Branding and Surviving in the Legal Support Sector with Ross Guberman
In today’s episode of Lawyerpreneur, we talk with Ross Guberman about his career in the legal support sector. Ross built his consulting business from the ground up and was eventually able to leave his law practice and job as a law professor to work for himself full time. Having survived the recession a decade ago, Ross shares insights on persevering and persisting through difficult times.
Ross Guberman has built career from the ground up as the founder of his consulting business Legal Writing Pro, author of Point Made and Point Taken, and the creator of BriefCatch. In this interview, we discuss Ross’s departure from law practice and his entrepreneurial journey.
Creating a Brand and Surviving in the Legal Support Sector with Ross Guberman
Jeremy Richter: Welcome to the Lawyerpreneur podcast where we explore how having an entrepreneurial spirit helps us fill our creative wells and excel in our work, because being a lawyer doesn’t have to mean doing business as usual. My guest today is Ross Guberman – best-selling author of Point Made and Point Taken, the founder of Legal Writing Pro, creator of Brief Catch, award-winning journalist, international speaker, and adjunct law professor. Ross, welcome to the show.
Ross Guberman: Hi, good to be with you. Jeremy.
Jeremy Richter: Did I get all of the accolades there? Because I didn’t want to miss anything.
Ross Guberman: Yeah, you did maybe hype the hype them up a little. In fact, you’re sitting here sitting here in a basement room, looking at the four walls.
Jeremy Richter: Well, did you sound impressive to yourself as I read it, though?
Ross Guberman: Yeah, sounds a little bit alien, actually. But I’ll take the compliment. So thanks.
Jeremy Richter: Alright, so what we’re here to talk about is lawyers who are also entrepreneurs, and you fit well within that category. And so I just want to talk about your entrepreneurial journey, and how you got started and where you are now and what else going on with your different businesses that you’ve got going. So how did you get to law school? I know it’s a little bit different journey for everybody. So how did you get there?
Ross Guberman: So it was it was actually a little bit random. I was doing a Ph.D. program. And I got, I got tired of it fairly quickly. And I was doing it at Yale and I knew a lot of people at the Yale Law School who said that they could see I was a little frustrated with academia. And then I seem to be interested in what they were doing. So why didn’t I Why didn’t I just take the SAT and go to law school and it seemed like a pretty good exit strategy, and I did, but I was told that I just ended up in law school. So very, very quick, very quick and not very well thought through.
Jeremy Richter: Well, that sounds really familiar to me. Before I went to law school, I was a high school teacher. And I had done a master’s in history and was preparing to do a PhD in history. And then I just kind of decided to apply to law school and did that instead. Also not very well thought out.
Ross Guberman: Yeah, but you, you are two years ahead of me and you’re thinking right, so I wasted two more years than you did in life but I accepted that.
Jeremy Richter: Yeah, that’s about all you can do at this point. So when you went to law school, did you think you wanted to practice law? Did you have anything particular in mind?
Ross Guberman: Even more than most people I really, truly had no idea what lawyers did. And I didn’t know anything about the law. And other than the students that I knew from Yale, I didn’t really know any lawyers. So I, I certainly suppose that I wanted to practice law. And I liked law school. I liked the subject. But again, I didn’t really, I didn’t give it a huge amount of thought until it was time to be a summer associate. And that was my first exposure to the practice.
Jeremy Richter: And so what did you after law school? What kind of practice did you end up having?
Ross Guberman: I went to a huge firm Latham and Watkins in the Washington office for not too long, less than two years. And then I left and I did a bunch of things, including starting to teach at GW Law School. And although I had some non-practice related activities, I also edited briefs and wrote briefs for different firms as mostly a palette, a little bit of trial, as well. So I did that for a couple of years. After not being a full time associate anymore.
Jeremy Richter: So at some point, you also did journalism work. Where did that fall in?
Ross Guberman: Actually it was right around that time I was kind of trying to find myself and as I said, I did some legal work and I taught at law school and then I worked as an investigative reporter. all at the same time. I was also doing a little bit of translating. So I did I did some pretty hefty stories like kind of long form journalism that’s not quite as popular now for a couple of years sporadically. So actually, a lot you meet some people who do journalism and then go to law school actually did get it a little bit in reverse.
Jeremy Richter: Alright, so at some point, you start writing about legal writing and spending a lot of time with that in certainly now that’s, I think probably what people best know you for how did you start going that direction?
Ross Guberman: So wasn’t it wasn’t even really my idea to tell you the truth. So as I mentioned, I wrote briefs and edited briefs for different firms. And one of the partners and one of the firms suggested that I put together a class for the associates at her firm. And it was pretty, pretty casual. But I agreed to do it, obviously. And that’s kind of how the whole thing got started. I mean, I was also teaching at GW Law School, as I mentioned, but it was really her idea that I take all this and turn into some sort of business. So at the same time, I tried to get a business going, which of course is not easy, and I also worked hard to get more attention for my written work. So I had some journalism prizes for those articles I mentioned before and then I started writing about legal writing. And I just got very lucky I wrote an article about that. Chief Justice, back then, “Five Ways to Write Like John Roberts” and Oxford University Press editor found the article and gave me a book deal. And that’s sort of how it all got going. So kind of parallel tracks writing to get recognition, and at the same time just trying to get this training business off the ground.
Jeremy Richter: So what did you do in trying to get the training business off the ground? How did you go about getting your name out there for that, and just bit constructing that business from nothing into what it is now?
Ross Guberman: Well, it was certainly tough as you would expect at first. I mean, there are obviously legacy players in this kind of market of trading lawyers on X, Y, or Z. So I had that problem. Plus, I was pretty young and I didn’t have a lot of practice, and many years of practice behind me. So I would say it was a combination of credentials, also the post that GW Law School, and also just early word of mouth, from the relatively few firms that hired me at the outset. And I also, I also had a lot of hunger. So I didn’t give up and you get a This is, of course an error of different technology, with email, not really even that great, but of course, you get a lot of ignored emails and calls, you just have to sort of persevere and hope that you know, you hit a tipping point with clients where they start to spread the word, and then you’re, you know, then you’re in a much better position, but that took that took it probably close to two years.
Jeremy Richter: So what time frame are we looking at?
Ross Guberman: So I left the firm kind of during the, you know, the dot com craze, so around 2000 so this is more like 2002 by the time that I that I really had things get started business wise. But I always I always thought it would be a sort of a part time thing during the training, and that I would have to find some other, you know, more reliable source of income, but it ended up not happening that way.
Jeremy Richter: When did it work out that you could go full time with it?
Ross Guberman: Well, the thing about law firms is they, they tend to travel in a pack. So, I mean, I once did try to figure out the date, but there’s probably a day or a week at least, where’s all the sudden enough firms here that you’ve, you’ve done training for their peer firms that all of a sudden they sort of all want to hire you at once? So it was a little bit a little dramatic, though. I would say even, you know, one month to the next one month, I was still wondering if this was really gonna last and then the next month suddenly, you know, I was getting inquiries from 25 or 30 firms.
Jeremy Richter: So I am a person who’s pretty risk averse. And that sounds both exciting and terrifying. To have that kind of imbalance – I don’t know if it’s an imbalance as much as it’s an undulation. Was it exciting in that in the moment? Or was it? I don’t know. I didn’t know what your family situation was at that point…
Ross Guberman: Probably not ideal, you know, two little kids and a wife working as a doctor, so certainly you, you know, if you if you leave a job, you know, along the lines of being an associate at a huge law firm, you’re gonna raise a lot of eyebrows and people are gonna wonder, you know, what you’re doing and whether it’s responsible, and I and I sort of agreed, so I think I gave myself you know, a time limit of, let’s say, three years, and then if all else failed, I would just go back to practicing full time. So yeah, there’s no doubt about it. It’s, it’s, uh, it is exciting. But, you know, you have, obviously, some disappointments and some days where you’re really wondering if everything is gonna fall into place. And you have to just sort of manage that. And as you said, you have to have whatever tolerance for risk you do have and work within that. So I think I could be telling the same story now and could have ended, you know, in some sort of, I don’t want to say failure, but something close to failure, and I would have probably still been glad that I’d given it a shot, but I would have had to find something, something else to do.
Jeremy Richter: Sure. Was there a singular moment where you thought, “Okay, this is gonna work”?
Ross Guberman: Yeah, I mean, I think you either make it or you don’t in this kind of business. And if you do make it you can tell because you just you get a certain type of reaction from the associates at these firms. And you get a you get an increasingly comfortable feeling. And you start to get excited every day about getting up and going to affirm and I, and once you once you hit that point, of course, you have renewed confidence and then it just self-perpetuates, because you’re getting good vibes and you’re getting more sure of yourself, then that probably translates into inspiring more confidence as well.
Jeremy Richter: So you’re into, I guess you’re closing in on nearly 20 years of this kind of work. Is that still exciting to you? Is it still like fun to go into a new place and provide education and training folks?
Ross Guberman: Well, of course right now, I’m not going anywhere except, you know, sometimes I go up a flight of stairs, or down or stick my head out the window. But it’s you know, I’m actually a little bit embarrassed to admit that it is still exciting. I don’t I don’t want to exaggerate. I mean, I Certainly had days, you know, waking up in the middle of the winter somewhere in the heartland and not, you know, not being as excited as I might have been earlier for every single workshop, but actually I enjoyed the interaction and I love my topic. Mostly, I’d say that that sort of passion has been pretty steady.
Jeremy Richter: So people who, like me maybe, or who are listening might assume that someone in your line of work is a really extroverted person who just loves surrounding yourself with people and is energized by the engagement. Is that true? Have you or are you more introverted and need time to recover? After doing a seminar for a few days?
Ross Guberman: When I was younger, I would say I was probably an almost an extreme extrovert, where I really got an endless charge out of speaking in public and interacting with strangers and, you know, hopping from city to city, I think sometimes as you get a little older that naturally dwindles a little bit. You know, as a matter, of course, I do think it helps, at least on the margins can be somewhat extroverted only because a lot of what makes for success is not really raw quality. So there are other people who also know a lot about legal writing and are very good at teaching and teaching it. But they don’t have the kind of the business sense or the ability to make connections with clients. So it does help. On the other hand, I could think of consultants right now who are incredibly successful who are not extroverted. And they make their business connections in just different ways that are just as effective at least for them. So, yes, I am extroverted. But I don’t I don’t think it’s essential to succeed in in business.
Jeremy Richter: Yeah, I agree. I think everybody’s got to find Know what works for you. And I think in a law firm setting, like I man, I have an insurance defense practice. Most of the lawyers that when I was a young lawyer were either training me or that I was observing worth more introverted personalities and had one way of marketing that really worked for them. That didn’t work for me. And I had to kind of find my own path to what was sustainable and manageable for me. And I think that’s lost on a lot of folks that don’t get training that way.
Ross Guberman: Yeah. And it’s, it’s always fascinated me then on the on the Myers Briggs, I think 75 or 80% of lawyers are introverts, not extroverts. And it doesn’t really even correspond to practice. So even, you know, even trial lawyers are generally introverts on Myers Briggs. So you and I are sort of the outliers, which maybe explains why we’re talking to each other right now.
Jeremy Richter: Yeah, for sure. You can capture everybody’s attention and I can be a good listener.
Ross Guberman: Yeah, I actually have their 16 types and mine is ENFP. And I someone told me years after I finished law school that that’s the type associated with not being satisfied in law firm practice of all 16. So, in that soil I you could have could have saved me many years ago, but luckily, it all worked out. I’m in a perfect job for an ENFP.
Jeremy Richter: Well, good. Honestly, I haven’t ever done the Myers Briggs. The only personality test that I’ve ever done is the Enneagram. Are you familiar with that?
Ross Guberman: Yeah. Okay. So anything scandalous come out of that, or did you get a good result?
Jeremy Richter: No, but it helps explain a lot to me. That like I didn’t under internally, you know, within my own headspace that I didn’t either recognize or didn’t have words for before. I tested as Three with the four wing, which if people that aren’t familiar with it is kind of what they describe as an achiever and a person who’s really internally motivated to accomplish things. And then the four is more of an artist bent. And so whenever I
Ross Guberman: interesting mix, right?
Jeremy Richter: Yeah, yeah, it’s not always great. But now I understand things that I didn’t understand before. And so like, when I started my blog, and I would do all these other things and tell my wife about all these ideas she had, she would ask on occasion, and not in a critical way, just more of like, she’s not, she’s not bent this way at all. She would say, “Why can’t you just, like be a lawyer?” And I for a long time, I didn’t have an answer other than I knew that, like, I was just driven toward these other things. And then once I started learning about the Enneagram, and being a three I was like, okay, this is like I this is just how I’m created. And this is how I’m wired. And all of these other things are just a part of my makeup and then she read about it and started understanding things about herself. And we’ve used it to communicate better with each other.
Ross Guberman: Like it’s like an affirmative defense but for marriage, right? If someone’s frustrated, just say, Sorry, just look up my type. I can’t Yeah, that’s right. I can’t help. That’d be gotta be daydreaming. It’s in my, in my blood.
Jeremy Richter: Yeah. And so, but as far as all of these personality things, I think the best way that I’ve utilized it, or found it practical, is in not just understanding myself, but also in using it to understand how other people need to be communicated with so that I can do that more effectively, hopefully.
Ross Guberman: Right? That’s right. Yes. There isn’t really are right or wrong, just a matter of styles. But at the same time, you have to, at some point be true to your own style too. And you know, we all have that push and pull where we’re trying to adapt to other people hoping that they can adapt to us. And somehow you hope that you meet each other halfway.
Jeremy Richter: Absolutely. All right. So I think one of the really cool things that you’re doing right now is Brief Catch. And before I ask you any questions about it, I will tell you, and I think I either emailed you about this or tweeted about it, I don’t recall. But for my most recent book that I just launched, Level Up Your Law Practice, I used Brief Catch as my line editor to help just all the writing improve and be better. And I’d used it before and I used it for this, like I became a true believer, and I will tell everybody about this product, and I just think it’s amazing.
Ross Guberman: Well, thanks and congratulations on the on the new book too.
Jeremy Richter: Well, thanks. Alright, so tell for anybody who doesn’t know what is Brief Catch.
Ross Guberman: So Brief Catch is a is a plugin that, as you said, functions as, you know, an automatic line editor. So it takes a draft and it looks at it depending on which option you choose from the perspective of style. So we’ll make a lot of style suggestions and you can choose and then we’ll tighten things up and kept some errors that other checkers don’t catch. It also checks for consistency. If you have one space, generally after periods that you have to it’s going to flag that are things in bullet pointed lists, or if you say toward and then towards, and then I also have it flagging different parts of the persuasive enterprise to so it’s going to tell you that you’re using, you know, six or seven cases in a row, probably for the same point or it’s going to notice that Your transitions are repetitive. So it’s an interactive tool, it gives you choices for many of the edits. And then there are some explanations as well. So it’s supposed to help you write more effectively and get your own points out better, but also has some sort of, I hope, you know, teaching value to. So that I think, yeah, that’s good, I think.
Jeremy Richter: Yeah, I think it definitely does. Like if you’re paying attention to what it’s telling you and for me, you know, over the course of 200 pages, it would tell me the same thing over and over as it caught it. Like if you’re paying attention, I think it absolutely has that teaching value, or at the very least has the capacity for it.
Ross Guberman: Yeah, I mean, I sometimes argue with that myself, you know, like, “Hey, leave me alone. Remember that I’m the one who created all the algorithms.”
Jeremy Richter: So how did you come up with the idea for this?
Ross Guberman: One, well, it’s gonna sound like I don’t have again, any ideas on my own, but that’s actually again the case. So it was really all the people in the workshops and some judges who would say over the years that they loved all the things I was teaching, but it’s impossible to remember all of them, let alone, you know, invoke them, and apply them when you have other things on your mind. So I finally heard that enough times that I thought I would take the plunge and, you know, go into the tech world. And, of course, it took a while took a couple of years to get it, get it ready to market. And been it’s only been out for two years, but I’ve been, you know, working on it. Ever since. We tried to improve it enhance it just launched a 2.0 version a couple of months ago.
Jeremy Richter: Have you been — I don’t know what your expectations are — maybe you don’t know what your expectations were at the launch — but how is it gone over the course of two years?
Ross Guberman: Extremely well. I mean, you know, a lot is really frightening. A lot of things can go wrong, and a lot of technical things can go wrong. And luckily, I’ll knock on wood here silently. We didn’t have any of those types of issues. It’s, you know, I did expect that it would take up a lot of my time, and it has, so that, you know, that part is matched expectations. It’s probably penetrated more markets than I would have expected. So for example, a lot of courts use that a lot of judges use it, even some justices on the Supreme Court use it. That’s a nice surprise. And it’s also just especially now starting to kind of go on the other end into the law schools. So that’s all been good too. But no doubt about it. It’s a huge amount of work. And it you know, I probably underestimated how much work it would entail after the initial launch.
Jeremy Richter: Yeah, that makes sense. What is different about 2.0? So what’s the biggest change you’ve implemented since launching it?
Ross Guberman: Biggest change is that you have three modes Now, depending on your, on your needs at the time, so you can focus only on automatic style edits, you can focus only on mistakes, certain consistencies, if you want if you’re under time pressure, or you can actually do all of the above and more. So that’s a huge difference that people so far have been really excited about. And then the other is really more of, I think, a natural progression with technology for professionals, just a completely revamped interface that’s much easier to use and gives you more choices. And I also have an AI component now so the choices are there. You could have you know, 810 options for the same edit, but they’re ordered according to the rates that word or phrase appears in the writing of the best lawyers and judges. So there’s those three things, the three modes, new user interface and the AI component for some of the options.
Jeremy Richter: Well, I know that I’m a nerd about these sorts of things. I think that’s super interesting. And so…
Ross Guberman: No, it was a new world for me. I didn’t know anything about UI’s and so forth.
Jeremy Richter: Yeah. I assume you had a lot of help along the way.
Ross Guberman: Yeah, I mean, it’s, you know, you have to of course, find the right developer. That’s pivotal. And then, you know, you end up having to give other types of advice, user experience, user interface, for example. But a lot of the users have given me Good, good suggestions to or requests, you know, can you catch this Can you catch that? It’s funny, I just noticed I’m sure it’s connected to the times. People are people have written me saying I’m so glad you catch a HIPPA/HIPAA misspell. Really. It’s very gratifying to get, you know, the actual users of your product to give you ideas to and not just people you hire and pay as consultants.
Jeremy Richter: But it was when you said a few minutes ago that you don’t have any of your own ideas. I read a book A few years ago, called Bandersnatch by Diana Glyer, and it’s all about JRR Tolkien and CS Lewis and their little group of writers called the Inklings and how important collaboration was to all of their work and how they met every Thursday, I think it was for years and would read each other’s work aloud. And so in terms of their ideas, just from those sessions, and, you know, there’s the idea that CS Lewis and JRR Tolkien specifically, were very individualist and wouldn’t listen to anybody. But her book shows how all the collaboration was so important to making these great works of art. And so, you know, the same is true with legal tech or writing or of any kind, that taking the ideas of others, and actually applying them is what makes any of us able to create.
Ross Guberman: Yeah, and I mean, I don’t have anything formal the way these authors did, as you described, but I’m certainly someone who loves to go up to people and ask for advice or ask for their thoughts and, and then, you know, take what I hear too hard, and I think that’s been invaluable over the years, not just for safe cats but for my workshops as well. And also I’ve gotten a lot of ideas on marketing and sales for, for my workshop business and the tech business just from listening advice.
Jeremy Richter: Yeah. And that can be difficult. I mean, I think it takes a certain amount of self-confidence to go out and seek that information and no, have the self-awareness to know what your limitations are and what you need to approve. And that is not an easy thing.
Ross Guberman: No, it’s not an unfortunately, it’s especially hard when you’re starting out when you have the lowest amount of confidence. So when I remember, as you said, making me feel old, 20 years ago, I started doing workshops, I used to be afraid to even read the evaluations, I was so petrified that anybody would say anything negative. And that’s, of course, the time when you really need the most feedback. Then when you get successful, you generally are more open to suggestions. And at that point, although it’s helpful, it’s not, not as you know, not as crucial as it is when you’re starting out and maybe two hypersensitive?
Jeremy Richter: Did you find yourself when you would read the evaluations able to apply the feedback that you were receiving and make the changes?
Ross Guberman: Yes, I mean, I think by definition, you better do that. I mean, you better figure out what the audience wants and what the patterns aren’t what they want, or else and I, and I did. I did, of course matter, you know, no matter what you do in a training situation, or frankly, any situation, someone’s not gonna like it. So what you really have to do is, you know, learn to discern what, what patterns are going on and the feedback, both positive and negative, versus just the sort of outlier comment that you might be inclined to take a little too seriously. So yeah, I mean, I, I remember getting really good feedback on you know, just that I talked too fast, and I probably still do. I mean, that was something That I worked on at the start, and that I, you know that I covered too many different techniques or issues and a three hour period. So those were very those were very concrete and those were things that helped me a lot.
Jeremy Richter: So we’re recording this on April 2, we’re in the midst of the Coronavirus pandemic. There is already news coming out about law firms that are reducing salaries that are preparing for layoffs. And there’s just a lot of tumult in the legal sector at the moment. How does that affect businesses like yours, I guess you were around for 2008 and the recession that hit then. I don’t I don’t know whether it will say anything like that. But you’ve seen what a recession can do to businesses in the legal tech and legal sectors. are adjacent to law firms. What do you think? What are you looking at?
Ross Guberman: I was — oh, by the way — also around on September 11, that was right around the time that I made the transition into consulting. So I would never want to minimize what’s going on, even though we don’t have anything close to the answers that we would like to have. I will say, though, is that as you mentioned, I was around in 2009. And I remember the panic and the nervousness not just in the profession in general, but in my niche of consultants. And, you know, frankly, a lot of it was justified. I mean, there were there were there was cost cutting back then and there, you know, downsizing, and the like the one, the one thing I would say, I would carry from the 2009 experiences. I think people should be cautious before believing that everything is going to change and the professions never going to be the same and they’re going to be just dramatic, just impossible to imagine shifts in how lawyers practice. First of all, I’ve actually been hearing that in different forms and with different degrees of certitude for 20 years, right, the billable hours gonna go away, lawyers are not these firms are not gonna be able to survive, and that neither of those things by the way has happened. So I would, I would, you know, people who are completely freaking out and I’m, you know, I’m close to people who are, I would just say, don’t be, don’t be so certain The sky is really falling in the profession. So there’s that. On the other hand, you know, this is probably a great time to build skills, it’s a great time to learn. It’s a great time. as horrible as this is in so many ways. It’s a great time to reconnect with colleagues or clients and spend more time communicating with them. And certainly from my own vantage point, I would say, this is awesome. was going to be a really exciting time for legal tech. Because, well, there’s necessity. But again, I also think there’s a jolt going on now that’s going to make people realize that they can adopt a lot of these tools and incorporate them into their workflow much more easily than they imagined. And all you got to do is look at how fast law schools and firms have adapted are ready to, you know, remote work. I mean, it’s actually really encouraging.
Jeremy Richter: Yeah, so I’ve been working remotely for two and a half weeks now. And I had always, I mean, since I started practicing in 2012, my firm has enabled me to work remotely. And so I’ve always worked remotely, like I’ll just work in the mornings before I go into the office so that I can leave at five o’clock, you know, every day or as close to it, you know, that’s not a given right now schedules and whatnot. But that’s, that’s my you know, that’s how I work around it. I don’t want to be there till seven o’clock. So I work super early and just kind of flip the schedule a little bit. But now, everybody in the firm is working remotely. And it’s almost a seamless transition. It hadn’t Well, maybe not seamless, but everybody’s doing it at work able to be productive. Yeah, it’s working. So I agree with you, there’s a lot of malleability of people that sometimes we don’t give ourselves credit for.
Ross Guberman: Yeah, I mean, I think the technological part and the logistical parts, they have both gone much better than a lot of people would have expected. I would imagine that the real challenge is not going to be logistical or technological. It’s going to be, you know, psychological as the, you know, you mentioned two and a half weeks if this becomes two and a half months. I think that’s gonna be the challenge. Yeah, I agree. Yeah that’s gonna be the challenge that we all have. Well, we will all have to deal with our selves.
Jeremy Richter: And you did mention something that I’m excited about is the amount of creativity that may that I think we’re already starting to see arise out of these changing circumstances. And certainly that’s been true for me. I’ve been thinking about doing this podcast for a long time. There certainly some fear behind doing it and stepping into something that I’m uncomfortable with, and uncertain about requires a certain amount of, you know, just accumulating knowledge to be able to do it. But now I have the time, like, I can still get in 8-9-10 hours of work a day, and I don’t have a commute. And so I was able to put a little bit of extra time into figuring this out and starting it. And I have seen other people do similar projects where they’re saying, Look, I’ve been able to do this now because I’m home and I can do this. And I’m hopeful that, you know, not just in the legal sector, but in our broader communities that we’re going to see created activity and developments that we might not have seen otherwise.
Ross Guberman: Yeah, I mean, that’s, you know, that would be fantastic. And much appreciated. byproduct of, of this situation. And I, I guess the question is, how can we, how can we harness some of that and try to get some positivity out of our predicament and while still managing anxiety, I think that’s the challenge, right? It’s you can’t, you can’t really proceed as everything is, as it usually is. But on the other hand, you don’t want to be you don’t want anxiety or even curiosity about the news to inhibit you and not allow you to, as you’re saying, pursue some of these projects that we now that we now are actually in a good situation to, to bring to fruition.
Jeremy Richter: Alright, so I’ve got a couple of questions for you that one of my friends over at LawyerSmack when I told her I was doing this interview, she said, “I have three questions, I need you to ask Ross.” What is one rule of legal writing that every lawyer should implement immediately? I was gonna say maybe not starting your pleadings with “Comes now, the defendant, blah, blah, blah.”
Ross Guberman: Yeah, I mean, I think that that ship has sailed people already, they’re gonna do that or not. What i what i would say, you know, on the topic of things people can maybe think about a little bit when they’re home. I would say the one rule or I’ll call the guideline is, make sure you’re noticing when you have several sentences in a row that begin with further or Furthermore, or Moreover, or additionally, and take another look and ask yourself, Am I really listing something And if so convert those to first, second and third and explain what exactly you’re listing. And if that’s not the case, then you want to revisit the sentences and look for some kind of gaps in the logic so that that would be something for people in all practice areas just looking for more opportunities to convert a series of vaguely related thoughts loosely connected with lame transitions, like further and furthermore into a numbered list. Or if that’s not possible, figure out what the heck is going on in your analysis. And if there’s a clear way to make the point stick together.
Jeremy Richter: Do you read your own writing out loud to try and catch those things for yourself?
Ross Guberman: Well, I do even though I yell at Brief Catch, I use Brief Catch on my own writing by the way, that is actually true. I do use Brief Catch, but I do also believe in reading out loud or at least, you know, sometimes it’s awkward to read out loud, especially now that we’re all at home with different friends. remembers, you can get close to the same effect by simply hearing the words articulated in your head, even if you’re not, you know, mouthing them and voicing them. So no doubt about it. That helps. Which is one reason in the, you know, the 20 year ago period when back then I know it’s hard to believe a lot of the partners still dictated into recording machines that you’d now see only in museums, writing with no better that’s much better. Yeah, that’s it. That’s good. I mean, people really did write better decades ago, and even better than that 30 or 40 years ago,
Jeremy Richter: So I’ve done it some but just with my iPhone, you know, with in notes, I’ll start dictating stuff. I’ve done it some for fiction writing, I’ve done it some for just I’ll have ideas as I’m driving down the road and just want to talk through them because I know that if I don’t in that moment, get it down, then it’s gone forever. And so, if there is a difference between what I dictate and what I type. And yeah, notice,
Ross Guberman: Yeah, it is and I mean, it’s great that voice recognition technology nowadays is quite good, right? So you’re not just you’re saving yourself a step you don’t have to go back and listen to the recording and type it out. Right? Not bad.
Jeremy Richter: Alright, so what is something that makes your soul shrivel when you see it in a brief or an opinion?
Ross Guberman: So one, here’s how I would answer that one. One way to stay sane in my business, but also to impart or follow. The very advice I impart is to make sure that I never have my soul shrivel, or I never really get upset or I don’t have pet peeves. And although that might sound like a cop out it it matters to me because I think when people praise Legal writing or criticize it, they’re very often focusing on a word or a phrase or a sentence, in a, in a opinion or a brief, when really what matters is kind of holistically how the whole thing comes together. So there, honestly, I swear, there’s nothing that I ever read that actually makes me you know, sick or upset, or, or, you know, threatening my soul. It’s more the aggregate. There’s sort of an aggregate effect sometimes where I will feel like this is someone who’s not really maximizing his or her potential because the words are actually distracting from the points instead of making them but there’s not any one thing though that I think is, you know, fatal, or sinful.
Jeremy Richter: Yeah, that sounds like the healthiest approach for you.
Ross Guberman: Yeah, I mean, otherwise a Mac. I mean, you also you would just wouldn’t want to go through life. criticizing everything you saw, right? I tend to try to ignore it. Unless I’m being paid to read it or I read just as everybody else does. I just read for content and I try to, you know, move on, not dissect every single thing I see.
Jeremy Richter: Alright, the last question is, how do I break my boss’s terrible writing habits got anything for that one?
Ross Guberman: Triage, you know, triage. So, again, when I’ve heard that, and I do hear it a lot, it usually comes down to one or two power struggles, you know, and at that point, generally you have to sort of give in a little bit while still preserving and making you know, practicing your own your own thoughts on style. If you do not feel like you can let it go though, I found that two things work and only two things. Because otherwise, as I said, it’s a power struggle. And if it’s a boss, you’re going to lose the power struggle. So the two things are one the most Effective with bosses, show them famous lawyers or famous judges doing the very thing that you want to do that the boss is not doing. That’s of all the things you can do the most persuasive although I’m certainly not going to guarantee that it will work. And the other is if it’s some kind of a spat over usage or you know, grammar or wording. Try to find something so authoritative the boss won’t be able to dismiss it, you know, like the Chicago Manual of Style or something. And not you don’t want to do it in a godly way. You just want to say, you know, I know we’ve disagreed on this matter, I just thought it would be great, you know, just look it up and do that but arguing and saying, No, no, no, this is not you know, effective and let’s try it my way. Unfortunately, in this profession, doesn’t usually work. You have to find someone famous or find something authoritative and you’re almost daring them to say that I know more than John Roberts or Elena Kagan, more than I know more than, you know, the Chicago Manual of Style. And as I’m sure you’ll agree, there are plenty of lawyers who are that arrogant? They do, but most actually don’t. And they really do want to know they are willing to bend.
Jeremy Richter: Yeah. And, you know, I had a partner that I worked with who, we just had very different writing styles and word choices, but I worked on a lot of briefs with him. A lot of, you know, just a lot of writing. And when I was the associate, and he was the partner, it ultimately came down to, I am being paid to write the way that he wants it and as long as it’s not terrible, then if it’s just stylistic differences, then I had to make the concessions and just write the way he wanted right in on my own time. I can make the word choices I want to make
Ross Guberman: And you know, after a while, that can be a little demoralizing. But on the other hand, there’s probably a reason to bosses, the boss in the sense that people generally succeed because they’ve found some way that may not be my way or your way to define some way of adding value to their clients. And sometimes people get so caught up in these writing battles. They don’t take advantage of the opportunity to realize that maybe the boss can teach you something about strategy right or, or teach you something about which points to emphasize even if you’re gonna butt heads on the wording.
Jeremy Richter: All right, so as we get ready to wrap this up here in the next couple of minutes, what advice would you have for lawyers or you know, non-lawyer business professionals who want to chase ambitious dreams like you did in creating this career that you have built from the ground up? So whether it’s just launching into a side hustle or even transitioning out of the practice of law into something else, what’s some advice you would give to people who are considering that?
Ross Guberman: So I’ll just give you give you a couple things. So one is, I think for most people, unless they’re really, really lucky, and willing to take huge risks, it doesn’t really work to go from whatever job you’re leaving behind to being an entrepreneur. So it’s really important to have some sort of income stream, even if it’s, you know, much less than you’re making before so that you’re not constantly feeling pressure that if everything doesn’t go great, you’re gonna you know, not be able to pay your bills. So that’s one thing is as exciting as it can be to just go cold turkey on your old job. You want to try to find some way to preserve a reliable source of income, preferably something that’s not going to Take a huge amount of time. So that’s the first and then the second is you don’t want to, you obviously don’t want to be unrealistic or expect yourself to have a really successful business right off the bat. But I do think it’s a good idea to be honest and set some sort of goalpost or milestone. So for example, if, you know if I had been trying to do workshops for a year, and I six months in I had three firms and 12 months, and I only had five, I would have, I would have given up and I think that would have been appropriate not because there’s no chance that I would have ever succeeded. But because at that point, sometimes you have to cut your losses. So I think it’s good to have some sort of reasonable benchmark, so that you know, yourself that you’re not going to be in a situation where years go by and you’re gonna have regrets.
Jeremy Richter: All right, so I like what you said there on both of those things. I believe strongly that taking not taking that leap. But instead building a bridge is absolutely the way to make the transition. But you also mentioned goals there. And I’m a huge believer in goal setting. I’ve been doing written goals since 2016. And it has made more difference for me in my law practice in my writing practice than anything else I’ve done of having written goals that are specific and ambitious, but also achievable. Is that something that you practice?
Ross Guberman: Well, no, I mean, I can come not as organized as you are, it sounds like and that partly comes from having changed careers so many times, but I do probably have at this point, a pretty good sixth sense for whether something is going to fly or not. And although it that’s not necessarily linked to Formal goals the way I was suggesting people should, you know, approach this. It’s sort of the same effect. So there is a point. And there have been points where I, where I have given up on something that I’ve been trying to do and gladly sell with no regrets, because I just realized it wasn’t. It just wasn’t working.
Jeremy Richter: Yeah, and I think that’s an important part of being entrepreneurial, too, is knowing when to quit something.
Ross Guberman: Yes. And that’s hard, right? Especially if it’s something that you believed in, but you have to remember that pursuing something that’s very unlikely to give you a return is taking time and energy away from endeavors that could be much more satisfying and successful.
Jeremy Richter: All right, we are out of time. If people want to follow you, where’s the best place to do that?
Ross Guberman: Well, there’s Twitter, so @LegalWritingPro, also legalwritingpro.com, and then briefcatch.com is where you can find anything you’d like to know about the tool we discussed, Brief Catch.
Jeremy Richter: Thank you so much for coming on Lawyerpreneur. I think it was really informative but I really enjoyed the time.
Ross Guberman: I did as well. I always like talking to you, Jeremy, and good luck with everything, and hope to talk to you soon.
Jeremy Richter: If you enjoyed the show, you can support it by writing it on Apple podcasts or wherever it is you’re listening. And make sure to subscribe so that you don’t miss anything. You can also support the show on Patreon at patreon.com/lawyerpreneur. Thanks for listening.