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Etsy Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Etsy provides health insurance through UnitedHealthcare, covering 100% of premiums for employees and dependents. Additional benefits include dental (Delta Dental), vision, mental health support, and wellness programs 1. As ACA premiums rise and subsidies expire, Etsys fully covered plans offer a strong buffer against market volatility, making employer-sponsored coverage significantly more cost-effective Click here to learn more

'Etsy employees with concentrated stock positions may benefit from thoughtful tax planning that allows for tax deferral while balancing liquidity, compliance, and long-term compounding,' Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'Etsy employees who hold highly-appreciated stock may want to consider tax-efficient strategies that help mitigate their liabilities while aligning with their overall retirement goals,' Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

How taxes can affect investment returns, particularly on concentrated stock positions.
Exchange funds and options-based strategies as methods for tax deferral and diversification.
Alternative planning techniques outside ETFs, including charitable trusts and gifting strategies.

By Carlos Hernandez, Wealth Enhancement advisor

When it comes to driving portfolio returns, many investors aim to keep management fees low by investing in low-cost index funds and exchange-traded funds (ETFs). While fees matter, however, the real culprit for lower-than-anticipated performance is taxes. ¹

Wealth Enhancement advisor Carlos Hernandez explains: 'By losing less to taxes each year, investors have access to more capital that can continue to compound over time. This makes tax deferral an important part of an effective financial plan.' Etsy employees looking for long-term growth strategies could benefit by understanding how to better manage their investment tax burdens.

Trade Money

One area where taxes can take a toll is on the sale of company stock or other concentrated investment positions. Etsy professionals looking to diversify could face significant capital gains taxes on an outright sale. One way to diversify without triggering immediate capital gains is through exchange funds. By contributing their highy-appreciated stock to a pooled fund, investors can trade their concentrated holdings for shares in a diverse basket of securities. This method can be used by Etsy employees who want to diversify while postponing taxable events.

Although this method allows for tax deferral, it also requires investors to hold the exchange fund for a period of time, typically seven years. ² This could create a challenge for investors who require liquidity. Additionally, these funds are often exclusively accessible to wealthy, accredited investors—something Etsy executives should carefully evaluate.

Funds Based on Options

Another way to mitigate taxes on the sale of highly-appreciated stock is by using options contracts. The idea is to hedge risk with put options while covering the cost of those puts by selling call options—a strategy called 'collaring'. From there, the strategy reverses, with investors selling put options and using the proceeds to buy call option on an equity or bond index. ³ If managed effectively, this helps to diversify a concentrated portfolio while still maintaining liquidity.

Given the complexity of this strategy, meticulous planning is necessary. It's generally recommended that investors work with an experienced financial advisor before pursuing this approach.

Things to Be Aware of

Although these strategies can be beneficial for Etsy employees who hold highly-appreciated stock, caution is recommended. There are costs associated with these approaches, and potential liquidity risks. Additionally, the IRS may eventually contest such arrangements because their tax status has not been thoroughly examined—something Etsy retirees should keep top of mind.

'Tax drag reduction strategies can be effective, but they must be assessed through the lens of risk, liquidity, cost, and compliance,' warns Carlos Hernandez. What is appealing in theory must hold up to inspection in the real world.

Alternative Strategies

Although they show promise, investors with highly-appreciated stock or those looking to postpone gains have other alternatives besides exchange funds or options. Other tactics could include:

- Prepaid variable forwards (subject to IRS regulations, contracts to sell at predetermined terms in the future).
- Charitable remainder trusts (CRTs), which allow investors to donate appreciated stock to a charitable trust and receive a stream of regular income in return.
- Donor-advised funds (DAFs), which provide investors with a tax deduction for the fair market value of the appreciated stock they donate.
- Other gifting techniques, such as direct donations to charity or family.
Each has its own set of guidelines, advantages, and disadvantages. To limit unnecessary taxes or violating the constructive sale regulations, careful planning is necessary for Etsy professionals managing complex portfolios.

The Bottom Line

Although the movement to mitigate the tax burden on investments is not new, the instruments are changing. Both exchange funds and options-based structures offer investors a way to manage tax liabilities, especially for Etsy employees who hold highly-appreciated stock.

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In the end, taxes are unavoidable. However, with the correct set of instruments, they can be controlled and postponed. 'The real value comes from aligning tax strategy with investment strategy,' summarizes Carlos Hernandez.

Sources:

1. BlackRock Advisor Center. ' Investing for After-Tax Returns ,' 2025.

2. Kiplinger. ' Four Clever and Tax-Efficient Ways to Ditch Concentrated Stock Holdings ,' by Robert Waskiewicz. Sep. 11, 2025.

3. Financial Planning Association. ' Tax-Efficient Ways to Diversify Concentrated Stock Positions ,' by Peter Lazaroff. Oct. 2024.

What type of retirement plan does Etsy offer to its employees?

Etsy offers a 401(k) retirement savings plan to help employees save for their future.

Does Etsy match employee contributions to the 401(k) plan?

Yes, Etsy provides a matching contribution to the 401(k) plan, which helps employees maximize their retirement savings.

What is the eligibility requirement for Etsy employees to participate in the 401(k) plan?

Employees at Etsy are eligible to participate in the 401(k) plan after completing a specified period of service, typically outlined in the employee handbook.

Can Etsy employees choose how to invest their 401(k) contributions?

Yes, Etsy employees can choose from a variety of investment options within the 401(k) plan to align with their retirement goals.

What is the vesting schedule for Etsy's 401(k) matching contributions?

Etsy has a vesting schedule for matching contributions, which means employees must work for a certain period before they fully own those contributions.

How can Etsy employees access their 401(k) account information?

Etsy employees can access their 401(k) account information through the plan's online portal or by contacting the plan administrator.

Are there any fees associated with managing Etsy's 401(k) plan?

Yes, there may be administrative fees associated with Etsy's 401(k) plan, which are typically disclosed in the plan documents.

Can Etsy employees take loans from their 401(k) accounts?

Yes, Etsy allows employees to take loans from their 401(k) accounts under certain conditions, as outlined in the plan guidelines.

What happens to an Etsy employee's 401(k) if they leave the company?

If an Etsy employee leaves the company, they can choose to roll over their 401(k) balance to another retirement account, cash it out, or leave it in the Etsy plan if allowed.

Does Etsy provide financial education resources related to the 401(k) plan?

Yes, Etsy offers financial education resources and workshops to help employees make informed decisions about their 401(k) savings.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

Etsy offers its employees a comprehensive retirement plan, primarily centered around a 401(k) with competitive employer matching contributions. Employees are eligible for the 401(k) plan after meeting specific criteria, such as one year of service and being at least 21 years old. The 401(k) plan at Etsy allows participants to make tax-deferred contributions, up to a maximum set by the IRS. For the year 2024, this limit is $23,000, with an additional catch-up contribution of $7,500 for employees aged 50 and over (Investopedia) (CapitalGroup NACG). The plan also includes various investment options, including mutual funds and stocks, which employees can choose from depending on their risk tolerance and retirement goals. Etsy's 401(k) plan emphasizes the importance of consistent employee participation and is structured to align with federal guidelines like ERISA, which protects retirement assets. Although Etsy does not offer a traditional pension plan, its 401(k) plan is designed to be flexible and supportive of long-term retirement savings, with employer contributions enhancing the growth potential of the plan

Restructuring Layoffs: Etsy announced in December 2023 that it would be laying off 11% of its workforce, amounting to approximately 225 employees. This move comes as the company faces a challenging macroeconomic environment and increased competition. The layoffs are expected to cost Etsy between $25 million and $30 million, primarily due to severance payments, employee benefits, and related expenses. The restructuring is aimed at achieving greater operational efficiencies and cost savings, especially in the wake of flat gross merchandise sales since 2021. Additionally, Etsy has made significant changes to its executive team, including the departure of its Chief Marketing Officer and Chief Human Resources Officer, with their responsibilities being redistributed among existing executives.

2022: Etsy employees were eligible for stock options and RSUs as part of their compensation package. Specific details about the vesting schedules and performance criteria are detailed in the company's annual report (Source: Etsy Annual Report 2022, Page 45). 2023: Etsy continued offering stock options and RSUs to its employees. The grants were generally provided based on seniority and role within the company (Source: Etsy Proxy Statement 2023, Page 38). 2024: In 2024, Etsy maintained its stock option and RSU programs. Employees in management and critical roles were prioritized for these benefits

1. Official Etsy Website Etsy Careers Page: Often provides information about employee benefits, including health benefits. Etsy Employee Handbook: If available, it may have specific details on healthcare benefits. 2. Reliable Sources and News Outlets Glassdoor: Employees often share details about their benefits here. Indeed: Offers company reviews and sometimes specific details on benefits. LinkedIn: Check for company updates or employee discussions on benefits. Forbes: May provide news or articles about employee benefits. Business Insider: Could offer insights into employee benefits and company news.