The Psychology of the Executive Money Mindset

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As I experience new and memorable life moments — such as watching Noah discover the world, traveling with my family for public speaking and client visits, or simply taking a fresh breath of the ocean breeze in Hanalei — I have started to see the world through a new lens. 

Notably, my mindset regarding money and success has matured. 

Last week, my business partner Meagan DeMenna and I hosted our first bougie executive dinner at the Global Ambassador in Phoenix.  

Nothing compares to sharing a hug with clients who’ve turned into friends whom you’ve shared dozens of hours with. 

We all yearn for a real connection, especially when you’re isolated and, too often, ostracized executive leaders. In-person engagement is the way to be, and I’ll continue to be bullish on face-to-face interaction.

While in Phoenix, we laid the foundation for the latest ThinkWarwick brand — with valuable video content and photography with Brian Bossert.

I’ll be honest: I felt massive anxiety about how much it cost (and will continue to cost) to realize our vision.

I’m uncomfortable (and it shows).

I’ve wrestled with a frugal vs. extravagant mental state throughout my life. I’ve leaned into winning results as the scrappy and resourceful persona, primarily out of necessity and not by choice. 

However, the mindset that has gotten us to where we are today no longer serves our future. 

Again, I’m uncomfortable exploring this new territory.

As part of our ThinkWarwick resurgence, our consultant, Camille Moore, pushed me to get on Instagram (and YouTube to follow). 

For those of you who know me well, you’ll notice that I’m a walking contradiction—a Tommy Bahama-wearing silent generation ancient trapped in a bitchy Millennial dad bod. 

I’ll take Sinatra and Werther’s Original over TikTok and Fortnite any day. Again, I’m uncomfortable exploring the social media play—especially while trying to avoid the perception of being a cheese ball influencer. 

Anyway – as I’m stalking the ‘gram’ of friend and mentor Kayden Kelly — I noticed he used the hashtag #SmilesPerHour. It got me thinking. 

Maybe I’m having an epiphany—or maybe I need to justify the “easy come, easy go” label attached to investing in yourself and your business.

Should I be frugal or extravagant—or maybe both? Am I thinking about ROI all wrong? Should I be measuring smiles per hour instead?

I’m comfortable with frugality but uncomfortable when placing big bets. Even when those bets are on me and my team, and the gamble is scrutinized and obtainable. 

I suspect that you can relate. It’s easier to spend someone else’s money.

I’ve always respected my clients — but often, it’s been difficult for me to relate to their lifestyle of increasingly higher standards and extravagant spendy habits.  

This likely comes from growing up with an eccentric distrust of wealth and a propensity to scrimp and obsess over every flipped light switch racking up the PG&E bill. Which I still do, for some reason. 

Furthermore, I’ve learned that my mentality about money is toxic. 

I’ve hated it, feared spending it, felt anxiety asking for it, and stressed about how to keep it—and villainized those who have more than me. Why? 

I’ve recently learned a new perspective.

If you hold contempt for money — you won’t respect yourself enough to negotiate for it — whether you deserve it or not.  

It’s been a trap for me and hundreds of clients, especially those who are told, “You already have enough. So much more than others. Just be happy with what you’ve got. Why do you need more?”

The problem? 

It’s not really about happiness or having enough or even being greedy. If we can do and achieve more, then why not? 

Should Brady, Jordan, or Schumacher have stopped winning championships at 1 or 2 to give everyone else a fair shake? My 49er friends may wish Mahomes retired.

Socrates said, “The secret of happiness, you see, is not found in seeking more, but in developing the capacity to enjoy less.” 

And Plato added, “The greatest wealth is to live content with little.”

I don’t disagree. But it’s also quite boring, for me anyway.

Look, I’m okay with nothing, and I oddly found peace during a period of homelessness in my twenties. That experience is why I don’t think anything in corporate America is genuinely risky—it’s simply not life-or-death. 

Can we enjoy less, be content with little, and still go after more? Or is that a philosophical oxymoron?

I don’t suggest that you will find unspoken peace and happiness gated behind shallow bullshit in the material world — I’m suggesting that you can want nothing and be freed to achieve the “impossible” as a result of your unshackling. 

Wanting nothing but striving for an audaciously ambitious vision is a damn strong position of negotiation leverage to have.  

And as those blessed to live with more wealth, we can become less frugal and more generous to others. 

Your cup must runneth over to provide more for your community. 

Growing from boy to man, man to husband, and husband to father has given me a more sophisticated respect for wealth—and a greater desire to be more generous in giving to those who WOW me, no matter their discipline.

But I’m still uncomfortable and torn. 

I don’t want to spoil my kids or give them the wrong idea about what most of society experiences.

I want my family to recognize our blessings and privileges and be satisfied with life — but I also want more for them and those we can impact. Is that line of thinking negotiating against one’s self? 

Can we be satisfied with nothing, grateful for everything, and still negotiate for more?

As I continue to challenge why it’s imperative to negotiate a more prosperous life, I’ve found opposing and often hypocritical forces at play in my mind. 

For example, is driving for more greedy? If so, at what point does it become greedy? And as one of the seven deadly sins—is money also the root of all evil? 

Depending on who you ask, you’ll get different answers.

I used to scoff while walking past first-class fliers and valet users as wasteful and frivolous — but now I recognize the time savings and experiences are well worth it for those fortunate enough to have the luxury. 

I’ve made my decision. 

Driving for more isn’t greedy. 

Greed comes more from what you do (or don’t do) with your “more.” 

If you think money is evil or greedy, you negotiate against yourself and will never have the opportunity to see the other perspective.

Yes, giving more wealth to ungenerous people can increase their propensity for greed. 

However, providing more wealth to generous people can increase their capacity to be charitable to those who need it most.

Money can be an accelerant of the good intentions you have in motion. 

But without it, you lack the power to drive the change you want to see in the world. You are limited in what you can accomplish.

With it — you can use your wealth for good or bad—or a combination of both if you’re anything like me and most folks. Who am I to judge? 

What’s best may be to prioritize and allocate your resources consciously so that you are frugal in many areas of your life and overspend on the things that matter most to you. 

For me, that means spending extravagantly on my family and my business—with the intention of maximizing our impact to generate wealth for others. If we’re responsible, we can successfully build a massive forum as leaders of leaders. 

In that case, we can impact millions with practical ways to negotiate better lives for their families and communities. 

But to accomplish this—it means I must stop negotiating against myself and having a toxic relationship with money because a lot of it will need to pass through the right hands to achieve the vision. 

More often, negotiating for more is about the quality of your experiences, freedom, and security—and about being respected for your contributions during our fleeting human existence. Or, let’s not be overly naive, it’s for sport because other elements of life get boring.

Perhaps your next negotiation may be your personal battle to earn the luxury of paying for smiles per hour — as it were. 

Now I’m feeling poetic, and my language below will be “flowery,” as my editor, Mark Earnest, puts it. 

Noodle on the following perspective I’m written for myself:

I’ve found passion in driving a lifestyle that embodies excellence and inspires others to reach greater heights—demonstrating the pinnacle of achievement during our human experience.

As you continue to grow your wealth and negotiate for more, I ask you to sharpen your focus on what truly matters. 

In the wrinkles of time, we must discern the difference between superficiality and substance, between fleeting trends and enduring excellence. 

Quality, mastery, and genuine passion stand out like beacons, illuminating your journey with depth and meaning. 

And these cream-of-the-crop moments often demand serious financial investment.

So next time you debate whether you’re “worth it”  and negotiating against yourself—instead:

Negotiate for a life where you can afford to recognize the beauty of craftsmanship, the allure of expertise, and the fire of authentic devotion. And get more than enough to pay generously for those who inspire your spark, regardless of their passion and areas of mastery. 

And the sacrifice and dedication you’ve made to your career mastery should be rewarded. Who has the right to limit or cap your potential? Limiting your growth better not be coming from you.   

I recognize that few people think this way — but the ones that do have unlocked a new level of distinction in their lives, and I’ve been honored to work with a small handful throughout my career. 

My final considerations for today’s exploration of money mindset involve how to ask for money. Especially increasingly big-time numbers.  

Now we’re all uncomfortable.

Since adopting a value-based pricing model for my services, I’ve won deals of $5,000, $10,000, and even $20,000 an hour for the most significant client outcomes. 

Even I’m in awe of this and pinch myself to wake up.

I’m also asked several times weekly about my hourly rate. 

I should be proud—but I’m uncomfortable and almost embarrassed by how big the numbers have been. WHY?! The outcomes have been there. 

As I negotiate against myself, I’ll say, “People will think that’s a ridiculous price to pay,” which is a valid emotional reaction, but how you feel about the matter doesn’t make the facts any less factual. 

Others will recognize that the impact must have been transformational to demand that rate. 

After all, I only get paid well with outcome-based pricing if you do. And it’s a bet I’ll take repeatedly on the right people.

My clients demand the best in preparation for the right moment and are not afraid to bet on their best shot at winning big. 

I’ve also learned that the moment to pounce is highly nuanced and quickly fleeting. 

Deep knowledge and perfect timing must align to maximize the most impactful outcomes.

It’s challenging to strike the right moment to maximize that value — because it takes 15+ years of hyper-specific experience, 10,000+ hours in the trenches, and thousands of conversations to identify the trigger moment and understand precisely what to advise the client to do to win. 

Your career and experiences are similar. 

Your employer needs your very specialized experience at the perfect moment to achieve their ambitions—your decades of experience all magnify on this one performance. And there’s a lot on the line—or your ass is on the line. 

Think of your career this way: 

Imagine a symphony conductor who spent years studying music theory, practicing tirelessly, and learning from the maestros. 

Each rehearsal, note, and lesson leads to one performance. As the baton rises, every ounce of preparation converges into that moment. The audience holds its breath. 

In that fleeting instant, the conductor orchestrates a masterpiece, drawing from the depths of their experience, knowledge, and passion. 

The culmination of thousands of experiences, dozens of books, and countless hours manifests in the harmony of a single crescendo, proving that meticulous preparation meets opportunity at the perfect moment.

When the above is your reality, and your mindset about money is healthy, that’s when you can negotiate for the type of compensation that others cannot. 

Go out and break away from the false authority the world has propped up to keep you down—then look in the mirror and make sure the one staring back at you isn’t stifling your dreams. 

Stay fearless, friends. 

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