My strategy with making and shipping creative work has, generally, involved earning money through business writing (in the form of working independently as a marketing consultant, or in a marketing full time role) and investing it into creative projects.

Projects like Creative Doing, pretty much all my writing online (including Medium), Prologue, The World According to Kanye, Chamath Archive, Revision, etc., were all made possible by my business writing work. In other words, my business writing cross-subsidized all of these creative projects. The lack of financial pressure felt very liberating for each of these projects; however, my next focus is to structure these projects so they can sustain themselves. (I believe I discussed this with Chris Do at The Futur.)

The gatekeepers—publishers, etc.—don’t offer as much distribution support as they used to. They also lost control of their audiences; now, in order to work with them, you need to bring the audience. (The good publishers still offer credibility, production efforts, publicity, etc.)

There were personal reasons, too. I was initially constrained by not knowing the first thing about pitching traditional publishers or distributors, and I hadn’t met any agents, and I could just publish my work on the internet, so it felt easier for me to do it myself—which I did.

In this season of exploration, I’m returning to independently working with companies. Some of my recent projects that have gone live:

• The team at Obello hired me to help them set up their writing and marketing foundation. Tangibly, the project included a blog post to develop thought leadership, a blog post to support their launch from closed beta to general availability, an email to their product waitlist, and the first part of their whitepaper. From a strategy perspective, I delivered through processes beyond AI’s current abilities: identify and decide which deliverables would have a high impact, ask good questions and share creative research to elicit interesting ideas, and edit drafts for development and structure.
• The team at Greptile hired me to salvage an initial draft of a blog post they weren’t sure what to do with. That turned into this post, which sparked a lot of discussion at Hacker News. I’m now working with them on the next post. (I have very limited capacity to work on a per-post basis.)

I’ve always felt enthusiastic about technology (my first blog as a teenager was about tech!), so I’m glad to continue this practice. On the independent front, I’ve worked with organizations like Shopify (here’s a case study, and a deep dive), Flipp (case study), and the City of Toronto (case study). On the full-time front, I’ve worked with Figma (lots of blog posts here), FGX, WorkOS, and Intuit.