Divot

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

Vinod Khosla, founder of Khosla Ventures and co-founder of Sun Microsystems, shares thought-provoking insights on AI's transformative impact on the job market. He predicts AI will soon take over most mundane tasks, allowing humans to focus on their passions. The conversation delves into the role of startups as true innovators, the need for a balanced approach to education, and the significance of resilience in entrepreneurship. Khosla also emphasizes the importance of work-life balance and pursuing what you love, even amidst the rapid changes brought by technology.

In this episode, Kobie Fuller invites us into his home gym — and into the mindset that’s driven him through elite athletics, startup investing, fatherhood, and personal growth. From sprint workouts to 24-hour fasts, Kobie shares how he uses physical discipline to sharpen mental clarity and lead with purpose.He breaks down two core ideas that changed his life: “It takes what it takes” and neutral thinking — frameworks he learned from late mentor Trevor Moawad to overcome self-doubt, pressure, and negativity.We explore how Kobie handles failure, centers his faith, coaches his kids, balances ambition with presence, and defines what it truly means to win. This is a masterclass in mindset, emotional leadership, and how to build a life that actually matters.Follow Kobie – X (Twitter): https://x.com/kobiefullerFollow Derek – X (Twitter): https://twitter.com/derekjandersenTimestamps:0:00 – Introduction1:40 – Inside Kobie’s gym: how fitness drives clarity2:00 – Track workouts, aging, and athletic self-awareness5:16 – Why the 800 is the most brutal race6:13 – Coaching his kids, and what youth sports reveal8:20 – “It takes what it takes” – the mindset behind greatness11:25 – Neutral thinking vs. toxic positivity14:18 – Road rage, emotional discipline, and living by the Golden Rule20:47 – Teaching neutral mindset to his kids22:11 – Preemptive emotional mapping with Trevor Moawad25:18 – Balancing work, presence, and guilt as a founder & father28:00 – Monday fasts, spiritual resets, and weekly discipline31:10 – Building long-term investor-founder relationships32:30 – Having a spouse who helps you stay grounded33:17 – Trusting God’s plan when life doesn’t go your way35:37 – Accomplishing hard things: track, leadership, and family40:45 – Privilege, pressure, and staying grateful42:49 – The person he admires most: Jim Lowry43:44 – What he’s most proud of (it’s not Harvard)44:30 – Meeting God and leaving the world better45:05 – How he will measure his lifeEpisode 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 #MindsetMatters #ItTakesWhatItTakes #NeutralThinking #EmotionalDiscipline #Fatherhood #Faith #Leadership #KobieFuller

Most people fail at leadership because they complicate what should be simple. Greg Osborn’s approach is different. After leading in Vietnam, raising a family with old-school work ethic, and building businesses in Silicon Valley as the tech boom took off, he learned that success comes from two things: giving people the right training and keeping them motivated.In this conversation, Greg breaks down why teams succeed or fail based on this simple principle — and how you can apply it in business, family, and life. You’ll hear how his leadership lessons from the Vietnam battlefield translated into managing people, teaching his kids, and running companies.This is timeless advice that still works today — practical, proven, and refreshingly clear.Follow Derek – X (Twitter): https://twitter.com/derekjandersenTimestamps:00:00 - Introduction to Greg Osborne and His Garage05:01 - Camping Adventures with Greg Osborne's Family10:01 - The Joy of Making and Solving Problems15:00 - Early Life, Education, and Military Background20:01 - College Basketball Career at Stanford25:01 - Physical Challenges and Surgeries Over the Years30:01 - Reflections on Basketball and Life Experiences35:01 - Military Training and Assignment to Vietnam40:02 - Experiences in Vietnam and Impact of War45:01 - Teaching GED to Soldiers and Life Lessons50:01 - 54 Years of Marriage and Family Life55:00 - Raising Children and Teaching Responsibility01:00:00 - Reflections on Joy and Family01:05:00 - Personal Anecdotes and Life Lessons01:10:00 - Challenges and Sacrifices in Life01:15:02 - Real Estate Experiences and Business Ventures01:20:01 - Encounters with Tech Industry Leaders01:25:00 - Growth of Silicon Valley and Early Tech Companies01:30:01 - Closing Thoughts and Final ConversationsEpisode 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/divotdotorgFollow Derek – X (Twitter): https://twitter.com/derekjandersen#DivotPodcast #Leadership #TeamSuccess #Entrepreneurship #SimpleAdvice #Motivation #HighPerformance #Mindset #PaloAlto

America used to lead the world in innovation. Now, it's falling behind — and no one in power wants to face the truth.In Part 2 of this eye-opening conversation, we dive into how the U.S. lost its edge in science, technology, and defense. From bloated bureaucracies to outdated mindsets, the systems that once fueled American greatness are now holding it back.You'll hear war stories from the frontlines of government innovation, uncover the forgotten WWII playbook that built modern America, and learn how China quietly leapfrogged U.S. capabilities. We explore why bold ideas get killed, how real change gets buried, and what kind of leadership we desperately need today.This isn't just about startups — it's about the future of the country.Follow Steve – X (Twitter): https://twitter.com/sgblankFollow Derek – X (Twitter): https://twitter.com/derekjandersenTimestamps:3:37: Hacking for Defense -- how a new form of national service is changing how national security problems are solved6:27: Why DoD struggles to innovate11:31: How China beat the U.S. at innovation21:00: How the U.S. became a science superpower27:00: Faith vs. facts: how decisions should be made35:15: Why the Office of Strategic Capital is one of the most creative things to happen to DoD40:47: How to get to the outcome you want: Fact-based conversations vs. Faith-based conversations43:51: Putting startup risk in context50:34: Redefining service52:30: Retirement, legacy & how to measure your lifeEpisode Partners:SalesforceStart faster with Salesforce Starter Suite.https://www.salesforce.com/form/signup/freetrial-salesforce-starter/?d=701ed000007ZTPhAAOM/Follow 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 #InnovationCrisis #AmericanDecline #Startups #GovernmentInnovation #Leadership #SiliconValley #ChinaVsUS #SteveBlank