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10 lessons on failure, purpose, and being Jewish.
I’ve had the privilege, through the Olami Mentorship network, to sit across from some of the most successful professionals in the Jewish world. Tech tycoons, real estate moguls, healthcare magnates, individuals who have built fortunes and influence at the highest levels.
These conversations are not just interviews. They are a window into something much larger: a global mentorship network where accomplished Jewish professionals invest their time, wisdom, and experience into guiding students and young professionals in a structured, ongoing, and deeply personal manner.
Their stories could not be more different. Yet once the conversations begin, the same truths keep surfacing.
Their stories couldn't be more different, but once the conversations started, the same truths kept showing up.
Here are the 10 core lessons I’ve learned from them.
I asked everyone the same question: Was your journey a straight line?
Without exception, the answer was no.
Behind every success story is a path filled with detours, uncertainty, and unexpected turns. The straight line we imagine simply doesn’t exist.
Failure isn’t something that happens instead of success. It’s something that happens within it.
The people who have built meaningful lives don’t just tolerate failure, they credit it. The setbacks, the wrong decisions, the moments things fall apart, those are often what sharpen judgment and build the resilience that success requires.
What stood out most was how they defined their greatest moments of difficulty.
The valleys weren’t described as obstacles but as stepping stones. The moments that felt like they were falling behind were often the ones that moved them forward.
Every person I spoke to expressed pride in being Jewish. But more than identity, they spoke about responsibility: to care about others, to feel another person’s pain, to celebrate someone else’s success, to take responsibility for the collective.
For them, being Jewish is not just who you are. It’s how you live.
When it came to building teams, one theme kept repeating: Talent and experience matters, but what matters most is character, work ethic, drive, and ownership.
Many of them said they listen closely to the kinds of questions people ask. Are they focused on what they’ll get, or on how they can contribute?
That distinction often reveals everything.
When I asked what makes them happy, very few spoke about money.
They spoke about family, relationships, meaning.
Money opens doors and creates options. But it does not, on its own, create fulfillment.
Early on, success is personal. It’s about building something, creating stability, and providing for a family.
But over time, that definition expands. It becomes about your company, your employees, the culture you’re building.
And eventually, for many, it becomes about something even larger. It becomes about the Jewish people.
The way they approach philanthropy is striking. They don’t just give, they build.
They look for vision, leadership, responsibility, and impact. They want to know their contribution will matter.
But one insight stood out: “When you feel appreciated, it’s easier to give.”
Appreciation creates connection.
One piece of advice came up again and again: Bring Shabbat into your life.
Slow down, disconnect, be present.
Many described Shabbat not only as spiritual, but as protective. It strengthens families, deepens relationships, and creates balance in a world that never stops moving.
More than one person told me that their best investment wasn’t a company; it was their children. Specifically, giving them a strong Jewish education.
There’s no clear return on paper, but over time, they see it, in identity, values and direction.
And they consider it one of the most meaningful decisions they’ve ever made.
Success isn’t linear. Failure isn’t the enemy. Money isn’t the goal. People are.
And at some point, success stops being about what you build for yourself and starts becoming about what you build for others.
Baruch HaShem!!!!!!!
The lessons reflect great wisdom and I admire those who live by them. But
the ultimate lesson is the recognition is that G-D is in control. We're supposed
to put in the effort to succeed, but where it leads is not in our hands.
Others could have done the same things as the billionaires, but if G-D
had a different plan for them, they could have ended up poor. Thankfully,
the billionaires in the article appear to have used their wealth in a
positive way.
If these billionaires see Jewish education as being so important, maybe they could gigure out some way to lower costs for Jewish families so a Jewish school doesn't cost more than a Catholic school, and school fees are not an effective form of birth control for Jewishly committed couples who would like to have more urgently needed babies but can't afford to educate more.
I agree 100% re billionaires using their wealth to make Yeshiva affordable.
Life can be like a slingshot. The long retreat that can propel you forward. STAY Strong...
Amen!!!!