Inside America’s Race to Hide the World’s Money
Reveal
The Center for Investigative Reporting and PRX
4.7 • 218 Ratings
🗓️ 11 April 2026
⏱️ 51 minutes
🧾️ Download transcript
Summary
Alessandro Chesser is a 40-year-old Silicon Valley entrepreneur. He’s married with two kids and was the first in his family to attend college. His grandfather immigrated from Sicily and worked as a school janitor so his family could have a better life.
Skip forward a few generations, and Chesser is noticing the way wealthy investors hide their money to avoid paying taxes. He’s outraged and wants to upend the tax system, which he thinks is unfair to the everyday American worker. In Chesser’s mind, the realistic solution isn’t to reform the tax code, but to make it easier for average Americans to access one of the best-kept secrets of the superrich: trusts.
Trusts have become big business in the US. They are now an industry worth trillions of dollars. But no one knows the exact number, because the trust industry is extraordinarily private. Trusts can last forever (literally), but there is no public registry for them. In fact, they are one of the main reasons why watchdog groups consider America to be the most secretive financial jurisdiction in the world.
This week on Reveal, journalists Sally Herships and Leah McGrath Goodman investigate America’s shadowland of trusts. As the nation’s wealth gap keeps growing—and Americans brace for Tax Day—we uncover what’s at stake as US states race to become the most trust-friendly jurisdictions in the world.
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Transcript
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| 0:00.0 | From the Center for Investigative Reporting in PRX, this is Reveal. I'm Al Letson. |
| 0:06.6 | In a lot of ways, Alessandro Chesser is your typical entrepreneur. And even though he grew up in Silicon Valley, he did not grow up privileged. |
| 0:15.6 | Not at all. Not even close. Alessandro is 40. He's married, has two kids, lives just outside of San Francisco, and was the first one in his family to go to college. |
| 0:26.3 | My grandfather came his country with, you know, not a dollar to his name. I mean, he worked as a janitor for elementary schools and movie. He worked all around the clock. |
| 0:36.7 | But fast forward a couple generations, and Alessandro is trying to make it big. |
| 0:41.1 | He gets a job in Silicon Valley at a company called Carter. |
| 0:44.8 | It helps startups keep track of who owns stock in their companies, from employees to founders |
| 0:50.5 | to investors. |
| 0:52.5 | As vice president of sales, Alessandro is spending a lot of time with clients, and he starts |
| 0:58.2 | to notice a pattern in the way wealthy investors are handling their shares. |
| 1:02.4 | Which was the most successful startup founders and investors didn't just hold their shares in their name personally, they would move their shares into trusts. |
| 1:17.0 | Trusts are a way to hold on to money and assets, almost anything from a vacation house to a racehorse to shares of stock. |
| 1:25.5 | Sometimes a founder would have 10 or 12 trusts for different family members that they would put |
| 1:32.4 | their shares into. |
| 1:33.6 | I thought they were just being generous. |
| 1:35.6 | But that wasn't it. |
| 1:36.7 | We did some research and we learned that they did it because they were getting tax benefits. |
| 1:42.8 | Which means that each trust can sell up to $10 million and pay zero taxes. |
| 1:49.4 | That limit has gone up to $15 million. |
| 1:52.7 | And all of it leaves Alessandro wondering, why doesn't everybody do this? |
| 1:57.2 | We looked into it and we saw that, you know, it costs on average over $100,000 just to set it up. |
| 2:04.8 | And so the fees are enormous and it really results in only the most successful and richest |
... |
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