B”H

Today we’re diving into a thrilling story – one of ambition, bold moves, devastating setbacks, and ultimately, profound lessons about wealth, faith, and what really matters. My guest is Rabbi Irwin Katsof, former fundraiser for Aish HaTorah, now investor, entrepreneur, and president of Trademissions.org. He’s also the author of several books, including the one we’ll be talking about today, Living Dangerously: My Struggle to Get Rich Without Losing My Soul.

Rabbi Katsof shares with raw honesty what it was like to leave behind a wildly successful 20 plus-year career in Jewish outreach to try to “make it big” on Wall Street. We talk about the allure of wealth, the mistakes that led to overextension, the tension between ambition and faith, and the moments of humility that brought him back to center. We also touch on the lessons of bitachon, the impact of upbringing on our money stories, the dangers of chasing status symbols, and ultimately, what it really means to live a life of meaning, connection, and success.

This one is vulnerable, relatable, and full of wisdom for anyone who’s ever wrestled with money, ambition, and purpose – frankly for all of us. Here’s Rabbi Irwin Katsof.

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