From the front seat of a Bentley to the back room of a tax strategist’s office—here’s what actually matters.
“So… where’s all the money going?”
That was the question I asked myself one Tuesday afternoon after staring at the dashboard of my portfolio like it was the cockpit of a private jet I didn’t know how to fly.
I was sitting in my home office, staring at three monitors like some kind of Wall Street Batman, when I realized—despite having a solid net worth and a spreadsheet packed with green cells—I wasn’t entirely sure if I was wealthy… or just busy owning stuff.
Wealth management, it turns out, isn’t about having money. It’s about keeping it, growing it, and—most importantly—not losing your mind over it. And trust me, if you’ve ever tried to juggle multiple income streams, real estate properties, a few LLCs, and a 24/7 news cycle screaming recession, you know exactly what I mean.
Let’s break it down. No jargon. No fluff. Just the stuff that actually matters when you’ve got more than a little skin in the game.
1. Asset Allocation Isn’t Sexy… But It’s the Whole Game
I used to think I could outsmart the market. Timing entries, exits, trying to catch the next unicorn IPO. It was like trying to win at poker with a mirror behind me and a martini in my hand. 🍸
What changed? A dinner with a family office guy. Real old-money type. The kind that sips Bordeaux older than my son.
He told me:
“You’re not trying to beat the market. You’re trying to survive it, decade after decade.”
That night, I restructured everything. 40% equities, 20% bonds (laddered, of course), 20% real estate, 10% private placements, 10% cash/cash equivalents. Boring? Maybe. Effective? Like a Volvo in a demolition derby.
Diversification doesn’t mean owning a bunch of stocks. It means having different horses in different races. Across time zones. Across risk levels. Across liquidity.
2. Taxes: The Legal Theft That’s Optional (If You Plan Ahead)
Ever made a pile of cash on something—maybe a business exit or a juicy real estate flip—only to watch Uncle Sam show up like he owns 35% of your soul?
Yeah. Me too.
Here’s what the ultra-wealthy know that most people don’t:
It’s not what you make. It’s what you keep.
Trust structures. Charitable remainder trusts. 1031 exchanges. Defined benefit plans. These aren’t loopholes. They’re levers. You just need someone who knows how to pull them without setting off alarms.
I set up a charitable trust one year—not because I wanted to be a saint, but because it let me defer a boatload of taxes while funding scholarships for kids who actually deserve a shot. Win-win.
Bottom line: If your CPA isn’t proactively pitching tax-saving strategies, you don’t have a CPA—you have a historian.
3. Liquidity Isn’t Just About Emergencies—It’s About Opportunity
A lot of high-net-worth folks I talk to have everything locked up tighter than a Vegas vault. Private equity, long-term real estate, timberland in Oregon… you name it.
Here’s the problem: opportunity doesn’t wait for your capital to unfreeze.
When March 2020 hit, and the markets fell like a drunk on roller skates, I had cash. I picked up discounted assets while others were scrambling to get liquid. That wasn’t luck. That was strategy.
Pro tip: Keep 6–12 months of personal and business expenses in boring ol’ cash. Then keep a war chest—just enough to say “yes” when the world says “SALE.”
4. Your Network Is Your Net Worth (Cliché… But Still True)
Let me tell you something real: the best deals I’ve ever made didn’t happen in boardrooms or on Zoom. They happened on golf courses. At barbecues. Over late-night bourbon with other weird, wealthy insomniacs.
I once got in on a ground-floor investment in a fintech startup—not because I was a genius—but because I played paddle tennis with the founder’s cousin.
The rich don’t cold-call. They refer. They whisper. They hand-shake behind closed doors.
If you’re not spending 10% of your time building relationships with other high-caliber humans, you’re leaving money—and access—on the table.
5. Legacy Planning: Because Caskets Don’t Have Pockets
This one’s a little grim, but let’s be real—none of us are getting out alive. And if you’ve built real wealth, you’re either going to leave it behind intentionally… or leave a mess.
I watched a friend’s estate get shredded because he had a will from 2004 and thought that was enough. It wasn’t.
Set up trusts. Talk to your kids. Educate them, don’t just write them checks. If you built it, they need to know how to keep it.
My own setup includes a family governance plan, quarterly financial education sessions for my kids (yes, even the artist one), and—yes—a clause that cuts them off if they pull any TMZ-worthy nonsense.
6. Don’t Just Manage Wealth. Enjoy It.
This one took me the longest to learn.
You can hoard money like it’s toilet paper in a hurricane, but what’s the point if you never use it?
I’m not talking about buying gold-plated jet skis. I’m talking about intentional spending. Experiences. Freedom. The ability to say “no” to things that don’t matter and “hell yes” to things that do.
Take the trip. Buy the art. Start the foundation. Write the weird book that’s been bouncing around in your head for a decade. That’s wealth.
Final Thoughts: The Quiet Flex
Here’s the deal, friend: wealth management isn’t about flexing on Instagram. It’s about quiet control.
Control over your time. Your risks. Your future. Your impact.
If your calendar is full of people you don’t like, meetings you don’t need, and assets you don’t understand—what are you actually managing?
Take the time. Build your team. Stay curious. And once in a while, pull the trigger on something that scares you just enough.
We didn’t come this far just to spreadsheet ourselves into oblivion.
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Ready to stop working for your money and start having it work for you?
Cool. Let’s get to it.
(And hey—maybe pour yourself a nice glass of something tonight. You’ve earned it. 🥃)