This is a newsletter about my unique perspective on the legal ecosystem, AI & legal technology, and observations about “unicorn jobs.”

What you can expect to learn:

  • Insights into the legal ecosystem. I’ll explain the unspoken rules of the profession that senior lawyers will never discuss in articles or presentations. If you want to navigate this industry you have to know what these rules are.

  • Commentary on technology & AI. Generative AI is the hot topic these days, but technology has impacted on legal for decades. I’ll use stories from my experience selling tech to lawyers to help explain how I believe AI will make its way through the legal industry.

  • How to become a unicorn. There exist jobs out there where you’re paid well to do meaningful work. It’s not easy to find, though. You need to develop rare, valuable skills (often related to sales) and apply them to a niche that’s growing quickly. I’m lucky enough to have a unicorn job, and I’ll share insights into how I found it.

🔒 For paying subscribers: 

  • Monthly deep dives on key topics. Every month I will release content—articles and courses—designed to provide insights into some area of expertise I have. Previous examples include business development, marketing strategies, and how to use social media to drive sales. See more here.

  • Archives of my old posts. My views evolve over time, so older articles are probably less relevant to my newest ones. Which is why I’ve decided to hide them behind a paywall. My latest thoughts will continue to be available to free subscribers.

  • How much does it cost? $10/month or $100/year. Many subscribers expense this newsletter using their learning, professional development, or training budget.

Reader Reviews:

“I've been reading the usual suspects serving the legal marketplace for a lot of years. With most, it's like going to the dentist. You don't want to but you make yourself do it. Alex's weekly posting is something I actually look forward to. There's a point of view, which I share, and a healthy skepticism without beating you over the head with it.” - CEO, Legal Marketplace Company

“Alex writes thoughtful stuff aimed at early and mid-career lawyers - but it also offers insights which 'seasoned veterans' (like me) can learn lots from. His experience working in law firms + in-house with legal tech has provided him with lots of material to draw upon - and he's just a good story-teller. Sign up, and find out for yourself! “- Law Firm Partner

“Alex's ‘Off the Record’ newsletter is a must-read for anyone who is interested in: (1) contemporary and popular legal topics, (2) navigating life as a law firm associate, (3) CLM (Ironclad in particular), (4) general career insights, and/or (5) the intersection of law and humor, which usually results in great memes. I subscribe for a number of reasons I've listed above, and I enjoy each and every one. Alex is wise beyond his years. Thanks Alex!” - Head of Legal, Tech Company

“Alex has a unique ability to uncover the unspoken truths of a career in law. What it taught him about the practice of law and about himself - which we can all learn from - makes Off The Record a valuable read.” -CEO, Legal Tech Company

Subscribe to Off The Record

A newsletter about my journey from law to legal tech


Left the law to sell tech to lawyers