Over the past several years, the education landscape has changed exponentially. While the sector was full of classical traditions and fairly strict regulations for a long time, new technological tools steadily introduced over the course of the 2010s began to open new opportunities.
Then, in 2020, the door for innovation was blown wide open as COVID-fueled lockdowns were enacted. Suddenly, the embracing of new tools for learning in the education sector wasn’t just a possibility; it was an outright necessity.
While COVID lockdowns have long since ended, many industries redefined during this period have remained in flux. It’s difficult to put the genie back in the lamp, so education has remained a more open and diverse sector. Nowhere is the immense potential of embracing these new learning tools and opportunities more apparent than in Paul Bennett’s Cicero Learning.
What Is Cicero Learning?
Cicero Learning grew out of founder Bennett’s real-world struggle to educate his children while living a mobile, travel-based life, and now positions personalized remote one-to-one teaching as a flexible alternative to traditional schooling.
Interestingly enough, Bennett didn’t set out to play an integral role in revolutionizing remote learning. Rather, he was simply trying to figure out an effective way to educate and inform his own children while living his fast-paced, on-the-go lifestyle.
Considering that he had already founded and exited two different companies, Bennett was actually looking to take some time off and really enjoy his family and the world at large. This led him to take his wife and three daughters out on the open ocean to sail together. However, during this time, a new need became apparent, and Bennett couldn’t help but get involved.
Paul Bennett’s Background
As an award-winning journalist for outlets such as National Geographic and Wired, Bennett has earned honors including the Best American Science Writing accolade and a Lowell Thomas Travel Writing Award. Spurred on by this formative success, he decided to co-found Context Travel, a category-defining experiential travel company. As a certified B Corp, the company appeared multiple times on the INC list of fastest-growing companies and won a Changemakers award for its sustainability strategy.
When a new challenge presented itself in the wake of his family’s sailing venture, Bennett tackled it head-on. Though the journey offered incredible experiences, such as endless horizons, cultural immersion, and personal growth, educating his daughters remained a consistent hurdle.
It soon became apparent that sailing, with its off-kilter hours and constant travel, was in direct contrast to more traditional schooling options. Despite having figured out how to manage the remote work aspects of his and his wife’s jobs, the remote schooling consistently proved troublesome.
Bennett says, “We wanted to travel the world and work from anywhere, but with kids in that critical age range, what do we do about school? Viola, Cicero was born.”
Offering Options to Families on the Go
Cicero Learning is a public benefit corporation and marketplace that connects families with expert private teachers for remote, one-to-one personalized learning engagements. It’s not about generic tutoring or bundled classes. Cicero matches learners with inspiring mentors who design custom courses tailored to each student’s unique pace, passions, interests, and schedule.
In a sector generally full of absolutes, Cicero offers real flexibility. Through the platform, students can learn from anywhere, adapting to travel, work-from-anywhere lifestyles, and uniquely modern family rhythms. The proof of Cicero’s educational capabilities is truly in the pudding, as graduates have secured spots at elite universities like the University of Chicago and Cambridge. This indicates that personalized, relationship-driven education can and often does deliver exceptional outcomes without tying families to fixed locations or schedules.
Cicero’s Success
Bennett’s background gives Cicero a rare edge. As a homeschooler and circumnavigator himself, he brings a uniquely lived authenticity to a space often dominated by thinkers rather than doers.
His broader career adds layers: executive chair and board director at Sustainable Travel International (a public benefit corp tackling climate change and overtourism in fragile landscapes), chair of Modern Adventure (a VC-backed startup creating experiential marketing with chefs, scientists, and athletes), angel investor, mentor in accelerators like Plug and Play and MassChallenge, and consultant/advisor to diverse ventures (from a $700M fintech’s DTC strategy to a healthcare startup’s business plan and a music publishing company’s fundraising).
Bennett’s vision is ambitious yet grounded: enroll thousands of students, empower “live anywhere” families, and prove flexible, one-to-one learning can outperform rigid systems. In a world of remote work and nomadic lifestyles, Cicero addresses a growing need: world-class education that travels with you.
