I’m Starting a Substack Newsletter, Here’s Why

My thoughts on the Creator Economy and the next iteration of my writing

Chris Jennings
3 min readApr 5, 2021


The Iterate Newsletter logo, designed by yours truly

Hello! I’m starting a newsletter on Substack, and here’s why.

The Creator Economy

I’ve worked in the “creator economy” for a long time. When I was a host and producer at CreativeLive, I worked with world-class instructors every day. Ambitious people who’ve built their businesses around the idea of creating helpful content that their audiences were willing and eager to pay for. This was a new world that I hadn’t been exposed to before. And in the early days of 2013, it really was the dawn of the Creator Economy.

These days, I spend most of my working hours helping YouTubers and Podcasters create content that brands want to be associated with. When this is done correctly, it’s a beautiful thing! Clever pieces of content make the audience laugh, learn, and hopefully show them a new product or service that will actually improve their life. Creators get paid for their efforts, and brands see a return on their marketing investment (whether that’s signups, views, clicks, etc.)

So what does this have to do with my newsletter?


I’ve been admiring what Substack has been doing over the past few years, and just recently they secured another round of funding. It’s clear that this hyper-engaged, loyal fan business model isn’t going anywhere. People are hungry to connect directly with writers and give them precious space in their inboxes. Now is the time for me to apply my knowledge in this space and share it through their platform.

My Previous Newsletters

I’ve had various levels of success with newsletters and e-mail marketing in the past. Probably most notably was my Darebnb newsletter that shared useful information with people who were getting started in the sharing economy on services like Airbnb. We had nearly 1,000 subscribers at our peak. Then local regulations got in the way of my Airbnb hosting and I decided to pivot away from the project despite continuing to see interest in my comprehensive e-book.


So today, I’m announcing Iterate. Iterate will be my newsletter that shares my knowledge, opinions, questions, and concerns about the world of technology. The name does carry some double meaning. I wanted something that was vague enough to go in several directions, but still, lend itself to the heart of what I’ll be writing about. Writing is a craft where we iterate each day. Technology is released in iterations, hopefully, each one improves on the previous version in some way.

Hell, we all are new iterations of our past selves each and every day. Deep stuff right? In all seriousness, this is also an iteration of my previous newsletter efforts. I’ve learned a lot over the years, and I do feel like Substack is the perfect platform for me to connect with readers from Medium, former Silicon Valley colleagues, coaching clients, old Darebnb fans, and everyone in between.

What This Means

You’ll still see me posting on Medium from time to time. And I do intend to keep the “How To Use Technology” Medium publication running. Although I may be looking for some contributors to help me out (drop me a line if you’re interested).

So please, if you’ve ever found any of my writing interesting at all. If our paths have crossed in any capacity over the years. If you just want to take a closer look at the way we interact with technology and digital culture, please sign up for Iterate.

It’s 100% free, and I think you’re going to learn a lot along the way. The first edition goes out tomorrow and you can expect (at least) weekly updates as the project gets off the ground.

Again, sign up here if you’d like.





Chris Jennings

I write about the intersection of technology, productivity, and mindfulness. See more of my work at iterate.substack.com