With modern technology helping us stay connected and a rise of remote working opportunities, more and more people are embracing unconventional lifestyles and aiming to make the most of travel while they work away from the traditional office desk.
But what happens logistically when you bring family and kids into the mix?
This is a situation Paul Bennett faced when he decided work remote and sail around the world with his 3 daughters. He valued their education and college planning, but also valued the family time and freedom of travel that they enjoyed with their unconventional lifestyle. After trying a few homeschooling alternatives that were lacking, he took matters into his own hands. Using his experience founding multiple businesses, he developed Cicero, a platform that allows families – just like his – to connect with private teachers and courses and give their learners a quality education while embracing the flexible lifestyle they want to have.
Allow me to introduce Paul Bennett…
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My name is Paul Bennett, and I’m a 3x serial founder who’s latest startup is Cicero, a platform for finding and hiring private teachers who design personalized courses and lead them one-to-one with homeschoolers, worldschoolers, and adult learners. Cicero empowers students (and their families) to build school around their interests, needs, and passions. It’s a completely flexible and portable alternative to school that delivers 2-3x results.
I’ve founded two other businesses, in the travel space, and do a lot of advising of startups and founders. So, I have the startup disease.
After a partial exit from my first company, Context Travel, I bought a boat and sailed around the world with my wife and three daughters, which was an amazing experience that “slowed down time” so that I could cherish my kids during their teen years. This was also a challenging moment, in terms of school. We became homeschoolers—well, “boatschoolers,” to be exact—for which we had very little training or background. And, we found the homeschooling landscape to be extremely fragmented; but, also, there was nothing amazing for our kids. Most homeschooling solutions were either a curriculum in a box in which the kids just went from workbook to workbook, checking boxes; or, there were online courses with ten to twenty kids jammed into a Zoom screen. None of it was very inspiring; most of it was a step down from what we’d known on land.
At the same time, my wife and I strongly value education. I did my master’s degree in the great books at St. John’s, and our dinner table conversations are usually about something meaty like how to define virtue or how mRNA works. We needed something flexible for our super remote life—we spent two years sailing through Papua New Guinea and Indonesia—and something incredibly robust that would spark a love of learning with our kids. One day, my wife Lani had the idea of hiring a professional teacher to design and lead a high school English language arts course for my oldest daughter. This resonated with my background in the classics. After all, most of the great thinkers in history, from Alexander the Great to Bertrand Russell, were educated by private teachers.
For us, it was life changing. My daughter built an incredible connection with her teacher, who designed a curriculum that met her where she was and then challenged her; and the learning was more profound than anything we’d experienced—even back in the fancy private school that my kids had left in the U.S. when we started the voyage.
We knew we’d hit gold. One-to-one learning is a game-changer in education, especially in a world of living anywhere. It unlocks so much.
Cicero has a many of the same dynamics as our first business, Context Travel. That business matches intellectually curious travelers with local experts—mostly Ph.D.-level historians and other academics—in cultural destinations around the world for very personalized, conversational, tour experiences. At Cicero, we needed to recruit a similar network of brainy, passionate, educators. And we needed to find families who value learning and education above a lot else in their lives.
These kinds of marketplace businesses are challenging because you do a lot of building and flying the plane simultaneously. It doesn’t make sense to focus solely on recruiting teachers until you have demand; but, also, if you just focus on customer acquisition, you find yourself caught out with very granular demand—”I want a mechanical engineer to teach my daughter how to build prototypes”—that can be difficult to meet. So, you have to do both at the same time.
We made a ton of mistakes with our first business, including building a custom tech product out of the gate in order to meet all sorts of operational, service-delivery objectives. That ended up being expensive and incurring lots of tech debt that was difficult to pay down in years 4-5. So, with Cicero we decided to go super light, launching on a WordPress platform with a backend that mixes lots of off-the-shelf components like Google Workspace, Airtable, and Zoho products. It feels great to be very lean in this regard.
We did the beta test with our first daughter while sailing through the Solomon Islands and Papua New Guinea, and then expanded to our other two daughters when we got locked down in a remote island off the coast of Sumatra during COVID. Since most of the world started homeschooling then, we got a ton of interest from random families who heard about our experience. We launched the business a few months later from Cape Town as we began closing the loop on our circumnavigation.
Launch was intentionally soft. We new our one-to-one model worked amazingly well for us as a family. However, besides being a single data point, we’re also an edge case. How many of our potential customers would be living on a sail boat, circumnavigating? So, we rolled out via word-of-mouth for the first term and onboarded about four or five other students, found them teachers, and stayed really close to the product experience. It turned out our original test was spot-on. Families and students loved having their own private teacher; and the learning that takes place when a teacher and student build a strong rapport was transformation.
We launched formally in the spring of 2023.
Our best customer acquisition channel is word of mouth, which is common when you have an incredible product like this. It sells itself. But, word of mouth is a slow burn, especially when the sales and service cycle is long—which it is in a business like this. So, we’ve tried the full range of other customer acquisition tactics. The second best channel for us is partnerships and referrals, especially with influencers. We’ve onboarded a half-dozen moms who have strong, engaged followings on Instagram, and who can tell a great story to their audiences about the experience. Depending on the influencer, this can drive great lead gen.
Retention in a business like this is all about quality assurance and the product. There’s a lot at stake. I think most of our customers are like me: My kids are the most important thing in my life. The decisions that I make about their education matter. Education is the single largest line item in our family budget, by a wide margin. The great thing about Cicero’s one-to-one educational model is that it delivers results that are two standard deviations above the mean (ref Benjamin Bloom’s seminal study on one-to-one learning). So, as long as we stay on top of the product—recruit amazing teachers and equip them for success—we keep customers. The LTV is great in this business.
I don’t listen to a ton of education podcasts or read much about education because I find a lot of institutionalized thinking on the topic to be overly focused on schools, curriculum, and testing. We’re not a school, our curriculum is student/family-driven, and our assessments are based on one-to-one interactions, not standardized tests. So, I don’t find a ton of that relevant. That said, a couple of key sources have been the work of Mary Helen Immordino-Yang, a neuroscientist, on the role of emotion in learning, and, of course, the wonderful Ted talks by Sir Ken Robinson about how schools are broken. Kelly
I go through phases of reading and listening to business and startup books and podcasts. But, again, don’t find a ton of them super helpful. Some outliers are the Acquired podcast, in which two venture capitalists, Ben Gilbert and David Rosenthal, break down successful businesses into their component parts. Their analysis of the business of Taylor Swift is incredible.
Cicero is growing rapidly. We live in a time of extreme possibility in education. Public school enrollment is dropping in the U.S., and homeschooling is growing 50%+. Parents can work from anywhere and, like me, want to see the world with their children, slow down time, and ensure that they acquire the spark of lifelong learners. Cicero is instrumental in this equation. I only see that increasing.
Bootstrapping a small business means that you do everything, from bookkeeping to sales. You can’t and don’t have to be great at everything, but you have to be competent. And, in order to achieve competency in a wide range of domains you have to absolutely love learning and knowledge acquisition. Being a life-long learner is a founder’s super power.
Beyond this, sales. A founder has to be a great sales person. I’ve seen co-founder teams where not each member is great at sales. But, at least one has to be brilliant at it. Luckily, sales is learnable. If you’re passionate about your idea and can articulate it well, adding a few grace notes from sales handbooks is pretty straightforward. But, without passion and articulation, it’s a pretty steep climb.
Cicero is at:
https://cicerolearning.com
https://www.instagram.com/cicerolearning/
https://www.facebook.com/cicerolearn/
https://www.linkedin.com/company/cicero-learning
I can be reached at:
https://www.linkedin.com/in/paulbennettfounder/
paul@cicerolearning.com
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