Leadership

Leadership, Transparency, and the Power of Connection with Jonathan Goldstein

October 15, 2025

Leadership, Transparency, and the Power of Connection with Jonathan Goldstein

Jonathan Goldstein

Co-Founder & Chief Executive Officer of Cain

Willy was joined by Jonathan Goldstein, Co-Founder and CEO of Cain, an investment firm with approximately $14 billion in assets under management.

They discussed Jonathan’s upbringing and the strong foundation his family instilled in him, key lessons in leadership that he’s carried forward, pivotal moments throughout his career journey, the biggest risk he’s ever taken, insights into the hospitality sector and why the details matter, the importance of connection, and much more.

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