Which Tax Strategies Are Too Risky?

It’s become a dominant force in decision-making. I’ve had countless conversations with individuals contemplating big financial moves—selling their practice, shifting real estate, reallocating capital—and their primary motivator isn’t freedom or strategic investment.

It’s avoiding taxes.

I’m not against paying less in taxes when it’s done prudently. But when your entire investment strategy revolves around tax avoidance, you’ve let the tax tail wag the dog.

The Rise of Risky Tax Strategies

There’s an entire cottage industry built around this mindset. Promoters—often smooth-talking, credentialed, and well-branded—offer schemes that promise dramatic tax savings through constructs like:

• – Deferred Sales Trusts
• – Monetized Installment Sales
• – Opportunity Zones
• – Captive Insurance Companies
• – Conservation Easements

Sure, some of these have legitimate applications. But many are riddled with complexity, hidden fees, and regulatory landmines.

Worse, you’re often giving up control of the capital you’ve spent decades earning.

And let’s be honest: If the IRS comes knocking, do you really think that promoter is going to stand beside you?

Most of the time, you’ve already signed the paperwork releasing them of any liability. They’ve made their money, and you’re left holding the bag.

When Tax Savings Become Costly

Many of these structures are pitched as “IRS-blessed,” but being on the IRS’s listed transaction radar should give you serious pause. These are red flags that invite additional scrutiny—not something you want in the later seasons of your career.

Why risk your nest egg for a perceived short-term win?

Especially when you consider that current tax rates are at an all-time low historically. Trying to defer or avoid taxes at this stage could backfire. Pay the tax, retain control of your capital, and focus on what really matters:

Getting your capital to produce dependable, recurring income that supports your lifestyle, without you having to work.

That’s what should drive your decisions.

The True Measure of Wealth

Don’t be fooled by what a spreadsheet, balance sheet, or social media “expert” tells you. Net worth is not a trophy—it’s a tool.

What matters isn’t the paper value of your business, real estate, or portfolio. What matters is: How much replacement income can it produce?

That’s what we focus on inside Freedom Founders. Because at the end of the day, your wealth should be measured by the quality and reliability of the income it can generate, not just the number on your net worth statement.

You can learn more about measuring wealth and a breakdown of how to look beyond surface numbers here.

Get Advice That’s Agenda-Free

If you’re evaluating a tax mitigation strategy, you need more than salesmanship—you need wisdom.

Surrounding yourself with advisors who don’t have a financial stake in what you choose to do has never been so vital. You need outside eyes, not insiders with a vested interest. That’s how you protect yourself.

I recently emphasized this and other ways to protect your capital in an article on The Street Roundtable: Seasoned Entrepreneurs Warn…

Most people are getting sold, not advised. They’re being preyed on at the most vulnerable and valuable stage of their financial lives.

Don’t fall for it.

Guard Your Freedom

You’ve spent years—decades—working hard, sacrificing, building something meaningful. Don’t lose it all at the finish line.

Tax avoidance shouldn’t come at the cost of risk, complexity, or loss of control. Instead, focus on sound investment principles.

Keep your capital in assets you understand.

Generate steady, predictable income.

And never outsource your financial freedom to someone with a slick pitch.

It’s your freedom. Guard it well.