Serial Founder Turns Decade of Global Sailing into Ed-Tech Platform

Paul Bennett's Cicero Learning offers personalized, one-to-one online education for families seeking location-independent opportunities.

Published on Mar. 5, 2026

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Inspired by a decade of 'boatschooling' while sailing the world with his family, three-time entrepreneur Paul Bennett founded Cicero Learning, a platform designed to revolutionize one-to-one personalized education for families who refuse to let geography limit opportunity. Cicero connects families with expert private teachers who deliver remote, customized learning experiences tailored to each student's interests, pace, and schedule.

Why it matters

As remote work and global mobility reshape modern lifestyles, Cicero Learning provides a scalable solution for families seeking personalized educational opportunities that can accommodate a nomadic, work-from-anywhere lifestyle. The platform's approach is rooted in classical mentorship models but adapted for the digital world, emphasizing relationship-driven education to help ignite curiosity and foster deeper engagement with learning.

The details

After co-founding the experiential travel company Context Travel, Bennett embarked on a family adventure: sailing around the world with his wife and three daughters. This 'boatschooling' experience revealed a significant gap, as traditional schooling models struggled to accommodate their nomadic lifestyle. That challenge led to the creation of Cicero, a public benefit corporation that connects families with expert private teachers for remote, customized one-to-one learning experiences. Unlike conventional classrooms that teach to the average student, Cicero's approach is entirely personalized, with courses designed around each learner's interests, pace, and schedule.

  • In 2026, Paul Bennett founded Cicero Learning.
  • Cicero Learning has already helped students gain admission to elite institutions like the University of Chicago and Cambridge.

The players

Paul Bennett

A three-time founder who drew inspiration from his family's decade-long circumnavigation of the globe to launch Cicero Learning, a platform designed to revolutionize one-to-one personalized education for families seeking location-independent opportunities.

Cicero Learning

A public benefit corporation founded by Paul Bennett that connects families with expert private teachers who deliver remote, customized one-to-one learning experiences tailored to each student's interests, pace, and schedule.

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What they’re saying

“We wanted the freedom to travel and live anywhere, but with kids in that age range, the big question was: what do we do about school?”

— Paul Bennett, Founder, Cicero Learning (ibtimes.co.uk)

What’s next

Cicero Learning aims to enroll 5,000 students and help reshape education for a mobile, curious generation.

The takeaway

In an era of remote work and global mobility, Cicero Learning provides a scalable solution for families seeking personalized educational opportunities that can accommodate a nomadic, work-from-anywhere lifestyle, proving that flexible, location-independent education can produce world-class outcomes.