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1:14:02ENScott 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.
1:11:42ENAlain 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.
1:13:37ENSami 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.
1:21:27ENRoger 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.
1:23:21ENErik 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.







