A language CEO, 20 years in, now building his own AI

Sean Hopwood started a company in 2007 without owning a computer. Nearly two decades later, Day Translations works with more than 10,000 linguists and has offices on three continents, all without a dollar of outside investment.

In this CEO-to-CEO edition of In Other Words, Sean joins Phrase CEO Georg Ell to share how he built a global language services business funded entirely by client revenue. His interest in languages began at eight, when he started learning Spanish in a small Florida town. He now speaks eight languages with varying fluency. The company takes its name from his grandfather, a Marine and Kodak executive whose influence still guides his approach to running it.

Sean describes persuasion as “just another language” and explains how he connects financial goals to the work his team cares about. He also recalls a client who canceled on a Friday and returned on Monday after his development team built an AI interpreting service over the weekend.

Looking back, Sean would have adopted technology sooner and brought in leaders with corporate experience earlier. He reflects on how corporate expertise can complement the language knowledge that helped build the business.

What You’ll Learn:

Would you have started a business in 2007 if you’d known a financial crisis was coming?
How do you build a commercial mindset in a company founded on a love of languages?
A client cancels on Friday. Can you win them back by Monday?
When should a founder bring in corporate experience?
Where does AI fit in a business built on human language expertise?

Sean Hopwood is the founder and CEO of Day Translations, which serves clients in healthcare, legal services, government and insurance. He launched the company from a university computer lab in Tampa, Florida, in 2007. Funded entirely by client revenue, the business now works with more than 10,000 linguists and has offices on three continents, serving clients in healthcare, legal services, insurance, and government

Sean speaks eight languages with varying levels of fluency. He grew up in Bartow, Florida, with a Lithuanian father and an English-teacher mother, and began learning Spanish at eight. He majored in Spanish at the University of South Florida before pursuing an MBA.

He named the company after his grandfather, Francis Joseph Day, a former Marine and Kodak executive who helped shape his approach to business. Sean has received Comparably’s Best CEO for Women and Best CEO for Diversity awards and is now expanding the company’s use of AI, including AI-powered interpreting services.

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Highlights and YouTube Chapters:

00:12 Introducing Sean Hopwood and Day Translations
01:28 The Marine's Grandson Who Gave a Company Its Name
04:48 Why a Dictionary Is This CEO’s Favorite Way to Learn
07:08 Why a recession turned out to be the right time to start a business
10:41 Nearly 20 Years, Zero Outside Investors
13:14 Building a Commercial Mindset Inside a Company Founded on Language
15:55 Comparably’s Best CEO for Diversity on Building Culture That Travels
19:57 A Bootstrapped Language Company That Built Its Own LLM
24:27 "If the Client Asks for Shoes, We'll Make Shoes"
27:48 A Client Canceled on Friday. By Monday, They Were Back.
32:33 "Are We All Going to Be Mirrors Talking to Each Other?"
35:04 When 10,000 AI Agents Work Together for 88 Hours
37:56 The One Thing He Would Do Differently After Two Decades

Episode Resources:

Sean Hopwood, Founder & CEO at Day Translations
Day Translations Website
Georg Ell, CMO at Phrase
Phrase Website