Craig Robertson and Matt Easterling were guests on the Made in Mississippi Podcast.  In this episode they have a lengthy discussion with the host, Casey Combest, about how they each got their start in family law, and some of the more practical aspects of running one of Mississippi’s most successful boutique law firms.

Show Notes

This podcast was recorded at the office of Robertson + Easterling on February 27, 2020 by Blue Sky Media.  The Made In Mississippi podcast interviews successful Mississippians to gain valuable insights into their approach to business, life as a busy entrepreneur and what they’ve learned throughout the course of their career. This is a dynamic resource to educate and encourage other Mississippians who may be feeling the negative connotations to launching, growing, or keeping their business in our state.


Casey: Hello everyone, and welcome to the Mad in Mississippi Podcast where we talk about entrepreneurship in our state. I am here with some killer entrepreneurs, Craig and Matt, introduce yourselves and tell us a little bit about what you do.

Craig: Hey guys, this is Craig Robertson. I am a family law attorney been practicing for 20 years in the Jackson Metro are.

Matt: I am Matt Easterling and I am also a family law attorney and together Craig and I own Robertson and Easterling PLLC, which is a boutique family law firm who serves people all over the state of MS.

Casey: That’s great. Tell us a little bit about y’all’s journey. How did y’all get where you are today?

Craig: So, I am from South Jackson, spent a lot of time at level wood playing baseball and actually went to college on a baseball scholarship to Mississippi College. Had a great season, transferred to Mississippi State and walked on the baseball team and after baseball was over, was inspired by a class I was taking to go to law school so I was fortunate enough to get accepted to Ole Miss and spent three years of law school there. When I got out of law school, in 1999, I got a job at a little firm in Brandon, MS and 6-7 months into that job I was miserable. I have written about maybe 3 poems in my lifetime and one of the poems that I wrote was how miserable I was at that job, staring out my window. If I could find it, that’s how miserable I was. Art from pain. The guys pretty much hated me, and I was a crappy lawyer and they pulled me into their office on a Monday and they fired me. For a 25-year-old, who had always been successful at everything, its was like a quarter life crisis. So, I got fired from my job on a Monday and then on Tuesday I made a call to a legal staffing representative and had a meeting with her. Told her about my life and told her that my dad was an electrician, my mom worked in the mall and I didn’t even know a lawyer. I had never even met a lawyer. I told her I wanted to be self employed and she looked at me and said “Craig, doesn’t look like you need a job, looks like you need a place to work. Let me introduce you to this guy who lets other lawyers rent space from him. His name is LC James”, so I called LC and he was gracious enough to meet with me. His office was a big office downtown. I love LC and I am in relations with him still to this day, but he is a mess. He has crap all over his office. So, I am sitting in him office and kind of downplayed how much family law he did and he just told me about his practice. After telling me his story he says he would start me out at $30 an hour. I did the math in my head and was like I just got a raise. He offered me a job and moved me into a tiny office with no window. I moved in a homemade dining room table and had a little compact stereo computer that cost me about 4500$ in student loans that wouldn’t even run my computer today and I went to work and started my little law firm, and he handed me my first case. So that is how I learned how to practice law.

Matt: So that was 1999 and as you were getting fired, I was enjoying my junior year of high school. I am originally from Vicksburg, Ms. Grew up there, loved it, graduated high school, went to the University of Alabama and had a lot of fun there. More fun than I probably should have, studied business finance. Once I got out of college I went to work for a wealth management firm and enjoyed that type of work but the place I was, focused mainly on clients with a net worth of maybe 5-20 million dollars and as a 20 year old idiot, I knew they were never going to let me manage their money. So, I thought maybe I will just go to law school and I will sound way more attractive when I get out. Hated law school, I went to Ole Miss, I didn’t like the classes, I just couldn’t stand it. I really wanted to just quit. I couldn’t image myself doing this. My father who was a physician here in MS and he said, “practicing Medicine is nothing like medical school”. He encouraged me to try and do a clerkship one summer, but I knew I was not going to practice law. I hated it, but I decided to appease him, and I was lucky enough to do a clerkship the summer of my second year of law school and that is when I met Craig. When I was offered the internship, they asked me if I had any particular part of law I was interested in and in my head, I was thinking, “I don’t want to do any of it”. I thought about the one class that I had taken in two years of law school that I actually didn’t hate and that was family law. I told them I might be interested in that and that is how I met Craig.

Craig: So fast forward, to when I had met LC, he gave me the ability to foster and develop my own practice while working on his files. I really served as a contract attorney for his firm and he would give me cases to work and I would work those pretty independently mostly. He gave me the ability to go out and get the work.

Casey: So, kind of gave you those entrepreneur moments?

Craig: Absolutely. He was paying me 30$ and hour but I could charge 100$ an hour if I found the case on my own. SO, I was very motivated to foster and develop my own practice. Back in the early days I had my own web presence before other lawyers did and from a marketing standpoint, if it was available, I would try it. I started a blog. I would do writing contest at Ole Miss. Turned those into video blogs and do video contests at Ole Miss. I took a risk and there was a really high Attorney in Meridian who was running for Chancery Court Bench and most of the work we do is in Chancery court in MS. So, I told him that if you win Chancery Court Bench I want to figure out a way to take over your practice and he won the election and I took over his practice so I was doing the work for LC, I was growing my own business, and then I opened an office over in Meridian MS. This was before dropbox and a lot of easy communication tools so in order to get everything done, I had to hire people to work for me. First it was an assistant, then a paralegal, then associate, and another associate, so being a small business owner and the administrative component of it became a little bit overwhelming. So, a guy that I had played baseball with had joined a small firm out of a regional firm. They had an office in Little Rock, Oxford, Jackson, and I was operating out of Ridgeland, MS and also had an office in Meridian and they did not have a family law attorney there in the firm. Several people told me not to do it, but a few people told me it was a good idea. My numbers from a revenue standpoint were, I don’t want to say artificially inflated, but I had purchased this office over in Meridian and so I had gone from basically double the gross revenue of my operation in a really short period of time, so I became the youngest equity partner in this small regional firm. When I got in those environments, I found that it was not super conducive intimate private nature of family law. It was downtown, to get to our office you had to park I a parking garage and even a simple conflict check would cross the desk of 25 to 30 people. I started getting conflicted out of several cases but I did meet my now law partner, Matt Easterling, in that environment. The first time we spent together were maybe playing golf and one of the things I remember about Matt was, he was a terrible law student as he has already told you, and his entrepreneurial spirit. He told me about some business ideas him and his buddies have had and I appreciated his vision and so when my associate from New Orleans decided to move back with her husband, I offered the position to Matt and was like “hey dude send me your grades” and there was this silence on the phone. I was like that’s not a problem is it and he was like well… just want you to know that they are probably not great, and I was like I wasn’t that great either in law school. So I went to bat for Matt and convinced the other lawyers that he was the guy and we went to work together.

Casey: When was that?

Matt: That was 2008. Unlike what Craig mentioned earlier, the climate was completely different. The world economy was tanking at the time and Mississippi and lawyers. Before as long as you could graduate, you’d have a job well it was not like that when I was in school. I don’t know how many of my classmates had a job lined up leaving their third year of school. It wasn’t a lot. I know almost all of the ones that didn’t have one lined up, certainly deserved to have one before I did but I was fortunate enough to have this opportunity and so I made it through the end of law school, went and joined Craig in Jackson. There were two stipulations to me getting the job, number 1, I had to come to work immediately after graduation. I didn’t get to have a summer to study for the bar and number 2, it was contingent on me passing. If I didn’t pass, the job didn’t exist anymore. So basically, I want you to come work for me, but I am not going to let you study and I am not going to let you work here if you don’t pass and so

Craig: That doesn’t sound unreasonable.

Matt: Well, I guess you wanted to see how I would work under pressure and somehow, not sure how, I made that work and showed up on my first day of work after the bar exam. So what I consider to be my first official day at work and they gave me a parking pass and all the different trimmings that came with a midsize firm. Craig had a hearing somewhere else that day so he wasn’t around which wasn’t a big deal, and he sends me a text towards the end of the work day and say “Why don’t you come out to my house when you get done working?” so I drive over there and that is when Craig tells me he is leaving the firm.

Casey: On your first day?

Matt: On my first day, post bar exam.

Casey: How did that make you feel? What was going through your head?

Matt: Well, I thought it was some type of joke and was like this is not funny and quickly realized he was serious. That was an overwhelming moment because here I was with not the best grades, found my way into a job and now I didn’t know what to do. Was I going to stay at this larger firm or am I going to take a chance and leave?

Casey: So, at that point was Craig inviting you to be an associate?

Matt: He did. He invited me to come with him and start on this journey. I wasn’t an owner from day one, but I can say even then, it still felt like I was apart of it or helping create it. I obviously did not have the financially skin in the game, but I definitely felt like I was involved in the creation of the firm. Thankful that he included me in that. I called my parents on the way home and they thought I was just leaving the office for my first day and I was like “yeah I think I am going to resign”. They thought I was joking and when they realized I was serious, they went through every stage of the grief cycle just in matter of moments and trying to bargain me to stay but I just knew that this was one of those opportunities that doesn’t come around that often and if there was going to be a time for me to fall on my face, it is right now. So, I took the leap.

Craig: I like to say I took a chance on Matt and Matt took a chance on me and that is what happened. He was involved in every step of the way because he, along with two or three other employees, did resign that day. I had what I like to call my Jerry McGuire moment. It had already been resolved in my mind that long term, it wasn’t going to work. I just didn’t think it was right for my clients and I didn’t think that was going to be the way I could best serve them in that environment and so when I made that decision, I put my check book in my back pocket and folded down my lap top and picked up my goldfish and walked out.

Matt: I am the goldfish in that scenario.

Casey: Lets stop here for just a second, someone listening right now is wondering where you guys work, and they are looking at challenges and opportunities. What advice would you give them?

Craig: My advice would be to leap, and the net will appear. I don’t know if that works for every personality type, but I am one of these guys that is fire and ready and that served me well all through out my life but sometimes I just operate through my gut. Every time I had taken a big chance in my life, it didn’t always workout the way I had planned it but it has always worked out. My dad was one of the hardest working men I have every known. Unfortunately, I lost him 7 years ago, he would have been 90 in January, he was an electrician. His hobbies were other people’s work. He would build things, he had a garden, cows, tractor. My mother modeled hard work. When I mentor younger attorneys, I tell them to hustle. That is really what it comes down to, show up and hustle.

Casey: Matt, any advice for someone about to make the leap?

Matt: Well, do it. That is the hardest part. I think unfortunately a lot of people spend most of their lives paralyzed by fear, uncertainty, and often times people try to rationalize themselves or plan accordingly or wait because now is not the right time or I need to get my kid through kindergarten or x happens or y happens, and while I a not advocating being reckless, I think people wake up and realize, its 10 years late and the windows are closed. If you spend all your time waiting for the perfect circumstance, life is going to pass you by. Sometimes you just have to go and figure it out.

Craig: Matt was in that situation when we did make the leap to leave the firm, that there wasn’t much to lose. Certainly he had a job, and turns out that firm basically fell apart within a few years after that, retrospectively it was the right move but I had a lawyer friend who let us set up shop in a conference room and all of our clients cam with us. Matt was with me as we set up our first bank account and looking for office space, we found a lawyer who had a few empty office spaces and moved in and started doing business. I haven’t regretted it one day since.

Casey: We want to transition to the more strategic things and what you have done with your marketing and what has led you to where you are today.

Craig: Yeah so, like I said all of our clients came with us. We went through a divorce with a firm then it was time to get to work. I have always been very interested in business development and entrepreneurship and that was one of the things, not just his loyalty, but his mind for business, finances and Matt can do arithmetic in his head faster than any person I know so I appreciated his mind for business and I knew he was going to hustle. I knew Randy Easterling, his father, had modeled that for him and my father, Guy Robertson, had modeled that for me. Matt almost is exactly 10 years younger than me and so I knew a lot about practicing family law and Matt had been exposed to a lot of business ideas and concepts and one of the first things we did was creating a new website and we tried to do it differently and creatively for it to look more like an artist website than an attorney website. We wanted it to be content driven, so we created lots of content, blog articles, videos, rich content about family law in MS. We put our nose down and went to work. We really haven’t looked back since then. We rebranded the firm to Robertson and Associates and then back in 2017 I asked Matt to marry me.

Casey: You did not literally ask him, though right?

Craig: I mean yeah man, other than my wife, Rachel, it is Matt. I invited him to be an owner in the business and then rebranded it again to Robertson and Easterling. We have a couple of associates and a great client care coordinator and paralegal, Cassie, who is one of a kind. They literally broke the mold when they made her, and she is street smart and learned the practice of family law and has more empathy in my little finger than I have in my whole body. It takes that to do this job, we do really hard work. We sit with really good people in the most difficult seasons of their life.

Matt: From a business owners’ perspective, I always felt like Craig and I were in a very difficult market. I knew that he did this work very well and I knew I could do it well if I put my mind to it but there is an old saying, “How do you make a lot of money as a lawyer?” and the answer is get grey hair. For the longest time, one of the biggest predictors of success was you just had to put in all the time and just have the appearance that you are older, and experience equals success. That is a very frustrating thing for a young person because that is not in your control. I can’t do anything about how old I am. I think for any business person, we tried to think of ways that we could set ourselves apart. What are things that I can control that I can offer my clients that other people may not have? That is when we started looking into the different digital forums and blog articles and different ways to market our business. I truly feel like in our space, in the state of MS, we have been unique to that. It was all coming at the right time when there was a tipping point generationally where people Craig and I age, were starting to come of age in their own careers so they were much more digitally minded and look at things on the internet. Before, if something was happening in your marriage you would go talk to someone and sit down with a lawyer. That still happens to this day, but you get that name and the first thing they are going to do is look you up, and so we were sort of on the front end of having that online presence.

Craig: Yeah, I don’t think there is any question that we were digital pioneers. My mentor was LC James. To this day, I don’t think LC has a computer on his desk but that was beyond heard of for a generation Xer like myself and I was able to borrow from LC’s reputation. The time that I met LC, he was in his late 50s and was really in the prime time of his career and he had been working at a super high level at his time. So I was able to borrow form his reputation and if I was working with him, I must be talented and it just so happened that my personality was very well suited to be a family law attorney and I think that is what I would tell a young lawyer/ entrepreneur. I would tell him that you’ve got to get with someone who is doing great work. You have got to see it and be it. Also, subscribe to the idea that you can get really good at something you put 10,000 hours into. That takes about 5 years and so you can do that on day one. You have to show up, hustle, and do the work.

Casey: One of the things I have noticed over the years is how certain businesses fit certain personalities very well. How is this a good fit for your personalities?

Craig: I am an Enneagram 8. An enneagram 8 is a challenger and to a large degree, we are vulnerability challenged. We don’t internalize a lot of emotional energy. Just so happens that that is a great skill set in being a divorce attorney. Also, in a healthy place, I go to an Enneagram 2 which is a helper. I want to reach out and care for the oppressed and seek justice. That’s me. In law school I was a good communicator. Your family law attorney needs to be a great communicator and I had an idea for business. I loved business. The people that we represent are professionals and business owners and that skill set fit me well for this line of work. Lastly, I was very interested in psychology and how it works and out of all the different practice areas for attorneys, family law attorneys are truly the counselors.

Matt: For me, as far as my personality or skill set, first of all I think that in any business, any personality can find a way to work. Certainly, there are other fits that work better than others. For example, there are some very high-level successful family law attorneys that really don’t have much of a conflict-oriented personality. They are able to do things in a very diplomatic way, never heard them raise their voice or say anything ugly and then I know people who are the exact opposite. They both can figure out a way to make that work. I think its figuring out how to tailor your skill set to your particular business and how to help it thrive. Me personally, I enjoy helping people. I am a very compassionate person. I get very offended when I feel like I see people getting taken advantage of or somebody that is being mistreated. I like to tell people I enjoy bullying bullies. I guess at times I can be conflict oriented. I am sure my wife can tell you that I am and anybody that has had to deal with me on any type of intimate level. I also have the personality that I question everything. Its not because I don’t trust you, its just my nature, I am going to want to ask you more questions and get as much information as I can.

Casey: If you guys are in front of, I think I stole this question form you Craig, in front of a room with business owners, they are just starting out on their first few years of entrepreneurship, what is the piece of advice that you are going to give them to grow their business?

Craig: I think the advice that I would give to that room, would be something I have already said which is hustle. The other thing I would advise them to do is really think in terms of how they are going to differentiate themselves from other businesses. As a family law attorney, the way we do that is taking a more holistic approach to the individual that we sit with. Not every person or story is alike, and we try to take a person where they are, and understand their goals, and try to customize our service to best accommodate them. Specialization was a big part of my early career. We gained specialization and notoriety in the field that we worked in. We took extra classes, and workshops to set ourselves apart. We are laser focused. We don’t try to be everything to everybody. We are divorce and family law specialist. We have a boutique family law firm that is small, but it is exactly what our clients need. We represent people who have net worth up to 80 million dollars and we also represent people who are living paycheck to paycheck so we are set up to help a lot of different people in a lot of different walks in life.

Matt: Obviously any advice would be that you have to work hard but I do think it is important that as you are working hard, you have to make sure you are understanding the work you are doing you are attempting to do. If you just put your head down you are not paying attention to anything, you are not really seeing the field. If you are not evaluating what your business is doing, then you are probably not going to be working very efficiently. The other thing I would say as things start to grow, you have got to, as a business owner, you can’t over value yourself. You have to take care of your employees and treat them right. Figure out what motivates them. I run into a lot of people that just mistreat their employees and then they wonder why their business is never growing. It is just like a revolving door and people are coming in and it is just not going anywhere.

Craig: Our story as we have talked about, Matt was committed. The business had to go or he didn’t have a job and I involved him. He came and we opened the first bank account together, our credit together, we were sitting in our banker’s office together, we looked at our first office together and we just started from there. We found great tools available to us that help us keep track of our productivity. We stop and try to know ourselves. We did a podcast on intimacy and its about knowing and being known so you have to know your business and know how your business operates to know how to be successful. It’s not just about money but about time. We can’t not be family oriented and be a family law firm. We value the families of our staff and that is super important to us.

Casey: Yeah, as we close, what is something that has you excited about the state of Mississippi as it relates to business over the next 3 to 5 years?

Craig: I can speak to our business, a lot of the guys who have done great high-end family law work are getting older and so that creates opportunities for us. We have done some new things recently that you guys are a part of. We started podcasts and Matt and I are really enjoying that. It gives us an opportunity to have meaningful conversations with people who have lots to offer and we have found that it works on multiple levels. It creates content and content is what drives interest and it also creates relationships. When you sit there and have a conversation with someone for 30 or 40 minutes, you are building that referral source and relationship.

Matt: I am a big believer that just about everything is dependent on your perspective and how you look at it. I love MS and sometimes MS can be frustrating. Facts are, everything is a little bit slower here. Everything happens at a little slower pace. I always joke that if something else happens somewhere else in the world or country, we can expect it to trickle here in about 3 or 4 years. Sometimes that is frustrating but as a business owner, you can use that as an opportunity. If you are paying attention, you are getting a huge head start. You just have to figure out how to time everything right.

Craig: We are a very helpful and generous community of people in MS, and this is for another podcast another time, but my wife and I created a nonprofit, which was really a sister organization for the law firm called, 200 Million Flowers. The nonprofit world is very different from the fore profit world and I learned those lessons along the way, but what I do know is htta we Mississippians take care of each other. We love our neighbor and I think there is a bright future for us in the future.

Casey: Thank you so much for your time today and tell the listeners where they can find out more about your new podcast and your business.

Matt: Well our business, Robertson and Easterling, PLLC and you can find us online at and we also have a page on Facebook and Instagram.

Craig: And the podcast, everywhere you can listen to a podcast, we are there. There is also a special link on our website