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What Great Founders Do Differently (That No One Talks About)
In this episode of the Magic Minds podcast, we sit down with legendary entrepreneur and investor Spencer Rascoff for an unfiltered conversation on startups, leadership, and scaling through adversity. From growing up on tour with the Rolling Stones to co-founding Hotwire and Zillow, Spencer shares powerful stories from a career defined by bold pivots, world-class execution, and servant leadership. We explore what makes a great founder, why charisma and storytelling often outweigh raw technical skill, and how he’s seen passion and resilience make or break companies. Spencer also gets candid about leading through crises—including 9/11 as a young founder—and how those moments shaped his leadership style. We even dive into the underrated role of kindness in business, why sales is the hidden superpower of top CEOs, and what it takes to attract and align great talent. Whether you're a first-time founder or a seasoned operator, this is a masterclass in building, surviving, and thriving in tech. Don’t miss it. #GreatFounders #StartupLeadership #SpencerRascoff #ZillowFounder #EntrepreneurPodcast #StartupAdvice #ScalingStartups #ServantLeadership #FounderStories #TechLeadership #SalesForCEOs #StartupResilience #HowToBuildStartups #FounderCharisma #KindnessInBusiness #CrisisLeadership #StorytellingInBusiness #HotwireCoFounder #MagicMindsPodcast #BuildingTechCompanies Chapters 00:00 Welcome & Introduction to Spencer Raskoff 01:00 Spencer’s Childhood & His Father’s Music Industry Legacy 02:28 Reinventing the Concert Touring Business Model 04:43 Spencer’s Entrepreneurial Path & Career Highlights 06:10 Why Spencer Didn’t Enter the Music Business 07:11 Spencer as a Young Founder vs. Now 09:35 The Underrated Power of Sales in Startups 12:00 Example: Picasso & the Role of Sales in Startup Success 14:16 The Ideal Founding Team: Product, Engineering, Sales 16:30 Founder Passion & Finding the Right Fit 18:53 The Importance of Fundraising Ability in Founders 21:16 How Great Founders Tell Their Story & “Read the Room” 23:36 Spencer’s Leadership Style & Servant Leadership Origins 25:57 The Defining Moment: Hotwire & 9/11 28:19 Pivoting, Survival, and Lessons from the Crisis 30:41 How Spencer Teaches Crisis Leadership at Harvard 33:03 Reconnecting to Mission After Layoffs 35:22 The Myth of the Harsh Founder & Power of Kindness 37:47 Role Models in Kind Leadership & Influence of Family 40:14 Spencer’s Wife & Modeling Empathetic Professionalism 42:39 Coachability & Active Listening in Investor Pitches 44:39 Q&A – Why Co-founder Relationships Fail 47:05 Q&A – Operator vs. Founder: Spencer’s Career Choices 48:30 Q&A – Can Sales Skills Be Learned? 49:27 Q&A – Improving Human Connection in Dating Apps 51:50 Q&A – Prioritizing User Outcomes at Match Group 53:59 Q&A – Managing Mental Health & Workload 56:22 Q&A – One Pattern Among Successful Founders Spencer Rascoff's Social Media Accounts: https://www.linkedin.com/in/spencerrascoff https://x.com/spencerrascoff https://www.instagram.com/spencerrascoff
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