How This 'Tax Exile' Embraced AI And Became A Billionaire

Forbes

23-06-2025

'T here's an old story about the Rolling Stones being tax exiled in France,' billionaire Phil Shawe, 55, says by video call from a white-walled office in Puerto Rico, the tropical sun peeking through the shutters. 'I am tax exiled in Puerto Rico.'
Shawe affectionately calls Puerto Rico the 'one legitimate tax haven' in the U.S. He relocated to the island in 2018—the same year he won total control of his translation and language services firm TransPerfect—to counteract the effects of taxes related to the deal. Now, his primary residence is a sprawling Old San Juan mansion that was formerly home to the French consulate.
The move was also a symbolic end to an intense battle between Shawe and his former fiancée, cofounder and business partner of more than 25 years, Liz Elting. The pair had founded TransPerfect in a New York University dorm room in 1992 and continued to own and run it successfully for nearly two decades, even after she married someone else. Around 2011, though, things turned ugly, leading to legal battles in two states and lots of nasty allegations (battery by high heel, theft, break-ins). At various points, Shawe and Elting both wanted to buy each other out, but couldn't agree. 'Dysfunctional' was what a Delaware judge called the former lovers' relationship—just before he ordered the company's sale at a public auction in 2016. Elting declined to comment; Shawe underlined the company's financial success that year: 'By no measure was it dysfunctional … And the system that forced [TransPerfect] to spend $250 million in legal fees to run a forced unprecedented sale process is the one that is dysfunctional.'
More than a dozen bidders competed over four rounds to buy TransPerfect. It came down to three finalists: Shawe, Blackstone (in conjunction with Elting) and private equity firm H.I.G. (which owns TransPerfect competitor Lionbridge). Shawe won with a $385 million for the 50% he didn't own, valuing TransPerfect at $770 million.
Since taking over, Shawe has nearly doubled TransPerfect's revenue to $1.2 billion in 2024 in part via acquisitions, buying up nine companies for $40 million in just the last year; he's also succeeded by pushing into the AI realm. TransPerfect is using the technology in conjunction with humans to translate sensitive information and adapt content like websites to other languages and cultures (a service called localization). The company translates more than 7 million words a day on behalf of its hundreds of customers—including Microsoft, P&G, United and Pfizer.
According to Katherine Zinger, senior program manager at Microsoft, TransPerfect's GlobalLink program, which automates multinational businesses' process of translating content like websites into different languages, has helped reduce costs for such work by around 30%.
Profit margins in the industry are thin, roughly 7%, per Shore Capital analyst Katie Cousins. TransPerfect declined to provide specific profitability figures; as a private company, it isn't required to, but one of its financial advisors told Forbes that its margins are higher than the industry's average. Shawe has bigger plans and promoted longtime employee and potential successor Jin Lee as co-CEO last year to help him take the company to another level.
Forbes estimates that TransPerfect—owned 99% by Shawe and 1% by his mother—is worth around $1.8 billion, 2.3 times its value at the time of the auction. He thinks it's worth even more: 'I'd be a billionaire twice over if I sold the firm, but I don't have any intention to sell the firm. Thirty-two years in, and I'm still working pretty hard.'
T he earliest days of the company were exhilarating. Shawe and Elting were business students at NYU when they started the translation service out of Shawe's dorm room, bootstrapping the company with savings and credit card debt. Putting in 100-hour weeks, the then-couple created a network of freelancers to translate documents faster and better than competitors. The company grew quickly. They only took outside investment once, but later bought out the investors. 'We liked the freedom, being able to focus on the long-term vision and the lack of other decision makers,' Elting previously told Forbes .
Even as the pair's relationship grew rancorous, the company kept growing, reaching revenue of just over $700 million in 2018.
While Shawe was relieved when he finally got full control of the company, he was not happy buying it at auction, which he calls 'tax-stupid' and an 'unfair tax burden.' That's when he hightailed it to Puerto Rico. The U.S. territory has tax advantages that allow certain individuals—those who have relocated to the island in the last decade, donate $10,000 a year to a local nonprofit and establish residency, all of which applied to Shawe—to avoid taxes (including federal ones) on capital gains, dividends or interest. As four Congresspeople wrote in a 2023 letter, they are 'tax benefits that Americans could not obtain anywhere else in the world.'
Shawe also reincorporated TransPerfect in Nevada in 2018, due to his growing frustration with the Delaware Court of Chancery, where he says he faced hundreds of millions in attorney's fees connected to the TransPerfect litigation that 'put the company at risk.' It's part activism, part revenge campaign: Shawe has sued attorney Robert Pincus, the custodian in the TransPerfect sale, at least three times—mostly over legal fees related to the sale—and appealed the rulings more than a dozen times between 2017 and 2024. (Most have been dismissed and in judgments as recent as last week; Pincus declined to comment.) Shawe was also the biggest donor to Delaware politics in 2024, giving more than $1 million to a political action committee and helping get the state's current governor elected. Further, he solely funds advocacy organization Citizens for Judicial Fairness, aimed at making the chancery court more transparent—and less powerful.
H istorically, translation companies have been 'smaller mom and pop businesses' where it's difficult to 'achieve the scale to be attractive to public markets,' says one of TransPerfect's financial advisors. But lately a handful of companies have been grabbing more of the market including RWS, California-based private company LanguageLine and TransPerfect, the three industry leaders.
TransPerfect now has 10,000 employees across 50 countries—up from 5,000 in 2018—who help translate everything from legal documents and patents to marketing materials and signage. Longtime employee Kris Marrero, senior vice president of production, says many staffers are extremely loyal to Shawe, crediting him for creating a unique culture that includes annual 'Avengers' strategy meetings that bring together top executives—held at locales ranging from Buddhist temples in Bhutan to waterfalls in Iceland.
'Phil says to us, 'Never make somebody do a job that you wouldn't do yourself,'' Marrero says. 'When I was an early manager, [I had] a backlog of projects and Phil came to my office and helped me work through them one by one.' Senior vice president of tech operations Joe Campbell recalls Shawe cold-calling linguists at 2 a.m. for assistance on a big translation project. Campbell, who has been at the company for 14 years, says he shared an office with Shawe for about a decade. He says Shawe doesn't like to have his own office in part because he likes to mentor people and have them sit in an office with him.
Not everyone gives such glowing reviews. There are hundreds of reviews on Glassdoor complaining about low pay and long hours. 'Our compensation structure conforms to or exceeds the norms for each market,' Shawe wrote in an email to Forbes . 'TransPerfect staff worldwide are properly and fairly compensated.' Plus former TransPerfect employees filed a class action suit in 2019, alleging that the company failed to pay overtime wages; it included the 'hundreds' of employees paid less than $1,125 a week in TransPerfect's New York offices. (That's less than the minimum that they'd have to be paid to be exempt from overtime pay).
Shawe, not one to stay out of the courts, sued the lawyer representing the class, Jeremiah Frei-Pearson, for defamation in May 2024. Frei-Pearson told Law360 that TransPerfect undertook 'intentional' wage theft, adding that 'instead of resolving this straightforward wage and hour case, TransPerfect has used every trick in the book to delay the day when it is forced to pay the workers it victimized.' Shawe sued again in February, this time for trademark infringement, accusing Frei-Pearson's firm of using a badly-altered version of TransPerfect's trademark in materials used to recruit additional members of the class. Frei-Pearson didn't respond to a request for comment. Both cases are ongoing.
Shawe claims the class action is about attorney fees and says he won't settle despite negligible damages because he does not believe TransPerfect 'did anything wrong' and that doing so would bring 'more frivolous litigation.'
It faces another class action stemming from a lawsuit initially filed in 2022 by a former contractor in California. The former contractor accuses TransPerfect of misclassifying her—and 'more than 100 putative class members'—as independent contractors and failing to provide 'timely payment,' overtime and rest breaks.
' The good news is, I have a lot of lawyers,' Shawe says—adding that those same lawyers could help Forbes access the court transcripts faster and cheaper.
More than in almost any other industry, AI—particularly the rise of machine translation—has affected language services outfits, which began adopting the technology around a decade ago. Still, there's a difference between a company like TransPerfect and something like Google Translate, Shawe explains. With the latter, 'you basically give up the rights to whatever is in that document and Google is allowed to publish that document publicly, or use it to index.' In contrast, TransPerfect's customers include firms that have a great need for confidentiality and accuracy, including the U.S. Departments of Justice, Energy and Homeland Security and pharmaceutical giant Gilead Sciences. Depending on the client, employees still review almost all of TransPerfect's work.
Shawe has been taking advantage of the AI boom by snapping up small companies in new areas. Among them: simultaneous interpretation platform TheSpeech and Switzerland- and Germany-based language services company The Apostroph Group. Shawe, who claims he reinvests most of the firm's profits back into the company rather than paying himself dividends, says he has still around $200 million set aside to acquire more. TransPerfect has also been working with Microsoft to pilot some new AI products, for example, says Zinger, and it's been casting about internally for other business opportunities.
'Translation is facing headwinds—mainly because more and more projects are suitable for automated solutions,' Shawe wrote.
A
ccording to Shawe, the company's fastest-growing lines of business include over-the-phone interpreter TransPerfect Connect, data collection and annotation arm DataForce and the electronic discovery subsidiary of TransPerfect Legal Solutions. The latter two—both of which are doing well, bringing in $49 million and $125 million in 2024 respectively—underscore Shawe's emphasis on internal innovation. For instance, DataForce, which employs contractors from around the world to help anyone from autonomous vehicle firms to pharma companies collect and label the data needed to train their specialized AI models, has evolved thanks to ideas at TransPerfect's annual hackathon. Meanwhile, the legal solutions business came about after Shawe learned that some customers weren't happy with their existing electronic discovery providers (the process of collecting and sharing electronic information in lawsuits). So it created its own.
In Shawe's words: 'Cannibalize yourself. If you can bring a better solution by bringing a technology solution to them, even if it's going to mean a decrease in your services revenue, you bring it. Because if you don't, someone else will.'
More from Forbes Forbes Crypto Goes Corporate As A New Wave Of Public Companies Buy Bitcoin By Nina Bambysheva Forbes LA Residents Are Foiling ICE Raids Using Amazon Ring's Neighborhood Watch By Thomas Brewster Forbes How Barron Trump May Have Earned $40 Million From His Dad's Crypto Venture By Kyle Khan-Mullins Forbes Trump's Former Pal Plans To Beat Tariffs And The Immigration Crackdown By Giacomo Tognini Forbes How Comedy Creator Adam W Built A Multi-Million-Dollar Media Brand By Steven Bertoni