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The Best Way to Donate A Hundred Grand

Blue Door Kew Gardens

No, not the candy bar.

In a related post, I shared how I woke up $100,000 poorer on my 41st birthday. This act of portfolio sabotage was self-inflicted; I greeted the news with a smile. The hundred grand is no longer mine, but I now have the opportunity now to use it to do some good in this world that my family and I live in.

I’ve discussed why I choose to donate. Today’s post will describe how I use a donor advised fund to get the most for my donated dollars.


donor advised fund confirmation
confirmation from vanguard charitable


The easiest way to donate to charity is to simply write a check for cash to your favorite charity. As long as you are giving to a bona fide 501(c)(3) charity (there are over a million in this nation), and you receive a receipt, you can include the donation in your itemized deductions to reduce your income tax. This assumes your itemized deductions exceed the standard deduction.



The Easiest Way is Not the Best Way


How can you donate more to charity at a lower cost to you? By donating appreciated assets. That is, stocks or bonds or mutual funds containing them that are now worth more than you paid.

While you may be able to arrange for a donation of your assets directly to a charitable organization, not every organization would know how to handle the transfer. Small, local charities, the kind I like to give to, could be particularly thorny. This is where the Donor Advised Fund (DAF) comes in.

The DAF accepts your donation and keeps your donated dollars in an account that you control. You get a tax deduction in the year you donate, and you can request grants to charities of your choosing at any time in the future.

Some of the larger brokerage companies, including Vanguard, Fidelity, T. Rowe Price, and Schwab have corresponding DAFs, which can easily accept your donated funds, and have easy-to-navigate online interfaces allowing you to dish out the money when you decide it’s time to give.

I actually have a DAF with both Vanguard and Fidelity, and used to have one with T. Rowe Price, but I moved the funds when I made the switch to Vanguard with my overall investment portfolio.

I like the Fidelity fund for the lower minimum grants compared to Vanguard ($50 vs. $500). It also has a lower minimum to get started ($5,000 vs. $25,000). But I use the Vanguard fund as well, largely for the ease of transfer of my mutual funds, which happens literally overnight, as I will detail below.



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Goodbye, Capital Gains


The reason it’s more advantageous to give appreciated assets than cash is the elimination of capital gains taxes. There aren’t that many ways to obviate capital gains — I outline the best ways here — and some are almost never advisable, like death for instance. I would advise against death as a tax avoidance strategy 100% of the time.

When you donate appreciated assets, neither you nor the receiving charitable organization owe capital gains taxes. Donating assets can be a particularly powerful strategy if you have large gains, especially if it’s a fund that may not be well suited for your portfolio, like the ones discovered by this random guy, who also happens to be a physician.

I opened my first DAF in 2013 when I realized my taxable account was a pretty random collection of actively managed funds and index funds with unnecessarily high fees that didn’t make much sense in my portfolio. I had been investing early and often, but not especially well.

The markets had been soaring since I started buying mutual funds in 2009. I had substantial gains, was living in a high tax bracket, and was feeling generous. In an effort to simplify, I sold some of the lower performers, donated some of the higher performers, and did more of the same the next calendar year.

My current collection of funds were all purchased within the last few years, so the gains aren’t huge. Still, they’re there for the giving. In order to decide which funds and lots to give, I needed to take a close look at my mutual fund holdings.

I have four funds in two general categories (U.S. Stock and International Stock) in my Vanguard taxable brokerage account. If I were sticking with a simple three fund portfolio, I would have two funds here, but I like to take advantage of tax loss harvesting, so I’ve ended up with partner funds in the account.

Here’s a look at the gains in funds I’m holding. You’ll notice it’s all green. Any red (tax loss) has been harvested.




I’ve got $151,367.52 in gains, most of them short-term. While I would love to get rid of the gains only, it doesn’t work that way. You have to give away specific lots.

I created a spreadsheet from the information Vanguard supplies to assist in my donation decision-making. I added the “% Return” column, using a simple formula. All the rest of the data came straight from Vanguard. I have “Specific ID” chosen as my cost basis method, which is important for both tax loss harvesting and donation purposes.

The overall average gain of my lots in the taxable account is 15.7%. It would behoove me to part with the lots with above average gains. The international funds have gains below the threshold, so I’ll hang onto those. The US stock funds (VFIAX = S&P 500 index, VTSAX = total stock market index) had better gains, and the funds held the longest had the largest gains. I chose enough of them to add up to $100,000 and pulled the trigger.




You can choose which funds to donate online, but unlike when you sell or exchange, Vanguard’s site will not allow you to select specific lots. Grrrrr… It can be done with a phone call or letter of instruction, but this is the 21st century, darnit. I shouldn’t have to send snail mail or talk to anyone, for any reason, ever.




This hiccup was inconsequential, as their preferred method (FIFO) of donating the lots held longest corresponded with the highest returns. These are the lots I want to part with to discard the most potential capital gains. Altogether, the $100,000 I donated had a cost basis of about $78,000, for a $22,000 long-term capital gain.


Calculating the Tax Savings


If I would have sold the funds and donated cash before donating the $100,000, I would owe capital gains taxes on the $22,000. How much would that cost me?

Since I had held all of these lots for more than a year, they would all be taxed at the long-term capital gains (LTCG) rate. So, 15% of $22,000 = $3,300, right?

Wrong. Add in my state income tax of 9.85%, the NIIT / ACA surtax of 3.8% to arrive at my LTCG tax rate of 28.65%. If I had a higher income — enough to put me in the 20% federal capital gains tax bracket — it would be 33.65%. In California, the LTCG tax can approach 37%.

So, donating appreciated funds rather than selling and donating cash saved me $22,000 x 28.65% = $6,300.

Then, of course, there is the benefit of deducting $100,000 from my taxable income. It can get pretty complicated to calculate this one, and everyone’s situation will be different, but factoring in medicare (FICA), federal income, and state income tax reduction at my marginal tax rate, I can expect a tax refund in April of at least $42,000 based on this one big donation.

While the $6,300 is only a relative gain compared to selling funds now (which I would never do), the $42,000 tax refund is very much real, and it should hit my account within days of filing my taxes this spring. In other words, when the dust settles, this $100,000 donation cost me $58,000, and reduced my remaining cost basis in my taxable account by $22,000.


Donate Now, Give Later


The benefit of growing the fund while working is obvious. Our tax code makes it much more beneficial to give when your income is high. If I were to wait until the paychecks stop coming to build up our DAF, the tax breaks would be much smaller.

It makes good sense to give from your surplus, and the surplus will change before and after retirement.

Right now, my surplus is money. I have financial independence, and I’ve already worked one more year since realizing it. Soon, despite the financial setback I instigated, I will have my financial freedom.

In a few years, I don’t anticipate spending nearly as much time, if any, in clinical medicine. Then, my surplus will be time. If I’ve satisfied my family and personal needs for my time, I can afford to be more generous with my remaining free time, which is something I don’t do a whole lot of right now.


i did find 2 hours to ring on black friday
i did find 2 hours to ring the bell on black friday


As I mentioned previously, I don’t plan to give out $100,000 to my favorite charities right away. Much like I don’t spend all of my paycheck when it hits the bank account, I won’t give away all the new DAF money right away, either. Rather, I’ll use it to give an extra $5,000 or so this year.

I have a goal of having a DAF equal to 10% of my investments before retiring early. After the latest donation, the sum of my Fidelity and Vanguard DAFs have more than doubled to between 8% and 9% of my investments. One smaller lump sum next year, which is potentially my last full year working full time, ought to get me there.


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Treat the DAF Like Your Nest Egg


A $250,000 DAF will allow me to comfortably give away at least $10,000 a year indefinitely using a 4% safe withdrawal rule as a guide. I won’t receive any further tax deduction for the annual gifts; I’ve already taken them at the best time, when my income and deduction potential are at a maximum.

The money is invested according to my specification. I keep an aggressive allocation because this is money I can afford to lose, but would like to see grow to its fullest potential. Using Vanguard’s Total Equity allocation, I am invested in an automatically rebalanced portfolio of 55% S&P 500, 15% Extended Market, and 30% International Stock index funds, with an expense ratio of 0.08%.

In addition to the expense ratio, there is a 0.6% account fee. This closely approximates the tax drag on my taxable account as a result of about a 30% LTCG gains tax on a 2% dividend. Fidelity and Schwab have similar fees.


There you have it. The best way to donate a hundred grand. You don’t need nearly that much to get started, though. For $5,000, you can get started with Fidelity Charitable.

There’s no need to wait until you’re close to retirement to start benefiting from a donor advised fund. There is some advantage to giving the most during your highest salaried years, so if you are on a steep upward trajectory, it might be wise to wait a bit. On the other hand, there’s a penalty to waiting until after your peak earning years to fund one.

For more information on Donor Advised Funds, see my posts on the topic:





Have you considered opening a donor advised fund of your own? Does anything stand in your way?




Help support this site’s charitable mission to make donations like the one I just described. How? Sign up to track your investments with Empower, or score some Black Friday Week deals with Amazon. Thank you so much, and Happy Thanksgiving!

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39 thoughts on “The Best Way to Donate A Hundred Grand”

  1. Thanks for posting this… a while ago now I appreciate!

    I’m a LONG way from being in the position to donate $100k but it’s a win-win obviously and look forward to the day I CAN act on it.

  2. Subscribe to get more great content like this, an awesome spreadsheet, and more!
  3. Hi there,

    Unfortunately, donors are being put at unnecessary risk giving up legal control in a DAF in order to get the tax benefits. If you dig a bit deeper, you’ll discover that the touted SO’s on this comment thread are now the largest charities in America, drawing fees on billions of dollars in donations growing their assets at record numbers.

    Also, some banks mentioned above use a distorted 5 year rolling average to boost their payout numbers.

    Questions; why give up control of your donated money? Why not make the impact now, when people need it most?

    Lastly, we could debate payout figures forever, however a major concern I have is if a SO goes bankrupt are the donors funds protected? NO! If you have a DAF, your SO (not you) have full authority over the funds. There is a better way.

    Thank you.


  4. Just found this article (and your website) now, I found it super helpful. This is a topic I have heard about before but your article was very readable and I understand it much better now. It’s given me a lot to think about for my own finances. Thanks!

  5. Wonderful post, POF. I had no idea a DAF even existed. At this point in my life, my donations are no more than a few hundred dollars per year, Amazon Smile, and some goods to the Salvation Army or Goodwill. However, it’s great to put the DAF idea into my mental filing cabinet, for when I’m ready to give more.

    • Funding a DAF is a great way to “bunch” your itemized deductions, too. If the standard deduction does indeed go up substantially, it’s smart to make a big donation one year, take the deduction, then take the standard deduction in other years. That way, you can give from the DAF a little bit each year, but get full credit for having donated all the money at once.


  6. First I really can not wait to donate this amount! Early in our marriage, my wife and I took the Dave Ramsey course and we look forward to the day to give like no one else. Looking forward to dig into various giving options.

  7. I especially like the idea of applying the 4% rule to the DAF. I had only considered it in terms of large lump sum donations. Thanks for the info. This will help my planning for future giving.

  8. PoF,

    As a Vanguard diehard, all my accounts are there, but I like the DAF options from Fidelity better. Is it complicated to donate shares in a Vanguard account via Fidelity Charitable?

    I currently donate to charities by check monthly, but ideally would like to start putting that money in a taxable account and donating it to a DAF after it has LTCGs. What’s your opinion on opening a second taxable account at Vanguard and transferring the shares to the Fido DAF vs opening a Fido taxable account for my monthly giving and also using the Fido DAF?

    I really appreciate your insight!

    • I don’t see any need to open a second Vanguard taxable account; I would just have one. I would guess Fidelity makes it simple to donate from Vanguard, but there might be a little more lag time when you go from one brokerage to another with the donated money. I sort of skirt the issue by donating directly to my Vanguard Charitable account from a Vanguard taxable account, then making a grant from the Vanguard DAF to Fidelity Charitable. But if I were starting anew, I would just go with Fidelity Charitable for the lower minimum grants (and 80% lower amount to open an account).


  9. I’ve just donated cash to charity without even getting a receipt back since it was minimal. I didn’t know that there were so many other ways to give back. It’s very generous and kind of you to take action and share it with others. 🙂

    • I think it’s great to give in whatever way you can.

      Personally, I like to optimize my giving. I want the charitable cause to get the most dollars for each dollar I give. In the tax bracket I’m currently in, it costs me $100 to give about $170. If I gave cash, the charity would only get $100. By saving receipts and itemizing deductions, the recipient gets more at no additional cost to me. It’s like getting a government match for every dollar you give.


  10. Actually your view on donation is really great. The donation in liquid form is just for short time, where as this idea of donating in the form of DAF will be really helpful for the peple at the receiving end.

  11. The DAF seems like a really interesting idea. And the fact that Vanguard has so many financial facilities is really great. Your idea is excellent and very inspiring. More people like you are responsible for helping the less fortunate and inspiring millions. Someday, I do wish to apply your ideals and ideas.

    PS: Waiting for the day when I earn enough to donate a hundred grand

  12. So how exactly did you end up with 90k of short term gains in VTSAX? LOL on that I think, or I am missing something….?

    Love the rest of it. We just did the same thing and to leverage the savings are using it to shield income from converting part of a IRA to a Roth IRA. I’m pushing my luck by converting the Roth next tax year hoping to further arbitrage our tax rates this year vs. next year. (I’d do this the opposite way if Clinton had won….)

    Even better, we are using a DAF company where I can keep the assets invested in any stock/mutual fund and take much more risk than the Fidelity/Vanguard options currently have available. I am donating an SVXY position that has a 75% capital gain. I may well keep the money in that position.

    Math wise our 100k donation saves roughly 40K in taxes and cost us 60 thousand initially. I then plan to convert 40k of the IRA to Roth and shelter it from tax forever with minimal slippage based on tax rates—and still have the icing on the cake of the charitable funds to donate over time.

    Running out of time for this strategy this year. Many funds have 12/16 as a final date for new accounts funded with stock and some have already passed. If anyone is considering it do it now!

    Great article and great site! Thanks

    • Glad you enjoyed the article, Eric, and happy to hear you’re using a DAF. Can I ask through which company? The readers might be interested in a DAF with more flexibility. You’re the second person to tell me you also donated $100,000 this year. Fantastic!

      The $90,000 in short term gains in VTSAX is accurate. That is a screen capture from my Vanguard account, edited to remove current balances and account numbers.

      In January, when the markets were down about 8% on the year, I tax loss harvested a large position in VFIAX to VTSAX, and it has gained over 15% since then. Most of my additions to taxable this year have been in VTSAX as well.

      I made my mega Roth IRA conversion a few years back. Now I’m able to make backdoor Roth contributions annually without any issues with the pro rata rule.

      Congratulations again on your generous moves!


      • Love the site. That’s a great short term gain to sit on, I may have to revisit some tax loss harvesting strategies!!! Congratulations.

        Backdoor Roth’s are great if you don’t have traditional IRA funds to trip you up. Your conversion may have been painful at the time, but you will now get to enjoy making that extra contribution every year!


        Hope the information is helpful for some people.


  13. I happened to be working on tax planning this weekend, and read your article. For my situation, donating $100k in highly appreciated stock(20 x cost basis) saves me a total of $48k in federal and CA state taxes. If I instead sell this stock to help pay for my tax bill, I would generate an additional ~$37k in income taxes, leaving me with only a $15k ($100k – $37k – $48k) benefit.
    I’ve been looking for a better way to donate to charity, DAF fits the bill perfectly. Leveraging $15k into $100k for charity this year, and being able to grow that amount for charity in future years, is awesome! Hope others explore this possibility…
    Thanks again!

  14. Very timely post. Just wanted you to know that your article resulted in another 100k charitable donation. 🙂
    Thank you and Happy Holidays!

    • Happy Holidays to you, Joe!

      Comments like yours assure me that the time I put into this site is well spent. You’ve made my weekend.


  15. Wow…what a great post! I followed the fidelity link and just set up our first DAF. When we opened a brokerage account post residency (2 1/2 yrs ago) I had no idea what I was doing with investing. I didn’t know an index fund from a bond fund from an indonesian microcap fund. The day I opened the account I did several things simultaneously: 1) ordered the white coat investor off of amazon.com, 2) funded the account with the first 50K we saved (and all I had to my name) and 3) bought a 100 shares of google (at $500/share). My microvascular recon attending always told me 14 hours into our most painful residency cases, “sometimes even a blind squirrel finds a nut” and seeing as google appreciated about 50% since my ill advised purchase he was right! I’ve been trying to figure out how the hell to get these into my now simplified otherwise fully indexed portfolio without paying a significant amount in capital gains. Seeing as we donate thousands to several of the same non-profits every year setting up a DAF made perfect sense. Keep up the great work…Thanks!

    • I’m so glad to hear that, Millenial MD!

      A DAF would be a perfect landing spot for those Google shares. I think you’ll be happy with the Fidelity setup. They make repeat grants very simple.


  16. Thank you for your generosity! And thank you for your post! Timely indeed. I have considered this as well and now have the information and encouragement I needed.

    Yet another reason to consider this now is the potential tax cuts being considered by our president and congress. In 2016, we may be experiencing our highest marginal rate (particularly those of us planning to cut back on work and income in the upcoming years). With these high marginal rates, we may as well take advantage of the deductions now.

  17. Awesome stuff on the DAF! I wasn’t clear about the metrics, so now I’ve got a better idea. Thx.

    What are your thoughts of just paying higher taxes to our benevolent government and let them redistribute our money to the less fortunate?

    On the same vein, what about NOT retiring early, and continue working and paying taxes to donate more to helping society.

    Working more to pay more taxes is one of the things I mention in the Darkside of Early Retirement post.


    • I’ve read that one. Welcome to the Dark Side…

      Speaking of the dark side, I’m not sure I trust our government to be the most efficient distributor of resources. Also, consider that giving an extra dollar to the federal government costs me a dollar. With a marginal tax rate approaching 50%, I can give nearly $2 to a 501(c)(3) charity and it costs me a dollar.

      If the charity is twice as efficient as the government, I’m seeing 4x more good for my dollar. Also, I did the math in this guest post @ Investment Zen, and realized I had paid about $1.6 million in taxes over my ten year career. I’m not exactly in the mood to give extra.

      As David S. Pumpkins would say, “Any questions?”


  18. What I like about this approach is that if you envision giving x% of your income to charity in retirement, it’s more efficient to simply transfer x% of the assets upfront and then donate the cash flow. There is a huge tax benefit: the time value of money from pulling forward the tax write-off and the tax rate arbitrage (higher marginal rates while working, as well as saving on capital gains taxes during retirement). The tax benefits remind me a little bit of the Tax-Loss-Harvesting mechanics. Only, there is no annual maximum like $3,000 p.a. for the TLH. Only a maximum contribution of 30% of the AGI.
    Very intriguing!
    Happy Thanksgiving weekend everybody!

  19. That looks like a smart way to do it. We banked my final year’s pay & bonus into a ‘giving fund’, but most of it is sitting in a money market fund right now. A DAF will make sense in a couple years, but we can’t use the tax deduction at this point (see: Pease Amendment). It is a lot of fun to have the $$$ to support almost any cause you wish – we’ve met some interesting organizations since I early retired in April.

    • It’s a great way, and the Pease provision DOES NOT reduce your deduction for charitable giving. It is simply a surtax on high earners. Read all about it if you don’t believe me.

      You’ve got a month left in this calendar year if you want to revisit the idea.


  20. This is a compelling case for why you should fund a Donor Advised Fund during your working years when your income is the highest. You mentioned in the previous post that Vanguard would start making donations on your behalf if you didn’t make a donation. Are there any limits to how long you can keep money in a DAF? Any rules that require you to make distributions of a certain amount? You mentioned in this article that you’d like to be able to donate $10,000 indefinitely. What happens to the DAF upon your death? Do you set up a charitable beneficiary that receives the balance of the account?

    • Thank you for reminding me that I need to start enforcing a strict 2 question limit in the comments, BLI!

      Here’s a link to Vanguard Charitable’s 36 page Policies & Guidelines.

      No time limit that I’m aware of. I expect to have mine as long as I live and breathe; my sons will direct the funds after that.

      Here’s what happens if you don’t grant any money for five years. All you have to do is make one $500 grant every five years. Minimum account activity
      Accounts must recommend and issue at least one $500 grant every five years. Vanguard Charitable will attempt to contact account advisors after four years of grant inactivity to remind them of this policy. If repeated contact attempts are unsuccessful, Vanguard Charitable reserves the right to take the following actions:

      Inactive accounts with balances greater than $15,000:
      • Issue a grant for 5% of the account balance to (i) the directive of the Succession Plan on file if the plan grants funds directly to qualified public charities, or if the Succession Plan does not immediately direct funds to a public charity, then to (ii) the Vanguard Charitable General Fund.
      • In the following years, if account advisors do not respond to outreach attempts and recommend a grant, issue an additional grant for 5% of the account balance to one of two options noted above.
      • If the account remains inactive for 3 consecutive years, enact the succession plan. If the succession plan does not direct grants to a qualified public charity or charities, the funds will be distributed to the General Fund.


  21. Question PoF…
    So I have a 401k with my company and also have a taxable account. I contribute much more to my taxable and my 401k is limited with options. Due to this, I decided to make my taxable acct my true FIRE acct with roth iras being a bonus.
    In my situation, how would you about about donating the money from 401k? Just draw it down and donate it 4% at a time once I get to retirement? I want to maximize tax efficiency so that I dont get taxed on it. Also, I really dont want to start donating until I Retire like 20 years from now. Thanks for your help!

    • When you separate from your employer (retire or change jobs), you should be able to roll over the 401(k) to an IRA with any brokerage you like (Vanguard for example). Then you can choose low cost funds, and if you want to access the money before age 59.5, consider starting a Roth IRA conversion ladder.

      To take full advantage of the tax benefits of a DAF, I would fund it from taxable. Waiting until you’ve been working for 15 to 20 years should ensure that you have sizable gains that will disappear when you donate them to the DAF.

      I wouldn’t donate from the 401(k) / IRA because that has already had the advantage of tax-free growth, unlike funds in a taxable account.


  22. This makes a compelling argument to give now, during peak earning years. While I’ve been aware of DAFs for a while, I haven’t taken the time to dig into them. This has been informative, thanks.

    I do have a follow up question: have I understood correctly that from the POV of the recipient of the charity giving through a DAF causes them to receive 0.6% less than if you had given to them directly? I think the pros outweigh this con (assuming I have understood this correctly), but I do like having a complete list of pros/cons in my head when evaluating something.

    • Thank you for the question, Mrs. BITA.

      I would refute that assertion. It’s not like GoFundMe where you put in $100 and the recipient gets about $92.

      When I make a grant from the DAF for $500, the recipient receives $500. The 0.6% is the annual fee assessed on your account. It’s similar to the tax drag my dollars would see if they were left in my taxable account instead, at least while I’m working.

      Also, if you put $10,000 into the DAF and immediately granted it to charity, the $10,000 wouldn’t shrink at all, save for maybe a few pennies a day. If left for a year, it would shrink $60.

      One last way to look at it:

      If I am willing to part with $58,000 from my portfolio now, the DAF goes up $100,000.

      If I wait until I’m retired, subtracting $58,000 from my portfoliio might result in only $65,000 to $70,000 for the DAF, since I won’t be in a high marginal tax bracket, and might have zero federal income tax.

      Happy Thanksgiving!

  23. Boom! This is the explanation I needed. A DAF seems like a no-brainer. Way to be generous & smart at the same time! Happy Thanksgiving!

  24. Boom! This is the explanation I needed. A DAF seems like a no-brainer. Way to be generous & smart at the same time! Happy Thanksgiving!

  25. Great article PoF! I don’t have enough annual surplus yet to feel comfortable opening up a DAF, but I can see that there may be one in my future if things keep going well. Thanks for sharing – very informative!

  26. Good explanation, POF. I need to spend time on both Vang and Fid sites to understand this more. DAF makes a lot of sense.

    • Thanks, TFR!

      If I were only going to have one, I would choose Fidelity. I don’t always want to give the $500 minimum grant that Vanguard requires.



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