By the time Ben Woolf was 14, the future he could see for himself felt like a trap.

He was raised amid tension rather than tranquility, his early years fraught with frequent parental conflict. Family life was unsettled. Happy childhood memories were rare.

His mother was Israeli and his father had been a lone soldier in the IDF, yet Jewish identity in the home was mostly absent. “I didn’t get much, or any, Yiddishkeit,” he offered without bitterness.

Years later, he said, his parents changed, and so did he. “I’m over it,” he said. “It’s not a limitation.”

The first turning point in Woolf’s story came early – and hard: a violent night ending with his arm through a glass door and stitches in a hospital on Christmas Eve, a day his marginally Jewish family celebrated as family time. Lying awake, alone in the hospital bed, he made a bargain with God. If life could be different, he was ready to do whatever it would take to become the kind of person who escapes the smallness of the world he had known until then.
At first, he thought the answer was money.

In high school, he worked two jobs, partially to earn money for clothes and social life, but mostly for the bigger idea: escape. After graduation, he worked for a UK bank and leaned into a simple equation: Wealth meant stability; stability meant a better life; a better life meant becoming someone else entirely.

It wasn’t only comfort he wanted. He also wanted distance from what he’d seen around him: friends who turned cruel, including an incident where they harassed a homeless man. He didn’t have the language for values at the time. He just knew he didn’t want to be that kind of person.

At university, he encountered a Jewish man who spoke with a seriousness Woolf found magnetic. For the first time in his life, he met someone who talked about ideas without mocking them. He described a specific hunger: not only for community but for a world where ambition and thought were treated with dignity.

That hunger led him to ask his mother, “Where do I find Jewish people?”

Then another door opened: a Jewish man who noticed him sitting alone and went over to him over to talk. It was a small kindness with outsized consequences.

That conversation introduced Woolf to the international Jewish fraternity Alpha Epsilon Pi (AEPi). Soon, he was moving in organizational circles, helping build chapters in multiple countries and gaining momentum.

Through AEPi, Woolf was taken under the wing of a wealthy man. Suddenly, he had proximity to donors, big conferences, and private rooms where decisions were made. He found himself backstage in the Jewish philanthropic world, watching power move through back elevators and guarded corridors.

From AEPi, he helped launch Kahal Abroad, a major study-abroad clearinghouse that connects Jewish students across countries and cities. He traveled widely and visited art, history, and Jewish museums in dozens of cities, building a personal education in global Jewry. A decade later, Kahal Abroad was taken over by the Joint Distribution Committee.

Then came the pivot to the for-profit world: a tech start-up, built with a friend from Meta, aimed at something deceptively simple: an online game store meant to improve how people find games they love. It gained hundreds of thousands of users, but it failed anyway.

Before his company failed, Woolf was invited to a large conference. He was nudged toward donors who might help his business. He asked to meet the biggest funder in the room. After dinner, he finally got the philanthropist’s attention, almost accidentally, after being told he was sitting in the man’s seat.

When Woolf pitched his dream, the philanthropist asked him a question that shifted the conversation from finance to faith: “Do you believe in God?”

Although he didn’t keep Shabbat and didn’t look religious, Woolf said yes, he did believe in God. And he was reading a page of Torah a day.

The philanthropist’s response was not a check or an introduction. It was a discipline: a WhatsApp group. Every day, Woolf was instructed to send a message summarizing his daily page of Torah, including what he thought and any questions he had. Woolf sent these daily WhatsApp messages for six months.

Meanwhile, the tech start-up failed. After years of highs, he fell into a short, blunt depression. Back at his parents’ home, the trajectory felt broken. Nevertheless, he continued reading a daily page of Torah.

When he was back in the US, he reached out to his philanthropist mentor and asked to visit him. Unknowingly, he had asked to be hosted over Shavuot.

A rabbi called him, alarmed. Shavuot wasn’t just “cheesecake until 6 a.m.” It was receiving the Torah; it was also, that particular year, a long stretch of yom tov and Shabbat with a religious family.

He went anyway.

It was not his first Shabbat experience, though earlier ones had been sour, which included a host in the UK who mocked his clothes. But this time was different. He stayed up studying. He met people. He watched a home built around Torah and hospitality rather than anxiety.

Woolf had long hair then, pushed back off his face, still visibly between worlds.

And in the middle of the traffic of visitors and conversations, he asked for half an hour alone in the philanthropist’s office.

“I hit rock bottom,” Woolf told him. “I don’t have any choices. I don’t know what my choices are.”

The philanthropist introduced him to a two-week program at Machon Yaakov in Jerusalem. Woolf was unimpressed by the website, but the man insisted.

Just 24 hours after keeping Shabbat and Shavuot for the first time, Woolf was on his way to Israel. The message that really made an impression was that “Shabbat is a pause.”

“I resonated with that because I had worked all the time.” Working all the time had been what he thought was the key to success.

“To hear that Shabbat is a pause felt like a relief. God said that I can have a pause. If He’s greater than everything in the entire existence, then what is there to be scared of?”

After two weeks immersed in the yeshiva program, he returned to the rat race. But his vision had shifted. Now he understood that the goal was to figure out how to achieve financial success while maintaining a healthy family.

So he begged the yeshiva’s head to let him come back and learn how to keep Shabbat. Woolf originally planned to stay in yeshiva for three months. “I ended up staying for two years. I really enjoyed it. It changed my life. There were so many things I needed to know. It answered so many questions. To hear it and see the sources made such a difference.”

After yeshiva, he was committed to Shabbat observance and keeping kosher. He went back to work, enrolled in an MBA program, but also made time for dating.

“I had way more balance,” he said. “I could still do a lot, but my intentions were focused. I wanted to get married.”

As part of his MBA program, he spent a Shabbat in Germany, walking 90 minutes to the event hall from his hotel, reciting “Kiddush,” and praying by himself. Shortly after that Shabbat, Woolf met his future wife, Marni. He was building a new life for himself.

The next stage was becoming an entrepreneur. In 2025, Woolf established Promise State (promisestate.com), a high-quality clothing line featuring a minimalist silhouette of Israel as its signature mark, integrated seamlessly into the design.

Now a married father and entrepreneur, at 34, Woolf still dreams of setting up new businesses. Meanwhile, he reflects on the benefits of a life in Israel.

“Israel is the only place you can comfortably be the kind of Jew you wish to be.

“I work from home. The weather is always good. We have friends in multiple communities. My wife’s family is here. I get to work and spend my time with them in beautiful weather.”

Woolf has healed many of the traumas of his childhood and repaired relationships with his family. He retains warm feelings for England and, along with his wife and son, visits regularly.

Making aliyah the way he did was harder than expected. But he noted that “the challenges are balanced by positives.”

Ben Woolf, 34
From Southend-on-Sea, England
to Jerusalem, 2020