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Whitepaper

Custom indexing for tax-optimized growth.

Improve post-tax returns through custom indexing and tax-loss harvesting.

01

TL;DR.

Custom Index investing provides the benefits of broad-market exposure alongside greater customization, diversification, and after-tax returns. Custom Indexing strategies can be quite profitable, often out-performing the exchange-traded funds (ETFs) they track by as much as 0.34% to 3.62% annually. In a Custom Index portfolio, investors hold the individual positions that comprise the ETF rather than the ETF itself, allowing them to isolate specific positions to sell at a loss through a process called “tax-loss harvesting.” Holding individual positions also provides investors with a much greater degree of precision, enabling them to build a portfolio around specific criteria. Previously reserved for institutional and high-net-worth investors, custom indexing has recently become far more accessible thanks to new financial technology infrastructure, the ability to trade fractional shares, and zero-commission trading.

0.34% to 3.62% improvement over tracked ETFs.

Source: O’Shaughnessy Asset Management - Measuring the Merits of Tax Management (October 2019)

Tax-loss harvesting example

In 2017, an S&P 500 ETF would have resulted in no tax-loss harvesting opportunities, as the S&P 500 was up consistently throughout the year and ended up 22%. However, since 27% of the stocks within that index ended the year with a negative return, custom indexing would have enabled an investor to harvest losses on a significant portion of the portfolio while still maintaining the return/risk profile of the index.

02

Why would I use custom indexing?

2.1

To optimize post-tax returns of public investments through tax-loss harvesting.

2.2

To offset the taxes from an upcoming capital gain event (e.g. liquidity event or crypto sale). Since realized losses from tax-loss harvesting can be used to offset gains either in the current year or indefinitely in the future, it can be advantageous to begin custom indexing ahead of a capital gain event to begin accumulating losses that will offset future gains.

2.3

To improve an investor’s overall diversification by excluding a particular type of company from their portfolio, such as one in which they already have a concentrated position.

2.4

To customize a portfolio according to their values by over-weighting stocks with favored characteristics (e.g. climate awareness, diversity, or geography) or under-weighting others (e.g. oil companies or carbon producers).

2.5

To maximize tax savings while supporting charities, since custom indexing allows investors to donate their shares that have the largest gains.

03

How does custom indexing work?

Tax alpha

Achieving “tax alpha” is the most tangible benefit of adopting a Custom Indexing strategy. Alpha refers to returns in excess of a benchmark—in this case, holding the ETF. Compound believes that tax alpha is the optimal way to measure tax efficiency as it measures the value of active tax management.

Tax alpha occurs when a managed portfolio’s returns versus a benchmark are better after tax than they are before tax.

This tax alpha is typically achieved through tax-loss harvesting, the practice of realizing losses when investments have declined in value, replacing them with similar investments to ensure exposure consistency, and then offsetting realized investment gains with those losses. The magnitude of losses available for harvesting depends on account size and asset volatility. Additionally, the ability to optimize through tax-loss harvesting depends on the investment vehicle selected. ETF losses, for instance, can only be harvested when the entire index has declined in value, while a Custom Indexing strategy can harvest losses when there is a decline in the individual stocks.

Excess after-tax return is the difference between the after-tax return of the portfolio and the after-tax return of the benchmark. Excess pre-tax return is the difference between the pre-tax return of the portfolio and the pre-tax return of the benchmark.

The value of tax-loss harvesting

Tax-loss harvesting is most beneficial when there are large losses in the market and high dispersion of returns between individual stocks. Conversely, benefits will be lower in a year with strong gains and low dispersion of returns between stocks (as in 2017). In other words, tax losses are easily harvested in years with high return/high dispersion and less valuable in years with low return/low dispersion.

In order to determine the scope for harvesting, we looked at four different years that represented clearly distinct scenarios represented by these two variables, using dispersion and returns data for the S&P 500.

We quantified the tax-loss harvesting opportunities with respect to the S&P 500 in these four years. The amount available for tax-loss harvesting can be found under the “Unrealized Loss %” column, and ranges from 39.4% in the volatile year of 2008 to 2.5% in the more standard year of 2009.

Dispersion refers to the range of potential outcomes of investments based on volatility.

The impact of return and dispersion

Year Return Dispersion S&P 500 stocks down Avg return of down stocks Unrealized annual loss Realized loss on $1M portfolio Tax savings at 48% bracket Improvement to after-tax return
2008 Low High 95% -43.9% -39.4% -$394,000.00 $189,120.00 18.91%
2009 High High 15% -15% -2.5% -$25,000.00 $12,000.00 1.20%
2015 Low Low 58% -21.9% -9% -$90,000.00 $43,200.00 4.32%
2017 High Low 27% -15.7% -2.7% -$27,000.00 $12,960.00 1.30%

Assummes no rebalancing within the year. Stocks delisted or removed from index mid-year are excluded from analysis. All returns shown are price-only. “Realized loss” and “Tax savings” will vary based on the individual’s federal and state income tax brackets. “Tax savings” on realized losses are calculated as short-term capital losses due to the annual rebalancing executed.

Even in the most bullish of years (2009), 15% of stocks had a negative return. This is a year in which holding an ETF or mutual fund would have yielded no opportunity to harvest any losses. While the Unrealized Loss % was relatively low, there were still opportunities to harvest losses in 2009. Conversely, 2008 saw incredible potential for tax-loss harvesting any gains, as 95% of the stocks in the portfolio were down for the year, with an average loss in those stocks of 44%. An individual holding a $1,000,000 portfolio in 2008 would have had an opportunity to realize up to $394,000 in losses, leading to $189,120 in tax savings (assuming the individual was in the 37% federal and 11% state tax brackets).

2020 was a strong year for tax-managed strategies. 2020 had volatility and market drawdowns, both of which created increased opportunities for tax-loss harvesting. The US Large Cap market was up +5.4% early in the year, collapsed in March to a low of -31.1%, and then rallied to end the year up +20.8%.

The graph below shows a comparison between an account that tracked the Russell 1000 and a hypothetical account that used a Custom Indexing approach in 2020.  Over the course of the year, the Custom Indexing approach made 24 opportunistic trades, adding up to $241,237 in realized losses. While the opportunities tended to be highly concentrated in the first half of the year (due to the way the market trended), this strategy was able to take advantage of these opportunities and generate tax alpha. An illustration of a tax alpha benefit is further shown below in the tax-loss carryforward example.

Case study: 2020

2020 custom indexing simulation

2020 custom index simulation graph. Depicts custom indexing portfolio just underneath Russell 1000 benchmark and losses accumulating over time.
Russell 1000 benchmark
Custom Indexing Portfolio
Cumulative Losses Harvested

This example is only provided to show the potential post-tax results from tax-loss harvesting and is not to show hypothetical investment results from an OSAM Large Cap portfolio. Individual results will vary for both tax-loss harvesting and index investing.

Illustration: tax-loss carryforward

Year Carried losses Capital gains Harvested losses Capital gains offset with losses Total capital gains post-offset Additional losses declared Total annual capital gains Excess losses accumulated
2020 $0 $202,500 -$241,237 -$202,500 $0 -$3,000 -$3,000 -$35,737
2021 -$35,737 $69,500 -$71,165 -$69,500 $0 -$3,000 -$3,000 -$34,402
2022 -$34,402 $100,000 -$15,000 -$49,402 $50,598 $0 $50,598 $0

Assume, for example, that a taxpayer recognized the $241,237 in harvested capital losses detailed in the 2020 chart above. Assume that the taxpayer also had a liquidity event where they recognized $175,000 in capital gains income. Lastly, the taxpayer recognized an additional $27,500 in capital gains income from the various sales of individual investments. The taxpayer can use the $241,237 to fully offset the capital gains recognized from the company liquidity event and regular trading ($202,500). The individual can also recognize up to $3,000 in total capital loss (on the Schedule D of their tax return).

The remaining $35,737 in losses will be carried forward indefinitely to offset capital gains and ordinary income in future years. In 2021, the taxpayer is able to use the carry-forward losses in addition to the harvested losses from their Custom Indexing strategy to fully offset capital gains again. And, the investor would still carry forward $34,402 to offset 2022 capital gains and ordinary income. In 2022 (YTD), the taxpayer is able to use the 2021 carry-forward losses plus the losses harvested from the Custom Indexing strategy to offset $49,402 of the $100,000 gain recognized. One benefit of “storing” harvested losses comes from their ability to be deployed over time.

Portfolio personalization

Compound’s Custom Indexing portfolio provides clients with an opportunity to have precise control over what their portfolio looks like. From environmental, social, and governance screens to company exclusions, custom indexing allows Compound’s clients to design a portfolio that’s aligned with their value system without sacrificing their financial goals. Some features require working with Compound's advisors due to their complexity.

Environmental, Social, and Governance (ESG) investing is a method of investing that focuses on the sustainability and impact of companies across different industries. Custom indexing allows investors to exclude positions from their portfolios based on evaluations of their ESG practices.

Environmental evaluation determines the impact companies have on our environment—examples of environmental screens include a company’s carbon footprint and its sustainability efforts throughout supply and distribution channels.

Social evaluation determines the internal and external efforts of the company to promote social initiatives—examples of social initiatives include diversity and inclusion hiring practices to advocate for underrepresented communities. 

Governance evaluation measures how the company’s board and management drive positive change—examples of governance include the composition of the company’s board of directors and business ethics.

Over the long term, systematic investing in equities with specific characteristics—like above-average “value,” “growth,” or “momentum”—can improve portfolio performance.

“Factor tilts” are a tool used by investors to preference their portfolios toward a specific thesis. Factors can create alpha opportunities during periods where specific market conditions persist and are a way to add a systematic factor component to your passive Custom Indexing strategy. Most academic and empirical studies show that certain factor exposures over a very long cycle (multiple years) may add a premium above the traditional market. While factor exposures can lead to outperformance, implementing them will increase what’s known as “tracking error.” Tracking error measures how much your portfolio deviates from the indices being replicated. Factor returns can also be cyclical, so you could experience volatile and prolonged periods of underperformance compared with the broader stock market.

Factor investing is an approach that involves targeting specific drivers of return across asset classes. Factors can be broken down further into macroeconomic characteristics, which capture broad risks across asset classes, and style characteristics, which help explain returns and risk within asset classes. Custom Indexing portfolios allow you to tilt towards a specific factor (up to 30%). Factor choices include value, momentum, earnings quality, earnings growth, and income generation. Compound recommends only adopting a factor tilt if you have a long-term view and a willingness to accept a higher degree of tracking error.

Country exclusion allows you to restrict investments in a particular country (e.g. Norway or Zimbabwe). Exclusion can be due to social, geopolitical, economic, or environmental reasons. This type of exclusion furthers the control you have over what your investment strategy looks like and the composition of your underlying positions. Country exclusion at the company level ensures the strategy fully achieves the objective vs. utilizing ETFs or mutual funds which still may contain minimal exposure.

Sector exclusion can be useful if an investor is overexposed to a particular sector elsewhere on their balance sheet (e.g. Saas Software or Electric Vehicles). Overexposure may be due to concentrated company equity position or existing public/private investments. Sector exclusion can help reduce total balance sheet exposure while maintaining a comparable portfolio structure. Compound advisors work with clients to determine if sector exclusion is advantageous to a client’s overall investment strategy.   

Company stock ownership can be one of the greatest drivers of wealth creation. However, once liquid, a concentrated position presents excess risk relative to the broader market. This risk can be an impediment to wealth preservation over the long run. Compound can help clients build a portfolio around their concentrated position, de-risking over time by leveraging harvested losses to offset gains realized through the sale of company equity. Additionally, concentrated positions create over-exposure to the industry the company operates within—this overexposure creates inefficiencies for the strategy’s overall diversification plan. A “nearest neighbors” list is designed to counteract the overlapping risk. Nearest neighbors are companies with similar exposure to the concentrated position (e.g. companies that operate similarly to Coinbase)—these companies are restricted or underweighted to create a representative index established around the concentrated position, delivering an investment experience closer to the market while mitigating concentrated risk.

Investors can also exclude specific companies from their portfolio (e.g. Coinbase). Exclusion could be due to negative opinions about individual companies or a need to reduce exposure to companies similar to those already owned. Company exclusion provides a solution to mitigate overlapping exposure without executing a full “nearest neighbors” screen. This exclusion is done at the company level, therefore, allowing you to achieve the highest degree of precision when building your investment portfolio. 

04

What is Compound’s specific offering?

Compound's Custom Indexing offering allows investors to construct portfolios that are fine-tuned to their risk appetite, built to complement existing investments, and professionally managed.

To offer custom indexing to its clients, Compound partners with O’Shaughnessy Asset Management (OSAM), a quantitative asset management firm based in Stamford, CT and owned by Franklin Templeton. The firm delivers a broad range of equity portfolios to institutional investors, individual investors, and high-net-worth clients of financial advisors. The firm has managed client assets since 1996 and is currently overseeing and managing $6 billion to bring this sophisticated investment product to life.

Compound facilitates account setup, funding, and portfolio design based on a client’s risk tolerance and financial objectives. OSAM is responsible for ongoing investment management—this includes executing trades, rebalancing, and tax-loss harvesting.

Compound conducted careful due diligence of Custom Index advisors before selecting OSAM as its primary Custom Indexing sub-advisor. OSAM stands out to us among its peers for its investment philosophy, caliber of talent, long history in asset management SMAs, and reasonable cost structure. Compound continually monitors all sub-advisors, including OSAM, to ensure continued quality of service and best-in-class performance versus peers.

Transitioning assets from a taxable account into a new portfolio can often lead to tax implications for the client. OSAM supports tax transition analysis based on current holdings to see the expected tax cost/benefit, subsequent deviation from the model, and scenarios for various transition processes. This service is currently reserved for individuals working with Compound’s advisors. As part of this engagement, Compound's advisors will connect with their clients to determine an optimal roadmap and path forward.

05

Compound investment philosophy.

Compound’s investment philosophy operates on three fundamental pillars:

  1. Globally diversified passive investing for long-term, risk-adjusted returns.
  2. Strategic high-growth investments (such as company equity and private investments).
  3. Tax-conscious investing. 

For investors with access to high quality private market opportunities—such as equity compensation at private companies or private fund investments—public market investments may not be needed as a source of alpha in an investment portfolio. When investors do seek to generate alpha through active investing, they tend to underperform passive strategies over the long term. Between 2011 to 2021, only 17.5% of active managers outperformed the S&P 500 index. And when it comes to individual investors, certain behavioral anomalies—such as trend following, poor diversification, and overconfidence—result in worse performance than if investors had simply bought-and-held ETFs with a systematic rebalancing plan.

We believe that the role of a public market portfolio is long-term, sustainable growth, a goal that can be achieved through global diversification and holistic portfolio design.

Diversification, when appropriately executed, serves as a mechanism to reduce portfolio volatility without sacrificing returns. Public market portfolios are effective ways to improve overall diversification—they are relatively easy to design and change, especially when compared to other holdings. 

Diversification isn't a one-and-done effort; portfolios require ongoing monitoring and rebalancing to ensure that asset allocation continues to match the investor’s strategy.

Portfolios made up of securities from varied geographies give investors access to less correlated assets, possible new growth opportunities, and assets insulated from or hedged against US inflation.  

No investment portfolio exists in a vacuum. In order to achieve diversification, a portfolio must be designed with an investor’s entire balance sheet and profile in mind. Important factors to consider are existing exposures (e.g. to specific companies or industries such as technology) and access to investment opportunities (e.g. startup investments, fund investments, or other private investments).

In conjunction with designing and executing strategies for public investments, Compound clients benefit from a nuanced, easy-to-execute strategy for their company and other private investments. Compound helps our clients with more than just their public assets: we optimize their entire balance sheet. 

Disclosure

Atomi Financial Group, Inc. dba Compound Planning (“Compound Planning”) is an investment adviser registered with the Securities and Exchange Commission and based out of New York. Certain information on this website may relate to Compound Tax, LLC (“Compound Tax”), a wholly-owned subsidiary of Compound Planning that provides tax consulting and compliance services.The statement, claim, content, and/or commentary made herein and as found in Compound Planning’s other websites, videos, podcasts, blog posts, articles and other publications or materials, as applicable (collectively, the “Materials”), provides general market commentary or general information and/or expresses the personal opinion of the author or speaker which does not necessarily reflect the views or opinions of Compound Planning.The content found in the Materials, therefore, should not be interpreted as providing legal, tax, or investment advice or any professional advice for that matter nor is it a solicitation to engage in any particular securities transaction. Compound Planning and its representatives may only transact business or provide investment advice in those states and international jurisdictions where it is registered, filed the required notices, and/or is otherwise excluded or exempted from such registration and/or notice filing requirements.For more information on Compound Planning’s investment advisory services, please refer to Compound Planning’s Brochure Form ADV 2A and Form CRS.