Then, unexpectedly, he turned to me and asked, “Do you know any big rabbis through your charity who could give me a brachah?” He was referring to Smach Zevulun, an organization I cofounded that creates authentic Yissachar-Zevulun partnerships between businessmen and talmidei chachamim in Eretz Yisrael.

This request was completely out of character, as asking for a brachah from a rav isn’t the norm in his circles.

“I’ll get you a brachah from a gadol if you commit to a Yissachar-Zevulun partnership,” I joked. I was sure he’d brush it off, but to my surprise, he replied, “If a deal closes in the next 30 days, I’ll sign up.”

“What’s the likelihood of a deal in that time frame?” I asked.

“Slim to none,” Josh admitted.

“I’ll work on it,” I said.

Later that day, I called a family member of Rav Avigdor Nebenzahl, the world-renowned posek and former rav of the Old City. He is also the senior rosh yeshivah at Netiv Aryeh, where I learned more than a decade ago. I explained how many Jews were invested in this entrepreneur’s business and how it could be an amazing opportunity to bring him closer to Yiddishkeit and Torah.

“This is his Hebrew name,” I said, and I rattled if off. “Can you please share it with the Rav, so he can daven for his success?”

Three days later, Josh called me, ecstatic.

“Out of nowhere, the CEO of a billion-dollar retailer emailed me asking for a contract — even though we were only early in the sales process with his company,” he shared.

Within the next 24 hours, the multiyear, multimillion-dollar deal was signed with an initial contract for $500,000 for the first year. Minutes later, Josh called to share the news. While he was excitedly telling me about the contract, another call beeped in — from my friend. I put Josh on hold to answer.

“I just left the Rav’s home, and he gave a warm brachah that a deal should go through, and that Josh should have the zechus to do a Yissachar-Zevulun partnership.”

At the very moment Rav Nebenzahl gave his brachah, the CEO of the billion-dollar retailer had signed the deal.

I switched back to Josh to share the news. He was in shock; just a few days prior, this deal had been no more than a pipe dream.

Last week, Josh followed through on his commitment and signed a Yissachar-Zevulun shtar with a rosh kollel and posek in Yerushalayim. Together, they are building an authentic relationship and earning eternal zechus in this world and the next. And for me, the takeaway was clear. If you go beyond your comfort zone for Hashem, He responds in the most unexpected ways.

Jordan Odinsky is the cofounder of Smach Zevulun and a partner at Ground Up Ventures, an early-stage venture capital firm.

(Originally featured in Mishpacha, Issue 1943)