TAX-LOSS HARVESTING FOR DOCTORS

Keep more of what you earn with tax-smart investing built for practice owners

See how our strategies can help you offset the capital gains in your practice sale or other large liquidity events.

How it works:
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In this example, let's say our client has $1 million and wants to track the S&P 500 while also harvesting tax losses.

We help them invest the $1 million into a basket of 200 to 300 stocks expected to match the index’s performance.

Their portfolio keeps the winning securities and sells those that have declined below the purchase price, replacing them with a close alternative.

So, let’s say for example Visa was one of the stocks that declined since our client bought it. We’d sell it and harvest the losses.

Then we would replace it with a stock like MasterCard.

Our goal is to harvest losses on decliners to offset capital gains from other investments, while buying new stocks to keep tracking the index.

How it works for a large liquidity event:

To accelerate these losses, we would invest the same $1 million in a basket of stocks, but also borrow against the investment to create two “extensions” — longs that bet on the stocks and shorts that bet against them.

For example, in a 140-40 portfolio, our client’s portfolio would be going long and short by an additional $400k, respectively. The investment is now 140% long and 40% short, which can amplify returns while providing more opportunities for tax losses to harvest.

Our client’s net exposure would still be $1 million, or 100% net long.

This amplifies both the losses and the gains relative to our client’s overall position. It also generates losses on the shorts that go up in addition to the longs that go down, so there is greater potential for losses to harvest.

Earned Client: Orthodontist & Practice Owner, Age 67, in San Francisco, CA

Annual Income: $400k from practice

This is one illustration to show how tax-loss harvesting has the potential to offset capital gains from the sale of a business. It does not factor in transaction costs or wealth management fees. Earned Wealth Advisors has other clients whose tax-loss harvesting results vary across a wide range depending on their individual circumstances, particular investments, and the timing of transactions. Investing strategies, including tax-loss harvesting, entail risks including missing out on potential market gains. Results cannot be guaranteed.

A real client case study:
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In 2023, our client funded an account with $1.7M. We implemented a tax-loss harvesting strategy to generate losses.

The client sold their practice in 2024 for $1.6M, realized capital gains, and invested $1.1M more.

We harvested a total of $1.4M in losses, offsetting $1.4M in capital gains and saving $420k in taxes in 2024.

Built for the complex financial life of a doctor

Tax-smart investing is most powerful when it's coordinated with a major financial event. Here are the moments where Earned can make the biggest difference.

Selling your practice

Exercising stock options

Selling real estate

Diversifying concentrated stock

Managing large taxable accounts

Preparing for retirement income

Offsetting rebalancing gains

Practice distributions

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Turn tax complexity into opportunity

Earned After-Tax Alpha measures the value created through integrated, continuous wealth and tax management—helping doctors keep more of what they earn.

~3.7%
(Earned YTD,
net of fees)
0.5–0.7%
Highly variable;
case studies show
$420k–$520k+
per event
~1.5%
Multiplicative effect
of the above
Highly variable;
case studies show
$40k–$57k
per year
from entity optimization
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