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1:14:02EN
20VC with Harry Stebbings· Jul 7, 2025Podcast · 2 speakersScott Galloway on Wealth, Work, Relationships and PurposeGuest Scott Galloway · Host Harry StebbingsThe professor and entrepreneur discusses market power, generational inequality and the personal cost of tying identity to money.
1:11:42EN20VC with Harry Stebbings· Nov 18, 2024Podcast · 2 speakersAlain de Botton on Status Anxiety and Finding Meaning at WorkGuest Alain de Botton · Host Harry StebbingsThe philosopher discusses recognition, parenting, careers and capitalism, and offers a way to think about ambition beyond fame.
1:13:37EN20VC with Harry Stebbings· Feb 28, 2024Podcast · 2 speakersSami Inkinen on Success, Family and a Founder’s IdentityGuest Sami Inkinen · Host Harry StebbingsThe Trulia co-founder and Virta Health CEO reflects on the anxiety that followed an IPO, rowing across the Pacific with his wife and building a life beyond work.
1:21:27EN20VC with Harry Stebbings· Feb 19, 2024Podcast · 2 speakersRoger Ehrenberg on Venture Returns, Liquidity and Life After SuccessGuest Roger Ehrenberg · Host Harry StebbingsThe IA Ventures founder examines a changing LP base, continuation funds and the trade-offs behind selling winners, then reflects on wealth and family.
1:23:21EN20VC with Harry Stebbings· Feb 7, 2024Podcast · 2 speakersErik Allebest on Building Chess.com, Growth and Life Beyond MetricsGuest Erik Allebest · Host Harry StebbingsChess.com’s co-founder explains how early revenue, content and a global remote team shaped the business, and why its ownership story is more complicated than no outside investment.
1:04:31EN20VC with Harry Stebbings· Jul 10, 2023Podcast · 2 speakersSimon Sinek on Trust, Listening and the Work of Being a Better LeaderGuest Simon Sinek · Host Harry StebbingsThe author discusses identity, difficult conversations and how leaders can create space for honest feedback and productive dissent.
1:42:20EN20VC with Harry Stebbings· Apr 17, 2023Podcast · 2 speakersScooter Braun on Success, Vulnerability and Finding Time for FamilyGuest Scooter Braun · Host Harry StebbingsThe music executive and investor reflects on achievement, public identity and the personal work he began after a difficult period in his life.
1:01:25EN20VC with Harry Stebbings· Feb 18, 2023Podcast · 2 speakersAloe Blacc on Songwriting, Fame and Creating a Life Beyond TouringGuest Aloe Blacc · Host Harry StebbingsThe singer describes his creative process, working with Avicii and the choices that shape his family life and new venture.
49:00EN20VC with Harry Stebbings· Aug 1, 2022Podcast · 2 speakersKirsten Green on Scaling a Venture Firm Without Losing FocusGuest Kirsten Green · Host Harry StebbingsForerunner’s founder explains how consumer insight guides investments, why growing a team is a second job, and how relationships made her career possible.
32:20EN20VC with Harry Stebbings· Jun 20, 2022Podcast · 2 speakersGary Vaynerchuk on Early Angel Investing, Family Business and a Long View of WorkGuest Gary Vaynerchuk · Host Harry StebbingsThe entrepreneur recounts his first investments, a difficult family-business conflict and how he thinks about confidence and time.
32:47EN20VC with Harry Stebbings· Jun 17, 2022Podcast · 2 speakersNick Jones on Building Soho House and Leading Through GrowthGuest Nick Jones · Host Harry StebbingsThe founder discusses early restaurant failures, hospitality, hiring and the challenge of balancing work with family.
59:29EN20VC with Harry Stebbings· Mar 11, 2022Podcast · 2 speakersHarley Finkelstein on Shopify, Leadership and Learning to Be Present at HomeGuest Harley Finkelstein · Host Harry StebbingsThe Shopify president discusses communication, anxiety and the lessons he and his wife have learned about partnership and parenting.
45:59EN20VC with Harry Stebbings· Mar 1, 2022Podcast · 2 speakersSahil Bloom on Building an Audience and Starting a Venture FundGuest Sahil Bloom · Host Harry StebbingsThe writer and investor discusses consistent content, media-led investing, luck and a changing definition of hard work.