Allyson Ostrowski:

To truly tell somebody else’s story, you have to be a good listener, put your ego aside and when problems come up, because they will, every case has problems, that’s why they go to trial, you have to be able to say, “So what? Now what?”

Chris Dreyer:

By building genuine relationships, you organically expand your network and bolster your reputation.

Allyson Ostrowski:

Business development is just being a better friend to people. Just making sure that you’re in people’s lives and they know that you’re there if you need them.

Chris Dreyer:

Welcome to Personal Injury Mastermind. I’m your host, Chris Dreyer, founder and CEO of Rankings.io, the no excuses, no BS legal marketing agency that works harder than the competition. Each week you get insights and wisdom from some of the best in the industry. Hit that follow button so that you never miss an episode. All right, let’s dive in. Changing career paths is daunting. The uncertainty is enough to keep many of us stuck, but with courage and strategic relationship building reinvention is possible. Just ask Allyson Ostrowski. After 15 years as an LA County District Attorney, she made a bold shift.

At 40 years old, mid-career, she dove into civil law focusing on catastrophic personal injury cases. The transition was daunting and it presented a learning curve. Criminal cases come to you, but in personal injury, you have to hustle to get clients. Allyson tapped connections from her past to generate referrals and discovered a marketing strategy that felt genuine. She proves that with hustle and relationship capital, anything is possible. If you’re thinking of making a major shift, this episode is for you. Today, Allyson offers her candid advice on how to make a big change and feel good about it. Here’s Allyson Ostrowski, trial attorney at acts.

Allyson Ostrowski:

I grew up in Los Angeles and growing up here, I wasn’t interested in law at all. I was interested in the entertainment industry because that’s what was here. And so I went off to college. I went to Boston College, and while I was there, I was a communications major and a sociology major, and I was just headed down that path to publicity and entertainment. And then I had a professor who literally changed my life, Dale Herbeck, he’s amazing. And he brought me in one day and he said, “Hey, what are you going to do when you graduate?” And I said, “Oh, I’m from LA. I already have a job lined up in publicity. That’s what I’m going to be doing.” And he just looked at me and shook his head and said, “No, that’s dumb. You shouldn’t do that. You should go to law school.” And I thought, “Oh, no, I’m not one of the smart kids.

I can’t go to law school.” That’s not how I view myself. And he said, “Well, I’m your advisor and I’m looking at your grades and you actually, you have really good grades. You really should go to law school. So I think next year you should write a scholar of the college thesis with me, and that’ll be like a law review and that’ll help get you into law school and then you’ll be off and running.” And that felt very intimidating, but I’m glad I took the jump and did it. And I did end up in law school, which that first year was a blur as it is for most people I think. And just that summer, I took whatever job I could get. My family was not a family of lawyers. We didn’t have any connections or know anybody. And I got this one job at a family law firm.

And so I was thinking, “Okay, I guess I’m going to do family law.” My second year of law school, I found the trial team. And that was really like, “Oh, okay. I found my people. I found my thing.” My husband likes to joke that I’m really just a frustrated theatre major and frustrated actress. So delivering the closing argument was helpful and kind of scratched that itch for me. Once I found trial team, I thought, “Oh, this is what I need to do. I need to be a trial lawyer.” But family law doesn’t have a jury trial system. They’re recorded equity. So when I graduated from law school, I just took the job I could get, which wasn’t family law. The DA’s office wasn’t hiring. It didn’t even occur to me to be a civil litigator. I didn’t even know what that was really. And so I just took the job I could get, which was family law, and I really did love it.

I was helping people with their human problems and their human lives. I never wanted to be the kind of lawyer that looked at contracts and documents and dealt with taxes and things like that. I just wanted real life human experiences. So I did that for a couple years and seemingly enjoyed it. I was fine. I was happy. I was working a lot, but I was enjoying it. And then the DA’s office opened up in 2005 and I thought, “Oh, well, I’ll regret it my whole life if I don’t at least try to throw my hat in that ring, I think I would love to be in front of a jury and that’s maybe what I’d be good at.” And so I applied and Steve Cooley hired me, but he hired me at a time when I was actually in a bench trial for a client who was fighting for custody of her child that she believed was being sexually abused by the father.

And I felt like I couldn’t abandon her in the middle of that trial. And so I actually turned the DA’s office down initially. In the course of that trial, the opposing counsel ended up having an improper communication with our judge and a mistrial was declared. That trial went away and suddenly I was free to join the DA’s office. So I called Mr. Cooley back and said, “Hey, any chance I can still come be a district attorney?” And he said, “Yes.” And so I went off to do that. And a year later, my family law mentor and boss, who I still am close with to this day, and I really adore, she said, “You’ve got to come back. I’ll double your salary at the DA’s office. You got to come back. We miss you.” And I didn’t even have to think twice. I mean, I was just trying DUIs and misdemeanor domestic violence. I’ve been doing prelims. I wasn’t even doing any of the stuff I would later go on to do, but I knew that it was just where I was happiest and felt like a calling.

Chris Dreyer:

Amazing. And what an amazing human to tell you, “Hey, I see this in you. You should consider this opportunity.” And wow, what a guide. That’s incredible. So in law school, you won Best Advocate and the National Institute of Trial Advocacy Tournament of Champions. So you didn’t just jump in like these are my people are the words that you said. Tell me a little bit about that experience.

Allyson Ostrowski:

That experience was fun. That was a competition that we were able to go to because we had performed well the year before. The trial team just sort of became my life in law school. I mean, I really paid very little attention in class. I was mostly working on my direct exams and my closing arguments and my crosses, and I just lived and breathed trial team. And it was a civil case, it was a negligence case, it was a slip and fall that we were going to. And I remember when I won that competition, I was proud and happy and excited in law school. And then when I applied to the DA’s office, you have to go through three interviews. And the second interview, the person interviewing me said, “Hey, you haven’t really talked about how you won this Tournament of Champions national competition.” And I just looked at him and I said, “Yeah, it’s not like I won a million dollar jury verdict.”

To me, it was just not an impressive thing because it was in law school. And he just looked at me and shook his head and said, “No, when you get in front of Mr. Cooley, you need to make sure that you talk about that.” And so I did. But it really what it made me aware of just as how much I think, and I think women do this especially, we downplay our successes and we think they aren’t a big deal. And really I was sort of diminishing the importance of that immediately in an interview, which is the exact wrong thing to do.

Chris Dreyer:

While you’re a deputy district attorney, you tried nearly 60 cases and had a 98% success rate. Very impressive. If you had to distil your success to kind of a few key factors, what made you such a strong trial attorney?

Allyson Ostrowski:

Nobody’s more prepared than I am when I walk into court. I mean, I may not be the smartest one in the room. I may not have all the facts on my side. I may not have the law on my side necessarily. There’s always going to be challenges in every case, but I will know my case inside and out and I will have left no stone unturned. And I took a lot of pride in not just giving victims of crime a voice, but giving a criminal defendant a fair trial and holding the police accountable. I really saw my role in that job as globally, much more global, much more about all the pieces of the criminal justice system and not just me getting to win. And so I always believed what I got up and said, I never had to get up and argue something that I didn’t think was true.

If I didn’t think the defendant was guilty beyond a reasonable doubt, then I shouldn’t be prosecuting him. And so I really took that job seriously and my ethical obligations seriously. I feel very grateful to be at a place like I am now at Acts Law where now I’m in civil and I’m still helping people who have been hurt through no fault of their own, which is sort of my north star, but I believe in my clients. I get to take cases that I feel strongly about and I feel passionate about. And so getting to advocate for somebody who’s been hurt through a car accident as opposed to an assault or a sexual assault in the civil arena feels just as satisfying.

Chris Dreyer:

Your preparation and these experiences of the national competition. And then your 60 tried 60 cases to very high success rate when you switch over to PI, was there a big transition or what was that transition like? A large proportion of our audience is PI. There are many criminal attorneys listening to that are considering like, “Oh, maybe try plaintiff and-”

Allyson Ostrowski:

And a lot of PI does criminal defense sometimes too. There’s those hybrid firms. Switching careers in your forties is very humbling. I will not lie. I left the DA’s office after 15 years, done all the things in that office, and I could try a gang murder or a rape case in my sleep. I’d done them a million times and I was assigned to courthouses where I was seeing the same judges and the same opposing counsel. And I had built a reputation and to come into civil, an entirely new arena, it wasn’t so much hard to learn the law. I mean, I went to law school. I’ve been a lawyer for 20 years. I can figure out the law, but to have to walk in without my reputation and without the people I know and having to learn a whole new language, that was very intimidating and very challenging. But I have to say, getting up and doing closing argument, I was in my happy place once again in a civil case, that’s where I’m happiest.

Chris Dreyer:

Do you find the tonality and the delivery to the jury changes because of the type of cases?

Allyson Ostrowski:

When criminal, it’s very black and white. You’re here to decide did a crime happen and is this the guy that did it? We’re not there to decide whether he’s a good or bad person or has family who loves him. It’s a very Stoic approach and very sterile, very sterile. He either did or he didn’t. And you really aren’t allowed to appeal to the human aspect for that victim of crime and what they went through, none of that is really allowed in criminal. And in civil you’re talking about people who the defendants are oftentimes not a bad guy. They’re someone who got in a car accident, their insurance company’s the one not paying you. I’m sure they’d love for their insurance company to pay you.

So the defendant themself is not often the person that you’re painting as the villain in this story, and the jury’s not going to view them as that. And so when you’re talking about negligence, you’re really talking about the impact that somebody else’s negligence had on your client’s world, on their health, on their family, on their income. And so I think you actually get in civil a better chance at talking about all those human factors, even though civil’s about money and criminals about freedom, I’ve found that you end up talking much more about the human aspect and the implications of that in civil cases.

Chris Dreyer:

Being a great trial attorney from a business development standpoint, you got to market and advertise from some degree. I know very binary it’s pre led a lot of times, do a lot of the billboards and TV, and then a lot of times the trial attorneys get a lot more referrals from the reputation and doing outstanding work. What have you seen from a business development standpoint, from you being a phenomenal trial attorney? Is it lending itself to these opportunities for more referrals and how does that play into business development?

Allyson Ostrowski:

Yeah, the business development piece was the most awkward piece for me coming over from criminal because you don’t have to do that there. There’s plenty of business and cases are coming, and in civil, it just felt very weird to be on TikTok or be on Instagram and be bragging or putting myself out there. It felt very inauthentic for me and I didn’t like it. And what I’ve learned is that, and this is through the help of a business coach who I really enjoyed working with named Jennifer Forrester. What she really taught me is business development is just being a better friend to people. Just making sure that you’re in people’s lives and they know that you’re there if you need them. So I’ve been really lucky, and I’ve had a lot of referrals from my former life, like police officers and DA’s will often reach out to me with a case where, for example, say it’s elder abuse.

So there’s a criminal case there that’s being prosecuted in criminal court, but that facility where the elder abuse took place had an insurance policy, and I was able to get that victim’s family that policy. And so while the wheels of justice will turn much more slowly in criminal in terms of getting that case off the ground into trial and whether there’s a conviction, in the meantime, I was able to get them some civil justice and that felt really good. So I think my former colleagues and people that were in my life before know that I’m going to work hard. I’m going to do everything I can and leave no stone unturned. And just staying in touch with them, just checking on them and seeing how they’re doing and reminding them that I’m here, that in and of itself has been great business development for me, and it doesn’t feel yucky, right? I don’t have to go brag about myself or anything. I can just make sure my friends know I’m there for them.

Chris Dreyer:

Fantastic. Fantastic. And you mentioned Jennifer Forrester and you did this post along the lines of loneliness in the legal profession, how to create authentic connections and how to create boundaries to prioritize your mental health. In what unexpected ways does loneliness show up in the legal profession?

Allyson Ostrowski:

Yeah, I think that quote, that’s actually Jennifer’s quote I think that I reposted, so I got to give her credit. But one of the things that she was posting about in talking about is I think especially for solo attorneys, I mean, I’m not a solo attorney. I’m at a great big firm and they’re wonderful and we’re a family here, and so I can work from home, but I can also come into the office and see a bunch of people, and I don’t have to get lonely. I’m able to combat that. But I know for my colleagues who are solos, that’s hard. You miss your community.

You want to spitball off of your colleagues. And that’s one of my favorite things about being a lawyer frankly, is talking about cases and strategizing and oh my God, listen to what this judge did, and can you believe they said that? And those are the fun moments for me. So I think it’s really important that even if you’re a solo or at a big firm, there’s so much work, it’s so easy to just put your head in the sand and grind down and do your stuff and go home and have a drink and go to bed. So I think you have to make a concerted effort to be engaged with your colleagues.

Chris Dreyer:

We have a remote company, so I think of that because here I am, I’m in this office, I got a big office and I got my employees scattered around. I will say I’ve started learning the hard way to hire in pockets, like, “Hey, we’re going to hire so many St. Louis people. That way they can get together for lunch and-”

Allyson Ostrowski:

Smart. That’s really smart.

Chris Dreyer:

Yeah, it’s just a different approach for remote. So you also, from the criminal side to the PI side, I mean, one of the things that I think about is, geez, sometimes whether it’s the worst human beings on the criminal side or these people going through the worst times in their life, and sometimes I get this empathetic where I can understand and I feel them, and it’s really draining on me. How does that affect you?

Allyson Ostrowski:

Well, I think what you’re talking about is vicarious trauma, which when you’re an empathetic lawyer who caress about the people you’re representing or the cause that you’re fighting for, it’s very easy to vicariously sort of feel that trauma that they’ve been through to some degree. And so you do have to be careful. I mean, as a DA, I would often joke that I was dead inside. Thank God I was because someone had to do this job, but for whatever reason, I was just really able to compartmentalize work from home. I’m a mom, I have two little kids. When I came back from maternity leave, after having my little boy, I went straight into a case where a two-year-old little girl who was my other child I had at home, I had a case where a two-year-old little girl had been kidnapped and sexually assaulted, and you would’ve thought that that would’ve broke me right?

Way too close to home. I’ve got kids these ages and I’m coming out on maternity leave. And it was definitely a challenging case, but it was also so incredibly rewarding. And that fire and reward of helping people really for me was what I needed to keep that block of having the vicarious trauma. I knew it was much more important to get the job done, and so I was able to do that. But it’s hard. I mean, you care about your clients and you feel for them. You want to help them, and sometimes you’re going to and sometimes you’re not. That’s just sort of the reality of the world. And so I think when you can’t help somebody, it definitely hurts me in a way. It hurts me in a different way, for sure.

Chris Dreyer:

There’s a difference between coaches and mentors. A coach can show you from an accountability perspective, but a mentor has done this and you can tell you and kind of guide you much more quickly. If you were going to put on your mentor hat from all your experience being a phenomenal trial attorney, what would you tell these young attorneys that want to be excellent trial attorneys? What do they need to do to succeed?

Allyson Ostrowski:

I think to a good trial attorney, you have to be a good listener, and you actually really have to put your ego aside. And I think that’s hard for us trial lawyers, right? Anybody who’s able to get up and speak in front of a group of people clearly has a healthy ego. And I’m no exception. I’m sure I have my ego, but I think it’s really important as a trial lawyer to connect with your clients, to connect with the jury, to truly tell somebody else’s story. You have to be a good listener, put your ego aside and when problems come up, because they will, every case has problems, that’s why they go to trial.

You have to be able to say, “So what? Now what? Okay, that happened, that ruling occurred, and it really sucks for my client and my case. Now what do I do?” And I think the more prepared you are going into a case, it lets you deal with those fires as they pop up. And if you can deal with a fire, if you don’t have to prepare your direct examination for your client the next day, you knew that direct examination of your client was coming, that should be prepared way ahead of trial. And so it lets you be free to handle all those fires that come up in a trial, which they’re always going to happen.

Chris Dreyer:

I love that. I love that. One final question, Allyson, how can our audience get in touch with you?

Allyson Ostrowski:

So I work at Acts Law, so you can always go onto the actslaw.com website. You can find me on Instagram just by searching my name, Allyson Ostrowski. I’m ARO Law Corp. Yeah, I guess those are the two primary ways, and you can email me at aostrowski@actslaw.com. If you ever want to talk about a case or a round table, that’s my favorite thing. So feel free to pick up the phone or send me an email.

Chris Dreyer:

Thanks so much to Allyson for sharing your wisdom today. Let’s hit the takeaways time for the pinpoint. Study up, Allyson attributes her success rate to meticulous preparation and knowing every case inside and out, doing the legwork to uncover all details and anticipate challenge allows you to handle whatever comes your way.

Allyson Ostrowski:

Nobody’s more prepared than I am when I walk into court. I may not have all the facts on my side. I may not have the law on my side necessarily. There’s always going to be challenges in every case, but I will know my case inside and out, and I will have left no stone unturned.

Chris Dreyer:

Marketing should feel good. Authentic self-promotion is going to look different for each person. Social media may not be your thing. That’s cool. Allyson found success in shifting the way she thinks about marketing herself. She doesn’t sell who she is and the services she offers. Rather, she thinks of herself as a trusted and caring friend. She shows up with genuine concern. She listens deeply and tries to understand her client’s perspective.

Allyson Ostrowski:

Business development is just being a better friend to people. Just making sure that you’re in people’s lives and they know that you’re there if you need them.

Chris Dreyer:

Put your best foot forward. Careers follow winding paths. You never know when someone from your past will resurface in the future. And the key is to be a great referral. By consistently showing up as your best self, you build a reputation that sustains you for the long haul. Remember, every choice shapes your legacy.

Allyson Ostrowski:

I’ve had a lot of referrals from my former life, like police officers and DA’s will often reach out to me with a case where, for example, say it’s elder abuse. So there’s a criminal case there that’s being prosecuted in criminal court, but that facility where the elder abuse took place had an insurance policy, and I was able to get that victim’s family that policy.

Chris Dreyer:

For more information about Allyson, check out the show notes. While you’re there, please hit that follow button so that you never miss an episode of Personal Injury Mastermind with me, Chris Dreyer, founder and CEO of Rankings.io. All right everybody, thanks for hanging out. See you next time. I’m out.