Top 5 Ways to Pay No Tax on Capital Gains & Dividends

Today, I’d like to explore strategies to avoid taxes on capital gains and dividends. Both of these investment returns come in two flavors. Short-term capital gains and ordinary non-qualified dividends are taxed like income, so it’s awfully difficult to avoid taxes on those.


Long-term capital gains (LTCG), realized when you sell an asset you’ve held for more than a year, and qualified dividends (QD) are a different variety. The tax treatment on them can be much more favorable.

It can also be not so favorable. Typically, even though these are a better flavor of payout, you can expect to pay at least 15% on them, and as much as about 37% if you happen to make millions and live in California. How so?

In addition to the standard 15% tax on LTCG and QD, the following apply:

  • 3.8% ACA tax for individuals with AGI of at least $200,000, or couples with an AGI of at least $250,000
  • Additional 5% tax for those in the top (39.%) federal income tax bracket
  • State income tax in most states, which runs as high as 13.3%

Although I’m not in the top federal income tax bracket, I pay the 3.8% and a hefty state income tax any time I realize LTCG or a QD in my taxable account. It’s important to note that you won’t see these taxes in a Roth or tax-deferred account. This Top 5 list applies to a taxable account.

The Top 5 Ways to Pay No Tax On Capital Gains & Dividends


1. Keep taxable income low (and be married).

I’m not trying to say you should let the tax tail wag the dog.


norfolk terrier schnauzer

not much of a sled dog


By all means, earn what you can while you’re accumulating wealth, and avoid turnover in your taxable account (buy and hold). The time to keep taxable income low is in retirement. If a substantial portion of your nest egg is in taxable and Roth dollars, you should be able to keep your taxable income far below your annual budget.

In 2016, a couple can have a taxable income of $75,300 and pay no tax on all LTCG and QD. While this may sound low to you, we learned in The Taxman Leaveth how a couple with a well constructed portfolio can easily spend six figures while keeping taxable income low.

For a single filer, you can only have half the taxable income to be in the 15% federal income / 0% LTCG & QD bracket. Keeping taxable income under $37,650 is a big ask for most retired physicians. Love and marriage pays.


2. Tax Loss Harvest / Tax Gain Harvest.

On January 20th, 2016 I made two quick exchanges in my Vanguard taxable account. I sold shares of VFIAX (S&P 500 Index) to buy shares of VTSAX (Total Stock Market). I also sold shares of VTMGX (Developed International index) to buy shares of VFWAX (International Index).

In two minutes, I had a paper loss of about $39,000, but remained invested in assets that correlate very well to my original position.

That $39,000 capital loss can be used to offset future LTCG, or better yet, $3,000 of earned income every year for 13 years. Behold the power of tax loss harvesting.

Tax gain harvesting is a strategy to utilize in early retirement. If you are in the fortunate position of having taxable income below the threshold above ($75,300 for joint filers), take some capital gains to reset your cost basis and pay no tax. Do this until your taxable income has reached the magic number. Another option is to make Roth conversions to fill the bracket. Look at your situation and do what works for you. Just don’t leave that 15% bracket unfilled if you can help it.

If you go over by a few hundred dollars, don’t worry. Having a taxable income of $76,000 doesn’t mean you pay 15% on all LTCG & QD, just on the $700 overage.


3. Give Appreciated Shares to Charity.

You might not be in love with willfully parting with your hard earned money, but trust me, it’s better than option #4. It’s also true that giving, or joyful generosity, is a key contributor to our happiness. When you donate appreciated assets, capital gains taxes aren’t paid by the giver or receiver. Win, win.

Giving stocks or mutual funds directly to a charity can be cumbersome. I advocate the use of a Donor Advised Fund to facilitate the transaction. I’ve had several, but I prefer Fidelity’s for its low costs and low $50 minimum grant.


4. Die.

That’s right. Buy the farm. Kick the bucket. When assets in a taxable account are passed on to heirs in the next generation, the cost basis is reset to the current value. The assets can then be sold, tax free. The tax savings can be huge.

For example, if I had been a smart baby and purchased $10,000 of an S&P 500 index fund when I was born in 1975, it would be worth over $700,000 today. Selling it today, I would incur nearly $200,000 in taxes. But if I were to start pushing up daisies, leaving the fund to my children, no tax (unless the estate is exceedingly large and we’re looking at estate taxes).


rope climbing river

PoF risks a stepped up cost basis


A couple caveats. The first index fund wasn’t sold until the year after I was born, when John Bogle of Vanguard fame created the First Index Investment Trust. Also, I don’t recommend death as a tax avoidance strategy, but the knowledge could be helpful in estate planning. Don’t give those highly appreciated assets away while alive. Leave them for your heirs to inherit tax free.

Interestingly, when passing along to a surviving spouse, the cost-basis is stepped up to the halfway point between the initial cost and the current valuation. I did not know this until I researched it for this article.

5. Buy equities with low or no dividend.

The aforementioned strategies require something you may not be prepared to do, like retire, give your money away, or keel over. What’s a doc to do while working, saving, and staying alive?

You can do your best to invest in equities that don’t return much to investors beyond growth in the intrinsic value of the stock. Some companies pay no dividends. Warren Buffett’s Berkshire Hathaway is famous for being one of them. Owning BRK stock, you will get all the benefits of the total return, and none of the tax drag that dividend producing assets give you.

Growth stocks are another asset class that tends to offer lower dividends compared to the total market and value stocks. Of course, if growth stocks underperform (see the year 2000), the tax benefit might be outweighed by poor performance.

Are you able to take advantage of any of these? I currently #2,3, and to some extent #5 by sticking with tax efficient index funds in the taxable account. I look forward to the possibility of #1, and hope to stave off #4 as long as possible. Have you got a #6? Find the comment box below and let us know!


  • The Green Swan

    The 15% tax bracket is a great little caveat in the tax code. I sure hope it’s still around when I’m ready to take advantage of it.

    I do try to keep my higher dividend paying funds in my tax deferred accounts rather than my taxable account. Otherwise that tax can add up to some real money.

    But one thing I could look into and do better with is the tax loss harvesting. I’ve never really paid that much attention but definitely should. Your example was good and that’s a pretty big income offset without really changing your portfolio.

    Thanks for the post PoF.
    The Green Swan

    • Hello Green Swan,

      I’m hoping to be able to take advantage of 0% capital gains in the 15% bracket in the early part of the 2020s, assuming again that the law doesn’t change. The biggest enemy to The Plan to keep taxable income low might just be this website. I can live with that.

      A more thorough treatment of Tax Loss Harvesting is in my list of topics to write about. There are many nuances and different ways of doing it that deserve attention. The “wash sale” rule is the source of much confusion.


  • ryk1861

    The only thing worse than paying taxes is not having to pay taxes. 😉

  • Nice J-Hook on the rope there. Is that a recent photo and are you training for an event?

    Still trying to wrap my head around Tax Loss Harvesting. It hasn’t been something I have to worry about, yet.

    • Is that what that maneuver’s called? The picture is from last year. After failing to climb the wet rope to the top in my first Spartan race, I felt compelled to install a rope swing for the kids. It just happens to double as a climbing rope 🙂 Failure is a powerful motivator. And yes, I completed the wet rope climb in my second Spartan race. I’m slated for a Tough Mudder this summer. I’m not specifically training for it, but doing my best to stay in shape like I always try to do.

      TLH is a fairly recent addition to my bag of tricks, but I was able to take advantage of some opportunities in the down markets we had last fall and again this winter.


  • Good reading.
    I am reminded of the old adage
    “In life, one can only be certain of two things – death and taxes”.
    To your point #4, it should be “Death and NO taxes”
    I think I am with you and leaning towards not dying…..😊

  • We are definitely aiming to keep our income low in retirement, both for tax purposes and for ACA subsidies. While we (a married couple) can take out substantially more than we need from our investments in retirement, we can’t do that AND still get a well-subsidized ACA plan, at least according to the current rules which could certainly change. So we’re currently in the process of trying to hone in on our sweet spot: the income level in retirement where we can get the best quality of life along with the lowest taxes and highest subsidy. This all relates to your point about tax loss and gain harvesting — we don’t want to harvest gains now because we’re in a high bracket at the moment, and we don’t want to harvest losses because it’s advantageous over time to have a higher cost basis to minimize our gains and income for ACA purposes. It’s a lot to figure out, but worth considering!

    • The best you can do is plan for the future based on today’s rules, knowing that rules will probably change.

      I completely agree with not harvesting gains now; I avoid capital gains at all costs, and I wish I could do away with the dividends while maintaining the diversification and low costs of the Vanguard index funds. As far as TLH, I think the benefit of deducting $3000 in income now in a high tax bracket would more than offset possibly paying LTCG on $3000 later, unless it pushes you over an ACA subsidy cliff. Last I checked the subsidy for a couple disappeared in the low $60k (MAGI) range, but for a family of 4 (which we’ll be for quite a few years), it’s around $100k, well above the 15% tax bracket. That sweet spot might be a moving target, but you’re closer to retirement than me, so you can do some more concrete planning.


  • Good summary PoF. For high income W2 earners gunning for FIRE, tax loss harvesting is a big deal. It is likely they are saving in a taxable account and getting hit with additional cap gains. Losses can offset these and run 3k in the negative. Then in retirement they can be strategically sold to fill up the lower tax brackets and hopefully get taxed at 0%.

    • That’s the idea, Happy Philosopher. Ideally, capital gains are avoided in the taxable account until retirement. A good reason to steer clear of actively managed funds in a taxable account.

      Using Vanguard index funds exclusively in my taxable account, I’ve taken 0 capital gains in the last few years, but I’ve banked many years worth of losses.


Share your thoughts with the PoF community.