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328. Settle in 60 Days: How Jon Hollan Built Kentucky’s Fastest PI Firm

Published on
May 22, 2025
Podcast Host
Chris Dreyer
Rankings.io
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What does it take to go from small-town trial lawyer to statewide trucking authority? For Jon Hollan, it’s a mix of grit, niche branding, and a relentless focus on efficiency.

As managing partner at Sam Aguiar Injury Lawyers, Jon has helped his firm dominate Kentucky's trucking niche with a mix of media appearances, lightning-fast settlements, and powerhouse litigation. He shares how his team converts $300k cases into million-dollar verdicts—and how a FedEx crash case redefined his entire career.

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In this episode, we break down:

  • Why Truck Talk works—and how attorneys can land similar opportunities
  • How to build a rapid-response legal pod that clients rave about
  • The tech, case planning, and trust that fuel high-speed settlements
  • How Jon balances media, mentorship, and managing high-value litigation
  • His system to turn young attorneys into million-dollar trial winners

Guest Details

Jon Hollan is the Managing Partner at Sam Aguiar Injury Lawyers, known for his high-stakes trucking cases and million-dollar results. He leads the firm’s litigation strategy and media outreach, including Kentucky’s weekly “Truck Talk” segment on Everyday Kentucky.

  • LinkedIn 
  • Sam Aguiar Injury Lawyers: Website | Instagram

Chris Dreyer and Rankings Details

Chris Dreyer is the CEO and founder of Rankings.io, the elite law firm marketing experts - for all your digital and traditional needs.  

  • Personal Injury Mastermind (PIM): Instagram | YouTube | TikTok
  • Rankings: Website, Instagram, Twitter
  • Chris Dreyer: Website, Instagram
  • Newsletters: The Dreyer Sheet 
  • Books: Personal Injury Lawyer Marketing: From Good to GOAT; Niching Up: The Narrower the Market, the Bigger the Prize
  • Work with Rankings: Connect

Transcript

Expand Transcript

John Hollan:

Our office gets auto cases settled within 30 to 60 days. It's unlike anything I've ever seen.

Chris Dreyer:

Welcome to Personal Injury Mastermind. Let's get into it. Settle cases in under 60 days, turn young attorneys into million-dollar litigators and carve out a brand that owns the trucking niche. Today, John Hollan explains all that and more. John is managing partner at Sam Aguiar Injury Lawyers where speed is strategy. I'm Chris Dreyer, founder and CEO of Rankings.io. If raring to move faster and win bigger, this episode is for you. Let's go. So we just had Sam on. We had a great conversation. Loved hearing about your guys' success. You got 10 plus attorneys, over 45 staff. You're doing over a hundred cases a month. But now we're going to kind of get in the weeds and you're a little bit like a local celebrity, right? Our listeners in Kentucky might recognize you from the Truck Talk on WKYT. Tell us about what Truck Talk is and how you lined up this opportunity.

John Hollan:

I guess we're going on a year now and, man, you talk about uncomfortable, a podcast is pretty easy after you get used to being in a television studio in one of Kentucky's biggest media providers. But Truck Talk, it is a three-minute segment that we do once a week. It's not necessarily getting into case specific or really traditional marketing as much as it is a opportunity for me to just talk about the trucking industry, safety principles, issues that are affecting everyday Kentuckians who wonder about these cases or have been impacted by these cases or even truck drivers in the trucking community themselves. We just talk about some of the things that we've learned about in the 10 plus years that we've been doing these cases and really advocate not only for the safety of Kentuckians, but also the safety of the trucking industry and with technology and some of the big shifts that we've had the past several years.

Chris Dreyer:

That's the big lesson I think a lot of PI attorneys miss is as a proponent of safety, you still get the accident cases. So what kind of reactions are you seeing from the community about the show?

John Hollan:

It's been really good, the outreach that even from current clients and just other attorneys that I know that see the show or see some of the segments or some of the sound bites from the show, it's mostly positive.

Chris Dreyer:

Put my marketing hat on. How do you get an opportunity like this? Transparently, is it pay to play? Is it you're invited because you're a member of the community? How does this type of opportunity occur? How could other PI attorneys in maybe their state get an opportunity to come on a big show like this?

John Hollan:

I had those same questions when it first started. So we were approached, WYMT, they're the biggest news outlet in central Kentucky. They approached us for a meeting. They had had a prior attorney partner and that had ended and they were interested in whether our office based on... We handle some cases that are pretty high profile at times, especially Sam with the Breonna Taylor case. So our firm is really well known throughout Kentucky, but we were approached, it's not free, there is a small fee that we pay to get the opportunity to do it, but really they've been really great. It's part of a program they have called Everyday Kentucky. So it airs once week and then they do a lot of different media buys, social spots along with the content as well.

But the thing that's been, I think, the most useful for us in a lot of ways is we get access to all the raw footage. So you're talking about each month 10 to 15 minutes of studio quality raw footage without the noise that they add in without some of the graphics, and we've been able to repurpose that for a lot of different ways for social platforms, YouTube, and a couple other different things that we've been trying with it.

Chris Dreyer:

Yeah, that's fantastic. I think the name of the game on social media at least is video. You don't have video on your static posts. It doesn't work anymore.

John Hollan:

I think a lot of things I've learned from you over the years and your different guests and your podcast, but just having that trust to really niche down, I'm blessed to have a lot of really good phone calls, whether it's serious car accidents or even serious premises cases, but getting to a point where I'm comfortable putting myself out there as, no, I'm a trucking attorney. I handle truck crashes in Kentucky and through the media platform that we're using. We also have a website that we've developed, semijustice.com, which is solely for our trucking brand, but when it gets going really good and things are really high, I still have trouble, I think, trusting it at times. How do I say no to some of these other cases that either people who are injured want me in or other attorneys want me in? It's a learning process.

Chris Dreyer:

Yeah, that's the big challenge. From a focus perspective it's the shiny objects keep creeping in and it's just keep batting them away and it's hard to do, and I think everybody faces that in different aspects. One of the things I want to talk about as your role as managing partner, tell me about your high value activities where you kind of live from the managing partner side.

John Hollan:

The role that I have taken on the last several years has really been the litigator of the highest value cases. The media, some of the marketing things that I've gotten involved in the last few years, I do those as Sam needs me to and has wanted me to help certain areas that we're growing in, but really my level of comfort, where I want to be, it's working cases. We have some really good young attorneys. I'm still pretty young myself, so I think people kind of look at me crazy when I say young attorney, but I've really enjoyed the last couple of years working with our younger attorneys on the best cases that they have, and I think that they're starting to realize more that if we do things the right way, that rather than what might be a 2 to a $300,000 case, we're turning those routinely into 700 to million dollar cases.

Same exact case, we're not really doing a lot different. A lot of it's just building the confidence in these young guys, and we have a team right now that I tell Sam every day from the, I don't want to say back of the bench, but from the youngest person in our firm to the most senior person in our firm, I'm really confident right now that anyone we have can go and get a million-dollar result on a case. They're proving that month in, month out.

Chris Dreyer:

And you teed me up there. So leaning into that, your reputation as the youngest attorney in Kentucky to secure a seven-figure verdict is pretty wild, so maybe just tell me that story about that case, what happened there. I think our audience would love to hear it.

John Hollan:

Yeah, that one was really fun and it came at an interesting time. We went into a trial about four or five months after I'd been into the firm we had a jury trial and I was in love. I mean, it was like a drug to me. I knew then and there I was like, "This is what I'm going to spend my life doing." But that was a good outcome. Then the next five years, I think my first trial was one or two months after graduating law school. We lost that case, very hard case, we lost, went to the Court of Appeals, got reversed and ended up getting a nice result on it. But it was three or four years. I mean, we had lost four or five cases and I just was really questioning the amount of money we're putting into this am I in the right field? Can Sam trust me to go and do this? Am I letting our attorneys, our staff, our clients down?

But then things kind of turned around and then came Mr. Walston's case. So it was actually a police pursuit case, Bullitt County, Kentucky, which is a very rural area. That would've been 2019, May of 2019. Sam, he's always been really cutting edge, so we used a lot of video footage in that case, we weren't really stagnant as far as the way we presented our evidence, and even though it was a conservative venue, the officer involved in that case had actually ran for sheriff. We were there at the courthouse and he knew everyone. He knew from the moment we walked in to the moment we walked out every day this defendant knew everybody, so it didn't necessarily feel great, but we got a 1.2 million verdict on that case. And for me with that trial and then the wins that we had gotten just before, and then since we got thereafter, it's really been pretty life-changing as far as just how I view trials and really the opportunities it's given us in our practice.

Chris Dreyer:

Thank you for the transparency too. I don't think many people want to talk about the licks, the early challenges and how you overcome them, the grit, the perseverance to continue and now become a top trial attorney and have a great litigating practice. I kind of wanted to lean into these Amazon delivery and FedEx ground contractor accidents. How did you get into space of specific Amazon delivery, FedEx type cases? How are they different from say an 18-wheeler case?

John Hollan:

It's not something I set out to do. I didn't just wake up one morning and think, "Oh, I want my cases to be against Amazon or FedEx." We just had a few cases come in, really, really catastrophic. One came in and it would've been, let's see, just before Christmas of 2016, and Chris, that's the one that really did it for me.

I grew up in eastern Kentucky, kind of in the coal mine area of hazard, this crash had happened in Rock Castle, Kentucky where Interstate 75 goes through Kentucky, which is unfortunately one of the roads that so many of our bad crashes have happened on, and one gentleman was killed, the other was horrifically injured, stopped traffic, a FedEx truck with two trailers plowed into stop traffic at 80 miles an hour. So obviously it was a miracle that our client lived. At the time I would've been, I guess probably 28, 29, I'd just gotten engaged. Life was really rapidly changing for me, and that case just took us to a different level of law. Sam was beyond obsessed with the FedEx model. We had at one point on that case, I was at a hearing in eastern Kentucky and there were lawyers from Knoxville, Memphis, Pittsburgh, and Louisville, and it's me and one other lawyer there. So it's literally the proverbial David versus Goliath.

So handling those cases, I got to see not only the resources that very powerful defendants are willing to put to fight against a single claim or a family that's been hurt really badly. But I also got to learn for the first time about the specific designs that companies like FedEx or Amazon have as far as shielding themselves from liability and just a different style and speed of litigation than I'd ever encountered in my life. I realized quickly, Sam and I both, that if you're going to take these cases, if you're going to win these cases, you're up against a different caliber of lawyer and you've got to kind of bring out a different beast in yourself if you're going to go and beat those companies in high stakes litigation.

Chris Dreyer:

And I can tell just from our conversation, just in this short time, it seems like you kind of knew what was happening, right? You just got engaged, you kind of have this picture in your head. So it speaks to the obsession over the case and handling it and making sure it's covered. So does that mean more expert witnesses? Does that mean more mock trials? What goes into the preparation for a big case like this?

John Hollan:

I can close my eyes and I feel like I'm back there again as part of that case and different moments in that case, but it really was all the above. There were medical experts on the case, we had a doctor from Harvard Medical School, there was a trucking practices expert, I believe, from Montana, there was an expert in Florida. I was trying to add it up recently, someone had asked me about that case. I think between Sam and I, we went to pretty close to 10 different states while that case was pending, thousands upon thousands of pages of documents. And if someone would've asked me at the beginning if we could handle that, if our firm could handle that with our resources, I would've said, "I don't know. It seems crazy to me. I don't know if I have those skills or if we have that kind of organization." But now looking back, it was life changing, it was career defining.

 And the attorney from Pittsburgh, who was the top dog, he was the lead counsel, he just said, "Man, our client wants to talk about this. We can't keep at this, the pace you guys are going. Wow." So they were starting to wave the white flag, and then I was actually, as fate would have it, my and I were married on New Year's Eve 2017, the first or second day of our honeymoon in Buenos Aires the case settled. So this was pretty cool.

Chris Dreyer:

That's incredible. What a moment in time.

John Hollan:

Yeah, it was cool.

Chris Dreyer:

When I had Sam on, we talked about your guys' structure for a case management where you use a team of three people per case: a lawyer, case manager, a legal assistant. How does this method of case handling take away any stigma associated with being an advertising firm?

John Hollan:

That's kind of a hard question for me because it's all I've ever known. I think it's the right way, I think it's the only way because clients get a dedicated point of contact. Mine's even a little bit different, Chris, because my case manager is my brother and my assistant is my soon to be brother-in-law.

Chris Dreyer:

That's awesome.

John Hollan:

So it very is much a family affair. A lot of times when I get cases, other law firms have had them, and it might be several other law firms, or it might be a client that has had prior experiences with other law firms. And the thing that they tell me the most is the level of communication that they get from our office. It's not calling into a switchboard. If I want to talk to John, I get to talk to John. If I need to talk to Josh, that's my brother, the case manager, I hear from him every other week on the dot. I don't have to worry about where things stand with my case. If anything, we might have clients that say, "Hey, can we maybe do every three to four weeks, every another one to two weeks?" And Sam has been so big as far as running our firm from a customer service perspective, we really are client first.

I was a referee for years. I thought I wanted to do that before I became an attorney. So really managing people. My grandpa used to tell me that we're all in the people business. I don't care how big you get or what you want to be, you're in the people business. So never forget that. And it's just so true. So I think that having that dedicated pod to each team and each case, I just think that's the biggest advantage that we get in it.

Chris Dreyer:

Yeah. Let me ask some follow up questions on that. I would like to hear your thought process on this is the caseload, right? And I'm asking this because we have the same situation from an agency perspective, it's like, well, how many account managers per client? And I'm like, "Well, some firms are bigger, some are smaller, and et cetera." So it kind of ebbs and flows. But on your side, I mean, you're handling these large cases, so do you have a much smaller caseload? And then talk to me about the structure and utilization and how you think about caseload.

John Hollan:

I maybe work on only a handful of cases. I'm getting in and I'm doing the things that I've got to have hours to do, and that's what leads to the really, really big outlier results. So my level of comfort has really changed a lot over the years. I think the highest I was ever at was just under 150 maybe. That was more pre-litigation insurance claim driven versus litigation, and it was just way too many. I could manage it, it's doable. But I think the work-life balance at that point, and some of the joy that I got from it, at least it was a little rocky at times. And some attorneys live very comfortably with no desire to litigate. And really in a volume shop, I think you have to have the different skill sets and the attorney's willing to take cases really whatever direction they need to go. And just having different teams with different focuses really goes a long way in our office.

Chris Dreyer:

Love every bit of that. I was just wondering if you could just share briefly just a couple other... I'm just interested in this structure. I think it's excellent, I love the overall thought process of it. Maybe just the duties of the case manager, the legal assistant, just overall how you're a pod, you work cohesively, I'm sure you meet on an ongoing basis, but how do you chop up the main duties between each of the roles?

John Hollan:

As much as we like uniformity, that does differ some from team to team. Myself, I'm not much of a micromanager. I'm really big on trust. Whether it's my own team or if I'm co-counseling a case, I pretty much have to have full trust in the team I'm working with. So we work off of Litify, and one of the things we've always been big on our office is case planning, and that is the we're going to have Litify or whatever software we're using at the time, we're going to have the checklist and the sort of built-in case management task that trigger based on the type of case and the caliber of case that it's.

 But now we have a case plan task item. So what that is if you're the managing attorney on a file, before your team can really even work on that case, you have to manually go in, complete an initial audit of the case, give basically a general overview of the case, and then give specific task items for the different members of your team, if it's a trucking case, if it's an auto case, if it's a premises case. That initial investigation is really going to be a lot different. So that's one of the biggest things, and I think we're seeing a lot of huge benefit from it, not only on some of the results that we're getting, but also just the speed with which we're getting some of those results.

It's the frequency in which our office gets auto cases settled within 30 to 60 days. It's unlike anything I've ever seen. Our time on desk has always been far less than anyone that I've ever looked at in the industry, and a lot of that is just built on, I think, our pod method with our teams, the initial case planning and workup, and really just the trust amongst the teams of A plus B, their job done, C is going to be really good. It goes a long way. It's the kind of diagnosis, the planning component, so you can dial in and before you start executing wildly and throwing paint against the wall, it's like, "Here's the plan. Let's execute on it. Has these similarities to these other cases that we worked on. So I think that's incredible.

Chris Dreyer:

John, this has been awesome. This has been a lot of fun. One final question. Where can people go to connect with you and learn more?

John Hollan:

Semijustice, as far as our trucking practice and a lot of the things that do for our trucking work, there's going to be a lot on, happy to give out my email, it's JHollan@kylawoffice.com. I have a three-year-old at home, so I'm not as active as I once was on some of the travel circuits, but I still like to do, at least in a good year, three to four of the national conferences each year and really love connecting, and I'm kind of a nerd for all these things. So if anyone ever has questions or they want to learn more about me or our practice, feel free to reach out.

Chris Dreyer:

That's it for this episode of Personal Injury Mastermind. If you've got value today, do me a favor, subscribe, leave a review, and share it with someone who wants to dominate their market. I'm Chris Dreyer. See you next time.

 

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