OTR, Take 4: Boston - Don't Look Back

"Are you trolling him?"

Hello, hello! Owen here with Take 4 of On the Record and this week's record takes us into some uncharted territory. This morning, I'm spinning Don't Look Back, a towering monument of 70s guitar space rock.

Today I want to talk about how strangely opportunities reveal themselves and how accidental and unexpected alignment can upend carefully thought-through positions.

How often have your found yourself doing something you swore you'd never do again? When I opened McGrannLAW LLC in March 2019, I told my wife that I just wanted to create a cozy boutique firm where I could mostly keep to myself and do my thing. My ambition wasn't just shy of empire building, it was more along the lines of, "I'm just going to till my land, thank you very much."

After nine years in firms of sizes ranging from 20 attorneys to 1600 attorneys, I didn't want to play nicely in the sandbox any longer; I wanted to practice law as I saw fit and didn't want to have to answer to anyone but my customers. I swore to Audra that I had no interest in building the firm large enough to hire an associate, let alone partner with another attorney.

Let's just say my ambitions were more Nick Drake than the brothers Gallagher.

For over three years, that's exactly what I did. Don't mistake me: the firm changed and evolved over those three years, as I had no idea how to run a business at first. (All of my posts about lawyers being bad at business? Those are drawn from hard-won knowledge.)

Then this summer, opportunity presented itself at the dog park. Wendy Witt and I had known each other for a little while. Her law firm coaching work is international, but she happens to live across town here in Pittsburgh, so when she suggested a Zoom meeting to talk about some of the things I'd been working on, I suggested that we meet at the dog park instead.

It turned out that our thinking on the business of law and the effect we wanted to have on attorney wellbeing were so aligned as to be the same line. Our equations looked different at first, but simplified to the same thing.

I was excited after meeting with her because I felt I must be on to something worthwhile if someone as smart and prominent as Wendy not only didn't think I was crazy (or at least not crazy for that reason) but that I got the impression she was excited about some of the ideas too.

Fast forward six weeks and we were discussing what it might look like to open a firm together focused on estates – estate administration, planning, and elder law. I had some hesitation, just the residual "I'm a lone wolf" nonsense that had been in my head since I opened my firm. Then I asked Wendy what was the most important thing she was looking for with this potential firm.


And I was in. We're going to do some really interesting things with Purely Estates Law Group – which we hope to officially launch in the next week or so – but suffice it to say it's a firm that is designed from the ground up to enable attorneys to be joyful in our work. We're out to prove it can be done, first locally, and then at scale.

Wendy gave me today's record "so that [I] could learn what good music is." Her husband, Joe, asked whether she was trolling me. LOL. On the one hand, I hope she is: it's good to have some play in a business partnership. On the other hand, I know she's not.

Because when I listen to Don't Look Back I hear joyful music. I hear a band having fun – a bunch of kids from MIT jamming out. I mean, look at the cover!

It's a guitar-shaped spaceship! It's a perfect gift: emblematic of something the gift-giver cares about and conveying hope for a shared endeavor.

For those of you who know Wendy, none of this will be surprising to you. This is who she is. I wish you could listen in on our planning meetings to get a sense for how much fun she has building things. I'm excited to get Purely Estates Law Group up and running. It always takes longer than you think it's going to, but we're nearly at an MVP stage.

A final word: Wendy spent the better part of the last week in the ICU. I have spent far more time in the SICU and ICU than I care to admit, and I know just how it wears on your. She's home now, and recovering, but if you know her (and even if you don't!), reach out and send her a note. I know how much that meant to me when I was recovering.

Listen to Boston's Don't Look Back on Tidal or Spotify.

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