When Success Becomes a Cage: Why Leaders Need a Bigger Definition of Wealth

The most dangerous thing about success is how easily it can become a cage.

From the outside, a leader’s life can look enviable: the title, the compensation, the recognition, the visible markers that say, you made it. But internally, many high achievers carry a very different reality.

They are exhausted. Disconnected. Still chasing. Still restless. Still quietly hoping that the next milestone will finally create the feeling they thought success would bring.

That tension sat at the heart of my conversation with investor and entrepreneur JP Newman. His story is one so many leaders will recognize. He spent years pursuing a vision of success, assuming that if he achieved enough financially, fulfillment would naturally follow. But what he discovered is something I have seen again and again with senior executives: money can amplify your life, but it cannot define it for you.

Why achievement often fails to create fulfillment

Many leaders are operating from an unspoken formula:

Work hard. Achieve more. Hit the number. Then feel better.

It sounds rational. It is also incomplete.

JP described setting a goal in his twenties to have a million dollars in the bank by age 30, along with all the outward symbols of a successful life. Instead, when he turned 30, he was broke, single, and humbled. Later, when he did begin achieving the material goals he had once visualized, he was surprised by his own reaction. Rather than pure satisfaction, he felt panic and anxiety. Why? Because he had spent years chasing outcomes without getting underneath what those outcomes were supposed to mean.

This is where so many leaders get stuck.

They are disciplined enough to build the strategy. Smart enough to execute. Ambitious enough to keep moving. But they have not paused to ask a more important question:

What am I really hoping this success will give me?

Very often, the answer is not actually money. It is safety. Freedom. Belonging. Peace. Significance. Love. Space to breathe.

And when those emotional drivers remain unconscious, leaders can spend years pursuing goals that never truly satisfy.

The real issue is not money. It is meaning.

One of the most striking ideas from the conversation was JP’s phrase, “the why that makes you cry.”

That phrase gets to the heart of leadership maturity.

High-performing people are often excellent at naming their targets. They are less practiced at naming the deeper emotional truth beneath those targets. They can tell you the revenue goal, the promotion they want, the lifestyle they are building toward. But ask why that matters, and many discover that their answer is thinner than they expected.

That is not a failure. It is an invitation.

Because transformational leadership starts with self-awareness. And one of the most strategic things you can become aware of is whether your ambition is actually aligned with what matters most to you now.

A bigger definition of wealth

JP’s framework for this is what he calls the five dimensions of wealth: prosperity, purpose, people, presence, and play. While the language is his, the leadership lesson is universal. If your definition of wealth only includes money, you may build a successful life that still feels deeply uninhabitable.

Here is why each dimension matters for leaders:

1. Prosperity: health and wealth must work together

Many executives know how to drive results while running on empty. They normalize overextension because it is rewarded. But prosperity without health is fragile. If your body is paying the price for your ambition, the model is not sustainable.

Leadership is not just about producing outcomes. It is about building the internal capacity to sustain those outcomes over time.

2. Purpose: your work needs a deeper anchor

Purpose is your connection to meaning, contribution, and legacy. It is what keeps success from becoming hollow. Without purpose, achievement turns into an endless scoreboard. With purpose, achievement becomes an expression of what matters most.

This is why some leaders hit every external benchmark and still feel strangely flat. They have built a high-performing life, but not necessarily an aligned one.

3. People: success without connection is a lonely win

JP made a powerful point that people wealth begins with your relationship to yourself, then extends outward to the people who matter most. For leaders, this is essential. You cannot build trust, lead teams, or create strong culture if your success consistently comes at the expense of your closest relationships.

The question is not just, How well am I performing?
It is also, Who am I becoming in the process?

4. Presence: time is not the issue—attention is

I especially appreciated his distinction between time wealth and presence wealth. We all have the same hours in a day. What differs is our relationship to those hours.

Presence is the ability to be where you are while you are there.

For leaders, this matters more than ever. If your mind is always in the next meeting, the next fire drill, the next target, you may be physically present but relationally absent. Presence is what allows you to listen deeply, make cleaner decisions, and respond rather than react.

5. Play: joy is not a distraction from leadership

Too many leaders treat joy as a luxury they will return to later. Later, when the company is stable. Later, when the deal closes. Later, when the pressure lifts.

But play is not frivolous. It is a source of energy, intuition, and creativity. When leaders lose access to joy, they often lose access to possibility as well. They become efficient, but not expansive. Productive, but not fully alive.

And that always shows up in how they lead.

What this means for leaders

The deeper lesson here is not that ambition is bad. It is that ambition without self-awareness can quietly imprison you.

Your greatest strength can also be your biggest blind spot.

The same drive that helped you build credibility may now be keeping you overcommitted. The same hunger that fueled your rise may now be making it difficult to feel satisfied. The same discipline that earned trust may now be crowding out presence, connection, and joy.

This is why personal evolution and leadership evolution are inseparable.

When leaders redefine wealth more broadly, they lead differently. They stop using achievement as proof of worth. They make decisions from alignment rather than fear. They become more grounded, more human, and often more effective.

Because the goal is not simply to make more.
The goal is to lead and live in a way that feels true.

Action steps you can take this week

Start with these questions:

1. Define what success is supposed to give you.
Pick one goal you are chasing right now. Ask yourself: What emotional experience do I believe this will create for me? Safety? Freedom? Belonging? Peace? Name it clearly.

2. Audit your current definition of wealth.
Are you measuring your life only by financial or professional metrics? Or are you also tracking purpose, relationships, presence, health, and joy?

3. Identify one neglected dimension.
Which area has been underfed lately: prosperity, purpose, people, presence, or play? Choose one and make a concrete commitment this week.

4. Stop moving the goalpost.
Many leaders live with a constantly shifting definition of “enough.” Instead, ask: What would enough look like for this season of my life?

5. Reconnect success to service.
JP spoke powerfully about wealth becoming more meaningful when it flows outward in service and contribution. Consider where your work, resources, or leadership can create real value for others.

Final thought

If success feels heavier than it should, that does not mean you are doing it wrong. It may mean you are being called into a bigger conversation about what wealth really means.

Not just net worth.
Not just status.
Not just what looks impressive from the outside.

But the kind of wealth that allows you to feel grounded in yourself, connected to others, clear about your purpose, present in your life, and energized by the way you lead.

That is a much more powerful definition of success.

And ultimately, it is the one that sets you free.

Episode Transcript

Susan Drumm: The most dangerous thing about success is how easily it can become a cage. Does it ever feel that way to you? I’m Susan Drumm, and this is The Enlightened Executive, where your personal evolution sparks your leadership evolution.

Each week, we spotlight cutting-edge strategies to help executives and entrepreneurs grow in leadership and in life. My guest today is JP Newman, who helps high achievers stop building prisons out of their success and start designing lives where money fuels their freedom, not their fear.

JP is an investor, an entrepreneur, and founder of Thrive FP, a real estate investment firm focused on multifamily housing. He’s also the creator of Fulfillionaire, a professional coaching service that helps high-net-worth individuals redefine wealth beyond their net worth by achieving clarity and alignment across four dimensions: purpose, people, presence, and play.

Through his writing and speaking, JP blends practical financial strategies with personalized inner work. Okay, JP, welcome to the show. I’m so excited to have you here.

JP Newman: Thank you. It’s very exciting to be here. I already know this is going to be a great show from the first fifteen minutes we started brainstorming together.

Susan Drumm: Yes, and in that brainstorming session, some of the things we were talking about is this concept of — well, we talk about it for this podcast — your personal evolution sparks your leadership evolution. So we look at this contrast between what’s going on internally for us and what’s going on externally for us. I’d love to hear a little bit how you would comment on that.

JP Newman: Sure. Well, I’ll tell you one thing which is kind of fun. I just became an empty nester — I call it “open nesting” — six months ago. I got both kids off to college, and after I dropped my son off at the University of Miami, the day after, I went to Burning Man. It was the first time I’d been to Burning Man.

Susan Drumm: It’s what any responsible father would do. You’d go to Burning Man, right?

JP Newman: Right. And the last time I’d been to Burning Man was twenty-three years ago. I went with my wife, who was my girlfriend at the time.

When I got there, I wasn’t really expecting much, but as I was watching the sunrise, I realized that the dream that kid had at thirty-one years old — when I went to Burning Man with my girlfriend who became my wife — I was actually able to far exceed. And it wasn’t just exceeding the dream financially, which financially things had worked out great. But I never could have imagined that I could have actually found so much fulfillment and joy.

And I cried. I just cried as the sun rose, and it was a cry of gratitude — that the dream that kid had actually turned out better than he could have ever dreamed of. My movement, Fulfillionaire, is a lot about that.

When you cut down to it, I see so many people — and maybe because I’m a bit older now, I’ve had my company for twenty years, I’ve done a lot of life — but what I’ve seen is there are so many people, as someone who works with a lot of wealthy, high-net-worth and accredited people, who haven’t quite found that fulfillment yet. So Burning Man, for me, in that moment of being an empty nester, has really been a moment of just wanting to spread Fulfillionaire.

How do you really alchemize a good strategy, whether you’re in a corporation or an entrepreneur — how do you get to your strategy? But ultimately, after you achieve your goals, whether it’s a leadership goal or a financial goal, that doesn’t always just lead to happiness. In fact, for me, it’s just the opposite.

I’ve seen so many people who assume that when they make that goal, they’ll find happiness. But if you don’t go through the other structures of wealth — what I call the five dimensions of wealth — if you don’t have your money or your strategy aligned with the other core dimensions, there’s a good chance you’re not going to find that joy and fulfillment. You’re going to find money.

I’m sure you’ve interviewed and coached a lot of people who need your help because they just assume that when they hit it, they’re going to find it. I can tell you, for me in my twenties — I’ll give you a little bit of my background — I was into Tony Robbins at UCLA, and I was really trying to find myself when a lot of my friends were doing corporate jobs in their twenties, becoming lawyers and doctors. I was just a free spirit, kind of trying to figure things out.

I probably had twenty jobs in my early twenties, but I was a really big fan of Tony Robbins. I’d sit around and put on my Sony Walkman and listen to Tony Robbins every day.

Susan Drumm: So you’ve been a junkie for personal growth for a long time, too.

JP Newman: Oh my god, since I was eighteen years old. I had a dream, and my dream was: if I do Tony Robbins every day, do vision boards, and have these goals, everything’s going to work out just great.

My goal was that by thirty years old I’d have a million dollars in the bank, have my wife, have everything figured out. My story was supposed to be really good — that’s what I said at twenty. There’s this belief, and I even see it now for people in their twenties, that if I just have that money, then everything will be better in my life. That’s exactly what I thought.

I had the car, I had everything kind of planned out. All my friends were having these great corporate lives, and I was spinning through lots of jobs, exploring. And when I hit thirty, I was broke. I was single, living in a cheap apartment with a crappy piece of a car.

It was very humbling, because I didn’t understand how someone could work so hard on their personal growth and not get there. What I realized — and I think you talk about it a lot in your playlist — is that I was going full-force with goals, but I had no meaning behind the goals, and no strategy or roadmap to really get there. I had mapped out every day what I was going to do.

But what I call, in the four dimensions of wealth, “the why that makes you cry” — the things that are absolutely non-negotiable in your life — I thought I had non-negotiables when I said I wanted a Ferrari or I wanted a cute wife. I was naming the things, but I had never gone deep enough as to why those were actually important to me.

Fast forward: in my mid-thirties — I was a late bloomer — I started making money through my real estate company, Thrive FP. I was shocked, because the day they delivered my car — a BMW 645 convertible, the exact car that had been on my vision board forever — I sat in it, and within three minutes I went from excitement to panic.

I actually had an anxiety attack, because I had no idea what this car even meant. I’d spent so many years chasing the vision that when I actually got it, it was stressful, and I had no idea why. I expected to be happy. Why was I in panic? Why was I anxious? What was that about?

Susan Drumm: Yeah. Just to that point — just before you came on, we had a conversation, and it’s in the podcast as well, with Laura Gassner Otting, who wrote the book Wonderhell. What you’re describing is sort of like when you succeed and everything is supposed to be wonderful, and it is, but there’s a dark side to it that’s hell, too. How do you avoid that? It sounds like you were in your own sort of wonder hell.

JP Newman: It was wonder hell. Great on the outside, but absolutely not great on the inside. What I discovered — and it took a bunch of years to figure out, because I had no framework, which is where Fulfillionaire came from — is that I had so many limiting beliefs that were my money stories. My playlist was not a very good playlist, if we put it in your terms.

My playlist came from my grandfather, who said, “Money doesn’t grow on trees.” Like eating all the food on your plate — to this day, I have to remind myself I don’t have to eat all the food on my plate. That was drilled into me as a kid: money doesn’t grow on trees.

The one that really took me down, and I had no idea it existed, was: you can’t have it all. You can’t have your health, you can’t have a happy marriage, and you can’t expect to have money and happy kids. A wheel’s got to fall — you can’t have it all.

So all of a sudden, when money started coming in at a pretty rapid pace… through my real estate company — we own apartments, it’s called Thrive FP, which is for purpose, for profit — we’re a real estate syndication firm that buys apartments in the South and Southwest. We’ve done about two billion dollars of transactions, about twenty thousand apartment units.

But it didn’t start that way. I got a little lucky because I moved to Austin from Los Angeles twenty-two years ago, just when Austin was starting to become awesome. Everybody wants to be here now, but it wasn’t always like this.

I had a hunch that Austin was going to be special. I got here early, the wave crested, and I had enough skill and enough moxie to raise money and start buying these apartments — I caught a beautiful wave. But the money came fast, and my belief system wasn’t where my success was going. So the money started to go up, and—

Susan Drumm: By the way, built from your upbringing. I really think a lot of people don’t explore the mindsets and patterns they’ve adopted from their parents around earning money and spending money. That’s one of the things I see on both sides of the coin — “we just don’t do that,” or “money doesn’t grow on trees.” So what does that belief produce in your life? And “you can’t have it all” — what does that belief produce in your life?

JP Newman: Right. For me, what I realized was that the things going through my subconscious, which I wasn’t even aware of, and which were creating the anxiety, were: am I going to get divorced? Are my friends going to think differently of me? And the big one, actually, was: am I trustworthy? Am I trustworthy with money? I had no experience, so when money started coming in, was I even going to be a good steward of it or not?

When people ask me, “JP, how did you break the cycle of anxiety? How did you actually find fulfillment?” — it started, and this took a long time, with a lot of therapy, work, consulting, coaching, journaling, and meditation. But when I finally realized I was trustworthy and could be a good steward of money, and I built a relationship with money that was trustworthy, everything changed.

To this day, I love making money. Not just because I’m a good steward of it and know what to do with it and how much I need — what I’ve really learned is that giving money, once you know how to receive it, and lighting up people’s lives with it, brings me so much joy. I think of it as currency: I love receiving, don’t get me wrong, but I love giving.

I’m at a place right now where currency is just like a river — it’s a flow. But most people are not in flow with currency. They’re stuck: “I’ll give once I make X,” or “when I’m older, when this happens, I can be a better giver” — and they wait. The secret to currency isn’t giving it all away — it’s letting that flywheel fly between giving and receiving.

My experience is that it creates great joy, for a simple reason: as humans, we’re very social creatures, and what really gives us the biggest dopamine hits isn’t how many more cars or planes or third or fourth homes we can have — it’s how we can impact others. So Fulfillionaire takes you on a journey: how do I get you to go from feeling safe around your money — safety, clarity, good stewardship?

Clarity means you’ve got to have a good roadmap, a plan. Without a map, you can’t go anywhere — we couldn’t find each other if we didn’t have GPS or maps. You need a plan for your money. Once you start to achieve your plan, you need a place to stop: “I’ve had a number, this is what I’m burning per year, this is my dream number in the next thirty-six months, and it’s realistic. It’s not an Instagram dream. I don’t need to become a Lamborghini guy, I don’t need a helicopter or a yacht, and I want to stay married, so I’m good.”

Once you actually have your dream — the why that makes you cry — that’s why it’s called Fulfillionaire. It’s not a financial status; it’s your definition and your autonomy around wealth. Once you know, in your heart, soul, and brain, what wealth means to you, we birth a number for you — your freedom number in thirty-six months. Then, through the wealth pyramid, we track your freedom number, and it becomes a really fun game. You actually get to know what winning feels like.

Who tells you you’ve won? What number is winning, and how do you know you’ve won? When I’ve worked with billionaires, there’s still this fear — you’d think they’ve won, right? No. Unless you deal with that mindset piece — what are you really after? — because they’d say it’s actually not the money or the title or the cars. We’re after a set of emotional experiences that we think the money is going to give us.

Susan Drumm: A hundred percent. But the money doesn’t give you those emotional experiences absent that, right? The money comes as a result of, not a pursuit of. You and I always say: stop chasing a pile and start finding the feeling. What’s the feeling you’re trying to find?

JP Newman: We’re all trying to solve for — we want to feel peace, we want to feel presence, we want to feel safe. Those are the big six. We’re actually not trying to solve for collecting paper and metal, which is the currency — we think the paper and the metal will create the feelings, and they certainly help. If you can’t pay your rent, it’s very hard to feel safe.

But once you align what the money is there to do within the four dimensions of wealth — which I’m about to get to — then you have this great roadmap. I think the most frustrating thing is that when I ask people, because I mentor a lot of them, “what’s your definition of wealth?” — most give me their cocktail story. “I’m going to two-x my company, quadruple my sales, IPO, I’m going to be worth ten million dollars.”

Then there’s the second question: why do you want that? And there’s the second cocktail story — a bunch of thoughts, internal narratives we all create. Just like my Tony Robbins story — I wanted to be thirty with a Ferrari. That was my story. Men create really grim stories, I’ve found, because I’ve mentored a lot of men — amazing storytellers with all these dreams and things they think they want, but it’s not really connected to anything super deep.

Ultimately, when you get to the part of “why do you really want this,” it’s usually an emotion. You get to a why. For me, I’m at the point now where I think about what wealth is to me — wealth is service and leadership. Every time somebody comes to me after my workshop or a podcast and says, “JP, I can now sleep at night. I wasn’t sleeping, I was so worried about my money, and now I can sleep” — I’m sure you get a lot of the same with your coaching work.

Outside of my family, my health, and all the things, that’s service to other people — watching them become givers because they feel safe. That’s my why. Why do I do that emotionally? Because I love human beings. I just absolutely love human beings — it feels, in my body, like deep love and deep joy. So I’m trying to get people to ask: what’s the emotion we’re solving for? What’s your version of it?

The fun surprise is, while a lot of people talk about net worth — I’ve lent out eight hundred million dollars on real estate loans, I’ve seen so many people’s financial statements — net worth is a joke. People make this up.

Susan Drumm: As a scorecard. Sometimes it’s a scorecard to justify why they don’t feel good today.

JP Newman: Right. So the idea is: let’s not focus so much on your net worth, let’s focus on your dream. Let’s birth the number to your dream — how much you need to make a year to live this dreamy life — and then create a financial plan for what you need to make in active income and passive income.

Your active income is what you’re making at work or in your business. Your passive income is what you’re invested in that just brings in mailbox money. Can those two numbers equal that freedom dream number for you? Because when they do — relax.

Susan Drumm: I noticed each one of those things you’re creating is safety. I’m a big believer that you’ve got to create the feeling of safety now, not when that number occurs — because otherwise you’re forever chasing it. How do you help people create the feeling of safety now, so they can let that wealth in and receive it?

JP Newman: This is where I usually start with people. If you’re still having a hard time paying your rent, it’s very hard to create safety. The first question I ask, and I get the most interesting answers, is: how much do you spend a year? What’s your burn rate? Most people don’t even actually know what they’re spending.

I also ask how much they make in a year — investments, salary, take-home pay. A lot of people don’t really know; their financial planner knows, or they get statements, or they think they’re making a certain amount, but they don’t really know. And it’s really hard to create safety if you don’t have clarity.

So the first thing I’d say to somebody who wants basic safety — forget the freedom number for now — is: are you paying your bills? Is there food on the table? Are you feeling pressure at night, or do you feel like the basics are covered? In America, somewhere between sixty and a hundred thousand dollars, you can cover your basics, and everything else becomes upside from there.

I’d really encourage people in the audience, if they’re not feeling safe yet, to just know what they’re spending and what they’re making. Because that will create safety. If you know that no matter what — if it’s a bad market, or you get laid off, you’re good for the next six to twelve months because you’ve saved this much and have this much in investments — that is really empowering. I’d say start there, as step one.

Susan Drumm: Right. So there’s that opportunity to build awareness — getting related to reality, what your spend actually is, what you currently have, and where you actually have freedom to make different choices. That’s the first piece. Now let’s take the other side.

JP Newman: In my workshops, one of the first questions I ask is: how many of you know those two numbers? They’re supposed to know when they come in, and I’d say these are financially savvy people — I’d say about twenty-five percent actually know it when I dig in with them. Most people are living on a hope-and-pray strategy. Money under the mattress, hoping it kind of works out. “I think my financial planner’s got me, but I don’t exactly know what I’m making in my investments.” There’s a lot of that — you think you know, but you don’t exactly know.

Susan Drumm: Yeah. And then there’s this middle piece, right? So the first stage is: do I feel safe enough to cover my basic needs? Great. And then there’s this next piece where you put a number out there, and it seems to always change.

JP Newman: Well, then I get that number, and no — everyone around me is now making more, and the number is moving. It’s the carrot that keeps pulling you along.

Susan Drumm: There’s that phase, and I’d love to hear what you have to say for people going through that stage. And then there’s the wonder-hell stage — “oh my gosh, I have more than I could have dreamed, yet I still don’t feel fulfilled.” What do you say for that third stage?

JP Newman: Let’s focus on the first, then talk about the second. So the first number I call the safety number. Your second number is your current number — it’s just taking a realistic look at where you’re at now.

What I do with people is run a two-day workshop here in Austin, and one of the first exercises we do — because a lot of people can’t get to that “why.” They have some kind of purpose, but they don’t really know what drives them or why they’re doing what they’re doing. They’re too anchored on the number, which keeps moving, and not enough on what’s behind it. What do you think that number is actually going to give you?

So the next thing we do is birth what I call your five dimensions of wealth — this might be a good moment to explain what those are, so you know what you’re solving for. I call it the five P’s. Your money is your prosperity — that’s the first P.

Prosperity is embodied health with embodied wealth, because if you don’t have your health, wealth doesn’t matter. We’ve all heard the expression: a person with a thousand problems, as soon as they have a health crisis, only has one problem.

So how do you anchor your prosperity among the other four P’s? The next is your purpose wealth — your connection to your meaning, your connection to your legacy, your true north. It’s the connection to everything that actually matters to you. I have a feeling you and I both just love uplifting people — I think we both anchor to that.

The second is people wealth, which is really your connection to other humans, but ultimately your connection to love, because as social creatures, most of us get our joy from connecting to others. When I talk about people wealth, the primary relationship is your relationship with yourself — are you good with yourself? That took me a bunch of years to figure out.

Then, are you good with your spouse, your kids, your closest friends, your church, whatever you do — that’s where people wealth comes from. It’s connection to your ultimate inner and outer community.

Then there’s presence wealth. A lot of people talk about “time wealth” — I don’t, because all of us have the same amount of time, whether you’re a billionaire or a pauper. Presence wealth is really about your connection to time and your relationship with it.

As we speak right now, the only thing on my mind is talking to you — nothing’s pulling me. I’m also very clear that talking to you on this podcast is right in the alley of my four P’s, so you’re hitting all of them right now. My priorities are in place — I meditated this morning, did yoga, and I’m comfortable in my body. I think you’re the same way — I can feel it, you’re energetic but also very grounded at the same time, and that feels really good. That’s what presence wealth is — more and more time in that state.

And then the last one, which people don’t talk about, which is crazy, is play wealth. A lot of people work sixty hours a week trying to please their boss — work, work, work. But play wealth is not optional. It’s your connection to your joy, your aliveness, and ultimately your creativity. If you’re not finding things that hit your play wealth, you can’t be a dynamic entrepreneur, you can’t be fluid at work, and it’s harder to connect to your intuition if you’re not using all four dimensions of wealth.

So back to your question — what I’m solving for with people who go through Fulfillionaire: I offer, if you want, to give your audience my first question, which is, let’s build out your five dimensions of wealth, the why that makes you cry, and we birth that in thirty-six months. We don’t go twenty years out — it’s too hard for the brain to go that far. But what would your five-dimensional wealth look like in the next thirty-six months?

Once we’ve established those emotional, non-negotiable things, part two of the exercise is: now that I know what you want, I’m going to ask you another twenty questions, around material things. What material things do you need or want to support the five dimensions of wealth? For instance, if part of your purpose is to be the best dad and husband — for me, my kids are a top priority — I can tell you that when my kids were younger, I took one summer trip every year and spent a lot of money on them.

As I got older, it started small, at Disneyland, but eventually I’d take them to the Four Seasons in Japan. Everything was so curated, and that was such an important thing for me — I’d rather do that than buy a car, to be able to take my family on this deep, cultural, wondrous experience together. So my point is, in my budget, when I’m thinking of the non-negotiable things, taking a family trip every year to a new part of the world, in a way that’s adventurous and luxurious — we do Backroads and spots like that — is really important to me.

Susan Drumm: Backroads are the best, right?

JP Newman: So, at the end of this, with a little AI help — some beautiful friends here in Austin helped me create incredible prompts we’re constantly refining — we birth your five dimensions of wealth and your current number, where you’re at now, which is just figuring out the math. Then we figure out your freedom number, how you get all these things that are important to you, and then we look at the difference.

Let’s say you bring in two hundred thousand dollars a year today, between active and passive income, but the life you actually want to live is a three-hundred-thousand-dollar life over the next three years. If I want to take my kid on that trip, take my wife to the best restaurant at least once a month — whatever your version is — through this wealth pyramid, we’re tracking your progress. If you’re at two hundred thousand but need to be at three hundred thousand, you know you’re sixty-six percent of the way there. You now have a number to aim for, a freedom number.

Through this, it feels like you’ve gone to Vegas and won at the casino — your progression gets mapped out, specifically how much cash you have available to put into new passive-income investments to keep progressing, and how much liquidity you need in your life, between your business, to sleep well at night. There’s no formula — it’s typically six to twenty-four months, but the real formula is whatever makes you sleep well at night. That’s the right answer.

All of a sudden, you have a roadmap. You’re literally on a map, and you win gold coins as you continue to invest — you get recognition from the AI for what you’re doing well, and it also helps identify the areas you can do better in. Can you guess the number-one thing most people aren’t doing well in?

Susan Drumm: Passive income.

JP Newman: Correct. And do you know why?

Susan Drumm: They don’t know how to generate it.

JP Newman: You’re right on. They either don’t have access to the deals or they don’t know how to generate it. But for those who have money — what are they doing instead of passive income?

Susan Drumm: Are they not even saving?

JP Newman: Let’s say they have money, let’s say they save money. You look at the number of people living paycheck to paycheck who aren’t even saving money to have something to invest — there’s something there. But for those who have it, what they’re doing is speculating too much. “My friend knows Elon Musk and Elon liked that deal,” or “here’s this one deal” — and we don’t realize there’s no cash flow for five, six, seven years.

Believe me, I’ve made so many of my own mistakes — I still have deals I’m nine years into and haven’t seen a penny, but one day I’m supposed to get paid. You don’t realize how long five, six, seven, or eight years is, and it really keeps you stuck.

Within the wealth pyramid, we talk about how sometimes you want to speculate — support your best friend’s shampoo company because it’s your best friend, or you think something’s good for the environment, or you want to make a new relationship. But ultimately, I’m a cash-flow real estate guy at the end of the day, and I’m a big proponent that most of your money, once you have it, should be in an area you know something about. Don’t put money everywhere — that’s the second mistake people make. Pick a topic or two you’re genuinely interested in, have conviction in, and get to know it really well.

Once you know your formula for when you’ve got enough liquidity to invest, wait for it to go on sale. Imagine you wanted the hottest dress at Nordstrom’s, and it was four thousand bucks, and you wanted the dress but didn’t want to spend the four thousand — what would you do? I know what I’d do with a jacket: I’d wait for it to go on sale. I used to work at Macy’s as a kid.

So the idea is: get to know a company if you’re in stocks, get to know a couple of real estate deals, pick five or ten things as your thesis — unless you’re dealing with fifty or a hundred million-plus, in which case you need to be diversified. Find a couple of things, wait for them to go on sale, then buy them, and limit your exposure to speculation. If you keep doing that, that sixty-six percent is going to get you there.

I live this game — I’m investing in something I found yesterday, a Walgreens. It’s like a game to me. Every time I put money in, I already know the return, and in my head I already know what it means for my pyramid. And here’s the fun part: your first real win is your active income plus your passive income getting you to your freedom number. Then the advanced game, as you get older and save some money, is getting to your freedom number with just your passive income.

So now your investments, your cash flow, is just there — you don’t have to. So now, guess what that means about work? Maybe I don’t have to.

Susan Drumm: Well, JP, I love the idea, and I could talk to you forever, but we’re bumping up against our time. Here’s the thing about the perspective of it being a game — that was a really important word. It is a game. When you can take the perspective of a game, it loses that tightening that can happen.

JP Newman: A hundred percent. And you want to win at a game, too — you don’t want to take unnecessary risks. But it’s fascinating that people speculate too much anyway.

Susan Drumm: Well, where can people learn more about your work?

JP Newman: If you want to know more about my work, you can go to fulfillionaire.com — f-u-l-f-i-l-l-i-o-n-a-i-r-e dot com, like millionaire, but Fulfillionaire. If that’s too complicated, the same site is at findthefeeling.com, because I know a lot of people can’t spell Fulfillionaire. I do workshops, I have a podcast, and I really try to help people up-level as much as they can.

I think the world right now needs entrepreneurs who are givers — they’re the ones who can have the biggest impact on people. I almost feel like at this point we can’t wait for government to catch up. It’s on each one of us to do what we can — it could be our time, it could be our money, it could be bigger or smaller. It’s the biggest formula for your own happiness, and it’s the greatest way to help uplift humanity. That’s my passion.

Susan Drumm: I love the phrase Fulfillionaire — that is really what it’s all about. It’s actually not about the million, it’s about what am I doing to be fulfilled.

JP Newman: Not status. And one last thing about the game that’s really fun, which we talk about — it is a game, but nobody tells you the rules of it. The tax code is part of the game. There are all these things that are the game, but no one teaches us the game.

A lot of people say, “well, I don’t want to play that game,” but if you say that, you’re still playing the game — you’re just not winning at it. It’s like playing Monopoly and no one told you how to play, and you’re all over the place, but you’re still in the game. The government doesn’t let you out of the game, and neither does society. So why not, through good coaching, great programs, education, and podcasts, get good at learning the rules of the game? Because once you know the rules and can play it well, the game gets pretty fun.

Susan Drumm: All right, JP. Thank you so much for joining us today. If you loved this episode, definitely also watch Laura Gassner Otting’s episode, where we look at what happens when you reach the stage of wonder hell.

Let’s all lead the way. Hope you enjoyed today’s episode, and I’d like to point you to the next important step: hit the subscribe button and the bell to get notified when we release new content. I’ll see you on the next episode of The Enlightened Executive.