There’s an invisible battle most entrepreneurs don’t realize they’re fighting. It’s not about interest rates, market timing, or portfolio allocation. It’s about mindset.
Specifically: Old Money vs. New Money.
And I’ve lived both.
Old Money: The Architecture of Enduring Wealth
Old Money thinks in generations. They think about control, legacy, and sustainability. They mitigate risk by leveraging experts. They understand the power of contracts, the importance of attorneys, and the necessity of saying “no” more than they say “yes.”
Old Money knows that not all opportunities are created equal.
They value staying power over flash. They invest in businesses with history, teams with track records, and ventures that have weathered storms.
Old Money teaches their children about money. They talk about wealth openly at the dinner table. They build structures—family constitutions, trusts, legal frameworks—that protect, preserve, and perpetuate.
Old Money is focused. They build a solid stream of cash flow before diversifying. They discern opportunity from distraction. They protect their energy, not just their assets.
New Money: The Hustle and the Hazard
New Money? They hustle. They grind. They say “yes” because they’re afraid to miss out. They self-identify as “serial entrepreneurs”—a phrase that too often masks a lack of focus.
New Money starts without a network. They attract people who may have helped them initially but eventually become anchors—hangers-on who drain resources, limit growth, and sometimes even sabotage success.
New Money doesn’t always know their value. They’re seduced by the show: fancy cars, exotic trips, exclusive clubs. They confuse accumulation with wealth. They invest outside their expertise. They allow high-rollers to sell them risky deals because those high-rollers make them feel important.
They’re too busy to build a proper financial team. And that oversight? It costs them far more than they save.
New Money is addicted to activity over strategy. They chase multiple streams of income before solidifying one. They neglect contracts. They people-please. They say yes to deals, to distractions, to drama.
They don’t talk about money with their family—until it’s too late.
How do I know? Because I lived it.
My New Money Story (The Expensive Way I Learned)
In my 20s, I hired college friends—not because they were competent, but because they were convenient.
I lacked leadership. I lacked the courage to say no. I said yes to nearly every investment that came my way: real estate, oil and gas, bridge financing, starting new businesses while the infrastructure of my core business was still shaky.
I confused luck for skill.
I had too many LLCs. Too many meetings I didn’t love. I was spread thin. And my skill—the one that could have scaled the business—was buried under my inability to focus.
Greed hijacked my decision-making. I started a fund. I wasn’t a fund manager. I could raise money, sure—but I wasn’t in the trenches. And it cost me: not just money, but time with my family. It cost me peace. It cost me health.
Each “yes” was a “no” to my family. A “no” to date nights. A “no” to my kids. A “no” to presence. All because I was trying to fill the gaps of insecurity with accolades, awards, and more, more, more.
It didn’t create more wealth. It just created more work.
More stress.
Less rest.
Less creativity.
Less purpose.
I bought a P&C firm. I started a mortgage company. And in doing so, I had less time for the work I loved most: teaching, speaking, writing. And I wasn’t creating the best companies because I was spread thin.
Why? Lack of clarity. Lack of vision. Scarcity disguised as opportunity.
I said yes to fill a void. I didn’t know it then—but I was living in the New Money Mindset.
In my 30s, I cleaned up the mess. I reclaimed time with my kids. I took annual trips with my wife. I went fly fishing. I learned to make a proper latte. I bow hunted. I wrote poetry (yes, poetry). I pursued comedy. I built one business, one Inc. 500 8-figure business. I simplified.
I built a life I don’t want to retire from.
And that’s wealth.
So let me ask you:
- Who is on your team? Are they qualified or just familiar?
- Who protects you from the wrong yeses?
- How do you vet opportunities? What’s your due diligence process?
- Are you saving money by skipping the right professionals—and paying exponentially more for that mistake later?
- Are you building a lifestyle along the way, or just hoping to buy one at the end?
Wealth isn’t about grinding until you burn out. You don’t have to be old money to learn from the process, ideology, and principles they live by.
It’s about building wisely. It’s about focus, clarity, and stewardship.
It’s about learning to say “no”—so you can fully say “yes” to the life you love.
