503: How to build relationships that grow your Substack (with Rob Riker)

How to Write for a Living · Oct 25, 2026 · 59m

Rob Riker has been on my radar for almost a year, popping up in comment sections all over Substack.

This live was the first time we’d ever properly spoken. He’s built coaching businesses on Twitter, watched that platform change under his feet, and rebuilt on Substack around the one skill he’s most passionate about, which is building relationships. The chat was buzzing from start to finish.

What we covered:

- How Rob went from a social skills blog that barely made money to a coaching business that let him quit his nine to five, and why he pulled the offer when Twitter changed.

- Why he thinks…