Irwin Katsof’s book Living Dangerously: My Struggle To Get Rich Without Losing My Soul intrigues, astonishes, and inspires. As does the news of his latest venture, an AI tool as a companion to his book, called Living Dangerously the Companion, aimed at dealing with personal and ethical dilemmas. The book leads the reader to ask, “What can I take from this to improve my life?”
At age 24, Katsof was backpacking through Europe. The year was 1979.
He ended up at Aish HaTorah in Jerusalem’s Old City for the High Holy Days, where he was deeply impacted by the classes of Rabbi Noah Weinberg. Within a year, he had become a ba’al teshuva (Jew from a secular background who becomes religiously observant).
“I started slowly, but by the end of the year I was fully committed to the Torah path,” he writes in Living Dangerously.
Three years later, he met his “sensitive and brilliant” future wife, Judy.
Katsof was sent by Aish HaTorah to Los Angeles to organize its first fundraising banquet, which led to his opening an Aish branch in LA. He proposed to Judy on the phone so that he could sign the lease on an apartment that included her name. This bold move became the hallmark of his attitude in fundraising and later in business.
For more than two decades, Katsof was successful in bringing many potential donors, such as business leaders, politicians, and Hollywood stars, to Aish in Jerusalem. He became the executive director of Aish’s Jerusalem Fund. He also became an ordained rabbi and teacher and was successful in reaching out to Jews of different ages seeking meaningful Judaism.
One mission was led by Larry King, with whom he wrote the book Powerful Prayers. They were hosted by King Hussein of Jordan. In the book, Katsof describes running through the palace grounds with a present for the king and almost getting shot by the palace guards.
He writes how he “recruited Jason Alexander to participate in the Aish Discovery program and met with Jerry Seinfeld about our Words Can Heal program.” He spoke to refuseniks in the Soviet Union and launched the program Help Our People Know while he was in LA “to raise public awareness about the plight of Soviet Jews.”
Wealthy enough to donate
After 22 years, Katsof decided that rather than asking others for donations, he would become wealthy enough to donate money, setting for himself the goal of giving away $1 million annually.
Rabbi Noah Weinberg had been a massive influence on Katsof’s life. When he consulted with the rabbi regarding his new plan to become successful in business, Rav Noah gave his blessing, saying, “Don’t forget why you are doing it… Feel [the Almighty’s] pain at the suffering of His children… and ask yourself what you can do to help them.”
“As of January 1, 2005,” Katsof writes in Living Dangerously, “I was self-employed.”
As a budding entrepreneur, he was devoted to giving tzedakah (charity). He met Rabbi Zilberman in the Old City who has a yeshiva and arranges tzedakah for poor families. Katsof continued the relationship with him throughout the years, and the rabbi continued to pray for his success. They even wrote a contract. The document ended with the words: “God will bless you from Zion, and you will see the good of Jerusalem your whole life – you, your children, and the children of your children and all Israel.”
Nevertheless, Katsof quickly discovered that making money in business was not an easy road and that “to meet my goal of giving away $1 million a year, I would have to be making $5 million, after taxes.”
He reached out to a friend, whom he calls only “Paul,” who became a close financial adviser. He took out loans on his home from various funds and from friends and family. His deals and attempted deals that did not work out were in the US, Eastern Europe, Russia, and elsewhere.
His stories are hair-raising, such as fear of arrest in Moscow. Months of work can result in nothing. At other times, he succeeds (with God’s help, he is always aware). He travels to Odesa, Barcelona, Nepal, Singapore, Abu Dhabi... the list goes on.
His financial escapades read like a thriller, a roller coaster of uncertainty, with fear of bankruptcy and exuberance at successes. There are stories of intrigue, obfuscation, and distrust. The political situation in various countries is often precarious, and occasionally a deal that collapses turns out to be a blessing in disguise.
Everything comes from God
Katsof is always aware that anything he has comes from God and believes that only if he behaves in a way that is in line with following the Torah and mitzvot (commandments) will God smile on him and his ventures. He struggles with setting aside time for Torah study and for praying in a minyan (quorum of 10). He writes, “We cannot often see God’s presence… but in hindsight… His role is suddenly all too clear.”
In his book, he describes meeting with US presidents and European and Israeli prime ministers. He works on projects that he hopes will improve the world.
Oligarchs from Kazakhstan hired him to establish the Global Foundation for Democracy; he organized the first Global Conference in Geneva for them with 15 former world leaders and diplomats. He also became involved in renewable energy in 2017.
In 2010, as director of America’s Voices in Israel, he brought the cast of the hit TV show House to Israel, and one of its stars, Omar Epps, a Muslim, whom Katsof describes as “a deep, sensitive, and empathetic human,” became a close friend.
Katsof spoke to Rabbi Zilberman often, asking him, again, to pray for him. On some occasions, the rabbi gently asked him about his religious practice.
He became addicted to his BlackBerry and business ventures, severely reducing his quality time with his children and jeopardizing his marriage to a woman he adores and describes as his “rudder and anchor.” He recounts the anguish they went through; it was deep and painful.
We are let into his innermost pockets of pain, regret, and self-doubt as he describes how they try various therapies. Eventually, they find their way together.
Today, they live in Jerusalem, and he returns to America for part of the year. He is most proud when writing or speaking about his eight children – seven of whom live in Israel – and his 25 grandchildren. His children include a daughter in Florentine, Tel Aviv; and a son in Esh Kodesh in the Binyamin area, where he established the Settlers Wine winery. “They’re all very different. We let them know that we love them and believe in them no matter who they are, that they need to follow their own path.”
Eight tips for business
In Living Dangerously, Katsof lists eight tips for anyone thinking of going into business or finance. The first is: “Stay at your current job until you have at least 18 months of savings in the bank.”
When Irwin Katsof left Aish HaTorah and went into business, it was “overwhelming and frightening,” he told The Jerusalem Post. So, he found solace in writing a journal.
He began journaling his travels.
“When I was flying with a businessman in his private plane over Ukraine… or when I saw a group of blind and deaf children signing to each other at Ben-Gurion Airport and I wondered, ‘How does a blind and deaf person experience Manhattan?’ I’d get on the plane and start typing.
“I got perspective on what was happening in my life, and it wasn’t so overwhelming. I was just writing for me.”
Words from the heart
After being with Aish Torah for 25 years, where “every day was meaningful,” when Katsof went into business, he missed the sense of helping people. In 2012, after “beginning my own personal rebirth,” he went into therapy: Jungian analysis and Core Energetics. He thought, “There are powerful lessons here,” and he turned to his journal. He “cried many times, rereading it,” he said.
A self-defined “big believer” that “words that come from the heart enter the heart,” Katsof sent 30 blog entries to editor Uriela Obst Sagiv, a former journalist, Pulitzer nominee, and editor of an earlier Katsof book, who now lives in the Old City of Jerusalem. “She wrote me back, ‘Irwin, this is an absolutely beautiful story.’” She asked if he was sure he wanted to publish something so vulnerable. He replied, “It’s my story. And I think it’s so many people’s stories.”
“I learned from my journey to have a balanced lifestyle, not chase every pot of gold. God controls the world, and He will decide what’s going to happen,” he told the Post.
“I strive to have a sense of equanimity and peacefulness, which doesn’t mean that I don’t get anxious, but I allow myself to be with those feelings because that’s a part of being alive.”
He has trained in Core Energetics, trauma therapy, psychodrama, and more and has an MA in transpersonal psychology, with a specialty in applied spirituality.
“I have a lot of qualifications in the helping professions, and it’s something that I would like to do; I think that’s my next act.” He had his own TV show as a child, Katsof told the Post, and “would love to get back into theater.”
Currently, Katsof said, his “main work is assisting US companies and fund managers in raising capital.” He also carries out trade missions in partnership with the US Department of Commerce through his company Trademissions.org.
He is still in touch with Rabbi Zilberman and with most of his former business associates. Katsof gives tzedakah to the yeshiva world, to the needy in their community, and “to people who need to put food on the table.”
Katsof and his wife would like to help war widows who gave birth after their husbands fell in battle. “I owe everything to my wife because the wealth I have in my life now is my family… and it’s all because my wife saw my potential, understood that I was a little lost and caught up, but knew that I was a good man.”
Katsof considers that his “journey has been... connecting to my soul and to the Jewish people and to God so that I’m never really alone, and I can deal with anything that happens…”
The writer, an award-winning journalist and theater director, is editor-in-chief of WholeFamily.com. Her latest production is Heroines! Songs and Soliloquies for the Soul.