In this episode, Steve Fretzin and Matt Darner discuss:

  • Challenges attorneys encounter in chasing overdue client payments
  • Building strong systems, processes, and roles to keep law firms efficient
  • Psychology and communication dynamics that shape how clients pay their bills
  • Lessons learned from business mistakes and the growth unlocked by niching

Key Takeaways:

  • When lawyers delay or inconsistently send invoices, clients subconsciously perceive the firm as disorganized, which weakens professionalism and makes collecting payment significantly more difficult later.
  • Establishing transparent expectations with clients about how billing and payments will work from day one creates accountability, prevents confusion, and reduces the risk of overdue receivables.
  • Shifting accounts receivable follow-ups away from attorneys and onto trained specialists or outsourced support ensures that lawyers can focus on high-value legal and business development work rather than chasing payments.
  • Narrowing focus to serve a single type of client—such as law firms—can dramatically accelerate growth, create clearer messaging, and lead to deeper expertise that builds stronger client trust and results.

“If you’re not invoicing regularly, it is communicating something is wrong with your business, whether you know that or not.” —  Matt Darner

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About Matt Darner: Matt Darner is the Co-Founder and Vice President of Business Development at CollBox, a platform built to help law firms and professional service businesses recover what they’re owed without straining client relationships. Over the past decade, he has focused on blending technology with a human touch to simplify accounts receivable and give attorneys back their time. With a background in sales and business growth, Matt understands the challenges firms face in scaling while staying profitable. His mission is to ensure that hard-working professionals get paid faster and more reliably, allowing them to focus on the work they do best.

Connect with Matt Darner:

Website: https://collbox.co/

LinkedIn: https://www.linkedin.com/in/matthewdarner/

Connect with Steve Fretzin:

LinkedIn: Steve Fretzin

Twitter: @stevefretzin

Instagram: @fretzinsteve

Facebook: Fretzin, Inc.

Website: Fretzin.com

Email: Steve@Fretzin.com

Book: Legal Business Development Isn’t Rocket Science and more!

YouTube: Steve Fretzin

Call Steve directly at 847-602-6911

Audio production by Turnkey Podcast Productions. You’re the expert. Your podcast will prove it.

FULL TRANSCRIPT

Steve Fretzin: [00:00:00] Hey everybody, Steve Fretzin, and welcome to the Be That Lawyer Podcast. So happy that you’re with us. I’ve been doing this for a long time now, about six years, 540 shows, something like that. I love interviewing people. I got Matt waiting in the wings, ready to show us his brilliance.

Steve Fretzin: [00:00:23] How you doing, Matt?

Matt Darner: [00:00:24] I’m doing well, Steve. Thanks for having me.

Steve Fretzin: [00:00:26] Good to have you, man. We are going to have a lot of fun today talking about money and AR and all kinds of stuff. By the way, a topic we don’t really bring up too much on the show, but really an important one, so we’ll come back to that.

Steve Fretzin: [00:00:36] I want to remind everybody of two other, three other resources for growing your law practice. Be That Lawyer, the book, 101 Top Rainmaker Secrets for Growing a Successful Law Practice, available on Amazon. If you don’t want to pony up the dough and you just want an ebook, you can just email me at Steve at Fretzin and I’ll shoot one off to you.

Steve Fretzin: [00:00:54] Not a problem. But it’s probably best to have the book. You’re supporting my son’s 529 plan. He’s at Colorado State now and we need all the help we can get. If he goes to grad school, we’re, we’re fine. And then of course we’ve got our Be That Lawyer Coaches Corner with Steve Fretzin and the other Be That Lawyer podcast.

Steve Fretzin: [00:01:13] Check that out. And by the way, if you haven’t been to my YouTube channel, just type in Steve Fretzin on YouTube. I want to say 600, 700 videos. Podcasts, training videos, all kinds of really cool stuff. You could take a deep dive. If you go deep enough, you’ll see me without a beard and a little bit of a baby face, and that’s no good for anybody.

Steve Fretzin: [00:01:32] But that’s there too if you want to take a deep dive. Alright, Matt, that’s all I have to say about that in the immortal words of Forrest Gump. Let’s start off with our quote of the show, which is one of my favorite segments, and it keeps getting better because I’m hearing all these quotes that I’ve never heard before.

Steve Fretzin: [00:01:48] This is a great one. This is what Red Adair said: If you think it’s expensive to hire a professional, wait until you hire an amateur. I totally get that. Welcome to the show, and tell us a little bit about that quote.

Matt Darner: [00:01:59] Yeah, absolutely. Thanks, Steve. I appreciate it. You know, so the story of Red is he’s like this famous hell fighter, was what he was called. Right? So this is a guy who would come in and put out fires on oil rigs, like major fires. The bravery and maybe the craziness of someone like that stands on its own. But what I think is interesting is the controversy, if you like, of that guy is he charged a lot for his work, right?

Matt Darner: [00:02:07] But he put out fires on these incredibly lucrative enterprises, took great care of them, and solved this massive problem by way of a raging inferno. He charged a lot of money for it, but he’s kind of famous for being amazing at that, brave, diving into these crazy things.

Matt Darner: [00:02:43] Literally the term hell fighter is pretty crazy by itself. But I think it resonates with all of us, not just you and I here, but those listening and running your firms. We all know those clients that have been just, they come in, you can tell right away when they’re just super price conscious, they’re kicking the tires.

Matt Darner: [00:03:01] It’s all about the cost. Big red flag, right? But I think for the rest of us trying to run scalable and successful businesses, you get what you pay for. And every time I’ve underinvested in a staff member or anything, it’s always bit me. Like every single time I thought I was getting a good deal, I was not.

Matt Darner: [00:03:19] Right.

Steve Fretzin: [00:03:20] Well, I don’t think anybody wants the cheapest divorce lawyer or the cheapest amateur surgeon. I think that’s right. You know, coaching too, I feel like for every one good one, there’s 10 bad ones that are out there just hanging a shingle and trying to make it happen and charging a fortune and then not really being very helpful.

Steve Fretzin: [00:03:41] So I think it’s important for people to realize, yeah, you might be paying more for someone with experience and someone that’s been doing it a while, but look, they’re going to get you there a lot faster potentially than someone who’s figuring it out alongside you. That’s right.

Steve Fretzin: [00:03:56] Really cool stuff. Hey everybody, Matt Darner, co-founder of Callbox. Give us a little bit of background of how you got into that and in working with lawyers.

Matt Darner: [00:04:05] Yeah, so, you know, the quick tone check. We’ll take over all the past due bill chasing for law firms. So accounts receivable, right, past due bill follow up.

Matt Darner: [00:04:15] Good question. How does someone get in that line of work? You joke about the beard. I had more hair when I started this company. So similar story. How does someone think that that’s a good idea? I just got fascinated early on with helping small to mid-size businesses.

Matt Darner: [00:04:34] I’ve always done this in my career, adopt better technology, better processes. I was not a finance guy, I was not a collections guy despite the bald head. I’m a teddy bear, I swear. I don’t know. But it actually started almost 10 years ago. We’ve been doing this for a long time. My co-founder, who’s my best friend of 20 plus years, but a brilliant engineer, so kind of an app builder, a platform builder.

Matt Darner: [00:04:59] And my unique skill is talking a lot. No. And so sales and biz dev, right? He got this started and brought me in quickly after. But he basically pitched an idea at an accounting conference, if you can believe it. A QuickBooks sponsored conference, to help really small businesses send their really past due invoices to collections.

Matt Darner: [00:05:21] So how do you get the really hard stuff into the hands of specialists for that? What does it even mean to find a good collection agency? Do they exist? And that was a long time ago. That’s kind of Callbox 1.0 as I like to call it. But over the journey, we just found more and more ways to serve small businesses, eventually realizing law firms were our people.

Matt Darner: [00:05:39] Like they track their time, they bill for their work, they have high hourly rates. Their time is extremely valuable. And collecting on those invoices is really painful for them, right? They want to go be great attorneys and do the legal work. The short version is no one went to law school to be a bill collector.

Matt Darner: [00:05:57] Right. Is sort of what I like to say. And that bears out. So building a platform and a service, really like an app meets a service that can take over the past due chasing, the validation has just been nonstop. Once we finally, and I’m sure we’ll talk about this around mistakes in running businesses.

Matt Darner: [00:06:16] Once we niched down, and like I said, this is who we’re for, this is all we’re focused on. The business exploded, right?


[Transcript continues…]

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Steve Fretzin: [00:06:22] Well, since you brought it up, I mean, look, some things just get away from people and AR for lawyers, sometimes they want to be a nice guy. They’re billing hours, they’re in the middle of a matter and things just get out of hand and next thing you know, it’s six months and longer, they haven’t got paid. And you know, it’s a hundred thousand, it’s 200,000. And they’re realizing, look, this is like a lot of money and it just gets harder and harder to deal with.

Steve Fretzin: [00:06:49] So what are some of the common mistakes that lawyers make that allow money to get out of hand and the AR to build? Hey everybody. Do you ever wonder why top executives and athletes are so successful? It’s typically because they have a coach, someone that is looking at them from the outside to identify their gaps, identify their potential.

Steve Fretzin: [00:07:08] That’s what I do. I’m Steve Fretzin and I’m here to help you be that lawyer. If you’re interested in a free consultation, click the link below and we’ll get together and we’ll identify where you can make improvements to be that lawyer.

Matt Darner: [00:07:19] Yeah, great question. And there’s several, and so one thing I think, and this will vary a little bit by your size of firm, right? If you’re a true solo, I feel it for you. I was doing our books like in QuickBooks when we started Callbox. I’ve been there, done that. Still wear many hats on the average day. So I get that. But whatever size of firm you are, trying to control everything inside the firm is a big mistake, right?

Matt Darner: [00:07:36] You want to have people that are good at things you’re not, and let them go be good at those things while you go be the hero and the expert on the legal matters, right? That’s why you started, that’s why you went to law school. That’s what you’re for right now. I do think, and Steve, I know you’ll agree with this, we get enriched by learning how to run a business and it can open a new dimension to us that maybe we didn’t know we had.

Matt Darner: [00:08:04] That’s certainly true for me. I think I started a business because I was a really bad employee with too many ideas and authority issues, and I was like, I gotta go try my own thing. And boy was that humbling, right? Like you learn how to go face to face with running a business, which is incredibly hard, but you know.

Matt Darner: [00:08:21] You are the expert in legal. Put the right people in position for all kinds of things. Getting the bills out the door, that’s a unique skillset. Tracking time, approvals, things like that. Following up on past due bills. That’s a different skillset. A lot of people like to throw that on their, the person doing the billing.

Matt Darner: [00:08:37] ‘Cause you think, oh, whether you’re billing, getting the bill out the door, just go follow up on it. I get the thread. But think about the skillset that it requires to get bills out meticulously, accurately, systematically. Then think about what it takes to collect on them. Systems, detail oriented, charismatic, persuasive, persistent, right?

Matt Darner: [00:08:57] And not kind of thin skinned, right? People will avoid you when you’re trying to get paid, right?

Steve Fretzin: [00:09:02] But then why, why do mid-market and even large law firms, like have their people collecting? Like, why is that a job that a lawyer who’s proficient at intellectual property at the highest level is spending countless hours chasing after his or her AR?

Matt Darner: [00:09:19] You know, before founding a company, I’m a lifelong sales guy, right? So good and the bad. I try to be the best sales guy I can be, sales guys get a bad rep and some of it’s deserved. Not all of it though. But when I think back on my best experiences with clients who are the happiest, and some of these are some of the largest deals I’ve ever closed in my career, right?

Matt Darner: [00:09:39] A lot of it is about setting really good expectations at the beginning. And then achieving those expectations, kind of whatever they are. I know, as funny as that sounds, like certainly people want a great outcome in their legal matter that’s going to have a bearing on their willingness and happiness to pay.

Matt Darner: [00:09:56] But setting clear expectations of what it means to engage with you as a professional. And we’re just clearly laying those things out. Now we can talk about the people that are going to support those expectations in that system. But your job as the first point of contact in the face of the business is, especially if you’re in that sales role, is to set expectations clearly.

Matt Darner: [00:10:16] I think when we don’t do that. And then when we get in our own head too, of feeling like the bad guy, as you pointed out in chasing the money, it just goes sideways. You start making exceptions. You don’t follow the system. You don’t follow, there is no machine. When you’re kind of winging it each time.

Matt Darner: [00:10:30] But, but

Steve Fretzin: [00:10:31] that’s my point I guess is that law firms, I think, struggle with systems that handle the AR so that the lawyer doesn’t, and granted the lawyer has to set expectations. I can’t argue with that. But the other side of it is like, it’s their own responsibility to go collect a million dollars and all the time and energy that that takes when they could be billing hours and doing business development.

Steve Fretzin: [00:10:54] So it irks me to my core when I talk to lawyers that I can just tell they’re stressed out and upset and angry because they’ve gotta go chase after this money. That’s not what they signed on for. And the law firm hasn’t put people or systems in place to essentially take it off their plate, which is, I think, ridiculous.

Matt Darner: [00:11:14] Absolutely. I mean, I think it is about investing in a lot of areas of your practice, right? But in the systems, putting the right technology, the right SOPs, and of course the right people to execute those SOPs in. And that’s what it comes down to. I think, interestingly, to me. I guess just being an outsider was not, I’ve been doing this a long time, I guess now you could say I’m an expert in AR but I never thought of myself that way.

Matt Darner: [00:11:39] When we started this, it was sort of just attacking a really interesting problem and you know, like a dog with a bone a decade later, I’m still here, you know? And so I think it’s interesting to me that we know that when we run a business, the goal of a business, at least let’s say one of the goals of a business is to make money, right.

Matt Darner: [00:11:57] To be sustainable. Doesn’t mean all you care about is money, but it is the blood of your business. You need cash to survive. It’s nothing crazy. We all know that. And yet, accounts receivable or bill chasing right, is almost one of the last things people hire for. They hate doing it the most. There’s just this deep psychology of money and psychological aversion to this task.

Matt Darner: [00:12:20] That is pervasive. And I can tell you, having done this outside of legal for a long time too, it’s everywhere. It’s every single industry, and I don’t care who you are. Most people hate calling and asking for money. That means you just need to find the right person who doesn’t mind. And actually it’s even better.

Matt Darner: [00:12:38] Think about going the last time we went to a doctor’s office, right. Every time I’ve been to a doctor’s office and it’s something like, oh, we’re going to do a test because I’m not feeling well, maybe I’m like, I don’t know if that’s covered by insurance. Like, what is this going to cost me? Right.

Matt Darner: [00:12:51] The doctor is like, I have no idea. Like they have, yeah, no, I don’t. Sorry. Like they, that culture is instilled like deeply into medical professionals that I don’t handle the billing. I’m here to be the best provider of care for you possible. And look, as a consumer, that could be a little frustrating.

Matt Darner: [00:13:09] But when you have a qualified, high quality person who will handle those questions with care and professionalism and be good at answering those questions, unlike a lot of our medical billing experiences I’m sure we’ve all had, then that can be a very good experience. You maintain arm’s length.

Matt Darner: [00:13:26] And keep being the hero. Keep being the legal professional. It just doesn’t have to be you.

Steve Fretzin: [00:13:30] Yeah. It’d be a funny reality show if they had a doctor’s office or a hospital where they had to disclose what all the fees were as they were happening. So by the way, that ambulance you brought in before we move you into a room that’s going to be, you know, $4,500 cash, check or charge.

Steve Fretzin: [00:13:48] And then, by the way, okay, we did that procedure, 75, get some door.

Steve Fretzin: [00:13:52] Right? And just watching everybody’s head explode as they realized, like how much we’re actually, you know, and on screen we like tabulate the number. Yeah, right. No, that would be a little side, little sidebar.

Steve Fretzin: [00:13:56] Like a, you know, like a TikTok video or something.

Steve Fretzin: [00:13:58] Exactly. But there are behaviors that law firms are engaging in that probably get in their own way of getting paid. What are some of those things that they probably shouldn’t be doing, but they’re doing that end up making it even more challenging. If you’re a rainmaker and you’re feeling like you’re on an island, you don’t have anyone to share your ideas with, solve problems with, you’re going to want to check out my rainmaker round tables, click the link below and learn more.

Matt Darner: [00:14:30] Yeah, I think we normalize a lot of bad behavior from our clients, right. And in a way that we don’t engage in with any of our vendors or our, you know, we all pay our electric bill on time, our mortgage or what have you. We assume that what’s up with that? Yeah. I pay all my bills on time and never think twice about it.

Steve Fretzin: [00:14:42] And then lawyers don’t get paid. Explain that.

Matt Darner: [00:14:45] Yeah. And so I think it’s interesting there are, there’s so many different classifications. If you want to use like a term of art, of debtors, people who owe the money, right? But they’re your clients, right? Debtor feels a little rough, you know? But when we talk about it from a statistics perspective, there are different types of debtors, there are different types of clients, most overwhelmingly are not malicious or willful, like trying to, you know, to screw out of your money or anything like that.

Matt Darner: [00:15:09] But when you don’t present a well-oiled machine with high, clear expectations and then reinforce it. Maybe that’s even the most important part here that in my world is clients get away with whatever we all kind of do. Right. Well, if you don’t send me the invoice, then, so this goes upstream from us right?

Matt Darner: [00:15:29] On the follow up side. If you don’t even bill on time. How am I that you are literally, you know, sort of quietly, you know, telling me that you don’t really care about getting paid, right? If I, and they internalize that, like, whether you think you’re saying it or not, you are saying it when you don’t get your billing out on time, and reliably.

Matt Darner: [00:15:49] So I’m sure you have tons of thoughts on this too, Steve, but I feel like people, some people struggle, like in my world, I think you should bill weekly or biweekly. It depends on practice area and your velocity of work, but biweekly.

Steve Fretzin: [00:16:05] Meaning twice a month.

Matt Darner: [00:16:07] Correct. Okay. Yeah, with that, that’s always a fun semantic game too with that one. Fortnightly. No, I’m kidding. No, but yes, so more frequently than monthly. That said, and this is not that controversial, but I think some people are so locked in on biweekly or weekly that I say, look. But if you can’t get monthly, right? Start there. Like, it’s like me, I’m bigger guy.

Matt Darner: [00:16:27] I’m like, I’m going to lose a hundred pounds. It’s like, why don’t we lose like five first? You know? Yeah. Let’s just, how we do baby steps, like small pieces, right? Like let’s go. And so get monthly down like a science, because if you’re not invoicing regularly. It is communicating something is wrong with your business, whether you know that or not, or think about it like that or not.

Matt Darner: [00:16:44] So that’s one major up the chain way. So track your time. Well get your bills out on a regular cadence that instills professionalism and just shows your client you’ve got it together then. You’ve got to follow up consistently as well because that reinforces that you have an expectation of being paid for your work, right?

Matt Darner: [00:17:01] Yeah. The attorney’s probably going in high confidence, we’re going to do this, it’s going to be great. They’re feeling awesome, right? Like at that moment we’re great. It is all of the systems issues that happen after that that sort of erode that confidence over time. Yeah. And then marry that with something didn’t go well with the case Uhoh.

Matt Darner: [00:17:19] Or you, I don’t know, you got really busy with your caseload, didn’t communicate very, very often or give them a good update. Now there, there’s just this mental game on the client side that’s like, I haven’t heard from them in a while. I haven’t even seen a bill. When’s the last time I got a bill from these guys?

Matt Darner: [00:17:34] You know, no one even calls, some people notice that I’m a weirdo. I notice when people don’t call me, like, because, you know, and then they, they start to build this narrative in their head of like all the reasons, what’s wrong. And then we get to justify not paying you. Right. And that’s when you’re in trouble and it’s so, so much harder to unwind at that point.

Matt Darner: [00:17:52] Yeah. I, there’s a great quote. A partner of mine who works on the billing process side, and she, she’s a great team. Her name’s RDA Prendergast. I know RDA. You know R? Yeah, Mrs. Yeah. She’s in Chicago for the tech show every year and she’s, she’s terrific. She’s been on the show.

Matt Darner: [00:18:07] Fantastic. I know, and she’s great. We just launched a partnership together and for reasons you’ll get, but we’re literally just two sides of the same coin. Right. And so, you know, at the end of the day it’s sort of like, if you’re not, think about invoices and bills, and I think of this with like sort of the, the soft touch collections calls.

Matt Darner: [00:18:25] It’s a customer service touchpoint is actually what it is. And get, get, get out of your own head on like, oh, they’re, I’m harassing them, I’m bothering them. Well, you could be if your approach is wrong, but it doesn’t have to be that way. Right. So when you send an invoice. It tells them what you’ve been up to.

Matt Darner: [00:18:41] Right? So it’s literally, Hey, we’re showing off all the great work we did. I know there’s a bill attached. I know that’s a little uncomfortable, but it is similarly an opportunity to say, look at everything we just did in this period of time for you. Yeah. Awesome. The follow-up phone calls are similarly, you know, I trained my team to say, Hey, you know, it’s Matt calling on behalf of a BC law.

Matt Darner: [00:19:00] I’m just checking in on invoice 1, 2, 3. Did you get that? Do you have any questions? I’m sure you just missed it or something. What’s going on? Anything I can help you with? You almost do this sort of assumptive, like, oh yeah, I know you’re going to pay. It’s not about that, it’s just, oh, you probably, you probably missed it.

Matt Darner: [00:19:14] I’m just checking in what’s going on. How you feeling? Right. It, it’s very soft. More professional sounding than that. I’m winging it a little, but, how you doing? No, it’s, we don’t, it’s not a Moffitt, how you doing? No, but, what I,

Steve Fretzin: [00:19:26] But what I liked what you said was you sort of, you know, you probably already got it, or it’s our, maybe it’s our mistake.

Steve Fretzin: [00:19:32] Like there’s certain language that softens up that it’s not, Hey, you suck and you haven’t paid, and where’s my damn money? Right. More like, you know, Hey, this is probably on us, or it’s probably a mistake. Or, I don’t mean to, you know, be a pest, but we’re looking to see, you know, and just, just kind of easing your way into it a little bit.

Matt Darner: [00:19:50] And that’s the way you start, right? Because I think that’s something a lot of attorneys worry about. Oh, they’re going to be so, like, the feathers are going to be ruffled. Yeah. They’re going to be so upset. Well, yeah. If you do it wrong. Sure. But that’s why it’s a skill, you know, that you need to invest in or, or have a person or a, a, you know, a process to do that.

Matt Darner: [00:20:06] And so yeah, it’s, oh my mistake, our mistake just checking in. You probably didn’t get it very, very soft. Almost like, oh wow, you know, silly us, right? And then we gently escalate, but when you don’t make follow up phone calls consistently. You can’t escalate it. Right. And, and the reason is, I, I have a lot of consults with attorneys who know they haven’t followed up on this client in six months.

Matt Darner: [00:20:28] Now you’re in your own head. Think about your to-do list, right? Oh my God, that thing I’ve been putting off for six months. And then you think about how long you’ve been putting it off, and then you just go, you psyche yourself out and don’t do it even further. Yeah. And then you wake up a year later and it’s just not, it’s still not done, but it took 30 seconds right.

Matt Darner: [00:20:44] To do it. Like that’s accounts receivable in, in some ways. But when you consistently reach out, then you can build and ask, gently escalate the language because you know, and you have full confidence. Wow. We followed up 12 times with this client and emailed them. They have the bill. We’ve given them every possible opportunity to communicate if we did something wrong.

Matt Darner: [00:21:07] Yeah. You know, hopefully that’s not the case. And then I think that will build your confidence up to say, well now we’re going to, now we’re going to maybe turn up that temperature a little bit. The case. Yeah. I mean, you’re, you’re going to pull,

Steve Fretzin: [00:21:17] You’re going to stop producing, you know, work right for them and consequences now.

Steve Fretzin: [00:21:21] Right?

Steve Fretzin: [00:21:22] Absolutely. You

Steve Fretzin: [00:21:23] know, but you know, I think before it gets out of hand, let’s go back to the beginning for just a moment and then we, we’ll, we’ll go back to the end. But

Steve Fretzin: [00:21:31] Yeah,

Steve Fretzin: [00:21:32] You said something important at the beginning of the show, which was about setting clear expectations about how we’re going to work together and how the bills get paid.

Steve Fretzin: [00:21:42] And it’s not the easiest conversation, but I think it’s an important conversation because the, the not setting expectations allows for things to slip through the cracks and bills not to get paid. So I think it’s not only setting expectations about how the bills will go out and how we’re going to get paid and how this is going to work.

Steve Fretzin: [00:22:02] Getting agreement from them that that’s, that’s okay. And that they’re going to do it. And maybe even like, and if for some reason you miss a payment or something happens, here’s how we’re going to respond. Can you just kind of add a little more color to that?

Matt Darner: [00:22:15] Absolutely. You know, I think at its core an AR workflow is just a series of if not here, then what? Okay. And if we didn’t get paid here, then what? And if, and as many of those as are appropriate for your practice area and peppering. And you know, something you said made me think of this in terms of mistakes and processes, that firms make is they lose their leverage. Right.

Matt Darner: [00:22:33] And they, they basically give away all the legal work without getting fully paid for it. Right? So that’s part of the story too. So communicating. Along this timeline, here’s what happens. And hey, if you miss a payment, we got you. Here’s some, some opportunities, payment plans, how to get caught up. And it’s friendly at that stage.

Matt Darner: [00:22:51] Like, and, and plan for it, right? Know what you’re going to do if they fall off track because it will happen. It’s, it’s a numbers game. But have it documented so every member of your team knows. If A, B, or C happens, here’s how we react. It’s not a go bug, the partner or the attorney or anyone else, right?

Matt Darner: [00:23:09] Of like, what do we do now? It’s just moving. And there are not that many implementations of this, right? But people fall behind. Do we allow them to get onto a payment plan to catch up? How do we structure that at what amount of time? And then I think along the way, it’s really, really critical that.

Matt Darner: [00:23:27] We know when the point of no return is right there needs, it’s going to vary by practice, area, jurisdiction even, right? Like so take family law, which we see a lot of, right? You can’t always pull out of the case. Right? Like there’s a point in time in some, some places maybe never. And that, that’s hard. You got to be really careful.

Matt Darner: [00:23:44] In those jurisdictions, right? But most of, most places you can, but not infinitely, so, right. Not once you’re really in, in the thick of it, ahead of a trial, hearing an appearance, you know, when is the bill going to pop? Right? You need to make sure that it’s all green flags. For every client leading up to that sort of thing.

Matt Darner: [00:24:01] Yeah. And if it’s not, when are we going to pull the plug? I think so many people are afraid to do that and then they wake up, you know, okay, we’ve got $2,000 in trust. It’s supposed to be 5,000. I’m just making up some numbers here. But there’s, you know, a thousand or 2000 in work in progress we haven’t billed for yet.

Matt Darner: [00:24:19] Then there’s another 2000 in unpaid bills. We’re, we’re, we’re reluctant to draw down on the trust because we’re trying to hang onto that for, you know, a rainy day. But the rainy day is already here. Then we have a hearing coming up and we know that that’s on average going to pop 10 K, 15 K. And then you’re on the hook for it all.

Matt Darner: [00:24:35] And then you wake up, you know, and I have that conversation with you. You have $30,000 owed to this client, the matter’s over now, maybe even they had a great outcome, right? But even harder if they didn’t. And now what are we going to do? Right. It’s a ball of yarn.

Steve Fretzin: [00:13:30] Yeah. It’d be a funny reality show if they had a doctor’s office or a hospital where they had to disclose what all the fees were as they were happening. So by the way, that ambulance you brought in before we move you into a room that’s going to be, you know, $4,500 cash, check or charge.

Steve Fretzin: [00:13:48] And then, by the way, okay, we did that procedure, 75, get some door.

Steve Fretzin: [00:13:52] Right? And just watching everybody’s head explode as they realized, like how much we’re actually, you know, and on screen we like tabulate the number. Yeah, right. No, that would be a little side, little sidebar.

Steve Fretzin: [00:13:56] Like a, you know, like a TikTok video or something.

Steve Fretzin: [00:13:58] Exactly. But there are behaviors that law firms are engaging in that probably get in their own way of getting paid. What are some of those things that they probably shouldn’t be doing, but they’re doing that end up making it even more challenging. If you’re a rainmaker and you’re feeling like you’re on an island, you don’t have anyone to share your ideas with, solve problems with, you’re going to want to check out my rainmaker round tables, click the link below and learn more.

Matt Darner: [00:14:30] Yeah, I think we normalize a lot of bad behavior from our clients, right. And in a way that we don’t engage in with any of our vendors or our, you know, we all pay our electric bill on time, our mortgage or what have you. We assume that what’s up with that? Yeah. I pay all my bills on time and never think twice about it.

Steve Fretzin: [00:14:42] And then lawyers don’t get paid. Explain that.

Matt Darner: [00:14:45] Yeah. And so I think it’s interesting there are, there’s so many different classifications. If you want to use like a term of art, of debtors, people who owe the money, right? But they’re your clients, right? Debtor feels a little rough, you know? But when we talk about it from a statistics perspective, there are different types of debtors, there are different types of clients, most overwhelmingly are not malicious or willful, like trying to, you know, to screw out of your money or anything like that.

Matt Darner: [00:15:09] But when you don’t present a well-oiled machine with high, clear expectations and then reinforce it. Maybe that’s even the most important part here that in my world is clients get away with whatever we all kind of do. Right. Well, if you don’t send me the invoice, then, so this goes upstream from us right?

Matt Darner: [00:15:29] On the follow up side. If you don’t even bill on time. How am I that you are literally, you know, sort of quietly, you know, telling me that you don’t really care about getting paid, right? If I, and they internalize that, like, whether you think you’re saying it or not, you are saying it when you don’t get your billing out on time, and reliably.

Matt Darner: [00:15:49] So I’m sure you have tons of thoughts on this too, Steve, but I feel like people, some people struggle, like in my world, I think you should bill weekly or biweekly. It depends on practice area and your velocity of work, but biweekly.

Steve Fretzin: [00:16:05] Meaning twice a month.

Matt Darner: [00:16:07] Correct. Okay. Yeah, with that, that’s always a fun semantic game too with that one. Fortnightly. No, I’m kidding. No, but yes, so more frequently than monthly. That said, and this is not that controversial, but I think some people are so locked in on biweekly or weekly that I say, look. But if you can’t get monthly, right? Start there. Like, it’s like me, I’m bigger guy.

Matt Darner: [00:16:27] I’m like, I’m going to lose a hundred pounds. It’s like, why don’t we lose like five first? You know? Yeah. Let’s just, how we do baby steps, like small pieces, right? Like let’s go. And so get monthly down like a science, because if you’re not invoicing regularly. It is communicating something is wrong with your business, whether you know that or not, or think about it like that or not.

Matt Darner: [00:16:44] So that’s one major up the chain way. So track your time. Well get your bills out on a regular cadence that instills professionalism and just shows your client you’ve got it together then. You’ve got to follow up consistently as well because that reinforces that you have an expectation of being paid for your work, right?

Matt Darner: [00:17:01] Yeah. The attorney’s probably going in high confidence, we’re going to do this, it’s going to be great. They’re feeling awesome, right? Like at that moment we’re great. It is all of the systems issues that happen after that that sort of erode that confidence over time. Yeah. And then marry that with something didn’t go well with the case Uhoh.

Matt Darner: [00:17:19] Or you, I don’t know, you got really busy with your caseload, didn’t communicate very, very often or give them a good update. Now there, there’s just this mental game on the client side that’s like, I haven’t heard from them in a while. I haven’t even seen a bill. When’s the last time I got a bill from these guys?

Matt Darner: [00:17:34] You know, no one even calls, some people notice that I’m a weirdo. I notice when people don’t call me, like, because, you know, and then they, they start to build this narrative in their head of like all the reasons, what’s wrong. And then we get to justify not paying you. Right. And that’s when you’re in trouble and it’s so, so much harder to unwind at that point.

Matt Darner: [00:17:52] Yeah. I, there’s a great quote. A partner of mine who works on the billing process side, and she, she’s a great team. Her name’s RDA Prendergast. I know RDA. You know R? Yeah, Mrs. Yeah. She’s in Chicago for the tech show every year and she’s, she’s terrific. She’s been on the show.

Matt Darner: [00:18:07] Fantastic. I know, and she’s great. We just launched a partnership together and for reasons you’ll get, but we’re literally just two sides of the same coin. Right. And so, you know, at the end of the day it’s sort of like, if you’re not, think about invoices and bills, and I think of this with like sort of the, the soft touch collections calls.

Matt Darner: [00:18:25] It’s a customer service touchpoint is actually what it is. And get, get, get out of your own head on like, oh, they’re, I’m harassing them, I’m bothering them. Well, you could be if your approach is wrong, but it doesn’t have to be that way. Right. So when you send an invoice. It tells them what you’ve been up to.

Matt Darner: [00:18:41] Right? So it’s literally, Hey, we’re showing off all the great work we did. I know there’s a bill attached. I know that’s a little uncomfortable, but it is similarly an opportunity to say, look at everything we just did in this period of time for you. Yeah. Awesome. The follow-up phone calls are similarly, you know, I trained my team to say, Hey, you know, it’s Matt calling on behalf of a BC law.

Matt Darner: [00:19:00] I’m just checking in on invoice 1, 2, 3. Did you get that? Do you have any questions? I’m sure you just missed it or something. What’s going on? Anything I can help you with? You almost do this sort of assumptive, like, oh yeah, I know you’re going to pay. It’s not about that, it’s just, oh, you probably, you probably missed it.

Matt Darner: [00:19:14] I’m just checking in what’s going on. How you feeling? Right. It, it’s very soft. More professional sounding than that. I’m winging it a little, but, how you doing? No, it’s, we don’t, it’s not a Moffitt, how you doing? No, but, what I,

Steve Fretzin: [00:19:26] But what I liked what you said was you sort of, you know, you probably already got it, or it’s our, maybe it’s our mistake.

Steve Fretzin: [00:19:32] Like there’s certain language that softens up that it’s not, Hey, you suck and you haven’t paid, and where’s my damn money? Right. More like, you know, Hey, this is probably on us, or it’s probably a mistake. Or, I don’t mean to, you know, be a pest, but we’re looking to see, you know, and just, just kind of easing your way into it a little bit.

Matt Darner: [00:19:50] And that’s the way you start, right? Because I think that’s something a lot of attorneys worry about. Oh, they’re going to be so, like, the feathers are going to be ruffled. Yeah. They’re going to be so upset. Well, yeah. If you do it wrong. Sure. But that’s why it’s a skill, you know, that you need to invest in or, or have a person or a, a, you know, a process to do that.

Matt Darner: [00:20:06] And so yeah, it’s, oh my mistake, our mistake just checking in. You probably didn’t get it very, very soft. Almost like, oh wow, you know, silly us, right? And then we gently escalate, but when you don’t make follow up phone calls consistently. You can’t escalate it. Right. And, and the reason is, I, I have a lot of consults with attorneys who know they haven’t followed up on this client in six months.

Matt Darner: [00:20:28] Now you’re in your own head. Think about your to-do list, right? Oh my God, that thing I’ve been putting off for six months. And then you think about how long you’ve been putting it off, and then you just go, you psyche yourself out and don’t do it even further. Yeah. And then you wake up a year later and it’s just not, it’s still not done, but it took 30 seconds right.

Matt Darner: [00:20:44] To do it. Like that’s accounts receivable in, in some ways. But when you consistently reach out, then you can build and ask, gently escalate the language because you know, and you have full confidence. Wow. We followed up 12 times with this client and emailed them. They have the bill. We’ve given them every possible opportunity to communicate if we did something wrong.

Matt Darner: [00:21:07] Yeah. You know, hopefully that’s not the case. And then I think that will build your confidence up to say, well now we’re going to, now we’re going to maybe turn up that temperature a little bit. The case. Yeah. I mean, you’re, you’re going to pull,

Steve Fretzin: [00:21:17] You’re going to stop producing, you know, work right for them and consequences now.

Steve Fretzin: [00:21:21] Right?

Steve Fretzin: [00:21:22] Absolutely. You

Steve Fretzin: [00:21:23] know, but you know, I think before it gets out of hand, let’s go back to the beginning for just a moment and then we, we’ll, we’ll go back to the end. But

Steve Fretzin: [00:21:31] Yeah,

Steve Fretzin: [00:21:32] You said something important at the beginning of the show, which was about setting clear expectations about how we’re going to work together and how the bills get paid.

Steve Fretzin: [00:21:42] And it’s not the easiest conversation, but I think it’s an important conversation because the, the not setting expectations allows for things to slip through the cracks and bills not to get paid. So I think it’s not only setting expectations about how the bills will go out and how we’re going to get paid and how this is going to work.

Steve Fretzin: [00:22:02] Getting agreement from them that that’s, that’s okay. And that they’re going to do it. And maybe even like, and if for some reason you miss a payment or something happens, here’s how we’re going to respond. Can you just kind of add a little more color to that?

Matt Darner: [00:22:15] Absolutely. You know, I think at its core an AR workflow is just a series of if not here, then what? Okay. And if we didn’t get paid here, then what? And if, and as many of those as are appropriate for your practice area and peppering. And you know, something you said made me think of this in terms of mistakes and processes, that firms make is they lose their leverage. Right.

Matt Darner: [00:22:33] And they, they basically give away all the legal work without getting fully paid for it. Right? So that’s part of the story too. So communicating. Along this timeline, here’s what happens. And hey, if you miss a payment, we got you. Here’s some, some opportunities, payment plans, how to get caught up. And it’s friendly at that stage.

Matt Darner: [00:22:51] Like, and, and plan for it, right? Know what you’re going to do if they fall off track because it will happen. It’s, it’s a numbers game. But have it documented so every member of your team knows. If A, B, or C happens, here’s how we react. It’s not a go bug, the partner or the attorney or anyone else, right?

Matt Darner: [00:23:09] Of like, what do we do now? It’s just moving. And there are not that many implementations of this, right? But people fall behind. Do we allow them to get onto a payment plan to catch up? How do we structure that at what amount of time? And then I think along the way, it’s really, really critical that.

Matt Darner: [00:23:27] We know when the point of no return is right there needs, it’s going to vary by practice, area, jurisdiction even, right? Like so take family law, which we see a lot of, right? You can’t always pull out of the case. Right? Like there’s a point in time in some, some places maybe never. And that, that’s hard. You got to be really careful.

Matt Darner: [00:23:44] In those jurisdictions, right? But most of, most places you can, but not infinitely, so, right. Not once you’re really in, in the thick of it, ahead of a trial, hearing an appearance, you know, when is the bill going to pop? Right? You need to make sure that it’s all green flags. For every client leading up to that sort of thing.

Matt Darner: [00:24:01] Yeah. And if it’s not, when are we going to pull the plug? I think so many people are afraid to do that and then they wake up, you know, okay, we’ve got $2,000 in trust. It’s supposed to be 5,000. I’m just making up some numbers here. But there’s, you know, a thousand or 2000 in work in progress we haven’t billed for yet.

Matt Darner: [00:24:19] Then there’s another 2000 in unpaid bills. We’re, we’re, we’re reluctant to draw down on the trust because we’re trying to hang onto that for, you know, a rainy day. But the rainy day is already here. Then we have a hearing coming up and we know that that’s on average going to pop 10 K, 15 K. And then you’re on the hook for it all.

Matt Darner: [00:24:35] And then you wake up, you know, and I have that conversation with you. You have $30,000 owed to this client, the matter’s over now, maybe even they had a great outcome, right? But even harder if they didn’t. And now what are we going to do? Right. It’s a ball of yarn.


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Steve Fretzin: [00:24:59] So, let me ask you this, and this is maybe a little bit of getting into your business a bit. There’s collections, like it’s truest form where it’s way overdue, it’s a lot of money, it’s got to be collected. That’s not what Callbox does. Is that right? You guys? Right? You guys are more on the front end helping protect that from happening. So tell us, tell everybody a little bit about, we’ll call this the shameless plug segment or something, but like…

Matt Darner: [00:25:17] Sure, sure. So my little pun is, I like to say Callbox is like collections with the lowercase C. Right. Okay. It’s an internal process. It’s a back, we’re a back office solution. Right. We represent as a member of your team. We’re sort of a funky hybrid between just a team you could hire to make those calls for you and a tech company because we integrate directly with the practice management system.

Matt Darner: [00:25:33] We’ve got Clio, Smokeball, MyCase is coming very soon, and we also do like QuickBooks and accounting system things as well, but that’s where the source of truth is, right? So at the end of the day, you know, you track your time, you bill for it. The practice management system knows what’s due and when it’s due.

Matt Darner: [00:25:49] Well, we build all these integrations, pull that data out, and we have that system to basically route that to real human beings. North American, native English speakers, trained in accounts receivable who will make the phone calls as a member of the firm. Right? So on behalf of the firm, but also our flavor of email automation cadences.

Matt Darner: [00:26:09] We just built it all out and using all the best practices of how often should we reach out, what should we say, both in email format and phone call format. And while still respecting the tooling you use so that the same invoice PDF that you generated out of a Clio, for example, gets resent to them, not some manufactured new invoice.

Matt Darner: [00:26:28] That’s confusing and what’s a Callbox, you know, as far as the client’s concerned. And then your payment links too. So we don’t touch the money. We just take the best parts of what you’ve got and do all the parts of what you’re not doing right. And kind of plug it in. And the last thing I’ll end with on that, to end our plug, is the average AR clerk, trained in this, great at these phone calls.

Matt Darner: [00:26:48] That’s a job role that’s been around forever. But big companies, big law firms have those because they have bodies and money to throw at problems. Small to mid-size firms, 95% of firms don’t have a dedicated, what I would call a collection specialist. You might have a billing specialist, but you don’t have a collection specialist because you don’t want to pay 60 grand a year.

Matt Darner: [00:27:08] That’s what they cost. That’s what we pay. And so literally, it doesn’t make sense economically, but with these integrations, we’ve been able to have one of those reps serve 15 to 20 law firms at a time. So the cost comes way down, so. Okay. Okay. And, and plug, but yeah.

Steve Fretzin: [00:27:23] But I mean, I think what we’re looking for is we’re looking for a solution where we don’t have, it’s like anything, I’m always saying delegate, delegate, delegate.

Steve Fretzin: [00:27:29] And you know, if AR and collections is a problem and you’re not doing it, your firm sucks at it. And it’s, it’s taking up your time as a busy lawyer doing high level quality work, you know, outsource it. And, and, and, I’m sure you guys have lots of validation and testimonials and stuff like that.

Steve Fretzin: [00:27:46] You’ve been doing this a long time. Awesome stuff, and we’ll give out your digits in a minute, but let’s talk about something even more important. What’s big, what’s Matt’s big mistake?

Matt Darner: [00:27:57] There’s so many. But…

Steve Fretzin: [00:27:59] Where to start?

Matt Darner: [00:28:00] There’s so, so many. Yes. That’s certainly true. There’s a couple things I…

Matt Darner: [00:28:04] When we started this company, so going on this year, so November of 25 will be 10 years for us. We’ve been doing this a very long time. It’s only the last three or four years that we really laser focused in on law firms. Really, we’d had plenty of law firm clients over those years, but just ripped off the bandaid and said, no, this is who we’re for.

Matt Darner: [00:28:22] We’re not doing this for others. Taking that long to get to that realization and niching down, I think is probably the biggest mistake and some of it, you know, you gotta learn and you gotta go through the journey. First time founder, for me, this is my first business. You just have to learn the hard way a lot of times.

Matt Darner: [00:28:39] But once we realized and did the hard, hard work of realizing who we’re for and why we’re doing it, and really deeply understanding their businesses, it unlocked everything. You know, I think we, we launched our Clio integration two years ago, in 2023. We tripled our revenue in the back half of that year.

Matt Darner: [00:28:59] Like we integrated mid 23 and then that trip we tripled our revenue. They named us one of the best new apps in their ecosystem that year. Felt funny to be a new app when I’ve been doing this a really long time, but it was really like, wow, I think we got it right. And then the validation since then has just been amazing.

Matt Darner: [00:29:15] And so niching down, you know, I get the attraction. I did it for eight years almost, you know. Just to sort of say yes to everyone. ‘Cause I think attorneys are the same. You want to help people and yeah. You want to make some money too. Like, I don’t want to turn off a revenue channel. Yeah. But when you think about how expensive it is time-wise to try to support everyone, I like to say we were a mile wide, but an inch deep, right.

Matt Darner: [00:29:39] On all these verticals. We had plumbers and HVAC and every, everybody, I’m with…

Steve Fretzin: [00:29:43] You man. I worked in over 50 industries before focusing on lawyers and I mean, I had a local carpet cleaner named Stu. I had a Caribbean medical school, I had, you know, Chicago Tribune and a bunch of other… Cool. I actually, that’s interesting and it’s, it’s interesting to be in everything, but it’s not focused to your point.

Steve Fretzin: [00:29:59] And, has been said on this show many times. The riches are in the niches, so I couldn’t…

Matt Darner & Steve Fretzin: [00:30:04] Agree more. Throw good, good. All around my hat in there. Yeah. Yeah.

Steve Fretzin: [00:30:07] Hey man, we gotta wrap up. Let’s thank our sponsors. We got Rankings.io crushing it for firms around the country, PI firms that want to get their digital all laid out and set and social media line and everything.

Steve Fretzin: [00:30:20] The LawHer Podcast, check that out with Sonia Palmer. And of course, Legalverse Media helping people get more of an international flare from a website and getting insight to what’s going on around the world in legal. Matt, people want to get in touch with you. They want to hear about Callbox, get the details.

Steve Fretzin: [00:30:38] What are the digits?

Matt Darner: [00:30:40] Yeah, absolutely. So, you know, you can always check us out. Callbox.co, like collection box. Yeah. Find me on LinkedIn, Matt Darner. I’m happy to chat anytime, not just about Callbox, but just helping you build a better AR workflow. I also do a lot of CLE and awesome podcasts like this, so trying to spread the good word of getting people paid for their hard work.

Matt Darner: [00:31:02] If I could have one final quip. You deserve to be paid for your work. I feel like a cheerleader for you all the time. Get that out of your head. You do hard work. You bust your butt on this. You deserve to be paid for it, for sure. Doesn’t mean you have to be a bad guy either, but you deserve to be paid for your work.

Steve Fretzin: [00:31:17] Yeah. Beautiful thing. Beautiful thing. All right, well, thanks Matt. And, I’m so happy to have you on the show and sharing your wisdom. And again, this is a topic when I met you, I was like, you know, is it business development related? Is it marketing related? Well, no, it’s, but it’s business related and it allows people to focus on the things that they do best. And I think, you know, it’s such a drain, emotional drain, thinking about the money you’re owed and the people that are screwing you and all the different things that can come and the bad blood that can occur and anything we can do to avoid it or outsource it to make that pain go away.

Steve Fretzin: [00:31:36] I was all about having you on the show, man, so thank you so much.

Matt Darner: [00:31:40] No, I appreciate it. And maybe one, just final, final thing, I love. Think about what you want to do with your firm and what growth plans you have. Well now we gotta go sell all these new clients and all this additional capital. No.

Matt Darner: [00:31:54] Maybe we just start by getting paid for our work. And that’s the best investment possible for funding your growth. Right? Best money’s the money you…

Steve Fretzin: [00:32:00] Already have coming in. Just great. You gotta get it.

Matt Darner: [00:32:02] Preach. Exactly.

Steve Fretzin: [00:32:04] I’m with you. Yeah, I’m with you on that. All right, buddy. Thanks so much and thank you everybody for hanging out with Matt and I for the last 30 plus.

Steve Fretzin: [00:32:09] You know, look it, there’s just a lot of different moving parts with running a law firm, running a law practice and building your book. This is just another one that hopefully you get a couple good takeaways that are going to help you be that lawyer, confident, organized, and a skilled rainmaker.

Steve Fretzin: [00:32:25] Take care, everybody. Be safe. Be well. Talk again real soon. Are you ever curious what’s really holding you back in business development? Sometimes it’s hard to see the label from the inside of the bottle. I’m Steve Fretzin and I can help you grow your book of business. Get a 30 minute free consultation with me.

Steve Fretzin: [00:32:40] We’ll identify gaps, identify your potential, and let’s take it to the next level so you can be that lawyer. Click the link below for a free consultation.

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