September 25, 2025
For this week’s episode of the Real Lawyers podcast, Kevin spoke with Stephen Rosenberg, one of the country’s top ERISA and insurance litigation attorneys and author of the Boston ERISA & Insurance Litigation Blog. With nearly three decades of trial, arbitration and class action experience, Stephen has also built one of the most respected voices in his field through consistent publishing.
In the conversation, he shares how blogging opened doors in what was once a closed market, why publishing still creates opportunities in a world dominated by “content marketing,” how blogs can evolve into secondary law and what young lawyers should be doing to stand out in the age of AI.
Watch the Conversation
Listen to the Podcast
Episode Outline
- 00:01 – Introducing Stephen Rosenberg and his background in ERISA litigation
- 01:20 – Discovering blogging in the mid-2000s and how it began his publishing journey
- 04:20 – Early experiences writing articles and the importance of publishing before the blog era
- 07:40 – Blogging as a way to break into a closed practice area and build credibility
- 09:00 – How referrals and reputation connect directly to consistent publishing
- 10:40 – Shifts in blog focus over time, from case updates to broader issues and lessons learned
- 12:30 – Why chasing pageviews and analytics misses the point of legal publishing
- 14:50 – Real cases and seven-figure results that came directly from blogging
- 20:15 – On citing and crediting others as part of the conversation in law
- 23:30 – Blogging as secondary law and the potential for citation in briefs and decisions
- 29:50 – Advice to young lawyers on carving out a niche in the AI era
- 34:10 – How blogging shows value, builds expertise and opens career opportunities
Key Takeaways
- Blogging remains one of the most effective ways for lawyers to establish credibility and generate work
- Publishing allowed Stephen to break into ERISA litigation despite being an outsider in a closed market
- Referrals often hinge on credibility, and consistent writing makes both referrers and clients confident
- Blogs contribute to secondary law by providing analysis, commentary and frameworks where published case law is limited
- Young lawyers should use publishing to build expertise in niches, especially as AI changes traditional entry-level work