I started in financial services at the age of 19. Ambitious and curious, I set out to figure out more about money and investing.

At first, I thought it was about how hard one could work and how much money they could save.

Work hard, cut expenses. That was my mantra.

It’s definitely possible to become a multi-millionaire doing it this way, but at the expense of enjoying life along the way. And you’ll end up with less than if you were to have a different mindset and philosophy anyway.

I leveraged my young age to meet with wealthy people and advisors. People often want to pay it forward and love seeing a young person who is willing to learn and listen.

What I learned from the wealthiest people I interviewed is that hustle and frugality were not how they operated.

As shocking as it was for me to discover that it wasn’t about being frugal, it was even more surprising to find out that it wasn’t about Wall Street or net worth either.

The more people I interviewed, the more they talked about investing in business, intellectual property, and real estate.

And yet, the older, more established the person, the more likely they saw wealth from a completely different perspective. It was more about quality of life.

My earliest mentors, Dan Sullivan, Babs Smith, and Kim Butler, encouraged me to take time off. Find my Unique Ability. Do more of the things I love and delegate everything else.

More time off. That was the strangest piece to my young hustling mind. Free days. Days off. Trips and enjoyment.

Babs said this would lead to more production, and she was right.

So what is wealth to you? How do you know if you are wealthy or not? How do you measure? Is wealth simply about having more than others you know?

What happens when more no longer creates happiness? Or when it actually creates more stress and even starts to destroy your life. Your marriage. Your health. Your quality of life.

It is time for new questions. Questions like:

What makes you happy?
What do you really want?
Is the pursuit of wealth taking away from your best life?

Are you looking to grow and would you like to have more, but managing what you already have makes it impossible to be present? Does your mind wander as you think of everything that needs to be done?

We may have misidentified what wealth actually is.

When it is about net worth, likes, views, social media clout, cars, and houses, these all require energy and stewardship.

But how nice does our home have to be for us to be happy? What kind of car do we need to drive and why? How many followers, subscribers, and comments are enough?

The things that are the most fulfilling personally, don’t always translate professionally. A moment with my wife, a laugh with my sons, a dinner with the family.

We think of how hard it is to build wealth, but in today’s world, it may be even harder to be present. Or harder to know what really makes us most happy. Or be able to say no to something that seems like an opportunity.

One of the hardest, yet most rewarding things is to determine and know our win. To design a game worth playing. To establish our rules to live by. To design our day and carve out time for life.

Could there be things that add to your bottom line, but take too much energy or time from your life? Have you ever started a project that robbed your health or time with your family? Did you learn your lesson?

The more I take on, the less happy I become. The more I have to manage the more it takes away from my winning game and enjoying today.

I want to write, create content, perform, do immersions, and connect one-on-one with amazing people. When I say yes too often, it can come at a steep cost.

In my twenties, I didn’t consider the impact stress could have on my health. I didn’t consider the energy that any project required, and how much I’d have left when I got home after work to my two kids who were so elated to see me. They’d be dressed up in some ninja or superhero custom jumping up and down, and I had nothing to give them.

I miss those days. I missed too many of those days. So I created a new game.

A game where my oldest son traveled with me for my book tour. We shared a room. He learned from the other speakers and attendees. He filmed testimonials. He took notes for himself. We connected. We bonded.

A game where my youngest helped me memorize my lines for my theatrical keynote and opened for me when I filmed my comedy special.

What’s your win? What’s your game?

I used to think real estate was the only path to wealth. But if I were to invest in real estate like I used to, there would be less time to write. It would take time away from rehearsing my theatrical keynote or adding a musical score.

When I start thinking of buying more real estate or starting a new business or wanting to do more social media, it takes me away from enjoying the moment.

Is it worth it?
Is this what I really want?
Is it congruent with who I really am and the energy I am willing to dedicate?

To create a winning game, consider what you could dedicate decades of your life to. What would you be willing to work on regularly. Where can you find joy in the process and find the win in the work.

What is wealth to you? At what point or amount is someone considered wealthy, and who makes the determination?

When it is unclear, when the target moves, we go for more. More time. More hustle. More opportunity. More energy. More of anything.

What if more is an enemy of joy and excellence?

What if more was redefined? More depth. More shared moments. More presence.

What jealousy, comparisons, and desires move you away from things that matter to you? What happens inside you when you aim for the wrong, insatiable more?

When I started buying real estate, I didn’t have a goal other than to get as much as possible. And then my life started to suffer. Vacations were always filled with obligations with contracts, property managers, bankers, and everything to get more real estate.

It is painful and even embarrassing to think of a trip with my wife to a beautiful resort where I was on the phone constantly. And that wasn’t the only time. I was taking calls rather than being with my family ruining a Halloween. It was a constant disruption.

How did I get there? Saying yes.

Why did I say yes? Wanting more. An underdeveloped philosophy. Unclear of what a win was or the life that I wanted.

Shit, even greed. I wanted people to think I was cool, successful, and that I was wealthy.

My pursuit of respect and love came from not fully accepting and loving myself. Trying to prove my value externally to validate my insecurity inside.

For the longest time, I thought wealth was how much I had and how much I displayed. I should have listened to those early interviews with the happiest wealthy people.

There is a point where more starts to limit enjoyment today. What are you wanting and willing to be a steward over? Is it worth your time and energy? What is the cost for the payoff?

The next piece of real estate, the next business, the next project, these all add up and can occupy our mind and disrupt our lives. Much of how we are trained is in the process of more. Books. Podcasts. Social media. Awards and accolades. More growth. More stuff.

But what about more energy? More fulfillment? More presence?

Do you consider the energy required before making the next investment, or starting the next project? Even if something is an amazing opportunity, do you consider how it impacts your life? Do you consider your winning game?

Or are you stuck in sacrifice? “If-then” is not a winning game. “If” I get this, “then” I’ll be happy…we become our sacrifice.

Sacrifice forms habits that are always about the future instead of today. Bad habits that drown out today. Habits that society will reward and respect though. Habits that will leave you with money, but leave you a shell of yourself.

What is monitored and measured can be improved. But what about things that can’t be measured? Love. Happiness. Special, magical moments. Being present. What happens when we measure so much that we forget what really matters and what we really want?

When does more stuff increase net worth, but decrease happiness? When do you have so many people to manage that everything feels overwhelming and stressful.

Know who you are and know what you want. You can have wealth and riches with a life you love. But what is wealth to you? What is your richest life?

What are the best days of your life? What are the best moments of your life? Coco Chanel famously said,

“The best things in life are free. The second-best things are very, very expensive.”

So what can you monitor and manage without losing the very best things? And what are the very best things for you?

For me? The day I got married. The birth of my sons. Dates with my wife. Family traditions. Roasting a friend. My morning writing time. Time at my cabin. One-on-one immersion with a client.

It wasn’t selling my business. Or the few videos that had more than a million views. It wasn’t being recognized by a stranger who had seen me online. It wasn’t buying a property just to make a profit.

None of these things are bad, or wrong. They are just less fulfilling for me, yet what society values more than family.

The best things don’t show up on a bio or get you a public award. Like when my kids made me something at school, call me “dad,” or cuddled up, or said I was worth more than gold, or their hero, that is more than a fleeting feeling, it is magic.

Magical moments.

In a world tempting us with quantity, what really matters is the quality of our life. The presence of our mind.

For me, it is about intimacy. Sharing a unique moment. Having a deep conversation. Being trusted and trustworthy. Seeing people and being seen.

Not being seen as a bio.

Those fleeting moments of acknowledgement that have little to do with my daily life. But the lasting moments of love, of gratitude, and of creating space for someone to feel free to be themselves.

A winning game is about creating an exciting and compelling future without sacrificing today. It is about having time to yourself and listening to your inner-knowing.

It is about living with intention and honoring your value and life. It is about having rules and standards and a vision that is so compelling that you have a life you wouldn’t want to retire from.

Sometimes we learn what is not our winning game. I’ve confused being known with being valuable. I’ve invested a lot of time to be cool to strangers. In the past, I’d speak at almost any event, even if it meant feeling overcommitted and exhausted. Even if my wife was feeling lonely.

And I am going to come clean, sometimes I say yes because I like the feeling of “fame.” Now, I’m not really famous, but with my old company and all our ads we ran, I was getting recognized one, two, or sometimes three times per trip at the airport.

It felt good.

Some interactions were really good like saying Killing Sacred Cows changed their life. My wife would roll her eyes or keep walking. These short conversations felt good, but I never got to know the person on a deep level. It simply fed my ego. I’m not saying it was bad, or wrong, just limited. Not aligned with my values of intimacy, vulnerability, and connection.

I love meeting the people behind the likes, comments or views. That is really fulfilling, if I take the time with them.

Before speaking at SAAS Academy (doing my theatrical keynote), I was able to meet two brothers that had read my books and watched my videos. And we talked for over an hour. This is the winning game for me. We spoke multiple times at the event. There was a connection. Not a fleeting “like” or “view,” but a genuine connection.

That is my winning game with my YouTube channel or IG. To lead to these conversations where we can go deep quick. Where we find common ground and shave off time to get to what matters.
I’d rather people know me well, than being well known without depth.

Know your winning game with social media or someone will convince you to hire them and do what they want (which is not likely to be what you want). This is a steep cost. It is steep if it isn’t in alignment with what you really want to do each day. If it comes at the expense of sleep, enjoying your life, and being present.

My most read book, What Would the Rockefellers Do?, didn’t require social media posts, speaking tours, or book launches. Financial planners and insurance agents love it and use it regularly—often buying it in bulk to give away to clients.

What happens when you dedicate yourself to your work and craft? What if you do what you really love and do it at the highest level?

Some people want to get the fame without doing the work. If you love the work and the fame comes along, great. If you delegate so much of the work you aren’t related to the vision, you miss out on enjoying the process.

So get clear about what you want and what you don’t want.

What do you want to do and where you could collaborate so you can focus on what you love and do best?
What is your vision? What matters most to you?
What makes life great and a day you look forward to?
What is magical to you?

Creating my theatrical keynote/one man show has been a gift. The preparation, the process of creating it, and the words I speak are like an instruction manual for my own life. The way to be present. To be connected. To create shared and magical moments.

Rather than do something scalable, I’m choosing to do something special. Something that connects me to who happens to see it. This has been my gift in how to be present.

I’ve struggled for years at being present. My mind wanders. It stays busy. What needs to be done next, what else can I conquer or achieve? I wanted more projects, businesses, real estate, net worth, but hadn’t defined more happiness, joy, presence, depth, and excellence. Without knowing my winning game I said yes too often.

To be world class at something requires time and presence. It requires vision and commitment. It requires collaboration and coaching.

It is time to assess your calendar and life. I’ve learned to say “not now” if it isn’t a “hell yes.”

You decide your game and what matters. What allows you to be present? What would you dedicate your life to? What makes you feel alive and joyful?

What is your win?