How to Sit With Billionaires

“A billionaire once told me: When you’re stuck, go sit in the most expensive hotel in your city. Order one coffee. Watch, Observe, Listen and Learn… You will begin to know what makes the real difference in success… It works every time.”

I love this idea because I’ve been doing some version of it for years.

I intentionally put myself in rooms with people who are doing extraordinary things. Sometimes those rooms have included billionaires and incredibly successful business owners. Other times I’ve been around some of the best military teams and operators in the world, NFL teams and professional athletes, remarkable spiritual leaders, coaches and people who are simply operating at an incredibly high level in some area of life.

And I want to make an important distinction. I haven’t simply been “around” these people. I’ve coached many of them. I’ve partnered with some of them in businesses and other endeavors. Some became clients. Some became colleagues and friends. Some simply crossed my path for a few hours and taught me something I still remember years later.

After decades of doing this, I’ve become convinced there is enormous power in proximity. Get close enough to excellence and you begin to see things you couldn’t see from a distance. Things that seem impossible from the outside often look very different once you get close enough to see how they’re actually done.

But there is another side to this that I think is just as important.

How do you get into those rooms without being overcome with Imposter Syndrome when you get there?

How do you sit across from the billionaire without suddenly becoming painfully aware of how much money you haven’t made? How do you work with an elite operator without feeling like you need to prove how tough you are? How do you sit with a professional athlete, CEO, general or spiritual leader without wondering whether you really belong there?

I think I’ve learned something about that too.

The secret to sitting comfortably with billionaires isn’t convincing yourself you’re as successful as they are. It’s knowing who you are, going there to learn, and knowing you have something to give.

That principle has allowed me to sit comfortably in almost any room.

You Can Compare or You Can Learn

I’ve walked into plenty of rooms where I could have compared myself to the people around me. This guy has more money than I do. That guy built a company bigger than anything I’ve built. This operator has capabilities I don’t have. That athlete can do things physically that I’ll never be able to do.

You can play that game all day long if you want to.

And what a waste of the room.

Comparison turns your attention inward at exactly the moment when you should be paying attention to what’s around you. Instead of listening, you’re evaluating yourself. Instead of learning, you’re wondering how you’re being evaluated. You finally got access to the room and then spend the whole time thinking about yourself.

Somewhere along the way, I learned to approach those situations differently. I became much more interested in learning and listening. I wanted to understand what these people knew that I didn’t know yet, and then use what I learned to level up my own ability to serve people at the highest possible level.

I don’t need to have what the billionaire has. I want to know what he knows.

How does he think about money? What does he see in an opportunity that I might miss? What did he do when the deal collapsed? What did he learn when he lost? What does he know today that he wishes he had known thirty years ago?

The same thing is true with an elite operator. I may want to understand how he prepares, how he manages fear or how his team functions under enormous pressure. With an athlete, I might want to understand discipline, repetition and performance. With a spiritual leader, I may want to know what he learned through decades of faithfulness, failure and getting back up again.

Different rooms contain different kinds of wealth.

And that’s important because money is not the only currency in life.

Wisdom is a currency. Health is a currency. Relationships are a currency. Trust is a currency. Competence is a currency. Reputation is a currency. Faith is a currency. And one I’ve been thinking and teaching about a lot lately is access.

But I also think we make a mistake when we become so philosophical about wealth that we pretend money doesn’t matter.

It does.

Money creates choices. It can give you control over your time. What you say yes and no to.  It can give you access to people, experiences and opportunities. It allows you to solve certain problems faster. And in the hands of a good man or woman, money can dramatically increase their ability to do good.

So yes, I want to learn from billionaires.

I’m interested in all the currencies.

What I Learned in the Anthony Robbins Rooms

Some of the best examples of this came during my years working in and around Anthony Robbins companies and events. I spent a lot of time in those rooms, including with Platinum-level clients. There were people from all over the world who had built extraordinary businesses, created tremendous wealth and experienced things most people never will.

I learned an enormous amount from Tony. I learned about state, human needs, the meaning people attach to events and how quickly a person’s life can begin to change when you help them interrupt an old pattern and create a better one. Many of those lessons became part of my own work.

But I also learned something else that has probably been just as valuable.

Sometimes the person sitting beside you is as important to your education as the person standing on the stage.

So I talked to people. I asked questions. I listened. I became genuinely curious about who they were, what they had built, what they had learned and what had cost them the most to learn it. Relationships developed. And sometimes I eventually found myself coaching the very people I had originally been interested in learning from.

That taught me something about success that I think is incredibly important.

The billionaire may understand things about creating wealth that I desperately want to learn, but that doesn’t mean he understands everything I understand. The CEO who can brilliantly run a company may be completely stuck somewhere else in his life. The professional athlete may possess physical abilities I’ll never have and still need help with something I’ve spent thirty years studying.

Everybody has something to learn.

And everybody has something to give.

That realization changed the way I entered these rooms. I didn’t have to pretend to be something I wasn’t. I could respect another person’s success without diminishing my own value. I could be a student without becoming inferior.

And I could be a giver without needing to be the most important person in the room.

The Dancing Cowboy and the Cure for Imposter Syndrome

Keith Ferrazzi wrote something in Never Eat Alone that captures this beautifully:

“The currency of real networking is not greed but generosity.”

That principle has been huge for me. I’ve never liked walking into a room and immediately calculating who can do something for me. I want to know people. I want to hear their stories and understand what matters to them. And if I can bring something of value to their life or to the experience, I want to do that too.

Sometimes that might be an idea. Sometimes my training or experience allows me to help someone see something differently. Sometimes I can make an introduction. Sometimes the relationship eventually turns into coaching, business or a friendship.

And sometimes what I can bring to the room is simply some damn fun.

During my years around the Anthony Robbins world, I somehow became known in certain circles as something of a dancing cowboy. I wore my old Stetson Cowbay hat… aptly named “Stella”… I rarely went to an event without it. After Tony’s events, there was always a VIP get together… many times a live band with food and dancing. I love to dance, and when the music started I wasn’t going to stand against the wall trying to look important. I was going to have fun. Pretty soon some of the most beautiful women in those rooms would come dance with me. I was always pleasantly surprised about how these ladies looked for me… and even cam and got me to dance. I would be surrounded… in the middle of about 10 or 20 gorgeous women… all dancing and having a ball with Cowboy Keith. Their boyfriends didn’t always appreciate it, and I definitely got a few looks. LOL. But it didn’t stop us.

I think the women understood something that really mattered: I wasn’t trying to get anything from them. I wasn’t trying to pick them up or prove something about myself. I was there to dance, have fun and hopefully make their experience more fun too. We were ridiculous and just had a blast.

I’ve realized since then that there is something much bigger in that story.

I knew who I was, and I was there to give before I was there to take.

That is one of the core principles that has allowed me to go into almost any room.

Think about what that does to what we now call Imposter Syndrome. If I walk into a room with billionaires wondering whether I’m successful enough to belong there, I’m going to become self-conscious almost immediately. If I’m wondering whether they think I’m important, whether my résumé measures up or whether I’m saying the right things, I’ve made the entire experience about me.

This is where most people fail!  They focus too much on themselves and not enough on learning and serving. And very rarely do they allow learning and service to form an Identity of Self.

I became “Servant Leader”… a man who was not there to take… but to give. Not to compete but to serve. I was there to learn and celebrate the potential of who they could be. Yep… I still do this in every room I’m in.

So, what happens if I walk into that same room asking two completely different questions?

What can I learn here, and what can I give here?

Now I don’t have to audition for the room.

That’s a big deal.

I don’t need the billionaire to validate me. I don’t need the general to think I’m tough. I don’t need the celebrity to know my résumé. I don’t have to become somebody else just because I’m sitting with somebody extraordinary.

I can appreciate what another person has accomplished without using his accomplishment as evidence of my inadequacy.

And I can remember something else: I brought something to the table too.

Maybe that’s one of the best cures for Imposter Syndrome I know.

Here’s the formula:

Know who you are. Stop auditioning. Get curious. Then find something to contribute.

Go Sit in the Hotel

Which brings me back to the original quote.

I think you should actually try it.

Go to one of the finest hotels in your city. Put on some decent clothes, order the coffee and sit there for a while. Don’t bury yourself in your phone. Look around. Listen. Pay attention to the environment, but also pay attention to what starts happening inside you.

Do you feel like you belong there? Do you start comparing yourself? Does somebody walk past who appears enormously successful and suddenly you feel a little smaller?

Good. Now you have something useful to work with.

Instead of asking yourself, Do I belong here?, ask, What can this room teach me?

Look at what appears normal in that environment. What do people talk about? How do they carry themselves? What kinds of decisions are being made? What assumptions do they seem to have about money, opportunity, time or possibility that may be different from yours?

Then ask yourself a question I think matters even more:

What would have to change in me for the next level of my life to become possible?

The purpose isn’t to pretend you’re wealthy. It certainly isn’t to spend money you don’t have trying to appear successful. You’re changing your reference points.

Environment affects state. State affects what we notice. What we notice influences the story we tell ourselves about what is possible, and that story eventually affects what we do.

Sometimes you need to physically move yourself out of the environment where you’ve been thinking about the problem.

Go somewhere else. See something else. Listen to different conversations.

Then think again.

Find Better Rooms

There’s another question I’ve learned to ask over the years that connects directly to this. Dan Sullivan and Benjamin Hardy talk about it in Who Not How.

Most of us encounter a problem and immediately ask, How am I going to do this?

A better question is often:

Who already knows?

I’ve struggled with things that somebody else could help me understand in twenty minutes because they had already spent twenty years learning the lesson.

That doesn’t mean I blindly copy them. It means I respect the value of their experience.

That’s why books like Keith Ferrazzi’s Never Eat Alone, Dale Carnegie’s How to Win Friends and Influence People, Adam Grant’s Give and Take, Dan Sullivan and Benjamin Hardy’s Who Not How, and Alex Banayan’s The Third Door are worth reading. They approach relationships, generosity, access and learning from different angles.

But don’t just read about getting into better rooms.

Go find some.

Attend the conference you’ve been thinking about. Accept the invitation that makes you slightly uncomfortable. Call the person who knows something you don’t. Sit at the table where you’re not the expert.

And when you finally get there, don’t waste the opportunity trying to prove you deserve the chair.

Listen.

Ask a good question. One of my favorites is, “What do you know now that you wish you’d known twenty years ago?”

Then actually listen to the answer.

Look for the lesson instead of the comparison. Look for what you can learn, but also look for what you can give. Maybe you know something that can help. Maybe you can make an introduction. Maybe you can encourage somebody. Maybe you can solve a problem.

Maybe you can just be the dancing cowboy and make the damn room more fun.

Then take what you learned home and use it.

Because proximity isn’t achievement. I’ve seen people become fascinated with being around successful people because they want the photograph or want everyone else to know who they know. I don’t care how many billionaires you’ve met. What did you learn, and what did you do differently because you learned it?

Standing next to greatness doesn’t make you great. Getting a photograph with the operator doesn’t make you an operator.

You still have to go home and work.

Proximity gives you access. Execution turns access into growth.

After all these years of coaching people, building businesses and working with some extraordinary people, I still intentionally look for rooms where somebody knows something I don’t know.

I hope that never changes.

I want to keep learning. I want to keep listening. I want to keep becoming more capable so I can serve people at the highest possible level.

And I’ve learned I can sit comfortably in those rooms because I don’t need to walk into them trying to take something.

I can walk in looking for an opportunity to give something too.

So go to the expensive hotel. Order the coffee. Find the better room. Sit with people who have currencies you haven’t developed yet. Learn what they know.

But don’t shrink when you get there.

You don’t have to be the richest person at the table. You don’t have to be the smartest, strongest or most accomplished.

Know who you are. Be genuinely curious. Bring what you have to give.

And then take what you learn and use it to become more valuable to the people you’ve been called to serve.

Because after spending years in these kinds of rooms, coaching some of the people in them and sometimes eventually partnering with them, I’ve learned something:

The goal isn’t to become the most important person in the room. The goal is to become better because you were in it.