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Season 2, episode 19 is here!
In this conversation,
opens up about the business behind his creative work, the systems that keep his community running, and his growing obsession with one powerful idea: trust.Beginning with his early product background to running a 450-member creator community, Jay shares practical advice and personal insights on building a sustainable creator career from the inside out.
What we covered:
Why Jay started over on Substack and what it taught him about empathy, experimentation, and trust
The four key attributes of trust and how they quietly shape every decision your audience makes
How Jay built a high-revenue creator business by focusing on retention, not constant growth
What creators miss when launching communities, and how to fix it with purpose and onboarding
Why going first is one of the most underrated habits for connection, collaboration, and long-term growth
How to brand yourself in an AI-saturated world and become first to mind for a specific idea
The word Jay wants to own in the next phase of his career, and what that says about the future of creator businesses
👉 Make sure to subscribe to Jay’s publication before you go.
Go deeper:
218: What no one tells you about going solo as a writer (with Erica Schneider)
Newsletter ads don’t have to suck: how to add sponsors that feel natural (and pay well)
What’s next?
I’m ready and waiting to support you in the next stages of your creator journey. Here’s a reminder of how I can help:
Start Your Podcast on Substack: A complete course guiding you from concept to launch, based on everything I’ve learned so far during my own podcasting journey. Learn to plan, brand, record, edit, publish, and promote your podcast while building an audience. Perfect for creators eager to share their voice with the world.
The 1K Daily Writing Challenge: Build a consistent habit by writing 1,000 words daily for 30 days. Along the way, you'll get encouraging video prompts, accountability support, and plenty of inspiration to ignite your creative spark. Nail your rhythm. Find your flow. Transform your writing journey forever.
Substack Basics: A video guide showing you exactly how to: set up your first publications; create polished posts from scratch; share, structure, and schedule effectively; and master Notes, CTAs, and growth levers (bonus section: Going Live on Substack).
Sustainable Scalable Social Strategy: This 6-part, online, self-driven course will guide you through the same process I used to develop a strategy for my social media management. When you finish, you’ll have a sustainable social strategy in place that will help you scale your business properly.
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