THE GENTLEMAN PIRATE
A Gentleman Pirate is someone who sails between worlds of order and chaos with both refinement and rebellion. He respects rules as social constructs—useful but not sacred—and instead steers by a phenomenological compass, navigating life through direct experience, presence, and meaning rather than external authority. He is unapologetically pro-human: defending dignity, imagination, and Aliveness in himself and others. His elegance is not conformity but courage—the willingness to stand apart, to live visibly, and to create new possibilities where others only repeat old scripts. The Gentleman Pirate embodies paradox: both rogue and refined, both outlaw and protector, both disruptor of convention and cultivator of deeper human truths.
SACRED
REBELLION
ELEGANT
DEVOTION
LIVING
IN THE
SHIVER
LIVING as ART
I remember when someone asked me, “What will you be when you grow up?” and I answered with fire in my chest, “A pirate captain, a monk, and an explorer of hidden worlds."
Then came the classrooms, the protocols, the job titles. I didn't trade in my compass, though. I became an English teacher at an all-boys Jesuit high school where I learned about the badassery of Jesuit teachings in classrooms, basketball courts, and Kairos retreats. Then I became a world-class Haberdasher where I built people and wardrobes for top-tier CEOs who acted and lived as wealthy Gentleman Pirates themselves. Then I became a Doctoral student who studied the "purest form of insubordination" also known as curiosity. And finally, I became an budding entrepreneur, and it took me 8 years of trial and error before I understood the work and dedication it takes (i.e., a commitment to iteration) to build a profitable business from the ground up. In other words, I learned the hard way that the life of a Gentleman Pirate ain't easy...and...it's worth it.
As a result, I've lived a life intentionally confronting my own map of sea monsters, saints, and mystery.
And now I want to invite guys who also want to live as Gentlemen Pirates in service to and in community with and for others.
I mean, what if there was a way to build a life meant to be navigated like open water — lived as art, studied through experience, steered by you as captain and Aliveness as compass?
Well, KAIROS aims at connecting men to their Holy Work.
KAIROS is a Harbor for gentleman pirates — a Jesuit-inspired outpost at the edge of the known maps of being human men.
Here you get to learn and live with elegance and defiance, in devotion to Aliveness itself, with the wind, the questions, and the courage to sail upon the waters of Vibrant being.
More About KAIROS
KAIROS is an all-guys storytelling container where men get to:
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Build and share stories that matters to them (not your boss, not your mom, not your partner)
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Learn to explore the edges of Aliveness through 1-1 time with the Gentleman Pirate, Six Igsby, Ed.D
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Turn their curiosities into maps/stories to help others navigate their own sense of Vibrancy
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Practice being messy and human in an age where machines are getting weirdly good at everything else
Think of KAIROS as a garage where guys come together to tinker, except instead of fixing cars, we're building stories and conversations that feel like shooting the shit with an old friend, drinking beers with the old man, sitting on your favorite couch, playing ping-pong with a good friend, holding your one-hour-old Godson in your arms, hugging a friend, shaking hands with someone you respect, making the team, playing for a coach who knows how to win well, shooting pool at the bar, etc. etc.
KAIROS
ARCANA (Your Creative Crew)
This group is essentially about establishing traction for what you care about. If you're already doing what you care about, we want to amplify that. And if you're not, we want to support you in finding what you do care about and then grow that.
ITERATION (THE METHOD)
"How do we keep showing up without burning out?"
Spoiler alert: sustainable creativity isn't about grinding until you hate what you love. It's about finding rhythms that actually work with your mind, body, and spirit instead of against them.
Iteration is how we learn to build stories that protect our Vibrancy without destroying ourselves in the process.
And iteration (i.e., falling in love with the reset button) is the method we use to build/uncover our compass of Aliveness.
ATELIER (YOUR STORIES)
The Atelier is your Capstone. It is the finale and snapshot of a chapter in your life as a Gentleman Pirate. It is your Open Podium.
You will be practicing your storytelling over the course of three months leading up to a 10-minute performance as the character you've built slowly over time.
Ateliers are recorded and shared (via audio only) to help inspire all men across the country to connect to and uncover their own Gentleman Pirate.
KAIROS as PODCAST
A Captain and His Compass
Format: Weekly, 45–60 minute podcast (free)
Host: Captain Six (pseudo Jesuit pirate, academically trained in curiosity)
Guests: Male-only, fictional characters
Concept
Captain Six Igsby engages male characters whose stories are too raw, violent, or socially unacceptable for mainstream media. The show is entirely fictional, using archetypes like outlaws, exiles, and societal misfits. Curiosity guides the conversations, blending imaginative storytelling with intellectual rigor. The podcast is free, functioning as a sermon or philosophical meditation on Aliveness.
Companion Book & Fundraiser
Title: “F” School Up the “A”: A Cheat Code for Accessing the Imagination — An Erotic Critique of Education in the Age of AI
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Raw, rebellious critique of schooling in the AI era
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Erotic, poetic, subversive, yet practical insights for reclaiming curiosity
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Book and Fundraiser are for-profit only, and the profits are shared between Six and guests/characters
Unique Selling Points
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Male-only guests playing fictional archetypes
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Raw, unfiltered, imaginative storytelling
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Blend of fiction, philosophy, and scholarly rigor
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Gentleman Pirate philosophy: channel inner storms into Aliveness
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Free podcast with for-profit book/fundraiser ecosystem
Extensions & Impact
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Storytelling events
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Companion book expands on curiosity and critique of schooling
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For-profit ecosystem
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Sparks conversation about learning, violence prevention, AI-era human skills, and cultivating Aliveness
Tone & Experience
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Poetic, provocative, intellectually rigorous
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Not therapy, not redemption arc, not motivational fluff
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Curiosity-led exploration of human complexity through fiction
Revenue & Sustainability
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Podcast is free; book and events generate revenue
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Profits shared between Six and guests (fictional characters)
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Professional, sustainable for-profit endeavor
Atelier is rooted in Holy Work. Atelier is defined as, "a workshop or studio, especially one used by an artist or designer," and it will function as such as well.
The Atelier will be in an audio storytelling format only.
Kairos, then, will be the culmination of these Ateliers exploring the theme of Living the Fourth as a Gentleman Pirate.
Atelier
First, this isn't about single-sex containers. It's about creating an environment that has the texture of "guys being guys" because we're creating a container where you can:
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Fail spectacularly without making it a value negative
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Get genuinely excited about something without having to explain why
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Talk about the stuff that matters while translating it into "teaching" language
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Be competitive AND collaborative without someone taking it personally
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Build things with your hands AND your heart
We're not anti-anyone. We're just pro-creating spaces where specific kinds of magic can happen. And this particular magic happens when guys who want more from life get together and start building.
Why All Guys?
CURIO
Six's Shrine of Brilliant Storytelling
(Ateliers IRL)
The Core
In a world where everything we've known is shifting, storytelling become acts of forgiveness, hope, and love — preserving what's most beautiful about being human while embracing what's most promising about our technological future.
Spill the Water is for anyone who believes that storytelling can be about the evolution of the storyteller, not just sharing information in a way that makes us special.
Spill the Water is about creating a "Hat Store" of ideas where storytelling becomes the path through and around the collective challenges we cannot solve on our own (optimized learning in ecosystems).
It's a place where wisdom and technology kiss.
Spill the Water is how A Church By the Side of the Road intends to leverage presence, AI, and Aliveness to access and experience God in all things.
So, yeah. There ya have it.
Lastly, to end with Six's favorite Jesuit prayer:
"To all that has happened, thank You. To all that will happen, Yes. Amen."