Before becoming an investor and businessman, Katsof spent 25 years as a fundraising powerhouse for Aish HaTorah and was ordained as a rabbi. He is also the author of three previous books, including How to Get Your Prayers Answered, first published in 2000 and reissued in 2002. Today, he serves as president of Trademissions.org, an organization that helps U.S. fund managers raise capital abroad.

In trying to find a word that captured the boldness of Katsof’s career journey, I discovered that he had already supplied the best description himself: BHAG — Big, Hairy, Audacious Goals.

Living Dangerously was written over a decade, shaped by both triumph and turmoil. Drawn in by the deeply personal tone of the book, I was grateful for the opportunity to ask Katsof a few questions. What follows are excerpts from his thoughtful responses.

Why did you write this book?

"I wrote this book as a deeply personal reflection on the spiritual and psychological cost of chasing success in the business world after leaving 25 years of Jewish outreach work.

It began as a journal during a time of inner crisis, when I realized that my pursuit of wealth, fame, and validation was creating a growing disconnection from my soul.

I wanted to tell the truth, not a curated success story, but a raw, honest account of what it means to lose your spiritual center while building a "successful' life.

The book is also a form of teshuvah — not just in the religious sense, but as a soul-turning. I wanted to bring my experience full circle: from purpose, to exile, and back to purpose again."

What would you add or change now?

"I’d expand more on the psychological toll of compartmentalization — the way I kept business and spirituality separate, and the cost of that split.

I’d speak more directly to the Jewish businessman or community leader who secretly wonders if they’ve sacrificed too much of their inner life on the altar of achievement.

I might also add stories of hope and repair — moments where I’ve helped others reconnect to their soul purpose after reading the book or hearing my story. Finally, I’d underscore that this isn’t just my story. It’s a generational one — about Jews raised in a secular world who later awaken to a hunger for something deeper, more rooted, more holy."

What stands out most from your years at Aish HaTorah?

"It’s the people. Watching someone walk into Aish disconnected, unsure, maybe even cynical, and slowly begin to discover their soul — that never stopped moving me. It was like witnessing a spiritual birth.

But even deeper than that was the mission. We weren’t just running a kiruv organization — we were soldiers on the front lines of Jewish history. Rabbi Weinberg instilled in us the belief that the Jewish people were in crisis, and it was our responsibility to respond. That urgency, that clarity of purpose, gave my life structure, meaning, and fire."

The book is filled with stories of meetings with prominent figures — presidents, kings, business moguls, and politicians — so much so that an index would have been helpful for readers wanting to revisit specific names and encounters.

I asked Katsof to name three of the most impressive people he had met. His answers say much about his values:

• John Ashcroft, for his spiritual integrity in public service.

"Ashcroft carried his faith into every aspect of his life. He wasn’t performing — he listened, engaged, and treated each moment as sacred. To see humility instead of ego in someone at the top of the U.S. justice system left a deep impression."

• Lady Margaret Thatcher, for her moral clarity and strength.

"She embodied both conviction and compassion. One little-known story is how, during WWII, her family took in Jewish refugee children from Nazi Europe as part of the Kindertransport. That personal history of moral action made her legacy resonate even more for me."

• Rabbi Noah Weinberg zt”l, the founder of Aish HaTorah.

"He reignited the flame of a generation. He didn’t just teach Torah — he challenged young Jews to lead, to take responsibility for the Jewish future. He helped me understand that faith wasn’t a leap of blind belief, but a rational, meaningful foundation for life."

Katsof also writes candidly about his high-stakes business ventures in Eastern Europe and the U.S., including some audacious (and at times risky) financial schemes. His goal was to be able to give money to good causes, not just to ask for it. 

Yet the true message of Living Dangerously lies in the deeper spiritual and moral lessons, especially for young, ambitious Jews navigating the tensions between faith and material success.

"If there’s one thing I’ve learned," Katsof writes, "it’s this: You can chase the world and still lose yourself — but if you stay true to your soul, you’ll never be lost, no matter where you end up. Success without meaning is a trap, but struggle in the service of truth is sacred. I wrote this book so others wouldn’t have to lose their way to find their purpose — but if you have, you can always come home."

Katsof divides his time between Rockland County, New York, and Jerusalem, Israel. He has been married to Judy for 42 years and is the proud father of eight children and grandfather to twenty-five.

Living Dangerously
By Irwin Gabriel Katsof
434 pages | Beverly House Press, 2024
ISBN: 979-1-957-4661546615-6
Contact: Estie@EDPressSolutions.com
Publisher: BeverlyHousePress.com