclass in surviving chaos, scaling with focus, and building AI-first from Day One.Follow Waseem Alshikh - X (Twitter): https://x.com/waseem_sFollow Derek Andersen - X (Twitter): https://twitter.com/derekjandersenTimestamps:00:00 - Introduction to the Syrian Regime Collapse00:49 - Early Success with Digital Mapping01:42 - Government Takeover and Jail Experience04:00 - Hacking the Internet for Revenge05:36 - Escape to Lebanon and New Beginnings06:44 - Learning English and Computer Science08:08 - Transitioning to AI and Open Source09:22 - Building Generative AI Models10:15 - The Challenge of Language Localization12:44 - Why We Built Our Own AI Models13:30 - Enterprise Solutions and Customer Trust18:04 - The Role of AI in Productivity24:11 - Evolving Business Models in AI28:35 - Future of AI in Regulated Industries32:29 - Open Source vs. Proprietary AI34:08 - Starting an AI Company Today38:11 - The Journey from Startup to GrowthEpisode Partners:SalesforceStart faster with Salesforce Starter Suite.https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAOFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotdotorgTikTok: https://www.tiktok.com/@divot.orgLinkedIn: https://www.linkedin.com/company/divotdotorg/#DivotPodcast #AI #Innovation #StartupJourney #EnterpriseAI #MissionDriven #Resilience #WriterAI #FutureOfWork #Leadership #CTO #SaaS #DerekAndersen

How do you choose the right quest — the kind of mission that truly matters, and can survive in today’s world of regulation, politics, and entrenched incumbents?In this episode, Founders Fund General Partner and Anduril co-founder Trae Stephens shares his philosophy of “Good Quests” — and what entrepreneurs must get right when tackling hard, meaningful problems. We dive deep into how AI will transform defense and national security, why the future of warfare is distributed and AI-driven, and how entrepreneurs can navigate government sales and political opposition.From raising capital to surviving regulated markets, this is a tactical and inspiring conversation for anyone building in ambitious, frontier spaces.This episode is a masterclass in mission-driven entrepreneurship, AI strategy, and playing to win in a changing world.Follow Trae Stephens – X (Twitter): https://twitter.com/traestephensFollow Derek Andersen – X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 - Introduction: The Naivety of Building Products0:20 - Welcome to Divot and Episode Overview1:10 - Guest Introduction: Trae Stephens1:32 - The Concept of Good Quests for Founders3:50 - Identifying a Good Quest and Its Importance6:40 - Market Size and Its Relevance to Good Quests8:42 - Governance and Board Seats in Venture Capital10:02 - Coaching Founders on Ethical Considerations11:21 - Founding Anduril: Early Data Points and Insights14:58 - Raising Capital: Strategies for Founders17:55 - Selling to the U.S. Government and International Markets21:18 - The Role of AI in Defense and Future ImplicationsEpisode Partners:SalesforceStart faster with Salesforce Starter Suite.https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAOFollow Divot:YouTube: https://www.youtube.com/@DivotpodX (Twitter): https://twitter.com/divotdotorgInstagram: https://www.instagram.com/divotdotorgTikTok: https://www.tiktok.com/@divot.orgLinkedIn: https://www.linkedin.com/company/divotdotorg/#DivotPodcast #AI #Innovation #DefenseTech #Entrepreneurship #GoodQuest #MissionDriven #StartupLessons #Regulation #Leadership #TraeStephens