Moving From Generational to Regenerative Wealth: A New
Paradigm in Family Planning

Ali Katz:
Hello, and welcome to the NewLaw podcast where we guide entrepreneurial lawyers to build law practices into businesses they love. I'm Ali Katz. In today's episode, we are talking to Jordan Ostroff about his inspiring journey from being a prosecutor to founding a successful personal injury law firm now run by his wife while he works with law firm owners on how to love their law firms. And just finished a book, "Love your law firm". You're going to hear how he's helping lawyers nationwide find professional success and personal fulfillment, and how he was able to take off close to a year to travel with his wife and child. So if you're at all feeling burned out or unsure about how to turn your legal practice into a fulfilling business, this episode is for you. Join us and listen to a great conversation. An inspiring conversation with me and Jordan. Let's get into it.

Ali Katz:
All right. Hey, Jordan.

Jordan Ostroff:
Hello.

Ali Katz:
Good to see you today. Thanks so much for joining me.

Jordan Ostroff:
Yeah, no problem. Happy to be here.

Ali Katz:
So you just wrote a book that is very near and dear to my heart, title wise. "Love your law firm" book. And it's near and dear to me, very specifically because I have talked for a long time about loving your law practice. And when I read your book, I thought, uh oh. I need to make sure that what Jordan's talking about is it aligned with what I'm talking about. And it did, and it was so spot on. So thanks for joining me here today to talk about that and your history of figuring out how to love your, your law firms.

Jordan Ostroff:
There we go. May everybody who listens to this or reads the book avoid many of the mistakes I made along the way. But, yes, we're here.

Ali Katz:
For sure. Before we start with that, though, as I was reviewing your story, it turns out that we went to the same college.

Jordan Ostroff:
No way.

Ali Katz:
Yeah.

Jordan Ostroff:
Wow.

Ali Katz:
Yeah. UCF knights. Go Knights.

Jordan Ostroff:
Yeah.

Ali Katz:
Yeah. I have a feeling I was there quite a few years before you, but what year did you graduate?

Jordan Ostroff:
'09.

Ali Katz:
Yes. I was there. You graduated college in '09?

Jordan Ostroff:
I graduated college in 2009.

Ali Katz:
Goodness, you're a youngin.

Jordan Ostroff:
Thank you. You know, this morning I found out I'm five years younger than Bandit from Bluey. So, you know the important things.

Ali Katz:
You have done a lot, and you have a lot of gray in your beard.

Jordan Ostroff:
It allows me to raise my hourly rate. The more gray it goes.

Ali Katz:
It's really. It's really. It's really true. So. Yeah. And you also grew up in South Florida? I also grew up in South Florida. And then you stayed in Orlando for law school. I did get out of Orlando. I got out of Florida altogether. And then you also your first real law job was for the state of Florida as an assistant state attorney, and I interned at the Florida attorney general's office.

Jordan Ostroff:
Oh, there you go.

Ali Katz:
So we've got some similarities there. And I did see, as well that you always knew that you wanted to be a lawyer, that there's home videos of you at 3 or 4 arguing with your parents. But how did you know you wanted to be a lawyer?

Jordan Ostroff:
I have no idea. You know, I joke with everybody, like, half the time, I don't know what lawyers do anyway. But I enjoy what I'm doing now, so I don't know, I was like, you know, I think the doctor, somebody might die in front of you. And knock on wood, no one's died in front of me as a lawyer yet, but hopefully forever. It's just. It's one of those things, like, you fall backwards into something that you enjoy.

Ali Katz:
But was it really just maybe hearing your parents, like, you're arguing with your parents and you're hearing them say, oh, he's gonna be a lawyer, or something like that? Did that happen?

Jordan Ostroff:
I'm sure it did. I don't recall my parents saying, I don't recall in the moment my parents having anything positive to say about my stubbornness. And now with a six year old, I know exactly what they went through. So, mom and dad, I am sorry, but, you know, karma has delivered me a mini me, so.

Ali Katz:
Yes. Well, isn't it wonderful? You get to revisit all of that as a parent? I think that's the best part of parenting. So you are a parent as well as being a lawyer, and you have built a law firm with your wife, Heather Trick Ostroff, "Driven Law", a PI law firm located in Orlando, Florida, which is where you are both still living. And it seems to me that you're really in the role of business owner. You're not a PI lawyer, Heather is.

Jordan Ostroff:
Yeah, I have. I've never handled a PI case. I have no idea how to handle a PI case. But I know who to go to. You know, they're. They're there. They're there. They're there, you know, and they can, uh.

Jordan Ostroff:
Yes, do their job amazingly well.

Ali Katz:
And so when you came out of law school, were you already married to Heather or in relationship with Heather and you two did this together right from the start?

Jordan Ostroff:
No, we met in court on opposite sides. She was a PD, and I was at the state. We did not have a case in common, so don't worry, there was no issues there. Although I would have lost whether I won or not. So, yeah.

Ali Katz:
That's juicy. So you were on opposite sides. You were at the state attorney's office. She was a public defender.

Jordan Ostroff:
Yep.

Ali Katz:
And you're both working for the government, and then you meet and decide to start a business together. Is that how it went?

Jordan Ostroff:
Uh, so when we first met, I was an intern and she was a PD, and then I came back as a real prosecutor with a bar card. So she got to the point where, like, all of her cases were serious, all of her clients were looking at life or, or close to it, you know, the whole thing. And so she was like, hey, I really enjoyed my time at juvenile court. I want to try to go teach civics to middle school kids and see if we can get them interested in the system in a way to avoid going through it later. And I was like, all right, well, if you're going to do that and take the pay cut but still have the insurance, this is probably a good time for me to jump and start the practice. And then, suffice it to say, both my wife and I, she felt safer, and I felt safer with her in jail with criminal clients than in a classroom with middle school students on a number of levels. And so we started the firm in October.

Jordan Ostroff:
She came on full time the following April, so six months later, before the school year ended. And then we had to figure out sort of how not to step on each other's toes, which led to, like, me going business owner marketer route, her going more lawyer focused route, and since then, it's been great, like, since we had that.

Ali Katz:
That division.

Jordan Ostroff:
Yeah. Thank you.

Ali Katz:
We see that. We see that a lot. We work with a lot of husband-wife partnerships in our Advanced Growth Mastermind, which is part of our Personal Family Lawyer training program, once lawyers are ready to really build into businesses, and then we'll end up working with the husband-wife team. And sometimes one of them is not a lawyer. Oftentimes, they both are. Either way, they're doing it together. And exactly what you've said is the key.

Ali Katz:
They have to decide on their roles, who's in what role. Don't step on each other's toes. Stay in your lane. And was it clear, was it absolutely clear that you were going to be business marketer and she was going to do the legal part?

Jordan Ostroff:
No. So my wife will tell you she's the best, that I'm the best litigator she's seen, which is very kind of her. I just, like, I had this conversation with a friend when we were at the state attorney's office. Even before this, I was like, look, we're in downtown Orlando, like within 1000 ft of us, there's probably 100 great lawyers and there's probably like three great law firm businesses or whatever you want to call it. Like the Morgan and Morgan main office is right down there. So they've got a ton of phenomenal lawyers, but like, there's, you know, it's one business. And so, like, we always had an easier time finding great lawyers than we did from the business side. And I think it was more a question of, like, I think I could have gone either way in that split, but I don't think my wife could have gone to the business owner split.

Jordan Ostroff:
Like, she truly loves, like, actual litigation or she loves teaching people about actual litigation. Like, it's very interesting to see, like, I don't think the teaching part of the job was the problem for her. I think it was the students.

Ali Katz:
Yeah.

Jordan Ostroff:
And so, like, now she, you know, she teaches actually at UCF, even though she's not a knights grad like either of I, she does a one class a semester and whatnot. And so it's turned out to be the right fit for both of us, even though in that moment it wasn't that clear.

Ali Katz:
And you as the business guy, the marketer, no longer doing the legal side, you studied everything that there was at that time, soaking up all the knowledge from the best marketing minds in the industry. Who were some of your teachers? Who were some of your teachers? Because I, you know, I go back to. I'll just, I'll share where I go back to. Dan Kennedy. Were you ever a student of Dan?

Jordan Ostroff:
No. But Ben Glass, Ben Glass's Renegade Legal Marketing, was like the first book that I was like, oh, my God, this is a thing that can be done. Whoa.

Ali Katz:
So when I was on a plane flying somewhere, and I picked up Entrepreneur magazine or Ink magazine, I can't recall, and Dan Kennedy had like a full page, what I now understand to be an advertorial. I didn't know that's what it was. I thought it was an article, but an advertorial looks like an article. And literally he was talking to me. You know, I had built this successful law practice using a new methodology that I had discovered for serving families with young children with estate planning, filling a hole. And I had been thinking about for so long, oh, I want to take this out and teach it to other lawyers. I love to teach. Like, sounds like your wife as well.

Ali Katz:
I love to teach. And then I see this Dan Kennedy advertorial, which is a full page on how successful solo professionals of any kind can take their knowledge and work from home. This is 20 years ago now. There was nothing really about the Internet. It was like, use your phone to make millions of dollars working from home, taking your knowledge and bringing it to the world, have total flexibility of your schedule. I was like, oh, my God, who is this? What is this? I want this thing. And eventually I ended up getting to Ohio to one of his events, and Ben Glass was the only other lawyer in the room. It was me and Ben Glass.

Jordan Ostroff:
There we go.

Ali Katz:
Yeah. And so I love that he was really, in some ways, the first person that taught you about lawyer marketing.

Jordan Ostroff:
Yeah. And where. I mean, because, like, look, you can get all the Glengarry Glen Ross always be closing cold, cold call, whatever, but, like, we can't do that as lawyers. And so it was, like, really interesting to read a book that was more lawyer focused.

Ali Katz:
What was the biggest eye opener for you when it came to Renegade Lawyer Marketing?

Jordan Ostroff:
From that book specifically, I think, like, the having a newsletter. And so, like, I bought a traffic ticket business from other lawyers in town. They had, like, 10,000 prior clients. And I kicked myself because, like, I didn't think about sending email blasts to all them until reading Ben's book, which was like, a year and a half later. And I was like, man, I wonder how many thousands of dollars I left on the table by, like, not having a $49 a month mailchimp or constant contact account, like, with this thing that he's talking about. But, you know, you live, you learn, and you do it better the next time.

Ali Katz:
And then you did that, you implemented an email newsletter.

Jordan Ostroff:
Well, so, yes, at some point, I. So, like, I don't know, in terms of the full story or in terms of this part of the story.

Ali Katz:
Well, yeah, I mean, did you, did you, as soon as you realized, oh, I should have an email newsletter, did you immediately get one up and running and put it into that traffic firm, or did you wait until you had your own PI firm?

Jordan Ostroff:
No. So we launched. Yeah, I would say so if I bought the firm in '16. Yeah, probably '18. So a year and a half, two years later, came across Ben's book, and that was helpful towards that. And then just had a complete. Was able to have a really intentional breather of the entire concept of marketing through the context of my kid being born. And that was where I really kind of rebuilt the stuff from a base of knowledge instead of a base of just being a complete idiot who made it work.

Ali Katz:
I'm sure you weren't a complete idiot. Just uninformed.

Jordan Ostroff:
Aggressively uninformed then, how's that.

Ali Katz:
Aggressively uninformed. Well, we come out of law school aggressively uninformed, you know?

Jordan Ostroff:
Yeah, but I just, like, so I, UCF in Orlando, like, we talked about, you know, went to law school in Orlando, was a prosecutor in Orlando, and I did trial team, like, the whole time through undergrad and then coach as a lawyer. And so, like, I had, you know, team ten years of people in the area of lawyers, of judges, of contacts, and I was able to tap into them for some referrals and got, like, a couple hundred thousand dollars worth of referrals my first year and was like, oh, this is great. Like, I'll hire a marketing company and they'll fill in the gaps. But, like, I didn't know enough to have that conversation with them. They didn't ask me, like, do you have a sales process? Who do you want to work with? Those kind of things? And so, like, I was able to spend my way into a bunch of debt and a bunch of bad mistakes from having, like, some core of success that I could leverage to maximizing the problem.

Ali Katz:
I love that, I leveraged my core of success to maximize the problem and took all the money that I made and invested it in the wrong people who couldn't actually help me so that I could learn what I needed to do to actually be able to help myself.

Jordan Ostroff:
Well, to be fair, like, I don't even know how much of it was them versus me. Like, if I had a real sales process at that time, a lot of this would have gotten a lot better, you know, and it was just a question of not knowing the full breadth of what is required for these things.

Ali Katz:
I love that that's. Yeah, I love that that's what you're pointing to is like not having a sales process. I see that all the time. It's, in fact, one of the very first. It is the first thing that I ever talk coming out of my learnings from Dan Kennedy. Well, what I tried to do at first, after I learned from Dan, the very first thing that I tried to sell was a package of legal documents called the Kids Protection Plan, because I identified that there was a hole in the estate planning for families with young children, which, by the way, there still is. Jordan. And so since you have a little one, I don't know if I've sent you my book yet "Wear Clean Underwear"?

Jordan Ostroff:
No, but it's one of the rules I live by. So sometimes you have to flip it inside out. But at least you know.

Ali Katz:
Well, once you're a parent, wearing clean underwear alone is no longer enough, Jordan, there's important legal planning steps you need to take. So I'm going to send you a copy of my book. Great. And so for listeners who want a copy of the book, you can go to personalfamilylawyer.com, and at the top it'll say "book". And you could get a copy of the book as well. You know, I had identified that there's this hole in legal planning for families because I'm a mom, too. I'm at dinner one night with my husband, realizing that even though I had an estate plan, if we didn't make it home, our daughter was with a 16 year old who was going to have no idea what to do.

Ali Katz:
Where's the will? Even if she knew where the will is, the person we named as guardian lives 3000 miles away. And the authorities are going to have no choice but to take our daughter, Kaia into the care of strangers until they could figure out what to do. And I was extremely motivated to solve that problem. Like, that was not okay with me. So I solved that problem, wrote a book about it, started selling that to consumers. Kids Protection Plan. It's the first website that I ever created, kidsprotectionplan.com, still exists today.

Ali Katz:
Now there's lots of online legal document providers. But at the time, other lawyers were like, what are you doing? Why are you selling legal documents online? Like, they couldn't understand it.

Jordan Ostroff:
A lot of lawyers still don't understand it, though, Ali.

Ali Katz:
Yes, yes, exactly. A lot of lawyers still don't understand it. Yes. Yes, it's true. Yeah. We are going to ultimately need to get to the place and where, and this is really what Personal Family Lawyers about today is. You don't need to compete with the document providers. Like, let the document providers provide the documents and you provide the counsel. Right. Differentiated service.

Ali Katz:
So when I went to the Dan Kennedy event where I met Ben, I ended up hiring my first real business coach, this guy Dave, who helped me to see that the very, like, I was trying to do so many things. He said, number one, you need a win because I had just gotten divorced and I was spending all my money trying to learn how to sell things online. And he said, you need a win. What is the thing that you know how to do that no other lawyers know how to do that you're doing successfully right now? And I thought about it for a while, and he's like, and it can't be the Kids Protection Plan. He said, it's not that. He said, it's something else. What is it?

Jordan Ostroff:
Why not that one, though?

Ali Katz:
Because that one was a consumer product. And he said, you cannot afford to build a consumer product. You need to bring something to the lawyers, for the lawyers.

Jordan Ostroff:
Got it.

Ali Katz:
And he. And what it was was, oh, I know how to sell estate planning better than anyone else. I have a whole system for it. I've developed this system over a couple of years now because I was losing clients to, I have to think about it, or not being able to explain our pricing, or they could get it cheaper somewhere else. And I've solved all of that.

Jordan Ostroff:
And he said, great. Well, then in six weeks, we're going to do a teleseminar. This is before webinars. We're going to do a teleseminar. We're going to invite people to a phone call, and we're going to sell your training on how to engage clients.

Jordan Ostroff:
There we go. No PowerPoint through the phone.

Ali Katz:
Oh, no. No PowerPoint. And in fact, Jordan, at that time, no training. I didn't have a training.

Jordan Ostroff:
Like, truly.

Ali Katz:
I truly had only the idea that I could do this. And I said, wait, I can't do it in six weeks. That's too fast. So he said, okay, fine, eight weeks. So we ended up doing it.

Jordan Ostroff:
Good for you, at least getting the two extra weeks. At the beginning, I would have been like, yeah, no problem. And then the night before been like…

Ali Katz:
Well, what ended up happening is that on that call, this was 2006. We had 750 lawyers register for the call. I was really blown away. And we did the call, and this is back in the day again, before Zoom or anything like that, we had instant teleseminar was our technology, and we had the real issue of too many people trying to get on the line. Then we had space for. And people were pissed they couldn't get on the line. And my biggest fear was that I was only going to enroll one person because I. I was going to have to create the whole program for whoever bought because I didn't really have a program yet.

Ali Katz:
I knew what was going to go in it. We ended up doing about $115,000 of sales in a 67 minutes phone call. Changed my life. Yeah, yeah. Was running around just screaming like, oh my God, oh my God, oh my God. And over about six week period, we did about $250,000 in sales because what we were teaching was exactly what you're saying here. How to get hired and paid by clients, how to sell. And half the people that bought the program ended up returning it because it was so put together in a, you know, it was like, it, it was ugly market.

Ali Katz:
It was like really ugly. You know, it was like spiral notebooks and binders. I don't have them here with me, but the originals, you know, are just funny, you know, these plastic notebooks, it was literally everything I did in my office, my scripts, and. But they had to, like, actually work to implement it.

Jordan Ostroff:
Substance over style.

Ali Katz:
But the other half of the people who could actually see what they had started implementing it and started sending me unsolicited testimonials. Oh my God. I just raised my fees from four hundred dollars to four thousand dollars. Oh my God. I've engaged the past seven clients I've met with 100% engagement rate and I knew I had something. And I share this story because today, still 20 years later, it's a problem. Lawyers don't have a system for getting hired and they're trying to solve it by hiring marketing agencies. And they're spending so much money on Google Ads or on SEO or, I don't know, what else did this marketing agency sell you?

Ali Katz:
Would you love direct support to help you grow your law practice into a business you love? Go to newlawbusinessmodel.com/show and sign up for a call with one of our trusted law business advisors. Each of our advisors has been trained directly by me over the past five years plus to help you chart your path from wherever you are now to where you want to go as efficiently and effectively as possible.

Ali Katz:
You're ready to grow. We are here to help.

Jordan Ostroff:
Ali, I bought everything from everybody. I bought leads, I bought SEO, I bought ads, I bought social media ads, I bought Facebook ads, I bought done for you, I bought work with you for this. I bought templates for that. I bought, I mean, it was…

Ali Katz:
Because they're really good marketers, the marketing agencies.

Jordan Ostroff:
Well, they're good salespeople. And look, one case it pays for itself. One case it pays for, one case it pays for itself. Well, the hundred things that didn't even bring in one case didn't never pay for themselves.

Ali Katz:
Because if you don't know how to sell, it doesn't matter if you buy leads, if you generate leads. If you get SEO, if you get calls, if you don't know how to sell, or if you're selling a service that you can't actually even afford to deliver on, maybe that's not so much of an issue in PI. Is that an issue in PI?

Jordan Ostroff:
Not so much in PI. But like, I started out, you know, I coming out as a prosecutor, we did criminal defense. And so there were definitely times where I probably paid more money for a lead for a client that wanted to pay me less and ended up losing money over time.

Ali Katz:
Yeah. And so, and so to me, and this is why we start with this foundational in our programs, is you have to know how to sell a service that you can afford to deliver on. Period, end of story. Don't ever spend a dollar in marketing before that.

Jordan Ostroff:
Oh, so, yeah, I mean, I always tell people, so, like, get fulfillment down. So I think that's what we're talking about, delivering the service. And then you move to the sales process because now, like, you know, you are concerned about one person hiring you, but a lot of lawyers are concerned about 100 people hiring them in one day that they can't handle. And then. Yeah, and then you go, you know, you work your way up the funnel towards marketing now that you have the foundation of fulfillment and the sales process to get there.

Ali Katz:
Yeah. And so you figured that out after spending insane amounts of money, you know, really to learn the hard way.

Jordan Ostroff:
Very kind of you to say, I figured it out. I realized where the holes were in the process.

Ali Katz:
Yes. And so you solved it in your law firm? Driven Law firm.

Jordan Ostroff:
So at that point, Jordan Law.

Ali Katz:
But, yeah, Jordan Law. Okay, so that's also an interesting thing to talk about because we do see a lot of lawyers begin with their name. You began with your name and then you shifted. Why'd you do that?

Jordan Ostroff:
So I was never going to be Ostroff law because nobody will remember my last name. So I was like, oh, Jordan law is great. Then, you know, Michael Jordan. And we have, man, I wish I had the original logo. We did like the MLB logo. So like, red, white and blue across, like every sports logo. And it really wasn't intentional, but it worked out pretty well. And then everybody thought it was cool.

Jordan Ostroff:
Jordan answered the phone, Jordan handled their case, Jordan talked to them. And then at some point I stopped doing that. And so it's like, what the hell's the point of people calling a firm to not have the name on the door actually speak to them? And my wife had the idea for Driven Law years ago, and finally, I owned a marketing company, and the marketing company was like, oh, let's do the rebrand. It'd be a good opportunity that way. And it has been. So it's been actually just over here. It's April 1 of last year. We did the rebrand.

Ali Katz:
Oh, wow. Okay. It's been really recent since you rebranded.

Jordan Ostroff:
Yeah, a year. Year and three weeks.

Ali Katz:
Got it. And really, now you're creating a business that you can sell. Do you see that future reality where you sell this business?

Jordan Ostroff:
I mean, fingers crossed my child does not become a lawyer. Fingers crossed he goes into, like, HVAC or anything else, and then, sure, you know, look, everything is. Everything has a price.

Ali Katz:
Yes. Well, it's funny that you say that. My son is in construction and my daughter's in makeup. Neither one of them did go to law school. Although I have gotten to a place now where I'd actually be really happy if they ended up choosing it, because they did figure out a way to love it. But there was a time where I was like, there's no way. I don't love it, you know? But your son could love his law firm.

Jordan Ostroff:
Arguing with me and driving me nuts and making. So, like, we took away screen time, or we have very limited screen time for him, and he's like, hey, don't you like Bluey and Gravity Falls and all the other shows that we watch together? Yes. He's like, so really, you're punishing yourself. And I was like, thanks, five year old at the time. Like, you're correct. I am punishing myself by not giving you, you know, unlimited TV and iPad. So, yes.

Ali Katz:
Yep, it's true. Well, you're also punishing yourself, because now I'm imagining that while he's not having screen time, you're having to do some form of entertainment, kid entertainment. Is that. Oh, what's replace the screen time?

Jordan Ostroff:
Yeah, we have a blast. We just shoot each other with Nerf guns and throw balls outside and play hide and seek. It's a lot of fun. I'm very lucky.

Ali Katz:
Yeah, that's way better than the screen time anyway. So tell him he's wrong. It's not a punishment at all. It's the best thing possible because you get to actually play. You're having a great time. So you've built this business that maybe you'll sell one day, maybe you won't, but you'll be able to because it doesn't have your name on it, doesn't have Heather's name on it. Nobody's calling up asking to work with Jordan or Heather for that matter. If they get you, great.

Ali Katz:
But you really, do you really, you know, this is the NewLaw podcast for entrepreneurial lawyers. You are without question, an entrepreneurial lawyer. Did you know that you were going to be an entrepreneur? Was that an awareness that you had going to law school or coming out?

Jordan Ostroff:
No, I thought I was going to be a prosecutor for life. And then even you put in a three year commitment, I would say the two year and nine month mark, I thought I was going to be prosecutor for life. And then at the two year and eleven month mark, I was like, oh, man, my days are numbered.

Ali Katz:
What happened? What happened in that? What, what happened there?

Jordan Ostroff:
Uh, so I was doing at that point what was called, um, general felony. So, like, that was, you could not be killed. You could not have killed somebody intentionally, but you could have done it recklessly. So, like armed robberies, uh, DUI manslaughter, like reckless deaths, those kind of things. The next promotion was the sex crimes. I applied for it. They told me I didn't get it, and I was weirdly happy. They told me I would get the next one, though.

Jordan Ostroff:
And my heart, like, dropped through my body and I was like, oh, I don't want the next promotion. Oh. Huh. So it was a very interesting way to figure it out. And I was like, so I guess I can't stay here. Like, I don't want the next move.

Ali Katz:
Yeah. How did you actually then make that leap? So now you're aware I can't stay here. What was that? Aha. Of, oh, I can start my own practice and here's what I'm going to do.

Jordan Ostroff:
So Orlando has a great legal community, especially from the criminal side. I guess I was a easy to work with prosecutor. Cause like 20 or 30 defense attorneys were like, oh, yeah, I'll talk to you, we can get lunch. And here's what you do. Here's what the transition's like again, going back to the me not knowing I did not ask enough questions about the business side of it. So I got a ton of great advice and people sent me copies of motions. And my wife, being a PD, helped me with like, the filings on that side and whatever else, but not a ton on the business aspect, which goes into the rest of that part. But I am so, so, so thankful to all those people.

Jordan Ostroff:
And one of them offered space and extra cases. Corey Cohen, who's. It's a nice shout out in the book, and I gotta get him a copy as soon as I have it. So he hears this. Sorry, Corey, it's coming. And, you know, and that helped. From that standpoint, that was a good foundation to get everything else going.

Ali Katz:
So you spoke to other lawyers about the legal side of the defense practice. You found an office, another lawyer who would give you space. That's also, by the way, how I made the transition out of the big law firm myself. Found another lawyer in my community that would give me office space. I traded 20 hours a month for the space because I didn't have money to pay rent. Did you pay rent right away?

Jordan Ostroff:
I did. To be fair, though, it's the best rent I've ever paid because I got probably ten X in cases from the office for the rent. So.

Ali Katz:
Yeah, for the overflow. Yeah. So you got some cases right away. And so now let's fast forward to. You've built a business. You're on the business side, your wife is on the legal side, and you decided to write a book. That's what brought you here. The "Love your law firm book". It just launched ten days ago now, while we're recording this. And that book was a long time in the making.

Jordan Ostroff:
A long time, yeah.

Ali Katz:
What had it finally? Okay, fine, I'm ready. It's. Now's the time.

Jordan Ostroff:
That's a great question. So the book started basically as therapy. Like, I hated it. We were hundreds of thousands of dollars in debt. We were miserable. We were. And I was like, I'm just gonna write. Like, I'm gonna write my way through this.

Jordan Ostroff:
And, you know, like Gary Vee says, document, don't create. So I guess I was sort of creating something, but I was mostly just, like, documenting the horror. And then I realized, because it was a book that was, like, my story, it was never gonna finalize until I died. And thank God I haven't died yet. And hopefully that won't come for a long period of time.

Ali Katz:
Yeah.

Jordan Ostroff:
So my wife and I and our son, who was three to four at the time, three to five at the time. We did a 13 month cross country road trip, and I was like, all right, I'm done. Like, this is a good end of the book. I think part of that's in the story, but, like, now we're, you know, getting back into the flow of things. So let's call this the end of the book, at least the first book or whatever. And then that let me release the book, whatever it was, probably 16 months later or so, but at least then.

Ali Katz:
Because a chapter of your life died.

Jordan Ostroff:
Well, yeah. I mean, I wasn't really writing an autobiography. But, like, I was doing things differently and learning and changing the firm. And so, like, you know, there's going back to the. And changing Jordan Law, to Driven Law. There's going back and talking about not being at Legalese anymore. Like, there's so many life events that I had to update that finally I was like, you know what? Like, just, I need that date to ever get this out there and hopefully help people.

Ali Katz:
You mentioned something. You were hundreds of thousands of dollars in debt, hating your life as a result of the decisions that you made when you really didn't know about business and being an entrepreneurial lawyer. You were a lawyer, but just investing in everything to learn the hard way. And you decided to go on a 13 month road trip. Was that in the. Were you still in that place?

Jordan Ostroff:
Oh, no, no. There's a, like, four year window. That's like, to me, that being able to go on the road for 13 months and have the firm do great and hit our KPIs and keep whatever, like, that's the culmination.

Ali Katz:
That was the result.

Jordan Ostroff:
Yeah, the end of that journey.

Ali Katz:
Got it. Okay. And that because you, at that point, really, that 13 month road trip was, I've built a business that can run without me being there every day. And now me and my wife and our child can go on this 13 month road trip. And the business is running. The PI firm is going. It's serving clients, it's generating clients, it's engaging clients. Now we can go.

Jordan Ostroff:
And Ali, I'll take it a step further. My business runs better when I'm not here. Like, flat out. It is not a question if it can run without me. It's a question of the less that I am in there to meddle with everybody and everything. And the more I can just be like, this is our big long term picture, the better everything goes for everybody.

Ali Katz:
Well, it really makes a lot of sense. It's the same for me as well, by the way, in my own businesses, because we're creative, entrepreneurial types who always come up with new ideas and we mess things up when that's the case. If we can just get everybody on a path and follow that path, business runs great. It's interesting that that was, in some ways, your first exit. So when we take lawyers through our journey, they first learn the service delivery model and how to engage clients. That's like bare minimum foundation. You've got to know how to serve, and you've got to know how to get hired and paid. Then it's all about marketing.

Ali Katz:
And building your team and getting your technology and systems in place, and then you're setting up for this exit. And we see that there's two kind of exit paths. One is get the firm running so that it can run while you take long vacations, in your case, a 13 month road trip, or sell it. And it sounds like you've gotten the firm to a place where you actually don't need to sell it because it creates cash flow. You can work in it when you want. Your wife still loves working in it. That's what she loves to do. There's no reason to sell it at this point.

Ali Katz:
But you really have gotten to that, what I will call one of the exit growth paths. So for lawyers who want to follow in your footsteps and really shortcut all of that learning that you invested in hundreds of thousands of dollars to learn what not to do and want to learn from your therapy, the book is called "Love your law firm". I assume it's available everywhere.

Jordan Ostroff:
It's on Amazon. I don't know. Is that everywhere? Amazon will deliver to you everywhere.

Ali Katz:
That's. Well, I'm actually in Costa Rica where I spend half the year and Amazon does not deliver here. It's one, it's one of the.

Jordan Ostroff:
Take it back.

Ali Katz:
Yeah, it's one of the positive negatives, I guess, about being here. Can't get everything overnight, but also can't get everything overnight. So it's a, you know, paradox. So "Love your law firm" is the book. And you are working with law firm leaders who really do want to be the CEO in their business as well.

Jordan Ostroff:
Yeah, you know, I want to help more lawyers create their version of my journey. And hopefully, you know, it's not as crummy at the beginning and it's just as good or better at the end. So that's, that's what I'm, that's what I'm hoping to do. I'm on a mission to help more lawyers be happy.

Ali Katz:
Yes, yes. Well, we share that mission.

Jordan Ostroff:
Yeah.

Ali Katz:
Lawyers can be happy with. And the way that I look at it, Jordan, I'm curious if you agree with me. We are actually the luckiest, I think, of professionals because when we are using our law degree in the right way, it becomes this extremely high value asset that is actually relatively rare because most lawyers actually don't know how to use their law degree in the right way. And because I've worked with a lot of business owners in a lot of different industries, and when I look at all of the other industries, most service providers either need to create their service from scratch. They can't like step into something that's already proven. So then they have to create everything from scratch. The service, the sales, the marketing, the fulfillment, everything. Or they are in a model like financial services or selling insurance, where they may not even really believe in what they're selling, but they have to sell it anyway. Whereas lawyers, we get to believe in what we're selling.

Jordan Ostroff:
I hope so.

Ali Katz:
I also do meet a lot of lawyers who don't believe in what they're selling, but I think it's just because they're not using their law degree in the right way.

Jordan Ostroff:
I also think there's three years and $150,000 moat built around being a lawyer as opposed to, you know, getting a financial, depending upon the series, licensing and whatnot. For that, you can certainly, you could do it cheaper. I'm sure there's ones that have way more education than I do, which is helpful.

Ali Katz:
It is, it is. And so, you know, if you are a lawyer who is listening to this and you are not currently happy, you don't love how you are using your law degree, and you know that there can be a better way. You're right, there can be. And Jordan and his wife are perfect examples of that. And so pick up a copy of "Love your law firm", read it and you'll see exactly what you can be doing. And so, Jordan, what would you leave listeners with today as just one of the most important things for them to take away? To really love their lives as lawyers or love how they're using their law degree?

Jordan Ostroff:
Yeah, listen, be selfish. I'm going to give you that permission. It is amazing. Like, in the worst moment of everybody's life, they come to you and they're like, I just got arrested. I just got into an accident. You know, I'm thinking about death and making sure the kids are okay and we take on all these problems. So, like, there are moments where you have to put yourself first so that you don't burn out, so that, you know, you can't pour from an empty cup, so that you can't drive yourself miserable. And by you being selfish, the certain amount of time, the right amount of time, you show up better for clients, you can focus on doing the work correctly, you can make sure you surround yourself with the help that you actually need, and it's so much better. Instead of thinking like, ah, you know, I have to go, I have to come last.

Ali Katz:
That is probably the best advice you could possibly get, which is take care of yourself. Take care of yourself and it is true. That is one of the major things, really, nobody teaches us. And so take that advice today. Consider what it looked like if you were taking better care of yourself and putting yourself first, because you're the machine. You're the machine in this engine, and without you, there's nothing. So I love that advice. Thank you, Jordan. That's so great.

Jordan Ostroff:
Thank you so much for having me.

Ali Katz:
And maybe I'll add one piece, which, which you've really done so well, which is that your kids are only little once. Kids are only little ones. And Jordan, you're making the most of that. I love seeing that. My kids now are 21 and 24 and it went like a blink of an eye. And so just for all of you out there with kids, remember that your kids are only little once and do what you can to make the investment. And it's probably honestly going to be a three to five year investment of building a business around your law degree so that you can take 13 months if you want, or even two weeks.

Jordan Ostroff:
Or even an afternoon, an hour early going to the Spanish show at the school, you know, whatever. It's like. I love what you talked about earlier, though. You know, get a win. Get that quick win and just keep snowballing it into bigger and bigger wins.

Ali Katz:
Yeah. Yeah. Jordan, thank you so much for joining me today. I really appreciate it. And I loved your book and I, and I know everyone else will as well. So thanks for, thanks for being here and I look forward to connecting with you again soon.

Jordan Ostroff:
Thank you so much.

Ali Katz:
Bye, everyone.

Ali Katz:
If you loved this episode with Jordan and you are inspired to either start your own law practice or turn your existing law practice into a business you love and you're either considering estate planning or you are already offering estate planning and you really want to do it in a way that is lucrative, that your clients love, that you do not compete with AI or cheap legal or even up and coming financial advisors who are trying to take all the estate planning business we can help, simply go to newlaw.co/show and book a call with a law business advisor so we can help you determine what is the fastest path to turn your law practice into a business you love and whether you are the right fit for our support. Go to newlaw.co/show. See ya on the other side.