The summit ยท Tax deferred strategies
Most sellers meet the tax bill at closing. Some make it wait.
More than forty strategies exist to defer, reduce, or sometimes eliminate the tax on a sale. Which ones apply to you depends on answers only you have.
The part nobody tells you
The tax bill is a default, not a law of nature.
Capital gains tax is what happens when a sale is structured the ordinary way. It is the default outcome. Defaults are what you get when nobody planned.
The strategies that change it are not loopholes. They are built on provisions that have sat in the tax code for decades. They go unused for a simple reason: preparing a return is a different profession from structuring a sale, and most sellers only ever meet the first one.
The most expensive sentence in any sale: "we'll deal with the taxes after closing."
Where the stakes are biggest
Four sellers who should not use the default.
Selling a business
Decades of work converts into a single taxable event. This is the largest check most owners ever write to the IRS, and the one with the most alternatives to writing it.
Selling investment property
Landlords who want out of the roof calls without handing a large slice to taxes. A 1031 exchange is one path. It is not the only one, and it comes with a treadmill of its own.
Concentrated stock or crypto
A position that grew for years, now too large to ignore and too taxable to unwind casually. There are ways to diversify that do not start with a full-price tax bill.
A home with a large gain
The exclusion covers $250,000 for one owner, $500,000 for a couple. Bay Area gains routinely run past it, and most owners never hear what can be done about the rest.
The window
Why this conversation happens before escrow, not after.
Almost every deferral structure shares one rule: it has to exist before the sale becomes binding. Sign first, and the options collapse from many to almost none.
Some structures take weeks to put in place. A few take longer. The earlier the questions get answered, the more of the forty-plus options are still on the table. That is the entire reason this page asks questions instead of listing strategies.
No strategy is right for everyone, and some sales are best left on the default. That is a real answer too, and you would hear it plainly.
How it works
What we actually do.
- 01
You answer the questions
About a minute. What may be sold, where you are in the process, who is already involved. No account numbers, no documents, no exact balances.
- 02
We match facts to strategy families
We work with a national team of tax strategists whose entire practice is this. They work alongside your CPA, not around them, and they bring the full menu instead of the one product someone happens to sell.
- 03
You hear the honest answer
Which strategies deserve a serious look, what they cost, and what they require of you. Sometimes the answer is that the default is fine. You will hear that too.
On Point Finances is a licensed insurance agency, not a tax or legal adviser. Tax strategies are designed and implemented with independent tax and legal professionals. Nothing on this page is tax advice, a guarantee of any tax outcome, or a recommendation. Every strategy has real costs and requirements that are disclosed before any commitment.
Fair questions
Asked by everyone who hears about this.
Is this legal?
Yes. These strategies are built on long-standing provisions of the federal tax code, used openly for decades. Nothing here involves secrecy or offshore arrangements. If a strategy only works when nobody looks at it, it is not a strategy we would bring to you.
Why has my CPA never mentioned this?
Preparing a tax return and structuring a sale are different professions. Most CPAs see a large one-time sale a handful of times in a career, and the specialists we work with do this every week, alongside your CPA rather than around them. A good CPA stays in the loop the whole way.
When is it too late?
Usually once the sale becomes binding, and sometimes earlier. Most deferral structures must exist before closing, and some take weeks to set up. The earlier the conversation happens, the more options are still open.
What does it cost?
It depends on the structure and the size of the sale. Every strategy has real costs and requirements, and you will see them plainly before any commitment. If the tax saved does not clearly outweigh the cost, you will hear that too.
Your next step
Answer first. Decide later.
The questions take about a minute and ask for nothing sensitive. They tell us which of the forty-plus strategies deserve a look at your situation, while the window is still open.