If you’ve built substantial wealth, capital gains taxes may quietly erode far more of your investment returns than you realize.

The good news? The tax code offers legitimate ways to potentially help minimize that bill – if you know where to look.

Here are three high-impact areas where strategic planning may help minimize your capital gains tax.

1. Investment-Related Expenses
Certain advisory fees, margin interest, and other investment-related costs may qualify for deductions or adjustments, depending on how they’re structured and reported.

2. Cost Basis Adjustments
Adding eligible purchase, improvement, and transaction costs to your cost basis may help minimize any taxable gain when selling investments or property.

3. Selling Costs on Real Estate
Commissions, staging and certain closing costs tied to a property sale may be deducted from any potential gain.

Each of these opportunities may come with complex rules, thresholds, and IRS definitions.

That could be why affluent investors turn to fiduciary financial advisors and wealth managers – not just for investment management, but for tax-forward wealth strategies that may integrate with their CPA’s planning.

Wondering how to get help designing a personalized capital gains tax strategy? Try SmartAsset’s no-cost tool to find vetted financial advisors serving your area, each legally bound to work in your best interest. Get your financial advisor matches today. 

Try SmartAsset’s Financial Advisor Matching Tool

Hire a pro. Find and compare vetted financial advisors serving your area, each legally bound to work in your best interest.

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This is not an offer to buy or sell any security or interest. All investing involves risk, including loss of principal. Working with an adviser may come with potential downsides such as payment of fees (which will reduce returns). Past performance is not a guarantee of future results. There are no guarantees that working with an adviser will yield positive returns. The existence of a fiduciary duty does not prevent the rise of potential conflicts of interest.

SmartAsset.com is not intended to provide legal advice, tax advice, accounting advice or financial advice (Other than referring users to third party advisers registered or chartered as fiduciaries (“Adviser(s)”) with a regulatory body in the United States). The article and opinions in this publication are for general information only and are not intended to provide specific advice or recommendations for any individual. We suggest that you consult your accountant, tax, or legal advisor with regard to your individual situation. 

SmartAsset Advisors, LLC (“SmartAsset”), a wholly owned subsidiary of Financial Insight Technology, is registered with the U.S. Securities and Exchange Commission as an investment adviser. SmartAsset’s services are limited to referring users to third party advisers registered or chartered as fiduciaries (“Adviser(s)”) with a regulatory body in the United States that have elected to participate in our matching platform based on information gathered from users through our online questionnaire. SmartAsset receives compensation from Advisers for our services. SmartAsset does not review the ongoing performance of any Adviser, participate in the management of any user’s account by an Adviser or provide advice regarding specific investments. 

We do not manage client funds or hold custody of assets, we help users connect with relevant financial advisors.

Sources:
1. “The Value of a Financial Advisor: What’s It Really Worth?” SmartAsset (Nov. 2024)

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Special Report

Insiders Are Selling These 3 Stocks—Here’s Why

Reported by Leo Miller. Date Posted: 12/10/2025. 

Key Takeaways

• Dutch Bros insider selling appears routine and non-bearish, driven by predetermined plans and consistent historical patterns.
• Monolithic Power Systems shows a moderately bearish signal, with large, discretionary sales by multiple executives amid a strong stock rally.
• Palantir insider sales look somewhat bearish, especially due to their size, timing, and concentration among top executives, though prior patterns mitigate some concern.

Insider selling often triggers investor anxiety—but context matters. Recent sales at Dutch Bros (NYSE: BROS), Monolithic Power Systems (NASDAQ: MPWR), and Palantir Technologies (NASDAQ: PLTR)show that not all insider activity carries the same implications. Below, we break down the sales linked to each of these stocks and evaluate whether investors should be concerned.

BROS Co-Founder Continues Trend of Cashing Out

In late November, Dutch Bros recorded approximately $190 million worth of insider selling. Around $136 million of that came from co-founder and Executive Chairman Travis Boersma. While a sale of that size by a founding insider can raise red flags, the circumstances suggest otherwise.

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All of Boersma’s sales were executed under a predetermined 10b5-1 plan, which makes it less likely he traded on material non-public information. Moreover, Boersma has been routinely selling Dutch Bros shares throughout 2025: he sold about $145 million in February, $170 million in May, and $165 million in August. His recent sales align with that ongoing pattern.

The same appears true for DM Individual Aggregator, LLC, which sold $53 million worth of shares in November. Overall, these sales look like a coordinated effort by large holders to gain liquidity over time rather than a one-off bearish signal for Dutch Bros.

MPWR: Insider Selling Ramps Up in November

Monolithic Power Systems, a chip stock that has run roughly 67% in 2025, also saw notable insider activity in November. Since the beginning of the month, the company recorded about $59 million worth of insider sales. Approximately $53 million of that, or 90%, came from non-10b5-1 plan sales, meaning most of these sales were discretionary.

This selling involved several senior figures:

• Maurice Sciammas, EVP of Worldwide Sales, sold $34 million
• Saria Tseng, EVP of Corporate Marketing, sold $18 million
• Director Kuo Wei Herbert Chang sold about $175,000

Neither Sciammas nor Tseng had made such large discretionary sales earlier in the year, which makes the timing more notable. Given Monolithic’s dramatic gains in 2025, the recent insider selling appears to be a moderately bearish signal. That view is reinforced by the fact that November’s sales account for around 39% of the company’s total insider selling in 2025.

PLTR Sees Millions in Sales From Three Top Insiders

Palantir, a roughly $432 billion defense-focused software company that is up about 140% in 2025, saw insiders sell shares worth around $163 millionbetween Nov. 20 and Nov. 24. About $153 million, or 94%, of those sales were not made under 10b5-1 plans.

Because most of these sales were discretionary, they are more likely to signal concern than predetermined-plan sales. The sales were concentrated among top leadership:

• CEO Alex Karp sold $66 million
• Co-founder Stephen Cohen sold $57 million
• CTO Shyam Sankar sold $28 million

Karp and Cohen have been making routine discretionary sales throughout 2025; for Sankar, this was the first large discretionary sale since May, which warrants additional scrutiny. While the five-day surge represented nearly 18% of Palantir’s insider selling in 2025, it is not necessarily extreme given the stock’s strong run.

Insider Sales: More Than Meets the Eye

These examples show that insider sales can have very different meanings depending on context. Dutch Bros’ $190 million in sales were the largest by dollar amount, but they also appear to have the least bearish implications because they were largely executed under 10b5-1 plans and fit an established pattern.

Investors should evaluate insider sales not just by dollar amounts, but by timing, structure (10b5-1 vs. discretionary), and the sellers’ history—each factor helps paint a more complete picture.

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