Using a Donor Advised Fund (DAF) to offset a Roth IRA Conversion

It’s been a while since I’ve wrote out finances, so let’s dig in, and let me preface this by saying that I am not a financial professional; please consult a professional (as I did) before you embark on any significant tax-saving strategies.

Okay, with that out of the way, let’s summarize two things: one, I think charitable giving is important, as I’ve written about before in several different essays. If you have the ability to help others and you’re currently not doing so, or if you wonder if you could be doing more, please consider reading my blogs on this topic, and in particular read about Peter Singer and his philosophy about giving money wisely.

Two, I’d like to have as much retirement income in tax-free accounts as possible - in other words, Roth accounts. I’m happy to pay taxes and contribute to the United States every year, but I also want to do intelligent and legal things to mitigate the tax I pay. Rich people do it, so I figure my family should take advantage of the same strategies when possible.

Now, you’re legally allowed to transfer money from a pre-tax retirement account like a traditional IRA or a 401k into a Roth IRA, but it’s a taxable event, and paying a big extra chunk in taxes is prohibitive most of the time. So even though I want to have as much of our retirement savings in a ROTH IRA so that we can withdraw money tax-free in our retirement, I’m not willing to do so if it means paying taxes now.

With that in mind, I’d like to discuss a method of satisfying both desires - giving to charity and moving money into a Roth IRA - without increasing your taxes.

In 2022 I learned about Donor Advised Funds (DAFs), a device that allows you to move more than one year’s worth of charitable giving into a fund for future distribution. The idea is that if you are able to contribute several year’s worth of charitable giving into a DAF in one calendar year, then you can then itemize the deduction on your taxes. This became especially important a few years ago in states like Illinois with high state and property taxes, because after the SALT tax deduction was enacted, these deductions were capped at $10K. So in 2022, when the standard deduction was $25, 900, it required an addition $15,900 of charitable giving before you could benefit from itemizing your deductions. In 2024 the standard deduction is up to $29,200, so it takes nearly $20K of charitable giving to begin to itemize your deductions.

Now, I’m aware that we should give to give, not to reap financial benefits. I get it. But we can give a whole lot more if we do get a deduction, which is why charitable deductions are allowed in the first place - to spur charitable giving.

For argument’s sake, let’s say you have $100K in a brokerage account somewhere and you like to donate $20K a year to charities (and I recognize that these numbers might be pie-in-the-sky - I’m just trying to make it simple). Depending on your income (there are restrictions, so do your homework) you could take $100K from your traditional IRA or 401K and transfer it to a Roth IRA, and then offset the tax implications for this event by moving $100K from your brokerage account into a Donor Advised Fund. The two events should be close to a wash, and you’ll wind up paying around the same tax as you did last year. And now you have five-year’s worth of charitable giving ready to go!

Even better, you can move appreciated assets into the DAF tax free, thereby avoiding capital gains on that amount. And wait, there’s more! The assets you have in the DAF can grow over time, allowing you to give even more money to your favorite charities!

Pretty slick, eh? To me, it’s a no-brainer, and I’m surprised that this strategy isn’t discussed more on-the financial pages I read.

I studied this method for weeks, wondering if I was missing something, and finally bit the bullet and emailed a financial advisor who I hire from time to time for a flat fee (always a flat fee - never a percentage) and asked him about the above strategy. He wrote: “Love this strategy, we do it all the time. Yes, I approve everything you are planning as described in your email.” He then went on to explain a few specifics to be aware of that were helpful, so please do your homework and get the advice of a professional before you pull the trigger.

If you’re lucky enough to have some assets on-hand that you don’t need immediately and you believe in helping others, consider looking into this strategy. It’s a win win win win.

Cost Savings Techniques

Last week I referenced a New York Times article by Alina Tugend about finances and how many of us compare what we have to those around us and may even be bewildered by how others can afford things we can’t.  In this article, Tugend referenced a website I had never heard before called Mr. Money Mustache.  This website is a rabbit hole of mega proportions, throwing you into a world where every decision you make has financial repercussions.  It’s also a helluva lot of fun, with fantastic advice for people of all income levels, and I particularly love to read the forum where people chime in on various topics, ranging from the sensible to the absurd. 

Mr. Money Mustache is all about achieving financial independence by making smart decisions, and it’s just one website that’s proliferated the F.I.R.E. movement, which stands for “Financial Independence, Retire Early.”  There’s even a new documentary available on-line called “Playing With Fire,” which summarizes the trend of people eschewing mainstream habits in favor of gaining freedom from the spending treadmill. It’s great stuff, and even if you don’t go in whole-hog the way some disciples have, there’s plenty of advice to get you on your way to saving more, borrowing less, and giving yourself a better chance to pursue what you want in life rather than what you have to do due to your financial situation.

I’ve written before about my family’s philosophy when it comes to finances, but I’d like to highlight a few things we’ve done over the last twenty years or so that made an impact.  True, we still have spending weaknesses (for me: records, musical instruments, concert tickets and eating out), but by and large we’ve been able to put our family’s money where it matters most to us (namely, retirement, college savings, trips, and charity).  Here are a few things that have worked well for us:

1)     I cut my own hair.  Yes, I’m fairly bald, which makes this a lot more doable, but it’s an option for many of us.  Savings: about $250 a year over the past 15 years.  Total:  $3750.

2)     My family hasn’t had cable TV for 19 years now.  This is a much more doable proposition today than it was in the year 2000, and if you haven’t already done so, I urge you to cut the cord.  Savings: about $1200 a year for 19 years.  Total: $22,800.

3)     My wife and I have used Republic Wireless for our cell-phone service since 2014, spending on average about $250 per phone verses the iPhone or Samsung Galaxy that cost upwards of $1000.  Additionally, we spend about $25 a month each for phone service.  Today, that’s not a huge savings, but in 2014 it was.  All told, I figure we’ve saved about $3000 in phone costs and about $1200 in service costs since 2014.  Before then I didn’t even have a smart phone, so the total savings is even greater.  (NOTE: I’m ashamed to admit that some of this savings has been offset by my family still having a landline.  My wife won that battle, but family harmony is worth every penny!).

4)     We cut our own lawn, shovel/blow our own driveway, and don’t pay for any kind of landscaping except for tree removal.  At the low end, I figure I’ve saved about $60 per month for six months a year, and maybe another $150 a year for snow removal.  Let’s call it $500 a year, or $9500 savings since 2000.

5)     During my children’s school years, they were allowed to eat one hot lunch per week.  Every other lunch had to be made at home.  Cost savings: not much, really, as school lunch prices are very reasonable in Illinois.  But I feel like over the long haul this rule taught my kids to be more self-sufficient.  My now-adult daughters pack their own food most days and don’t go out to eat as often as they might otherwise.

6)     I save a lot on purchasing cheaper wine at my local liquor store, which often sells overstocked or older wines at huge discounts.  I often buy $15-$30 bottles of wine for $4 each.  Savings?  Well, let’s face it.  Wine isn’t a necessity, so the real savings would be giving up drinking altogether, so I’m not adding this in my calculation.  But it is another example of approaching purchases with a little more wisdom.

7)     My family hasn’t purchased a new car since 2007, and we still own it.  Our other car was purchased used, and that’s the only way we’ll go in the future.  If there are two rules to follow when it comes to spending: always, always pay off your credit card debt each month, and keep your car for as long as possible (and by slightly used cars).  Savings?  Hard to calculate, but let’s figure $100 a month for the past 12 years.  Total: $14,400.

8)     Keep your appliances and outdoor equipment for as long as possible.  I just broke down and purchased a new lawnmower after 17 years of using the old one.  And here’s the real miracle: our kitchen refrigerator is now older than our 22 year-old daughters.  How?  Well, for one, we’ve been lucky.  But also, we don’t particularly care what our refrigerator looks like (it’s not exactly pretty at this point), and I vacuum off the dust from the coils a few times a year.  Who knows if this was the difference, but it’s nice not to have to purchase another one!  Total savings: about $2000 minus the electricity we’re undoubtedly paying for a terribly inefficient appliance. 

9)     We do a lot of home maintenance projects ourselves, outsourcing only when necessary.  And it’s important to understand that I didn’t grow up handy in any way, shape or form.  I’ve simply read, watched videos and asked lots and lots of questions from my friends who are better equipped for this sort of thing.  In the end, we’ve managed to do a few things well, including all interior painting, changing electrical outlets, installing a new circuit board for our boiler, installing our own ceiling fans, installing all of the toilets, sinks and faucets, repairing drywall, etc.  It all adds up.  Also, don’t forget to change/clean those filters on your air conditioners, humidifiers, etc. and stay on top of your auto maintenance.  Savings?  A helluva lot, but hard to measure.  I think conservatively at least $20,000

10)  We put our non-investment savings into an on-line account that earns (currently) around 1.8% interest and we locked our mortgage in at a really low rate (2.8% I believe).  Smarter still would be to not have a mortgage, though opinions vary on this. 

11)  We only pay for a fee-based financial planner, rather than asset-based.  I wrote about in-depth earlier this year. 

12) We clean our own home - not a given where my family lives. I have no idea how much a service costs, but let’s conservatively say $50 a month or $600 year. Total savings over the past 19 years: $9500.

13)  Here are a few examples of ways to save a bit, but more importantly, to reduce waste.  We do these more for the environmental impact than anything else.

a)      This is my favorite: instead of using Swiffer sheets to dust our hardwood floors, we use pieces of fleece leftover from family blankets we made some time ago.  Simply dust, shake the fleece outdoors, and wash.  We’ve been using some of these pieces for over a decade.

b)     We’ve used almost exclusively cloth napkins and real dishes, even when entertaining, for the past 20 years or so.  I abhor using paper and plastic products when avoidable, and cloth napkins look nice and are easy to throw in with the laundry.

c)      I’ve started to use my own utensils and napkins when going to eat at a fast-food restaurants.

d)     We’ve used cloth grocery bags for the past 25 years or so.

e)     We print on both sides of sheets of paper.

f)     For our cats’ litter boxes and our dog’s poop bags, we use the bags that come with products we already purchase: cereal boxes, toilet paper or paper towel packaging, insulated envelopes that come in the mail, etc.  Of course, not having cats and dogs to begin with would provide even more savings – both financially and environmentally – but how to you say no to this face?

There are undoubtedly a lot of other things I could mention.  If I add up all the above highlights, we’re looking at around $85,000 in savings plus the interest earnings and savings from a low mortgage rate.  Not bad, but these days, that can be wiped out awfully quickly just through a kids’ college education.  Crazy, isn’t it?  But it all adds up.  The website Mr. Money Mustache, along with the good counsel of people like Clark Howard and Dave Ramsey, can do a lot to get you on your way to cost-savings.  I hope some of my aforementioned examples speak to you as well.  Happy savings!

Finances, Budgeting and Keeping up with the Joneses

The New York Times recently posted an article on finances and how many of us compare our own lot with those around us.  Too often, we might be reminded of what we don’t have rather than what we do, perhaps leading to feelings of ineptitude or inadequacy.  It’s human nature, I suppose, and these feelings might be more acute in the United States, where the individual is mythologized so vehemently with tales of the self-made millionaire.  We want to believe that what we have is a result of what we’ve earned, and if we don’t have as much as our neighbor, it must surely be because they’re doing something right and we’re doing something wrong.  I generally don’t harbor strong jealousies, but I must admit to being bewildered by the sheer volume of opulence that surrounds me in the Chicago suburbs.   Surely, there can’t be that many investment bankers and surgeons, can there?

But as the Times article highlights, when it comes to finances, things may be a bit more complicated than they appear.  A successful friend of mine once touted that he was a self-made achiever, failing to mention that his parents had paid for his college education and his first car.  People can be very sanctimonious when it comes to finances.  Sure, some people are well-off and have earned every penny, but for others wealth might be – in part – due to a sizeable inheritance or familial assistance with a home purchase or college expense.  Hell, if my wife and I hadn’t saved money for our three kids to go to college, we might be living a fairly opulent lifestyle too!  For others, opulence might merely be a mirage paid for with massive amounts of debt.

Regardless of the circumstances, we all make financial decisions, and it’s important to align those choices with our values.  Far too many of us make short-sighted and boneheaded financial choices, as I’ve written about before, but if your choices are guided by your values, then it doesn’t matter what your neighbor has or doesn’t have: you’ll be putting your money where it matters most to you.

So as you drive past your neighbor’s house, keep in mind that they might not have saved for college tuition as you did, or that they don’t put away a large percentage of their income for retirement as you do, or they don’t give a sizeable amount of money to charity as you do.  Or maybe they do and still have enough leftover for a Tesla and a luxury vacation to Tahiti.  If so, good for them! 

And if you’re someone who hasn’t been able to do any of the above, who maybe has made poor decisions in the past, try making a financial plan according to your values, align your choices according to that plan, and stick to it as best you can without worrying about keeping up with the Joneses.  You might find that you have more money available than you realize to put towards what’s important to you. And consider reading my blog from three years ago about twenty pieces of financial advice that I wrote for my children.

The Times article mentioned a blog I had never heard of before: Mr. Money Mustache.  Next week I’ll write about this, the FIRE movement it espouses, and some personal money-saving strategies I’ve found useful.

Index Funds and Financial Planners

There’s been a lot of hubbub in recent financial publications about index funds, and not surprisingly financial planners have had the most to say about it, since index funds in many cases make financial planning largely unnecessary.  When something starts to encroach on your turf, you do what you can to protect your turf. 

This appears to be the case for Robert C. Lawton, who wrote an article for Forbes last month, making the claim that index funds are often not the way to go because they absorb 100% of market downturns and by definition ensure only average returns. His advice?  To use index funds for asset classes that are “widely covered and researched,” but to use actively managed funds for all other asset classes.

But Rick Ferri – also for Forbes – wrote a sort of rebuttal to the aforementioned article, summarizing research done by Jason Zweig of the Wall Street Journal that shows how Lawson’s conclusions were based on a Fidelity report that excluded “high fee active funds and poor performing active funds.”   Fidelity has since removed public access to the study.

Oops.

If all of this is gobbledygook to you, I highly recommend reading about index funds, asset allocation, asset growth and financial planners’ abilities to beat the market.  I’m not a financial genius, but here’s what I’ve learned:

1)     Financial planners typically charge you 1% of your assets to manage your money.  Sometimes even more.  So if you have $1 million in assets, you’ll pay your financial planner $10,000 a year.

2)     This means that a financial planner will have to beat the market by at least 1% in order to justify the expense.

3)     This also means that financial planners don’t have an incentive to recommend index funds because that will ensure you lose to the market.  Instead, you’ll earn exactly what the markets dictate MINUS the financial planner fee of 1%.  (I HIGHLY recommend that you read this article, especially if you don’t know how losing 1% of earnings year after year affects your portfolio.)

4)     Financial planners therefore have an incentive to invest your money in actively managed funds to try to beat the market.  The result?  Again, READ or LISTEN to this excellent Freakonomics episode from 2017 called “The Stupidest Thing You Can Do With Your Money,” in which Kenneth French, professor of finance at Dartmouth discusses a study that concluded that only 2-3% of actively managed funds cover their cost.  That’s ON TOP of the 1% you might pay a financial planner to manage your portfolio.

Allow me to reiterate: if you allow a financial planner to manage your portfolio for 1% and invest in index funds, you automatically earn 1% less than the market.  If your financial planner invests in actively managed funds, you not only lost 1% to the market, but 98% of the funds you invest in won’t even cover their costs.  It’s a lose-lose situation. Here are a few more articles you might want to consider reading.

So what to do?  Well, I would suggest reading a lot, figuring out an asset allocation model that makes sense for you, and investing in four or five index funds that cover different asset categories.

But what if you really don’t know anything about finance and you find it terribly intimidating?  Heck, I remember working at a credit union for teachers back in the early 90s, and these were educated people who often had $50,000 in loans for things like boats, RVs, credit cards, etc. and who were only making $40,000 a year!  I get it.  Some people truly aren’t educated when it come to finance.  So what to do?  Well, again I suggest reading.  If you can read you can learn.  I highly recommend a book I purchased for my daughters called The Index Card. It’s an easy read.  It’s concise.  And it includes very specific rules you should follow.

In addition, there is another way to benefit from a financial planner without breaking the bank.

Even though I’m somewhat literate in finance (but only somewhat), I pay a financial planner a fixed fee every five years or so to review my portfolio, my tax strategies, my insurance, etc.  I couldn’t be happier with this arrangement.  Just last month I spent $500 to my planner – so only $100 a year – and in return he offered some suggestions about where to tweak my portfolio, adjustments I should consider making in insurance, and a few tax-savings strategies I might want to employ.  I’ll spend the next few months following up on his advice, and in five years I’ll pay him again to review my portfolio.  I can tell you that one simple tax strategy he suggested five years ago has saved me $1000 a year for the past five years and will continue to do so for the next two or three.  So for $500 I saved about $8000.  So I’m not saying financial planners don’t have something to offer.  They do.  I just don’t know if managing portfolios is one of them.

I’ve met several financial planners over the years.  Some nice, some absolute tools.  Some smart, some no smarter than you and me.  To me, it’s just too much of a crapshoot to trust someone enough to manage your portfolio and pay him/her 1% to do it.  It makes no sense to me.

For me, reading a lot and investing in index funds are the way to go.