Paul Bennett
Cape Town · New York City · Rest of World
Seasoned founder and strategic advisor in travel, learning, and sustainability.
An AI-native mindset and a bias toward building. Available for advisory work, consulting, and board roles.
Currently
- Advising Airbnb on their Experiences rollout
- Building AI-powered sustainability tools with Sustainable Travel International
- Revolutionizing education with Cicero Learning
Current engagements
Where I work.
Airbnb
Strategic Advisor
I've been advising Airbnb on its Experiences rollout since early 2025, bringing years of pattern recognition to a young team to help them understand — and capitalize on — the market dynamics in tours and attractions. Lately I've been building tools, supporting new partnerships, and helping bring a founder's mindset into the organization.
Context Travel
Co-founder & Board Member
I co-founded this category-defining experiences company, which provides expert-led cultural tours across 85+ cities worldwide with 1,200+ PhD-level guides. The original thesis: depth beats checklists in travel, and people will pay for someone who can put a place in context.
Sustainable Travel Intl.
Re-founder, Board Chair & Product
I revived and re-founded this iconic organization alongside the CEO. We're building AI-powered tools to dramatically improve impact intelligence across the travel industry: measuring carbon, biodiversity, plastics, and social impact in ways that are commercially real, not just marketing.
Cicero Learning
Founder
A scrappy startup that unlocks 1:1 learning at scale — one student and one great teacher at a time. I iterated on this model with my three daughters while we sailed around the world over eight years during their middle and high school careers. What started in a cockpit off Papua New Guinea is now available to families everywhere.
Also
What I do
Where I add the most value.
01
AI strategy with a bias to building
Hands-on experience building apps, pipelines, orchestration layers, and agents across a wide range of use cases. Design thinking and a product mindset have never been more important — and figuring out how to inculcate both in a culture is often the real work.
02
Travel industry expertise
I advise travel companies big and small, from low price point to ultra-luxury, across org design, capabilities, distribution, supply, and sustainability. Deep experience with tour operators and the tours and attractions sector, a $375B market that most large platforms still misunderstand.
03
Sustainability as strategy
Sustainability is not a marketing layer. Correctly understood, a sustainability strategy can strengthen stakeholder engagement, enrich culture, and transform an okay company into a great one. I help leaders make this happen.
04
M&A and competitive intelligence
Help boards and leaders develop their exit strategy or pursue growth through acquisitions — from exploring adjacencies and target development to pitching and closing.
05
Founder whisperer
I speak the language of scrappy startups and can help early-stage companies look around the corners and ask the questions they may not yet be asking. Often engaged as executive chair or strategic advisor to founders who want a thought partner who's been down the path before.
06
Learning
A Great Books education followed by decades of building. I think rigorously about how organizations and individuals learn, and how AI is changing this. I live at the intersection of technology and learning, with a strong index on the human.
How I think
The right questions.
“It is not the answer that enlightens, but the question.”
I was trained in the humanities before I was trained in business: a master's degree in the Great Books at St. John's College, where the emphasis is on close reading and asking the right questions. That grounds how I work. When I sit with a product team or a board, I try to find the question they haven't asked themselves yet — whether it's in the data or the conversation. I find this approach is more useful than ever as AI hype threatens to drown us. My skill lies in the ability to tell the difference between a real shift and a polished deck, and having built enough to know what matters.
S/V Dafne · 2013–2024
Why I think differently about travel.
In 2013, my wife Lani and I pulled our kids out of school and set off on a decade-long odyssey aboard our catamaran, Dafne. We had three daughters — Stella, Cleo, and Jade — and a burning question: what would it look like to actually live in the world, rather than just visit it?
Eleven years and 40,000 nautical miles later, we'd crossed every major ocean, anchored in remote harbors off Papua New Guinea and the Chagos Archipelago, homeschooled three kids on a satellite connection, and started two companies from the cockpit.
Cicero Learning grew out of that adventure. So did a conviction that travel is most meaningful when it changes you. Not when it ticks a box.
In my fifties now, Lani and I are outliers in the digital nomad world. We split our year between Cape Town, New York, and wherever the work takes us — Europe, Asia, and occasionally somewhere with terrible internet and very good food. The nomad story didn't end when we sold the boat. It just changed its shape.
This is why I think about travel differently: not as logistics, or inventory management, or yield curves — but as the very human act of going somewhere, meeting strangers, and being indelibly etched by it.
Scroll the map sideways
40k
Nautical miles
11
Years at sea
3
Daughters boatschooled
Let's connect
Cape Town.
New York.
Wherever.
Available for advisory work, consulting, and board roles. Best fit: travel companies, organizations addressing the travel industry, any business grappling with AI integration, and founders who want a thought partner.