Taxes and Investing

Tax-Loss Harvesting is Killing Your Nest Egg

Sophisticated investors have been harvesting losses manually for decades to acquire tax benefits. Betterment and Wealthfront made harvesting losses easier and more efficient than ever since 2008. Betterment alone has reached $5 billion under management.

Personal finance bloggers tend to love tax-loss harvesting without much mention of risk. A few bloggers have expressed doubts over the whole process, but their numbers are few and their voices drown out by the scream of the crowd. Betterment’s affiliate program has caused concern positive reviews are biased. Betterment’s affiliate program has tightened for bloggers investing with the company and with published reviews due to recent SEC rule changes. As a result, many bloggers must end their affiliate relationship with Betterment or take down their reviews of the company.

The truth about TLH is not as clean cut as some would have you believe. Taxes and performance are two issues every investor needs to consider prior to investing with any company engaged in TLH.

How TLH Works

Tax-loss harvesting is when you sell a security at a loss for tax purposes. The IRS knows this strategy can be used to generate substantial phantom tax losses by taxpayers. There are rules to prevent doing just that.

Sales of a security at a loss are not deductible if you buy a substantially identical stock/security within 30 days of the sale. This includes the purchase of options to purchase a substantially identical security. Disallowed loses from a wash sale are added to the basis of the purchased substantially identical security.

Wash sales in a traditional IRA are lost forever! Using Betterment or other similar programs increase the risk you will have a wash sale. When Betterment sells a security at a loss and you buy a substantially identical security in your IRA unwittingly, the wash sale loss is disallowed forever. The taxpayer’s basis in the IRA is not increased by the amount of the disallowed loss. Understand now? No? Then you either must allow Betterment to handle all your investments or don’t use them at all. It is the only way to steer clear of this pitfall.

Continue reading

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Early Retirement, Lifestyle

The Right Way to Own Investment Properties




During the 1980s and 90s I owned a lot of real estate. It started slow and exploded into a 176 building pain in the ass. To be fair, most of the investment properties we owned were either single family homes or duplexes. A few multi-family buildings, a boarding house and a storage facility rounded out the mix.

With so many properties running through my personal accounts and a partnership with dad and brother, I learned a few things along the way. One hundred seventy six buildings is a lot of buildings. Good thing I didn’t own all of them at the same time. Mistakes were sure to happen.

By the early 2000s the real estate empire was gone. I was burnt out and sick of working with tenants. Countless property managers helped us over the years, but it was not enough. Managing over a hundred units much of the time over a footprint covering most of NE Wisconsin took its toll. To complicate matters, I also ran my accounting practice with double the employees I have today (during tax season).

Starting slow was my greatest idea. It felt good to see the passive income filling the checkbook. Our teams of contractors allowed us to buy fixer-uppers and increase the property values significantly. Our best deal was the purchase of an upper-lower duplex in my hometown for $8,000. Hard not to make a profit on those.Continue reading

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Early Retirement, Taxes and Investing

Tax-Advantaged versus Regular Accounts

 

Nick H recently emailed me a question about how much money he should invest in tax-advantaged accounts before adding to non-qualified accounts. Due to the large number of emails I receive I am unable to provide individualized tax advice unless you are a client. Nick’s question had a familiar ring. Several times per week I get a variation of the same question. Rather than ignore the request, I decided to put it into a post so all readers can benefit from my suggestions.

Here is Nick’s complete email:

Dear Wealth Accountant,

I have been a reader of yours for a few months now, and enjoy it very much.  I was introduced to your site via a MMM post.

I have a question for you regarding investing in tax-advantaged accounts vs. normal accounts. Standard advice is that I should max out tax advantaged accounts before saving in normal accounts.  However, with financial independence/early retirement in mind, if I do not make enough to max out tax advantaged accounts and save enough in a normal account for early retirement, I think that it makes more sense to put just enough into a 401k to get my match, then save everything else I can in a normal investment account.

I reach this conclusion because the goal of early retirement is to build up an income stream, unlike standard retirement in which you just achieve the largest possible pile of cash.  Since there are significant limitations on access to the funds in taxed advantaged accounts, this seems like an inefficient method of saving.  Again, assuming that I have to choose between the two.

Thanks
-Nick H

PS. I also posed this question to MMM.  I am very curious to get both of your perspectives on it.  Thanks & hope to hear from you!

Nick makes a narrow assumption of either/or. He indicates he either has to max out his retirement accounts before funding non-qualified accounts or he will not have an income stream to fund his early retirement.

Nick also turns the tables on the standard advice by saying standard advice says to max out retirement accounts. I guess it depends on whose standard advice we are looking at. Most standard advice is geared toward generating larger fees for the investment house. Standard advice says you should save 10% of your income. It makes me nauseous thinking about it.Continue reading

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Lifestyle

Watch the News Right or Turn it Off




News over the years has deteriorated into biased reporting, slanted by political opinion. Finding quality news to form your own opinion is nearly impossible to find. Yet, without good information you can’t make informed decisions in your investing, business or personal life.

As bad as it is, there are ways to still get quality news reports. It requires effort to sift through the garbage to find facts you can use to improve your business and personal life. The BBC, The Economist, and National Public Radio still provide solid reporting with a minimal of political bias. Fox News is not news, except for those rare occasions when they report an event they have not had time to work a political angle on yet. CNN is somewhat better, but still contains plenty of bias.

Before you blame to broadcasters and the internet news feeds, remember, we are the ones feeding the beast. By consuming meaningless opinion pieces we encourage more of the same production. Our own personal biases will determine if we love Fox News or hate it. I don’t care for Fox News for a completely different reason I will share shortly.

Polarization and populism has taken over. People only want to hear what they want to hear. News no longer informs with facts; it reinforces already existing personal biases. It caters to base emotions like anger and hate. And let’s not pick on Fox News alone. I don’t watch TV so unless I am visiting family or in an airport, I don’t get much TV news indoctrination. I prefer internet news feeds. CNBC provides business news, The Economist provides a wide variety of news from around the world, and gasp, I also tend to sift through the dung pile of Yahoo’s news feed.Continue reading

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Taxes and Investing

Prepare Your Own Taxes the Right Way

It’s that time of year again where we need to reconcile the previous year’s income for the government. The task can be daunting, but with armies of tax professionals and online software, many people can tackle their tax return with few issues.

The trick is finding the right tax software when you plan on preparing your own tax return. The most popular online packages are dummied down versions of better tax software programs. The Q&A required by most online programs can become daunting (and time consuming) if you have any tax knowledge at all. The biggest problem is finding tax software that is professional grade that offers just enough help to not be invasive.

I want to introduce you to an online tax program I think is superior to other online software: Drake Software. The banner below is a direct link to the software for individual users. It was featured last year on Mr. Money Mustache. It also happens to be the same tax software I use in my office.

Over 50,000 tax professionals use Drake software to file over 26 million tax returns.  My office was one of the earliest adopters of the Drake interface (one of the first 200 if my ID number is any indication).

Back in the late 1980s I sought out a professional software package that was not only robust, but offered economical e-filing. Back in those days it was common for software to charge $35 or more just to e-file. Drake was an industry leader, charging only $1 per e-filed return. My office could offer free e-filing before anyone else due to Drake and their powerful software platform.

Time has only made this software better. Of course, my office still e-files for free, but it is so much more. Drake branched out into other areas of the accounting office. They also offered accounting firms like mine an opportunity to provide an alternative in the DIY tax preparation segment.

What I liked from the start was that Drake incorporated the entire professional grade platform in their online version for people preparing their own return. No other online software offers such a robust program to the general public, in my opinion. They market the program under the 1040.com name.Continue reading

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Early Retirement, Estate Planning, Lifestyle

Avoiding the Gold Diggers

Community Property States

At a recent Camp Mustache where I gave a presentation I also offered one-hour personalized consultations. Most of the advice I give is identical among all people I consult with. Most themes come up again and again. About 20% of what I advise is unique to the individual.

This particular group was comprised of high net worth people. These people save a massive percentage of their annual income and are in a position to retire early; mid-30s is average. Incomes were all over the map. Some had high income; some had modest income. All invested heavily in index funds and/or real estate.

An attractive young woman was next in line for a consultation. She had amassed a reasonable amount of liquid funds and was planning her retirement strategy. I knew she wasn’t married by looking at her tax return. I asked if she had a special someone in her life. She said no. I then made the offhand comment, “If you ever decide to get married you will have a prenup.”

Prenuptial agreements are common so I felt the comment was just a reminder. She seemed surprised so I reiterated she will need a prenup if she gets married, especially since she has a sizable nest egg. She wasn’t so certain it was a good idea. I reminded her gold diggers don’t always have tits. It took a bit of convincing to get her to come around to my way of thinking. I told her if I ever found out she got married without a prenup I would be very unhappy with her. My final selling point was, “When you have money some people will lie to get you to marry them. Then when they screw around and leave, you will pay them half your net worth to screw another woman. It is a bitter pill you want to avoid.”Continue reading

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Early Retirement, Frugal Living, Lifestyle

Kill the Economy and You Will Not Even Notice

It does not take long when you wander the blogs of the ‘retire early’ community before you hear the common refrain: If everybody did this stuff it would kill the economy. To which I promptly call bullshit.

Bill Gates and Warren Buffett managed to not spend over $100 billion of their money over the last few decades and the economy has done fine. In the 1950s the savings rate was much higher and the economy more vibrant. When the research is reviewed there is no doubt excessive debt, a low savings rate and excessive spending have more to do with an anemic economy than any responsible spending will do.

People look for any excuse they can to remain married to their poor habits and lack of self-control. It is easier to complain about successful people than it is to take responsibility for your own actions. Somehow these people have been bullshitted for so long they actually think poverty is the only way to keep the economy going. Really? They think the only way to survive is to spend every nickel they have. They think living on the financial edge of ruin from the first light breeze is what makes the economy purr and provides job security. Where does this nonsense come from?Continue reading

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Early Retirement, Lifestyle

Recap of Camp Mustache SE

Working as a team to climb any wall in our way.

Each edition of Camp Mustache gets better than the one before. Camp Mustache SE in Gainesville, Florida (January 13 –January 16, 2017) is the fourth in a series of camps, this being the first outside the Seattle area. I have had the honor of attending and speaking at all but the first Camp Mustache.

Stephen Baughier organized the event with guidance, advice and a helping hand from Emma Pattee. Emma’s experience organizing Camp Mustache in Seattle allowed Stephen to move up the learning curve faster. The added experience and hard work made Camp Mustache SE awesome on every level. For the record, I have already accepted the offer to attend Camp Mustache IV in Seattle over Memorial Day weekend in the states this May. There is no doubt the gathering will be an incredible place to learn and meet like-minded people in the FIRE community.

Several notable names were in attendance. Pete, the guest of honor, was, of course, there. J.D. Roth (Money Boss), Joshua Sheats (Radical Personal Finance), Brad Barrett (Travel Miles 101), Gwen (Fiery Millennials), Jonathon Mendonsa (Chosefi), Zeona McIntyre (ZeonaMcIntyre.com), Brooks Nelson (Gainesville Cohousing) and more were available for questions. (Hope I did not miss anyone.) Continue reading

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