How to avoid Paying capital gains taxes

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In this episode, Adam Nash explains how to pay lower taxes on stocks and avoid what is called the 'wash rule.' Since 2017, Adam Nash has taught “Personal Finance for Engineers” at Stanford. He's covered topics from compensation, investing, to real estate. He’s the Former President and CEO of Wealthfront, Former Vice President of Product & Growth of Dropbox, and on the Board of Directors at Acorns. He’s currently the CEO and co-founder of Daffy, a not-for-profit community built around a new, modern platform for giving.

Well, Halloween is around the corner and this year has been a very scary one for both the stock market and for the crypto markets.

And so quite a few investors are sitting on positions that have a loss on them.

That never feels good.

And as a result, people are looking at taxes this year and asking a lot of questions about when it makes sense to sell stock in crypto and when it makes sense to donate that.

Fortunately, there's a silver lining when it comes to your taxes, which is that if you sell securities at a loss, you do get to count that loss against other gains or income when you're filing your taxes.

So basically you can save money on taxes in many situations by selling some securities for a loss before the end of the year.

And while that sounds like a good deal, there's a problem and that problem is what's called the wash sale rule.

The IRS will let you deduct that loss, but only on the condition that you don't buy back that same security within 30 days.

And that may not seem like much of a limitation, but a lot of people are very nervous about stocks in crypto that they believe in that if they sell the stock or crypto position and then it goes up the next week, they'll have missed out on the gain.

Now it turns out there's no exception to this rule, but there are ways to manage the risk.

You could, for example, if you sold Apple stock at a loss by another security like Google, but that's not perfect because Apple and Google are not really the same company.

They don't have the same business and there is a possibility they won't perform the same way.

Holders of index funds actually have an easier time because if you sell the Vanguard emerging markets fund, you can always buy the Schwab emerging markets fund and get substantially the same performance, even though they're different securities and they follow different indices.

So if you're looking at a little bit of tax tuning at the end of the year and you've taken some gains on some positions earlier this year, it's worth looking around for positions that you're willing to sell and be without for 30 days to help keep your tax bill low this year.

Well, I have good news for you.

You can donate appreciated stock or crypto to charity, take a full charitable deduction for the value of that stock in crypto, and you never have to pay capital gains taxes on the appreciation.

Let's say you were choosing between donating $10,000 worth of cash or $10,000 worth of stock, but it's a stock you believe in and will be worth $20,000 in the future.

It's okay.

You can actually have your cake and eat it too.

Donate the $10,000 worth of stock and then use the $10,000 worth of cash to buy the stock back.

Why can you do this? Because there is no wash sale when it comes to donations.

When you sell a normal stock or security, you have to wait 30 days before you can buy it back again.

Otherwise, the IRS will disallow the deduction from that loss.

But when you donate stock, there is no such limitation.

So you can donate your favorite stock or crypto, take advantage of that charitable deduction, never pay capital gains on that position, and you can keep your portfolio set up for growth in the future.

It's really a rare case when you get a deal this good.

But if you are thinking about making a big donation this year, consider donating appreciated stock or crypto to your donor fund at Daffy.

Please note that the information contained on this page is for educational purposes only and should not be considered tax advice. Any calculations are intended to be illustrative and do not reflect all of the potential complexities of individual tax returns. To assess your specific tax situation, please consult with a tax professional.

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