My Business Model

I write, tweet, podcast, teach, invest, and speak. Here’s how my media engine fits together.

In the image below, dark blue lines represent the current flywheel while dotted blue ones represent the future one.


1. Twitter

Everything starts here. The vast majority of people find me on Twitter. It’s the town square of the Internet and an always-on conference where I make friends, grow my audience, and share what’s on my mind.

2. Essays

Long-form writing is my favorite art form. It’s the hardest thing I do, but also the most rewarding. In the past year, I’ve written four essays longer than 10,000 words. Combined, they’ve been read more than 250,000 times and transformed my worldview.

3. Podcasts

I have two podcasts: (1) The North Star Podcast where I interview interesting people, and (2) The Write of Passage Podcast where I talk about the basics of online writing. Through The North Star, I get to learn in public and meet tons of incredible people.

4. YouTube

My channel is small, but growing. I’ve been hosting workshops with my favorite people on Twitter (including Sahil Lavignia, Matthew Kobach, and Nick Maggiulli). Like the podcasts, it’s a way to learn in public and collaborate with outstanding writers.

5. Email Subscribers

Email is the linchpin of my professional life. I send out two weekly newsletters: Monday Musings and Friday Finds. One is a collection of the coolest things I learned every week, and in the other, I share my favorite links.

6. Online Courses

Write of Passage — my 5-week online writing course — is my main revenue stream. In the past year, I’ve taught more than 500 people to think better and accelerate their career by writing online. The business is one year old, and I own 100% of it.

I also have two other online courses.

∙ Write of Passage Summer Camp is a joint venture with Ana Lorena Fabrega. We built it for talented and ambitious 9-11-year-olds.

How to Crush it on Twitter outlines my strategy getting the most from this platform.

7. Angel Investing

I invest in companies focused on creators, productivity, and the future of education. I’ve made a few angel investments, but have only announced my investment in Primer — a homeschooling-focused education company.

8. Book

These next two are about the future. I’m thinking about my first book, which will probably be about writing online and becoming a citizen of the Internet. I’m already in talks with agents, editors, and traditional New York City publishers. The plan is still unfolding.

9. Personal Subscription

I want every incentive to learn faster and share high-quality ideas you won’t find anywhere else. Launching a subscription is the best way to do that. I’ll probably start with exclusive videos and podcasts, but like the book, I haven’t finalized a plan.

Ultimately, I want to build a collection of Audience-First Products. They’ll be software-based and focused on writing, productivity, and education. Writing online is my go-to strategy for finding customers, companies, and entrepreneurs.