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Featured Guest
David Leatherberry

David Leatherberry is a healthcare attorney and owner of Leatherberry Law in San Diego, CA. He focuses his practice...

Your Host
Adriana Linares

Adriana Linares is a law practice consultant and legal technology coach. After several years at two of Florida’s largest...

Episode Notes

Making the move into solo practice may seem intimidating, but for some, the transition brings freedom that makes it worth the risk. In this episode of New Solo, host Adriana Linares talks to David Leatherberry about how his work in a niche area of healthcare law led him to start his solo firm. They discuss David’s background in the legal industry and he talks about his current passion for helping behavioral health practitioners with their legal needs. He also shares the story of his move to solo practice and how it helped him prioritize his professional goals and personal well-being.

David Leatherberry is a healthcare attorney and owner of Leatherberry Law in San Diego, CA.

Special thanks to our sponsors, ClioAnswer1Lawclerk and


New Solo

The Journey from a Big Firm to Solo Practice



Intro: So you are an attorney and you have decided to go out on your own, now what? You need a plan and you are not alone. Join expert host Adriana Linares and her distinguished guests on New Solo. Tune into the lively conversation as they share insights and information about how to successfully run your law firm, here on Legal Talk Network.


Adriana Linares: Hello listeners. It’s Adriana Linares, your host of New Solo. Thanks for tuning in to another episode. If you’re new to the show, welcome. I hope you appreciate it and learn something new. I’m a Legal Technology Trainer and Consultant for those of you that are regular listeners. I think you know that.

What you may not know though is that last year I took on a gig, a project at the San Diego County Bar Association. So in my regular travels, I just added San Diego into the loop and I get to come out here one week of every month and help their members as part of a member benefit with practice management and technology questions.

One of the projects that I created and really wanted to do is that of the concept of law firm makeovers, so you know how there’s all these shows about restaurants being made over and if you’re a fan of the profit, different businesses and I thought well law firms can sort of fit right into that mold and I really wanted to do law firm makeovers.

And it took me a minute but I found an attorney, a member of the San Diego County Bar who I thought would be perfect for a role like this, and that’s what this episode is about. His name is David Leatherberry, he’s an interesting, really a hell of a sweet guy and he was with the big law firm, which you’ll hear about in this episode, decided to go out on his own and has an interesting niche practice.

So I’m going to do a couple of interviews with him over the next few months, just talking about how we took his solo practice which was still kind of new and are transforming it into a modern, mean, lean, mobile secure billing machine and he does good work, and that’s part of what’s in his heart. So I think you’ll really appreciate listening to him, listening to the types of clients he has and following along on his journey.

So here we go. But before we get started, I’m going to make sure and take a couple of important minutes of your time to thank our sponsors because they are the reason we get to produce this podcast.

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Adriana Linares: All right listeners, so I hope you enjoy my conversation with David Leatherberry. As I mentioned earlier, he’s an attorney in San Diego and a member of the San Diego County Bar who I have taken on as a project and this is the first episode of David Leatherberry’s Law Firm makeover.

So let’s get started.

David Leatherberry: Okay.

Adriana Linares: Let’s talk about you.

David Leatherberry: All right.

Adriana Linares: Do you want me to talk about you?

David Leatherberry: I don’t know, well you can start out with what you know but no.

Adriana Linares: So, you are what I jokingly referred to as a big firm refugee. I’m not the only one, I mean we used that term out there in the world of attorneys who were with a big firm and decided to try and go out on their own.

David Leatherberry: I thought you were going to male and pale but –

Adriana Linares: Oh no. Well, it is a podcast and they don’t know what you look like.

David Leatherberry: Yeah.

Adriana Linares: You are male.

David Leatherberry: I am male, middle-aged, gray hair, white male.


Adriana Linares: Do you think at your middle age, which you said it, I’m not going to say it but you said it, that making this decision to go out on your own was harder or easier? Like what would David at 30 have done versus middle-aged David? Would it have been an easier jump?

David Leatherberry: Well part of it. I think some of it is my personality, because at 30, I also — that’s when I went to law school and so –

Adriana Linares: A late bloomer.

David Leatherberry: Yeah, well I had other paths and I got driven. I got pulled away by a passion and that passion took me to law school. And so, I have — I think there’s a point, there’s a certain degree that you have to be willing to jump. That said, nobody should ever get the idea that I’m somebody who is a cliff jumper or I tend to be very cautious. I need to see where the stones are before I cross the river. I need to plan, I get very anxious, I don’t want to just jump, but for me, I think there are certainly things that make it much tougher to do later in life whether you’re 30 or 56 that you don’t have when you are younger.

And I think the problem you have when you’re younger is you just don’t know what you can do and so you get frozen. But you have so much less risk when you’re younger.

Adriana Linares: Right.

David Leatherberry: And when you’re older and you tell, your kids, your spouse, your professional associates and friends, hey I’m taking a leap, they truly look at you like you got something wrong.

Adriana Linares: Right.

David Leatherberry: This is a midlife crisis, and take a nap you’ll get over it. But some of the advantages are that you’ve seen through enough challenges and crises that you know that you’ve got a pretty good chance of bouncing and landing on your feet in some way, it may not be the way you pictured it, but you’ve got a pretty good chance of turning out okay and it has. I have been happy with that.

Adriana Linares: Oh, we can’t wait to hear, we should back up.

David Leatherberry: Yeah I’m long-winded, I’ll take you all day, so sorry.

Adriana Linares: No, I think that’s okay, but we should introduce you.

David Leatherberry: Okay.

Adriana Linares: So we know you’re 56, male.

David Leatherberry: Yes, about to be 57.

Adriana Linares: You’re not that pale, I mean maybe you went out in the sun this weekend.

David Leatherberry: It’s the sun.

Adriana Linares: Okay. And you were at a big firm?

David Leatherberry: Yes.

Adriana Linares: Oh, and I should say we’re at the San Diego County Bar Association, Bar Center 401.

David Leatherberry: Bar Center 401.

Adriana Linares: As it is lovingly called.

David Leatherberry: The fabulous downtown office.

Adriana Linares: That’s right and we met, you and I –

David Leatherberry: That was fun.

Adriana Linares: Because I get to work here as the Member Technology Officer and I was looking for a project, a law firm makeover, you called me up and said hey, I’ve got a new law firm and it needs a makeover.

David Leatherberry: Well, but I had, well, there is more to it, you want to tell?

Adriana Linares: There is, yes, but first, I want you to give us just your background. So you are at big firm, what kind of law do you practice? How long were you there? Why did you decide to go on your own?

David Leatherberry: So, a big firm 14-15 years thereabouts firm that’s across the country in pretty much in most states, if not every one of them. I was part of a large national healthcare group, a partner with the firm and the group functioned as some of the large firm groups do where your practice group is kind of a microcosm of the firm in general.

Adriana Linares: It’s a fiefdom among the kingdom – of the Kingdom as I often say, that’s how I spent eight years to a Florida’s largest law firms and that’s where I got my whole learning of how law firms work and I learned that pretty quickly, not only are many individual lawyers very much like solo practitioners, but the practice areas are often like fiefdoms that are part of a kingdom.

David Leatherberry: Yeah. But I often tell I do some teaching. I teach at a law school and one of the things I tell students as well as new lawyers who are trying to meet other older lawyers is that being an associate in a firm is a little bit like working in a mall.

Adriana Linares: Oh yeah?

David Leatherberry: It is, because you have — once you get past the grace period, you live according to the billable hour and you have — there are certain productivity thresholds you have to hit if you’re going to go anywhere. And so, you can’t be complacent, you can’t expect work to always be coming from the partner that hired you. You have to be anticipating slow periods and then you’ve got to go shopping, and then you go to the other stores on the mall, which are the other practice groups and you find work.

Adriana Linares: It’s true. That’s a great analogy.

David Leatherberry: I think what ended up happening was because of my own — some of my just life experience as well as some time there was just a bit of a — maybe serendipity, I made a connection with a certain sort of client base that was a very niche base.


David Leatherberry: And so that started growing, and it became very much why I’m doing what I’m doing now. But as it grew, then I think the firm had to figure out what to do with me because I was an associate in some ways, but I was also bringing in enough that I think it became too expensive to pay me bonuses so.

Adriana Linares: Really?

David Leatherberry: Maybe a partner instead.

Adriana Linares: Oh I was going to say. Okay, so now you’ve made it. Did you mean to develop a — so you’re a niche on the niche, conversation 00:10:38.

David Leatherberry: Actually I tend to be a preferred niche but I recently had part of my house redone by a woman from Israel and that she kept talking about the soap niches so that I could never figure out what she was talking about, so from since then it’s been niche.

Adriana Linares: Okay.

David Leatherberry: Sorry.

Adriana Linares: Okay. Did you realize you were building a niche practice or did it sort of happen and then the firm said oh wow, that’s an interesting niche practice or was it some — because a lot of times firms will purposefully see an opportunity, a space and go for it.

David Leatherberry: Well in my limited experience, niches are not necessarily a first-tier firm target because you tend to want to go at least from the marketing exposure I had, you tend to want to go from broad base areas that might be underserved that have the depth to absorb rate structures that can be profitable.

And when you’re talking about niches, you tend to be talking about areas that don’t necessarily have a lot of insurance behind them or they don’t, there may not be a number of practitioners, they’re easily absorbed by a single expert. And so it can be expensive to get into that.

At the same time, and this is again I think it’s good advice for younger lawyers, is that and I see this in medicine all the time, is that if you develop a specialization in an area, we’re in a complex road right now and eventually somebody is going to tap into that area and need help and there’s going to be nobody else there, and that’s an ideal spot to be in or at least it’s a pretty rewarding spot.

Adriana Linares: Yeah.

David Leatherberry: And I think the personal relationships you get out of that were rewarding for me. So I did not target, I didn’t set out one day and say, okay, what niche can I find? Although, I know people will try to do that. It may sound a little bit cliché but it actually evolved out of things that I’ve liked doing and people I enjoyed working with.

And this is where two parts of my life came together. So I mentioned that I left in my mid-30s, I decided to go to law school because I had become passionate and I’d become passionate about advocacy. Particularly, I started working as a — what’s called a Court-Appointed Special Advocate at CASA with Voices for Children. Because I had a rewarding job, I had a corner office in a firm or in an office in the Financial District in San Francisco, I wasn’t yet a lawyer, I wasn’t working for a law firm.

But I decided, I want to go, I want to do this advocacy work, and so through that, through the child advocacy, I started working with the mental health system. And throughout all of that experience and then going to law school, and graduating law school, I continued connections and doing advocacy work in different areas of mental health.

And then what I found is while I was working with the firm, and I was doing health law, and representing institutions, skilled nursing facility, doing patient care cases, some other transactional things that came up with larger institutions, I was doing a lot of pro bono work volunteer hours on the mental health side.

And so, I even I got a service award through the San Diego County Bar and something through the state, it’s called the Wiley M. Manuel Award for pro bono services for the mentally ill. But this was something that wasn’t attractive to the firm because that’s not an area with any money.

Adriana Linares: Of course not, especially not at big firm.

David Leatherberry: Not at big firm, no.

Adriana Linares: Right.

David Leatherberry: So I was considered I get sort of nicknamed in a somewhat derogatory way, the pro bono lawyer.

Adriana Linares: Damn lawyers, they just want to do good sometimes.

David Leatherberry: No they’re all good people and people did great pro bono things I mean I could tell you wonderful stories but it’s just hard to maintain that balance while working in a firm where you have to be very conscious of the fact that you are a business, you’re a large business and you have to be focused on the bottom line.

Adriana Linares: The kingdom rules. All right, so you did that for 13 or 14 years?

David Leatherberry: Yeah.

Adriana Linares: And then you were a partner I mean you probably could have glided into retirement.


David Leatherberry: I don’t know if anybody glides into retirement anymore and it’s hard because being a partner, there are different levels of partnership. And so, there’s always somewhere higher on the ladder to go. I certainly hadn’t stopped moving up or moving I was still — there was still a lot of growth to happen as a partner. But there were just a number of things that were happening in my life at that time that I finally had to begin to listen to my inside chatter that I wasn’t happy.

Adriana Linares: Wow.

David Leatherberry: And it wasn’t healthy I mean there were just a number of things that were just coming together. And at that point in life, there are other things that begin to exert pressures, I had both parents who were terminally ill. My father had been diagnosed with mesothelioma, and was needing a lot of care fairly rapidly, as he was decompensating.

And so he had care but what people don’t realize is that there are doctor’s appointments several times when I had — be driving him to one doctor’s appointment, get back, pick up my mother drive her immediately to the next doctor’s appointment and then you’ve got to go back in and still figure out how you’re going to get the time bill for work.

Adriana Linares: Right.

David Leatherberry: And I was doing it but you’re burning the candle at all ends. And so it was a matter of that those pressures and then somewhat of an internal, you start looking inside me, which is saying I’m not happy, and I’m fudging words here, I mean I was getting really unhappy, I was getting clinically depressed.

Adriana Linares: Right. Well and there’s so much of that that happens in this profession and we hear about it all the time to face it, face to face and say okay well now I’ve got to really change something or it’s not going to get better on its own, right?

David Leatherberry: Well and this — you’re dead right, absolutely right. This is another one of my sort of pet projects is that in the profession and there’s a lot of press out there about how lawyers struggle with substance abuse, and mental illness depression. We have a very high index for depression and it starts in law school and there’s been some really interesting studies that show how actually there’s a certain amount of self selection that goes on because there are characteristics of depression that are very successful in law school; for example, anxiety about details that tends to make you a pretty good —

Adriana Linares: Candidate for depression.

David Leatherberry: Well it also makes you —

Adriana Linares: Oh My God.

David Leatherberry: It’s a characteristic of depression because it’s part of an anxiety disorder. I’m not a clinician so I can’t, I don’t want to say its diagnostic, but depression is an anxiety disorder. And so, there are a number of things that personalities that tend to succeed in law school also tend to be prone to depression.

And I’d read some pretty desperate spots and at the same time, I was still doing all this pro bono stuff, right, I’m still getting calls every day from healthcare providers, and it was the range was starting to expand from just, from San Diego to San Francisco. I mean people of Visalia of all places, out near Sacramento. And so, I started pencilling out how much would I need to survive and if these people were willing to pay just whatever amount, trying to figure it out, could I make a go of it.

Adriana Linares: So when you say these people, you’re talking about practitioners?

David Leatherberry: Practitioners who were calling and there was a lot of word-of-mouth sort of —

Adriana Linares: About the pro bono lawyer.

David Leatherberry: About the pro bono lawyer.

Adriana Linares: So your pro bono work then was geared toward doctors.

David Leatherberry: Yes.

Adriana Linares: Okay.

David Leatherberry: It had become geared towards, I’d moved from the patient side doing — I used to do a lot of advocacy work with children mentally ill, and homeless, and sadly enough, they go together. Actually, I’ll give you a funny story if I can, I don’t know, tell me if I’m talking too much.

Adriana Linares: This is your story David, you can tell me all your funny stories.

David Leatherberry: So when I went to law school and I think in, it was the second semester and I’m thinking okay this is expensive and I wanted to figure out a way to maybe save some money and so I went to the dean and said I’m doing these court appearances in the dependency court working with minors, I have to do court reports, I have to talk to the judge, can I get some academic credit for this as being like clinic.

Adriana Linares: Huh?

David Leatherberry: And he said absolutely not. Nice, thanks, but you’re not a second year, you’re a first year. And it happened that there was a — one of the clinic directors was in the waiting room at that time and she specialized in behavioral health issues and working with homeless mentally ill. And so, she stopped me on the way out of the office and said you know because my work was all the children, she said if you’re working with children long enough, it’s not long before they end up in the mental health system which is something I learned pretty quickly and that’s because behavioral health is the stopgap for Family Services.


We run out of places to take care of kids in foster care, so they end up in psyche settings. So she offered me essentially position and the law school then paid much of my law school tuition in exchange for my working with that clinic. And I ended up staying with that clinic after I graduated, teaching law students, when I stayed there probably, I don’t know 8, 10 years.

Adriana Linares: Wow. Before we hear the next part of the story, let’s just take one quick second or two and hear a message from our sponsors.


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Adriana Linares: All right, we are back. David Leatherberry is telling us all about your background, and your big firm background, and then the interesting circumstances that got you through law school and how you ended up building a niche practice and unfortunately getting a little bit jaded at your big firm with all the resources and the cushiness of a big firm. So you started thinking, maybe I need to do something different.

David Leatherberry: I did. I mean a number, and we can talk about big firm, its rewards and frustrations.

Adriana Linares: For sure.

David Leatherberry: And I certainly recommend people if they had that opportunity, there’s a lot to learn through having a practice in that setting, in terms of — as you said resources and reshaping your priorities, but at the same time for me at least, there were priorities I didn’t want to let go of. And that priority was and even priority is I think the wrong word, it was a relentless dedication that I just couldn’t let go of, and that was to individuals that I saw and these individuals fallen off from all different walks of life who are trying desperately to do something, to build something, who want the help of professionals, of lawyers particularly, but can’t get access to them.

Adriana Linares: I know you are talking about the doctor clients?

David Leatherberry: It surprised me in my case, yeah, it was healthcare providers.

Adriana Linares: Okay, right, let’s call them healthcare providers.

David Leatherberry: Well I think that because there’s so much of the discipline, I don’t want to limit it to doctors.

Adriana Linares: Yes.

David Leatherberry: There are physician assistants, there are nurse practitioners, and then behavioral health, you’ve got psychologists, you’ve got psychiatrists, and clinical social workers and all of them fall into this, where they’re trying to build –

Adriana Linares: Healthcare providers, right.

David Leatherberry: Professional practices.

Adriana Linares: And I can respect that from my side of the world which is I often use the term legal professionals, because that also means the legal secretaries, the assistants, the office manager, so all right. What I think is interesting is when you’re talking about — I’m sure anyone who just didn’t know where this was going, listening to this and hearing you talk about doing pro bono work and giving away free advice and helping these individuals that needed help were probably sitting there thinking you were talking about indigent citizens of the community, but you are talking about a middle class, if not an upper-middle class of professionals, who can’t get the legal help that they need to help them do their job, which is in turn helping maybe some of those people that listeners thought you were talking about?

David Leatherberry: Well, that’s absolutely true and it certainly began with the former. In doing work with clients who would come into my meeting, in five minutes after I’d meet with them and because I was dealing with people who struggled with mental illness, I’d come back then and in that five minutes somehow they’d lost all their clothes. I mean they were — very disorganized thought processes, I remember doing hearings where the judge would tell me I hope your arguments going to be quick because your client stinks.

Adriana Linares: Sure.

David Leatherberry: These are — working at that level is very, very — it’s an acute level and where you are dealing with people with just serious levels of illness, poverty, on the streets, finding ways to get by and sometimes in tragic ways, sometimes in completely hilarious ways.


Oftentimes with a lot of self-reflection, understanding that, that other people might be critical of their lifestyle, but then realizing that the people, and this is the point you made, exactly the point, realizing that the people who were working with them and trying to help them, they themselves needed help. And in looking at what I called frontline responders we are doing on a daily basis, I realized there’s no way I could do that for a long-term, and I don’t know how people do it.

Adriana Linares: Yeah.

David Leatherberry: It is the struggles and the crises and the stress that occur and so, I, whenever possible, if somebody wanted to ask me a question, I would do my best to sit, listen and help them find an answer if I didn’t have it. And that’s what started to spread.

And so I became focused, realizing that and it’s not just psychologists or doctors, physicians, but radiologists, community clinics, there are a couple of clinics I worked with up in the Bay Area who work with large populations. But they don’t have a lot of resources, they rely on donors, they rely on grants, they rely on public money and so for them to pay big firm money and that for me, that ranges from my — I remember having lunch or dinner, sorry with three lawyers, with three different firms, each firm, each of which charge over 1,200 an hour.

Adriana Linares: Oh my God.

David Leatherberry: To work with clients and so there are times when that kind of access is — it’s worth that money, if you want a secretary of health, a former Secretary of HHS Services to be an employee, then you’re going to pay that.

Adriana Linares: Yeah.

David Leatherberry: But for most people who are doing the kind of work that I was confronted with, you don’t need that and they can’t pay it.

Adriana Linares: Right, and they shouldn’t pay it.

David Leatherberry: Well, it’s become my little mission.

Adriana Linares: Right, I know. I love that about you, it’s your mission. So in recapping the story or to just — in continuing the story then, you saw this opportunity, but –

David Leatherberry: Well, it’s one thing to put it on paper, and so, over the course of a year, I started kind of thinking this through and asking what-if questions and pulling colleagues, friends, people that I trusted aside and saying, what do you think, how expensive is it. So I started reading some articles that were available actually through Bar Associations about starting this small firm practice what the costs were and putting together checklists of what do I have to expect or what do I need to expect, and what resources do I have already.

And then you have to pick and choose because there are some models out there that are out of the back of your car on cell phone and that wasn’t going to work for me, although I often thought that it might actually work to be what I call the shopping cart lawyer out there working with my client base, almost giving that free advice.

Adriana Linares: Well yeah, that would work, I mean you would fit in to the community.

David Leatherberry: It’s good to blend with your clients.

Adriana Linares: Yeah. So I have a backup question.

David Leatherberry: Yeah.

Adriana Linares: When you started sort of saying to colleagues or other people and specifically, I’m asking you this question about other lawyers that you may have said hey, I’m sort of thinking about going on my own, did you find that most lawyers thought oh my gosh, you’re crazy, you’ve got it so good, that sounds like a lot of work, or did you often hear — I would love to do that, I wish I had either the courage or the resources to be able to do that, what did you hear from your peers?

David Leatherberry: I heard a number of things, none of it negative, and I’ll start with myself. When I — the first time I encountered it, I was with a firm and at this point, I think I was maybe a senior counsel, maybe a senior associate I don’t know, but in that middle tier, lower-middle tier, and there was somebody who’d been a mentor to me who was not yet partner and he walked in one day and said he was leaving and I said where are you going and you always expected someone to be bigger firm, right, right. And sometimes you even would had sort of guess, because you knew the other firms out there and we just sort of traded lawyers at that time.

Adriana Linares: Yeah, right.

David Leatherberry: And he said, I’m going on my own with my brother. He was going to go out and set up his own shop and I remember just looking at him with a little bit of maybe, it’s awe, it was a certain amount of wow, how do you do that.

Adriana Linares: Sure.

David Leatherberry: I mean just how do you do that.

Adriana Linares: Because you certainly didn’t learn how to do that in law school?

David Leatherberry: No, you don’t, and you’ve got bills to pay, you’ve got mouths to feed.

Adriana Linares: Yeah.

David Leatherberry: How was that song though?

Adriana Linares: Yeah, something like that. And we are not drinking.

David Leatherberry: Yeah, and you think about this. You think about all the responsibilities and then you come up with one answer, no way.


Adriana Linares: No way. I hate that answer.

David Leatherberry: And you try to find independence different ways. For me independence was important and that’s just something that was part of my core and so it made firm life a bit of a there was some tension there for me, independence in who I — in the type of case that I took and who I represented, whether I took other work, a number of different things, and you find different ways of doing that and the best way you can do again, niche practices you’re not — you’re going to have smaller practice groups, other people don’t have much to say about your practice and so that’s a way of getting independence is you’re kind of your own practice group in some ways.

And so I like that, but there were still always what-if, and what I found, when I decided to make that announcement, whole spectrum of responses. One, is you’ll be back.

Adriana Linares: Oh, wow. Don’t you challenge me?

David Leatherberry: Well, no it was more on the lines — somewhat an observation of kind of some inevitability, there were a number of lawyers and that had left and gone, done different things and then had come back. And so there’s this sort of idea of Hotel California you can check out any time you like, but you can never leave and at the same time if you do good work and you build good relationships and the firm which and this firm was, you know, they’re good people and a lot of loyalty there and so I think they also wanted just to assure me that if I wanted to come back, the door would be open.

Adriana Linares: Yeah. I was actually going to ask you that. So hearing that did they sort of set a sort of safety net for you mentally even if it wasn’t in the front of your brain, maybe somewhere in the back you just thought, you know what, I can’t always come back.

David Leatherberry: I think that is a bit of a safety net, not that I can come back here, because there’s also a certain amount at least in my mind of — we call it the sort of walk of shame and so you’re back.

Adriana Linares: God.

David Leatherberry: How nice. How was that for you? The dishes are waiting for you in the kitchen.

Adriana Linares: Yeah, we’ve been expecting you.

David Leatherberry: Yeah, there’s that aspect, but also knowing that once you’ve figured out a practice and who the other firms are or players in that market and you know how firms work. There’s a certain amount of confidence that you could go somewhere else, it’s harder because you also look at compensation issues and the biggest — one of the biggest limiting factors is how tied you are to your own compensation structure. Are you living at the maximum level of your means?

Adriana Linares: Right.

David Leatherberry: And in which case it’s hard to move. If you know that there’s a bill that has to get paid and you’ve got to be bringing in a certain amount in order to get it next month, that makes it difficult. I ran into people who had gone out on their own and they were very affirming, they said it was the best and they had some practical advice talking about how there’s a sweet spot at being in a small — being in a very small firm, and then how in their experience how — when they got to mid-size, the expenses started becoming so significant, so burdensome that it made it difficult to function and so they had to give it up and had left their own firms in order to join a bigger firm.

Adriana Linares: Wow.

David Leatherberry: One of the ways that our firm grew so successfully especially during the economic downturn over the past 10-15 years off of my dates, but was that they — there were firms that became financially struggling.

Adriana Linares: And they took them, bought them or merge them 00:33:47

David Leatherberry: Yeah, they were purchased, bought them and merged them.

Adriana Linares: All right to say they just took them.

David Leatherberry: I like the board. 00:03:57 you’ve a certain, certain perspective, the big board the queue travelling through spaceships or— 00:34:02

Adriana Linares: Yeah. That is my experience, the big firm experience too.

David Leatherberry: No, but they, so many of them I think heartfelt — very legitimate heartfelt way said look if you have questions call me or good for you. I wish I could be doing it again.

Adriana Linares: Yeah, such a giving community.

David Leatherberry: But at the same time it is hard to go back to somebody, and take their time and say hey, what do I do, how do I do this and I think the people that you can go back to are far too between, but there was a lot of support that way. Ironically my firm became my first client.

Adriana Linares: No kidding.

David Leatherberry: I left the firm on Friday and Monday I got a call.

Adriana Linares: No way. Hold on, let’s take another quick break from our sponsors before we hear this hilarious story.


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Adriana Linares: Okay, so let’s hear it. You left on Friday, goodbye Kingdom, hello soloness, and then your first call on Monday was the same firm.

David Leatherberry: I think you’re going into a Simon & Garfunkel song.

Adriana Linares: I may have been, this sounds like one.

David Leatherberry: Yeah, so my office went from the 16th floor to my Barcalounger and my commute went from 40-45 minutes to, I don’t know, if that counted stopping in the kitchen and getting coffee.

Adriana Linares: Right, four minutes.

David Leatherberry: Maybe, and I got a call fairly early in the morning, and to be honest and accurate, I mean it was not — there’s not going to be the — I wasn’t sitting there waiting for a call, I had work to do. I left with some of these clients and we can talk about them another time and there was also a significant client that was encouraging me to make this move.

Adriana Linares: Oh really, I hear that happen a lot actually.

David Leatherberry: That was the difference. It was one of those things where I thought okay, obviously somebody is trying to tell me something and if I don’t do this, I just get a permanent neon stupid sign.

Adriana Linares: Yeah, the universe is going to flash.

David Leatherberry: Right.

Adriana Linares: No, it’s not, they’re not even going to flash, that they’re going to attach it permanently.

David Leatherberry: Yeah, right on my forehead.

Adriana Linares: Right.

David Leatherberry: This guy was given every chance in the world and he’s an idiot.

Adriana Linares: As thick as they get.

David Leatherberry: But, sitting there I got a phone call and it was an attorney I had just begun working with there at the firm, a very, very smart guy that I had a lot of respect for who was doing, working with healthcare, larger healthcare systems. And —

Adriana Linares: The ones that can pay $1,200 an hour.

David Leatherberry: Yeah, the ones that — I mean they’ve got more access and it was challenging, it was good work, I could have learned a lot by staying and continuing to work with them, but they needed somebody that was going to continue to service this client for a while. And so, they asked if I could and I was happy to, but the interesting thing is that when you go solo, your rate structure changes.

Adriana Linares: Yes.

David Leatherberry: And they said so what, what’s your rate, what would you want?

Adriana Linares: Well, I hope you at that point as a solo who could control your rate structure decided that whatever you had decided on, on Friday, doubled.

David Leatherberry: It doubled. I think it went past that.

Adriana Linares: Excellent.

David Leatherberry: But, well the point is because from the difference between in-house where you are paying staff and now you’re setting what’s effectively an outside rate, and you’re saying all right, this is going to be a client rate. I am not trying to gouge anybody but at the same time recognizing and this is something I still struggle with, recognizing that, that time is getting spent.

I’m spending it either on that client or on that project or on some other project. And if I give something away then I am not earning that money. It’s lost up, it’s an opportunity cost. And I still tend to be very, very generous and liberal with giving time away too much so, but —

Adriana Linares: You keep saying that, we should work on that.

David Leatherberry: Yeah, we’ll work on that.

Adriana Linares: Okay.

David Leatherberry: Yeah, we’ll get a therapist in here.

Adriana Linares: Yes.

David Leatherberry: But they said so what is your rate and not being smart enough to know better I just said this is my rate, and there was some choking, gagging, and coughing on the other side of the phone and they said, no we meant the rate for us, that’s the rate.

Adriana Linares: That is the friends and family rate fiefdom.

David Leatherberry: That’s the friends and family rate, that’s the discount.

Adriana Linares: Good for you.

David Leatherberry: So we discounted it a little bit more, but it was an eye-opener for me, because I had never known what the firm was paying its independent contractors, and they were seeing me now as an independent contractor and wanted to pay that rate and the way I saw it was, no, I am a specialist, I’m a firm that specializes in a particular area, this is the rate you are going to pay.

And later on that year, when I was working with a healthcare client, the one that sort of went with me wanted me to go and we ran into a very novel issue that really required a number of different looks, second opinions from people who are specialists because this was an area where truly there was no – nothing black-and-white, nothing not even guidance material.


You had to read the tea leaves as to how licensing would look at this hospital and so, we went out to another firm and they didn’t give me a friends-and-family rate. I mean that was one of those $1200 an hour firms, where they said yeah it’s going to be 1,200 an hour.

Adriana Linares: Geez.

David Leatherberry: And so but anyway so, I mean that didn’t last forever, but it probably went on for – it went on for several months and it was — when it was just kind of funny, but it also helped give a little bit of assurance that all right, this is going to be okay.

Adriana Linares: And are they still a client?

David Leatherberry: We’re still friendly but they are not a client.

Adriana Linares: Do they send you business?

David Leatherberry: So it’s interesting, so they don’t, but other larger firms who were peers you might say in that same sort of market tier, have started sending me clients because it’s starting to get out that there are lawyers who can work with small groups and individual healthcare providers doctors as you say.

Adriana Linares: Sure. I like doctor, providers.

David Leatherberry: I mean even doctors — we tend to think all right, they’re making a bunch of money, but they’ve got practices and they’ve got high debts and they’re paying for very expensive equipment and they’re paying for personnel, and the idea of paying large rates or high rates for them is very, very difficult. And prior to going out on my own I was in a number of transactions where I’d be representing say a hospital side and the physicians would fire their counsel halfway through the deal, because they just got too concerned about money and that’s a bit of a train wreck.

Adriana Linares: Right.

David Leatherberry: It’s one thing to switch horses, it’s another to just jump off your horse.

Adriana Linares: Right, no horse needed here. I want to back up just a little bit, so on that fateful Friday, or not so fateful, but fortuitous Friday when you said goodbye to your firm. So you decided to do it, you realized that your health and wellness may have been suffering at the same time that you saw this potential opportunity and you had a client that was encouraged you to go on your own, which is a big deal, to know you have at least one client, whether it was one or a handful because a lot of times when I meet new attorneys or new solos, that’s the biggest question is where my clients come from.

So you were lucky enough to have this client saying let’s do this.

David Leatherberry: Let’s talk about this, I mean that’s a really interesting concern and actually I was going to share with you one point you may have to take this out or put it somewhere else, but one of the things that sort of affirmed my decision was in the day I was leaving, a person came by, a young woman came by and said, she was sorry I was going and it was nice working with me, all those nice things.

And I looked at her and I asked her are you new to the firm, and she said no, not really, I’ve been here I think six months, nine months. Well where do you work? Where’s your office? Across from yours.

Adriana Linares: Oh my gosh, that’s embarrassing.

David Leatherberry: That was embarrassing.

Adriana Linares: Wow.

David Leatherberry: Wow. Well you know, you just stop — you get focused on your work, you get focused on your client and yeah, I hadn’t noticed this. That okay, it’s time for a game change.

Adriana Linares: I live across the hall – right, another one of those moments really like wow, my mind is not where it should be.

David Leatherberry: No, no, no, it’s time to go, and that it actually happened to me a few other times. So I decided all right, that’s another good thing.

Adriana Linares: Well, that’s pretty amazing.

David Leatherberry: So all right, let’s talk about clients because that is — that’s huge, that’s the heartbeat of this whole endeavor.

Adriana Linares: Well I mean ask the technologists at the table and she’s going to tell you technology is the heartbeat of the endeavor, but we’ll get to that, okay, let’s go your way, clients.

David Leatherberry: Wouldn’t you rather say that technology is the brain?

Adriana Linares: I might, yeah, okay, I like it.

David Leatherberry: Okay, well, we’ll leave that out there is a working.

Adriana Linares: We are going to pin that right there for now.

David Leatherberry: Okay, all right so clients, one just in my experience, just my own sort of professional experience, life experience, I’ve firm believer in even the things that you look at and you think are solid you can’t take it for granted. You can’t build a plan around one client or two clients and even with –

Adriana Linares: I mean you can, but –

David Leatherberry: It’s high risk.

Adriana Linares: High risk.

David Leatherberry: Right. I mean diversification and in the type of work that I did, it wasn’t, for example, I had done toxic tort cases where you deal with an insurer or particular large client and they’re going to send you volume work on a long-term basis, so long as you’re doing good work. But the people I worked with aren’t like that. They come when they have a project and they go. And they might have another project in another six months, but you can’t rely on that.

So I couldn’t look at the clients I had been working with over the past six months and count on them to sustain me.


Adriana Linares: So each matter so to speak has a short life cycle.

David Leatherberry: Short life, right short life cycle.

Adriana Linares: Or can’t, I should say they can’t have a short life cycle.

David Leatherberry: But they frequently do. I mean especially with business transactions, which I was starting to do a fair amount of — these are not large systems that go out and do multiple business transactions.

For example, since more recently and since I’ve been out of my own, I have started doing work with a large multi-state healthcare enterprise and they do these transactions on a regular basis, and they’re starting to try to build up — we’re starting to build a relationship.

But most of the ones I did, you do the transaction and then it goes away and they might have some work, little bits and pieces. So again, that’s not something that’s attractive to a large firm. So I had to look not at who of my clients that I’ve served in the last six months are going to stay with me but can this trend, is there evidence to suggest that this trend will continue that there will be other new people who are going to come in the door and that’s a little dicey.

In the first year I looked at it, it was my data pool so to speak, was too small. I said, okay, six months that’s not enough. I put the decision back in a box but after I was able to look at it and say all right over the past two and a half, three years, I could see that there was both a trend that was escalating and there was a pretty strong probability that whatever was happening over the last six months would continue over the next six months and having that additional client who stepped in and said, not that we’re going to be with you forever. In fact we had a long track record of firing counsel.

Adriana Linares: Okay.

David Leatherberry: So I didn’t think this is going to be a long-term relationship although it’s so far turned out to be. But I looked at what were the projects we and how long was that going to take and so I could say I’ve got six months –

Adriana Linares: You had a runway.

David Leatherberry: Yeah.

Adriana Linares: Yeah.

David Leatherberry: Yeah. There was a runway.

Adriana Linares: It reminds me of when I — so I was at a big firm too.

David Leatherberry: Yes.

Adriana Linares: Yes.

David Leatherberry: How was that, tell me about it.

Adriana Linares: Yes nobody wants to hear about me but I’ll say this real quick. So yeah, I was at two big Florida firms and decided to go out on my own but not knowing when and I got a call from a firm who saw me speak and said, hey do you know anybody who does what you do? We need someone for eight weeks in Savannah, Georgia and I did that I said, well here’s at least a client for eight weeks and surely another one will come along, that gave me an eight week window to find more clients.

And then sounding like what you’re about to say, they just kept coming because there was so many law firms obviously, but it worked out but that was the important part was at least having that runway, that safety net for x-number for you whether it was dollars or months and for me, it was specifically eight weeks but then it worked out but that made it easier for me to decide to go out on my own.

David Leatherberry: That’s exactly it. For me at least my experience was not that this is forever or even two years. It was – all right I can look out say three, six months and I’ve got reasonable assurance that I’m going to be okay over that period.

Adriana Linares: Right.

David Leatherberry: I may have to start looking for part-time work or go down and start practicing my – do advice with that towards the end of it but and then what has happened is there’s just somebody new, and sometimes when I start to get depression, I feel anxiety about workflow or start to get down or I start to — sometimes I’ll be resistant to finishing a project because I don’t want it to be over, which isn’t a good thing. It’s part of procrastination and I have to remind myself that wait a minute, next Monday, there’s a pretty good chance between Monday and Friday, somebody’s going to call and need something new and so far that hasn’t let me down.

Adriana Linares: That’s great. Of course like we said, I said a minute ago the biggest fear I hear from new lawyers or new solos is that like where will the work come from and sometimes, it takes a little longer but just believing and I tell lawyers this all the time, you’re going to be fine. Just believe that the clients are going to be there, that you’re going to find them and they’re going to find you and I mean you can’t do it thinking they’re not going to come around, I mean then you would never take the leap. So you just got to believe.

David Leatherberry: It’s interesting. I don’t know if you believe, I mean maybe I’m reading too much into it. You’ve got to be willing to jump in the face of doubt. It was a year ago, I was in Colorado and with my son, we’re doing some rafting and they pulled the rafts up to a wall, cliff wall and said that this is where they all invite – where they invite people to go cliff jumping.

Adriana Linares: Oh my God.

David Leatherberry: And I am 50 – I was 56, it was still this year I guess and so, I thought you know and I’ve never done anything like that in my life. I’m going to try.


Adriana Linares: You are going to try.

David Leatherberry: Why not? I thought okay, I’m going to give it a whirl, it wasn’t a huge cliff okay. Huge, it may not look huge from the bottom looking up but when you stand on top looking down it’s a big — it’s a different thing. And the reason I bring this up is because there was a desire, a strong desire in me to do it and at some part of my thought process, I realized that intellectually at least, there was a strong probability that it was going to be okay.

And so, when I went out and stood on the edge and looked down and my knees immediately went soft and my feet started to tremble. I said, okay, this is just my reaction. It shouldn’t necessarily stop me and so, I just backed up and decided I wasn’t going to look as I went off and just jumped and it was fine.

Adriana Linares: Of course it was.

David Leatherberry: It was fine. There’s always risk and somebody once also described to me that courage is the willingness to accept fear or to take action in the presence of fear. And I think that’s exactly what it comes down to.

Adriana Linares: Yeah, for sure, it’s courage. Sometimes, you have to find it. Well I think it’s been a really fun intro episode to our series of Your Law Firm Makeover, which we haven’t even gotten to talking about how you actually did it aside from deciding that you were going to go out on your own, telling everybody leaving your law firm, setting up shop in your living room, having a client, getting a client but when we come back in our next talk we’re going to talk about the logistics.

David Leatherberry: Okay.

Adriana Linares: And the decisions that you made about technology and marketing, you’ve got a — let’s see how long have you had that awesome new logo that I like so much just a couple of weeks.

David Leatherberry: Couple of weeks.

Adriana Linares: Yeah so we’re going to catch up more and more and talk about this again in our next episode but before I let you go, we didn’t do a very good job of introducing you from the beginning because we just started yapping as you and I do.

David Leatherberry: Yeah.

Adriana Linares: So tell listeners a little bit about yourself insofar as I mean we can surmise and figure out your practice area but tell me your name, where you practice, the specialty that you have, if you want to talk about that, and any other information you want to give them.

David Leatherberry: So I am David Leatherberry and the law firm is as of just a few weeks ago, Leatherberry Law, A Professional Corporation and I do healthcare, healthcare law, it is not exclusively, it’s all — at this point now, it’s all healthcare, all working with providers, most of it is behavioral health that’s been a very strong niche, but that certainly expands into other areas of practice from physical therapy to physicians, OB/GYNs, most of it is on the transactional side. I do a lot of advice, counsel work, regulatory work and there’s a vision there which I’m sure we’ll talk about.

Adriana Linares: We are going to talk about that because that’s one of the things that I love about you so much is the vision that you have for providing broader scope of services at an affordable and tech savvy way.

David Leatherberry: Yeah exactly.

Adriana Linares: Well great. I’ll see you next time.

David Leatherberry: It’s been a pleasure.

Adriana Linares: Okay listeners, I sure hope you enjoyed getting to know David Leatherberry. He will be back in future episodes of New Solo to tell us more about his law firm makeover.

I want to thank you for listening to another episode of New Solo on Legal Talk Network. Don’t forget if you like what you’ve heard today, we’d really love a 5-star rating from you on iTunes and of course, you can always email me with any comments or questions you have about the show [email protected]. If you have any suggestions for topics for — if you have any questions, you can email some questions.

One of these days, I’ll do a question and answer episode, just need to get so those questions lined up. So think about that, communicate with me. I’m available and always happy to hear from you. We’ll see you next time and remember, you’re not alone, you are a new solo.


Outro: Thanks for listening to New Solo with host Adriana Linares. Tune in again to learn more about how to successfully run your new practice, solo, here on Legal Talk Network.


The views expressed by the participants of this program are their own and do not represent the views of, nor are they endorsed by Legal Talk Network, its officers, directors, employees, agents, representatives, shareholders, and subsidiaries. None of the content should be considered legal advice. As always, consult a lawyer.


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Episode Details
Published: June 25, 2019
Podcast: New Solo
Category: Best Legal Practices , Medical Law
New Solo
New Solo

New Solo covers a diverse range of topics including transitioning from law firm to solo practice, law practice management, and more.

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