I Felt Broke for Years, On Purpose. Here’s Why It Made Me Rich

There’s a cruel paradox when it comes to money:

If you wait until you're rich to start behaving like a wealthy person, you may never get there.

The habits, structures, and systems that build wealth aren't flashy.

They don't show up on Instagram.

And most of them feel pointless when you don't have much to your name. Just like Daniel-san thought Mr. Miyagi's "wax on/wax off" exercises were pointless.

But here’s what nobody tells you:

It’s not about how much money you have today. It’s about how you treat the money you do have.

Below are five strange, annoying, and counterintuitive moves I made before I had real money. They weren’t sexy. They didn’t impress my friends. But they fundamentally changed my behavior and years later, they’re the scaffolding my wealth is built on.

#1. Open MANY Bank Accounts So You Never Feel Rich

I’m the kind of person who burns through cash like it’s radioactive. If I had $5,000 in one account, I’d find a way to spend $4,999.

So I started creating friction.

I opened six bank accounts. Eventually, ten. Some at big banks and some at online banks like Wealthfront.

Why? To fragment my money so I never felt rich.

Each account had a purpose: bills, emergency fund, investments, guilt-free spending, taxes, and savings. Seeing $1,000 in an account labeled "Spending" feels different than seeing $10,000 in one big pot. You act poorer, which is the point.

It forces discipline through structure, not willpower. And thank goodness, because I have zero natural willpower.

Yes, it's annoying. But it works like hell. I still use this setup today.

#2. Buy Illiquidity On Purpose

Most people obsess over "access" to their money.

I did the opposite: I started trapping my money.

I bought into illiquid investments on purpose.

At first, when I had very little money, I'd buy things I could afford, like CDs at my local bank. Then, that grew into funds and REITs. Eventually, bigger purchases like actual real estate. Anything that made it harder for me to pull cash out on a whim.

Why?

Because when your money is locked up, you stop fantasizing about spending it. You stop checking your balance every day. You let time do its compounding magic.

This isn't a mindset trick. It's a structural override. It forces delayed gratification by design.

And while everyone was jumping from meme stocks to NFTs to the latest hot tip, much of my money was off-limits. Quietly growing.

Yes, I still put money into NFTs or memes, but I did it in a structured way as you'll see below.

#3. Assign a “Time Horizon” to Every Investment

This changed everything for me. This one strategy alone is responsible for many millions in net worth.

Any time I bought an asset, I gave it a time lock.

Bitcoin? 5 years.

Gold? 5 years.

High-conviction stocks? Minimum of 3 years.

I would literally write the hold period in a note. Once I did that, I stopped checking the price. I stopped flinching during dips. I stopped chasing.

Why? Because I'd made a deal with myself: I'm not even allowed to think about this money for X years.

This simple move rewired my relationship with volatility. No more panic selling. No more FOMO chasing. Just patience.

And you know what? Those long holds paid off big time.

#4. Give Yourself Rich People Problems Early

You don’t need millions to think like someone who’s managing millions.

So I gave myself rich people problems before I was rich.

• I set up a trust for my kids.

• Created a SLAT (Spousal Lifetime Access Trust).

• Worked with a CPA.

• Started my estate plan.

Was it overkill? Yes. When I started giving myself these “rich people problems,” I barely had any money!

Was it expensive and painful? Absolutely. Making those payments to professionals (attornies, accountants, etc) hurt like hell.

What hurt even more was my ego because I felt silly for setting up a trust and funding it with almost no money.

But here’s the trick: You can’t keep thinking short-term when your financial infrastructure is built for the long game.

These moves forced me to think generationally. They made me ask, "What happens after I'm gone?" Not, "What can I buy this weekend?"

That mindset shift was priceless. And once it clicked, I couldn’t go back.

#5. Create Buckets for Your Net Worth

Most people just track their net worth as one number.

I broke mine into buckets. Here’s what it looks like today:

• 30% Real estate (rentals, home, REITs etc)

• 20% Cash / liquid

• 10% DIY investments (stocks, trades, etc.)

• 10% Managed by a planner/banker

• 10% Crypto (Bitcoin, ETH, Solana, etc.)

• 7% Watches & art

• 5% Private deals (pre-IPO, Reg A, CF)

• 5% Charity

• 3% Precious metals

These aren't magic numbers. They're guardrails.

If crypto starts popping off and I feel the itch to buy more? I check the allocation. If I'm already at 10%, that's it. No matter how much FOMO I'm feeling. If I think a particular coin will go much higher, I must exchange one coin for another.

Buckets force you to operate from a system, not emotion. They also help you rebalance annually based on your goals, preferences and growing net worth.

Most importantly, they make your personal economy resilient.

You don't go all-in on one thing. You're not just riding one wave. You're creating a web of stability.

Final Thought:

Wealth isn’t a destination. It’s a system.

And you don’t need a million dollars to start building that system. In fact, I believe you must build that system now, regardless of the dollar amount you have.

You need structure. Friction. Rules. Guardrails.

These habits make you feel broke while they quietly (eventually loudly) make you rich.

If you're not rich yet... the best thing you can do is start acting like someone who already is. Warts and all.

Because once the money shows up, it’ll have no choice but to fall in line. Remember, wealth is about you being in control, but if you don’t set the systems up now, money will control you.

Double D

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