Inside the Legal Arena: Trial Strategy, Transparency, and Transformation

Kyle McEntee:

We're joined today by Rob Alexander, a 2013 graduate of DePaul University College of Law. I interviewed you for the first time in episode 49 in an episode called Doc Review Hell. You were on a panel with two of your then colleagues on the Doc Review circuit, a cute way of describing short-term contract work that paid hourly, had no medical benefits, and left you all wanting more from your career. That said, it wasn't without value. You had flexibility. You made money when you needed it. Aand you had some great experience advocating for yourself. Now, five years after we recorded that interview, you started a law firm with one of your co-panelists and former host of I Am The Law, Kimber Russell. What I think is so cool is that you've actually done what you've set out to do. So here's a clip from the last episode.

Robert Anderson in 2018: It has definitely told me things that I don't want to practice because I want to do criminal and civil rights. I've only done one doc review that had anything to do with that.

Kyle McEntee:

And not only is this the kind of law you're practicing, but you're also running a firm. Something else that you said you'd do. So how does it feel? It's kind of wild to be transported back to five years ago, because our five year anniversary for our firm is in April.

Rob Anderson:

So, wow. It feels simultaneously amazing and sometimes it makes me want to pull my hair out. Like starting a firm is something that I didn't really think that I would do when I first went to law school. I thought I would be a public defender. So working for myself and getting to work along Kimber, it's an adventure, but it's really, really fun. It's really rewarding. It's exhausting. Because I mean, anytime you have to deal with like actual people as your clients, you know, emotions, and we're in very high stress areas of law. So people come to us with problems and when they're at their lowest and they're trying to get us to help them dig out of these holes or reconnect with their families. So while it's rewarding, there are days when I'm just like, why am I doing this?

But then I get up the next day and I do it again. So you just said it's been almost five years since you and Kimber started being our advocates. Tell us about the firm today. When we recorded the document review episode, I actually wasn't licensed yet. I had passed the bar, but I hadn't been sworn in. Now I've been a licensed attorney for five years. Our first case that we took was a traffic case. And we were terrified. We rented a car, we picked up our client, we drove out to Addison, Illinois for a traffic ticket. We were terrified. We were like shitting bricks. We had to go and talk to the state's attorney and the state's attorney would only speak to one of us. We did consultations together. We did client intake meetings together. We did literally everything together back then. Now.

I don't know who half of Kimber's clients are, she doesn't know who half of mine are. We go to court for each other, but we rarely go to court together anymore. We'll go to court for a trial. I mean, the fact that we've done trials, you know, is kind of wild. We won our first jury trial. I haven't lost a DUI trial yet. You know, we've had murder cases where we were prepared for trial and we ended up working out great deals for clients. We've gotten wild cases dismissed. To go from being terrified to even talk to a state's attorney to now making demands on state's attorneys, going up against attorneys who have 20, 30 years family law experience. It's wild. I sometimes think about this one time a client called and was telling me his problems. And I remember I literally said to this man, I said, “damn, sounds like you need an attorney.” And he said, “yeah, that's why I'm calling you.” And I was like, “no, no, no, I get it. I get it. I'm just saying this is kind of a wild case.” Like I cleaned it up, but I was like, man, this dude needs an attorney. Not thinking about myself as the attorney he called.

Kyle McEntee:

So how did you build this confidence then? I mean, going from scared and not really identifying as the lawyer in the room to now you do identify as the lawyer in the room and you're not as scared. What caused that transition?

Rob Anderson:

I have issues speaking about Robert, but there's something in me, and I see it in Kimber as well, where when we are speaking as the voice for someone else, we are like such staunch defenders of people that the nervousness just kind of goes deep inside, it's not on the surface, and we just plow ahead because we're speaking for someone, we're fighting for someone knowing that this fight, that the results of this fight, affects somebody's real life, gives me a kind of tunnel vision where I'm not focused on my own nervousness. I'm not focused on whether I know every single thing about the law in that moment. At that point, it's like do or die, put up or shut up. And I just go into this mode where I'm just, I'm in battle mode.

And before I go to court, I'm terrified still to this day. And I think that's important. And I think that's why we do such good work. We don't buy our own hype. Like we recognize that like, yeah, this other person has 20 years of experience. We started doing family law in 2020. We have to go and research. We have to read the case law. We have to read the statutes. I think that makes us knowledgeable in the cases that we need to.

But when you have the facts and the law on your side, it kind of feels like body armor. So you go into court and you're ready to take on anybody. You know, I'm ready to take on the judge if the judge is wrong. Because at that point, it's not about me. It's about what my client needs and what the law allows. And I love that.

Kyle McEntee:

So I wanna talk a little bit about that implied humility. You're recognizing that you don't know stuff until you're going out and learning it. What are the steps you take to learn what you don't know?

Rob Anderson:

Read through whatever's been filed already, if anything has been filed. Then I immediately call Kimber and ask her, “have you ever heard of this? Have you done this? Have you seen it?” Sometimes she's seen it. Most of the time she's like, “no, I don't know. What do you think?” And we'll use our general knowledge of whatever area of law to spot the issues and to kind of narrow our focus.

Depending on what's going on, we might assign it to the law clerk to do some research. Sometimes I'll go to the rest of my brain trust, my mentors, and just kind of get a feel for, okay, am I approaching this the right way? Then I delve deep into the research, case law, statutes, and then I talk to my client, kind of get a feel for what it is that they're looking for and make sure that I'm on the right page for them.

I always front it with my clients. If it's a novel issue for me, I'll say, I'm a pretty good attorney, but I've never seen this before. I'm more than happy to research it and figure it out for you. But I just need to be a friend with you that I've never seen this before. I know that that right there in and of itself instills confidence in clients because they recognize that I know my own limits. But they also recognize that I'm willing to dig deep and get it done. I'm not necessarily better at this than anybody else, but I do have my strengths. Our unofficial motto for the firm is, “fuck it, we'll figure it out.” And that's what you have to do when you have a mid-career attorney who hasn't practiced in a while and a newly-minted attorney who's never practiced starting a firm. You just have to recognize that you don't know what's going on and you're gonna have to figure it out. So that's just our approach to everything.

Kyle McEntee:

All right, so let's go back to the beginning a little bit. So now your firm is criminal defense and family law primarily, but you started in a fairly narrow niche, criminal expungement. Why start there?

Rob Anderson:

So our firm started in a legal incubator through the Chicago Bar Foundation called the Justice Entrepreneurs Project. When Kimber and I thought up the firm, we wanted to do criminal defense. And I signed up for the Justice Entrepreneurs Project, hoping to be paired with an organization that did criminal defense, so that I could be trained on that. And I was, but their director of training quit, like a week before I was supposed to start. And the new guy just did not feel confident to train someone who had no criminal defense experience.

So I ended up being paired with the criminal records team. At the time I felt cheated. I'm not gonna lie, I felt cheated because I was there to learn criminal defense. I was telling everyone that I was starting a criminal defense firm, but I had to pivot. I actually learned a lot about the importance of expungements and other forms of criminal records relief. Once I understood the formula, because I was going to court every day, to argue these motions that I was filing. I was like, okay, this is courtroom experience that I need. I brought Kimber in and we started working on it together. Then she started doing it independently. That just put us in a place where we were able to get criminal defense clients. It also allowed us to get some early wins in our law firm career. We also knew that with the legalization of cannabis in Illinois, that there was going to be some criminal records relief for people with cannabis convictions. And then we wanted to be able to hit that market and try to corner that.

Kyle McEntee:

So did you expand from that market because you just wanted to have a broader set of cases you worked on, or was it that it was just not profitable enough for two people to only be working on that?

Rob Anderson:

I think that we never wanted to just be a one practice area firm, we never expected that. We were always going to expand. We just didn't know how to practice any other area. So we started and then when you go into court for criminal records relief, you see these cases going on around you. You see the techniques lawyers use. You end up meeting people so then you can build mentoring relationships. And we always thought that we would just like grow into a big firm and have a whole bunch of associates and different levels of partners and things like that. We're not opposed to that, but there's something about just the two of us working together, just like being able to be free that I think has changed from when we first started the firm. We're like twin flames and we understand each other implicitly. So we're able to move. I never thought that we were going to do family law. I pushed hard against it. But then, you know, with the lockdowns happening, Kimber was very astute when she's like, people hate their families. They don't like spending time with their families. So they're definitely going to want to get divorced. And she was right. So we made that pivot because people couldn't really pay for criminal defense when people were like, lockdown and not working. And so it was hard for us to like collect money during that time. So we just had to pivot. Family law started paying the bills. So we focused on that. I started taking more DUIs because again, being locked up with your family, people were drinking and we ended up getting a lot more of those cases and we were able to expand in that way.

Kyle McEntee:

So take me through a DUI case. What is the first thing you do with one of those clients when they come in the door and say, Hey, I got in trouble. I was drinking.

Rob Anderson:

So the first question I ask is, do you have a CDL? Because those require different tactics. And what's a CDL? A commercial driver's license for buses, you know, vans, cross country, transport, all of those things. So there's specific rules for them that are much more punitive than for someone who just has a standard driver's license. And that's even if they're not driving commercially at the time, like if they're just in their residential vehicle. Right. Those rules apply to them at all times. With those cases, I tell the client, we're going to trial. Like you, there's no plea deal that I can get you that will let you work. We're going to trial.

Whereas with someone who just has like a regular driver's license, they don't want to spend all the money. They really just don't want to DUI. I will discuss the options. We can try to negotiate a plea deal. We can wait for the discovery and go to trial. And then I asked for copies of their tickets so that I can see when it was filed in Illinois. There's an administrative suspension of your license that happens when you're charged with the DUI. And it takes effect, I believe, 45 days after they sign the paperwork. So you have 30 days to file a petition to rescind the statutory summary suspension. And that's my first step in every case. I file that before I get any discovery or anything just based on my conversation with the client. And then we set that for a hearing because the goal is to try to get them their license back.

Then if we're successful, great, they can drive, they can do whatever they need to do. If we lose that, if they're not a CDL holder, we probably will do an ATIS where you're assessed for whether you have a drinking problem, what's your likelihood to commit a DUI in the future based on your drinking habits and things like that. And then that's usually the basis for negotiations. Otherwise I'm just going into court, demanding trial, demanding discovery and reviewing the discovery, seeing if the officer followed the protocols, if there's any way to poke holes in the case. So you mentioned at the top of the episode that you've not lost a DUI trial. Is that because you're only going to trial when, you know, the client's very likely to win? So I have had a couple of DUI trials where we went to trial because we had to, like it was the only option. And I didn't necessarily think I was going to win. I was hopeful and I knew that I had strong arguments but I was just like, I'm not sure what this judge is gonna think. Cause these are bench trials usually because sometimes they're very technical arguments. And so I would rather the judge get the job of figuring out what happened.

Kyle McEntee:

Is the choice up to your client as to whether it's a bench or jury trial?

Rob Anderson:

It is. When I approach cases, I always let my client know, this is your case. I'm here to give you advice. I think you should take my advice. But if you choose not to, that's on you.

Kyle McEntee:

And you'll do your best with what you're given.

Rob Anderson:

Absolutely. Unless it's just like, I really cannot work with this. And then I'll let you know like, hey, we're not a good fit. I'm not the attorney for you. You don't like my advice. You don't want to do what I think is right. So, you know, I'll leave you here so you can go and get the lawyer who works for you.

Kyle McEntee:

You mentioned that one of the reasons you recommend a bench trial, in other words, a trial overseen by the judge where the judge is the finer effect than the adjudicator because it can be highly technical.

Rob Anderson:

So I have a great example. I had a DUI case this summer and I had a high school intern. There were other high school interns in the office. So I gave them the discovery and I asked them to look it over. My intern who is turning 18 and could be on a jury pretty soon, looked at that and said, “oh, your guy's going to jail.” Now, Kimber and I had looked at this discovery and cackled because we were like, this is a weak case. So then I gave her some additional context. I was like, well, okay, our client was pulled over for a DUI, but he literally does not drink. So what's there? And she's like, “well, he blew.” And I was like, okay, so here's the statute, look at the statute and let's figure out what the elements are. There's a couple of things you can be charged under for a DUI, but one of them is like a catchall that everybody uses. But with that one, the state has to prove that the person had consumed alcohol. It's not just like, oh, they were driving crazy, they were doing this, like, no, you have to prove that whether they were under the influence of something, you specifically say it was alcohol. And if you can't carry that element, obviously it can't be a conviction. Like the person could be high or on anything, but if it's not alcohol, you can't sustain this charge.

But I was like, okay, what are the elements that the state has to prove? So we went through it together, I talked to the kids and I was like, hey, these are the elements. Now look at the discovery. What did they give you that proves this? Who's in control of the car? Were they under the influence of alcohol? Things like that. And she's like, well, he was obviously driving. We have that on video. I was like, okay, so they can prove that element. Now let's get to the alcohol. How do they prove that? And she says, well, he blew. I said, right, but I gave you some information that told you that that initial breathalyzer isn't a breathalyzer. So it's not admissible evidence. So throw that out the window, now what? Look at everything else you have, what do you think? And she's like, well, I mean, the cop pulled him over, so, you know, he probably was under the influence.

Now, I know something about this particular trooper that lets me know that that's not the case for him. I've been in a courtroom with him where he had eight trials in a row and not one was found guilty because he charges everyone with DUIs. You know, I told her, I was like, okay, well, this man charges everyone with DUIs, whether the proof bears it out or not, what do you think of that? And she's like, well, I think he's going to jail. So I went to court on this case. I was supposed to go to trial while she was still interning, but he ended up getting kicked because this trooper charges everyone with DUIs. But like listening to her and the other students and other lay people, I'm like, oh yeah, this is an argument that is a little technical.

So I showed them another one where my client had some cognitive issues and he had been shot. So he had issues with controlling his hands sometimes. So when he gets out of the car because he got shot in the face, he slurs. No matter what's going on, he slurs. He can't take a breathalyzer because he produces too much saliva. I thought about taking that to a jury trial because that's what he wanted. And I was like, I just don't think that you should do this, man.

We won the trial, the bench trial, but the judge told us, he said, sir, I can't find you guilty of this charge, but I do believe you were under the influence of something. The state just didn't carry its burden. And so in a situation like that, I think that a jury probably would have convicted him.

Kyle McEntee:

Because they would have seen themselves as doing justice instead of on the law.

Rob Anderson:

Exactly. And that's why a lot of times I'll go to a bench trial.

Kyle McEntee:

I want to move a little bit to the business of running your law firm. I think it's really interesting that you all use a transparent pricing structure. Can you talk a little bit about that?

Rob Anderson:

I know that there are times when I get completely distracted and I'll be working on one document and then I'll start working on something for another case. And so billable hours seemed too cumbersome in that way. But also as I thought about what a billable hour would mean to a client. A lot of times they have no idea how long the case is gonna take. I'm gonna charge you $350 an hour. So you pay this five or $6,000, $10,000 retainer, you're thinking, great, my case is covered. You're calling your attorney, you're checking in on your case. You don't necessarily recognize that, oh, this is part of an hour. Not that that's inherently unfair that you're charged for that, but I just don't think it's fair to a client to get them to agree to a payment structure that they just have no way of conceptualizing how much it's going to cost. But I also believe that by charging by the hour, we would end up robbing ourselves in the future and robbing our clients in the present.

So if we charge a flat fee based on our experience here and the value that we're giving the client. Fine, they're not cheated. They know what to expect. I know what to expect. And as I improve, my profits can grow without harming my relationship with my clients or future clients, because they know what they're gonna pay. I know what they're gonna pay. And as I improve and I gain expertise and I build forms and templates and things like that. I'm not cheating myself. I'm making more money as I become more efficient, as I learn more.

Kyle McEntee:

And it's not only all those things you mentioned, but it's in the future. If you hire a junior associate or continue to rely on high school or college or law student interns, you can use them on cases and that's all rolled in and that leaves you more time for the more technical aspects.

Rob Anderson:

Yes. But flat rate doesn't work for everything either. And that's one thing that we've learned with our transparent pricing. If you don't charge the right flat rate, you're working for free. You might even be paying to take on a case. And in some instances, that's fine. You know, if it's your first time doing it, you don't necessarily know how to price it. You don't know how much work goes into it. So that's fine. But clients will not pay as they're supposed to, which, of course, screws up the cash flow and the systems in the firm.

So, you know, we're exploring some other payment. They're still flat fees, but they're not. But they're like phased flat fees. So like for a felony case. Let's say you call me as soon as you get out of the police station. Okay. So there's several different parts to this felony case. There is a preliminary hearing. I'll charge you for the preliminary hearing. If you don't want me to proceed after that, that's great. I'll withdraw. You don't owe me any money. If you want me to continue, okay, the next phase is discovery. I'll file my discovery motion, my appearance, and I'll get discovery. I'll review it. I'll have my staff review it. We'll come together. We'll conference it. And then we'll tell you what our findings are.

You can have us withdraw at that moment. Nobody's prejudiced. It's not slowing down the process. And you have an understanding. Okay, if you want us to file motions based on our recommendations, then we charge you for the motions that we file. So, at every step, you know what it is that you have to pay. And you also recognize that if you don't pay, we're not going to continue. And I believe that that adds another layer of transparency for the client. It gives them another option on whether they want to proceed or if they're just gonna go and do whatever else they wanna do. But it also gives us places where we're not stuck on a case where we're no longer getting paid, which I mean is a big deal in criminal cases because there's no such thing as a limited scope criminal case in Illinois. If you're on the case and it starts going towards trial, you're on that case. So we have points of withdrawal and points of payment at the same time.

Kyle McEntee:

And I'm guessing that in the very first consultation, you're telling them the whole schedule of possible payments. It's not like you're surprising them after each step.

Rob Anderson:

Right, so this is new for us. What I'm working on is like a case roadmap for like felonies in general, misdemeanors in general, traffic in general, a DUI in general. You'll see, okay, here's this step. This is phase one, phase two, phase three, whatever. And it tells you what the price is. And then it'll tell you what the total price is at the end. You know, it'll add it up so you can kind of see like, okay, this fell in case is going to cost me this much. And so that'll be part of your like welcome packet and your engagement letter, but you can have an understanding of what's going on.

Kyle McEntee:

So during the previous episode, we discussed rather extensively the stigma of doc review. So not only were a lot of the work environments dehumanizing, but people really looked down on you for the work. And that was a surprise to you. And I think you let it roll off your back really well. But in the legal world, those negative opinions can have undesirable implications. Now, as you look back five years later and you spent a few years on the circuit, how do you now reflect on that time?

Rob Anderson:

It's still weird to me that there's a stigma, because I look at myself, I look at Kimber, I look at other people I know who were on the circuit, who started firms, are out there killing it. I also think it's very weird because a lot of times when I was doing that work, I was working with second and third and fourth and fifth year associates at biglaw firms who were basically doing the same thing that I was doing. They just got paid a lot more to do. But they kinda felt like they could look down on me. I'm like, we're literally negotiating a contract together. Because I see people who do not want to do that, but they have internalized this idea that that's all they can do, that they can never go get a job at a firm. They've been doing document review too long. And some people love it. I get it. I loved it for years. It was so flexible. It was great. I got paid when I needed to. It was great. It didn't pay enough, which is why we left and started the firm.

But, you know, I think the document review did a lot for me. It gave me an understanding of legal documents, legal terminology. It gave me the chance to just interact with attorneys on a regular basis in a way that I had never had before, because they were either my mentors or my supervisors. Whereas these people were my colleagues. You know, a lot of people who do document review have a lot of experiences that a lot of people can learn from. And I learned a lot. And I've gotten a lot of referrals from people that we were on the circuit with. When they start firms, they're like, hey Rob, I followed you, I started a firm. And I'm like, oh, what are you doing? Let me know, like, so I can send you some cases when these folks call me.

You know, one of my friends that I met on document review, she just passed the bar. Now, once she gets sworn in, she's gonna like do some drafting for us. She's like, I wanna open up a criminal offense firm. Like, are you okay co-counseling a few cases with me? And I'm like, absolutely. Just seeing Kimber and I go and start this firm and it lasts so long. She's like, I'm gonna do that too. I just think that more people need to respect that it's like just a stop.

Kyle McEntee:

So how did you avoid internalizing?

Rob Anderson:

Even though I'm not like an arrogant person, I have certain confidence in my own abilities and my skills that I've picked up. I mean, Kimber is one of the smartest people I know and her legal mind is amazing. The fact that she was doing document review, I was like, this brilliant person is doing it. We're clearly not just the dregs of the legal society like people would have us believe. Having her around and just the many friends I've made during the doing document review and like hearing about the firms they had started and closed down. Like I met a lot of retirees who were like, “yeah, I had a firm for years. I got tired of it, but I still don't wanna be sitting at home. So I do document review.” And like those folks, like they encourage you and they're like, “oh man, you should do this.” You should do that. You need forms. I got forms. I'll help you out. And I think that just going in there and not feeling down on myself helped me to connect with the right people and be able to move past that. I mean, since we started the firm, both of us have gone back to document review during lean times because it's like, there's money here.