How to Give Like a Billionaire: Vanguard, Tax Deductions, & Nuns

I know what you’re thinking. For sometime now you’ve been wondering what exactly Mr. and Mrs. jlcollinsnh have in common with Bill and Melinda Gates. Here it is: We both have Charitable Foundations

Now you’re thinking, “I knew it!  jlcollinsnh is a billionaire!”  In this you’d be, sadly I must say, mistaken. More monk than minister, I’m afraid.

We talk a lot on this blog about investing and building your own F-you Money stash. Very little time is spent on, well, spending it. Since we  personally don’t much care for owning things we’ve not much to say. We like travel. We do spend on that. Sending our daughter to college was money well spent, as she so thoroughly embraced the experience.

But the money we’ve spent that has provided us with the most pure pleasure is that we’ve been privileged to give away.

In fact, I can specifically pinpoint the $1200 that has given us the most satisfaction return of all. I hesitate telling this story as it will be easy to read it as bragging when it’s only meant to illustrate. Hope you take it in that spirit.

Many years ago we attended a charitable auction held by the Catholic grammar school our daughter then attended. We had always been impressed with the teachers and the Mother Superior who ran the place.

One of our favorite local restaurants was Parkers. Parkers had donated for auction a gourmet dinner for ten. On the spur of the moment we decided to win it and gift it to the school’s teachers.

Bidding was spirited but as the amounts reached the actual cost of dinner for ten at Parkers, the competition dropped off. At around $1200 we were the winners.

When I gifted it to the Mother Superior I also gave her two obligations. First, she would have to choose which ten, of the about 15, teachers would get to go. Second, she herself would have to attend. See, we know this Mother Superior and needed to head off her selfless ways.

Parker stepped up

When word spread a couple of very interesting things happened. Parker stepped up and expanded his donation to dinner for 15 so everyone got to go. Another bidder offered to foot the bill for the wine.

Well, you know what happens when you mix fine food, wine and Catholic school teachers. Let’s just say, a good time was had by all, and leave it at that….

In addition to personal pleasure, one of the benefits of charitable giving is the tax deduction. Of course, to gain this benefit you must itemize your deductions on your tax return. But if you have less than $11,600 (married and filing jointly, $5600 if single) in itemized deductions you are better off taking the standard deduction and saving yourself the effort.

Five or six years ago it occurred to me that two life changes were coming down the pike that would affect my personal tax situation. We were planning to sell the house and I was planning to retire. Without the house and it’s associated deductible costs we’d no longer be itemizing. Upon retiring I’d be in a lower tax bracket. Both these things would be lowering the tax advantage of charitable giving. The solution:

The JJ Collins Charitable Fund

If you’ve been reading this blog much you already know I’m a big fan of Vanguard. So it should be no surprise that in setting up our foundation we used The Vanguard Charitable Endowment Program. Here’s why:

  • You don’t have to be a billionaire. You can open your own foundation with as little as $25,000. Fancy building not included.
  • You get the tax deduction in the year you fund your foundation. So I got to take the tax benefits when they mattered most to me.
  • If you have stocks or mutual funds or other assets that have appreciated in value you can move these directly into your charitable foundation. You get the tax deduction for their full market value and you don’t have to pay any capital gains taxes on the gain. Double tax win and more $$ for your charities.
  • You can choose a variety of investment options so your donation grows tax free while waiting for you to allocate it.
  • You decide what charities receive your money, how much and when. You can set this up to happen automatically.
  • You can add more money to your foundation whenever you choose.
  • Because it is run thru Vanguard, expenses are rock bottom.
  • Now I can tell unwanted solicitors, “We only give thru our foundation. Please send us your written proposal.” We’ve gotten exactly zero proposals.
  • It keeps our personal names off the lists some charities sell to future solicitors.

In addition to the tax advantages this offers, it also plays into some of my conclusions regarding charitable giving:

  • It is best to concentrate your giving. We have selected two charities.
  • Giving small donations to many charities might be satisfying to you, but it dilutes the impact and a greater percent of your gift is eaten up in the processing of it.
  • Many small donations also gets you on many mailing lists.
  • Never give to phone solicitors.
  • The more I see a charity advertising, the less likely I am to believe they are focused on delivering my cash to those they claim to serve.
  • You need to do your homework. In addition to scams, lots of charities simply aren’t very efficient in delivering your dollars to those in need. You can check them out here:

You don’t need a charity to help

There is also something to be said for giving outside the traditional, and tax-deductible, places. Helping your friends and neighbors directly isn’t deductible, but it has immediate benefits all around. This is something I’ll be trying to do more of in the coming years. 

Finally, while giving is a fine and pleasant thing, no one has an obligation to do so. Anyone who tells you differently is trying to sell you something, most likely the idea of giving to them and/or their pet projects. As individuals we only have one obligation to society: To make sure we, and our children, are not a burden to others. The rest is our personal choice. Make your own and make the world a far more interesting place.

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Important Resources

  • Talent Stacker is a resource that I learned about through my work with Jonathan and Brad at ChooseFI, and first heard about Salesforce as a career option in an episode where they featured Bradley Rice on the Podcast. In that episode, Bradley shared how he reached FI quickly thanks to his huge paychecks and discipline in keeping his expenses low. Jonathan teamed up with Bradley to build Talent Stacker, and they have helped more than 1,000 students from all walks of life complete the program and land jobs like clockwork, earning double or even triple their old salaries using a Salesforce certification to break into a no-code tech career.
  • Credit Cards are like chain saws. Incredibly useful. Incredibly dangerous. Resolve to pay in full each month and never carry a balance. Do that and they can be great tools. Here are some of the very best for travel hacking, cash back and small business rewards.
  • Empower is a free tool to manage and evaluate your investments. With great visuals you can track your net worth, asset allocation, and portfolio performance, including costs. At a glance you'll see what's working and what you might want to change. Here's my full review.
  • Betterment is my recommendation for hands-off investors who prefer a DIFM (Do It For Me) approach. It is also a great tool for reaching short-term savings goals. Here is my Betterment Review
  • NewRetirement offers cool tools to help guide you in answering the question: Do I have enough money to retire? And getting started is free. Sign up and you will be offered two paths into their retirement planner. I was also on their podcast and you can check that out here:Video version, Podcast version.
  • Tuft & Needle (T&N) helps me sleep at night. They are a very cool company with a great product. Here’s my review of what we are currently sleeping on: Our Walnut Frame and Mint Mattress.


    • jlcollinsnh says

      piece of cake to set up.

      one other thing I forgot to mention. If you have stocks or mutual funds or any assets that have appreciated in value you can move it directly into charitable foundation. You get the tax deduction for its full market value and you don’t have to pay any capital gains taxes on the gain.

      Double tax win and more $$ for your charities.

      think I’ll add this into the post….

  1. femmefrugality says

    That’s really amazing. I’m nowhere near ready to set up my own foundation, but when I am I’ll know where to go now 🙂 I really like that kid at Duke’s blog…thanks for sharing.

    • jlcollinsnh says

      thanks Tom…

      Glad you liked and to see you’re still reading this stuff. Please give your dad my regards.

      Mmmm, wonder if I can get this blog classified as a charity….


  2. Kari@Small Budget Big Dreams says

    I have to admit I don’t give as much to charity as I’d like, but as my income grows that will probably change. I do have to admit that I sort of think of all the unpaid overtime I work as charity to the homeless (I’m a social worker at a homeless shelter). I love that you won and gave that dinner to the teachers. My mom is a public school teacher and they deserve so much more credit then what they get. They are teaching and shaping tomorrow’s leaders after all.

    • jlcollinsnh says

      Hi Kari…

      thanks for stopping by, and welcome.

      Giving is, as you know, not just about money. I have a great friend from high school who retired and returned to school to get his masters in social work. It is a tough and often thankless field.

      Each year I work as a volunteer with VITA (volunteer income tax assistance) helping lower income people complete their tax returns. It’s fun for me and I get to meet some interesting and wonderful people. Certainly shatters the common assumptions about the poor.

      My guess is your work with the homeless does the same.

  3. Cindy says

    Wonderful article! Doing your homework is an important step to charitable giving. Vanguard Charitable is a great way to give to your favorite 501c3 charities and the homework is done for you! did an excellent job relaying all the reasons why a donor-advised fund is a good option for philanthropy. Thanks for being such a great ambassador to giving!

  4. Fritz Hahn says

    Hi Jim-
    Thanks for your informative article. As a social worker I am keenly interested in meaningful gifting – especially when considering current diminished funding in light of increasing demand.
    Some thoughts from the book “Getting to Maybe: How the World is Changed,” by Westley, Zimmerman and Patton: think of the Grameen Bank model for microloans for entreprenurial start ups. Outcomes, accountability and tests of inference are important for established programs, but as a potential (micro) funder for start ups consider: (quoting from “Getting to Maybe…”):
    1) Support learning as a meaningful outcome – and reporting on learning as a form of authentic accountability.
    2)Create and nurture experimentation and learning about social change, especially failed policies and initiatives.
    3) Support small “safe-fail” initiatives to learn what works and doesn’t work before implementing policy changes widely.
    Thank you for your wrtiting and
    thank you to your readers for their responses.
    Fritz Hahn, Taos New Mexico

  5. Mr. Risky Startup says

    Thanks for the post. I may be crazy, or it may have something to do with me living in Canada, but I refuse to use charitable donations as a tax-break. It may be different in the US, but in Canada government does a pretty good job providing social assistance to all those in need. Yes, I am sure that there is some abuse, some people are lazy jerks who suck the system, but vast majority (maybe 98% of the money) goes to those in need. And yes, government on occasion does something ridiculous and often wastes money, but I bet that overall, they are more efficient than any non-profit organization could be.

    Secondly, I must say that I disliked Bill Gates for a very long time – as a nerd, some of his moves did slow down the development of the new technology, some great things never took off as his inferior product simply steam-rolled over it… However, what he is doing now, not only with his own money, but also by having other billionaires donate even more – is nothing short of amazing. There are thousands of children in this world that are alive today thanks to his work and contribution.

    • jlcollinsnh says

      Hey Mr. RS….

      good to see you here and thanks for commenting!

      yeah, I gather Canada throws a wider safety net than we do here in the US. Although a lot of tax dollars are spent on social causes here too.

      The argument I’d make for charities over government in handling these things is that charities have to win you over to get your money. governments just take it. accordingly it seems to me the charities have more motivation to run efficiently.

      that said, I think the even better choice is low key, local help provided to people and situations we can know personally. of course, here in the USA those kind are not deductible. that’s why I funded my foundation during my high tax/valuable deduction years. now, I’m free to do more of the more personal stuff and not worry about the deductions.

      Bill Gates seems to be a person that others have very strong feelings about. As for me, he was just a good foil for this post.

      • Mr. Risky Startup says

        I agree about keeping the charity close to home.

        P.S. Forgot to mention in my earlier post – I shared some of your posts with my better half and she says she loves your writing style.

        Thanks for taking time to write – it is kind of you to share your story to help others who are striving for the same result.

        • jlcollinsnh says

          thanks for letting me know and please give your lovely bride my thanks and regards.

          of course now that I know she’s reading I’ll be expecting her to comment. 😉

  6. Tom Mullen says

    Wise words. And they can only help make the world a better place! On reading, I originally thought that that Parker may be the wine guru, then realized that though he’s not, he is definitely a guru, and a very generous one at that. Inspiring story. Thanks.

    • jlcollinsnh says

      Hi Tom…

      Glad to see you found your way to this post. It’s one of my personal favorites.

      We never knew Parker all that well, just as diners at his joint. Still, I remember a pretty nice wine list and I’d be surprised if he didn’t know his way around it.

      He sure knew his way around food!

  7. cv says

    Dear Mr. Collins,

    Thank you so much, first of all, for your help on my questions and comment previously on consolidating my assets. I enjoy reading all your posts- they have a very unusual flair. I often find myself reading them over again and taking away different points.

    I really appreciate your perspective on “giving”, not acting out of perceived duty, but out of sincere wish to benefit others. I was wondering if you can shed some light on my personal giving scenario:

    I’ve been working regularly for approximately 8 years, have been working seriously hard on stashing my FU money since the beginning of this year and planning to work full time for no more than another 10-15 years.

    I tithe a portion of my take home paycheck to the local church i go to (by choice), which comes out to 5k a year. I am not yet a registered member, still feeling the parish out- last year, they did not even bother sending me a tax receipt because I was “not registered”. Due to the location of this parish, there are some seriously wealthy patrons, including former domino farms pizza owner. So I am thinking of taking my contribution elsewhere. Obviously the funds at the moment is too small to start any kind of foundation; are there other options (aside from the uber-low-yield savings account at the bank I can contribute regularly and grow the money in, and donate a lump sum at the end of each year?

    I also volunteer 60-70 hours a year, and regularly take donations in if for some reason i am not able to meet the tithe amount during a given month.

    Hope this makes sense.

    • jlcollinsnh says

      Hi CV…

      My first reaction is I’d instantly stop giving to any organization so unappreciative. 5k is a lot of money!

      There are just too many wonderful options. Just click on the Charity Navigator link in the post and you’ll find plenty.

      If the deduction is less important to you, as it is to me now, you might consider what I suggest at the end of the post: Direct and personal giving to friends, neighbors and local organizations whose work you value. These have little or no overhead or fund raising, so every penny goes to work helping.

      As for where to keep the money until you donate, even as low as rates are, the bank account is still the place. As it is for any money you’ll be giving/spending/using in the next few years. Investing is long-term: 5 years minimum. Decades ideally.

      You could also start an investment fund with the annual 5k each year, not yet donating any. In five years or so you’ll be at the 25k mark for the

      You could then set it up and authorize distributions while adding to it as you chose. This is what I’d do. You’ll be creating something that will last longer and do more good.

      Good luck!

  8. Jim says

    Great post, never gave ‘starting a foundation’ any thought because I didn’t understand the benefits, but your post helps shed light on them. I love Charity Navigator, never make a donation without checking them out first, be sure to check their ranking!!

    • jlcollinsnh says

      Glad it helped, Jim!

      Absolutely. Whether contributing directly or thru your charitable trust, it pays to vet any organization before sending them your money!

  9. Workinghard says

    I don’t know how many times I’ve thought about a charitable trust fund. It’s been on my someday wish list. However, it’s my understanding that any money in the fund can only go to qualified non-profit or tax exempt organizations. Is that correct? Or can the money be used to help individuals in need? We give 10-12k a year to people rather than churches or organizations. I also prefer giving anonymously which calls for some creativity and using people out of state to help. It would be nice to have some of the advantages of a charitable trust fund.

    Thanks for addressing this topic! Now to read your other blogs.

    • jlcollinsnh says

      Welcome WH…

      Correct. Your fund can only contribute to qualified, established charities. I suspect this is because, since it is tax deductible, the same rules for IRS charitable tax deductions apply.

      As it happens, like you, I frequently prefer to give directly to individuals and small organizations that may not qualify.

      So what I do is occasionally fund my charitable trust with larger donations that get me over the IRS standard deduction for the tax benefit. This money is then distributed over the next several years.

      At the same time the money I choose to give anonymously and to places not qualified I give randomly and without concern for the tax break.

      Hope that helps.

      • Workinghard says

        Thanks for replying and everything you’re doing to help us (me)!

        I don’t care about the tax advantages per se of a charitable trust but the anonymity would be great.

  10. bookaunt says

    Just to let you know that you can open a charitable gift account at Fidelity for $5000 while you are waiting to build a bigger stake.

    • jlcollinsnh says

      Good to know, bookaunt.

      But for smaller sums like $5000 I would just distribute the cash directly to the charities of my choice without bothering with a charitable trust.

      Such trusts, in my view, are better at providing an immediate tax advantage for a larger donation that will be distributed over time.

      For instance, unless you have other deductions $5000 will be under the standard deduction amount and no tax benefit will be realized.

      But if you fund your trust with 25k and then distribute the money over five years at 5k per year, you get a very valuable 25k deduction in the year you fund your trust.

      Make sense?

      • bookaunt says

        There are are times when even a $5k charitable fund can be useful. It worked for us a couple of years ago when we wanted to sell some stock that had a significant capital gain. By funding our gift fund with that stock, we were able to shield the profit from taxes – worthwhile to us even though the amount was not much over $5k (but we did have other deductions).

        Also – when looking at setting up one of these funds, note that both Vanguard and Fidelity charge an annual cost/maintenance fee.

  11. Josh Fire says

    Hello jlcollinsnh-

    My name is Josh, and I have an idea that I think can bring the FIRE community together and help starving children in Africa while providing evidence to support or reject the 4% SWR model.

    I would like Wade Pfau, Mr. Money Mustache, Mad Fientist, and yourself to become board members of a Michigan-based 501c3. Together, we would:

    1. Incorporate the 501c3.
    2. Solicit donations from the FIRE community via our blogs for our 501c3 with a minimum target of $25,000 to open a Vanguard charitable fund.
    3. Before the first annual report is due, we would dissolve the 501c3 and transfer all of the funds to the Vanguard charitable fund. We would pick how the funds are invested at the start.
    4. We would set up the charitable fund to donate 4% each year to the charity that best serves our goal of feeding children in Africa.
    5. We report out on the portfolio size each year and show that the 4% SWR model works (or not).

    I will do the legwork to create the 501c3, write the Articles of Incorporation, and I can even donate $1000 (maybe by matching donations) to the 501c3 to get started. I can also provide conference calls for us to meet as needed.

    This blog post of yours and mine at gave me this idea.

    Please let me know your thoughts, and feel free to contact me to discuss further. I already emailed Wade Pfau and Mr. Money Mustache, and I am going to try to find contact information Mad Fientist. If you have a way to contact him, I would love your help in getting him involved.

    Best regards,

    • jlcollinsnh says

      Hi Josh…

      Interesting concept and certainly a worthwhile cause.

      Personally, I am trying to eliminate things from my plate, rather than add any more.

      That said, Mr. MM and MF are both friends of mine and I’d enjoy a project that brings us together. Plus, I’d be very interested in meeting Mr. Pfau.

      For your consideration, here are my concerns:

      1. Charitable giving is a very personal and sometime contentious subject. See the comments in this post:

      2. I’m not sure people need to go thru us for their giving.

      3. No matter what charity we select, there will be those who find fault.

      4. Charities are imperfect organizations and, even using sites like Charity Navigator, not entirely transparent. When we chose to give to one on our own, we accept that risk. I’m not sure I’d be comfortable encouraging others to follow my lead into any specific charity.

      5. I don’t think we’d prove anything regarding the 4% rule. The time horizon is simply too long for it to prove out and even then we’d only be proving that it worked, or not, for the year we started.

      In any event, please keep me posted on your progress and the input of the others.

      All the best!

  12. Mary says

    I can’t thank you enough for this post.

    I realized that 2014 would most likely be my last year in the 33% (+9.3% state) marginal tax bracket, as I am drifting towards retirement, and this gave me the perfect solution to three problems. 1)I had a substantial sum in VGSIX that was worth roughly double my cost basis, 2)I felt that my asset allocation had too much exposure to RE, and 3)I earned more money in 2014 than I had anticipated, meaning I would probably get hit with a penalty for underpayment of estimated taxes. So I opened a Vanguard DAF last month and funded it with the VGSIX shares, and boom, all problems solved!

    I hope you have a wonderful 2015!

    • jlcollinsnh says

      Hi Mary…

      Thanks so much for letting me know.

      Sounds like a perfect solution for you, and your charities.

      Glad to hear this post came to you when needed! 🙂

  13. Howard says

    Thanks for this information.

    I’m a little confused by the vanguard charitable site. Do you have to donate to a 503(c) organization? I assume so as it is tax deductible?

    I’ve had the thought of giving to some friend’s kid’s college expenses in the future, if/when I have the money. But this would obviously not be tax deductible. Would it be easiest just to do this out of cash, or could I set up some grant with $50k and give 4%/year? Would be cool to have my own: “Mr H’s educational grant for the advancement of science”! 🙂

    • jlcollinsnh says

      Hi Howard…

      Yep, you must contribute to charities the IRS recognizes.

      For contributions other than those, you’ll need to fund from other sources and it it won’t be tax deductible. I once gave 25k to cover grad school expense for a friend in just this way. It’s a great thing to do. Getting a tax break isn’t the only thing. 🙂

  14. Matt says

    Mr. Collins,

    Thank you for taking the time to share your knowledge and experience. I have been almost obsessively reading you articles and learning a ton and even some confirmation of decisions/thoughts I have made in the 10 years of my adult working life. The recent move from an amazing job to slightly less amazing job put me in search of what it would take to be FI and tighten up my financial life. As it turns out we have been living on about 50% of our take home pay and investing the rest and are only aprox three years away from having FU money and having the options that go along with it.

    I am working on moving away from a financial adviser (with the 1% AUM fee and expensive funds) who was handling part of our investments and moving it to Betterment account, that I signed up from your article. Every year we give a minimum percent of our income to charity and this post has me researching donor advised funds and the option of transferring all our shares with capital gains into a Vanguard donor advised fund. The other option is to gift them directly to a charity. My question is: Since we will continue to gift that percentage of income (so a minimum specific $ amount) per year in the future could I systematically invest that money into Betterment and then once or twice per year gift that same amount to the donor advised fund using shares with capital gains and avoid the capital gain taxes and/or continue to raise the cost basis of my investment portfolio? Plausible effective strategy?

    Again, thank you and sorry for the long-winded and beginner’s question.

    • jlcollinsnh says

      Welcome Matt…

      Glad you found your way here!

      The advantage of a donor advised fund is to concentrate your giving into a single year for tax purposes and yet still be able to distribute the money (or perhaps the money it earns) over multiple years.

      If your plan is to give a certain amount every year, I don’t see the need for the middleman. Just give directly to the charity.

      Make sense?

  15. Physician on FIRE says

    Yes, the Donor Advised Fund.

    Big fan, having used several of them. I started with T. Rowe Price since that’s where my taxable fund was.

    When I moved my money to Vanguard, I started a Vanguard DAF at I later realized that although the costs were lower than T. Rowe Price’s, the minimum grants were $500. I like to give smaller amounts to a wider array of mostly local charities. Like Josh Fire suggested, I treat mine like a nest egg, giving a little more than a 4% SWR, but maybe give 5% to 6% from it each year.

    I discovered Fidelity Charitable, also mentioned in the comments above. Yes, it can be started with only $5,000, compared to Vanguard’s $25,000, but the bigger advantage for me is the $50 minimum grant. And the fees are nearly identical to Vanguard’s.

    Last year, we gave from $100 to $1000 to 15 different charities, and I imagine we’ll exceed that this year. We give half of my blog revenue to charity, most of it via our Donor Advised Fund.


  16. Mollie says

    I love this post! I also love that it brought fellow social workers out of the woodwork. =) Kudos for giving those teachers a very memorable night out!

    Out of curiosity, does having a charitable foundation help out with taxes when RMDs come into play with an IRA or 403b/401k?

    • jlcollinsnh says

      Thanks, Mollie!

      If you transfer money to your charitable fund directly from an IRA or 401k/403b you get the tax deduction on the amount and avoid capital cains taxes on any gain. Move money out of those accounts then reduces the amount of your RMDs when the time comes.

      This is a much better way to make contributions rather than just out of cash flow you’ve paid taxes on already.

  17. jkenny says

    I just did this (set up a DAF) and it never never never would have occurred to me if I hadn’t read this post many months ago. This. Feels. Great! Thanks (again) jlcollinsnh for all your great practical advice that regular people can follow.

  18. Dan says

    When you open the DAF, is it assigned a EIN/TIN? Are you responsible for filing a tax return? Or does Vanguard Charitable handle the details including tax filings?

    • jlcollinsnh says

      Nope, your Vanguard DAF handles it all.

      I report my contributions on my itemized charitable deductions when I file my tax return and that’s it.

  19. Paul Sheridan says

    I’m attracted to this idea, but I can’t seem to make it work. I think the problem is that I would normally itemize (so the first 12,700 I move to the DAF “doesn’t count”), that my tax bracket is the relatively reasonable 25%, and that I’m still in the wealth accumulation phase.

    When I say “won’t work,” what I mean is that if I’m going to give $1,000 a year to charity, my net worth will be higher at the end of the day just giving $1,000 a year in cash, and not getting any deduction for it, versus giving $25,000 to DAF, then giving $1,000 a year out of the DAF and taking the $1,000 in cash and applying it to savings.

    This even seems to be true, according to my math, if find a few other itemized deductions in the giving to DAF year, reinvest the tax savings, and give appreciated securities to the DAF.

    Am I missing something? It seems like I’m just not in the right phase of life to make this a good option.

  20. Tandoori says

    JL Collins, you just saved me $50K in taxes. Thank you.
    With a huge tax year this year, and much lower tax years going forward in which we won’t be itemizing, this strategy of setting up a DAF seems like the right approach in my particular circumstance.

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