Ryan Rumsey

What they show

A content hub with a blog archive, newsletter, and resource recommendations, positioned around advising creative entrepreneurs whose service businesses have stalled. He's explicit that he advises rather than coaches. The site recently announced that his content now lives across three brands, each for a different audience: Second Wave Dive (service-business founders), CDO School (design leaders aiming for the executive level), and Jump Ship. He mentions hosting an unconference and combined subscribers above 10,000.

Why it works at this level

Most post-executive sites try to serve every audience from one page. Ryan split them, and the split is itself a leadership decision worth noticing: CDO School speaks to the reader of this collection directly, while the main site speaks to founders. The 'advise, not coach' line is a small act of positioning that a lot of ex-executives skip. And the operating-executive background (leading design strategy at EA and Apple) is used as authority for the executive-track content rather than as a portfolio, which is the right use of it.

What to steal

If you have two clearly different audiences, consider two front doors rather than one compromised homepage. Say precisely what kind of help you give (advice, coaching, consulting, fractional); the word choice is the positioning. If you're aiming at CDO-level roles, CDO School is worth reading before you build your own site.

What I'd change

One thing I'd push on. Every site here is good; this is the note I'd send the author.

The three-brand structure makes the executive credentials hard to find from the main site, and a first-time visitor can't tell which door to walk through. A single 'start here' that routes by reader would fix it.