What Billionaires Taught Me

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May 10, 2026

4 min read

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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.

1. Success Is Never a Straight Line

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.

2. Failure Is Part of Success

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.

3. Your Lowest Moments Can Become Your Greatest Assets

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.

4. Being Jewish Means Responsibility

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.

5. The People Around You Shape Your Future

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.

6. Money Creates Opportunity, Not Happiness

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.

7. Your Definition of Success Will Change

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.

8. Giving Is an Investment, Not Just an Obligation

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.

9. Shabbat Creates What Success Cannot

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.

10. The Greatest Investment Is Your Children

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.

Final Thought

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.

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