This week on Generating Alpha, I’m joined by Barry Sternlicht — founder, chairman, and CEO of Starwood Capital Group, and one of the most accomplished real estate investors ever. Since founding the firm in 1991, Barry has grown Starwood into a global powerhouse with over $100 billion in assets under management, investing across every major real estate class. He has created and managed more than 80,000 hotels, multifamily, and residential units worldwide, while launching iconic hospitality brands like W Hotels, St. Regis, and 1 Hotels, redefining the way design and brand intersect with real estate.

Barry’s accomplishments extend far beyond hospitality. Under his leadership, Starwood has executed transactions totaling hundreds of billions of dollars, spanning hotels, residential, office, retail, and industrial properties. He has been recognized repeatedly as one of the most influential figures in real estate, known for his contrarian eye, his ability to anticipate market cycles, and his pioneering focus on sustainable development years before it became mainstream.

In our conversation, Barry reflects on a childhood shaped by resilience and early entrepreneurial ventures, the pivotal lessons he learned working under Neil Bluhm at JMB, and the rise of Starwood Hotels. We also dive into the biggest risks and near misses of his career, his philosophy on evaluating deals and negotiation, and the timeless advice he’d give to the next generation of leaders and entrepreneurs.