Get ready to save!

Keep up to date with the latest insights on tax planning for your equity, small business, crypto, real estate, and more.

Startup Employees: Defer Taxes On Secondaries With A Charitable Remainder Trust

✅ An early startup employee planning for a $500,000 secondary sale could earn an extra $218,000 over a 20-year trust term if he put his shares into a Charitable Remainder Trust.

In our previous article in the series, we shared a story about Annie, an engineer at Coinbase, who set up a charitable remainder trust to minimize her tax hit when she sells her shares after the company’s IPO. Today, we’ll learn about Barney, who joined a startup that’s been growing like crazy since it started a few years ago. Barney expects there will be a Series B round in the next few months, and he hopes to sell some of his shares shortly after that for a gain of $500,000. (Before you read about how a Charitable Remainder Trust can help Barney with his tax bill, feel free to take a moment to review the foundational posts in our series on CRTs: Our primer on the basics, why CRTs are more flexible than you think, and our first example, which focused on an employee planning for a massive IPO.)

Barney, an early employee, is planning for secondary sale

Our next example, and one we see very frequently, is Barney, who lives in Brooklyn and joined his company in 2018. The company has done very well—it’s a B2B2C future-of-work play, and (silver lining!) the work-from-home boom of the last 18 months has sped things up considerably. Barney is looking to take some money off the table—just to hedge his bets—but he doesn’t want to take the massive tax hit that will accompany the $500,000 sale.

Recapping the numbers

Cost basis: $5,000

Current/sale value: $500,000

Chosen trust: 20-Year Term NIMCRUT (Read about the tradeoffs between lifetime and term trusts here)

Immediate Charitable Deduction

Like all of our users who choose a Charitable Remainder Trust, Barney will get an immediate tax deduction. Consistent with the IRS’s rules, he’ll get to deduct about 10% of the current value of the shares he puts into the trust, or about $50,000. Since Barney lives in New York City, which is a high-tax city in a high-tax state, the tax savings are substantial: That $50,000 deduction translates into cash savings of about $19,000 on next year’s taxes.

No Taxes On Sale

That’s $19,000 extra in Barney’s pocket before things even really get going. Next, of course, Barney gets to defer the state and federal taxes he would otherwise have owed on the shares he’s selling. That’s about $160,000 in taxes deferred to a later date.

Available Withdrawals + Creative Solutions

Like Annie, the Coinbase employee, Barney is a little bit concerned about his money being stuck in a trust for the long term. After all, this is his first big liquidity event, and he doesn’t yet have a big nest egg for retirement (whenever that is).

Fortunately for Barney, he has several options for creating liquidity. First, there’s the easy liquidity he can get out of a NIMCRUT: 11% per year if he chooses a Term trust, or $260,000—over half of the initial funding value—after just 6 years. What’s more, Barney has other tools at his disposal. One that our users have found especially easy to utilize is a simple line of credit: Although Barney can’t borrow against the value of his CRT, since that value belongs to both him and his chosen charity, he can open a line of credit using the future income from his CRT as collateral. What this means in practice is that Barney can access as much as the full value of his expected payouts from the trust at a reasonable interest rate, should he need more than the liquidity he would normally be able to take out of his trust.

Total Returns

Despite his general thinking on liquidity, Barney is a young guy, and he doesn’t need much right now, so he’s happy to leave most of his money in his trust to grow for the full 20-year term. Let’s suppose his only withdrawals are $125,000 in year 3 (to take a year or two off, say), $175,000 in year 9 (down payment), and $225,000 in year 15 (fun money).

How much would Barney have at the end of the trust term? After those 20 years, if Barney has her money in a Charitable Remainder Trust, he’ll end up with about $1,380,000 in total payouts. About $475,000 of that will go to the charity of his choice, so he ends up with about $910,000 in his pocket. (For reference, the numbers for a Term Standard CRUT are lower: He’d end up with about $570,000 in his pocket at the end.)

If, instead, Barney had kept his money in a regular, taxable investment account, he would have instead ended up with about $690,000.

In other words, even after his charitable donation, Barney still pockets an extra $218,000 on his initial $500,000 secondary sale.

Overview of how a Charitable Remainder Trust works

Next up

About Valur

We built a platform to give everyone access to the tax and wealth building tools of the ultra-rich like Mark Zuckerberg and Phil Knight. We make it simple and seamless for our customers to take advantage of these hard to access tax advantaged structures so you can build your wealth more efficiently at less than half the cost of competitors. From picking the best strategy to taking care of all the setup and ongoing overhead, we make it easy and have helped create more than $500m in wealth for our customers. Schedule a time to chat with our team and learn more about how we can help you!