Late Brokerage 1099 Forms & IRS Mailing Deadlines

I never file my tax returns too early. The last time I did so, I had to file an extra amended return as my stock brokerage sent me a late corrected 1099 form shortly afterward. What a hassle. It seems that every year one of these forms shows up in my mailbox in March. Indeed, TD Ameritrade just send me an e-mail today (2/25) that a corrected 1099 is on its way. Why?

IRS mailing deadlines
The official IRS mailing deadline for 1099-B forms (reporting sales from brokerage firms and mutual fund companies) is normally February 15th. This is 15 days later than the mailing deadline for most other tax forms like W-2s. However, this year February 15th falls on a Saturday and Presidents Day is Monday, February 17th. This results in the adjusted mailing deadline being Monday, February 18th, 2014.

So how can they arrive even later?
Many brokerage firms will only send a “preliminary” 1099 by this date to satisfy the IRS requirement. Because some securities (commonly certain REITs or foreign stocks) may not report their numbers to the broker in time, brokers often delay sending out their corrected or “final” 1099 until a month or more later. So while I start preparing my return ahead of time, I usually wait to file until I’m confident that all my 1099 forms are finalized.

In my case, it was the Vanguard REIT ETF (VNQ) that caused my corrected 1099 form.

Groupon: Whole Foods $10 Gift Card for $5

Groupon is selling a $10 Whole Foods Gift Card for $5 for one day only. They want to teach you about their search bar for some reason. No expiration date. Limit 1 per person, I’m sure it will sell thousands and thousands.

Remember that you can save a bit more on your Groupon with cashback shopping sites like eBates ($10 new customer bonus), Mr. Rebates ($5 bonus), and BigCrumbs.

Fidelity Investment Rewards American Express Card Review – 2% Flat Cash Back

fidoamexIf you’re looking for a solid cash back card and are willing to open a Fidelity account (or are an existing customer), then you should really consider the credit card offerings from Fidelity, especially the Fidelity Investment Rewards American Express Card.

This card earns a flat 2% cash back on purchases, as long as you deposit the money into an eligible account at Fidelity:

  • Fidelity Cash Management Account
  • Fidelity Brokerage account
  • Fidelity-managed 529 account
  • Fidelity Retirement account (IRA, Roth IRA, SEP-IRA, Rollover IRA)

Once your 2% rewards balance goes over $50, it will automatically deposit into your linked Fidelity account. I used to have my money go into a Fidelity 529; I think their investment options are okay but not the best, but this way you won’t spend your rewards on something frivolous. However, these days I just have it deposit into my brokerage account so I can invest it. An IRA would be too confusing for me due to the stringent IRS contribution limit rules. (If you’ve maxed out the limit, they say that they will automatically defer the rebate until the next year. But what if you have a partially phased-out limit due to income, and your limit is reduced to $2,350? How would they know that?)

In terms of catches, it’s mostly that you have to open an extra Fidelity account if you don’t have one already. It appears that the Fidelity Cash Management account has no opening minimum, but if you want to make some trades the Fidelity brokerage account you will need $2,500 to open that (no ongoing minimum balance requirement). I would open your Fidelity account first to make sure you have no issues.

Note also that the rewards only come in $50 increments:

Customers earn 2 points for each $1 in net retail purchases. Once you reach 5,000 points, they can be redeemed automatically or on demand for cash at a 1% exchange rate into an eligible Fidelity account (i.e. 5,000 points = $50 deposit).

So a $49 rewards balance = $0 in your pocket. It will roll over each month until the balance goes above $50, when the entire thing (i.e. $62.54) will arrive in your Fidelity account. Then the $50 hurdle kicks back in. So it is a little harder to time a cash out of your remaining balance if you wanted to close the account (but why would you?).

Finally, it is an AmEx and not a Visa/Mastercard, but I’ve found the number of merchants accepting American Express much improved since 10 years ago although there are still gaps in areas like utilities, insurance, and small mom & pop restaurants and stores.

But really, with no annual fee, this card and the Citi Double Cash card have raised the bar for a “basic” rewards card to 2% cash back at the very minimum. Outgoing Account Transfer Fee (Eliminated)

Updated to state that Betterment has updated their agreement to eliminate any outgoing ACAT transfer fee as of February 2014.

Original post:

Online portfolio managers are a hot area right now, and is one that promises “we do everything for you” simplicity combined with relatively low costs when compared with a human advisor. Recently, a reader named RSG left a comment:

In the updated user agreement, Betterment will charge a fee of up to $1000 for an in-kind transfer! That’s absurd and way higher than industry standard for other broker-dealers.

An in-kind transfer, also referred to as a full Automated Customer Account Transfer (ACAT) transfer, is where all of your holdings are transferred to another broker-dealer. Since you don’t sell any positions, any potential tax complications are avoided. I agree that this fee is around $75 at most brokers, so naturally I wanted to verify this claim.

I could not locate any notice of this fee anywhere on the website, even on their “pricing details” pages. The only place I could find it mentioned it is buried on page 59 of their 139-page customer agreement [pdf] last revised on 1/15/2014.

23. Transfer of Assets. Client may request transfer of Assets to an account Client has established with another broker-dealer. […] The fee provisions of the Brokerage Agreement and Advisory Agreement notwithstanding, Betterment Securities may charge a fee of up to $1000 for transferring assets to another broker-dealer.

I opened a $1,000 test account with Betterment myself and I admit that I totally missed this fee. I also verified this by contacting Betterment support staff, and here was their response:

Unfortunately this is not something that Betterment supports right now so we would bring in a third party to do an ACAT transfer. This process costs a fee of $1,000. Again, simply liquidating the funds is completely free.

Update: Immediately after this post brought up the issue, Betterment updated their agreement to eliminate any outgoing ACAT transfer fee as of February 2014.

Tax Guide for LendingClub and Prosper 1099 Forms

Updated. I’ve gotten a few tax-filing questions regarding P2P lenders Prosper Lending and Lending Club. For tax year 2013, LendingClub provided individual investors extra guidance with their Tax Guide for Retail Investors [pdf]. Using this information, I have updated this post.

Don’t file too early. My first recommendation is to not print out or download any of your 1099s until mid-March. Both Prosper and LendingClub seem to regularly issue corrected and/or amended 1099 forms with new numbers late in February. If you already printed them out earlier, go back and make sure they haven’t been changed. After having to file an amended return a few years ago, I always wait until after mid-March to gather all my tax documents.

Where to find your tax documents. I don’t think either Prosper or Lendingclub sends you 1099 forms in the mail. The easiest way for me to direct you to these documents is for you to cut-and-paste the following URLs into your web browser and then log into your accounts. Here are screenshots of what the pages should look like for Prosper and LendingClub.

Tax disclaimer. I am not a tax professional. The following is based on my best attempt at understanding the fuzzy world of P2P lending taxes. I am simply sharing how I’m going to do my personal tax return, but you should consult a tax professional for an expert opinion. You may not get all or most of these forms.


LendingClub 1099-OID. OID stands for original issue discount. The total of Box 1 is basically what LendingClub is reporting as the interest earned on your loans, net of fees. This interest should be reported on Schedule B and taxed as ordinary interest income (similar to interest from bank accounts).

LendingClub 1099-B (Recoveries for Charge-offs). If you had any loans charged-off*, but they still recovered some money later on, that will be reported here. It should be broken down into either short-term or long-term capital gains. Because it already tells me short-term or long-term, I will simply report the totals with acquisition and sell date(s) as “various”.

LendingClub 1099-B (Folio secondary market). If you sold any loans on the secondary Folio market, then the sales should be reported here. It should also be broken down into either short-term or long-term gains or losses. I will simply report the totals on Schedule D, using my acquisition and sell date(s) as “various”.

LendingClub 1099-MISC. I would just type this form into TurboTax box-by-box or submit directly to your accountant, usually under “Other Income”. Box 7 amounts will be subject to self-employment taxes, Box 3 amounts will not.

Prosper Lending

Prosper 1099-OID. Similar story to the LendingClub 1099-OID above, except they just give you the total from all your loans. Again, I have all zeros except for Box 1, which I will report as ordinary interest income on Schedule B.

Prosper 1099-B (Recoveries for Charge-offs). Again, anything listed here should be broken down into either short-term or long-term capital gains/losses and recorded on Schedule D. Prosper includes loan charge-offs on this form.

Prosper 1099-B (Folio secondary market). Again, anything listed here should also be broken down into either short-term or long-term gains or losses.

Prosper 1099-MISC. I would just type this form into TurboTax box-by-box or submit directly to your accountant, and it should be pretty straightforward. Box 7 amounts will be subject to self-employment taxes, Box 3 amounts will not.

*Reporting Charge-offs

If you have loans that were charged-off in 2013 (loan is very late and attempts to collect have failed, so they give up), you can write them off as a non-business bad debt. You can find these in either your year-end statements (LendingClub) or your 1099-B form (Prosper). These are all treated as short-term capital losses, which you can use to offset short-term capital gains from other investments or you can deduct against up to $3,000 in ordinary income per year (with the balance carrying forward to the next year).

More resources: Let me also recommend Peter Renton’s post at LendAcademy, the follow-up comments on that post, and this forum post by AmCap as good references for an intelligent discussion on the topic. Also see the LendingClub and Prosper tax pages, even though they aren’t especially helpful.

Tax Prep Guide 2013: TurboTax vs. TaxACT vs. H&R Block Online

According to an informal 2012 poll, 86% of blog readers prepared their own taxes using software with a breakdown of 60% TurboTax, 21% TaxACT, and 16% H&R Block at Home. This nearly matches the findings of analytics firm Comscore, which found that of online filers 60% used TurboTax, 18% used TaxACT, and 15% used H&R Block at Home.

I’ve used all three programs over the years and each has their clear strengths and weaknesses. The NY Times recently did their own 3-way comparison with very similar experiences to my own. They actually called in for help and reported the results, so I’ve added this factor into my lightning review:

The major differentiating factors are price, time-saving features, audit support, and ability to answer specific tax questions. In terms of accuracy, I think all three are nearly identical. All three offer a “Maximum Refund Guarantee” (relative to competing software) as well as an “Accuracy Guarantee” (relative to your tax liability) that says that they will pay any penalty and interest assessed by the IRS or your state due to calculation errors on their part (though H&R Block limits this to $10,000). Actual cost can vary widely with sales and discounts, listed here are just the everyday prices.

TurboTax Onlinett180

  • Most expensive. Federal Deluxe regular price is $29.99 w/ e-file. However, you now need Premier at $49.99 if you have an investment gains or losses. State return price is $36.99.
  • Best import support from payroll providers and financial institutions for automatic import of W-2 and 1099 forms. Works with free “ItsDeductible” program to help with recording charitable donations.
  • Moderate audit support (you get help, but no in-person representation)
  • Specific tax advice – Free online chat included. Did not provide definitive answer to NYT reporter’s question.

Bottom line: The time-saving choice if you have a lot of brokerage transactions, W-2s, or other 1099 forms to electronically import this year. Also if you have a lot of details to import from last year’s return with TurboTax. It may be worth the extra cost to avoid tedious data entry.

ta200TaxACT Online

  • Cheapest overall with Federal Deluxe regular price at $12.99 w/ e-file. Federal + State return combined including e-file at $17.99.
  • Limited import support (worst of the three).
  • Limited audit support (worst of the three).
  • Specific tax advice – Phone support only, online chat not available. Did not provide definitive answer to NYT reporter’s question.

Bottom line: The value choice if you just want accurate DIY tax return software and don’t need any extra assistance.

hr160H&R Block at Home Online

  • Middle-of-road pricing. Federal Deluxe regular price is $29.99, but includes investments. State return price is $36.99.
  • Moderate import support for 1099s and W-2 (not as broad at TurboTax, better than TaxACT)
  • Best free audit support. Only product that includes an H&R Block Enrolled Agent actually attending your audit in-person. However, consider whether you would hire your own representative in the actual event of an IRS audit.
  • Specific tax advice – Free online chat included, only one to provide definitive answer to NYT reporter’s question.

Bottom line: The got-your-back choice if you want the assurance that a federally-authorized enrolled agent will guide you for free through a potential albeit unlikely audit. Anecdotally the one most likely to provide answers if you have harder tax questions.

Prosper vs. LendingClub Investor Experiment: 15.5 Month Update

After posting the 1-year update (Part 1, Part 2) of my Beat-The-Market experiment back on November, I got bored. I had started with $10,000 split evenly between Prosper Lending and Lending Club, but although this alternative asset class had potential, I just didn’t find it reliable enough for me to invest significant funds in it.

I didn’t sell off my existing loans, but I stopped reinvesting in new ones. I hadn’t logged into either account for months, but this week I wanted to download my tax documents. So, I figured another update was in order, 3.5 months later.

$5,000 LendingClub Portfolio. As of February 19th, 2014, the LendingClub portfolio had 199 current and active loans, 36 loans that were paid off early, and none in funding. 6 loans are between 1-30 days late. 8 loans are between 31-120 days late, which I will assume to be unrecoverable. 7 loans have been charged off ($152 in principal). $1,814 in uninvested cash. Total adjusted balance is $5,305. This is only $1 higher than 3.5 months ago.


$5,000 Prosper Portfolio. My Prosper portfolio now has 185 current and active loans, 56 loans that were paid off early or payoff in progress, and none in funding. 4 loans are between 1-30 days late. 10 are over 30 days late, which to be conservative I am also going to write off completely (~$183 in remaining principal). 14 have been charged-off ($302 in principal). $1,619 in uninvested cash. Total adjusted balance is $5,255. This is $45 less than 3.5 months ago.


What has happened since my last check-in on November 1st?

  1. My total adjusted balance is $10,560, which is a $44 drop over the last 3.5 months. Even with the increase in idle cash, my total balances should still be inching up, not down. It appears that an increasing number of late and defaulting loans are starting to catch up to me.
  2. My idle cash balance across both accounts has increased by $1,527 in just 3.5 months, indicating an increasing number of early loan payoffs and thus fewer people paying me 10% interest rates.
  3. Prosper is currently doing worse relatively than LendingClub. This could change again in the future. Here’s an updated chart tracking the LendingClub and Prosper adjusted balances over these past 15.5 months:

I suppose that I’ll hang onto these loans and see how the rest unfolds. I know that other people report 10%+ annual returns on Prosper and Lending Club and may be better loan pickers than me, but I still be wary setting such high expectations for the average P2P investor. I’m still in the black and doing okay, but I wouldn’t count your chickens until the loans get a bit more mature.

Can I Really Withdraw My Roth IRA Contributions At Any Time Without Tax Or Penalty?

Revised for 2014. This post about how to withdraw past Roth IRA contributions has been popular over the years amongst search visitors, and I have completely updated it using the most recent IRS documentation. Besides emergencies, this information may also be useful for early retirees under age 59.5 that wish to access some of their tax-deferred funds without incurring taxes or penalties.

This is a follow-up to my post Roth IRA Contribution vs. Emergency Fund Savings, where I suggested that people should just fund their Roth IRAs first over an Emergency Fund. The simple reasoning was that anyone can withdraw their Roth IRA contributions at any time, without penalty. (Not earnings, just contributions.) Put in $5,000, and you can take out $5,000 later – be it one day later, one week later, or one decade later. But some concerns were raised about the validity of that assumption, so I wanted to iron that out here using IRS Publication 590.

First, we head to the Roth IRA section, specifically the subsection called Are Distributions Taxable?. Here, the first sentence states:

You do not include in your gross income qualified distributions or distributions that are a return of your regular contributions from your Roth IRA(s)

Sounds pretty clear, but let’s keep looking. The next section talks about qualified distributions, like those made after you turn 59½, which are definitely not taxable. We are given this decision flowchart (Figure 2-1), and… whoops, we may not even pass the first box. Taking out your contribution within the first 5 years is not a qualified withdrawal. 

But wait. Not all unqualified withdrawals are taxable. Going to How Do You Figure the Taxable Part?, we are directed as follows:

To figure the taxable part of a distribution that is not a qualified distribution, complete Form 8606, Part III.

Here is a link to Form 8606 [pdf] and the Form 8606 instructions [pdf].

Here’s how you would fill out the form for the simple situation of taking out former Roth IRA contributions. On Part III, Line 19, you would include the money you took out as a distribution – “Enter your total nonqualified distributions from Roth IRAs in 2013”. This would carry over to line 21. But then on Line 22 you would “Enter your basis in Roth IRA contributions”. Line 23 tells you to subtract the difference (21 minus 22). If you are taking out less than you formerly contributed over the years, your net taxable amount would be zero.

What about a possible 10% penalty? In the section on the penalties Additional Tax on Early Distributions, we see this:

Unless one of the exceptions listed below applies, you must pay the 10% additional tax on the taxable part of any distributions that are not qualified distributions.

Since this unqualified distribution of a former contribution is not taxable, there is no “taxable part” and thus no penalty to worry about.

In conclusion, although taking out a former Roth IRA contribution as a distribution may be (1) an unqualified distribution, it is also (2) not taxable and (3) not subject to any additional penalties. When subsequently filing your taxes, remember to fill out IRS Form 8606 as indicated above so show the IRS that you are only taking out your original basis.

How Do I Make A Withdrawal?
If you are under 59½, you usually need to make a specific request to your broker. Here is the info from my Vanguard account:

You can request a withdrawal from your IRA online, over the phone, or by mail. You can have a check sent to you, have the proceeds deposited directly to your bank account, or transferred to a nonretirement Vanguard account.

OptionsHouse Free iPad Mini Promotion

Online stock brokerage firm OptionsHouse has a promotion where new customers* can get a free iPad Mini (16gb WiFi model w/ Retina display, $399 value) if you satisfy the following requirements:

  • $10,000 minimum funding required
  • Must fund within 30 days of completing application
  • Must make 30 commissionable trades ($4.75 each)
  • Must complete those 30 trades within 90 days of account funding
  • IRA accounts are not eligible
  • Must not withdraw to below minimum funding level for 180 days (market fluctuations okay).

*You cannot have a current Optionshouse account or maintained an account with them during the last 30 days.

30 trades times $4.75 a trade is $142.50 in commissions. iPad Mini with Retina 16GB is $399 at Apple store and even $399+ on Amazon. According to the terms, retail values under $600 will not be including on your 1099 form. Seems like a good promo for a new iPad, especially if you’re looking to try out a new brokerage firm and need to make a number of trades anyway to establish your positions.

Get a free iPad Mini at OptionsHouse

Groupon $10 off $40 Code – Presidents Day Weekend

Presidents Day Weekend Special. Get $10 off a Groupon of $40 or more (Local deals only) with promo code 10OFF40LOCAL. Valid 2/15 through 2/17 at 11:59pm PST.

LivingSocial 20% Off Code – Presidents Day Weekend

Presidents Day Weekend Special. Get 20% off at with promo code 2014PRESDAY. Valid 2/15 through 2/17 at 11:59pm PST. Good for purchases of any amount, but maximum discount is $20. Savings will be reflected on the final purchase confirmation page.

Square Cash: Send/Request Money Via Debit Card For Free + $1 Carrot

square1Square, known for helping people accept credit cards with smartphones, has expanded another feature called Square Cash. Yes, it’s yet another attempt at simplifying person-to-person payments, but this time all you need is e-mail and a debit card number. No accounts to open, no passwords to remember, and no fees either.

To request money, just send an e-mail with the following fields:

To: [one or more email addresses]
Subject: You can write whatever but include $ [amount]

To send money, just send an e-mail with the following fields:

To: [one or more email addresses]
Subject: $ [amount]

That’s it, the Square website walks people through the rest. I found it pretty interesting that you can both deposit and withdraw money via debit card. If this stays fee-free then I could actually see myself using this between friends and family. iPhone/Android app also available, but not necessary (it just helps you compose the e-mail).

Right now, Square Cash will give you $1 to try it out. Your debit card number will then be associated with the e-mail address you provided from then on for future payments (unless you change it).