What a Hedge Fund Billionaire Taught Me About Leadership

Before law school, I worked as the executive assistant to a hedge fund billionaire. That meant sitting next to him on the trading floor 10 hours a day, five days a week.

He was one of the most ethical and intelligent people I’ve ever worked with — and from him, I learned a lot about how to run a business the right way.

One of the biggest lessons?
Hire the right people. Give them the right tools. And then let them do their job.

Here’s how I learned that the hard way:

One year, I was in charge of coordinating our annual holiday card mailing — a massive project. The year before, we’d brought in a temp to help with the workload, and I assumed we’d do the same.

But the firm had just hired its first-ever Head of HR. One of her big goals? Reduce unnecessary expenses. When I submitted the request for temp support, she denied it.

I was a little surprised. Honestly, I expected my boss might overrule her.

He didn’t.

At first, I was frustrated. But then I realized exactly what he was doing — and it made total sense.

You don’t hire someone, ask them to lead, and then undermine their authority every time a decision gets made. That’s not leadership. That’s micromanagement.

He had empowered her to do her job, and he respected her decision — even if it meant a little more work for me in the short term.

And you know what? I got through the holiday season just fine.

And I carried that lesson with me into my own leadership.

Today, when I hire someone, I do exactly what he did:

✅ Hire people I trust
✅ Give them what they need
✅ And then get out of their way

Because great leadership isn’t about doing everything yourself.
It’s about building a team you trust — and then letting them lead.