Episode Notes

The Small Firm Roadmap Revisited doubled down on our Healthy Firm model. But what, exactly, is it? Join us for another stop on our podcast book tour. This week we dive into what it takes to be a Healthy Owner—beyond the traditional concepts of what it means to be “healthy.”  

Sara talks with Lab Coach and personal injury firm owner Ryan McKeen about making the decision to build a resilience muscle, leveraging the time and talents of others, not letting your 5-year-old-self run your business, and ultimately, letting go of control.

Links from the episode:

$100 Million Dollar Day in Boston

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  • 5:23. Building Resilience Muscle
  • 9:38. The Liberation of Letting Go
  • 17:45. Defining a Healthy Business Owner



Welcome to The Lawyerist Podcast, a series of discussions with entrepreneurs and innovators about building a successful law practice in today’s challenging and constantly changing legal market. Lawyerist supports attorneys, building client-centered, and future-oriented small law firms through community, content, and coaching both online and through the Lawyerist Lab. And now from the team that brought you The Small Firm Roadmap and your podcast hosts 


Sara Muender (00:35): 

Hi, I’m Sarah Muender 


Stephanie Everett (00:36): 

And I’m Stephanie Everett. And this is episode 467 of the Lawyerist Podcast, part of the Legal Talk Network. Today, Sarah is talking with one of our lab coaches, Ryan McKeen, about what it means to be a healthy owner. 


Sara Muender (00:51): 

Today’s podcast is brought to you by Posh Virtual Receptionists, Postali, & LawPay. We wouldn’t be able to do this show without their support. Stay tuned. We’ll tell you more about them later on. So, Stephanie, I hear that our lab coach Ryan, who is on this episode today has something really cool coming up to help PI attorneys specifically. Could you tell us about that? 


Stephanie Everett (01:16): 

Yeah, so Brian and his team, some will remember they just had an amazing record breaking verdict in their state. They had a hundred million dollars verdict, and they want to share that knowledge of how they got there, how they put the case together, how they presented it to the jury, and they want to give back to the PI community. So they’re putting together what they’re calling a $100 million day in Boston. It’s happening November 9th and 10th. It’s a ticketed event, but they promised to give a ton of value. They’re going to give you actually a collection of their openings and their closings and their witness examinations. And what they did with the focus group, they’re really going to dive deep into their trial strategy and really share with PI attorneys how they got where they did with this case. So we’re really excited for this victory that they’ve had and that they’re just so willing to share in this way. So if you’re interested in that, we’ll put a link to the registration page in the show notes. And so Ryan, as you know, we all love him and adore him around here. I just think he’s an amazing human being and is so giving. And so Sara, I’m really excited to just dive right in and hear this conversation that you did with him about what he does to be a healthy owner. 


Brian McKeen (02:37): 

Hi, I am Brian McKeen. I am the CEO and co-founder of Connecticut Trial Firm. We are a personal injury firm located in Hartford, Connecticut area. I am also a strategy coach at Lawyerist Lab. 


Sara Muender (02:51): 

Well, welcome to the podcast. Welcome back to the podcast, Ryan. I’m super excited that we get to hang out today. We just got hang out at lab, sort of. We were just talking before we hit record that we were passing each other through the hallways and we were coaching people and running workshops and stuff like that. And so I’m really excited to get to know you better today and for our audience to get to know you better because like you said, you’re a coach here in Lawyerist Lab and you provide a ton of value for people. So tell us a little bit more about your firm when you started and maybe some of the steps along the way that got you to where you are here. 


Brian McKeen (03:29): 

Yeah, 11 years ago, I quit my job as an associate. I saw a better way to practice. I was inspired a lot by the content Lawyerist and Sam Glover and Aaron Street were putting out at the time about using the cloud and being transformative. And I didn’t see those opportunities in the existing firm that I was at. So I decided, look, I’m going to go paperless. I’m going to use cloud-based software and I’m going to start my own firm and I’m going to try to run it like a business. And I went out and I formed a partnership. I did what most people do, and I called a friend and I was like, Hey, do you want to start a law firm? And within six months, we weren’t talking within a year, we weren’t partners. We’ve had a Lawyerist episode, a podcast episode. We are all friends now. It was not fun. So I then went solo and I was solo for a few years. Ultimately, I partnered up with my current partner, Andrew Garza in 2016. We really became full partners in 2018, and now our firm is 37 people. So we’ve, I’ve been at all ends of the solo to small firm to, I guess I’m not even sure we’re a small firm anymore. 


Sara Muender (04:39): 

Yeah, yeah, absolutely. Well, I mean, it’s a journey. It’s never a straight path to get to where you are or get to where you want to go. And there’s challenges along the way and it can be excruciatingly difficult and challenging sometimes mentally. It can take a toll on our mental health. It can take a toll on our relationships when you have to pour so much into something. And I mean, I can imagine, Ryan, when you’re managing that many people and you are trying to row this boat in the direction that you want it to go, things happen. And I think that working with people is arguably the hardest part of running a business from my perspective. So how do you do it? How do you do it all, Ryan? 


Brian McKeen (05:23): 

One day at a time, one meeting at a time? I think that what has happened over the course of my entrepreneurial journey is that I’ve built a sort of resilience muscle where things that would’ve greatly upset me or bothered me 10 years ago don’t really even register to me today because through experience, I have some perspective. I’ve been there, I’ve been through that. I’ve experienced that disappointment, I’ve experienced that fear before. So there’s not a whole lot of new there. And I think that that has been very useful. I think when I started out, I didn’t have perspective. I didn’t have community, I didn’t have coaches. I didn’t have something like Lab Con that could help me understand where I am, maybe what I need to do, maybe rephrase the problem or opportunity that I’m facing. And so I had to deal with it all myself, and that was incredibly stressful. 


Sara Muender (06:25): 

So how did that change then when you started to go along your path and then you started to bring people into your orbit and you started to get more support and make connections and then you’d get through one challenge and then there’s always the next one. I mean, how do you build that resilience muscle, I guess is what I’m saying? 


Brian McKeen (06:44): 

Yeah, this one is very clear to me where I had a lot of success. I was successful, I had some big settlements and I was always working and I was busy and I was building a successful practice except I was burning myself so hard that it became unsustainable. And I knew this was a day I can remember vividly our credit card declined. My wife was sitting across from me at a table and then she looked at another credit card balance and that was close to maxed out, and she just started crying. And I’m like, I am working so hard. I am trying to do all the right things. It feels like everybody’s mad at me. Why am I doing this? This is not sustainable. And I did what I do in times like this, which is like, okay, I’m going to go for a walk. 



I have a walk. Nobody can take the walk away from me. I’m safe on my walk. And I listened to a podcast and I wish I could remember the episode, but it said basically, look, if you’re going to run a successful law firm, you have to be able to leverage the time and talents of others. And I was like, that’s the component to me that is missing. At that point, I didn’t have anybody that was working with me. I had a part-time paralegal for nine hours a week, but that just really wasn’t enough. And it was really at that point that I started thinking, alright, I need to hire people and I need to go out and I need to build systems. Or I might as well just not do this. I might as well go and work for the government. I will probably take home more money, have vacation time, have less stress and live a decent life. It wasn’t maybe the life that I had dreamed of or wanted, but it was certainly a more sustainable alternative than having my wife in tears across the breakfast table. 


Sara Muender (08:38): 

I think we’ve all been there. That’s a really painful moment and it’s scary. And I think just to touch on something that you had said, building this resilience muscle, I think for me personally, as I look back on the challenges that I’ve been through, we’ve been through some really hard times, but it’s sort of like when you go through so much and you’re so worn down and you kind of hit this, what some people might call rock bottom of your life, whatever that looks like, everybody has a different bottom, if you will. It could be a mental rock bottom, it could be an overwhelm rock bottom, it could be a financial rock bottom. It’s kind of liberating, like I have nothing left to lose. So you made a decision, Ryan, and that’s what I think people are maybe afraid to do is make a decision. But when you don’t make a decision, that’s also a decision, and then things just either keep going the way they do or they don’t. What do you think? 


Brian McKeen (09:38): 

Yeah, I think one of the things that I do is, and I’m not a Buddhist by any stretch, I read a lot of books on Buddhism and I think about the concept of letting go and the need to let go. And you talked about that liberation and really the liberation there was letting go. It was letting go of me feeling like I needed to do everything I needed to make everything happen. And in letting go of what I was holding onto so tightly, I was able to see the world and see my business in a different way as I think. And as things get hot and as things get stressful, and believe me, growth has put some country miles on me of growing affirm. So that’s not all been easy, but when I start to feel that way, I start to ask myself the question of what am I holding onto? Because it’s usually that the tighter we grip, the more pain that we’re in, and oftentimes letting go is a choice, and it is a powerful lens to view your life in law practice through. 


Sara Muender (10:49): 

Wow, that’s so beautiful and so simple. But why is it so hard when you talk about leveraging the skills and time of other people makes me think about delegating, and that’s a very scary word for a lot of people. It’s one of the things that often is the focus of my coaching, and I’m sure that it comes up with you and your Labster that you coach as well. Delegating I think is so hard because there’s so much good intent behind it. I think that it’s when we don’t, and we hold on, like you said, we’re not letting go of wanting to be in control of all the things of our business. And it’s scary because this is what I tell my Labster, because you care. It’s because you care about your clients, you care about the work product. That is a beautiful reason. Of course you’re going to protect that and hold that so sacred. And then I think also it’s this fear that they’re already overwhelmed, but then it’s going to make them feel even more overwhelmed. It’s going to take time to then train people and get them up to speed with the level of which you want them to deliver service and work product. So what did that look like for you in those early days of starting to let go and starting to bring more people on your team so that you could free up yourself? 


Brian McKeen (12:12): 

Yeah, I think for people going through this, so I’m going to touch on a lot here, but one of the things for people going through this is therapy is necessary. You said the hardest thing in running a business is other people, and maybe I can accept that, but really for me, the hardest thing has been what’s between my ears, my head, getting my head correct. And so for me, it was dealing with it in a therapeutic setting about what are my early attitudes towards money? Who are my role models, what values were deeply instilled in me? I mean, we’re talking three, four, or 5, 6, 7, 8 very young. And those attitudes, once you start figuring them out, you realize that you’re still carrying that person with you. And in many ways, if you don’t deal with it, you have your five-year-old self running your business, and that creates a lot of stress. 



Five-year-olds should not be running law firms. It is much more complicated than a five-year-old can handle. But that is where it all begins. And I see the number one thing in lobsters not, or for me, it wasn’t that I feared letting go, it was my attitudes really growing up, middle class surrounding help. We didn’t have a landscaper. My dad mowed the lawn, we didn’t have a house cleaner. My mom cleaned the house when something was broke, my dad fixed it. We didn’t call the plumber. So it’s all those very basic primal impressions that are in us that really impact our decision making. And once I was able to sort of identify those things and then look, the business thing is easy. And the problem that I see with most lobsters is that they express the desire to grow, but they don’t hire enough help to do it from just a very practical business perspective. But I would think, and if anybody out there is listening to it, work in therapy, work through your early attitudes surrounding money, your early role models, the impressions that your parents made, what their work ethics were, their attitudes towards work, and I think you’re going to get somewhere pretty far in your practice. 


Sara Muender (14:23): 

That’s such a good point, and I love that you said it is challenging when you have a team of people that you’re, I hate to use the word in charge of, but that you’re leading because everybody’s different. And all of those people on your team have their five-year-old sounds that they bring to work. And what I’m hearing is it’s our responsibility as a leader to set the example to deal with ourselves first. And I think when we do that and we keep an open mind and we commit to growing and becoming a better leader and questioning our assumptions and questioning our beliefs, and is this the way others see the world? Why is this person not doing it the way that I want them to do it? Because it’s taking responsibility, being willing to take radical responsibility for everything in your business, even the things that other people do. And that is also so freeing. We’re going to take a quick break to hear from our sponsors and then we’ll circle back. 


Zack Glaser: 

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Sara Muender (17:45): 

All right, Ryan. So clearly it’s up to us as the business owner, we’ve got to take care of ourselves so that we can show up for this team and lead them and row this boat in the direction that we want, create the business that we want that serves clients and serves our lives. So what would you recommend besides, you mentioned therapy and you mentioned things like taking a walk. What do you think defines a healthy owner of a business? 


Brian McKeen (18:12): 

The most important piece, I mean, look, people talk about exercise and sleep and diet and meditation and Yes, yes, and yes. Okay. Pull this in a little bit of a different direction. I’m going to talk about community and the importance of community in health because I think that for so many people and myself, it’s like it can feel isolating and isolating can be scary, that can increase those cortisol levels. So finding like-minded people, whether they’re other business owners, whether they’re your neighbors in the office suite or office condo, whether they’re people in the legal community, whether it’s people in Lawyerist lab, and engaging in that community, I think is one of the best things that you can do for your health. And there’s been studies about athletes, and one of the studies that I read was fascinating. It was like the best way to become a better athlete was to join a great team or train with people who were great. 



And there’s just such a human element to community, and I think it’s not discussed a lot in terms of wellness and health, but simply being around like-minded positive people, people who are trying to do, people who are supportive. And one of the things that I was really quick to do was to seek community nationally, because I would go to local bar events and it would just be so depressing. It would be so myopic and it would be so negative. And when you’re around negative professionals, nothing kills your energy more when your teammates are negative, nothing kills your productivity more. So trying to surround yourself with a community that is healthy and positive and supportive. To me, if you took nothing else from this podcast, but trying to find that for yourself, you’re going to improve your life more than anything else I could ever tell you 


Sara Muender (20:10): 

That was so apparent. At Lab Con, our annual in-person, unconference, as we call it, it’s more of a two and a half day working retreat. And this was my third lab. I don’t know how many times you’ve been probably way more times than I have, but this was by far the best of the three that I’ve been to. And I’ve heard it was one of the best we’ve ever had. There was almost like, well, first of all, we had a great turnout. I mean, it was sold out and we’ve had so many people join Lab this year, so there was a lot of fresh energy, and they then agreed to show up and not really know what to expect. Everyone was nervous. A lot of our Lawyerist in lab are introverts, and it’s really intimidating sometimes to get into a room when you feel like everybody else has got it figured out and you don’t, and you have all these problems and you’ve got family issues and you’re overwhelmed and all the things. 



But what happened was they got in and the thing I just kept hearing over and over is these people never made me feel alone. And they felt that support and that comradery, and I feel so confident in saying that no matter what it is you go through in life, the hardest of the hard challenging situations and challenging chapters, it’s really not as bad when you have someone there with you. It is like they say in therapy, traumas don’t have to be so negatively impactful if you are not alone through them. So let’s say someone’s listening to this Ryan, and they’re about to crack. They’re really overwhelmed, they’re burned out, they don’t know where to start. Maybe they’re incredibly discouraged. Where should they start? What would you recommend? Just take that first step. Let’s shift directions a little bit, but it’s going to take you in a whole new direction. What would that look like for you? 


Brian McKeen (22:08): 

Well, first of all, if you’re really about to crack a therapeutic setting. Joining Lab is step two. But a therapeutic setting to engage in therapy and engage with the help of a trained mental health professional is invaluable. Find access to that, pay whatever it is, make that happen and start there. And yes, something like Lawyerist Lab was, I was a Labster, and it was an incredibly powerful to me for a few ways. One was the community of people that I had met and were engaging in people who were struggling the same way I was struggling, people who were dealing and talking openly. One of the things that goes on in the legal space is sort of what I call in probably every space, but it’s sort of like, look at me. Look how awesome I am. Look at the cool thing that I’m doing. And so people come out of conferences, I need to be doing this, and oh my gosh, I’m not doing this. 



And so they go there trying to improve their lives, and they end up feeling a whole lot worse. I remember I was coming back from a conference one time, we were getting on a plane and somebody was talking to me about how they needed to expand to six different states, their practice. And I was like, have you thought about this before? Are you maximizing the state that you’re in? No, but this person was so anxious after seeing people who just talked about their successes. So finding people who are real, finding people who are authentic, finding people who are honest with their struggles, and coaching is a big part of it. I am very simple as a person, and one of the simple sort of life hacks is look at the people who you admire and who are successful and watch what they do to a person. The most successful business owners, lawyers, people who are happy, healthy, whatever. However they define success. I don’t want to define them in their own terms. They are coached. And having a coach who can hold the mirror up to you, who can work you through problems, who can help you get perspective, that is invaluable because really the battle is between your ears and getting your head straight. Usually the business side of things are really sort of simple and uninteresting answers a lot of times. 


Sara Muender (24:24): 

Yeah, well said. So we brought you on this podcast today, Ryan, because you run a healthy law firm, we consider you a healthy owner, you’re a coach in lab, and if people who are listening resonate with what you said today and they feel like you could help them, what are some of the things that you focus on and what are some of the things that you help our lobsters with? This is for me too, because I honestly don’t know much about your coaching practice on that side of Lawyerist. 


Brian McKeen (24:53): 

I always begin my calls with the question that Stephanie began our calls with many years ago, which is, what does help look like for you today? And let’s go and let’s improvise, and let’s talk about what it is that you are struggling with. And so in that way, as a coach, I’m trying to meet them where they are. I’m not trying to pull them way. I try very hard not to have any agenda, just listening, trying to guide gently and making suggestions where possible and trying to get them. Oftentimes what happens is in life, we talk about letting go. I think it’s a good theme for this podcast because what they’re doing is they’re trying to hold on to some solution, and it’s like, oh my gosh, all the employees are failing me forever. And then it’s breaking them of that where it’s like, look, we all hire from the same pools. 



There’s all these people or people, let’s talk about your onboarding process. What is your onboarding process like? And then they’re like, oh. And then it’s like, well, I don’t have an onboarding process. And then it’s like, well, maybe you should have an onboarding process. And then trying to oftentimes break them of what they’re holding onto and then shifting their perspective into maybe a different way to look at the problem or maybe six different ways to look at the problem. And so they start one place, and ideally I’m able to move them by the end of the call to some other place. 


Sara Muender (26:21): 

Yeah. Awesome. Well, with that said, if you are listening and you’d like to have a conversation with Ryan or you’d just like to meet Ryan, why don’t you get in touch with us here in Lab and we’ll set you up. Thanks, Ryan, for coming on the show, and I hope that you keep taking care of yourself. Thanks for all the work that you do in Lab and 


Speaker 1 (26:42): 

With our Labster and in your law firm and for the world. 


Brian McKeen (26:47): 

Thank you, Sarah. Thank you for having me. 



The Lawyerist Podcast is edited by Britany Felix. Are you ready to implement the ideas we discuss here into your practice? Wondering what to do next? Here are your first two steps. First. If you haven’t read The Small Firm Roadmap yet, grab the first chapter for free at Lawyerist.com/book. Looking for help beyond the book? Let’s chat about whether our coaching communities, are right for you. Head to Lawyerist.com/community/lab to schedule a 10-minute call with our team to learn more. The views expressed by the participants are their own and are not endorsed by Legal Talk Network. Nothing said in this podcast is legal advice for you. 

Your Hosts

Sara Muender

As a Lab Coach, Sara works with lawyers to build healthier law firms through workshops and 1:1 coaching. She makes sure lawyers have the guidance and tools to implement their ideas and grow their businesses.

Featured Guests

Ryan McKeen

Ryan McKeen is a Strategy Coach at Lawyerist. He is also the co-founder and CEO of Connecticut Trial Firm. His leadership has not only led the firm to secure a record-setting $100 million jury verdict for a workplace injury, but has also earned it a spot on the prestigious Inc. 5000 list of fastest-growing companies in the nation. Recognized for its exceptional work environment and culture, Connecticut Trial Firm has been honored as one of the Best Workplaces in CT. Ryan’s individual prowess as a lawyer is underscored by his membership in the Multi-Million Dollar Advocate Forum, an accolade reserved for attorneys who have won multi-million dollar verdicts and settlements. As an author, Ryan has contributed significantly to the legal literature with books like “Tiger Tactics” and “Tiger Tactics 2: CEO Edition.”  

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Last updated September 20th, 2023