Mastering the Modern Courtroom: Innovation, Empathy, and Personal Injury Success with Bob Simon

[00:01:00] Chapter 1: Introductions

Jack Newton: Bob, thanks for joining me this morning. We’re here at Rogers Arena watching one of the morning skates for the Canucks. It’s great to have you here. How cool is this?

Bob: This is pretty awesome. You know, I always wanted to be on a show in a hockey arena, so this is like checking a box.

Jack Newton: So maybe just to start off, I know you’ve got a really interesting partnership with the LA Kings. We at Clio are really excited to partner with the Canucks and become their first-ever away jersey sponsor for this season. The response to that has been incredible; frankly, I’ve been surprised by how positive and how noticed that sponsorship has been. But I know you’ve been seeing a lot of success with your LA Kings partnership as well. I’d love to hear a bit more about that.

Bob: Yeah, so when the opportunity was presented to us—you know, the Kings live a lot in our neighborhood where we live in Manhattan Beach. It’s like a community franchise for us. They have a real culture fit with the people there. So we were like, “Yeah, why not?”. We go to a lot of the games and know the folks. We don’t do a lot of direct-to-consumer marketing, so that wasn’t the play. It was more just: “Let’s do something fun because we’re doing it anyway.”.

Then we started thinking, “Well, what else could we do that’s fun?”. We have a large social media engagement. So we asked, “What if the Kings could repost some of the funny stuff that we do?”. And they were like, “Okay, we’ll do that.”. I was like, “Oh, really? Well…”. So we just try to do a lot of fun. Like, my brother and I are behind the penalty box with missing teeth, and that gets a lot of attention. We like to have some weird brand awareness.

Jack Newton: And that’s got a lot of traction.

Bob: It does; that plays right.

Jack Newton: That’s great. Well, we’re looking forward to watching the Kings and the Canucks play tonight. We’ll be taking both of our respective teams out to a box here, and I’m looking forward to soaking that up.

[00:04:22] Chapter 2: High-performing teams and ego-less leadership

Jack Newton: Maybe we can talk for a minute about team dynamics. In a great hockey team, you see it every day: it’s about the right ingredients, the right team, and the right set of skills coming together to win a game. What’s that look like in a law firm?. Talk to me about how you’ve built a high-performing team.

Bob: Chemistry is extremely important, and you have to have a team that works together. We do everything in teams at our law firm. We have probably 30 lawyers. That started with just me, but that’s where we are. We try a lot of cases. For example, two of our trial lawyers are on a case right now; they work very well together and have a virtual support team that enables them.

Building a team is not easy, but it takes leadership from top to bottom. You have to have the ability to know everybody in your company. I know it’s hard once you get past the 100-person mark, but you should still celebrate the little wins and call people out for doing something well. People find a lot of value in personal recognition.

And then, it’s about inspiring and letting other people be leaders. One thing we’ve done better than other firms—where you have that name law partner who is the main trial lawyer—is letting the ego go. Often, those partners feel they have to be standing in front of every photo or trying every big case. I had a different mindset. I wanted to recruit really good folks and then empower them. That’s why we rebranded from my firm name to just “Justice Team,” because I wanted other people to have the ability to take center stage.

We’ve had some very talented lawyers go and start their own firms, which we actually encourage. People always say, “I can’t believe so-and-so left,” and I tell them, “Well, I encouraged them to leave.”.

Jack Newton: Right, because at a certain point, you’re giving them a platform to grow. It’s something we talk about at Clio a lot: we want to prepare you for the next chapter of your career, whether that’s at Clio or the next place. You’re going to grow while you’re here, and we’re going to give you the tools to thrive over the long term.

Bob: Exactly. We still work on cases together with many lawyers who left our firm, and we still collaborate. We see each other all the time; it’s a pretty small community in consumer injury trial cases. But you have to come from a good place. People know if you’re inauthentic in leadership. I’ve seen leaders who were just non-existent during times of tragedy or hard times—COVID is a perfect example. A lot of leaders didn’t reach out and check on their team. That’s when they need you most. Just checking in—sending a text message or a Slack—goes a long way.

[00:09:06] Chapter 3: The human-first hiring filter

Jack Newton: Tell me about your growth journey. Your approach to teamwork and building your firm has been pretty incredible, and I would love to hear the trajectory of the firm.

Bob: It started with just me wearing every single hat. You know the startup journey—it’s the same as a law firm. I was doing everything from the mailroom to writing my own letters and filing. Half my day was just scanning in mail, putting it into folders, and creating action items. This was 2009 or 2010. Then, I got so busy bringing in cases that I brought in my twin brother to form our partnership. From there, we just grew naturally.

When we hire, we go with a “human-first” approach. I hardly look at a resume. I don’t care where you went to school or who your parents were. If you can connect to human beings and you want to work, there’s a place for you. Some of our best lawyers went to unaccredited law schools, but they are among the best I know. We hire talent and give them the tools they need to thrive. Some people stay for life, some leave. But would you rather invest in someone and have them leave, or not invest and have them stay?.

Jack Newton: Yeah, right.

Bob: Other firm owners ask why I promote my other lawyers if they’re just going to leave. But other people notice that you’re supporting people other than just yourself. You’re giving them a launching pad. We had a town hall the other day for fire victims, and someone asked my thoughts on two other firms they were considering. I told them, “Look, they’re great. If they weren’t, I’d tell you.”. I knew those firms would give them great representation. When you hire a lawyer, you’re hiring a partner and a confidant. You have to have someone you connect with. There are bad lawyers out there, but they usually concentrate on only one thing: money.

Jack Newton: Right. Tell me more about that filter. You talk about being human-first. How do you get hiring right? What attributes are you looking for?.

Bob: Because we’re known for cultivating young people out of law school and giving them opportunities to try cases, a lot of people reach out to us. We couldn’t hire everybody, which is why we started “Justice HQ”—to show them how to start their own firms and grow.

Mentorship is the biggest thing people need. Whenever someone comes through the door, I get a good pulse check on whether they’re a good human being. They go through interviews with our team, and the number one thing my partners and I discuss is: “Are they a culture fit?”.

[00:12:19] Chapter 4: Scaling excellence through systems

Jack Newton: Is that “culture fit” a feeling, or are there quantitative value-oriented questions you ask?.

Bob: You can get a really good feeling from people’s social media. We usually have that stuff pulled before the interview. I also know almost everyone in the industry, so I can ask around. Then it comes down to asking, “What excites you about being here?”. We want to know their story and what inspires them. We want to weed out people who are just there because you can make a lot of money. If they have passion and fit the culture, you can teach them the other stuff.

Jack Newton: You also take a holistic approach to building this incubator. You’ve got co-working spaces and a deliberate investment in in-person connectivity. Walk through your thinking there.

Bob: I always thought: “Why are law firms so expensive? Why are they such a barrier for consumers?”. We work on contingency, but I see other firms charging clients for crazy things. I also think lawyers shouldn’t be billing by the hour as much anymore; it should be more flat fees with the help of AI.

Law schools don’t teach you the business acumen or how to actually run a firm. So I created something that is like a high-level professional organization meets a tech incubator. It offers on-demand mentorship and access to specialists. Even vendors like Clio are on the platform for weekly stand-ups. I wanted lawyers to choose their own adventure. For too long, the “old guard” decided who got speaking spots or who wrote the articles. We wanted to change that. If you maximize operations, you can help thousands of clients at a time.

[00:19:57] Chapter 5: Operational mastery and the “Great Lawyer” trap

Jack Newton: What do you think the single biggest missing skill set is for young lawyers to be successful?.

Bob: Their “house” is not in order. They don’t have a good operating system and they aren’t forward-thinking. You can’t just “do your work.”. You need a case management system, a marketing plan, and a growth strategy. If you want to be the lawyer in the courtroom, you need a plan to have an operator do the other things so you can do what you’re passionate about. Too often, great lawyers fail because they try to do everything themselves. If nobody can find you, or if you don’t get back to clients because you aren’t organized, what good is being a “great lawyer”?.

Jack Newton: How do you set up the system for sustainability?.

Bob: When you set it up, it has to be the infrastructure for growth. Lawyers ask me where to start—do they need SEO?. I tell them: unless you’re spending $10,000 to $20,000 a month on SEO, it’s not worth it. Start with a simple website for credibility. Then, make sure your chat bot or form fills directly into your CRM—we use Clio Grow for that. That is your bedrock.

Every contact is a cross-marketing opportunity. People are shocked at how many cases I get from social media using just a cell phone, while other lawyers spend tens of millions on traditional advertising. If you create good content and gain credibility, people will hire you.

Jack Newton: Maybe demystify “operations” for us.

Bob: Operations is the rock bed of every business. You need an operator who optimizes every system and makes sure your people are actually using them. We spend a lot on technology and AI because it makes us more efficient. Since we’re on contingency, we don’t bill for time; we have to be efficient.

I also think it’s better to find an operator who is not in the legal space. A law firm is a business, and many people don’t treat it like one. When outsiders look at law firm systems, they usually think they’re “whack.”. The managing partner shouldn’t necessarily be the operator. Law schools should require classes on operating systems and how to run a client trust account. Without that training, lawyers make a lot of “unforced errors.”.

[00:25:04] Chapter 6: AI, VR, and the high-tech courtroom

Jack Newton: Walk through your technology stack.

Bob: Think of a problem you need solved, then find the product. The mailroom was a big pain point. We use Foundation AI; they are essentially our mailroom. They put things in folders and handle naming conventions, though we still have humans check for accuracy. The next evolution is getting intelligence off those documents through Clio Duo.

We also use Attorney Share for referrals. If a case isn’t our specialty, we push it to a specialist and track the co-counsel fee. I can literally see new cases popping up on my Apple Watch. That didn’t exist when I started.

Jack Newton: You also had an interesting post about using VR in the courtroom.

Bob: A few years ago, I was trying a product defect case against a large auto manufacturer. They had an unlimited checkbook and tried to bring in a VR set for the jury to replicate the terrain. We got it excluded because there’s too much uncertainty—all jurors have to see the same thing at the same time.

However, virtual trials are happening. Imagine everyone on a big Zoom—the judge, witness, jurors, and lawyers. A friend recently got a verdict over $100 million in an all-virtual trial. You have to be on top of technology because jurors appreciate efficiency. I always ask jurors: “Would you hold it against us if we get through this quickly to get you home to your families?”. They always thank us for being efficient.

[00:33:18] Chapter 7: Credibility and the adversarial myth

Jack Newton: Let’s talk about being effective in the courtroom. How do you build trust with a jury?.

Bob: I tell them: “Credibility is not given; it’s earned.”. In my opening statement, I say: “If by the end of this case you think this is a bunch of BS, you can give my client zero. But the same holds true for the other side.”. Then in closing, I show them exactly how we proved everything we said we would.

Jack Newton: How about with opposing counsel?.

Bob: I have a “work together” mentality. The most stressful trials are when the lawyers hate each other and everything is a fight. Sometimes the law firm is the barrier to resolution. I’ve seen lawyers fight over things as simple as the speed limit. The jury hates it.

If you get along with opposing counsel, you can stipulate to facts and speed up the trial. I try to de-escalate. I’ll send an email that’s just like: “Hey dudes, what’s up?”. I’ll look them up and mention their kids or a soccer game. It takes the guard off. We get so many referrals from counsel on the other side because we settle cases faster by having honest conversations.

[00:36:51] Chapter 8: The work-life blend

Jack Newton: You strike a great work-life balance. Talk me through how you’ve developed that.

Bob: You have to be very deliberate. I take my kids to school and pick them up. I keep a visual calendar on a whiteboard showing four months at a time. My fixed meetings don’t start until 9:15 AM. I try to be home on weekends. I alternate between “hard travel” months and family months.

I view it as a work-life “blend.”. I’m always on call, but I can check my phone for five minutes, decide if it’s urgent, and then get back to family time. I block off my time. I even try to turn conferences into family getaways. You have to learn how to say “no” to things that don’t fit the calendar.

[00:43:48] Chapter 9: Content, community, and authenticity

Jack Newton: Let’s talk about your social media. You drive huge results without a massive budget.

Bob: I focus on pillars: work-life balance, technology, activism, and, of course, bourbon. It’s easy to create content when you actually like these things. People are getting more sophisticated; they want to know your story and be attached to a human brand.

If someone searches for “injury lawyer,” they’ll just go to the next person on Google. But if they search for a specific name, they won’t call anyone else. You have to be a little shameless with it. Most lawyers have a cell phone and can put out content for free. During the fire cases, I put out practical “how-to” videos on supplies and housing. That got more traction than lawyers spending millions on ads.

[00:47:43] Chapter 10: Future disruptions and parting advice

Jack Newton: What is the next big disruption?.

Bob: AI voice recognition for intake. Imagine AI picking up the phone and qualifying cases. It weeds out the “FBI microchipped me” calls. Our latest Legal Trends Report found that half of phone calls to law firms go unanswered. This technology provides access to justice by at least giving people an answer or a referral.

Jack Newton: What’s one simple change a lawyer can make to be more client-centric?.

Bob: Put up a photograph of the client’s family or their house in the digital file. It grounds you in why you’re doing this.

Jack Newton: One piece of advice for a new P.I. lawyer?.

Bob: Reach out for mentorship. Slide into people’s DMs. If someone pings me on LinkedIn and asks for five minutes, I usually give them my cell.

Jack Newton: And for parents?.

Bob: Educate your kids on what you do so they understand why you have to go. After 5:00 PM, it’s family time. Be present in the moment.

Jack Newton: Thanks for joining me, Bob. Looking forward to the game tonight.

Bob: Go Kings Go!.