Jordan Ostroff

Jordan Ostroff, Esq (00:01)
What’s the opposite of culminate? Like what is it? We hit rock bottom when my wife told me she was pregnant with our child. And thankfully I was happy. That’s not the problem. The problem was 10 seconds after that, me realizing like we are $200,000 in debt. We are working 80 hours a week. We are both miserable. And now like somebody’s going to hand us a baby on the dumpster fire that is our life.

Kevin Daisey (00:24)
What’s up everybody. It’s Kevin Daisy with the Managing Partners podcast. And I’m here today with a good friend of mine, Jordan. And he’s got some cool stuff to share today. He’s going to, we’re going to be talking about how you can have a better life, run a better firm and do it in less time and not be as stressed. So we can all use a little bit of that. So Jordan, thanks so much for joining me. Jordan’s actually out of Florida, Orlando.

and he has a PI firm. But Jordan, please say hi and introduce yourself and tell us a little bit about your background.

Jordan Ostroff, Esq (01:02)
Sure, Kevin, thanks so much for having me. I knew I wanted to be a lawyer for as long as I can remember. Having no idea what that means, and some days I still don’t, but my family will tell you I argued with them a ton as a kid, so that prepared me for at least parts of it. When I graduated law school, I started out as a state attorney and then ended up opening up my own firm, originally doing criminal defense with my wife, who is also a lawyer and a way better lawyer than me.

What’s the opposite of culminate? Like what is it? We hit rock bottom when my wife told me she was pregnant with our child. And thankfully I was happy. That’s not the problem. The problem was 10 seconds after that, me realizing like we are $200,000 in debt. We are working 80 hours a week. We are both miserable. And now like somebody’s going to hand us a baby on the dumpster fire that is our life.

so from that, you know, mid 2017, took my firm back down to the studs, recreated it from scratch and something that we actually wanted.

which culminated in us taking a 13 month cross country road trip in 2021 and 2022 while the firm did great. So PI firm had a marketing company for lawyers that in that meantime got bought out from that. So now I’m doing coaching to try and help more lawyers create their version of my life. In essence, how do you own a business that you can be proud of and live a life that’s even better?

Kevin Daisey (02:21)
I love it. mean, it’s, you know, we don’t have much time, so there’s no need to, to waste all of it. Just working your butt off every day. So, and then it’s funny how a kid or a child will, kick things into gear for you, right? Real quick. Yeah. Like I’m responsible for someone else and their life. Okay. Let’s, let’s figure this out. So big moment for you, I assume.

Jordan Ostroff, Esq (02:38)
yeah.

very much so. And it’s interesting because like now I want to be very clear on how I’m about to phrase this. Like I view my employees like my child very similarly. Not that I treat any of them like children, but like there’s that weird balance where you’re like, hey, I want the best for you, but I also want to push you to be better. But I also want to give you the opportunity to fail and learn. And so it’s amazing to me how much being a parent has changed me as a boss and a leader and a person and hopefully for the better.

Knock on wood.

Kevin Daisey (03:21)
We’ll be we’ll judge that here after this podcast no No, it really does. I mean I have two kids and actually as you’re recording this My daughter’s turning 11 today. So it’s her birthday and I’ll be home after another meeting or so after this I’m gonna be home early and we’ll be going dinner and all that good stuff. So

Jordan Ostroff, Esq (03:24)
There we go.

Hey, happy birthday.

Please tell me your daughter is daisy daisy.

Kevin Daisey (03:44)
It’s Arden Daisy, but no. Yeah, no, she’s the girl and she probably gets praise for her last name. Being a guy, I don’t know, but it worked out for me. No problems. I would say, well, it’s like the BB gun company, Daisy. I don’t know. Or the sour cream, could be that too. Neither one of those are my family’s.

Jordan Ostroff, Esq (03:59)
Totally.

You know, Ostroff is nothing. So.

Kevin Daisey (04:13)
Neither one of those brands were my family, so I have to run my own firm. anyway, I didn’t get lucky enough for that.

So Jordan, let’s kind of get into what you do. I love your style and the firm. love, if you go check out Jordan’s website for his coaching side of things, his logo is awesome. He’s like laying in a hammock across the scales of justice. And I just love everything about it. He’s always wearing a Hawaiian shirt, just chill. And so he’s living the life he wants to live. I’m just excited for you to kind of share some practical, you know.

Jordan Ostroff, Esq (04:35)
Thanks, man.

Kevin Daisey (04:52)
tips for our audience today. Obviously a lot of lawyers out there listening in. so what’s the best place for someone listening that’s just running around like crazy, they’re trying to grow their firm, to step back a little bit and say, all right, is this really what I want? And am I living the life that I want to live?

Jordan Ostroff, Esq (05:13)
Yeah, I mean, okay, so here’s the thing for me. Somebody explained this to me the other day that when it comes to nonfiction books, it is Stephen Covey on one side and Malcolm Gladwell on the other. And so like anything by Stephen Covey is so tactical. Do this, do this, this organization structure this. Whereas Malcolm Gladwell is just like, let me spin you the most wonderful story and you will learn something, you will take something from it inside. And so I think we kind of need to start with that.

because ultimately I think the first step is the Malcolm Gladwell story. You need to understand that you are not writing the story of your life that you want before we can get into the Stephen Covey, these are the tactics for it. So mindset, woo woo, whatever you wanna call it, that’s the part where this begins. Ideally it’s not knowing you’re gonna have a child and realizing that’s the rude awakening of your life is awful. Hopefully it’s more proactive, but.

Kevin Daisey (06:01)
Love it.

Jordan Ostroff, Esq (06:10)
Whatever works, whatever it takes, I’m here for you to have that moment of clarity that something drastic needs to change.

Kevin Daisey (06:20)
I appreciate that explanation. think that that makes a lot of sense. we want to kind of always go into tactical, you know, mode and what can I get from step one, two, three, four, and how can I go apply that? And the reality is most people don’t even go apply that you get a conference, you learn all this stuff, and then you come back and you do any of it. to your point, I mean, those moments in time, like you had, like, it was like, boom, change has to happen. Right.

I had a young attorney on this show a couple of years ago and she was a solo and didn’t delegate, didn’t hire people, didn’t have processes, you know, just kind of running, running, running. And then she got COVID and was in the hospital for two or three weeks. Literally trying to work in her hotel, like can’t barely breathe and working because she had no choice. Like knowing no bills are paid if she didn’t get the work done. So that was a root.

Jordan Ostroff, Esq (07:03)
No.

which sadly is a high performing LinkedIn post, right? Like the things that I learned working from my death bed, now trending on LinkedIn.

Kevin Daisey (07:23)
Yeah. So she was like, can I come back on the show and talk about basically what I learned from that experience and, what she knows can’t happen again. You know, so she has to build a team around her. She’s got to delegate. She’s got to, you know, build those things up. And a lot of lawyers that I meet, especially the solos, they’re, they’re prescribed to, I got a case. I work it. the money’s good. And then just stay in that, you know, constant and just.

never escape it.

Jordan Ostroff, Esq (07:54)
Totally. So let’s get people out of that. Because I don’t want you, God forbid you are in the hospital for two or three weeks period, let alone it being doubly worse when you can’t have your firm pause. I’m just, that is sad and unfortunately common, at least to some extent, maybe not hospital bed size, but like it is.

crazy to me, the amount of lawyers that will say they took vacation and then brought a laptop and worked four hours a day on vacation or six hours a day or whatever and didn’t have the right moments. And then you’re modeling that for your family and your kids. Like there is no break from all this stuff. So let’s break the chain now.

Kevin Daisey (08:35)
Yeah, sure.

What’s, you know, everyone listening, like, you know, what’s, what’s something that would, have them think about those moments or, you know,

Jordan Ostroff, Esq (08:48)
Yeah. So I, there’s three questions I have all my clients go through and I look at it as like, I don’t know if you’re like me, I can’t tell you the last time I got in my car and did not set my phone to a location, right? Like I’m not just driving around randomly. ha so, but with a business we don’t we’re like, I’m running this business and I don’t know, like more, more cases, more rev, whatever. So like, let’s get our GPS set on what we want. And that is how much money do I need to make me personally? How much money do I need to make?

So if you are a 20 % profitable firm, you need $200,000, the firm has to make a million dollars so that you have the 200,000. Then, when do you want to be working? If your answer is never, I’m fine with that. We can work around that. If your answer is 10 to three while my kid’s in school, great, we can work around that. If your answer is Monday through Thursday, because you want to take every Friday off, great, we can work around that. And then third is what work do you actually want to be doing?

And I think ultimately from a law firm owner standpoint, you can be the business owner. You can be the lead salesperson. You can be the head marketer. You can be the lawyer or some combination of those things, but really like giving your answer to those three questions. And now we have our coordinates set and it becomes, how do we get there? And when you’re stuck on a decision, does that decision get me closer to my questions or not? And obviously sometimes you’re going to sacrifice. Like you might hire another lawyer, which will

impact the money a little bit, but will really free up the time. So it becomes a balancing test. But without those three questions, I don’t think anybody has any idea what success really looks like for their business. And this really helps us figure that part out because we need to do that first so that we then have the bandwidth, flexibility and finances to live a great life, which ultimately ends up helping our business as well. At least I have found and my clients have found.

Kevin Daisey (10:41)
Those are fabulous questions. It’s very simple. You’re making it really simple because I’m just thinking about them, you know, as you’re asking them. And yeah, it’s different for everyone, right? You I’ve had people on this show, a lot of friends I know that they’re CEOs, they run their op, they’re firms. They don’t even practice law, really. They decided, you know what? I like the business side better. That’s what I want to do. Your wife loves being a lawyer, right?

so she’s yeah.

Jordan Ostroff, Esq (11:12)
My wife is a legal scholar in every sense.

Kevin Daisey (11:17)
Yeah. So I was listening to Jordan on a recent podcast with Answering Legal, a good friend of mine, and we use their call service. And yeah, he wanted to do business operations and marketing and that. so you go and learn about that stuff where your wife wants to be the best lawyer and goes to conferences and stuff to learn about trial and how to be a better lawyer.

versus them both trying to be the best lawyer and be marketing and all these other things. And you’re just overwhelming yourself with, with too many hats. So I think that’s really good to figure out.

Jordan Ostroff, Esq (11:57)
Yeah, I mean, that’s my issue is you have so many lawyers that are beating themselves up. They’re like, I’m not good at any of these things. But if you sat down, they’re like, they have a 40 hour a week caseload. They have a 10 hour a week business development thing. They have a 20 hour a week marketing job. They have a 15 hour a week sales job. And they’re trying to cram that into even 60 hours. Like you’re taking four full time jobs and trying to make it one and a half time like

God bless you, but also like don’t beat yourself up that you’re doing a poor job because you don’t have the time to do a good, to do four good jobs. Like that is not a thing that we are capable of as humans. So let’s, let’s remove the guilt.

Kevin Daisey (12:35)
Yeah. you know, and maybe, maybe you’re not the best lawyer. Maybe your lawyers you’ve hired are better than you and that’s okay. Don’t, you don’t have to be the best lawyer to run a great law firm and to help people. Right. You can just be the marketer in your firm. doesn’t matter. I just came back from a conference and you know, there’s a lot of like social media breakout sessions like, and everyone’s like, well now I gotta, now I gotta be a social media influencer. And so that’s, they’re like trying to figure out how they’re going to do that. And it’s like,

Well, you don’t have to do that. And you can also hire people to do that. You know, you doesn’t have to be something you take on. and so I think there’s a lot thrown at these lawyers that like, I got to do this. I can do that. I’m not marketing over here. You know, so, my intake sucks. And now I to focus on that, you know, so there’s a lot that has to be done in the business. You know, there’s so many parts that have to be focused on. And I think maybe that’s the key word.

focused on, right? So you can’t focus on all of it because you’re not focused. You’re trying to do everything. So good question, I think is like, what do you want to do? What kind of work do you want to do? What do you enjoy doing?

Jordan Ostroff, Esq (13:48)
Yeah. And look, I don’t care what the answer is. I care that you figure out your answer or, you know, we figure out the answer together and then we work towards it. You know, if you want a full caseload, great. Let’s get you the support you need to be the actual lawyer. If you want to be like me and go get lunch and play golf with friends who quote unquote, networking referral sources. Great. We can set that up while there’s, you know, a lawyer and a staff and whatnot in the office. You know, like I don’t care what the answer is. just.

want to give you the opportunity to achieve it instead of having 27 plates spinning above you and being aggravated when one of them falls and breaks.

Kevin Daisey (14:25)
Yeah, one of the, is a quote I saw recently at a presentation, but it was like, know, you know, working hard, doing something you don’t like is called stress and working hard, doing something you love is passion, right? So I think too, like, you, you know, I read your stuff and listened to some stuff like, you know, three days a week or I’ve, you know, four days a week and just.

You’re cutting back your time and your work, but some people might be like, you know what? I’m fine with five days a week 40 hours a week because I love doing what I want to do and That’s fine. But still be able to take off on the weekends take off on longer trips be able to Step back and if you’re passionate about being there five days a week, that’s I guess that’s fine, right? This like you said, it doesn’t matter what the answer is But are you doing that right?

Jordan Ostroff, Esq (15:19)
Yeah. And look, it might change. Your answer might change. Great. Then make the changes to get to where you want to be. But I just, you you read every amazing memoir of every super successful person and all of them are like, I should have spent more time with my family. I should have spent more time with myself. I, if people knew what I went through, nobody would actually want to be me. And then we have this whole like hustle porn culture that is like, if you’re not working 16 hours a day, like somebody is catching up to you. Like, yeah, until they die at 40.

something stress related or lack of sleep or whatever else. Stay in the game by taking care of yourself, which allows you more time to take care of others, whether it’s a spouse, whether it’s kids, whether it’s employees, whether it’s clients.

Kevin Daisey (15:51)
EEEH!

Jordan Ostroff, Esq (16:04)
These attorneys who are burning the midnight oil, I don’t think are actually doing right by their clients because they’re burned out.

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Kevin Daisey (17:33)
So Jordan, let’s kind of get into what you do. I love your style and the firm. love, if you go check out Jordan’s website for his coaching side of things, his logo is awesome. He’s like laying in a hammock across the scales of justice. And I just love everything about it. He’s always wearing a Hawaiian shirt, just chill. And so he’s living the life he wants to live. I’m just excited for you to kind of share some practical, you know.

Jordan Ostroff, Esq (17:47)
Thanks, man.

Kevin Daisey (18:04)
tips for our audience today. Obviously a lot of lawyers out there listening in. so what’s the best place for someone listening that’s just running around like crazy, they’re trying to grow their firm, to step back a little bit and say, all right, is this really what I want? And am I living the life that I want to live?

Jordan Ostroff, Esq (18:25)
Yeah, I mean, okay, so here’s the thing for me. Somebody explained this to me the other day that when it comes to nonfiction books, it is Stephen Covey on one side and Malcolm Gladwell on the other. And so like anything by Stephen Covey is so tactical. Do this, do this, this organization structure this. Whereas Malcolm Gladwell is just like, let me spin you the most wonderful story and you will learn something, you will take something from it inside. And so I think we kind of need to start with that.

because ultimately I think the first step is the Malcolm Gladwell story. You need to understand that you are not writing the story of your life that you want before we can get into the Stephen Covey, these are the tactics for it. So mindset, woo woo, whatever you wanna call it, that’s the part where this begins. Ideally it’s not knowing you’re gonna have a child and realizing that’s the rude awakening of your life is awful. Hopefully it’s more proactive, but.

Kevin Daisey (19:13)
Love it.

Jordan Ostroff, Esq (19:22)
Whatever works, whatever it takes, I’m here for you to have that moment of clarity that something drastic needs to change.

Kevin Daisey (19:32)
I appreciate that explanation. think that that makes a lot of sense. we want to kind of always go into tactical, you know, mode and what can I get from step one, two, three, four, and how can I go apply that? And the reality is most people don’t even go apply that you get a conference, you learn all this stuff, and then you come back and you do any of it. so I, to your point, I mean, those moments in time, like you had, like, it was like, boom, change has to happen. Right.

I had a young attorney on this show a couple of years ago and she was a solo and didn’t delegate, didn’t hire people, didn’t have processes, you know, just kind of running, running, running. And then she got COVID and was in the hospital for two or three weeks. Literally trying to work in her hotel, like can’t barely breathe and working because she had no choice. Like knowing no bills are paid if she didn’t get the work done. So that was a root.

Jordan Ostroff, Esq (20:17)
No.

which sadly is a high performing LinkedIn post, right? Like the things that I learned working from my death bed, now trending on LinkedIn.

Kevin Daisey (20:36)
Yeah. So she was like, can I come back on the show and talk about basically what I learned from that experience and, what she knows can’t happen again. You know, so she has to build a team around her. She’s got to delegate. She’s got to, you know, build those things up. And a lot of lawyers that I meet, especially the solos, they’re, they’re prescribed to, Hey, I got a case. I work it. the money’s good. And then just stay in that, you know, constant and just.

never escape it.

Jordan Ostroff, Esq (21:09)
Totally. So let’s get people out of that. Because I don’t want you, God forbid you are in the hospital for two or three weeks period, let alone it being doubly worse when you can’t have your firm pause. I’m just, that is sad and unfortunately common, at least to some extent, maybe not hospital bed size, but like it is.

Kevin Daisey (21:33)
Yeah. Yeah. You’re burnt. Yeah. You’re, you’re tired. You’re burnt out. You’re going to make mistakes. You’re, you’re less efficient. Right. So, yeah. Focus. Yeah. So let’s, let’s kind of go through these questions. So one at a time real quick again, just so that, know, it’s fresh on people’s minds. So, go through the questions again and then we’ll kind of like hit on each one real quick and then, you know, we’ll kind of pull it all together, I guess.

Jordan Ostroff, Esq (22:00)
Sure, how much money do you need to make? When do you want to be working? What work do you want to be doing? And specifically need want want. Like money, I am concerned about your need. Everything else I’m concerned about your want because we have to hit that need number first. I don’t understand the concept of like mortgage your house to go do something when you have a family. So like let’s hit the need and then we’ll build the wants.

Kevin Daisey (22:27)
Yeah, I love that. yeah, so mean, it’s really like you’re you’re back engineering it. You’re creating a blueprint, right? So yeah, I need to make this much. Cool. How do we do that? Where are we right now? Right. Is the firm profitable enough? Maybe it’s doing a million or two million, but there’s no profit there. You know, that’s a big, you know, the pay has got to be what it’s got to be, what you’re used to, but then what you’re you know, what you’re wanting, what your goals are.

I still think the work you want to do is a big one, especially so let’s think if there’s an attorney listener right now, they’re like, okay, yeah, I want to do this, but I’m doing all this stuff right now. And like, and I talked to a lot of solos, especially that are like, I think it’s kind of hard to see kind of like the other side. like, they’re just doing so many different things. They haven’t hired many people yet. They’re, they don’t trust anyone yet. They’re not delegating. I think it’s harder for someone like that to

to kind of see the light at the end of the tunnel, if you will. So what would be maybe some good advice for someone like that?

Jordan Ostroff, Esq (23:38)
Yeah, well, I mean, so the interesting thing is like figuring out what motivates you. Each person is going to have individual things. So like the easy answer is, hey, if your hourly rate is 250 an hour and you are doing e-filing that somebody could do for 10 bucks, it’s not that you’re saving $10. You’re actually cautioning yourself $240 for every hour that you file instead of bill it. I mean, so that’s one argument. The second point is like if you are sitting here on on your deathbed from COVID, are you really going to be thinking?

Man, I’m so glad I did all the e-filing myself. Man, I’m so glad I updated my own website. Man, I’m so like, is this gonna impact you? Don’t get me wrong, 99 % of decisions were never gonna impact me on my deathbed. But over time, you start seeing these repeating patterns. And so like figure out, know, is it money motivation? Is it time motivation? Is it like, what do you want your eulogy to say? Like here lies so and so who did everything themselves. Like is that what you want? If so, fine.

you know, like figuring out the true end in mind and working backwards. So I don’t know what of those motivates every individual person. You have to figure out what motivates you and then you can take the right steps to use that motivation to, you know, to use Kevin’s quote, to take the fear and turn or stress and turn it into passion.

Kevin Daisey (24:54)
Yeah. I mean, it’s, I’ve been there before, right? I’m doing, doing a bunch of stuff you don’t want to do. just crippling. I think like it’s, especially as a show every day and you’re like, I don’t want to be here. don’t want to do, I don’t want to do this. I don’t want to be here. Like that is talk about sucking everything out of you you’re not going to be efficient. You’re, you’re not working your hardest. and you’re, you’re just going backwards the whole time. So yeah, I think it’s easy.

You know, and this happens to me all the time too. I’ll go, I’m going to go do this thing. Cause now me and my wife, it’s like some rental property houses and stuff that so it’s easy to be like, know what? I to hire a contractor. Like I want to go do that myself, but actually enjoy that work. So it’s kind of like, okay, well yeah, I could hire someone to do it for me, but I kind of enjoy it at the same time. So, for me, that’s more of like escape, like, Ooh, I’m going to go build this thing or whatever. And I liked that.

Jordan Ostroff, Esq (25:51)
Sure.

Kevin Daisey (25:52)
Where some people might like, you’re crazy, man. I just hire someone to fricking do that. Like you can make more money if you were selling law firms marketing. but I enjoy doing it. So I, I think that’s fine, but I never really came to that conclusion until we were just talking right now.

Jordan Ostroff, Esq (26:10)
Well, and the craziest thing for me is, like, I think food’s the best example because all of us eat, I assume, you know, usually maybe three times a day. So if you like cooking, but you hate shopping, there’s a service that will deliver the stuff to you ready to go. There’s a service that will deliver the stuff to you not ready to go. There’s a service, you know, you can go out and eat. You can cook everything at home. You could grow your own vegetables. Like you have such a wide range.

Kevin Daisey (26:20)
you

Jordan Ostroff, Esq (26:36)
So figure out what you enjoy in the process, figure out what goal you’re looking for and put it together. So for your standpoint, you like doing some of the contract work, great. The minute you hit the part that you don’t like, you don’t wanna do electric, cool. Call an electrician and then you focus on the reframing the room. You don’t have to commit 100%, you can pick and choose the things that truly bring enjoyment in any of these things and highlight them. But for the things that you hate,

then figure out is it worth me doing something I hate and losing money while doing it and wasting time doing it and spending longer to do it than an expert would take and not spending the time with my family, like then don’t do it.

Kevin Daisey (27:16)
Yeah, no good point. that’s, you know, that’s exactly my wife doesn’t, don’t, she doesn’t go to the store and shop. It was like, it’s all done online and then they gets delivered. you know, she works, I work, that makes more sense than walking around the grocery store for two hours. So, time and money and it’s something we’ve done going for years.

Jordan Ostroff, Esq (27:37)
Kevin, I’m gonna share a really, talk about adulting, right? So yesterday, in the last couple months, I don’t know where my socks have gone. Like I don’t know how often I’ve bought socks in my adult life. I don’t think, maybe it’s once. Somehow I had like six different kinds of socks and now like one’s missing on all of them. I don’t know where it went. I don’t know if my six year old stole them. I don’t know if they went in the trash. I have no clue. So yesterday I had,

18 pairs of the exact same socks delivered that all match each other and I can throw out all the rest of them and so like I’m not doing laundry but whoever is they’re saving time not matching up all these socks like that is super anal and adulting and I get it. So I’m not telling you to necessarily always wear the same socks but what I’m telling you is like you figure out the things that are inconvenient in your life like figuring out where all of my one pairs of socks are that don’t match anything else and you just solve the problem through

Kevin Daisey (28:21)
love it.

Jordan Ostroff, Esq (28:35)
money through delegation, through automation, through people, or stop doing it. Trust me, I am guilty of wasting a ton of time still, even now. So it’s okay to just do less. We don’t have to constantly be looking for more to put onto our plates. We can take things off of our plates and be more effective at the things that are still on our plates.

Kevin Daisey (28:58)
Yeah, that’s hilarious. mean, I got so many socks and like, I don’t know how many don’t match. It’s ridiculous. Like every year, my mom buys me a pair of random socks for Christmas. So I just keep them all. Like I got two or three drawers full of socks. I think I might have to take up your idea there. My wife would love that for sure.

Jordan Ostroff, Esq (29:14)
Dude, was like 20 bucks on Amazon. I have 36 different sock, whatever one is. They’re all the same. So much easier, so much, and you know, I’ve got a couple pairs of socks. Not that I dress up maybe once a year at this point, but they still exist. Yeah, correct. I don’t even wear socks most days. Unless I’m going to the gym or running or something like that. I usually don’t even wear socks. There’s more reason to not know where they are. I might have left them at.

Kevin Daisey (29:29)
Flip-flops, your knee sucks. If I lived in Orlando…

Jordan Ostroff, Esq (29:41)
disc golf course or a golf course or I don’t whatever

Kevin Daisey (29:46)
If it’s hot out, I’m wearing flip-flops as much as I can. Here’s another quick example. Well, two examples real quick. One, I go back and forth, I used to have someone mow my lawn. And I was like, I’m mow my own lawn. I went and bought, and I was like, save some money. So I bought a two or $3,000 lawnmower. And I was like, all right, if you did the math, it would take like four years of weekly mowing to pay for my lawnmower.

So I’m not saving money. I just like doing it. And I use a tractor for a lot of other stuff. I took the kids around like a hayride wagon and all this stuff for Halloween. So, you know, I just like having the lawnmower, the tractor, and, I’m not saving any money by paying someone $40 a week when the tractor costs so much three grand. Like, so, you know, so I think we ladder ourselves on some of those things, but then it comes to like the, grass and the seed. I’m like, I’m over that crap.

So I’m hiring that out.

Jordan Ostroff, Esq (30:47)
Well, but let me take you a step farther. like, look, as lawyers, most of us work in a small geographic area. I cannot practice outside of Florida. I don’t want to practice outside of central Florida. So I can hire a long guy, I can explain to him what I do, I can explain to him that he cannot ethically, you know, solicit for me or whatever. But like, my long guy sends me business because it’s a PI, everybody gets in a car accidents, you know, are the dry cleaning person sends us business.

once a year, once every three years, once every five years, who cares? Because even Kevin’s breakdown of four years for it to be worth it and then throw in a $25,000 PI case and now it’s 10 years for it to be worth it and that’s assuming I enjoyed doing the thing and could do the thing in the same time and whatever else. This is how we can make all of this work by multi-impact, not multitasking, but multi-impact. We can outsource to people, turn them into referral sources and friends and colleagues get the stuff done better and faster.

while we can enjoy what we’re doing more frequently, like the landscaping without, or, you know, the lawn cutting without having to worry about the seeding and fertilizing and whatnot.

Kevin Daisey (31:57)
Yeah, no, I think it makes a ton of sense and I think it’s easy to fall into the, know, constantly, right? So even if you like, I it’d be good to make, I forgot what book it was, but it’s like making a list of all the tasks you do in a day and then you bucket them, list them in columns of, you know, $10 an hour of work, $100 an hour of work, $1,000 an hour of work, and $10,000 an hour of work. And if I can think of the book, I’ll post it whenever this goes live.

$10,000 an hour work, you’re like, well, what the hell would that be? Speaking on stage at a conference or, you know, say a big sales opportunity, you know, where you’re, you know, you’ve a referral partner, you know, where you’re getting your referral partner, stuff like that. Yeah.

Jordan Ostroff, Esq (32:40)
Well, or internal training. mean, I’ve got a, you know, six people here in Orlando for me to spend an hour training them could be $10,000 work if it helps them get a case slightly better, if it helps them sign up a case we wouldn’t have, it helps them get a good review that leads to another case, helps them get a better resolution. Like there’s, trust me as a business owner, there are things that you can do that are million dollar ideas that seem so stupid that it would move the needle that much. But turns out over a year, 10 years, 30 years moves the needle a ton.

Kevin Daisey (33:11)
Absolutely. Well, the thing is, you know, how many, how much $10 an hour work are you doing? And even as a lawyer, how much $100 an hour work are you doing? Like stuff that you should not be doing. And so that was a good exercise, but I guess I did that exercise a while back and cut a lot of stuff, but then stuff seeps back in. Right. So it’s this constant battle of, I’m just going to do that myself. And so even though I have like 55 employees, like delegation has not been.

too, too difficult, but every time something new comes about, like, I’ll do that. And then next thing you know, you’re, you’re back to holy crap. You know, at the office late again, I got too many meetings on my plate doing too many things. And you’ll start to realize that, you know, I’ve been doing stuff that I shouldn’t be doing. So I think that’s another issue is, you know, if you kind of figure things out, you can just slip right back into it.

Jordan Ostroff, Esq (34:09)
Well, yes and are you familiar with the concept of the hedonic treadmill? So it comes up in in a how to win friends and influence people. He talks about these kids that had like something terrible happened and they end up in an orphanage and then like they’re playing and having fun after you know, six months like the ability to adapt.

Kevin Daisey (34:15)
not.

Jordan Ostroff, Esq (34:30)
We have since learned more about the human mind and we have the hedonic treadmill. So you hit the lottery and after six months you lose the money or you’re at least as unhappy as you were beforehand because you compensate for it. And so we all have this naturally built and when it’s to help you overcome like losing a limb or a spouse or a child, it’s great. When you have it where it’s not allowing you to appreciate anything that’s gone far, it sucks.

But at that same time, like the thing that made sense for you to keep on your plate six months ago, you might adapt to a situation where it’s no longer makes sense for you to have it. It’s not that it was the right call then it’s that it’s the right call now to delegate that or with dude with AI changing everything, the things that I used to have to do that now, like I have a chat GPT or a GPT that’s good enough to know me to have the first draft of copywriting for me to make final approval.

instead of having to do an outline, instead of having to put some of the stuff together and have it come back. It’s amazing how technology is changing what’s the best use of our times.

Kevin Daisey (35:26)
Yeah, yeah, yeah.

Yeah, that’s a good point. And, yeah, it is okay to be like, you know, I’m going to do this for now. This is temporary and I’m going to find someone that’s going to do this for me. But, you know, so that, I think that’s fine. Like you’re saying it’s as new things come about, new ideas, new processes within your company that you might put that hat on for a temporary point of time. And I think, you know, as an owner, you know, entrepreneur or lawyer, you know, it’s nice to be able to do those things and jump back and go.

I need to take care of this for a temporary time. Maybe lost a person or maybe I wanted to show my team, Hey, I know what I’m doing there, but you don’t want to continue to wear the hat. You want to be to step back out of it, but it’s good to build up the skills and have had to go through that. Right. so you, you know, if you’re needed, you can, you can step back into that role for a temporary time.

Jordan Ostroff, Esq (36:23)
So I would say slight pushback, get to do that, get to go through that so that you can learn to delegate it better, that you can explain it better to the next person, that you have a better idea of who you’re trying to hire to fill the spot the next time around. Get to do it. Because as a business owner, we don’t have to do anything. We are choosing to go through this grind.

Kevin Daisey (36:26)
Sure.

I like that.

No, I like that. Yeah. It’s getting that experience and have a better understanding of it, especially when you’re trying to hire someone to do it. And yeah, you’re not familiar with it. So a good, good point there. So, well, Jordan, I appreciate your time on the show. I love what you’re doing. I’ll show you guys are check Jordan out. He’s got some great stuff to share. Jordan, what’s the best way for our audience to connect with you?

Jordan Ostroff, Esq (37:14)
Sure, if you go to jordanostroff.com, you’ll find my website. You’ll get a really good feel if I’m the right vibe for you. If not, I totally get it, no harm, no foul. But if I am, I’ve got a free newsletter that goes out every week. I’ve got a podcast that just started this Tuesday. So a lot of free info, thank you, a lot of free info out there really genuinely trying to help more lawyers avoid the burnout, enjoy their job, show up better for their clients, their employees, their spouses.

Kevin Daisey (37:30)
Congrats.

Jordan Ostroff, Esq (37:42)
and ultimately live a great life. We can do it as an industry. And the more we get together to not be okay with the status quo of the billable hour as a badge of honor, the better we all will be.

Kevin Daisey (37:55)
Well, love what you’re doing and appreciate that. Please reach out to Jordan and connect with him. Check out his new podcast and, we’ll see Jordan soon, but, it’s great calls. Love what you’re doing and appreciate it. So everyone have a great day. Get out there, look at what you’re doing, make sure you’re doing the right things and doing what you love. And if you’re not really sure. Reach out to this guy. We’ll talk to you soon. Thanks, Jordan.

Jordan Ostroff, Esq (38:20)
Thanks so much.