One Thing Better

How to Tell Who Your Real Friends Are

Welcome to ​​One Thing Better​​. Each week, the editor in chief of Entrepreneur magazine (that’s me) shares one way to achieve a breakthrough at work — and build a career or company you love.


I broke up with a friend. Then I realized he was never a friend at all.

I’m telling you this because it represents something critical about relationships:

Sometimes, people have a relationship with you. But other times, they have a relationship with the chair you sit in.

Both are fine, so long as you know the difference. But we often don’t. We confuse what our relationships actually are, and that sets us up for severe disappointment.

I think a lot about this — because at this stage in my life, I’m prioritizing the first kind. So I’ve come up with a strategy to help filter for genuine connections, and I want to share it with you today.

But first, here’s that story about that friend…

The friend who wasn’t

A few years ago, I met a guy I’ll call Stuart.

He’s a founder and investor. We met at an event, had a nice conversation, and then met for coffee a month or so later. I have a broad network of people like this; I’m always interested in new friends I can learn from and grow with.

Then Stuart reached out with a request. His company was launching something, and he hoped Entrepreneur would write about it. I thought it might interest our readers, so I ran the story.

He was thrilled, and invited my wife and I over for dinner. He sent us a gift for the holidays. He’d text me every so often, just to check in. But he also asked for more coverage in Entrepreneur. Every few months, he had some new project to announce.

I started to think: Are we actually friends? Or has he just been buttering me up to get coverage?

In other words, does he care about me… or the chair that I sit in?

Let’s talk about The Chair

The Chair is the title you have, or the role you occupy. It is not yours. It remains in place. Someone sat in the chair before you, and someone will sit in that chair after you.

For example: I am the editor in chief of Entrepreneur magazine. But someone was EIC before, and someone will be EIC next. The title is a chair.

Intellectually, we all understand this about ourselves. But it’s easy to get lost in it.

My chair might be uniquely public, but we all have chairs in some way. Maybe you’re the doctor who everyone turns to for free medical advice. Or the well-networked person. Or the one with access to something or someone.

As a result, people want your attention. And if you mistake yourself for The Chair, you are in for a terrible letdown later. Friends of mine have sat in impressive chairs, and were showered with invitations and attention. Then they left and it all disappeared.

In the earlier part of my career, I didn’t care about this. I got swept up in the “status” of being a young magazine editor, who people wanted to wine and dine. I knew those relationships were transactional, and that was fine.

But now? Nah. I’m too old for that.

I’m happy to have transactional relationships during work hours. But if I’m going to invest real time and energy into someone, it needs to transcend The Chair.

So I’ve come to see my situation differently: I now have an opportunity to accumulate the right relationships, and build the right network, that will stay with me long after I leave The Chair behind.

Then I found a way to do it.

The Chair test

Let’s go back to Stuart, my hyper-engaged friend who kept asking for coverage.

One day, he texted me about a new product he’s launching. “Would you like to see the announcement?” she asked.

I decided it was time to test this relationship.

“As a friend, I’m always interested in all the great stuff you’re doing,” I texted back. “So I’d be happy to see it. But to set expectations, I’ve begun to actively discourage people from thinking of me as a path to coverage. It’s not where my own energy or excitement is, given all the other things I have going on.”

He replied: “No worries! Noted and I hope everything is going well.”

That was the last time I heard from him.

To be clear, I don’t begrudge Stuart for wanting press. But he disguised a transactional relationship as a personal friendship, and that didn’t feel good. I also don’t think it’s a wise way to connect with people.

But it did give me an idea…

Now, whenever I meet someone who I think could become an actual friend, I proactively take The Chair away. I do it casually. For example, when Entrepreneur comes up, I might mention that I no longer source stories myself. Or I’ll joke about how annoying it is to be pitched all the time (which is true).

Some people lose interest in me after that. Others aren’t bothered at all, because they’re not looking for coverage from me. Those are the ones I invest in.

How to win over people

Now, let’s flip this scenario.

What if you want to connect with someone, but they have a lot of status or are in high demand? What if they’re in their own chair?

The answer: Focus on them, not their position. Just tell yourself, “This is a regular person, who happens to be in this unusual role. So how can we connect as people?”

It is amazing what happens when you do that, as long as you’re truly genuine. It’s disarming. And it’ll stand out.

I once met a CEO for coffee, and he literally told me: “I will never ask you for coverage. I just think you seem cool, and wanted to meet up.” My guard instantly went down. We’ve since become very close.

The world is full of chairs. But the world is also an endless game of musical chairs. People sit down, they get up, they move around. Status won’t remain constant, but true human connection can. So make that the goal.

That’s how to do one thing better.


Join Megan Thee Stallion, Gary Vee, Robert Irvine… and me!

I’ll be emceeing (and am currently planning) ​an incredibly awesome event​ for Entrepreneur.

On October 23 in Brooklyn, I’ll be on stage with these legends — AND even better, the morning is dedicated entirely to solving your business problems.

Here’s how it works:

The personalized morning: We’ll put you in small groups of your peers, and you’ll all workshop a problem that’s holding your business back. Robert Irvine and I will move around the room, helping as well. You’ll make new friends, gain valuable insights, and leave with an action plan. Then there’s a VIP lunch.

The inspirational afternoon: I’ll talk on stage to Megan Thee Stallion and Gary Vaynerchuk, take your questions, and Robert and I will workshop more of your problems!

You can get tickets for the whole day, or just the afternoon.

Either way, ​use code JASON to get 20% off​. And if you come, please say hi! I’ll be around all day.

Make success simpler

Each week, you’ll get one new way to improve your work —
and build a career or company you love.