The Sterling Family Law Show

Solo to 10 Staff: 20 Years of Growing a Law Firm - #194

• Jeff Sterling Hughes

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In honor of Jessa Nicholson Goetz’s memory, we’re sharing her story about growing a law firm from solo to a team of 10. Here's what 20 years of building taught her about making that first scary hire.


Jessa started at 23 in a basement office, waitressing on weekends just to keep the lights on. Her firm now has 6-attorney with about 10 total staff. This is the real, unglamorous story of law firm growth—working three jobs, sitting by the phone hoping it rings, making that terrifying first hire, and slowly figuring out how to be a boss when nobody taught you how.


Learn when to make your first hire, how to lead a team without losing yourself, and why staying in your lane beats chasing every case in this episode.


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📝 Get your FREE Law Firm Growth Guide: https://jsterlinghughes.com/


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📄 CHAPTERS


0:00 - A Note About Jessa 

0:16 - Growing a Law Firm: Meet the Attorney Who Started at 23 

3:26 - The "Arrogance of Youth" That Made Her Take the Leap 

4:37 - Working 3 Jobs While Building a Legal Practice 

6:18 - "I Didn't Know Which Table Was Defense" 

7:00 - When Solo Practice Finally Became Sustainable 

8:47 - The Bambi Phase: Your First 2-3 Years Will Be Wobbly 

12:42 - Your First Hire: The Most Stressful Decision You'll Make 

14:02 - "You Come Last": Taking Responsibility for Your Team

17:21 - Law Firm Leadership: Why Owning Mistakes Wins Respect 

18:40 - Advice for Young Attorneys Starting Their Own Firm 

18:58 - Advice #1: Self-Employment Isn't Half-Employment 

19:56 - The Courthouse Staff Hack That Gets Transcripts Faster 

21:19 - Why Staying in Your Lane Beats Chasing Every Dollar


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Jessa is a trial attorney out of Madison, Wisconsin, who started her firm from scratch, has grown into multiple attorneys, and still loves the practice of being in the courtroom and working with individuals to help them through their case. This is a great episode, and I hope you enjoy it. Welcome back to the Sterling Family Law Show, the podcast designed to help law firm owners build the practice of their dreams. My name is Tyler Dolph. I am the host and also the CEO of our law firm focused marketing agency called Rocket Clicks that was born out of the law firm that we own and operate called Sterling Lawyers, that has grown to over 27 attorneys. Today, we continue our owner operator series, and we interview Jessa, who is a trial attorney in Madison who has built her firm from zero to now over five attorneys. And she still has a passion for being in the courtroom. I love to talk to her and and hear how she built her firm, and how she went from being a solo entrepreneur to to building leadership skills and building a team of attorneys. Just a thank you so much for being with us today. I am so excited to learn from you and hear your story. Would you mind introducing yourself to our listeners and giving us a little history on how you came to be with us today? Sure. Well, thanks for having me. My name is Jessa Nicholson Goetz I'm a criminal defense attorney. I practice all over the state of Wisconsin, but my office is located in Madison. I started my own practice, so I'm private bar, started right out of law school, and now I'm one of six lawyers at the office with some additional support staff. So there are about ten of us. Awesome. Congratulations on your success. Going back to the beginning, how did you start your firm? Why did you do it? What were we doing before? Sure. So I was someone who did everything fast. I graduated from college in three years and went straight into law school, and during law school I fell in love with criminal law, was very sure that that was where I wanted to be. I actually interviewed with, Legal Aid down in New Orleans, but Hurricane Katrina hit, during that process. And so jobs there were not going to happen. And so I ended up deciding to hang out in Wisconsin for a little bit while I continued to apply sort of nationwide to public defender offices, because I figured that would be a good way to get trial experience here. We can kind of take these overflow cases. The public defender's office assigns some cases out to private bar, so I sort of hung a shingle and started taking some of those cases and then realized I had number one loved you know, I loved living in Madison. I had for law school. And number two, that I really liked practicing law here. And so I ended up staying. And I've had a sort of variety of office spaces in different areas and expanded over time. But it's been one version of me, you know, running my own thing for almost 20 years now. So. Wow. That's incredible. What, what was it like, kind of that first year thinking. Okay, I'm going to go and do this and take all the risk and be an entrepreneur. Or are you scared? Did you have prior history in business that allowed you to ramp up, or how'd that go? You know, so it's funny, I like I said, I was really young, I was 23. And I think you have to be like young in 23 to decide to do something like start a law firm. I look at it now, I'm 42 now and I'm like, wow, that was a really brave young woman. But at the time it didn't feel like it. I'm a third generation business owner. So I grew up in a very entrepreneurial family, and that was probably a big part of it is when I had kind of floated the idea to my father, he's like, well, yeah, why wouldn't you do that? You know, and it never the sounds kind of bad, but like, it never really occurred to me that I was going to fail. And, and I didn't. So that worked out. But I think it was just the absolute arrogance of youth. That and the energy. But so, you know, I mean, at first I worked three jobs. I mean, I waited tables, I worked a double shift every Saturday, and Sunday and then worked at my little office in a basement out in Fitchburg, during the week. And then I wrote copy for a local political organization sort of ten hours a week to fill my time and just to sort of supplement income and slowly started to drop the jobs. Over the first year, I absolutely remember feeling totally at sea because, you know, I, I don't have parents that are lawyers. I didn't know any lawyers here in town other than, you know, the people who were my professors. It's not like I had some built in sort of legal community. I had to go meet those people on my own. And so it was a lot of trial and error. It was a lot of telling myself that sooner or later I was going to know the answers. And a lot of rereading The Rules of Evidence over and over again to try and know them sooner rather than later. A lot of just, I got to figure it out, and I'll do whatever it Pretty much. Yeah. You know, so it was. Yeah, it was a lot of fun. Like, now I look at it and I'm like, oh God, that was great. And no, it wasn't. But you know, in hindsight makes it rosy. I guess. I think that's a really actually interesting perspective is that as you look back on those early days, you know, in the moment you're like, how the hell am I doing this and working all these hours? But you look back like, hey, it was worth it. I actually, you know, had some fun. I was learning all these new things and that's really important. I think it is too. And I think that there's something, you know, I mean, I'm immensely proud of it just because I can look back and say, yeah, I really did that, you know? I mean, those were long hours and long weeks. And there's a lot of humbling that happens when, you know, I mean, you're a law student. Everybody tells you how brilliant you are your entire life. Right. Like, so you're in law school and you're like, oh, I know everything. And then you walk into court and you're like, I don't even know what table is that? I, I don't know which ones the prosecution don't know which ones the defense going to have to ask the bailiff. Hopefully he'll tell me, which he did. And yeah, it was, you know, and so that it kind of brings you back down and, and I think that that's probably healthy, particularly for ambitious 23 year olds. And, you know, now I have a lot of fondness for that. figure it out along the way. Speaking of figuring it out. So you you do this, you take the dive. You're working all these hours, you're working multiple jobs. At what point did you start to gain momentum? Did you start to think, okay, I'm figuring things out. I'm growing a little bit. I don't have to work, you know, both Saturday and Sunday at a different job or at what time period was I like? How long did it take you to get there? I think I quit my waitressing job within the first six months. So I think I, I was able to ditch that fairly quickly, probably did the copywriting for another six months. So probably because I started in June, I was sworn in in June and started right away. So probably after that first full year I was able to make practicing law my only job. And I would say, you know, I mean, I'm a trial lawyer. It's my belief that you kind of need to have at least ten trials before you really feel comfortable, where objections start to just flow naturally. You don't have to have sort of cheat sheets and notes, and I tried really hard to get as many trials as possible as quickly as possible. So I would like I said, you can take public defender overflow cases. I would bother the appointment clerk and say like give me something that somebody wants a trial. I don't even care if I'm lawyer number five on it, just if it's going to be a trial, give it to me. I know the only way that I'm going to learn to do this job is by doing this job. Like that becomes apparent very quickly. Once you spend your days in court instead of class. Right? Is like experience is the number one way to learn. And so I just did everything I could to get that as quickly as possible. And so I think I had probably had, you know, ten trials definitely by the time I was three years out, definitely by the time I was three years out. So I would say probably, yeah, those first 2 or 3 years, you're kind of feeling like Bambi, you know, your legs are wobbling a little bit everywhere you go. But then I started to settle into it. The, the skill required and the confidence required to be a trial attorney is something different than I think a lot of attorneys have. Right. Like, we have 27 attorneys on our staff at our family firm, and only a handful of them have been in more than 2 or 3 trials in their entire career. Right. So it's I am always fascinated by the trial attorney because I think it's a different breed. So and, you know, there are different types of trial attorneys, right. And I definitely come from so I was a creative writer far before I was ever a lawyer. I paid for a lot of my undergrad with poetry scholarships. And my only real public speaking experience was when I would go do slam poetry at really pretentious coffee shops and undergrad. But that serves you a little bit. Well, because I try. So now I, I try really pretty exclusively violent felony cases. So about 80% of my caseload is sexual assault offense, sensitive crimes defense. I do some child abuse. I do homicides. If I want to have fun, I'll take a bar fight, because those are fun cases to try. Put a little less pressure than what I'm used to, but those are really cases about conflict and about trauma. And, it's the story, right? A lot of times it's not. You know, I don't do sort of the scientific. I'm not cross-examining about the validity of a field sobriety test. I'm talking about human emotion and credibility and memory and the way that we see things and the way that we evaluate their morality, but also legality and how that interplays with, you know, the things that my jurors believe about themselves, you know, are they patriots? Do they like where they live? Do they want to protect the presumption of innocence and gelling those sort of concepts, you know, these high brow like Sixth Amendment versus these are really crying, you know, like some damaged, tragic circumstances that we're going to hear about and how do these things go together. So for me, I really think of trial, as one of the last places that we have oral tradition. Right? It's one of the last places that we tell stories orally. And then we create a written record. But it's really you don't see that in almost any other arena. So it's a really special place to me from a. a great perspective. You know, it's a, it's your passion in it. yeah, it's a very creative space people. I don't know that law school tells you to really amp up your creativity. That was not my experience. They weren't like, oh, look, you're artsy. That's great. But now that I do it, and now that I get to teach about it, that's always the focus I have is how do you tell this person's story? You know, I defend human beings. And so really, I, I work with people. Can you confidently answer this question in three seconds? Do you know if your firm is winning or losing? If you can't, that's something we need to fix urgently. We are hosting a free webinar that shows you the eight numbers that answer that question. You'll learn where you're leaking revenue, what to do to fix it, and how to embed this into your daily operations. It's called how to Moneyball your law Firm. Get bonus templates, checklists, and worksheets. If you show up live, link in the show notes to register. I want to, bring us back to the business side of running a law firm. And, you know, the fact that you were a solo kind of entrepreneur to start your journey, and it was just you, talk to us about the journey of becoming a leader, of adding team members and being able to delegate and having to to grow and change right as a person. Because you can't do everything as your firm grows. Well, and I'm, I'm laughing a little because I will tell you, in terms of adapting and leadership, when I went on maternity leave and I had my daughter four years ago, that was the time that the rest of my office chose to implement case management software because they were like, we're just going to do it well, justice gone. We're going to put instructions on her desk. When she comes back, she's just going to have to deal with it because we know she's going to fight us on it. So, you know, I never did I didn't have some vision of, like, I want to have this law firm with X amount of lawyers that does, you know, services this part of the state. It wasn't that deliberate. It you know, we grew out of the necessity like out of the demand where so, you know, the first person I hired was a legal assistant. That was probably the most stressful hire I've ever made. Just because it's like, okay, number one, can I afford it? Right? Like, you run all the numbers and you know what you have coming in the door, but you're starting to to take on this responsibility for someone else. And my family, like I said, third generation business owner, I had always been taught that like, you come last, if you're going to ask someone to sign up for your to do labor for you, you make sure that they are taken care of and that means providing them health insurance. That means making sure that they have a living wage. That means making sure that they can afford to pay for their gas to get to and from work, you know what I mean? And so that was I remember that pressure. And I was young. I mean, I was in my late 20s, and I probably stumbled with not knowing how to set like the best boss versus friend boundaries. You know, as I think probably most young people who are trying to lead do, we still have a really familial, really friendly office, you know, I mean, we we all sit around and talk, we staff cases, everybody gets along really well. And so I that's important to me because, look, you spend all your time with like the people you work with, it's good to get along with them. But I just part of I think learning to be a leader also came with developing how you talk to clients, too. You know, you realize that they're looking to you for reassurance and to to make them feel calmer and to make them feel protected in a system where they're vulnerable. That's really what my staff and my associates want from me, too, right? I mean, my business partner now was an associate of mine, and he made partner and as at first I trained him. And now obviously, like, you know, I mean, we're peers, but there was a period of time where he would come in and ask me a question, and it was clear that you just wanted someone to tell him he was thinking about things. Right. You know, it didn't really matter what my answer was, so long as it was like, you're doing all right. But and so learning to sort of provide that support but also provide constructive feedback, when something didn't sound like it was going so well, I think it's always a balance. But you it's a skill like any other skill. And lawyering sort of creates this loop, right? You have to negotiate a lot. And so you learn how to interact with people and what sort of motivates people to do things that you want to see them do you. And what doesn't. And then you can take that back and apply it to the way that you engage with your office and vice versa. So it's there's a lot of feedback loops that overlap that help you, I think, end up where I want it to be. Right. And I think if you ask my, my employees, they tell you that I'm a pretty decent boss. I think it's a skill, like anything else. Right? You. When you were starting your trial career, you're like, I want to get as many trials under my belt as possible because I want to feel like I can stand on my own, two legs. Like the Bambi example. To me, leadership's the same way, right? You have to be able to do the reps and work with people and understand yourself and how they're working and all the things. So it's, it's great that you're you're continuing on that journey as well. Well, and I would say, like both, I think success in a courtroom and success in your office also to me, personal responsibility is a big thing there, right? Like, I find that a lot can be smoothed over by even saying, you know what, I came in hot there. I was worked up. I was getting out of a bad hearing, and I probably was. I was probably aggressive with you, and I'm sorry. And I shouldn't have done that. I think just being able to own when you don't do things perfectly develops a fair amount of respect from your colleagues, because especially these days, it's so rare that anybody can just say, hey, I made a mistake. Big time. It's so rare. And having the humility, especially as the leader, as the founder, sets the tone, I think, for the entire organization. mean, I remember my dad would always say, well, if there were a hundred ways I could have done that, any of the other 99 would have been the better option. That was always his like way of working into an apology. And I think I steal that a lot. Well, gosh, that was probably the dumbest possible way I could have approached that. So let's just hit reset and try again. I mean, sometimes that's all you can do. I don't I love it. So so it says, we think about the, community, the the young attorney who's thinking about starting their own firm and wants to get the reps in and be a successful law firm owner one day. Do you have a few pieces of advice or learnings that you could share, with them? Yes. I have some very firm pieces. Advice number one, if you think that you're going to start this office because you get to, like, make your own schedule and you're going to have a successful full caseload, like, disabuse yourself of that notion. You have to go to work. I would sit in my basement office that was repulsive. And in that windowless office, I would reread the rules of evidence over and over and over again when I didn't have a full caseload because I was hoping the phone would ring. Because the phone rings, you don't answer, they're going to move on to the next. And I was still advertising, like in the phone book at this point. Right? This is before internet advertising really was the primary way that people found you. They're just going to call the next number. So you have to be there and you have to be committed to being at work. And I think people sometimes view self-employment as half employment. And if that's what you want, great. That was not what I wanted. I wanted to be fully employed. Right. You know, so you have to treat it like it's the job that you want it to be, whether you have the caseload to support it or not. Number two, you are not smarter than or more important than clerks, bailiffs or any other member of the courthouse staff, and they have more power over you than you think. If you ever want to take a vacation, be nice to the clerk. I can't even tell you how many times court reporters will get me a transcript, because I treat them like human beings, that they will not give opposing counsel because opposing counsel does not do the same. So don't think you're better than people. You're going to need help. You're going to need help getting a case reset. You're going to need help flagging down a duty judge to get a warrant quashed. You're going to need people who are support staff help. And so often I see lawyers act like they're better than the other people in the courtroom. Make friends. These are people that are going to be in your community for the next 40 years. Get to know them. They're all nice. They're all interesting. They're lovely people, and they've seen more in a courtroom than anybody else. And they'll tell you, well, no, juries don't like him. I mean, you can learn a lot from talking to the courthouse staff. So that's probably my number one piece of advice is be nice to the people in the courtroom. Yeah. Like, just don't be a dick. that's a very legalistic way of saying it, but, like, just be normal. Just be normal and kind and treat people like they're normal and kind, and that goes well. Number three, I think I'm out. Number three, it's really not a good idea to think you can do every type of law. Very early in my career, I would get phone calls where it was like, well, can you draft this contract? Well, no, I can't, because I don't know anything about that. And I pretty much slept through contracts because it was an 830 class on Fridays and bar review was Thursdays. So no, I, I even though I'm not making very much money right now and it'd be great to, to be able to take this on respect to your own skill set and your own work product, enough to know what you are capable of and what you aren't, because it's going to cause so much more stress to try and tackle something that you don't have the training and experience to do, and then inevitably fix whatever mistakes you make than it is to sort of stay in your lane and be patient and wait for, you know, that case load to build up in the area that you are comfortable in. And I think that, you know, stretching yourself over too many practice areas or too thin is something I see a lot of people who hang shingles do that I think is ultimately to their detriment. Hard to learn a new practice area every time a case comes Oh well, now you like again. Why don't you do it for a while? I'm like, why would I want to? Why would I ever volunteer to learn something new? I'm such an old dog. I don't want new tricks. you're great. At what? You know, what you've been working on for the last year. You know, so that I think that's another one is it can be really tempting to say. Well, yeah, I'll try that. Especially when you don't have other things going on. Right. But you're going to be better off long term if you stay sort of in your area. it. So? So I'm so appreciative of your time, of your insights. I loved your passion. And I know our audience will, too. Again, appreciate your time and look forward to having you, back here on the podcast. Absolutely. Well, thanks again for having me. And happy. Well we're recording this on July 3rd, so happy fourth. I don't know when it goes up or belated fourth or it wouldn't be belated fourth. Whatever. Yeah. You know what I'm saying. Happy summer listeners. Happy summer. Thank you very much.

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Jeff Hughes

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