top of page

The Problem with Lawyers...

Is that we take ourselves too seriously and we know everything. In my Virginia personal injury practice, I refuse to represent other lawyers. It is impossible to learn what you already “know” and most lawyers “know” enough about personal injury law to be terrible clients.

In fact, most lawyers “know” enough about everything to be terrible clients in just about any business. Either that, or we’re too ego driven to let on that we don’t know by asking someone who actually does know.

So I went searching for answers outside the law.

The Time Freedom Podcast is my pet project to get my own questions answered. Because I don’t believe I’m the only one who has them. I’m just the only one dumb enough to open my mouth and ask.

Playing a Different Game.


I ran marathons for a while. Beating my head against the wall and my feet against the pavement for 20 miles on a Saturday morning. Eyes glued to my GPS watch. Hoping to improve my marathon time by a few minutes a year despite the fact that I was never (ever) going to win one of these races.

Then, one day I read about ultramarathons. The runs got longer, yes. But they also got more fun. Much more fun. The terrain shifts. The same trail is different each season. And the community is amazing.


All of a sudden, I’d discovered a different game. One that was more about the experience (and the bourbon at the finish line) than about your finish time.

Which got me thinking about where else I could find different games.

At my first law job, I worked at a general practice firm.  If a client could pay us, we did it.  And we usually did it by the hour. 


I had to work the day before Thanksgiving.  Not for any good reason.  We weren't getting ready for trial.  We didn't have a brief due.  Just because I was new, didn't have any accumulated PTO, and the office was "open."  That day, the phone didn't ring.  Email didn't ping.  No clients walked in.  And my boss didn't come in either.

I quit that job within the month for a Plaintiff's contingency fee practice.  No more trading dollars for hours.  No more working on things that weren't productive in order to meet some billing requirement.  

And I started figuring out that the way to make more money in this practice wasn't to work more hours.  At least not on the legal stuff.  The way to make more money is to market in a way that attracts larger cases and to efficiently run those cases.  No wasted effort.



Before You Interpret This as a Failed Lawyer's Pivot...

Let me add some bona fides: 

I graduated from William & Mary School of Law in 2008 and stayed at my second firm for eleven years, ultimately becoming a named partner.  In 2019, I left that firm to partner with my dad.  In the first three years, we doubled the revenue of the firm (and quadrupled the revenue of the personal injury section).  

In the past few years, I've tried a medical malpractice case to a $3.4M verdict (2019), been involved in the largest ever settlement for the death of a child in Virginia (2020), and won a $4.3M verdict which included a Virginia record-tying $1M in punitive damages for drunk driving (2022).


At some point, I started to wonder... Is there a way to make dollars without trading my hours at all?

That question brought my to the world of real estate investing, syndications, and ultimately my own short term rental business.  This picture is the view from the back porch of my beach house.

The thing is that none of this stuff is discussed in law school, around the courthouse, or in CLEs.  There is very little lifestyle and financial advice pitched to lawyers (outside of the hawks who slide into your LinkedIn DMs once a week).  I'm here to change that for you.

bottom of page