Cheers and welcome to 2026!
As we head into a new year, there’s a familiar pressure to optimize everything: bigger goals, grandiose ambition, lofty promises, and perhaps faster execution. This conversation with my dear friend, Jeff Ragovin, is a clear reminder that the work that lasts for posterity doesn’t start with perfection. It begins with people.
Jeff—founder, builder, storyteller, and the creative force behind his new show, Bounty Uncharted—joined me for a wide-ranging conversation about building in public, letting go of ego, and creating experiences that live far beyond the moment.
It’s vulnerability and self-awareness on steroids from one of the best in the business. From launching a show on the open ocean to cultivating community around a dinner table, Jeff’s work sits at the intersection of ambition and humanity. Or as we say on the show, doing good while doing well.
Bounty Uncharted is a cinematic storytelling series where fishing, food, and human connection collide. It celebrates the people, our cherished waterways, and the shared moments that bring community to life.
This episode feels like the right way to kick off 2026: humble yet hungry, curious, and deeply intentional.
5 Takeaways to Carry Forward
1. Start Before You’re Ready
What we talked about:
Jeff didn’t wait to become an expert filmmaker before launching Bounty Uncharted. He learned on the fly by doing, whether on the water, in the edit room, or in real-time with his guests.
Why it matters:
Many founders stall because they’re chasing readiness. In reality, readiness is earned through motion.
‘If you're not embarrassed by the first version of your product, you've launched too late.’ — Reid Hoffman
Real-world parallel:
Airbnb’s first listings were far from polished. The founders learned what mattered by shipping early and iterating fast, way before they became the ubiquitous brand we know.
How to implement:
Identify the minimum viable product (MVP) of the idea you’ve been sitting on
Commit to one imperfect launch in Q1
Treat feedback as fuel, not failure
2. Build Around People, Not Just Outcomes
What we talked about:
Whether it’s Jeff’s closed-door dinner series (10-15 people max), The Digital Fork, or a day at sea, Jeff designs experiences where the human connection is the value, not an afterthought.
Why it matters:
Community compounds. Transactions don’t.
Real-world parallel:
Patagonia didn’t build loyalty by chasing growth alone; they built it by standing for something (protecting the environment) and inviting customers into a shared mission.
How to implement:
Ask: Where do people naturally gather around my work?
Invest in one intimate, high-touch experience (dinner, roundtable, small event)
Optimize for depth over reach
3. Let Go of Ego, Keep the Vision
What we talked about:
Jeff’s original idea for Bounty Uncharted evolved as the right stories showed up. Instead of forcing the concept, he let it breathe.
Why it matters:
Rigidity kills resonance. Flexibility strengthens it.
Real-world parallel:
Slack started as an internal tool for a gaming company. The founders paid attention when the tool, not the game, became the thing people loved.
How to implement:
Revisit your original vision and ask what’s changed
Listen closely to what’s working unexpectedly
Be willing to pivot without abandoning your core values
4. Treat Creative Work Like a Business and a Business Like a Craft
What we talked about:
Producing a show on the ocean requires systems, teams, and contingency planning, but also trust, intuition, and taste.
Why it matters:
Sustainable creativity needs structure. Scalable businesses need soul.
Real-world parallel:
Nike’s success lives at the intersection of operational excellence and cultural storytelling; one doesn’t exist without the other.
How to implement:
Identify where you’re an A-player vs. where you need outside help
Build repeatable systems for the unsexy parts
Protect space for creativity, even as you scale
5. Create Experiences People Will Never Forget
What we talked about:
First tuna catches. Shared meals. Unexpected moments. These aren’t “content,” they’re core memories.
Why it matters:
People don’t remember metrics. They remember how you made them feel.
“I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” - Maya Angelou
Real-world parallel:
Apple Stores became cultural landmarks not because of square footage, but because of how people felt inside them.
How to implement:
Look for moments of “firsts” in your work (first customer win, first launch, first event)
Slow those moments down
Document or label them not just for marketing, but for meaning and understanding. How can you use those moments to clue you into the continued evolution of your work?
A Thought to Carry Into 2026
We’re all building something: companies, communities, creative work, relationships. The question isn’t how big it gets. It’s how deeply it’s felt; depth vs. breadth. Feelings are the connective tissue that binds people together.
As Jeff reminded us, time accelerates. The only real leverage we have is intention: who we invite in and spend time with, what we pay attention to, and whether we choose to start, right now, without asking.
Here’s to a year of building boldly, leading generously, and creating work that stands the test of time.
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🥂Here’s to 2026 🥂 and the work worth doing.
