What if the best law firm in your state wasn’t built by the smartest lawyer… but by the one who learned to let go?

Jay Ruane didn’t want 45 employees. He didn’t want to be a CEO. But somewhere between courtrooms and burnout, he built something bigger — and walked away from the work most lawyers cling to.

He says the key wasn’t money. It was dinner with his kids.

And AI? It’s already replacing hours of legal grunt work in his firm.

So the real question is: what are you still holding onto… that’s holding you back?

Jonathan Hawkins: Wow. That is a powerful story there, man. But it you know, the other point there is no matter how much we plan, life's gonna be thrown us curve balls.

Welcome to the Founding Partner Podcast. Join your host, Jonathan Hawkins, as we explore the fascinating stories of successful law firm founders. We'll uncover their beginnings, triumph over challenges, and practice growth. Whether you aspire to launch your own firm, have an entrepreneurial spirit, or are just curious about the legal business, you're in the right place.

Let's dive in.

Jonathan Hawkins: Welcome to Founding Partner podcast. I'm your host, Jonathan Hawkins. This is a podcast where I get to interview law firm owners, so I can learn about their past successes and maybe mistakes too and you get to listen and hopefully learn as well. Real excited about today's guest. This is somebody that I have been, following from afar for many many years, but just now, actually got to meet today.

Jay Ruane: Sure. So thank you for having me you know, I've actually listened to your podcast for a while too, so it's cool to finally make the connection and talking about my successes, I think we're mainly gonna focus on my failures because I am an open book when it comes to those. I think that's where we learn the most.

Anybody can brag but if you can, you know, unveil where you went wrong, I think that's where we can all learn to be better in trial work in representing clients and also in scaling our firms.

But, you know, I've been a criminal defense lawyer now for nearly 28 years, which is mind blowing to say that. I never thought I was gonna last this long.

And so I would go, you know, I was single. I had a dog. That was my only responsibility. I would go to the local Borders bookstore and see what new business books were out, and I would buy a business book or two, and a couple business magazines every week. And that was how I learned how to do all this stuff. And so that's me.

Jonathan Hawkins: Yeah, I mean, definitely I wanna talk about that I remember you know, way back when there's the Bible, what is it, Doomberg or whatever that,

Jay Ruane: which I never read. I bought my Amazon card, tells me that I bought it. I can't find it and I don't ever remember reading it.

I mean.

Jay Ruane: There was nothing in law. There was nothing in law. I mean, well, that's not true. I know. I read, John Morgan's book years ago. and I was really impressed with that. And, I remember eating, Ferrazzi's never eat alone, because I knew, you know, back then there it wasn't as big as, reliance on digital. So I read that book that, and I read Seth Godin's Purple Cow and I was like this is how we have to do it. We have to be different. And then, you know, I was lucky enough to be pointed in the direction of The niche of DUI defense within criminal law and those are clients who tend to have more money, tend to have higher stakes in their cases.

Jonathan Hawkins: You know, sometimes it's the constraints that actually allow you to grow the way you should. But you know like I said I've been following you and your stuff and one thing that I get a strong sense about you is sort of you, you're a lifelong learner. And I could see where once you sort of figured out the DUI stuff you're like I gotta go figure out something new to learn. But let's talk about your firm for a second. So, you know, you're, my understanding is you got the biggest criminal defense firm in the state of Connecticut. How many lawyers do you have now?

Jay Ruane: I think we're 12 now. We had somebody who thought we thought was gonna pass the bar, didn't, she's gonna take it again this summer. So that'll take us to to 13.

If you get arrested, you don't want to have been arrested, you're not gonna find the money for something.

I mean, I've had plenty of clients who've been like, well, I just took a vacation. I don't have the money to pay you. I'm like, well, what are you talking about? I'm the one who's keeping you outta jail. And they're like, right, but I wanted a vacation. Nobody wants to be talking to me and so that's difficult. So you have to build in I mean, right now I think I've got nearly $700,000 of accounts receivable. Now I have a team that I've put in place that to make sure that we track it.

That's one of my biggest mistakes was not putting that team into place sooner. But, you know, between being, needing to get paid upfront. Needing to have a lawyer do the majority of the work, I think that's one of the hardest parts of scaling a criminal practice.

Jay Ruane: Well, yeah, I mean the criminal defense bar tracks the most dysfunctional lawyers for the most part. I mean, you know, I can name right now off the top of my head, a half a dozen lawyers who flamed out because of you know, they, I guess you could say they clo flew too close to the sun, right? They were partaking in some of the substances that maybe their clients were dealing 'em, they had monetary issues. They just were sort of living by the seat of their pants. And unfortunately, because criminal is lawyer dependent, you can survive. It's just a true solo with a cell phone and hustle and scrape and make enough to you know, put food on your plate and pay your bills every week.

Jonathan Hawkins: And so, you know, lot, lots of elements go into scaling a firm, but, you know, I guess one element, you gotta get cases, you gotta be able to get the work and then the other is you gotta, you gotta go get the people, to service the cases. So, you know, how have you sort of figured out both of those?

Jay Ruane: So I started, so I when I hung my shingle, my father had another firm with one other partner they had one associate, right? And when I quit my job, I walked into his office and I said, Hey, I just quit. And he goes, good luck with that. I don't have any work for you. I'm scraping by myself. But he and the other guys in his office, they actually had another solo who was sharing space.

They were like, we got an empty office in a broken desk. You wanna use that? Go for it.

Other lawyers recognize that knowledge. I mean, I'll tell you, I gave a speech probably two years into the practice of law, on how to defend A DUI case. 'cause I had started to make a name for myself and I opened the speech to, it was to the statewide Criminal Defense Lawyers Organization. And I opened the speech with it. So great to see all of these great names. And I started naming people in the audience, and I said, every single one of you wouldn't give me a job 18 months ago. And now you're here learning from me boy, who made a big mistake, right? and they all laughed. And but, but I just wanted to call 'em out for it. Like, none of you gave me a chance. I sent, I literally, I went through the criminal Defense Lawyer's directory, and I said, every single one, I said, you know, Jim Ruane's son, I'm looking for a job. I will work hard, give me a chance. And I got dozens of rejection letters and so I just had to do it on my own.

So, you know, you put up this website, you know, you said it's trash, but it probably was the only one for a criminal defense firm up at the time. So, and then pay-per-click was super cheap, So, you probably got it's you know, it's almost like heroin. You're probably getting a lot of leads outta that for cheap. But then the game changed when everybody started coming in. So, you know, this happens over and over and over in any business where you get in early and you ride it, you know, you really enjoy it, but eventually it's sort of the steam runs out. So how did you sort of maneuver out of that over time?

So there's a significant chunk of arrestees who will never, ever become clients to anybody. But last year in Connecticut, there was only like 5,000 DUI arrests. and so not only was competition increasing on the digital atmosphere, because people started finding that, oh, I could put up a website and get some business out of it, but the available caseload, was dropping, at the same time.

But you know, last, I think last week we created a million words of content for our website. So we're still growing and pushing.

Jonathan Hawkins: So I want to talk, I wanna talk about that for sure. Maybe now is a good time. So, so you've got a podcast with Seth Price called The Law Firm Blueprint, which is really, really, really enjoy that one. And one of the things I really like about it is you guys go on there and maybe you each have a few questions and you just sorta spitball with each other live.

Jay Ruane: Literally like we text each other three topics and that's it. Like, it's no pre, it's, there's live without a net, basically.

Jonathan Hawkins: And it, is really good. So anybody out there who's not following that needs to go follow that 'cause it, it's really good. And the other thing is, you know, I've learned a lot about you,

Jay Ruane: Uh oh.

Jonathan Hawkins: just from listening, so, which is cool. And so, you know, one of the things on there, you know, there's a few things I wanna talk about, but one of them is your, output of content.

And then, you know, they're in the queue. How did you get to that place? You know, somebody like me or anybody else who's like, okay, I want to get there. how do you get there?

So you could see the progression. I had that bias towards action. So I've gotten better at doing things. If someone else were to start now, they would not have had that time to figure out how to do it. And now they'd have to spend so much more money on bringing in a high-end editor and, you know, that type of thing and so I think it's, my bias towards action is I jump at things early in the process, maybe too early, but by doing that I can fail or at least look ugly, and it's still somewhat acceptable and because it's new. I mean, we put out, I, put out a podcast during COVID 'cause we had nothing else going on.

Jonathan Hawkins: You know, it's, I mean, you know this, but most lawyers are sort of scared of making a mistake, scared of looking stupid. So they just do nothing you know, it reminds me of, I don't know, Mr. Beast, whatever, his in Jimmy, whatever his name is, where he basically said First hundred are gonna suck. you just gotta know first. hundred are gonna suck, and you just get a little bit better on each one. Just gotta start somewhere.

Jonathan Hawkins: That's a great point. So you've done, you've tried a lot of stuff. I mean, you've tried a lot of stuff. some work,

Jay Ruane: radio, billboards, digital. I mean, I've done it all.

Jonathan Hawkins: So, so, and I know things change over time, but what, and without giving us your secrets what's sort of your current sort of stack, what is it that's really generating for you?

Jonathan Hawkins: Wow. Wow. That's awesome. So, okay, so I wanna shift, so we've talked a little about, you know, scaling their firm, getting the clients. The other part is, you know, building the team. And so, you know, how do you keep folks happy? and I mean, both staff And attorneys and, and I asked that question, but I'll maybe give a little context, I think on one of your podcasts.

And you said, we gotta dial that back. And you're like, wait a second. No. But then you've gotta, you've got that, and then you've gotta balance that with all your other newer employees that don't have the deal. So, you, know, things change over time. So how do you keep everybody happy?

Jay Ruane: It's tough And you actually took some advice from Seth and I kept the Friday, you know, Friday days off for that longtime employee. and it's, it's interesting. it's funny, well, it's not funny that we're talking about this now. That was like a struggle for me, a month ago. And I was like, you know, how do I deal this?

And then last week that longtime employee's 18-year-old son just graduated from high school a month ago, was driving from Florida to South Carolina to go see his girlfriend, fell asleep at the wheel, drove off the highway, died in a single car accident. And so we've now been dealing with that as a firm.

Jonathan Hawkins: my gosh.

I have gotten my time and I can do the things that secure their job, and really sort of live the life that I love. And so I'm, happy where I am in life. I have stress, but I don't have the type of stress that cripples me. I have the type of stress that invigorates me.

Jonathan Hawkins: Wow. That is a powerful story there man. But it, you know, the other point there is, no matter how much we plan, life's gonna be thrown us curve balls.

And if there's ever a conflict, then come to me and honestly say, this isn't the place for me anymore. And we just had an employee leave on Friday. Who was great. She started in January and she made it six months. Great person, good employee, but the conversation was, I'm an introvert, I'm working remote, I'm in my house. If I don't leave my house for a job, I can go weeks without talking to anybody outside of the firm. I need to have some sort of social interaction. Otherwise, it's not healthy for me. I have to leave this job, even though I love it. Awesome. I'm happy you recognize that you can move on and we'll figure it out and you're part of the alumni association now.

Jay Ruane: Well, there's

Jonathan Hawkins: not many people out there that are, that are taking that approach.

And so I stepped in and I, I covered some continuance and I loved it. 'cause I go to his courthouses and so I'm so rarely I mean I try to avoid court like the plague. I show up there, I'm like, Hey, I'm here on this file.

And they look and they see our firm name on it and they're like, oh, are you the new guy at Ruane's office?

And I say, yeah, I don't know what I'm doing. Dave's wife just had a baby, So can you give me a continuance? of like, I'll get you outta here. You know, don't stress, you know, we'll kick this out for a couple of weeks and Dave will be able to handle it later.

So now I'm trying to do stuff that I can contribute to the firm that other people can't. you know, 'cause I have a vision, I have a, a, way of looking at things. and so I think I serve the firm well in my capacity. But I could always jump in if I needed to.

Jonathan Hawkins: Yeah. so the way I sort of talk about it is, is, you know, I think it's healthy for a firm to have, what I call it, slack. If everybody is stretched to the absolute maximum, or a 100 or 110%, if you add anything new to it, it's, something's gonna break. But if you have some slack you know, you can push it around and sometimes, you get to, you know, somebody leaves and you don't have the slack. But the goal is, in my opinion, for a healthy organization law firm or not is to have some slack in there so you can fill in where you need.

Jonathan Hawkins: So that leads me to my next question you mentioned sort of you know, what it is you do now? So what is your role now? what's a typical week like for you?

Jay Ruane: So I have a meeting at Tuesdays at two o'clock with my CRM developer. We you know I started so long ago. The only thing that was out there in the space for managing lawyer's time was a a server based time matters. If anybody remembers, time matters from 30 years ago. That was the only CRM that existed. And, that was basically for civil firms, not for criminal.

Jay Ruane: So it's simple. We were, I was looking for, because I had so much time freedom.

And I said, well, there's a way that you can have both and be balanced. But those organizations didn't wanna do anything with business.

So I just said at one point, screw it. I'm gonna do it on my own. So I literally, I posted, you know, I'm thinking about doing this Mastermind. Is anybody interested in joining? I got 10 emails back. If you do that, I'm there. So I just decided, all right, what am I gonna call this thing? You know, elite builder, blah, blah, blah. And I just was sitting around and I was like, the criminal Mastermind. There you go. That's it. Right? That's it's the perfect name.

Jonathan Hawkins: So I'm a criminal defense lawyer out there who's not in it, hasn't heard of it. How do I get in? Is there an application?

Jonathan Hawkins: So what, what's the website?

Jay Ruane: The criminalmastermind.com.

you know, this is a rabbit hole that I'm starting to go down. I'm, I'm much farther behind than you. but there are lots of lawyers out there there are still scared as hell on this thing Oh, there's a fake case. I can't even touch it. so let's go. So, I guess you've been at it, how long have you been at it and sort of what was your gateway into it? Was it ChatGPT, like everybody else or I.

Jay Ruane: So ChatGPT launched and I signed up that very first day. I said, I gotta check this thing out. and I, you know, with fits and starts, I was like, oh, can you create me a script for this? And, eh, and I got better at prompting and really now what I'm finding is I will, I like Claude in terms of the content.

Like, I mean, grock has its limitations. I don't like the way it writes, but it has access to real-time data from, from X that you can't get in some of the other, other things. So everything has its place. I mean, just like you know, you might go to Chick-fil-A one day and you might go to five guys another day, or Shake Shack, you know, everything has, its, its role.

Jay Ruane: I'll tell you, I think what the biggest problem is, and I actually put this in my newsletter that goes out tomorrow. The biggest problem is it's a wide open world of ai, especially with the videos, with the you know, the speaker list YouTube videos that you could create at massive scale and and all the content you could create for websites and all the coding you could do.

Hey, you know, ChatGPT, what questions should I be asking for this? and they'll, you'll get that outta them even better.

Jay Ruane: of the people that are behind you. I mean, that's the reality. I mean, my father loves the client narratives. He's still practicing at 76. He sees, he is like, this is amazing. I've been practicing for 48 years. I've never had something this good to advocate for my client. I love it. He loves the byproduct. He just, he's not actively doing it 'cause I've automated the whole thing but he loves the output and can use that at court for sure.

Jonathan Hawkins: So, so let me ask about some of the automation. What tools do you use to help automate the AI stuff?

Jay Ruane: So I've just been using the native integrations with Claude and with Google Drive and with Gmail. We're using Zapier for some things.

So Zapier or Zapier, whatever, it's however it's pronounced. I mean it's a French company, so I would think it'd be Zapier, but everyone says Zapier. I just, you know, stick with what I know and that's part of the problem.

Like, you know, I, my, my MailChimp account for my law firm is probably a mess. 'cause I've had it for 20 years. The new MailChimp account for the Mastermind is so much cleaner and nicer. you know, I I, I stick with the tools that work rather than try to invest in. And I think that's the other thing too. Too many people just love to buy things as a lawyer because they think there's gonna, they're buying a magic wand. There is no magic wand.

Jonathan Hawkins: So, so Jay you've been very kind and I have probably about three hours more of questions and we don't, we don't have time for that. So but I do have a few. I do have a few that I wanna make sure I ask you.

So, we had talked about this offline, but I'm curious, you know, is there a sort of a a strong opinion or life philosophy that you have that you live by?

Jay Ruane: Yes I do. And I try to teach it to my kids, and I tell everybody that I interact with that. This is my philosophy. As humans we have the infinite capacity for only two things. That is love and that is knowledge. You should seek out as much of them as you possibly can.

Jay Ruane: That's true. That's true. I mean, you know, the reality is that at the end of the day, people connect with people. I mean if I can use AI to allow me to connect with more people, I win all around. I'm using a tool that's out there And, I think we could all do better connecting. You know, we come into our offices, our door gets shut, we put our head down, and we do work as lawyers, but you know, people look to lawyers to solve problems they can't solve themselves and that's really, you know, a challenge that we have. And it's, an honorable profession to have. So I think, we could really do better by each other for sure.

Jonathan Hawkins: So I do have another question before we go there. You've written a number of books, there any you want to plug? You know, I've read Tiger Tactics. I guess I read the first one. I think there's a second one. I Don't think read that

And it went from being, you know, 200 pages to 450 pages and I couldn't get it over the finish line. And I said a month ago, shit, I could just have Claude help me out, reformulate a couple of these chapters and I put the right prompt in. I used ChatGPT and Claude melded them together. I got the book out, it's on available online now. the Connecticut Criminal Trial Handbook. And I did that knowing that I would be able to use some benefit as being known as the author of this criminal trial handbook in Connecticut. They would, I would get some love on the internet because of it. I also wrote the one day MBA for lawyers because I had been looking for something like that, for years and there really wasn't anything out there.

Jay Ruane: Well, I.

Jonathan Hawkins: I you, anything you can point out.

Jay Ruane: Well, I mean for tiger Tactics for that series of books, it introduced me to an amazing group of other lawyer entrepreneurs that are out there. Got me a bunch of speaking gigs to audiences that I wouldn't otherwise have been in front of. And I enjoy helping other people. you know, I grew up. I'm not very religious, but I went to a Jesuit high school in Jesuit college. and so I believe

in their philosophy of being a man for others, and giving back as much as you can. So that's really what steers me. And if I could write a book and, be honest about the struggles that I've had, maybe somebody else who's in those struggles says, okay, I. These are not insurmountable.

They are just part of the process. And so, you know, when you look back, you say, oh God, that hill look so large. but I got over it and now it doesn't look so large. and that's really what I wanna encourage people to do. Like, you can do this. You're smart. If you got into law school, If you passed the bar, you're smart enough to do most of these things.

You go deep in an area, but you have a wide variety of knowledge going across the top. I think I probably have a, I'm more like a WI go up and down and up and down in multiple sections.

Jonathan Hawkins: I love it. So Jay, you know, as a, as an outside observer, you know, I mean, you've done, you've had an incredible run as a legal entrepreneur. You've done a ton of stuff. I mean, it, I mean, we've talked about some of it, there's a ton we didn't talk about. But as you sit here today and you're looking forward, you know, what's the vision for the next 10, 15 years? What is it that you haven't done yet that you want to do?

Jonathan Hawkins: I love the goal and I love the public declaration. I think that's key. That's key. Most people forget that part, and they just, it just drags on

Take every class you can get, start teaching the classes. Really embrace it. If that's what you wanna be, go for it. I encourage you because if that, if that fulfills you, man, you should be doing it. but don't do anything half-assed. that's the takeaway.

Jonathan Hawkins: So Jay, for somebody out there that wants to get in touch with you, what's the best way?

Jonathan Hawkins: Well, Jay, man, this has been great. I've enjoyed this. Thank you for coming on. I look forward to meeting you, meeting you in person soon.

Jay Ruane: Yeah, definitely. We'll have to get together at some event. I, you know, you know, as my kids get a little older, I'll and my daughter starts driving, like we talked about before, coming on the air you know, I'll be able to escape more and get back on the seminar circuit. So I'm looking forward to that

Jonathan Hawkins: Awesome. Well, I appreciate it.

Jay Ruane: Thank you so much.