Is there life after fundraising? After 22 years working for Aish HaTorah, Rabbi Irwin Katsof decided to try his hand at finance so that he could be in a position to donate a million dollars himself to that and other worthy institutions. His new book, Living Dangerously: My Struggle to Get Rich Without Losing My Soul, tells the story of his ten-year roller coaster ride to find financial success. The Jewish Press spoke to Rabbi Katsof about his unusual journey.
Why did you think the story of your professional journey was important to share?
I wrote this book because I lived at the paradox at the heart of so many modern lives: the pursuit of material success while at the same time yearning for meaning. In the Jewish world in particular, I think it is a dilemma that they’re experiencing and going through as well.
For myself, after working two decades as a rabbi and a fundraiser, I jumped into the world of high finance, with the goal of becoming a philanthropist. I didn’t want to make a million dollars – I wanted to be able to give away a million dollars. But along the way, I lost touch with what’s really important. And I think that’s a story that’s important to share because it’s a universal one. So many people today are driven to be successful and to make money, and they lose connection with themselves, with their wife, their children, with G-d, with Torah. So, for ten years I lived as a…tortured, compulsive, driven human being, and woe to anyone who got in my way. But at my lowest point, by the grace of G-d, I discovered the best of myself. I got back in touch.
This book is my attempt to tell the truth – not just about the deals and the drama, but about the toll on my life: spiritually, physically, emotionally. And it’s for anyone who’s ever asked, “Is it possible to be ambitious and still remain true to yourself?” My answer is yes, it is, but it takes honesty, courage, and starting over again and again many times.
The subtitle of your book is “My struggle to become rich without losing my soul.” What sort of danger to your soul are you referring to? Religious and ethical problems, or personal?
I was referring more to personal issues, and what I think I came out of it with – the lesson is that what’s of essential importance to me is staying connected with my wife, my children, my family, and of course, connected to G-d.
We say that your soul whispers before it screams. You have to pay attention to the signs. Is there tension in your marriage? Is there anxiety, or feelings that won’t go away? Are there compromises that make you flinch? These are small things, but they’re signals – signals that you’re out of sync, ambition disconnected from purpose. An important tool for me is to ask “Where am I misaligned?” or “Where am I off target?”
If you don’t define success, the world will define it for you… Many people chase money. They chase fame. They chase titles – only to find themselves empty. So, I think a very important tool is to know what success means to your soul, not just to your ego. There’s nothing wrong with being rich in Jewish thought. Money is power. Money allows you to do good in the world. But you need to know what success means to your soul, not just to your ego… Does success include time with your family? Does success include integrity with work?
At one point, you compare your absence in your children’s lives to your father’s absence in yours. Before you became a parent, how did you envision your relationship with your children?
I got caught up in success and success came before everything. I missed my son’s high school graduation. I missed birthday parties. I missed dinner with the family. Success became the primary goal and that was a mistake. I think an important tool – and this is from a Torah perspective – is to anchor yourself daily. You can move fast but you don’t want to drift. The faster you rise, the easier it is to lose your center.
What was your process writing this book? Did you write it sequentially?
I wrote three books before. One with Larry King from CNN called Powerful Prayers: Conversations on Faith, Life, and the Human Spirit. We interviewed a hundred famous people about prayer and spirituality. I wrote a book called Words Can Heal about lashon hara; and I wrote a book called Five Steps on How to Get Your Prayers Answered. I did not set out to write another book, but this book is really my personal journal. I think that’s why it’s so vulnerable and honest and open, because I wasn’t censoring it as I was writing. I wasn’t thinking “How will this sound to someone?” I wrote it for me, as a way to keep me anchored and grounded during my business day… I would get back on the plane or in the car after a meeting and – at that time, everyone used a Blackberry – just start typing away with my thumbs on my Blackberry.
So, this book is adapted from those journals you took during the ten years that it covers?
It was written over ten years…between 2005 and 2015, and I just left it online and saved it.
Around 2020, I took it out again and started rereading it and I said, “You know what? There is a beautiful story here.” There’s a very powerful message and also a lot of very interesting subjects. It’s a business memoir, but it’s more than that – it’s also a self-help book and it’s also a spiritual journey. I sent it to my editor who had worked on my previous books with me, Uriela Sagiv (she actually was Kirk Douglas’s editor), and she read it and she said, “Irwin, you have a beautiful book here. This is really a powerful story, but every story needs an arc: a beginning, a middle, and an end. You have the beginning, you have the middle, but we need you to write the end.” And so, I went back and sat down and started writing again.
But most of it, which is how it is so detailed, was written at the time. It was written for me – when I’m writing about how I’m feeling miserable, I’m feeling broken, I’m feeling sad, I’m devastated, I wasn’t writing for anyone else. It was genuinely how I was feeling. [Publishing this book] required a decision – am I prepared to be so vulnerable and put my life out there for anyone to read? But I think what makes it such an impactful and powerful story is that it’s honest and vulnerable… If I summarize a kind of mantra of the story, it’s that in Judaism, there is nothing wrong with success. There’s nothing wrong with having money and wealth, right? It’s a tool to do a lot of good in the world. [But the message is:] “I’ll pursue success without losing my soul. I will build but not forget who I am. I will rise and still stay rooted.”
You mention that your first taste with riches happened during the dot-com bubble in the 90s. How did that happen?
My first taste of real wealth came during the dot-com boom. After years in nonprofit and outreach work, I suddenly found myself in the middle of a financial gold rush. Tech companies and venture capital were exploding, and I was helping to connect capital with opportunity. Practically overnight, the money started flowing in – far beyond anything I had ever experienced. It was intoxicating, but it also marked the beginning of my struggle: learning that while money can come quickly, staying grounded in your values and relationships is much harder. Several friends of mine whom I had known when I served as a rabbi took me into their deals as a gesture of friendship for my many years of service to the Jewish community, and this led to me being in the right place at the right time
What sort of things do you take into account when you present Orthodox Judaism to outsiders, whether irreligious Jews or Gentiles, both in your time at Aish and the business world?
That was always one of my goals, going back to my days at Aish HaTorah. I always emphasize that Torah has such amazing, powerful wisdom. But in today’s marketplace, in many ways, we’re missing the mark by not packaging and presenting it in a way that individuals can relate to. There’s so much competition in the marketplace of ideas…
I was attacked for writing a book with Larry King. They said he’s intermarried (he was Jewish), he was married eight times to seven different women – how can he represent Judaism? But if Larry King, an atheist, will go interview a hundred people about spirituality and prayer and miracles in their lives and insights they’ve received from G-d, people are likely to pick that up and read it. That’s why I pursued Larry to write a book about prayer… To get a master interviewer who is a secular Jew to write about prayer and belief in G-d, I’m going to get a lot of people to buy that book that wouldn’t normally buy a book about prayer. I think my guidepost is: “How do I expose the concepts of Judaism to people that normally won’t read them?”
Why do you think so many people were willing to help a fundraiser with no financial background become a Wall Street wolf?
I write in the book that everyone has to have a BHAG – a Big, Hairy, Audacious Goal. That’s something I learned from one of my mentors from my days at Aish, a gentleman named Leibel Rudolph, originally named Lou Rudolph. He was a Hollywood producer who left because he didn’t want to produce schmutz anymore. He came and worked with me, changing to his Hebrew name. He taught me the importance of really thinking big. When we were doing our international satellite broadcast called Help Our People Know, which was about the problems with Jews in the former Soviet Union (that’s how I met Larry [King]), he said we have to put pictures of who we want on our computer and look at them each morning. He said “let’s get Jeffrey Katzenberg, who’s head of DreamWorks, with Steven Spielberg and Sumner Redstone, who owned Paramount Studios – let’s get them involved with us.” And, sure enough, a couple of months later, we did. So, he taught me to think big. And I think if you’re going to succeed in anything, you have to believe that everything is possible, especially if you have G-d on your side. The Almighty can make anything happen.
You mention that it was difficult to find time for Torah study and tefillah in the midst of a busy schedule. Have things become easier in the last twenty years, as your routine has settled and ambitions refocused?
Yes. I now make time for what is important. I am able to identify my priorities and schedule accordingly. I have taken back control over my life.
What do you hope people take away from reading your book?
I hope readers see that success without soul isn’t really success at all. The book is about learning to pursue ambition and wealth without losing your values, your family, or yourself in the process. If my story can help someone pause, reflect, and realign their drive for achievement with their deeper purpose, then the book has done its job. I want readers to remember that true success isn’t just what you build, but who you become in the process