Welcome to Creator Capitalist Conversations, a mini-series spotlighting real-life legends who have rejected traditional career paths and built lives around what makes them different.
In these episodes, you’ll learn:
How each guest walked away from “success” as defined by others and started designing a career of their own
The mindset shifts, hard decisions, and capital-building moves that turned their “different” into leverage
Tactical frameworks, earned secrets, and uncommon strategies for creating a life no job can offer you
These are stories of people who didn’t wait to get picked. They picked themselves—and started building careers that pay them to be radically them.
Because the best way to become a Creator Capitalist…
…is to study the ones who’ve already leaped.
ARRRRRRRRR!!!!!
Dear Friend, Subscriber, and Category Pirate,
Carylyne Chan started her career at age 14—not from comfort, but from necessity.
She didn’t wait for stability. She created it. While others chased credentials and climbed ladders, Carylyne launched startups, scaled brands, and created capital across AI, blockchain, and consumer brands.
She’s not just a founder, advisor, and investor who bet on herself.
She’s the person others call when they’re finally ready to do the same.
This conversation is about the moment you realize you’ve outgrown the life you’re in.
In this episode of the Creator Capitalist series, Carylyne shares how she designed a life full of agency—how she helps others make the leap—and why staying too long in the wrong place is often the real risk.
She learned something most people never do:
Quitting isn’t failure.
It’s a high-agency decision when it’s made with clarity.
“If you have that feeling that things should change… then you probably already know there’s something different out there.” — Carylyne Chan
It’s about knowing when you’re done—and what to do next.
Creator Capitalists don’t just build careers.
They don’t cling to jobs that look good on LinkedIn. They don’t let others define their idea of “success.” They let go of what no longer fits—and create a career no one else can.
Most people think quitting is risky.
But what if the real risk is staying stuck in a life that isn’t yours?
Here’s what's waiting for you inside:
00:42 – The Art of Knowing When You’re Done: What quitting actually looks like and how to tell when your “successful” job is secretly keeping you small
05:30 – Calm in the Chaos: How surviving personal crisis shaped Carylyne’s greatest professional asset and why emotional intelligence is a real superpower
13:10 – Scarcity vs. Self-Belief: The mindset that keeps people stuck and how to trade fear for clarity before you make the leap
24:45 – Building Around Curiosity: How Carylyne built a career from curiosity, not conformity, to create financial, intellectual, and emotional capital
34:00 – Behind-the-Scenes of the Leap: The mindset reframe that helped her friends finally quit—and how to know when your moment has come
This episode doesn’t give you a checklist.
It gives you permission—and a very real look at what it takes to bet on yourself.
To connect with Carylyne
Arrrrrr,
Category Pirates 🏴☠️
P.S. — Quitting isn’t easy. But it might be the smartest move you’ll ever make.
Carylyne’s story is proof that the most courageous move isn’t staying. It’s walking away with a plan—and building something that fits you better than any offer ever could. Clarity comes from action, which means the real risk isn’t leaving.
It’s staying stuck.
If you’ve felt that itch…
If you’re playing out a career that used to work—but doesn’t anymore…
The Creator Capitalist course shows you how to make the leap, find your superpower, and build a career that pays you to be you.
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