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. #43: Success Won’t Fix You (What a $4B CEO Learned Too Late)

    VOR 2 TAGEN

    #43: Success Won’t Fix You (What a $4B CEO Learned Too Late)

    Before leading a $4B company, Adam Edmunds spent years trying to prove he was good enough. From cold emailing CEOs as a student to building his first company, his journey started with uncertainty and a relentless need for validation. In this conversation with Derek Andersen, Adam shares how he became CEO of Entrata, a platform powering over 20,000 apartment communities worldwide, raising $700M+ and reaching a $4B+ valuation. He breaks down what it really takes to scale a company at that level. Adam explains why relationships are the most valuable currency in business, how great leaders recruit over years, not weeks, and why reputation determines the ceiling of your success. He also shares hard lessons on hiring, culture, and long-term thinking. The episode goes deeper into identity, failure, and self-worth, why success doesn’t fix how you feel about yourself, and how learning to stop seeking external validation changed everything about how he leads and lives. Follow Adam - X (Twitter): https://x.com/adamedmundsFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:Google for StartupsEverything you need to build and scale AI agents, from tools to expert guidance: g.co/startupagentguide PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride: https://tinyurl.com/PulleyPartner Timestamps:03:52 — The Power of Starting Before You’re Ready07:41 — Cold Emails That Changed His Life Forever12:58 — Building His First Company From Scratch18:36 — Inside a $4B Company (Entrata Breakdown)24:11 — How Great CEOs Think About Hiring Talent30:27 — Why Relationships Are the Ultimate Business Asset36:48 — Leadership, Culture, and Scaling Teams43:55 — The Hidden Cost of Success and Achievement50:12 — Why Success Doesn’t Fix Your Self-Worth56:34 — Redefining Identity Beyond Business1:01:22 — What Actually Matters at the End 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:#ceomindset #startupgrowth #scalingbusiness #founderjourney #leadershipskills #buildinginpublic #entrepreneurmindset #businessstrategy #personalgrowth #divotpodcast

    1 Std. 8 Min.
  2. #42: How Crumbl Founder Built a $1B Cookie Empire From One Cookie

    25. MÄRZ

    #42: How Crumbl Founder Built a $1B Cookie Empire From One Cookie

    Before building Crumbl, Jason McGowan was a tech founder focused on virality, creating products used by over 120 million people. He then made a bold move: leaving tech to start a simple cookie business. In this conversation with Derek Andersen, Jason shares how Crumbl grew from one chocolate chip cookie into a $1B+ franchise with 1,000+ locations across the U.S. He explains how product-market fit, A/B testing, and viral growth turned a simple idea into a national brand. Jason breaks down why product matters more than marketing, how customer obsession drives growth, and how Crumbl built a viral experience through sharing, weekly drops, and community feedback. The episode also explores leadership, success, and why money doesn’t create lasting happiness. Jason reflects on family, purpose, and what truly matters after building a billion-dollar company. Follow Jason - X (Twitter): https://x.com/jasonmcgowanFollow Derek - X (Twitter): https://twitter.com/derekjandersen Episode Partners:PulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:04:32 — Building the Perfect Cookie With A/B Testing07:18 — The Bubblegum Cookie Failure (Hard Lesson)08:54 — The Simple Idea Behind Crumbl’s Viral Growth17:58 — Owning the Customer (Lessons from Facebook)20:03 — How Crumbl Accidentally Became a Franchise22:43 — Why Product Matters More Than Marketing26:18 — Reading Reddit as CEO (Customer Obsession)30:34 — Scaling Crumbl Nationwide34:16 — Weekly Drops: The Genius Behind the Menu44:48 — Money Doesn’t Buy Happiness (Real Talk)46:25 — Family, Purpose, and What Actually Matters54:53 — The Truth About Success and Fulfillment59:26 — Just Get Started (Final Advice) 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:#NegotiationSkills #Stanford #BusinessNegotiation #Persuasion #Leadership #Startups #VentureCapital #Entrepreneurship #DealMaking #DivotPodcast

    1 Std. 2 Min.
  3. #41: Stanford Negotiation Expert Reveals the Psychology of Winning Any Negotiation

    18. MÄRZ

    #41: Stanford Negotiation Expert Reveals the Psychology of Winning Any Negotiation

    Before teaching negotiation at Stanford, Stan Christensen spent decades advising leaders on high-stakes negotiations around the world. From corporate finance on Wall Street to the consulting arm of the Harvard Negotiation Project, he has worked across more than 75 countries helping leaders navigate complex negotiations where the outcome can shape companies, careers, and international relationships. In this conversation with Derek Andersen, Stan explains why most people misunderstand negotiation. Instead of treating it like a battle where one side wins and the other loses, he argues that the best negotiators focus on preparation, deep listening, and creative problem-solving to build outcomes where both sides leave stronger. Stan shares lessons from venture capital negotiations, startup fundraising, job offer negotiations, and company acquisitions. He explains why founders should never negotiate with only one investor, why controlling the process matters when selling a company, and why the biggest mistake negotiators make is agreeing to deals they should walk away from. The episode goes deeper into leadership, persuasion, and human psychology, exploring why negotiation is ultimately about relationships. Subscribe to Stan’s Podcast - YouTube: https://www.youtube.com/@AllThingsNegotiationFollow 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:00:04:06 — The Steve Young Story: Giving People What They Value Most00:05:18 — Why Fairness Matters in Negotiation00:06:12 — Preparing for High-Stakes Negotiations00:07:34 — Why the Best Negotiators Listen More Than They Speak00:08:45 — Why Negotiation Is Creative Problem Solving00:11:06 — The Biggest Mistake in Business Negotiations00:12:29 — How to Negotiate a Job Offer (Early vs Senior Career)00:17:30 — Venture Capital Negotiations: Why Founders Need Leverage00:29:51 — Selling a Company: Why You Must Control the Process00:39:27 — The Story That Solved a 100-Year Conflict00:46:07 — How Stan Measures Success in 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:#NegotiationSkills #Stanford #BusinessNegotiation #Persuasion #Leadership #Startups #VentureCapital #Entrepreneurship #DealMaking #DivotPodcast

    47 Min.
  4. #40: How Filevine Founder Ryan Anderson Built a $3B Legal AI Platform

    11. MÄRZ

    #40: How Filevine Founder Ryan Anderson Built a $3B Legal AI Platform

    Before building one of the fastest-growing legal technology companies in the United States, Ryan Anderson was a practicing lawyer frustrated by deadlines, paperwork, and systems that made it easy to miss critical details. Instead of accepting the chaos of legal operations, he decided to build a better system. In this conversation with Derek Andersen, Ryan shares how that decision became Filevine, a legal tech platform now serving nearly 6,000 customers, employing more than 700 people, and generating more than $200 million in annual revenue. He explains how AI is transforming legal work and why technology can dramatically improve outcomes for lawyers and their clients. Ryan also opens up about rebuilding Filevine to become an AI-native company. From rewriting years of engineering work to navigating one of the fastest-moving industries in the world, he reflects on leadership, conviction, and what it takes to adapt when technology changes everything. The episode goes deeper into entrepreneurship, justice, and purpose, exploring why access to legal systems is expanding and why great lawyers will become even more powerful with AI. Follow Ryan - X (Twitter): https://x.com/ryanm_andersonFollow 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 — What Filevine Actually Does (Legal AI Explained)04:08 — The Problem That Inspired Filevine05:03 — The Risk Conversation With His Wife09:03 — Meeting the Engineer Who Built the Vision11:56 — The Founder Mindset: “I’ll Figure It Out”18:20 — The Day Ryan Quit His Job22:14 — Rewriting Filevine for the AI Era25:41 — How AI Is Changing Software Teams31:28 — Why the Legal Industry Could Grow 100x44:55 — The Future of Law: AI Running Legal Work55:20 — The Mindset to Build a Billion-Dollar Company01:06:10 — Ryan’s Real Definition of Success 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:#RyanAnderson #LegalAI #LegalTech #Entrepreneurship #SaaS #ArtificialIntelligence #Leadership #Justice #Innovation #DivotPodcast

    1 Std. 8 Min.
  5. #39: How Master Mechanic Dave Bell Built an 8M-Follower YouTube Empire

    4. MÄRZ

    #39: How Master Mechanic Dave Bell Built an 8M-Follower YouTube Empire

    Before becoming one of the most respected independent mechanics in the United States, Dave Bell was a young man battling addiction, jail time, and the fear of losing everything. Over the past 36 years, he rebuilt his life the same way he rebuilds engines, with discipline, precision, and relentless ownership. In this conversation, Dave shares how he grew from a one-bay storage unit during the 1990 recession into a 33,000-square-foot auto center with 35 employees, and how an unexpected leap into social media led to more than 8 million followers across YouTube, TikTok, and Instagram. He explains why opposition is an opportunity, how elite mechanics think, and why authenticity online outperforms any marketing budget. Dave also opens up about addiction, faith, jail, and the turning points that changed his trajectory. From reading Atlas Shrugged behind bars to building one of the largest independent automotive brands in the world, he reflects on agency, momentum, and the power of choosing who you become. The episode goes deeper into leadership, fatherhood, and legacy, exploring what it means to master yourself, redefine a misunderstood industry, and live by a simple philosophy: never let anyone else define who you are. Follow Dave - Instagram: https://www.instagram.com/davesautocenterFollow 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/divotPulleyManage your cap table with intuitive tools built to help founders make informed decisions without breaking stride. https://tinyurl.com/PulleyPartner Timestamps:02:42 — From 300 Followers to 8 Million: The Unexpected Breakthrough09:07 — “Who Are You?” The Identity Wake-Up Call13:19 — A Mission Bigger Than Cars: Changing an Entire Industry16:55 — Fearless: What Separates Elite Mechanics from Everyone Else26:42 — “Don’t Ever Let Anyone Define You” (A Father’s Turning Point)33:14 — The 4 O’s: Turning Opposition Into Opportunity45:17 — Drugs, Fast Money & Walking Away Before It Was Too Late50:48 — Rock Bottom at 35: Addiction, Faith & Choosing a Different Path57:35 — Six Months in Jail & The Book That Rewired His Mind01:01:50 — The Hard Truth: The Moment You Blame, You Lose01:09:40 — Momentum, Waves & The “Perfect Soup” Theory of Life01:10:11 — In the End, Only One Thing Matters 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:#DaveBell #Entrepreneurship #AddictionRecovery #MechanicLife #Leadership #BusinessGrowth #SocialMediaSuccess #AtlasShrugged #PersonalDevelopment #Agency #Momentum #AutoIndustry #DivotPodcast

    1 Std. 16 Min.
  6. #38: Building Great Products, Product Leadership & the Future of Work with Tomer Cohen (LinkedIn)

    25. FEB.

    #38: Building Great Products, Product Leadership & the Future of Work with Tomer Cohen (LinkedIn)

    Recorded at LinkedIn headquarters in Mountain View, this episode features Tomer Cohen, former Chief Product Officer of LinkedIn and one of the product leaders behind how over one billion professionals connect, work, and create economic opportunity at global scale. In conversation with Derek Andersen, Tomer breaks down what it takes to build great products inside large organizations, how LinkedIn evolved into a mobile-first platform, and what product leadership really means when operating at massive scale. The discussion expands into AI and the future of work, where Tomer explains the rise of the full-stack product builder, how AI is collapsing traditional roles across product, design, and engineering, and why builders who combine vision, empathy, and execution will define the next generation of companies. The episode closes with deeply personal reflections on growth mindset, restraint, resilience, faith, and the idea that true freedom lives in the space between stimulus and response. Follow Tomer - LinkedIn: https://www.linkedin.com/in/tomercohenFollow 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:00:00 — Between Stimulus and Response: Where Freedom Truly Lives08:55 — Rebuilding LinkedIn for Mobile Before It Was Obvious11:02 — Turning LinkedIn Into a Daily Habit, Not a Transaction13:34 — Why Authentic Voices Beat Corporate Talk Every Time18:24 — Conviction Over Titles: Choosing Where to Make Impact20:28 — The Rider and the Elephant: How Organizations Really Move24:42 — What Separates a Good Product from a Truly Great One31:34 — Restraint: The Hidden Skill Behind Billion-Dollar Products35:09 — Slowing Down to Fix the Core Before Scaling39:12 — The Rise of the Full-Stack Product Builder42:02 — How AI Is Collapsing Roles and Restoring Meritocracy53:25 — The Truth About Success: There Are No Shortcuts59:55 — The Final Lesson: Choosing How You Respond 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:#TomerCohen #LinkedIn #ProductLeadership #BuildingGreatProducts #AI #FutureOfWork #ProductManagement #StartupLeadership #GrowthMindset #DivotPodcast

    1 Std. 7 Min.
  7. #37: AI, Venture Capital, Faith & The Future of Work with Mamoon Hamid (Kleiner Perkins)

    18. FEB.

    #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

    1 Std. 2 Min.
  8. #36: AI Shopping, The Future of Commerce & Why Trust Matters More Than Tech

    11. FEB.

    #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.
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Info

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

Informationen

  • Erstellt von
    Derek Andersen
  • Jahre aktiv
    2025 - 2026
  • Folgen
    44
  • Bewertung
    Unbedenklich
  • Copyright
    © Derek Andersen
  • Sendungswebsite
    Divot

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