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Where is Substack Headed?

By Kevin O'Keefe on May 10, 2026
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Interesting Tweet Sunday evening from Matt Mullenweg, a co-founder of WordPress.

Really proud to have @TheAnkler on Open Source with @automattic and @benthompson's Passport product, you can apply for the waitlist here: https://t.co/sPliIxzxxU https://t.co/TlaA27nxgc

— Matt Mullenweg (@photomatt) May 11, 2026

Per Emma Roth of The Verge,

“Substack, the once buzzy newsletter platform, is losing a new swath of writers to rival platforms most people haven’t heard of. Just last month, The Ankler, one of Substack’s most popular publications, left for a platform that gives it more control over its site. Others who have departed Substack within the past year voiced similar complaints and cite the platform’s increased focus on social features as well as a pricing model that puts a chokehold on their business.”

The Ankler is a popular high profile revenue generating entertainment site, so perhaps not your typical writer on Substack. Though Substack taking a slice of revenue is concerning to writers who make their living by writing.

But Roth highlights other factors causing concern among users, enough so for some to leave.

  • Feeling they lack control over their site
  • Limits on customization
  • Social interaction being more internal than external
  • Limitation on integrating third-party apps
  • Overly heavy on recommendations
  • Limits on having followers come with you should you migrate from Substack

Piqued my interest when I read the above as earlier this month I tried Substack for a few posts on the platform. I wanted to see what it was all about. Some bloggers I have a lot of respect for use Substack and there is a community atmosphere that I am always interested in from back in the AOL and early blogging days.

I didn’t have that enjoyable an experience. I had some quirky problems in writing and sharing images. It could have been totally me with the rest of the world having a great experience. I’ll also acknowledge I am the founder of a managed WordPress platform for the law. I’ll be the first to be accused of being biased, and I’ll be the last to spend a lot of time learning how to use the platform.

My conclusion though was that Substack was headed in a social media direction emphasis versus a publishing platform emphasis.

No doubt you neeed you need a publishing solution to write and generate some sort of a community. But if you get distracted with a heavy investment in your company to grow a social network, you can lose your roots in a publishing solution for newsletters.

WordPress is not the only publishing solution in the world. The Ankler moved to an open source platform called Passport, which is built in partnership with Automattic, the company behind WordPress.com. But the mission of Mullenweg and cofounder Mike Little remains strong — to democratize publishing.

I wish Substack, and its writers well. But you have to be careful with investors and possible buyers detracting from publishing first.

Photo of Kevin O'Keefe Kevin O'Keefe

I am a trial lawyer, turned legal tech entrepreneur, now leading the largest community of legal publishers in the world at LexBlog, Inc.

I am a lawyer of 39 years. Wanting to be a lawyer since I was a kid, I have loved…

I am a trial lawyer, turned legal tech entrepreneur, now leading the largest community of legal publishers in the world at LexBlog, Inc.

I am a lawyer of 39 years. Wanting to be a lawyer since I was a kid, I have loved almost every minute of it.

I practiced as a trial lawyer in rural Wisconsin for 17 years, representing plaintiffs, whether they were injury victims and their family members or small businesses.

In the mid-nineties, I discovered the Internet in the form of AOL. I began helping people by answering questions on AOL message boards and leading AOL’s legal community.

I later started my own listservs and message boards to help people on personal injury, medical malpractice, workers compensation and plaintiff’s employment law matters. Though we were green to technology and the Internet, USA Today said if my firm “didn’t stop what we were doing, we would give lawyers a good name.”

In 1999, I closed my law firm and we moved, as a family of seven, to Seattle to start my first company. Prairielaw.com was a virtual law community of people helping people, a sort of AOL on the law, featuring message boards, articles, chats, listervs and ask-a-lawyer.

Prairielaw.com was sold to LexisNexis, where it was incorporated into Martindale-Hubbell’s lawyers.com.

After a stint as VP of Business Development at LexisNexis, I founded LexBlog out of my garage in 2004 (no affiliation with LexisNexis).

Knowing lawyers get their best work from relationships and a strong word of mouth reputation, and not promoting themselves, I saw blogging as a perfect way for lawyers to build relationships and a reputation.

When I could not find someone to help me with my own blog, I started a company to provide what I needed. Strategy, professional design, platform, coaching, SEO, marketing and free ongoing support.

As a result of the outstanding work of my team of twenty and my blogging, the LexBlog community has grown to a community of over 30,000 legal professionals, world-wide.

Publishing my blog, Real Lawyers, now in its 18th year, I share information, news, and commentary to help legal professionals looking to network online, whether it be via blogging or other social media.

Blogging also enables me to think through my ideas – out loud and in an engaging fashion.

In addition to my blog, I liberally share others’ insight on Twitter. Feel free to engage me there as well on LinkedIn and Facebook.

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  • Posted in:
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