Why Most People Fail With Money—and How to Avoid It

When it comes to money, most people live in two extremes: underwhelmed or overwhelmed.

They feel underwhelmed when they hear the same tired advice: save more, defer taxes, lock money away, pay off the mortgage, spend less, and hope compound interest rescues them.

Then they swing to overwhelmed. Social media shouts conflicting rules at them like a carnival barker: buy new, never buy new, write off your dog, grind until you drop, “the rich always do this… the rich never do that.”

So which is it? Who’s right and who’s wrong?

The truth is that while a few foundations apply to everyone, the rest depends on your plan, your vision, and what I call your Investor DNA.

Start Here: You Are the Asset

The biggest shift you can make is realizing you are the greatest asset. Your ability to create value is the engine behind every dollar you’ll ever earn.

Any advice that drains your energy, creativity, or capacity to produce is the wrong advice for you.

If watching the stock market makes you queasy, it’s not your path. If real estate feels like a constant headache, don’t force it. And if running a business is destroying your life, it’s not your game to play.

There’s no single investment that’s right for everyone. For entrepreneurs, this is doubly true.

Start with yourself. Grow your skills. Expand your value. Money follows value, not the other way around.

Automate and Build Liquidity

Once you’ve embraced yourself as the asset, the next step is automation.

Pay yourself first and remove friction from saving. Set up a “sweep” account at your bank (or at LiveCurrence.com) that automatically moves money into savings.

The goal is six months of expenses in liquidity—accessible but not at risk. This could be money markets, CDs, properly structured cash value life insurance, or even gold and silver.

With something volatile like Bitcoin, count every two dollars as one to keep perspective and avoid surprises.

Liquidity buys you:

• Peace of mind.
• Options when circumstances change.
• The ability to seize opportunities and profit from day one.

Transfer Risk, Don’t Shoulder It Alone

When it comes to risk, you only have two choices: retain it or transfer it.

Too many people “self-insure” by hoarding cash for every possible disaster. That’s expensive and limiting.

A better approach is to pay pennies on the dollar to let billion-dollar companies carry catastrophic risks.

Insure the big stuff:

• Liability on your home and cars
• An umbrella policy
• Disability insurance with a longer elimination period
• Properly structured life insurance
• High-deductible health coverage paired with a health savings account

Business owners should consider a business owner’s policy (BOP) policy for liability. Skip the nickel-and-dime coverage like ultra-low deductibles or short elimination periods.

And don’t forget your estate and legacy planning. A will outlines your wishes. A trust avoids probate and preserves privacy. A living will defines your healthcare preferences, and a power of attorney lets someone you trust make financial decisions if you can’t.

For entrepreneurs, the right entity matters too.

• An LLC provides liability protection in partnerships
• An S-Corp helps solo owners take cash more efficiently
• A C-Corp makes sense if you plan to raise money or eventually sell

Taxes: Stop Tipping the Government

This is where most business owners are bleeding. Odds are you’re overpaying, not because your accountant is lazy, but because they’re overloaded. Many crank through 800–1,000 returns a year, leaving little room for strategy.

What you need is a proactive tax strategist and, if you’re over a million in revenue, a tax attorney.

The common mistakes? Spending a dollar just to save 37 cents in tax. Buying things you don’t need because “it’s deductible.” Letting the tax tail wag the dog.

Instead, look for tax arbitrage—where spending a dollar brings back more than a dollar in value.

This could be done properly through land conservation easements if you own the land, or through legitimate art strategies.

Yes, maximize deductions. Most people already cover the basics: paying your kids, renting your home to your business under the Augusta Rule, home office, and business travel.

But many miss the bigger levers like R&D credits, Section 199A for qualified business income, or Section 1202 that allows $10 million of tax-free income from selling a business.

The key is to meet quarterly with your tax team. Tax planning isn’t an April exercise—it’s a year-round conversation.

Investing: Focus First, Diversify Later

Forget gambling. Forget hype. If you can’t explain it simply, don’t invest in it.

The best investments align with your Investor DNA:

• Core Values: What matters most to you.
• Core Competencies: Your strengths and expertise.
• Core Drivers: What fuels you.
• Core Focus: Where you say “yes” and protect your time.

When you align money with who you are, you sidestep the shiny-object syndrome that drains wealth and energy.

Build toward financial independence by creating enough cash flow from assets to cover expenses.

Focus on one cash-flowing class—real estate, royalties, a business—until you reach independence. Only then does diversification make sense.

Cash flow beats accumulation. Stop relying on “buy, hold, and pray.”

The Basics That Move the Needle

1. Automate savings and build liquidity.
2. Transfer catastrophic risk.
3. Get your estate and entity structure right.
4. Build a proactive tax team.
5. Invest in alignment with your Investor DNA.
6. Focus on cash flow until financially independent.

Pick one action a week. Bite-sized steps create massive momentum over time.

Your Next Step

This isn’t about decades of sacrifice. Most of what you’ve been taught about money is noise. The real work is simpler, faster, and aligned with the life you want to live today.

To get access to tools and education, click here and tell us a little about yourself.

If you have more time than money, dig into the workbooks, tools, and assessments we’ve built.

If your business is past $350K in revenue, book a one-on-one discovery session and we’ll map out your personalized path to independence.

The penalty for following broken financial philosophies is permanent. But the reward for aligning your plan with who you are is freedom—sooner than you think.

It’s not your fault you’ve been misled. But it is your choice what you do now.