Dispatch from the deep end: are we ready for a cruise ship with founders?
The ROI of rest and what a cruise taught us about momentum
As we navigate this next wave of AI, I hear the same quiet grapplings from smart minds. I don’t have answers but something happens when the right mix of people are together: we become lighter and move forward.
That’s the spirit of M13’s media events where we gather top-tier journalists, early-stage founders and investors and comms leaders who are rarely in the same room. I don’t assume magic every time but I’ve learned to trust that more often than not, they leave seeing things differently.
We’ve gathered everywhere from my dining room to a Spanish grocery store, a journalist’s bookstore, the M13 office and, most recently, somewhere no self-respecting tech founder expected to be: a cruise ship.
Cruise ships elicit strong reactions. They’re not easy to board even when they’re not sailing anywhere. I didn’t know if my time-constrained media and tech friends would come. Also it was back-to-school week and US Open. Also people don’t click links and didn’t read who I’d ask to speak. Hint:
And yet, they did respond. RSVPs kept rolling in.
M13 events are designed for range, mixing play and connection with content. The audience is as impressive as the speakers. We convene rising stars and superstars, media and comms strategists, legacy media under pressure to roll out AI with tech founders who know what it takes to unify fragmented knowledge so AI can actually work at scale.
The event’s program featured three short conversations including one where Every co-founder and CEO Dan Shipper discussed “Think Week,” periodic time away from the demands of the day-to-day for his 15-person AI-native company to tinker, explore and experiment. Their most recent one took place in upstate New York.
“You can’t always innovate during the work week. Giving time for people to take risks and play around allows them to try new things. It's good to do when technology is doing this.” Dan Shipper
It reminded me: hey, we did something like this. On a ship in 2023. And it was led by women.
At that time, Virgin Voyages was unproven. The speakers were asked to facilitate chats and workshops during a four day sail — so they couldn’t just pop in and duck out.
The speakers knew me but not each other nor what to expect. They didn’t come for a paycheck or press. They said yes for me, and I didn’t take it lightly. But I was so focused on what the audience would receive that I underestimated what would happen when these charismatic, accomplished leaders got together onstage and also learned from each other.
It was a real learning for me.
I felt the electricity as soon as the very first panel started. The Red Room lit up from their openness and humility, lived experience and fresh stories, their chemistry. People were on their feet.
I wanted my speakers to meet. Not just pass each other backstage but really connect. So with the help of Taylor from Virgin Voyages, we gathered them for lunch on that first day.
They were thrilled and immediately began chatting with the person next to them. I wondered as I looked around the room: do they know the full awesomeness of who they are talking with? That impulse led me to do something spontaneous. I stopped the individual conversations and asked the group to introduce themselves and share:
What’s something you need help with? What’s something you can help with?
First of all, if they were too humble in their intros, I filled in (that’s just what I do: I see people in their fullness and connectedness).
Then, on my two questions: their vulnerability and candor about their hopes and uncertainties set the stage for the rest of the cruise and drew them close in unexpected ways. I’ll never forget their raw honesty and what that unlocked.
What’s this got to do with Every’s “Think Week?” ROI.
Two years later, I reached out to the speakers and asked if the cruise had made a difference. I asked in an email: Did the cruise have an impact on you? Are you in the same place you were back then?
They wrote back and said they had first identified as speakers so they didn’t know how much they themselves needed the cruise. They shared rich details about big life and professional changes, health and heartbreak. They had walked onboard knowing just me, and today they’re still in touch and supporting each other. And there’s more.
Here’s what my friends said and Virgin Voyages continues to teach me about designing for connection and community.
1. Presence is power
One of the rare silver linings of the pandemic was a willingness to say yes to the unknown. Maybe because so much was unknowable and could be, and was, taken away from us.
The curated speakers arrived ready for whatever might unfold. Stacy London remembered meeting a guest who sought her to share a devastating story: she went in for an endometriosis procedure and woke up to learn that a radical hysterectomy had been performed, without prior discussion.
“It’s cruises like the one we joined and special places for women to congregate that makes all the difference in reducing ignorance about our health and on insisting that education is part of bodily autonomy.” Stacy London
The speakers received something deeper than what they gave: they became fully present to each other and to themselves.
“I couldn’t have said what I wanted then but what I got was a moment to step into myself that I didn’t know that I needed. And that’s been an inspiration ever since.” Rei Chou
In a world built for performance, even on a ship filled with stages, spotlights, sequins and dancers, Virgin Voyages became paradoxically a space to just be. It wasn’t a break from life but a return to it.
2. What matters is the inbetween
“Culture is created in the in-between spaces and through invitation.” Rei Chou
An intentionally designed structure invites meaning even in the inbetween moments. On a cruise, time stretches, social metabolism slows, and that slowness enables real connection.
There are no Ubers to rush to the next event, no back-to-back zooms. On Virgin Voyages, we had time for karaoke, cold plunges, sound baths, beach walks and surfing, and late-night pizzas under the stars. Much of this was unplanned. We bumped into each other and tried things we wouldn’t in the real world. Including lingering for longer and deeper conversations.
And that nurtures the roots for digital connection that forms modern communities.
Natalie Kuhn continues to facilitate high-impact programs on Virgin Voyages and maintains deep and robust friendships with not only each facilitation crew via WhatsApp and in-person but also sailors she has gotten to know through multiple trips.
“The relationships deepen, and it’s a wonderful way of reuniting and creating community with folks you wouldn’t normally cross paths with in your everyday life. Life becomes so much more technicolor, and my perspective becomes wider because of the kind of community that Limitless continues to provide in my life.” Natalie Kuhn
3. Ambition redefined
“I reflect on how powerful it is to know when things should come to end. Endings are beginnings, and over two years, I've had a lot of those.” CJ Frogozo
During the lunch, a shared narrative emerged, one we’re seeing more broadly in this cultural moment: a shift away from titles, speed, status and toward inner alignment.
Two years later, Nathalie Walton wrote, “The seeds I planted are starting to bloom.”
Rei meditated on what “enough” means, Jill gained clarity of purpose, and Stacy began the quiet work of shedding people-pleasing. This is an evolved definition of success, an expression of strength that’s personal and sustainable.
Looking back, we were ahead of the curve, curating space for a new kind of ambition and a way of showing up, before we had the words to name the shift.
4. Ripples before results
“Virgin Voyages continues to ripple through my life in unexpected ways. I’m still in touch with many of you. The journey and the community keep on giving.” Nathalie Walton
Even as technology accelerates the pace of change, transformation isn’t a glow-up or viral story. This wasn’t a one-and-done retreat. It was the start of new possibilities, not only on stage but in the longer arc of our lives.
“The voyage was life-changing. It helped me rethink how I lead professionally. I met people I never would’ve crossed paths with, full of spirit, intelligence, and generosity. The creativity, vulnerability, and movement were unlike any experience on a cruise.” Andrea Sullivan
“Am I in the same place as in April 2023? No! I am ever-evolving. In work. In life. In boundaries. In self care. I try to be better every day. Only forwards. Not backwards.” Carrie Byalick
Rethinking ROI and hidden metrics that matter to me
Sylvia Solit calls me a translator and a bridge across worlds so here I offer both visible metrics and hidden returns that matter.
“It gave me the space to really check in—on who I am, what kind of impact I want to make, and how to build momentum around the things that actually matter to me.” Jill Lindsey
I’m sharing these stories with their blessing because they reflect real progress. None of this was planned, and it couldn’t have been planned. Since the cruise…
Andrea is leading her own leadership accelerator for c-suiters.
CJ established new roots in Florence (yes, Italy) while deepening them in New York, choosing presence over place and community over geography.
Jill closed a chapter, started a family and launched a new business.
Natalie is studying to be an interfaith minister and moved to London to construct a studio.
Nathalie found clarity in ambiguity. And accepted a leadership role in a sleep tech company.
Rei found a boyfriend and her voice launching two movements.
Sylvia is focusing on purpose and impact: she helps founders discover life after exit, joined Prime Quadrant and leads a crowdfunding platform to back environmental litigation.
Stacy is immersed in a new phase of creative curiosity.
Observable ROI: Roles shifted. Companies launched. Networks activated. Partnerships formed.
Unseen ROI: Courage sparked. Boundaries drawn. Self-trust reclaimed. Leaders born.
So… could this work for tech founders?
That’s the question I’m sitting with now. The recent M13 x Virgin Voyages gathering— hosted aboard a ship of generous guests and speakers and a brilliant crew representing 77 nations working together in seamless collaboration — confirmed what we’ve been sensing: something is shifting.
“The real infrastructure for innovation is trust, connection, and relationships.”
That’s me describing what I learned during my dozen plus years at Virgin. It’s what I see at M13 as we partner with trusted investors and founders to build what’s next.
What would it look like to design a Think + Play summit for founders, not to pitch but to play and not to impress but to tinker?
Innovation doesn’t start with tech alone. It starts with open people and spaces where they are encouraged to reflect, learn and grow. And maybe then, we build more products that serve humanity, not the other way around.
I don’t know where these musings will go, and that’s OK. I sense a craving for kindness, integrity, compassion, sharing. I refuse to believe that mean is the new black! I want to slow time down to expand where curiosity leads to the next wave of ideas. Destination: let’s find out together.
“All the waves in the ocean seem to add up to deeper and deeper self love and acceptance.” Sylvia Solit
So insightful. ❤️