Reduce Capital Gains. Or Eliminate Them Entirely.

There are a variety of techniques to potentially reduce capital gains and realize tax savings on the sale of highly appreciated assets, such as a concentrated stock position, impending sale of a business or asset, or other windfall. Some advanced strategies can even eliminate capital gains taxes entirely. A brief primer appears below.

Strategy #1: Installment Sales
For use with these asset types: business, real estate
There are three types of installment sales that can help to spread capital gains and other taxes owed over a period of years rather than being realized all at once. They are:
• Direct installment sale
• Structured installment sale
• Installment sale to a business trust

Strategy #2: Exchanges
For use with this asset type: real estate
This strategy allows sellers to defer capital gains resulting from a real estate sale by using the proceeds from the sale to purchase another like-kind property for personal, business or investment purposes.
• IRC 1031 Exchange
• IRC 721 Exchange
• DST - Delaware Statutory Trust Strategy

Strategy #3: Charitable Remainder Unitrust (CRUT)
For use with these asset types: securities, business, real estate
Using this strategy, tax-deferred sale proceeds are used to establish a trust that spreads taxable income to beneficiaries over a specified term, with the assets remaining at the end of the term paying out to qualified charitable organizations.

Strategy #4: Qualified Opportunity Zone Fund
For use with these asset types: securities, business, real estate
Investing sale assets in economically distressed regions can result in preferential tax treatment.

Strategy #5: IRC Section 1202
For use with C corporations.
For founders of C corporations, up to $10 million may be excluded for income taxation on the sale of qualified small-business stock held for more than five years.

Advanced strategies are also available that vastly outperform typical garden-variety tax-loss harvesting and direct indexing. 

A FlexIndexing strategy, for example, can generate $200k, $500k, or $700k of yearly "losses" for every $1m invested, offsetting overall gains to the portfolio. 

This strategy can be used to:

• Increase cost basis in the portfolio (minimizing tax exposure), or 
• Used in one portfolio to allow rebalancing or exiting positions in another portfolio, or 
• Receive a windfall from elsewhere that would otherwise trigger tax liability. 

These strategies are all part of the private market strategies we offer through a referral to a larger, more exclusive RIA. 

Given your circumstances, you may also find value in our estate tax mitigation techniques.