Supercharge your Investments with Tax-Loss Harvesting

Supercharge your
Investments with
Tax Loss Harvesting
wealthfront.com

©2013 Wealthfront, Inc.
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Achieving Your
Investing Goals
YOUR ULTIMATE PORTFOLIO IS ONE THAT:
Meets your
unique tolerance
for risk
Maximizes
your net-of-fees,
after-tax return
ULTIMATE
PORTFOLIO

Tax-Loss
Harvesting
ENGINEER YOUR PORTFOLIO WITH ETFs »
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 We’ve already shown how to build a low-cost
investment plan and personalize it for your risk
tolerance in our SlideShare presentation:
 Now, let’s talk about how to use tax-loss harvesting
to improve your after-tax return.

The Basics of Tax-Loss
Harvesting

What is Tax-Loss
Harvesting?
We encourage you to consult a tax professional to see if tax-loss harvesting is right for you.
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 Tax-loss harvesting is a way to make your
investments work harder on your behalf –
by generating tax savings in addition to
investment returns.
 It works by identifying investment losses in
your taxable investment portfolio and
selling those securities to recognize
the loss.
 These capital losses can be used to offset
other gains and reduce or postpone income
taxes.
 Even if you cannot realize the full benefit
this year, you can move your tax losses to
future years, via a "tax-loss carryforward.”

A Simple Tax-Loss
Harvesting Example
Let’s assume you buy
100 shares of an ETF at $65 per
share in a taxable investment
account. We’ll refer to it as your
primary ETF.
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2008 2009
$65
Example data from one ETF during this period. Not representative of your results.

A Simple Tax-Loss
Harvesting Example
If the price drops to $41
(below its cost of $65),
you can harvest the loss
of $24 per share.
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$24
$41
Primary ETF
2008 2009
$65

A Simple Tax-Loss
Harvesting Example
The total potential tax benefit is the loss of $24/share multiplied by the number of
shares you own and then multiplied by your tax rate. With a Federal + State
income tax rate of 51%...
* The tax benefit assumes that you can take advantage of the full credit.
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$65 – $41 = $24 x 100 = $2,400 x 51%
Cost Basis Current Price Loss / Share # of Shares Total Loss Tax Rate
Tax Benefit: $1,224*
This benefit is typically referred as as Tax Alpha and expressed as an additional % return of
your investment portfolio (since it effectively adds to your investment return). In this case,
you generated a Tax Alpha of nearly 19% on the original $6,500 investment.

A Simple Tax-Loss
Harvesting Example
2008 2009
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After harvesting, you can maintain
the risk & return of your portfolio
by replacing your harvested
primary ETF with a similar, but
not identical, secondary ETF,
such as an ETF that tracks a
different index for the same asset
class.
Thirty days later you can sell the
secondary ETF and return to the
primary ETF.
These steps are required to claim
a tax benefit while avoiding the
IRS wash-sale rule (see
appendix).
Primary ETF Secondary ETF

Wealthfront’s Tax-Loss
Harvesting Strategies
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 Wealthfront has two different strategies available
for Tax-Loss Harvesting on client portfolios
1. Daily Tax-Loss Harvesting
2. Tax-Optimized Direct Indexing
 Both of Wealthfront’s Tax-Loss Harvesting strategies
run every day, selling underperforming assets and
replacing them with similar but not identical ones as
opportunities arise.

Daily Tax-Loss Harvesting
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 Wealthfront’s Daily Tax-Loss
Harvesting service applies Tax-
Loss Harvesting to the ETFs that
make up your Wealthfront
portfolio.
 We look across all ETFs and
investment lots in your portfolio
every single day to spot
harvesting opportunities.
 With a diversified portfolio like the
one at Wealthfront, there are
bound to be some
underperforming assets that can
be harvested.
6.8%
-4.5% -2.9%
3.4%
1.8%
-4.5%
Gains Losses
US Stock
Emerging
Markets
Foreign
Developed
Real Estate
Natural
Resources
Bonds

What does it take to do
Daily Tax-Loss Harvesting?
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 You need to understand the IRS wash sale rule and its
implications.
– Running afoul of this rule can easily negate any benefits from tax-loss
harvesting
– Wealthfront had to build a system to specifically track what we could and could
not trade according to the rule
 You need to monitor your portfolio daily
– To avoid missing harvesting opportunities
 You need to integrate tax-loss harvesting into your overall
investment strategy
– Alongside deposits, withdrawals, rebalancing, and dividend reinvestment
– All of those transactions need to comply with the wash sale rule and otherwise
take the right opportunities to harvest
 You need to track the purchase price of every share
– This detailed accounting is critical to identifying which shares can be harvested
and which can not.

Why do we Tax-Loss Harvest Daily?
BECAUSE SOMETIMES HARVESTING OPPORTUNITIES DISAPPEAR AS THE
MARKET REBOUNDS
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Example data from one ETF during an investment period. Not representative of your
results.
Great time to
harvest this
asset
The asset
rebounded
and the
harvesting
opportunity is
now gone
In our simulations, we’ve found that daily harvesting provides up to 50% more
value than the more common once-a-year harvesting (typically done at the end
of the year). To dive into the details of our analysis, see our technical white paper.

Why do we Tax-Loss Harvest Daily?
BECAUSE FLEETING OPPORTUNITIES TO HARVEST ARISE EVEN IN RISING
MARKETS … LIKE 2013 …
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What is the benefit of Daily Tax-Loss
Harvesting?
IT DEPENDS ON YOUR PORTFOLIO’S RISK LEVEL BUT IN GENERAL IT
SHOULD BE ABOUT ~1% OF ADDED RETURN DUE TO TAX SAVINGS
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How can you take Tax-Loss
Harvesting to the next level?
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 What if in addition to harvesting broad
asset classes / indexes / ETFs you could
harvest the individual stocks that make
up each ETF / index ?
 If the S&P 500 is up for the year, there
probably aren’t a lot of tax-loss
harvesting opportunities via an S&P 500
ETF investment.
 But even if the S&P 500 is up overall,
there are probably some individual S&P
500 stocks that are still down. What if
you could harvest those?
 We call that Stock Level Tax-Loss
Harvesting
GOOG
AAPL

Stock Level Tax-Loss
Harvesting
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 Stock Level Tax-Loss Harvesting is not possible
with ETF or index fund investments because
legally ETFs / index funds can not pass on losses
for individual stocks on to their investors
 So ETF / index fund investors miss out on
opportunities for additional tax savings
 However, it’s possible to benefit from harvesting
losses from the individual stocks that comprise an
index if you own the index’s underlying stocks
directly
 Wealthfront’s Tax-Optimized Direct Indexing does
this for you by directly owning the individual
stocks tracked by major US indices like the S&P
500 and the S&P 1500
GOOG
AAPL

Does Stock-Level Tax-Loss
Harvesting Work?
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Direct Indexing outperformed VTI in a substantial majority of years, especially in bad markets. As expected, adding more
individual stocks to the Direct Indexing position (i.e. moving from the Wealthfront 500 to the Wealthfront 1000) improved
performance. This is in large part due to the extra tax-loss harvesting opportunities available with the larger set of individual
securities.
See disclosure for model assumptions.

What’s the bottom line?
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 Adding Daily Tax-Loss Harvesting and Tax-
Optimized Direct Indexing to your
investments can increase after-tax
investment returns by 2.03% per year!
 In 15 years, a portfolio that started with
a$500,000 deposit can have +$662,000 in
additional value over a portfolio with no tax-loss
harvesting applied to it.
See disclosure for model assumptions.
$500k
+$662k
From Harvested Losses
15 years

How can I get this?
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 Wealthfront clients with a minimum investment of $100,000 get
access to Daily Tax-Loss Harvesting:
 Wealthfront clients with a minimum investment of $500,000 get
access to the Tax-Optimized Direct Indexing:
 You can also get a basic diversified Wealthfront portfolio starting at
$5,000:
GET A DIVERSIFIED PORTFOLIO WITH
DAILY TAX-LOSS HARVESTING »
GET A DIVERSIFIED PORTFOLIO WITH THE
TAX-OPTIMIZED DIRECT INDEXING»
INVEST NOW »

Disclosure
This presentation was prepared to support the marketing of Wealthfront's investment products, as well as to explain its tax-loss harvesting strategy. Nothing in this presentation
should be construed as a solicitation or offer, or recommendation, to buy or sell any security. Financial advisory services are only provided to investors who become Wealthfront
clients. This presentation is not intended as tax advice, and Wealthfront does not represent in any manner that the tax consequences described herein will be obtained or that
Wealthfront's tax-loss harvesting strategy, or any of its products and/or services, will result in any particular tax consequence. The tax consequences of the tax-loss harvesting
strategy and other strategies that Wealthfront may pursue are complex and uncertain and may be challenged by the IRS. This presentation was not prepared to be used, and
cannot be used, by any investor to avoid penalties or interest that can be imposed on the investor.
Prospective investors should confer with their personal tax advisors regarding the tax consequences of investing with Wealthfront and engaging in this tax strategy, based on
their particular circumstances. Investors and their personal tax advisors are responsible for how the transactions conducted in an account are reported to the IRS or any other
taxing authority. Wealthfront assumes no responsibility for the tax consequences to any investor of any transaction.
When Wealthfront replaces investments with “similar” investments as part of the tax-loss harvesting strategy, it is a reference to investments that are expected, but are not
guaranteed, to perform similarly and that might lower an investor’s tax bill while maintaining a similar expected risk and return on the investor’s portfolio. Expected returns and
risk characteristics are no guarantee of actual performance.
The chart showing potential tax savings (“Bottom Line of Tax Loss Harvesting”) from the tax-loss harvesting strategy and the charts showing the performance comparison
between the up-to-500 individual stock position in the Tax-Optimized Direct Indexing(“Wealthfront 500”) vs. the SPY ETF are historical simulated returns (Does Stock Level Tax-
Loss harvesting Work?) based on backtesting and do not rely on actual trading using client assets. The results are hypothetical only. Several processes, assumptions and data
sources were used to create one possible approximations of how Wealthfront’s tax-loss harvesting strategy might have benefited investors in the past, and a different
methodology may have resulted in different outcomes. These results were achieved by means of the retroactive application of a model designed with the benefit of hindsight.
The results of the historical simulations are intended to be used to help explain possible benefits of the tax-loss harvesting strategy and should not be relied upon for predicting
future performance.
We simulated the potential after-tax benefits of our tax-loss harvesting services and found that asset-class tax-loss harvesting it added an average of at least 1.29% annually and
stock-level tax-loss harvesting combined with asset-class tax-loss harvesting added an average of at least 2.03%. We used several assumptions to create these possible
approximations, but did not rely on actual client trading history. These results are based on a study Wealthfront conducted for the years between January 2000 and August 2014,
assuming a Wealthfront account with a risk score of 7 an initial deposit of $100,000, additional quarterly deposits of $10,000, and periodic rebalancing for asset-class tax-loss
harvesting and an initial deposit of $500,000, additional quarterly deposits of $50,000, and periodic rebalancing for stock-level tax-loss harvesting combined with asset-class tax-loss
harvesting. Dividends and interest were not considered.
To compare the possible benefit of continuous vs. annual year-end tax-loss harvesting, we use the same assumptions for the historical simulation for the years between January
2000 and August 2014 but with tax-loss harvesting opportunities examined daily vs. annually at year-end.
The chart showing the tax alpha and cumulative return for daily tax-loss harvesting (Why do we Tax-Loss Harvest Daily) clients is based on Wealthfront’s estimates from existing
client data since we launched our asset-class tax-loss harvesting in October 2012 through August 2014. The chart was based on the subset of our clients with tax-loss harvesting
enabled in their accounts and the returns and tax alpha were estimated for their accounts only. The return estimates were based on time-weighted returns. The cumulative
returns were calculated by taking the composite’s daily return based on its daily balance series, where the composite’s balance is the aggregated value of all the accounts under
our TLH strategy. We then compound the daily return series to get the compounded return over the period. The monthly tax alpha was calculated using the net tax
benefit/liability and dividing by the aggregate balance. The net tax benefit over the period includes the liquidation of positions transferred in and sold to invest the client
account in the Wealthfront portfolio.

Disclosure
To achieve the projected returns (What’s the bottom line), we assume the Wealthfront portfolio with basic service has a risk score of 7, which results in a projected annual 5.2%
return. This projected return does not take into consideration the effect of taxes, changing risk profiles, or future investment decisions. Projected returns do not represent actual
accounts and may not reflect the effect of material economic and market factors. The results shown do not represent the results of actual trading using client assets, but were
achieved by means of forward-looking analysis. This projected return is not a guarantee of actual performance.
We simulated the potential annual after-tax benefits of our tax-loss harvesting services and found that asset-class tax-loss harvesting as per our Daily Tax-Loss Harvesting service
combined with the stock-level tax-loss harvesting per our Tax-Optimized Direct Indexing added an annual benefit of at least 2.03%.
We assume the 2.03% annual “tax alpha” from our simulation is reinvested back into the basic Wealthfront service portfolio to obtain a projected return of 6.11% (vs. the 5.99%
projected return for the basic service). We compounded for twenty years the basic Wealthfront service portfolio and the Wealthfront portfolio with Daily Tax-Loss Harvesting
combined with the Tax-Optimized Direct Indexing both starting with $500,000. The estimated difference between the two portfolios at the end of the twenty years was
approximately $662,166.70.
With regard to the historical simulated results presented, different methodologies may have resulted in different outcomes. For example, we assume that an investor’s risk
profile and target allocation would not have changed during the time period shown; however, actual investors may have experienced changes to their allocation plan in response
to changing suitability profiles and investment objectives. Furthermore, material economic and market factors that might have occurred during the time period could have had
an impact on decision-making. Actual investors on Wealthfront may experience different results from the results shown. There is a potential for loss as well as gain that is not
reflected in the hypothetical information portrayed. Investors evaluating this information should carefully consider the processes, data, and assumptions used by Wealthfront in
creating its historical simulation.
While the data used for its simulations are from sources that Wealthfront believes are reliable, the results represent Wealthfront's opinion only. The return information uses or
includes information compiled from third-party sources, including independent market quotations and index information. Wealthfront believes the third-party information
comes from reliable sources, but Wealthfront does not guarantee the accuracy of the information and may receive incorrect information from third-party providers. Unless
otherwise indicated, the information has been prepared by Wealthfront and has not been reviewed, compiled or audited by any independent third-party or public accountant.
Wealthfront does not control the composition of the market indices or fund information used for its calculations, and a change in this information could affect the results shown.

The Wash Sale Rule
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 Usually, you can recognize a loss when you sell a security for less than its cost
basis. However, if you buy the same or substantially identical security within 30
days of the sale, the wash sale rule applies and you cannot claim the tax
benefit.
 Consider the wash sale rule when trading for asset reallocation, rebalancing,
dividend reinvesting, withdrawal, or deposit.
 Remember that the wash sale rule applies across all accounts for which you
are the beneficial owner – such as retirement accounts – as well as spousal
accounts for joint tax-filers.
For more information about the wash sale rule, look at the IRS’s webpage:
http://www.irs.gov/publications/p550/ch04.html#en_US_2011_publink100010601

What Do I Do With My
Lowered Cost Basis?
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 While tax-loss harvesting
systematically lowers the cost bases
of your investments, you may be
concerned that tax benefits now will
merely postpone or magnify future tax
obligations.
 It’s true that tax rates and laws are
unpredictable. The time value of
money, however, means that tax
liabilities due in future years are less
costly than the same liabilities
due now.
 You can use the tax savings to help
your portfolio grow. Even with
potential tax rate increases in the
future, the deferral of tax liabilities will
most likely yield net benefits.
 Instead of selling investments
directly, you could make charitable
donations with low-cost-basis assets,
or pass them to your heirs at a
stepped-up basis.
 We encourage you to consult a tax
professional to see if tax-loss
harvesting is right for you.

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