Cicero Learning

In an era when remote work and global mobility are reshaping lifestyles, one entrepreneur is applying those same principles to education. Paul Bennett, a three-time founder, drew inspiration from his family's decade-long circumnavigation of the globe to launch Cicero Learning, a platform designed to revolutionise one-to-one personalised education for families who refuse to let geography limit opportunity.

Bennett's career began in journalism, where he earned accolades including recognition in Best American Science Writing and a Lowell Thomas Travel Writing Award for his contributions to National Geographic and Wired. He later co-founded Context Travel, a B Corp–certified experiential travel company that connects curious travelers with local experts. The company appeared on the INC 500 list of fastest-growing companies and received a Changemakers award for sustainability, representing a category-defining success before its partial exit.

Rather than slowing down, Bennett embarked on a family adventure: sailing around the world with his wife and three daughters (then ages 5 to 18). This 'boatschooling' experience revealed a significant gap. Traditional schooling models struggled to accommodate a nomadic, work-from-anywhere lifestyle.

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

That challenge ultimately led to the creation of Cicero, Bennett's third startup and a public benefit corporation.

Cicero connects families with expert private teachers who deliver remote, customised one-to-one learning experiences. Unlike conventional classrooms that teach to the average student, Cicero's approach is entirely personalised. Courses are designed around each learner's interests, pace, and schedule.

Rooted in classical mentorship models but adapted for today's digital world, the platform emphasises relationship-driven education. Teachers act as guides and co-discoverers, helping ignite curiosity and foster deeper engagement with learning.

Research supports the approach. Educational psychologist Benjamin Bloom's '2 Sigma Problem' demonstrated that students receiving one-to-one tutoring perform two standard deviations above the average classroom learner—often transforming potential C-level performance into A-level mastery. Cicero graduates have already gained admission to elite institutions such as the University of Chicago and Cambridge, demonstrating that flexible, location-independent education can produce world-class outcomes.

Bennett's diverse background further shapes Cicero's vision. A homeschool parent and global sailor, he also serves as executive chair of Sustainable Travel International, board chair at Modern Adventure, an angel investor, and an advisor to companies across sectors including fintech and healthcare. His experience on both sides of the entrepreneurial table—raising capital as a founder and evaluating opportunities as an investor—provides a unique strategic perspective.

Looking ahead, Bennett aims to enroll 5,000 students and help reshape education for a mobile, curious generation. In a world increasingly defined by remote opportunities, Cicero offers a scalable solution for families who prioritise personalised growth over rigid educational structures.

For more on Cicero Learning, visit cicerolearning.com.