I spent several hours on a call yesterday with a couple who found me through YouTube.

They were trying to be more tax-efficient with the sale of a business they’ve spent 30+ years building.

That turned out to be just the tip of the iceberg:

• Portfolio was 100% equities, heavily tilted to tech and growth
• No clear plan for tax-efficient retirement income
• No trust structure in place for their kids
• Missing basic estate planning tools like ILITs

Whether someone has $3M or $30M, I keep seeing the same pattern:

people who never hire specialized professionals are missing key pieces of their puzzle.

In this case, the tax issue was the most glaring.

With their level of capital, it’s feasible to harvest significant capital losses over time, which can be used to offset gains from a large business sale — instead of accepting a one-year tax bloodbath.

When they asked their CPA and advisor friends about the tax-aware long/short strategies I talk about on YouTube, the response was consistent:

“Never heard of that. Don’t know anyone who does it.”

So their question to me was:

“If this is legitimate, why hasn’t anyone we know ever mentioned it? How do we trust you?”

Here’s the simple, non-emotional answer.

If you have $30M+, you’re likely in the top ~0.05% of the U.S.

Most CPAs and advisors spend their entire careers serving the other 99.95%.

They’re not incompetent.

They’re just not operating at the extreme tail of the distribution where your problems — and opportunities — live.

For this couple, the math was straightforward:

• With $30M+ invested, it’s possible to realize millions of dollars in capital losses over time
• Those losses can materially offset a $10M business-sale gain
• Instead of reacting to taxes, the strategy is designed around them

None of this is magic.

It’s in the tax code.

It’s used by large pools of capital every day.

It’s just not part of the standard toolkit for most retail advisors or tax preparers.

If you’re in the top 0.05%, advice calibrated for the other 99.95% doesn’t magically scale up.

Your problems are different.

Your opportunities are different.

Your strategy has to be different.

If you’re facing a seven- or eight-figure liquidity event and your current “plan” is simply, “You’ll owe a lot of tax that year,” that’s not a strategy.