May 3, 2022

Imparting Values and Business Skills to Your Kids with Jordan Ostroff


Jordan Ostroff is a visionary entrepreneur, President of LegalEase Marketing, Managing Partner of Jordan Law Fl, Host of multiple facebook live show and the Chair of Big Brothers Big Sisters of Central Florida.

From a young age, he knew that he wanted to be a lawyer - even when he had no idea what that meant. During college, he began competing in trial competitions across the country, where he was an award winning advocate for fictitious cases.

After law school, he started his legal career as a Prosecutor for the State Attorney's Office. There he cut his teeth in the trenches and learned how to truly be a “real” lawyer.

Today, he manages Jordan Law FL, a firm focused on personal injury and helping injured victims get the recoveries they deserve. His firm utilizes the latest technology and automation to provide top level legal work, with a low volume of cases but a high touch level of care and compassion. The son of a postal employee and a substitute teacher, he is the first lawyer in his family, and with no business experience his first few years of running a firm were incredibly difficult.

He was consistently taken advantage of by other marketing companies, because he didn’t get it and didn’t know what to ask for or what to look for. Having been faced with the prospect of learning how to run a successful business or close his firm and file for bankruptcy, he choose the later. Now Jordan works 3 days a week, usually 20-25 hour each week.

This new path culminated in Jordan starting LegalEase Marketing, a holistic lawyer focused fractional CMO company. Part full service marketing company, part consulting firm - Jordan shares all of the info that he wish he knew when he started his firm and focuses on helping other lawyers not make the 1,000,000s of mistakes he’s made. LegalEase prides itself on treating its clients the same way those lawyers treat their clients - they come first, they own their "file," no conflicts of interest, etc.

Additionally, Jordan is the host of Exhibit A(ttorneys) a live show where he interviews lawyers and experts on how to build the best lawfirms and be happy as a lawyer. He also hosts The O Know Show, where he interviews people about the cool things going on in Central Florida, as well as the Chair of his local Big Brothers Big Sisters chapter a non-profit that pairs hundreds of underserved children with professionals who mentor them for most of their lives and help them achieve success.

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Transcript


 josh
 Good day fellows. Welcome to uncensored advice for men. Hey, I have a, one of my friends on the show and he presented me with a challenge. During this interview, I've got a challenge. If I can, if I could pose a question that either stumps him or he goes, dang, Josh, good question. This guy has been on tons of interviews. He has a marketing company as a, a bunch of legal companies. He does a bunch of cool stuff, but if I could stump him with a question or get them to good question. He's going to drive his butt to Ocala and take me out to lunch challenge accepted ladies and gentlemen, actually this show for dudes. Welcome Jordan to the show. Jordan welcome, man. 


 Jordan
 Yeah, thanks for having me. That is, that is hilarious. I love the ladies and gentlemen, wait, scratch that. 


 josh
 Scratch that, just that saying may get me in trouble where I'm like, oh, you excluded people. I'm sorry. This is a show for men. It's uncensored advice for men. This shows for you guys, Jordan, tell us about who you are and what you do. 


 Jordan
 Sure. So my name's Jordan Ostroff. I am a lawyer by trade, so I run a personal injury firm in Orlando, Florida. I am actually though a marketer or business owner by actual work. I created legalees marketing to help other lawyers avoid the same stupid pitfalls that I went through when building my firm. 


 josh
 Yeah. Awesome. You said by actual work is, marketing and such like I wouldn't do, what did you mean by that? 


 Jordan
 Oh yeah. So, so like I don't do legal work. It's funny to tell people, like I have a bar card, I am a licensed, I'm licensed to practice law, but ultimately I've always found it super easy to find amazing lawyers who do phenomenal work. I found it so much harder to find amazing marketers or amazing operations managers wherever you want to call like the true business side. I have constantly not forced myself, but constantly gone on a journey to learn that stuff while hiring and employing a bunch of great, phenomenal lawyers who are way better than I will ever be at that part of it. 


 josh
 Cool. A bar card. All right. My bar card is probably a little different than your bar card. Your bar card is your legal practice. My bar card is by connections here in Ocala. 


 Jordan
 This is the most expensive piece of plastic that I keep on me. I don't know if anyone else see the video, but I'm holding up. It is literally you get an actual card and it has no ID on it. You just sign it. Like this gives me so many rights and opportunities as well as responsibilities based upon this random piece of plastic. 


 josh
 Okay. That piece of plastic, how much did that bar card cost you? 


 Jordan
 Great question. In theory, I got about $110,000 in scholarship money for, from my law school. I still took out about $37,000 in loans. I still paid back about 50 to $60,000 in loans, along those lines. Plus I pay bar news plus I do pro bono plus all of that. Like my house is slightly more expensive, but slightly more expensive. 


 josh
 And it doesn't even have your photo. I could literally take that and I could go, Hey, here's my bar card. 


 Jordan
 Well, but then you'd be committing a felony. 


 josh
 That's a felony. 


 Jordan
 Practicing law without a license. Yeah. 


 josh
 I was just holding the car dinner. What, what benefits do you get? Would that bar card that I don't have? 


 Jordan
 I can randomly walk around jails on supervise for the most part. That's that's an interesting one. I. 


 josh
 Like to do that on Friday nights. 


 Jordan
 There we go. Yeah. Well the, let me back out though. That's the, that's the benefit. I get different access into port houses. People think I know what I'm talking about. You know, that's a big one. Like you're a lawyer. You must be knowledgeable. 


 josh
 About. 


 Jordan
 Every topic. Yeah. It must be smart. Sure. Yeah. So I don't know what else. I don't know. I can give people legal advice, which is a felony. If anybody else does it, which is a crazy concept and how much knowledge you can literally go to jail for sharing or providing other people with. 


 josh
 And here's the disclaimer on this show? I am not an attorney nor will I ever be one talk to an attorney like Jordan. So that's my disclaimer for the show. All right. Jordan, one of the things that you said is super important to you as your, as were discussing, were talking business and deals and I was like, dude, what's really important. And you're like, I talking about fatherhood. All right. I, I assume your father, I, I am, but I want to, you talk with the guys, talk to us about, talk to us about your family. Talk to us about your kids. Talk to us about you being a father. 


 Jordan
 Sure. Just have one kid, he just turned four at the beginning of this month. He's freaking hilarious. He has finally hit that time where like, he's not just parroting back. What I say is like truly created his own opinion about things. It's amazing to be like, oh my God, like I made, like, I made this, but I made him this way from, raising him a certain way. 


 josh
 Yeah. Yeah. When our kids start talking back, like when they repeat back what we said, so I forget what it was. I was in the house with wife and my son also four, he goes, what? The freaking hell? I was like, oh no. I was like, oh, where'd you hear that from mom? I was like, oh geez. Oh baby. So you know, they are parents. They will speak back what you say. I'm going to get in trouble with this one. As you're you see this four year old kid and you said, I made this thing, right. Like I, I made that best 30 seconds of your life. Right. You that you, 


 Jordan
 Hey man, 45. 


 josh
 Seconds. Right. Y w what was life like before this kid? Or what was, let me ask you better. What was Jordan like before this kid? What's Jordan, like now, what are the differences that you've seen in your own life? 


 Jordan
 That's a great question. Oh, 


 josh
 You said it lunch. 


 Jordan
 All right. Fine. No problem. We'll schedule a time. I look at, can we curse on this? This is uncensored. 


 josh
 Censored. All right. Don't say, don't say which word do you want to say? 


 Jordan
 I mean, I want to say most of them, but I'll limit myself. 


 josh
 Yeah. I think you're allowed to say 13 before we get shut down. 


 Jordan
 Okay. There we go. I'll, we'll keep track of like that scene in super troopers, a little belt. 


 josh
 Every time you. 


 Jordan
 Look there is a type of person who gets attracted to being a lawyer. For a lot of it, there's some semblance of being an a*****e. Like, ideally I think the best lawyers get into it to truly want to help people. There's this component of like, we are the only we and sports are the only truly adversarial professions. At some point, me being an a*****e to somebody else is super beneficial to my client. Having a kid has like, completely changed my views on some of that. Like, I think it's made me a lot more patient of a person. I think it's made me less of a jerk in so many circumstances. Also it really, I did not realize how unimportant my life was until I truly had this thing that was reliant upon me. 


 josh
 Yeah. Does he have a cool beard? Like you do, he's four years old. You got a great beard. Does he have a beard yet? 


 Jordan
 No, but he, every now and then we'll draw like Sharpie or pen on his face to give himself as his dad beard. I'm like, and it's like in 20 seconds, like we are, he did it yesterday from like, I dropped my wife off at her lunch meeting and then on the way to eat and I don't have to like the science center. Maybe a quarter mile come back and he's like all up in pan. I don't even know where he got the pen. I was like, what, we're going to do it. I'm just going to, you're going to walk around with a fake beard drawn on you. So we'll see what happens. 


 josh
 Heck yeah. Heck yeah. As you're fathering, as you're learning to be a father, right. What are some of the biggest challenges you've had in terms of fathering? 


 Jordan
 The first part of it really becomes, I think you have to figure out what you want to be intentional about and what you intentionally want to not be intentional about if that makes sense. 


 josh
 Nope. Okay. 


 Jordan
 Sure. I read rich dad, poor dad, like within either two months before he was born two months after he was born. I had read it before as a me book. In that moment I read it as a parenting book. Like, what are the financial things that I want to teach my kid? At the flip side of that, like he is super into trucks, tractors, dump trucks, whatever. I don't know anything about those. I can definitively tell you, I had, I was not intentional about making him like those things. Cause I wanted to see like what he genuinely enjoyed. Balancing this, like, I have a very specific concept of how to explain money and work to him versus like, I definitely don't want to force him to like the same things as me. I want him to figure out what he truly enjoys. I am intentionally unintentional about that part, but very intentional about the like financial stuff. 


 josh
 Yeah. Okay. I get it now. As your four year old boy is growing, what are the things that you want to impart to him as a father? What, what things do you want to be intentional about? Hey, I'd like this for you. 


 Jordan
 I am of the belief that the meaning of life is to leave the world a better place than you found it. I think when it comes to your children, that is the easiest way to do that. Putting them in a better position, hoping that they are better people than you are, or a better person than you are, et cetera. It's cool to play this very analytical. What about my childhood? Do I want to keep, what about my, what about my childhood? Do I want to change for him? What about, how I was raised? Do I want to intentionally do differently? Do I want to try something else? Do I want to give him more control, less control over certain things. It's really interesting to watch that play out. 


 josh
 Yeah. What thing in your childhood that you look back and you're like, man, that's kind of f****d up that you want to change. 


 Jordan
 I mean, my mom and I went to therapy cause she would beat me for a period of time and I probably deserved some of it, but I definitely didn't deserve all of it. 


 josh
 I'll be honest. 


 Jordan
 I was, I mean, I was a smart ass and like truly when they told you being a lawyer was arguing with people while you were right. All of my movies, all of our home videos or me arguing with my parents about me being right. So I definitely want to tweak. I mean, I don't want to hit my kid. So that's part of it. Like I want to tweak how he understands like his value. I think for me it was like, proving I was right. Was how I was able to like reward myself or know that I was good. For him, we really tweak a lot more of it to explain to him, like you have a choice of whatever, what do you want to eat for lunch? Where, where are we going to go? Whatever, like, I'll give you these choices, but then there are other things where it's like, I need to put up the guardrails for you. 


 Jordan
 I don't want you to combat me. Like there are things you can argue with me on, there are things where you can't. 


 josh
 Yeah, yeah. Super cool. Now I, when it comes to, your situation, one of the things, here's how I cope with awkward things, right? Like I ask tough questions and then I, when I was a firefighter medic or when I was dealing with, like PTSD and working with cops and all these, all people about, like with mindset, one of the ways that I've learned to cope, if I ask a tough question and I, I hear something and it makes me feel a little awkward is I'll joke about things, right. It's my coping mechanisms, 


 Jordan
 A great defense mechanisms, 


 josh
 Chariots. So, I want to be very clear that, like beating a kid, bad beating kids bad, right? Like, and going to therapy and unwinding these things good. Right? Like those things. For the story that you had of, what's something that you had experienced, that's tough. Like what I want to uncover from that is, what did you need to unpack in your own life? Cause you said you went to some therapy. What did you learn in that space? What did you learn for you? And now applying it to fatherhood? 


 Jordan
 To my parents credit, like I, my mom and I went through therapy at the time and that's what stopped it wasn't like we had to look back 20 years later. Also. I really like, I don't think that you truly appreciate your parents until you have a kid. Like the sacrifices that my parents made and not being able to give me what I wanted all the time, financially time-wise whatever, because they had to work because they had to, do overtime to make more money, whatever it is. Like, you don't really appreciate that until you are sitting there in the same position. Like, my dad delivered mail and my mom was a meter maid and then a substitute teacher. Like they sacrificed to give me the opportunity to go to law school for then me to hopefully sacrifice. My kid becomes like a plumber or an HVAC instead of going to law school. 


 Jordan
 We'll see. 


 josh
 Yeah, yeah. It, I think it's in our heart to help our kids have a better life than we did. Right. I think that's a natural desire, but things get in the way, finances, energy resources, patients, the kid has a runny nose and coughing or crapping everywhere or coloring on the walls or whatever the case may be. And we lose our s**t. We forget, we want a better life for our kid than we had for ourselves. As I think your mom super brave. I'm super glad that you brought this up of, in the middle of going through the situation you went to therapy to fix it right then and there, my experience was not that I had to do it 20 years later and try to unwind the crap in my life. How old were you ish, when you started going to therapy, like for that, 


 Jordan
 Couldn't tell you, I would say five to seven, somewhere in there. I was pretty young, 


 josh
 Super brave of your mom to do that because you know that it's scary to say that, Hey, you know, I, you know, I don't like the, what I'm doing or I don't like what's going on with my kid. How do I fix this super brief? Do you, what are your thoughts on, as you're now older, have a four year old kid, like, what are your thoughts on coaching and consulting, or maybe not consulting coaching and in therapy and therapists and all that stuff. Like how do you view that now that you're a father? 


 Jordan
 I think it has helped me have truly have a growth mindset. Like I am all about, I am, let me say all about I'm 80% of the way there naturally. Trying to get the other 20% of the way there did that concept of like, sure we have some semblance of talent, but ultimately about that hard work and effort. And then you apply that to everything. Like, if you want to be great at this, you just have to put in more time and more effort and then coaching becomes an easy way for you to get that better explanation therapy becomes a really easy way for you to get that better internally. Like, there's just this whole concept of, we should be doing these things to better people, to have a better impact on those around us to have a better impact on the world as a whole, hopefully for the better and et cetera. 


 Jordan
 I think a lot of that, like I think a lot of that for my childhood could have been a lot different because I was always, I always did. I always did well enough in school to slack off in school and still do well. Like, I think this was the part that helped me overcome the ability to kind of coast at least later in life. 


 josh
 Yeah. So, you have multiple businesses now. Like how do you find balance? How do you find the ability to do the lawyer stuff, the marketing stuff, and then taking the kid with his fake beard to the science center. 


 Jordan
 I, that's a really easy one for me. I only worked two, maybe three days a week. Mondays and Thursdays sometimes Tuesdays, that's it because of, I realized at a very early time in this, to the extent that I'm the one doing work, we are not scalable. I cannot scale myself in my time to the extent that I'm the one marketing that is scalable because I can create content and then pay for the exposure behind it, or I can repurpose it or recreate it or whatever it is along those lines, which I think is why you and I have five so well, because we have that similar mindset. It comes to, if the law firm signs up, 10 clients in a day, it doesn't change for me because everybody else has that stuff assigned. If the marketing company signs up, five clients a week, every week for 10 weeks, it doesn't really change for me because everybody else is handling the fulfillment of it. 


 josh
 Yeah. So, so you brought up a question like you were good enough in school to kind of coast, right? Now here you are in business and would you say you're coasting, would you say that you're striving for something? Would you say the, the metrics that you're measuring is time with kid? Like how do you measure success over here? As you're building out your life and growing and growth mindset and all that, like, how do you measure success? What, what do you measure over here? 


 Jordan
 And another awesome question. So two. 


 josh
 Lunches, there. 


 Jordan
 We go. All right. For me, there is so one, I think you need to split up KPIs metrics. We're going to call them from a personal standpoint and from a business standpoint, I think you always have to be looking at revenue and profit in some manner. So, like we do personal injury, you don't get paid until the end of the case. We have insane cashflow projections going out, six months, nine months, two years, based upon when we think the cases will resolve so that we can make decisions based upon when we think we'll have the money from those cases. From the marketing standpoint, we've got a lot more of a subscription based model. People are paying us every month to do things. It's a lot easier to project current cashflow time by time. You have to look at, are those numbers getting better on the business side? 


 Jordan
 What's important to you on the personal side. I usually break it down into three questions. It's how much do you need to make, not want to make, but need to make for this purpose. You need to make enough to cover your mortgage and put food on the table and, live the lifestyle you want to have. It's how much time do you want to be working? What work are you doing in that time? Or what work do you want to be doing in that time? You look at those three questions, it's a lot easier for you to take the very cold, hard business numbers, and then flip that into the impact on your life. Like for me, my accountant jokes with me all the time, he's like you have the lowest profit margin. I was like, right. Cause I have businesses. I don't have jobs like for lawyers, his other lawyer clients might have a 75% profit margin because they're doing all of the work for me. 


 Jordan
 I might have a 30 or 40% profit margin because I'm working 15, 20 hours a week. I have to hire people to do the work, to fill in that time, to cover for all those things. Also like as much as my beard is gray, it's not angrily gray. 


 josh
 How I know that story has a loophole in it. You said my CPA jokes with me, CPAs do not have a huge sense of humor. 


 Jordan
 Mine does the only one. 


 josh
 For all the CPAs listening. First of all, I'm sorry, I am sorry. I hurt your feelings. Yeah, that's the thing I was like, 


 Jordan
 Along those lines, and that's what I leave. That's what I tell my, well, not tell my kid, but like that's what I talked about. Him being like a plumber HVAC. So, and same thing for CPAs. Imagine if you were at some networking thing, whether it's BNI chamber of commerce, whatever, and there was a super engaging plumber or a super engaging air conditioner tech or a super engaging CPA. I think that person stands out so much more than other industries that don't have that rep. You can really set yourself up for success easier because you're like zigging when everybody else zags. 


 josh
 Yeah. Zigging when everybody else is zagging. If you had to Zig in a different way, like, so let's just say you and I had the ability to go back in time, right before you invested all this money into that plastic piece of card. Right. We could choose a, another potential business path or career path. And don't, let's just say money. Wasn't an issue. You're like, cause you won the lottery or your mom, was doing meter a meter maid. She found a scratch off ticket and won a billion dollars. Right. If you could choose another career before you became a, an attorney and then marketer, like what would you choose? Just. 


 Jordan
 For fun. Probably business. 


 josh
 Yeah. 


 Jordan
 Yeah. 


 josh
 What kind of businesses or business? 


 Jordan
 Well, so my wife and I did Eve Rodsky is an author. It has a book called Fairplay. The concept of the book is like in most families, the wife is responsible for 75% or more of the stuff. And the husband doesn't really acknowledge that. So fair play. They literally give you a flashcards and you divvy them out on who has what? So one of them is unicorn space. It's like by getting the flashcards passed out, you have your unicorn space. I was like, wife, I gotta be honest. Like if you hit a hundred million dollar lawsuit, I think I would still be like 75% of what I do now. Like I genuinely enjoy the setting up businesses. I genuinely joined the content creation, interviewing people, networking, whatever. She was like, yeah, the book talks about that. Like there are people that have business be their unicorn space. 


 Jordan
 At the same time, like, as I was thinking about that, I was like, man, imagine if like you could run a for-profit business without actually having to make a profit. Like if you looked at that extra 20, 40, 60% profit margin and were like, I'm just going to keep reinvesting this. Cause I don't need the money. How much more would you be able to do, would you be able to launch a different business every six months? Would you be able to hire people twice as fast as your competitors? Like it would be this interesting, not overburden under burden of a business. If you didn't actually have to make money, but you wanted to still run the business successfully. 


 josh
 You feel like you're a unicorn right now in terms of like your, even if you hit the, hit it big a hundred million dollar case or whatever, it's still pretty much be doing very similar to what you're doing now. 


 Jordan
 Yeah. I mean, so look, my wife, Kate and I are on a cross country road trip. We've been doing it since October. We come back to Orlando for like two weeks, every couple months were in Hawaii for three weeks last month. Like, I'm totally like, not an Instagram influencer, but like I'm in Hawaii taking a million photos, posting them. And like, we're getting cases from it. Like these are these lawyers like, Hey, I'm a lifestyle brand. Like I've been able to do this cause we've got great marketing. Cause I've got these systems in place, whatever. So yeah. There'd be a component of it where I was like, great. Instead of showing you our Airbnb, that's in a good location and I'll show you are, thousand dollar a night hotel room that we're rocking in. But ultimately that's not my life now. And it's really not my brand. 


 Jordan
 I really liked the working with other, family solo and small firm owners to help them get that same level of success. Totally man, I would just be, I'd be able to influence that much more in a positive way. 


 josh
 That's super cool. Did you get that shirt in Hawaii? You're wearing a Hawaiian looking shirt. 


 Jordan
 Yeah. So I wear Hawaiian shirts pretty frequently. I bought a bunch of Hawaiian shirts. All of them were made in China, but I bought them in Hawaii. I'm sure there's authentic made in Hawaiian shirts. I don't know I was in the wrong place. 


 josh
 Do you think if you and I went to China, we could buy USA shirts is like, say it's like made in the. 


 Jordan
 Totally do the best is they had this whole thing on ESPN or whatever. Like for the super bowl, you've got two teams, will they print all the shirts and hats regardless of who wins. The ones they don't use, they send them to like a third world country. So you could be walking around. I don't even know where it goes. Like there'd be somebody walking out with, oh, the dolphin, the Thanks. Yeah. Just, just kick me in the nuts there. Yeah. Yeah. Somebody like dolphin, world champions, dolphin, undefeated season dolphins made the playoffs. Like that's a shirt that hasn't been. 


 josh
 Dan Marino came out of retirement. 


 Jordan
 Yeah. All that stuff. They're like, it would be so funny. Cause there's gotta be like this entire, third world country subculture that is contingent upon a completely different view of sports. Like, 


 josh
 Is that a parallel universe? Like bird, they actually thought the dolphins won the Superbowl. Or do you think that it's just because they just haven't gone? 


 Jordan
 Well, no, no. It would be like, so the last Superbowl, like obviously the Rams one, they printed shirts for both teams or winning the, at this point, what it's like winning the conference championship, winning the division title. I, there's a shirt for everything. Somewhere out there's the Buffalo bills, four times super bowl, champion shirt floating around when they lost all of them. And I just, it's a crazy concept. 


 josh
 It's a crazy concept. If you could pass on just one characteristic to your kid that you have that you're like, dude, I want my kid to have this. What's that one thing that you're like, my kid will have this, 


 Jordan
 My analytical illness, 


 josh
 My analytical illness is. 


 Jordan
 Analytical illness. Yeah. Like a situation happens and like, this is a totally, maybe this is a different conversation, but ultimately like things just are, we put positive and negative connotations on them at the end. Right? Yeah. From my standpoint, I think I do a really good job. Like at the end of anything, a meal, a movie, a TV show being like, how would I do it differently? What would make it better? What would make it worse? Like the analytical ability dude, if he has that combined with my wife's intelligence, Kiddle rule the world, hopefully nicely. We'll see. 


 josh
 Yeah. All right. Here's an opportunity to get a brownie point for your wife. You already said that she has super high intelligence, right? What is something else? This, you could get some brownie points. What's something else that like your wife has a superpower for. 


 Jordan
 Oh, she's a superpower lawyer. She's the one who oversees the whole legal side. She's a lawyer as well. She oversees the whole legal side of it. Like there is no way that operating a firm would be that much harder without knowing that she's making sure the right stuff happens in all the cases. I hope she would say the same thing about me, it's, it would be harder not knowing that our marketing is done correctly, that our business stuff is lined up. That we're hiring the right people, whatever. But yeah, dude, she is brilliant. 


 josh
 As a superpower, so not to be insensitive, but I study, I studied family trees and when two come together and have a kid that kid's going to be the anti-Christ to lawyers. 


 Jordan
 I funny story. Last summer, before we leave on our road trip, we take swimming lessons or my kid, we put my kid in swimming lessons. So because. 


 josh
 You know how to swim, I assume. 


 Jordan
 I hope so. I wasn't going to my whole life. We put them in swimming lessons and my wife posts like to her lawyer, community, Hey, other swimming lessons, we're doing swimming lessons, whatever at the local pool. So there's another kid who jumps in. You have like six kids in the class. Two of them are the child of two attorneys for both of the kids. One of the kids refuses to get in the pool. They start creating a chant that gets the other five kids in it yet in the pool, get in the pool. Like they're bossing around the, 18 year old giving the swimming lessons. Like you could immediately tell who the two lawyer, parent kids were. And it was so funny. Cause like I never realized it because most of our friends are lawyers or they're doctors or, they're in a similar area, but just like putting them in this regular swimming lesson, I was like, I can tell you whose parents are you for living with the way these kids are figuring out how to pull one over on the 18 year old swimming instructor. 


 Jordan
 Yeah. 


 josh
 Yeah. What do arguments look like between husband and wife where you both are attorneys? How does that work out for you? 


 Jordan
 Another great question, which. 


 josh
 Is, 


 Jordan
 My wife had the ultimate, this was a yesterday two days ago. I don't know. She's like, it's so funny. She's like, you usually take the path of most resistance. I was like, yeah, that sounds right. She's like, but I think it's because you don't like you don't litigate for a living anymore. You don't argue with people every day for a living. She's like, for me, I'm arguing with adjusters and opposing counsels all day. Like when it gets time to, come home or do something, I want the path of least resistance. I was like, I think so I think you're right. Thankfully like, look, it's not between her and I, it's just funny, like she'll overhear me on phone calls or like, she'll see some email where I'm like, oh, I already have this already have that going on, whatever. She was like, you could have handled that so much easier. 


 Jordan
 I was like, yeah, but like it's important. You know, like I value my time. I value their time. I value this. We don't, we don't really argue that much. I think driving across country in a car for seven months is like all the couples therapy that we could take in a good way. It's very funny to see, like to the extent that we disagree, my wife will usually defer if I think it's important enough because ultimately on everything else, I'm like, you're way smarter than me. Like you're right. I don't care. Like we're just going to do it your way. 


 josh
 Super cool. Your strategy for winning arguments with your wife is let her get worn out during the day, arguing with other people. She comes home and that's when you drop it on her. That's how you win. 


 Jordan
 If that's what you took away. No, I honestly I think the most important line when it comes to inner family conflict is do you want to die on this hill? 


 josh
 Right. 


 Jordan
 There, and 99% of the time, I don't want to die on that hill. It is not that important. Because of that on the 1% of time that it is my wife's like, oh, you're like, actually like you're back in this. All right. No problem. And like it works out so well. Yeah. To have that concept of just like this, actually this, most things aren't important and shouldn't be important. It is like getting that understanding out of your significant other, your parents, your kid, your boss, I don't care, whatever the relationship is become super strong. 


 josh
 You know, what's funny about this. Is this a battle? This a hill I want to die on? I just remember a fight that my wife and I, Anna, so we've bickered and such. We never we've had two or three blowout fights where it's just like, someone should probably call the cops or one of us needs to walk away like immediately. Right. We were in this situation and I remember she like, she jabbed me. It was like a verbal jab of something. I'm sitting there, I'm like, were arguing about something dumb, like dinner or something like, do we want to use paper plates or blasting? It doesn't matter. Right. It was, it was so insignificant. I remember cause she, she kinda like jabbed. I just had a weird day where I kind of felt feisty. Like, I don't know if you ever feel this way. What went through my head is, do I want to die on this hill or not? 


 josh
 And I was just like, yup. It turned into a flight. I was just like, it was worth it. You know? Like, so I don't know if that ever happened to you, but most of the time I'm learning to go. I don't care. Who's right or wrong. I'd rather be happy than right. I go, all right, babe, sorry, love you. I'll go crack a beer or something like that. Like go punch a punching bag. But a, 


 Jordan
 How many fights are actually about what you're fighting about? Like, that's the thing that people decided, like in that moment it's like, okay, paper or plastic plates in that moment, she has that job. You're like, yeah, well, six months ago you did this. And that was so s****y. Like, it has nothing to do with the plates. You know, you've just been simmering. If you let it go, I think, yeah, exactly. Like you're happier and the relationship's happier and your kids see happier parents and they become happier people. Like, it just snowballs in a good way. Dovetails. I don't know, whatever the word is there. 


 josh
 Yeah. Let's use snowball because we're both in Florida and we really understand what snow is. What does that thing behind you? I'm looking at like, is that a picture. 


 Jordan
 It is a painting. I was on a cruise in Jamaica, Dominican Republic one of the cruise ship replied guys. The guy was like, literally finishing, painting this. And I had that moment. You watch parks and rec. 


 josh
 I I've seen like one episode. 


 Jordan
 All right. There's a character in there who like, they commissioned some art and he's like, this is the only piece of art that has spoken to me like this was it. If I zoom up it basically it's like the statue of Liberty in the middle. It's a heart, it's got an American flag done in the way of this German artist who did the like 2006 Olympics. I was like, this is the only piece of art that speaks to me. Like, I must buy it from you. And of course he's selling it. I was like, what? How much is it? He gave me a price that was way less than I would have paid. And I was like done sold here. It is. 


 josh
 Swipe, swipe your bar card. 


 Jordan
 Yeah. Like to this day, it's like, literally the only if you look at the rest of my office, I have action figures over there. I've got a whiteboard over here like that. And I've got diplomas. Like, this is the only piece of real art that is in my office. 


 josh
 For, most people are just listening in, but we're going to start sharing this on YouTube. Could you zoom out? So I could see that. Are you able to do that or is it going to screw up your cameras and everything? 


 Jordan
 It's going to screw up my camera. I can lean over weirdly. Okay. 


 josh
 Cause it kind of all right. I, it, I thought it was like a leg. All right. You'll have to, maybe you get snap a picture of it or something like that. 


 Jordan
 All right. 


 josh
 Cool. For the people just listening in, you're just not gonna get the full experience of what they're experiencing. Jordan, as you're building out fatherhood, as you're building your kid, right. You're helping them, grow he's four years old. Now, any future kids come in, you. 


 Jordan
 Think, I don't think so. 


 josh
 Done. Done. 


 Jordan
 Skill. See, I don't think so. 


 josh
 Yeah. I got neutered last year or 2020. No more kids from this, from this tree, from this. 


 Jordan
 A good time. Good time to do it. 


 josh
 Yeah. Good time to do it. Right. Where everybody's locked inside and quarantined and all that. I was like, if I don't get this thing tied in a knot, we're going to pop out more kids. So yeah, just three for the Wilson's. So you got, you got this kid. What's your favorite thing about your son? 


 Jordan
 His personality. And, and there are those moments like to go back to kind of the fight, then there are those moments where he says s**t, that is like, it should bother me. It's so funny coming from him like yesterday, this is a great yesterday. My wife makes him a breakfast. I don't remember what it was. Pancakes, oatmeal, whatever. But she has the audacity. I'm putting that in quotes, the audacity to put the strawberries on the same plate as the other food. 


 josh
 What was she thinking? 


 Jordan
 Right. Well, so my child definitively and I quote says, mommy, why do you always make me so mad. In like full, complete sentence? Like the whole thing about his job. He wanted the strawberries. He wanted them on their own plate. And like she should know better. It was one of those moments where I was like, this kid is being a Bret, but man, is it funny? Like it is just so like, that is the hyper-technical loyalness that you get out of a four year old raised by two lawyers. Like how dare you put it on the same plate. You always, mommy, why do you always make me so mad? And like, you have to laugh. Like you have to laugh in those moments. That is so totally to go back to this personality. It just cracks me up. Stuff like that. 


 josh
 Yeah. Do you have any good attorney go-to jokes? Like, cause you work with attorneys all day long. You're your own firms and you do marketing for hundreds of them. Like, do you have any go-to attorney jokes? 


 Jordan
 Yeah. If you follow me on Instagram, literally I post intentionally bad. Dad jokes are all attorney based. Perfect. For this one, I will give you the only positive attorney joke in the entire world that I'm aware of. There may be more, this is my only one. Guys walking on the beach and of course he sees the magic lamp, rubs it and out pops a genie says, I'll grant your normal three wishes. He goes, all right, number one, get rid of all the lawyers. Jeannie goes, poof, they're done and have a great day. The guy goes, well, what about my two other wishes? The genie goes, you can't Sue me. 


 josh
 It was good. 


 Jordan
 That is the only positive layer joke that I'm aware of. All the rest are at our, to our detriment. 


 josh
 Yeah. 


 josh
 Perfect. 


 josh
 Perfect. 


 josh
 Perfect. 


 josh
 Perfect. All right. Jordan, a few things as we kind of near the end, I got this deck of cards with a bunch of questions on it because my brain doesn't come up with the most creative questions in the world. So tell me when to stop. I'll ask you one of them. 


 Jordan
 Stop. 


 josh
 All right. There's some questions, not in this deck, but I'm going to buy, there's a, a deck that is a lot more uncensored and it's the what's that cards for humanity. It's one of their lines. I think I'm going to buy that for the, for this show specifically, but for this question, do you believe chemistry is inherent or is it something you could develop over time? 


 Jordan
 See, I would be a hypocrite. If I said it is inherent. If I'm talking about growth mindset, 


 josh
 Boom. This was like the specific card for you. 


 Jordan
 Was meant to be. If. 


 josh
 You don't have a growth mindset, let's just say, there's the guy that's moon. Or for me, and we're like, maybe you're, I'm just stuck. Right. I need to expand my mind and my mindset. What's what's some advice do you have for me on how to grow mindset, growth mindset? 


 Jordan
 That's a tough one, man. We're racking up lunches here. No, I'm. 


 josh
 Love lunch. 


 Jordan
 The thing for me is there while on it at first glance. So it's growth versus fixed mindset. The fixed mindset seems safer, right? Like I have natural talents. I'm good at these things and I don't have to work hard for them. The problem with that becomes then you have to actively avoid every opportunity to be proven wrong. If you are the best at math, you have to actively avoid being better at math, for fear of hitting your cap. I always look at like growth mindset is an excuse to f**k up a bunch in the betterment of your future. Getting better at this, getting smarter at this, getting faster at this, whatever it looks like along those lines or the flip side of that. If you really enjoy something that you were terrible at, it gives the opportunity to truly believe you can be good enough at singing, playing music, Frisbee, whatever it is that you see enjoyment in, but are currently terrible at, like, it really gives you the, a better opportunity to see a brighter future. 


 josh
 Super cool. What are you terrible at that you really enjoy besides just sex? Oh, just man. 


 Jordan
 That's that's two sex jokes, 


 josh
 Two sex jokes shot. I love it. 


 Jordan
 What am I terrible at that? I really enjoy probably singing. Like I have a pretty bad singing voice, but I don't. I like singing in the car or the shower or whatnot. Yeah. I do have that also on I've posted that on social. I got my kid to do sweet Caroline at like three years old doing the Baba. I thought it was so funny, even though I'm rocking my terrible singing voice. The flip side of that is I am aware of how terrible I am at most things, which makes me a better business owner because I don't try and stick my fingers in everything. 


 josh
 Yeah. That's good. Especially electric sockets don't stick your fingers in those. Correct. If I looked at your playlist besides, Tom Jones right there, and we're looking through and we're scrolling through what's a song that if I played right now, you would probably want to bust out and sing. 


 Jordan
 Neil diamond, man, not. 


 josh
 Neil diamond. I'm sorry. Sweet Caroline Jones. 


 Jordan
 Pop on by. 


 josh
 Someone just unsubscribes because of that. They're so like offended. 


 Jordan
 There we go. They can, now you can follow me on, I don't know, less interesting shows because I got it. Right. 


 josh
 Leave my show and go to Jordan's. 


 Jordan
 There we go. What else will be on my playlist? 


 josh
 Yeah. That you're going to sing to. 


 Jordan
 Oh, then I'm going to sing too. 


 josh
 Yeah. 


 Jordan
 Ooh. That's a tough one because I would say sing on my playlist. I dunno. Barenaked ladies songs. Most of those pretty good. Easy to sing in public. There's definitely a series of like nineties rap music that I would love to sing, but I'd be so concerned about saying the wrong words that like the Superbowl halftime show, there were so many of the songs I was like, what are they saying? I looked it up and like, that's the clean lyrics? They like learn this whole different version of the song to play versus what I know from the album. So like that I won't do. 


 josh
 What's your favorite nineties hip hop band or not band because they're hip hop. They don't call themselves band crew. 


 Jordan
 Person. Artists. 


 josh
 Are artists. Yeah. Group. 


 Jordan
 Probably Jay Z. 


 josh
 Okay. 


 Jordan
 Is that dirt off your shoulders? I think it's great. 


 josh
 That that's your jam? 


 Jordan
 A bunch of other ones. Yeah. 


 josh
 Do you do the dance when you do it? You're like good. 


 Jordan
 As a very, as a very white Jewish person. Yes. Like understanding I'm a white Jewish person while doing it. Yes. Yeah. 


 josh
 Have you seen Tropic thunder? 


 Jordan
 Yes. 


 josh
 With fill GRAsping, I think is where Tom cruise plays a Jewish guy and he dances to hip hop. Have you seen that scene? 


 Jordan
 It's I mean, I've seen the movie, but I it's been awhile. I'll have to rewatch the same. 


 josh
 Yeah. You need to watch like the ending credits with Tom cruise. He's filled. 


 Jordan
 I think it's in like an 80 pound fat suit, right? Yeah. 


 josh
 Yeah. And he's dancing. He's jamming out. Like he does a great job. Tom, when you're listening to this, props for your dance moves as a Jew old vet Jewish guy. 


 Jordan
 There we. 


 josh
 Go. Yeah. That's perfect. Jordan. Let's do this, man. What questions should I have asked you that I screwed up? And didn't ask you during this interview. 


 Jordan
 I don't know, man. I like the cards. I like the idea of like, let's let fate pick some of these questions. 


 josh
 Yeah. 


 Jordan
 What questions did you not ask? I don't know, man. That's that's nothing stands out. 


 josh
 Cool. Where could guys go? If they're like, man, I really liked Jordan's vibe and I want to connect with him. What's a good place for them to connect with you and maybe even just go, Hey man, could you get on my show? Or could I, could we chat or something like where it's a good place for them to connect with you? 


 Jordan
 Sure. If you are looking for slightly more business, bitterly, sarcastic Jordan, LinkedIn, there's two Jordan OSS drops the other. One's a sales person in Boston. Screw. 


 josh
 That guy. 


 Jordan
 No, you know what? Listen, dude, he gets a lot of job offers email to me. He's doing something right. I'm very proud of him. And I wish him the best. He's the second best Jordan Ostroff, but all, but he's really he's nipping at my coattails. Or if you really want the like goofy dad version of me, Instagram is probably the place I am a lawyer with a life and on Instagram. 


 josh
 And, and, and your kid has one, it's two, my two attorney parents or something like that. Right. 


 Jordan
 Perfect future. A-hole. 


 josh
 Perfect. Well, George, thanks for being on the show. Dudes as always reach out to our guests, say, thanks for being on the show. If what they're saying resonates with connect with them, all their contact information will be in the show notes. If you guys are working on something in your mind, growth mindset or struggle that you're working on and you need some help head on over to uncensored advice for men, there's a form you can fill out and I could connect you in with a past guest or a coach or someone who could maybe help you walk through a situation. This the purpose of this show is to help us dudes talk about things that are uncensored from porn stars to pastors, new tagline. We've had Jordan helped me with that one. We've had a, a lot of conversations with people who care about you guys, so you're not alone. 


 josh
 If you need something, reach out. If you'd like to be on the show, same thing, uncensored advice from men.com, fill out a form and maybe get you on the show next till then talk to you all next episode. See you guys. 

Jordan Ostroff Profile Photo

Jordan Ostroff

Jordan Ostroff is a visionary entrepreneur, President of LegalEase Marketing, Managing Partner of Jordan Law Fl, Host of multiple facebook live show and the Chair of Big Brothers Big Sisters of Central Florida.

From a young age, he knew that he wanted to be a lawyer - even when he had no idea what that meant. During college, he began competing in trial competitions across the country, where he was an award winning advocate for fictitious cases.

After law school, he started his legal career as a Prosecutor for the State Attorney's Office. There he cut his teeth in the trenches and learned how to truly be a “real” lawyer.

Today, he manages Jordan Law FL, a firm focused on personal injury and helping injured victims get the recoveries they deserve. His firm utilizes the latest technology and automation to provide top level legal work, with a low volume of cases but a high touch level of care and compassion. The son of a postal employee and a substitute teacher, he is the first lawyer in his family, and with no business experience his first few years of running a firm were incredibly difficult.

He was consistently taken advantage of by other marketing companies, because he didn’t get it and didn’t know what to ask for or what to look for. Having been faced with the prospect of learning how to run a successful business or close his firm and file for bankruptcy, he choose the later. Now Jordan works 3 days a week, usually 20-25 hour each week.

This new path culminated in Jordan starting LegalEase Marketing, a holistic lawyer focused fractional CMO company. Part full service marketing company, part consulting firm - Jordan shares all of the info that he wish he knew when he started his firm and focuses on helping other lawyers not make the 1,000,000s of mistakes he’s made. LegalEase prides itself on treating its clients the same way those lawyers treat their clients - they come first, they own their "file," no conflicts of interest, etc.

Additionally, Jordan is the host of Exhibit A(ttorneys) a live show where he interviews lawyers and experts on how to build the best lawfirms and be happy as a lawyer. He also hosts The O Know Show, where he interviews people about the cool things going on in Central Florida, as well as the Chair of his local Big Brothers Big Sisters chapter a non-profit that pairs hundreds of underserved children with professionals who mentor them for most of their lives and help them achieve success.