Small firm lawyers keep telling me they can’t afford the AI tools big firms use. They’re not wrong, I’ve heard vendors literally laugh at affordability concerns. So when I came across Descrybe, a legal research platform with free core features (and paid plans at only $10-20/month), it got my attendtion and I dug deeper. Here’s my post for Law Technology Today.

New study from Thompson Hine: 95% of in-house counsel see little innovation from their law firms. But clients might be part of the problem. When they reward the status quo with an average 7.4% rate increases year after year while claiming innovation is “crucial,” what message are they really sending?

The gap between what clients say they want and what they actually demand reveals a lot. Law firms aren’t going to change much unless and until their clients demand it. Here’s my post for Above the Law.

When we talk about GenAI for the legal profession we frequently focus on the risks. But Comment 8 to Model Rule 1.1 requires us to also the understand the benefits. Sometimes we make AI a little too complicated.

Two fundamental rules: Don’t put client confidences in prompts and check the output for accuracy. Here is my post for Above the Law.

I was recently at a charity benefit reception and dinner. An acquaintance (and I stress acquaintance) came up to me, took one look and out of the blue asked, “you’re retired, aren’t you”? For some reason that question was both galling and irritating. It took me a bit to figure why even though I’m sure the acquaintance didn’t mean any ill will and was just trying to be polite.

The short answer: I may not practice law full time but I’m far from “retired” and the assumption that I am just because I changed careers is disappointing. I’m not going gently into the night.

Do not go gentle into that good night,

Old age should burn and rave at close of day;

Rage, rage against the dying of the light.

Do Not Go Gentle into That Good Night, Dylan Thomas

Perhaps some background is illustrative.

Some Background

As many know, I practiced law full time for over 30 years as an equity partner in a large law firm. Most of that time, I defended companies involved in mass tort litigation. My work took me all over the country and was challenging and cutting edge. It was a wonderful career, and I don’t begrudge any of it.

But long about 2017, I discovered a new interest in writing and speaking about legal technology. It’s no secret why: since I was always on the road practicing my cases near and far, I had to have the best technology to help me do that.

I enjoyed writing about legal tech and in 2017, made the decision to pursue a second career as a legal tech journalist full time. I was frankly ready for the new challenge. I wanted to see if I could achieve success doing something different than practicing law and for which I had no formal training and little experience. I wanted to see if I could do it.

Here’s what my “’retirement” actually looks like.

How’d That Turn Out?

Since then, here’s how it turned out:

  • My blog Techlaw Crossroads is a well-respected and well known legal tech blog.
  • I write regularly for Above the Law, also a well-known and respected legal tech outlet.
  • I write for an ABA publication, Law Technology Today.
  • I am a regular panelist on the Legaltech Week Journalist Roundtable composed of the leading journalists in the community.
  • I’ve won awards for my writing and my contributions to CLE.
  • I am on the faculty of a trial technology training program.
  • I chaired the ABA Law Practice Division composed of over 30,000 members.
  • I co-chaired the ABA TechShow, one of the leading legal technology conferences.
  • I am co-chair of the Kentucky Bar Association Law Practice Management and AI Committees.
  • I host a podcast consisting of interviews of legal tech vendors and movers and shakers.
  • I regularly attend and speak at conferences, trade shows and other legal tech and even standard tech events.

All in all, I think I’ve done pretty well.

A Part Time Hobby?

As for the part time nature of what I do, I have kept track of the hours I actually work on my second career. (Old habits are hard to kill). Last year I worked close to 1800 hours. This year I am on track to work even more. I regularly hit between 1700-1800 hours. That’s pretty close to my billable hour output the last few years I practiced full time.

And while I use the word “work” it’s really not work-work. I love every minute I spend on my new career. It’s a challenge; I wouldn’t trade it for anything.

But one thing it ain’t is retirement and the insinuation that it is strikes me as insulting.

Still Fighting for Every Inch

But the deeper issue isn’t just about hours worked, it’s about assumptions and ageism. The idea that leaving my legal career means I’m just dabbling, not really working hard or trying my best, is what irritated me most about the question.

I reject the notion that when you reach a certain age and decide to do something different, you can’t or won’t contribute meaningfully. That you need to go gracefully out to pasture, endlessly watching TV while thinking about the good old days. That you’re of little value and expected to just slowly fade into the sunset. That’s not living, that’s slow death.

I am not fucking retired

So no, despite what my well-meaning acquaintance assumed, I am not fucking retired. As long as I have life in me, I’m going to pursue my new career, or maybe even my next one, just as hard and as long as I can. Like Coach Tony D’Amato (played by the incomparable Al Pacino) in the movie Any Given Sunday said:

“I know if I’m gonna have any life anymore it’s because I’m still willing to fight and die for that inch — because that’s what living is.” 

Either that, or like Paul Simon, maybe I’m just still crazy after all these years.

A lot of lawyers think AFAs will save them from AI disruption. They’re wrong.

I’ve been using alternative fee arrangements since the 90s, so I’m not anti-AFA. But the current rush to AFAs as a solution to AI’s impact on billable hours misses the point entirely.

The real issue isn’t how we package our fees. It’s that AI is fundamentally changing what legal work looks like and what it’s worth. You can’t just slap a flat fee on the same old work and call it innovation.

Here’s my post for Above the Law.

At its Inspire Conferance, NetDocuments assembled some of legal tech’s sharpest minds to talk about AI’s real impact on legal practice. Zach Abramowitz, Nicola Shaver, Zach Warren, and Jennifer Poon didn’t hold back on the hard questions: Why traditional ROI metrics fail for AI, how ‘AI-first’ firms are disrupting the leverage model, and why many lawyers are still ignoring what’s coming. But we might be just one economic downturn away from widespread AI adoption in law. Here’s my post for Above the Law.

Over the past month I have attended more user conferences than I can count. At every single one of them there are presentations and panel discussions about change management particularly for law firms.

I haven’t practiced law full time for a bit and have kind of lost the need for all this focus on change management. I forgot how hard it is for lawyers, and anyone else to change. I was quick to conclude lawyers are Luddites who are just being obstinate when they resist change. As for me, I was sure I could change in a heartbeat if need be. I don’t need no management.

Continue Reading My Phone, My Pocket and My Problem: Change Is Harder Than We Think

Just back from NetDocuments Inspire conference. In an era of legal tech consolidation and flashy AI promises, NetDocuments CEO Josh Baxter told me: ‘We’re not a rock band.’ Their new AI Profile tool tackles the metadata problem that’s plagued document management for years. But can this understated, specialized approach survive when the market seems headed toward tech WalMarts? 

Here’s my post for Above the Law.

The world of GenAI: get an answer to anything and everything within seconds. No thinking required: just prompt and go. I’m all about technology and the wonders GenAI brings to our world. But sometimes I wonder: at what cost? 

Once a week, on Sundays, I try to have a screenless day. A day where I try to minimize looking at screens, the digital world if you will.

I got the idea from a book I read a few years ago entitled The Revenge of Analog: Real Things and Why They Matter. It was written by a Canadian writer David Sax who focuses on the analog vs digital life, among other things.

Continue Reading Going Analog: Is It Just for Luddites?


Plaintiffs AI firm, EvenUp, just hit a $2 billion valuation after recently raising $150M. 

But here’s what makes this funding round different: it signals that AI for plaintiffs’ lawyers has reached a tipping point.

I first met EvenUp’s co-founder at ILTA in 2023. My initial reaction? Ho-hum. Another demand letter generator.

Then I learned about what EvenUp was also doing: getting and using crowdsourced data from actual PI cases. Which led it from startup to a billion dollar valuation.

As a former defense lawyer, this could matter for both sides of the table.

Here’s my post for Above the Law.