This 401(k) Rollover Gambit Could Save You a Bundle in Taxes

In some ways, leaving a job is pretty clear cut. You stop working for them, they stop paying you: the end. But the relationship between you and your ex-employer may not be completely severed so easily -- especially if you've been participating in a 401(k) plan. Many people choose to just leave those funds invested where they are. Another option is to roll those funds over into a new account -- usually an IRA, or your new company's 401(k) plan.

But there's a less-known option you may just want to use, especially if your portfolio includes a hefty chunk of stock in your employer, and that stock has done particularly well. By taking advantage of net unrealized appreciation, you can keep that stock and reduce your tax bill down the road. In this segment from Motley Fool Answers' July mailbag show, hosts Alison Southwick and Robert Brokamp -- along with special guest Ross Anderson, a certified financial planner at Motley Fool Wealth Management -- explain how it works.

To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. A full transcript follows the video.

This video was recorded on July 30, 2019.

Alison Southwick: Last question is from Elton. "I have a question about something you discussed on your May 28th episode." You remember that, right, Ross? "That there is an exception regarding moving employer stock into an IRA. Can you tell us more about that? This is the first time I've heard of it and if true, it sounds like it could be a way to reap some tax benefit by not having to sell appreciated stock."

Ross Anderson: My first question -- just going back to that actual episode -- was that a discussion about net unrealized appreciation, because that's what it sounds like the question is related to.

Robert Brokamp: Yes! [Whispers] I don't remember exactly.

Anderson: I'm going to assume that's what the question is about, Elton, because I think you're dancing around that. So net unrealized appreciation is essentially a strategy -- if you've got employer stock in your 401(k) -- to move that employer stock out as part of a rollover, but you'd deal with it differently in terms of your taxation. For the purposes of the discussion, let's pretend that all of the money is pre-tax. Let's ignore Roth 401(k) entirely.

If you've got a stock in there, let's say over the years you've put $50,000 into that stock and it's now worth $250,000 of value inside your 401(k). If you roll all of that money into an IRA, it's going to move over. There's no taxes as part of that, but what does happen is they liquidate everything. They take you to cash, they send you a check and you put that check in your IRA.

At some point, when you start taking withdrawals, either because you need the money or because there's a required minimum distribution, all of that money that comes out is going to be taxable as income to you.

NUA is a little bit different. At the point of the rollover, if you said, "Hey, listen, I want to take my company stock for XY&Z. I'm going to pay ordinary income taxes on the $50,000 of basis and then I'm going to move that entire piece of stock into a brokerage account." It's like you bought the stock for $50,000 and just held onto it. So it's still worth $250,000 and the $200,000 of unrealized gains are ultimately going to be treated as long-term capital gains.

So the difference, there, is you're going to accelerate some income in the year that you do this, because you do have to pay taxes on the basis when you do it, and then you're ultimately going to treat that stock as a long-term holding in a brokerage account. So you're not moving the stock to an IRA. You're moving it to a taxable brokerage account or just an ordinary brokerage account, but if you have highly appreciated employer stock in your 401(k) plan, this is a pretty powerful strategy that could potentially save you a lot in taxes, because paying income taxes on $250,000 is very different than paying income taxes on $50,000 and capital gains on the other $200,000.

So I think what's what you're talking about. If you've got highly appreciated employer stock, that's a huge opportunity. Make sure you don't roll over that 401(k) without talking to somebody or going through it with a financial professional to see if that makes sense for you, because I think that's a big deal and once you lose the opportunity there's no going back.

Brokamp: I would second that, too, because not every company stock plan is the same. There are different versions of it, different rules, and you definitely want to talk to an expert before you make a major decision about such a big chunk of change.