What the Stan x Steven Bartlett Deal Signals for the Creator Economy

We’re halfway through the year, and I’m switching things up.

I realized I’ve been experimenting with a lot this year — office hours, new tools, shifting my services, writing more consistently, building in public. And while I’ve been sharing bits and pieces across channels, I wanted to bring it all back here — in one place.

So I’m switching this newsletter to a biweekly digest.

I’m more excited than ever to be creating long-form content — interviews, essays, deep dives, playbooks.  But I don’t want to feel the pressure to send a weekly newsletter just to fill up some space. My dream is to create something that feels more like a magazine — something you can browse, click into, and come back to when you’re ready.

In this edition, you’ll find several pieces of long-form articles I’ve created over the past few weeks, including interviews with Lex Roman and Michael Kauffman plus a closer look at my content system.

Quick PSA! Before I get into this week’s newsletter, I wanted to share that I have an opening for a client starting in July. I’d love to work with a founder or growing startup as a fractional Head of Content. I’d especially love to partner with anyone building in the creator economy, AI, or solo business space. DM me or hit reply if that’s you!

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I recently sat down with Lex Roman, founder of Journalists Pay Themselves, and someone I consider one of the clearest voices in the paid newsletter space right now.

We talked about:

If you’ve ever thought about going paid (or you’ve tried but felt icky selling it), I think this conversation will reframe a lot for you.

👉 Read the full Q&A here: Q&A with Lex Roman: How to Make Paid Newsletters Work in 2025

I finally wrote down the system I use to stretch one strong idea into a full content stack — think newsletter, social posts, carousels, videos, and more.

This has been the hugest help for me trying to scale as a Business of One. I know I need to be showing up often on these platforms, but it’s tough and exhausting. I wanted to find a way that I could slice one story in different ways and still get the same results!

In the full post, I break down:

If you’re trying to stay consistent but are managing everything on your own, this can be a great place to start.

📓 Read it here: How I Turn 1 Idea Into 8+ Pieces of Content

One of my favorite conversations this year was with Michael Kauffman — the creator behind Catskill Crew and someone who’s taken the idea of a “newsletter business” and completely redefined what that can look like.

It started with a simple local newsletter that quickly turned into an engaged local community. Then into in-person events. And now products like a Catskills-themed Monopoly and eventually a book.

It’s one of the best examples I’ve seen of what Michael calls creative monetization — using your newsletter as a launchpad for something much bigger.

Read the full Q&A here: Q&A with Michael Kauffman, Founder of Catskill Crew

I’m experimenting with Riverside to start recording quick takes — lessons I’m learning, creator Q&As, and behind-the-scenes notes I’d normally share in writing.

My hope is to test adding more voice or video clips directly into these emails and on socials, so you can get a feel for the energy behind the words.

So far, I’m loving the quality (studio-level even with basic gear), the repurposing ability (clips for reels, stories, shorts), the ability to go more in depth with my stories and frameworks.

If you’ve been following me for a while, you know I love watching the intersection of founder-led brands and the creator economy. So when I saw that Steven Bartlett (yes, The Diary of a CEO Steven) had officially become a co-owner and investor in Stan, I basically dropped everything to write about it.

It’s one of the biggest bets I’ve seen embracing the the future of creator entrepreneurs. We’re watching the ownership era of the creator economy begin. I’ve also set up my own Stan store to experiment with the tool - so I’ll be sharing more of my learnings there too.

I shared more of my thoughts here on LinkedIn.

I loved this episode of The Nathan Barry Show. It’s a conversation with Hala Taha, host of Young and Profiting, about how she built a million-dollar business from her podcast. It inspired me so much that I realized I needed to lean into video and podcasting like… yesterday.

They talk about her approach to PSO (Podcast Search Optimization - who knew?!), how to use LinkedIn to grow your show, how to price ad deals and sponsorhips, and so much more.

Thanks for reading — and building alongside me. 👋

If you’re enjoying Creator Diaries, it would mean the world if you shared it with a friend or colleague building their own thing.

— Taylor