Are you guys hanging out without me?

Are you guys hanging out without me?

A strange thing happened when my business took off:

My social life started sucking.

It happened slowly over a few years.

I used to get invited out constantly.

Dinners. Drinks. Parties. Random nights out with friends.

But as my life changed alongside my business, the invitations almost completely stopped.

I was confused.

Did people think I was busy?

Or was it worse? Did they think that I had changed? Or maybe that I would judge them?

When I thought about it, I kind of got it.

I related to the feeling: when I considered someone to be different from me, especially when I couldn't relate to their life, I othered them without thinking about it.

I'd visit their big, fancy house and think:

1. I don't want them to see my much more modest house.
2. I'll feel intimidated and stressed out if they're around.
3. They're on a different level—they wouldn't want to hang out with me and my friends.

Ironically, one of the key reasons I wanted to be successful in the first place was because I thought success would result in an amazing social life.

It was the subconscious loop driving me in my twenties:

Be successful + get money = an incredible life (friends/travel/parties/romantic partners/etc).

When I was young, I thought money was a backstage pass to all the good stuff.

That one day I'd get all the stuff, the bank account, and the recognition, and then suddenly life would be like an episode of Entourage.

But that's not how it works.

Ironically, money makes that harder.

The worst part: the things that make your social life wonderful (friends, community, group activities, etc.) are available for free, with a little effort.

Money actually distances you from others and makes it harder to connect.

It makes you unrelatable.

Even if the person inside hasn't changed, the outside has, according to everyone else.

You're viewed as different. Other. Out of touch.

To use an analogy:

If all your friends drive Volkswagens and one day you roll up in a Mercedes, it shifts things in an odd way.

You just bought this new car. You're really proud and excited about it.

You want to tell your friends about it, and how you worked so hard to get it.

But doing so twists everything in knots. Suddenly they're making comments to one another:

"God, would she stop talking about the Mercedes? We get it!"

"Little miss fancy…"

You've othered yourself.

That's what money and success do to your social life, in a nutshell.

I recently read Lena Dunham's (seriously excellent) new memoir, Famesick and when she described her own version of this, what I had felt for years clicked.

As her TV show Girls became a hit, the world knew her name, but the people who actually knew her, her real friends, stopped calling.

Old invitations went away.

Friends assumed the acclaim, money, and famous boyfriend meant she had everything handled.

And worst of all, she couldn't complain without sounding ungrateful.

Then someone gave her the bleakest definition of success I have ever heard:

"You know you've made it in this town when your phone stops ringing."

Later, she admits: "The fact is, I still wanted my phone to ring."

A few years ago, a friend of mine hit it big on a business deal and made tens of millions of dollars.

At the time, he lived in a beautiful character home in a wonderful middle-class neighbourhood full of kids, and he was friends with all his neighbours.

Socially, he had it made, with a tight-knit friend group and community.

He loved his life. But he also loved cars. And he wanted to buy a Porsche.

I grabbed him by the lapels and told him not to do it.

In fact, I went one step further. I told him to change nothing and tell no one.

Don't buy the new car. Don't renovate your house. Don't talk about your big win.

Otherwise, I worried he'd lose the community he loved and become an unrelatable alien.

Even something as subtle as a sparkling new car in the driveway can completely change how people see you.

I've witnessed this repeatedly: if you want to be liked, don't upgrade your lifestyle.

Otherwise, best case, you get fewer invites.

Worst case, you create envy and jealousy and people hate you.

The awkward part is that nobody has to say anything.

A different house, a different car, different clothing—small visible changes can make people feel you now live in a world they cannot enter.

This is the great irony: you want to make money and turn it into the awesome life you want.

And getting that awesome life—at least its physical manifestation that others can see—distances you from the very people you want to share it with.

Before you throw tomatoes at me, yes, I know.

Warm up the world's tiniest violin for me and Lena. First world problems.

But that is part of the issue.

Once your problem becomes enviable, you lose the right to talk about them.

So what do you do? You end up hanging out with other wealthy people, because they are the only ones you can share problems with.

Which then makes you even more out of touch.

Success builds this weird glass wall around you.

The people you want to see stop calling, while the awful ones call constantly because they want money, an introduction, a job, or an investment.

Deal friends, not real friends.

You end up knowing more people but having fewer deep friendships.

In reality, you don't want to be rich. You want to be rich in friendship.

I know, barf. But seriously.

My friend Morgan Housel has a great line on this:

"You might think you want an expensive car, a fancy watch, and a huge house. But I'm telling you, you don't. What you want is respect and admiration from other people, and you think having expensive stuff will bring it. It almost never does — especially from the people you want to respect and admire you."

For the last few years, I've been obsessed with this idea and trying to revitalize my social life. As a result, I've been studying people like my pal Nick Gray, who focus their lives on building community and deep friendships.

I know many people who are much wealthier than Nick (although Nick is also an extremely successful entrepreneur and investor) that would trade their wealth for the rich friendships that he has.

Once I learned how Nick runs his social life (check out my interview with him about this), I set about turning my life into a series of non-negotiable friend-related rituals/habits where status and money were out of the picture.

I play pickleball with the same group 3-4x a week.

I run five monthly forum groups (basically group therapy) with 6–8 awesome guys in each, with a structure that creates insane depth (preparation, Nonviolent Communication, extreme confidentiality).

I started Entrepreneurs Lunch Club, where I rent out a restaurant once a month and get a few dozen amazing local entrepreneurs together to chat over lunch. The one and only rule: no bragging or small talk allowed.

I host annual events like Think Week, Interesting People, and Conglomerateurs, where I get friends, new and old, together to get to know one another.

After last year's Interesting People, I felt like I'd done MDMA for days.

I got messages from almost everyone who came.

Not obligatory texts.

Long, emotional messages about people they had met and conversations they were still thinking about.

That was when the new scoreboard clicked for me.

I used to think becoming rich and successful was the goal.

Now I think about how many people really know me and like me as a person.

Not the impressive ones. The people I actually like, and who care about me back.

People who know my inner world, and would let me sleep in their basement if my house burned down.

Real friends, not deal friends.

Friend Rich.

Sure, being Money Rich has its perks.

Don't get me wrong: you should strive to buy yourself some freedom. But you don't need to tell everyone about it.

Instead, you should focus on becoming Friend Rich. It's much more enjoyable, and it satisfies our caveman brains in a profound way.

Think about it, if it was 10,000 years ago, who would you want to be in your village: the person who obsessively gathers and hoards nuts, or the one who tells the best stories, surrounded by laughing friends at the fire?

Who do you think would feel safer? The one with all the nuts (who everyone might come beat up if they were hungry) or the one who was beloved by everyone?

So, if your own phone has gone quiet, whether it's due to your fancy new car or simply because you've been too busy to get your friends together, don't wait.

Think about who you really want to spend time with.

The ones who can't do anything for you. Who are just flat out awesome people.

Maybe put some conversation prompt cards on the table to make things interesting (I love these ones).

Build it into a ritual.

Become the person who makes things happen.

It's so much better than having all the nuts.