Andy Hays – Inspired on a Train Station Platform (306)

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Andy Hays - Inspired on a Train Station Platform (306)

Andy Hays is an entrepreneur, a lawyer, a master beer brewer, and a world traveler. His firm, called HaysFirm LLC, is a collaborative partnership between Andy and his wife, Antonia. It focuses on estate, probate, trust, and business law, as well as the regulation of restaurants and the acquisition of liquor licenses.

Despite having its headquarters in Chicago, the company is purposely designed to be run from wherever Andrew and his family are at any given time, whether in Colorado, Costa Rica, or Croatia. Andrew got the idea of this business model on a train station platform in 2014 when remote working wasn’t a thing yet.

Growing Your Business and Enjoying Your Life

Entrepreneurship surely is a rollercoaster. It’s a journey filled with ups & downs, accomplishments, failures, and all in between.

Can there be balance?

Is it possible to build your future while also enjoying the present?

Andy Hays was standing at a suburban train station in 2014. He used to take the train all the time, and after countless rides, he started to notice a pattern. There were always the same people next to him in their 60s. They were successful, but were they enjoying life to the fullest?

At that moment, Andy decided that he wouldn’t wait until their age to do something fun and moved to Costa Rica to grow his business and enjoy the beauty of life with his family.

Surely something we can learn from!

And now here’s Andy Hays.

Full transcript below

Video With Andy Hays. Inspired on a Train Station Platform

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Podcast with Andy Hays. Inspired on a Train Station Platform.


business, people, chicago, attorney, wife, thinking, years, costa rica, andy, working, firm, figured, zoom, guess, education, kids, law school, train, run, feel


Andy Hays, Mike Malatesta

Mike Malatesta  00:04

Hey, everybody, welcome back to the How’d It Happen Podcast. I’m so happy to have you here. My podcast is powered by WINJECT Studio. And today, I’ve got Andy Hayes with me, Andy, welcome to the show.

Andy Hayes  00:26

Thanks for having me, Mike. Appreciate it. Glad to be here.

Mike Malatesta  00:28

So as you know, I fulfill my promise to you every week to bring you an amazing success story. And Andy is certainly one of those that will fulfill that promise. So let me tell you a little bit about him. And I’ll preface this by saying that he is a lawyer. But I don’t know if this is going to be about law or lifestyle. And you’ll find out why. So Andy Hayes is a master beer brewer. I don’t know. Is that the right thing to call?

Andrew Hays  01:02

Yeah. Brew master.

Mike Malatesta  01:06

Okay. See, I thought if I said brew master, people might not know if it’s beer brew or whatever. But anyway, brewmaster Yes, that’s true. Yeah, yeah, wasn’t sure. He is that and he is also a lawyer and entrepreneur and a world traveler. His firm, which is called Hayes Firm, LLC, is a collaborative partnership between Andrew and his wife, Antonia. It specializes in estate, probate, trust and business law, including restaurant law, and obtaining liquor licenses. And there’s other things too, that they do that I want to get into as well, because it’s kind of unique, like a boutique firm. I’ve had a lot of people with law degrees on my show, but I don’t think I’ve had an entrepreneurial attorney who practices law on my show. So this is special, a rare occupation.


But I guess in your in your what the subject matter you’re hitting it is.

Mike Malatesta  02:10

Yeah, well, you know, I just drove back from North Carolina. And it doesn’t matter where you drive back from, the only lawyers that are advertising that have like private firms are the injury, you know, injury, medical malpractice, you know, all of those kinds of things. So you kind of get fooled into thinking that those are the only kind of non-corporate law firms out there and boutique litigators and people who do what you do seems to fly under the radar, so although the firm is based in Chicago, it’s set up intentionally to run from wherever Andrew and his family happened to be, whether that be Costa Rica, Croatia, or Colorado, the model was inspired on a train station, plot platform in 2014. Way before working from anywhere became the thing it is today. And so we’ll dig deep into that, or at least we’ll dig into it deep enough, because Andy has deepness issues, and we may not be able to get super deep, but I’m kidding. We will get deep. Andy


we’ll see. We’ll see how much I can take.

Mike Malatesta  03:25

So, Andy, I start every podcast with the same simple question. And that is, how did it happen for you?


How did it happen? I don’t know — it’s still happening, I guess. I mean, I hear that story, you know, my little short bio. And it sounds like it’s pretty much patched together without any kind of long-term vision for how or where it ends up. And that’s pretty much how it is, you know, that’s not to say that I don’t have a plan. I mean, I have a plan for my business, but I kind of make decisions based on what’s best for me and my family, you know, at any at any given time. So I guess it’s still happening is my answer to that? I don’t know. I don’t know.

Mike Malatesta  04:18

So, okay, fair enough. I may explore a little bit here there, so you graduated from college? The way I take it, you graduate from college, you went and did a did a few years there before you went to law school?


That’s right. So why? So I graduated from college, and I went to Lake Tahoe and was a ski bum for a year. Winter and summer. And then I went to a public history graduate program at Arizona State. And that was a great program, great place in Tempe there. But it was not what I was looking to do, the academic situation did not fit me. And I had been brewing beer since college. And I decided I to just go to Denver, I had a friend there. And I thought that I might be able to get a job somewhere because that’s one of the few places where there were breweries everywhere, you know, maybe or at that time, like Oregon, Washington. Maybe California and Colorado, that’s where it really was, there was a ton of breweries in those places. Now they’re everywhere. But so I went, I went to Denver, got a job there. And then my job was a corporate situation, rock bottom there all over. So I started in Denver, and then a job opened up here in Chicago, a much better job, salaried, health insurance, all the stuff that as a young brewmaster is, you know, hard to come by. So I took the job because this is where I went to college. So I had a lot of friends here. I love Chicago, I still do. And it brought me back. And it was a much, much better job for opportunities to make beer. So that’s how I ended up back here. And then I reconnected with my wife, who I knew in college, we were friends in college. I think we were better friends. And this story always comes out. But she kind of termed this more as like, strong acquaintances maybe, but it was whatever it was. We weren’t close friends. But we reconnected at a friend’s wedding, and then started dating and she was in law school at the time. And then just from talking to her, kind of looking at what she was studying, it seemed very interesting to me and I, when I went into law school, I was going in there with the intention of as you say, a lot of your attorneys did you have are trained attorneys on your podcast, I was hoping to go to law school, and then own my own business someday. And that was always what I wanted to do. So I turns out, it was a law firm, but I mean, I’m doing it. But that was kind of what put me into law school. And then I got, I got into some of the trial advocacy courses. And I found it fascinating and still do.

Mike Malatesta  07:38

And when you Okay, before I go there, I missed what you were studying at Arizona State. What was that


Public history. It’s like, what it’s not library sciences. It’s more kind of museum based. And there’s a historical preservation component to it. That was kind of it was kind of more mean, it was academic, but it was also kind of geared more towards, you’d be applying your education into the real world through kind of preservation and maybe museum or things like that. It’s fascinating field, Arizona, it’s a strange place to study it, because there’s not a lot of physical history there to preserve. But it was a good program.

Mike Malatesta  08:22

And so that was that was after undergrad. So you were kind of considering what the next thing was. I guess I


knew I wanted more education. Yeah. Okay. I can’t say that. I love being in school. But I do love education. If that makes any

Mike Malatesta  08:37

sense. No, tell me what an interesting distinction, what’s the so


I mean, I don’t know, I love learning I love I don’t really like the student, some people love the student lifestyle of, you know, whatever that is, I don’t really necessarily love to learn something and then tell it back to the teacher, which obviously, if you’re in grad school, that’s not what you’re doing. But you there’s still some component to that. But the education has allowed me to do a lot of a lot of things you can’t do without an education like to be an attorney. And I mean, I know you don’t need a formal education to run a business, but I’ve never had any formal education or any business but I mean, that’s the type of self education that I’m really much pretty much engaged in now. On the business side of things,

Mike Malatesta  09:30

so let me let me latch on to that for a little bit. Just to get your put your futurist hat on with with regard to education and self education, what do you think, you know, your situation was go to an institution, you know, learn, get a degree, and then use that degree to practice or whatever. Do you think what do you think is going to be the path for your kid Do you think that education for that because your kids are on the younger side now? Right. So do you think the path, the educational path for them, or the learning path for them will be the same as it was for you and and your wife? And your Do you think there’s going to be some transformation of that that’s going to occur before they experience?


Yeah, I mean, I don’t know. I mean, it already has been different for them. Right. I mean, just through these last couple of years, I’m sure in this doing this all online. I mean, I really don’t think that component is going to go away. It’s certainly not go away in its entirety. I mean, I still think there, there is a value in a classroom of people being in person. I don’t think we’re there yet as humans or, or bots, or whatever, to where that isn’t a valuable thing. So I think, yeah, there’s there definitely will be that type of component. But, I mean, I think that I mean, when, when we went to school, right, I mean, there was any kind of online wasn’t a thing. But you know, there were like correspondence courses there, those were kind of viewed as lesser than experiences, right. But I mean, now most schools have a program where you can do certain programs online, and then you get the degree from Arizona State, or whatever it is, and there’s no kind of Asterix on your diploma. So, I mean, I don’t know what my kids will choose. But I’m sure that those options would be able to be available to them where they would not need to do that to get the same type of education now for law school, I think I don’t think there’s any kind of attorneys are notorious, which is probably why I’m the first one on your, on your podcast, are notorious for being way behind on anything that remotely smells of technological advancement. So I’m sure law schools will all will not be the last to, to do that.

Mike Malatesta  12:04

Okay. Yeah, really makes you wonder, because the, you know, the most institutions, and certainly the most prestigious prior to the pandemic, it was, you know, the whole value proposition was in the coming, and the exclusivity and the people you surround yourself with, and everybody, everybody, from the lowest institution to the highest level institution had to sort of completely shift their whole story about what they could provide and how valuable it is. And kind of like, how do you write right? And you think to yourself, Well, okay, so now, the pandemic sort of weaning and, you know, last 2021 22, school year that everybody sort of went, right, but the genies still sort of out of the bottle. Right. And it’s, it feels like, everybody’s there, trying to stuffed it back in there. But I don’t know. I just wonder if it can really be stuffed back in there, because they’ve certainly proven that they’re able to do it. And they certainly, you know, adopted the value the completely different value proposition that of course, you can get a loyal, loyal degree online. Look at did it. Right. Right.


That was only for 2020. That was equivalent. Yeah. Now it’s back to being, you know, second class. Yeah. Methodology?

Mike Malatesta  13:34

Well, yeah, it’s like, oh, well, we did it. But it was so brutal. That, you know, it just proved that our on on campus model is the way to go.


I’m brutal enough to reduce the tuition or provide a credit or anything, just brutal enough.

Mike Malatesta  13:48

Fortunately, we got a Housing Credit from my daughter, but yeah, that’s I think, definitely credit. Some


people did. I’m not saying that, like, kids are too young. But yeah, I’ve heard that happen. And that was about it, though. I think that

Mike Malatesta  13:59

people Well, it’d be it’d be interesting to see what ends up happening with your, with your children. Because it I think there’s just as good a chance that it’s the same experience as yours as it is that it’s completely different.


But, I mean, I guess it goes to what motivation do these institutions have to change? You know, that kind of goes with tuition? I mean, if everybody’s just raising their tuition all the time, what what motivation is anyone have these institutions to change the model? You know, they don’t I guess the same thing could be said of attorneys, hourly billing models, you know, or whatever. It’s, it’s there’s all kinds of entrenched ways of doing things.

Mike Malatesta  14:45

Yeah, I mean, it feels like and I again, apologize for this, this tangent, but it feels like, the convergence of all good things, right. Inflation is that 8% Now, right, so they’ve always raised rates higher than the inflation rates. So it’s like, wow, look at that. No 8% So we can go. And you know, this whole thing about just lending people money to go to school, regardless of, you know, the likelihood that the, how long they’ll be in debt for it’s horrible. And then forgiving the debt. You know, it’s kind of like this cycle. It’s just feeding right into the old model, as opposed to subsidizing Yeah, you gotta shut that spigot off somehow, I think in order for it to really change but, but the internet’s got a weird way of changing stuff. So the ski bum thing. So you went to us, as I recall, you had your history major undergrad, which is often a path to law school, right? History, right. So


it’s also a path to being a ski bum. Yeah,

Mike Malatesta  15:48

well, that’s why I want to I was kind of taking it one way. I wanted to bring it back. But anyway, yes. So how many ski bums are is, like 90% of ski bums? Are history majors? Or what?


I don’t know. But you’re definitely well represented.

Mike Malatesta  16:04

What were you thinking? So I guess the point I was gonna make was, a lot of history majors is sort of a path to law school, at least it was when I was going. Yes. So where were you thinking you were going to go before the ski, the ski bum? And no,


it’s not a thing. You know, I just, I just knew that that was the most interesting thing to me. I went to a liberal arts college, I certainly was not going to study something like pre med, or engineering or something hyper technical like that, you know, that’s not my skill set. And I have no interest in that. It was simply the most interesting thing to me, you know. And I knew that. I guess I in my mind, I kind of had that I would go to another, you know, go on to an advanced degree, which is explains the, the Arizona state program. And then I kind of once I was there, I rethought it saying, Well, I mean, I just kind of this had been in my mind that, oh, I’m going to do this, you know. And it was just once I was there, I realized that maybe it’s not the best thing. So it’s just simply the most definitely far and away the most interesting of courses I took, so I just stuck with it.

Mike Malatesta  17:17

Okay. And I liked that answer. Because the I also went to liberal arts college, maybe that’s why I like the answer, but and, and chose English as my major. Right. And, and, you know, so I feel like those are some of the strongest majors because you, you aren’t pigeonholed, even though people want to pigeonhole you like, oh, history, major English major, you’re going to be a teacher, right? That’s right. Yeah. Well, no. But I’m also not going to I, you know, I’m not so not sort of, like engineering. That’s what I’m going to be an engineer. So I take engineering all the time. I think it’s, I think it really opens your eyes. I think it really opens you up to a whole lot of things that I mean, you can be anything, because you’d learn how to think and read and write. And actually,


I’m pushing it big time on my daughter, who’s a sophomore in high school, finishing up her sophomore year in high school. I’m pushing liberal arts school for her because she would be very, that wouldn’t be good for her, you know? Because I mean, I think it’d be good for any kid. I mean, unless you are gunning to be in that you’re dying to be an engineer, then, you know, oil was, maybe it is good for you. I don’t know, I’m sure they have something but yeah, maybe you’re better off in a big, big technical school. But yeah, for those of us who aren’t wired that way, it’s a great education. And

Mike Malatesta  18:43

this entrepreneurial path that you ended up on the as I as I recall, it was maybe somehow influenced by your dad. I don’t know if that was sort of an intentional influence, but I believe your Dad Yeah, I


mean, well, my dad was he passed away when I was 18. But he was a family practitioner doctor. So I mean, that’s kind of there’s those guys are still out there. The family practitioners a lot. Not as many as there were then but he and some partners owned on their own practice. So he used to always tell me that that is that’s something I should shoot for being your own boss, you know, no matter what I do, that’s what you should do. You know, and I’m giving my kids that same advice and I think that was great advice.

Mike Malatesta  19:33

Did that advice stick with you? I mean, um, or did it come back like Reese resurface at some point?


I think it must have resurfaced, right? Because if I’m gonna sit here going to public history programs and things that’s not really getting me there. So but it definitely once I was out of law school. I was working with a firm for a couple of years. It was not a good fit. So I was looking for another job and Then, in looking for that other job, I discovered that these other situations were drastically similar to what I was in, you know, so I’m like, Well, I’m going to change this, this small firm for this other small firm, it’s still the kind of the same dynamics with the boss and the secretary, who cares more about what the boss says, and won’t listen to the young guy and never helps him and all those kinds of dynamics. And then I just kind of lightbulb went off, I guess. But then I was immediately. I mean, quickly, very determined to just try owning my own business. And then once I started doing it, even though we had like, I mean, you know, started from scratch. Definitely from scratch, no clients. And even though I didn’t even know how I was going to pay rent, it still felt so much better than anything I’ve ever experienced. workwise up to that point, you know, and even though I’d done some pretty cool stuff in restaurant, we’d had some good wins in the law firm that I was working for. But it’s better to be running your own business and, and broke than doing well, as an employee. That’s the way I think I mean, that probably sounds insane to some people, maybe not your listeners, but it kind of sounds insane when I say it, but I really do believe it.

Mike Malatesta  21:32

Well, I, I think it probably sounds insane to most people, and maybe some of the people listening. I’m curious, like, how do you thinking back? How do you sort of square that up? Like, it’s better for me, I feel better. I’m paraphrasing what you said, but I feel bad. You know, being my own boss, even though I have no clients and no money. And, and a lot of question marks in front of me than I did doing work that was meaningful, but maybe for people that weren’t? Or in a situation that wasn’t as meaningful for me. Right. So let’s do I get the part about wanting to go on your own. But the part about, you know, the scary part about not having anything when you do this? That’s a difference maker?


I mean, I don’t know if I have an answer. It’s really just some kind of like, you know, mental illness, maybe I’m only half joking. I mean, there’s some complete lack of aversion to risk. You know, I mean, I guess it was, I can’t shouldn’t say that. But I mean, I guess my backup was, well, if I fail, I’ll just go work for another firm again, you know, and I’ll, I will have learned something, you know, so I didn’t really see a downside. I guess that’s what it was. I mean, I’m sure there was a downside. But I just either chose not to see it, or was too excited to see it. I mean, okay. Two very small children at the time. But we still have, they’re just not small children anymore. So yeah, I mean, don’t get me wrong, I was not broke for a very, very long time. But it was just weird. Because I remember thinking like, this is me, owning my own business is worth 100 grand of income. And I truly felt that from like, a happiness, you know, meter or something.

Mike Malatesta  23:37

And yeah, so I think it is kind of unique, though, because a lot. I think that people who do what you did, you know, are in like the very, very, very small percentile, because a lot of people start their own business, but a lot of them that, like, they’ll take business from where they were, and convert it. And then that becomes their business or the thing that gets them started, which is helpful, right? It’s helpful from a cash standpoint, it’s also helpful from a confidence standpoint, like I’ve got something to start, right. But that doesn’t sound like what doesn’t sound like we had at all. So I give you a lot of credit, because that’s it’s hard.


I would have preferred to do it that way. But it just didn’t happen for me that way. I was too young to, to fresh out of school, you know?

Mike Malatesta  24:32

And what changed? Like, what was the first thing that happened where you were like, damn, this was a good choice.


Um, I think after I made it a year, I mean, my wife was still working at the time. She’s an attorney as well, as you said, we worked together. She was working for a firm so we had some income there. I think after a year, I kind of was like, okay, you know what This, I just was looking at the trends, you know, and I got some more cases. And I’m like, Okay, well, I mean, this is obviously not sustainable at this level, but I see the I see the trend and this thing, you know, because I was just meeting people. And I was out there connecting with people like I never had done when I was just, you know, sitting in an office, and, you know, trying to learn from some other guys. I mean, I had no choice. Right, I had to get out there. Yeah. I mean, I’m, that’s actually the part that, you know, I enjoy that part of the business still, is connecting and trying to meet clients and get new clients and solve, solve their problems. But yeah, it was probably about a year. I mean, it took a while, you know, to where I was kind of, it sat with me. And I said, okay, and then after about a year, I had before I got an office, right by my house, we condo where we live, because it’s like, why don’t any clients, I might as well have a place, you know, close to my house. And then, so I was working out there. And then after a year, I had a chance to move in with a guy and sublet some space from him down here and loop here in Chicago downtown. And when I did that, and then because that’s where I’d always worked before, was downtown Chicago, I’ve actually been working down here ever since. So then I moved down to with him. And then when that happened, and then I was back in the routine of, you know, taking the train downtown and meeting people down here and going to court and everything that was down here, the energy of this place, then I was like, Okay, this is this is real. Now, I’m, you know, really, you know, I’m not some attorney in some crappy office in the suburbs, I’m really doing this again. So that was really when it happened. And that that happened about a year after I started the business.

Mike Malatesta  27:00

And just fast forwarding, because it interests me having that office in, in the loop downtown Chicago during the pandemic, what was that? You talked about the energy and everything right, and I’m wondering, what happened? How, what was your experience, like, during that period?


Um, well, I mean, a lot of social distancing. And that was not an issue. I mean, I was, my kids were, you know, at homes, I was coming down here the whole time. You know, attorneys or essential businesses or whatever. So there was no kind of, we could open even though no one came in my door. So yeah, it was a ghost town. It was a ghost town for a long time. It’s just now. And then when Omicron came, it was a ghost town again, it was just but it’s filling in now. But it was very strange. At that time. Very strange, because, like I just said in my previous answer, or answer to your previous question was, the energy is what drew me down here and had a big impact on how I perform and think about myself in relation to this career. And yeah, it was it was weird. It was weird. And I mean, not a lot of it’s still weird. We’re still not doing CT. It’s all still on Zoom. So we don’t have that kind of thing. But yeah, it was very odd to be down here during that time.

Mike Malatesta  28:29

So I can I think I can appreciate how you could do like a deposition on Zoom. But how do you? How do you litigate like in front of a jury or whatever? On zoom? Like, how have you? That’s got to be so I’m assuming you’re, you’re, you’ve done that? You still do that?


Either. Yeah. If we did not do a jury and zoom, so the jury cases we do. Even the personal injury, guys, which those are those folks are all jury, right. Those were halted for a very long time here in Chicago. So they didn’t even do a zoom. I think when they I think some of them did. But yeah, in our area of practice, there were weren’t any jury trials. But yeah, it would be terrible. I mean, it’s Zoom is great. I mean, I think all people kind of realize this is great for some things and terrible for other things. is terrible for zoom happy hours is a joke, right? That was cool for like a week. And then the zoom, as you said, trials and evidentiary hearings. It’s terrible. But for the regular check in stuff, which is most of what court is for anyone who’s been involved in a lawsuit. It’s great for that, right. Just a quick update, but yeah, hopefully it’ll it will get back to that. It’s only downtown Chicago, all of the suburbs there opened up. You know, the suburban courthouses and downstate courthouses.

Mike Malatesta  30:11

Okay. So the, at the beginning of in the bio, I talked about these law versus lifestyle, or law or lifestyle, and I referenced this chant, train platform, encounter or probably encounter epiphany might be a better one, can you? What? So what’s that? What was that train, train platform epiphany about


not to be too dramatic, but it is true. It’s how I remember it. It was in relation to me moving down to Costa Rica, when we were talking. I just remember riding the train all the time. And I still do ride the train. But it was a longer train ride, I used to live much further out. And I remember sitting walking next to this guy, and I would just kind of say hi to him, didn’t really talk to him. And day in, day out day in day out, and I’m thinking like this guy, if I if I just keep doing this, I’m going to be doing like this guy, and then that’s going to be six successful life, right? I mean, that’s like, good career, right? This guy was growing his business by whatever percentage each year. And, you know, he rode the train downtown, and he worked hard, and he’s good, you know, success story. And it kind of freaked me out and bummed me out. for no real reason. And that kind of led to my wife and I, moving down to Costa Rica, which turned out to be for three years. But we initially were planning two years, because we didn’t know any Spanish. So we figured one year would be, you know, you got to spend a lot of time getting acclimated. And then after we then after two years rolled around. Why wouldn’t you stick? Because we, we had just figured out everything, like how everything worked, right? Because it’s it’s much everybody said, it’s not steep learning curve, it’s very, you know, shallow learning curve of a time it takes to develop any kind of competency, when you’re figuring out how to get around in a place like Costa Rica, there’s no, you know, Googling stuff is not quite as effective there as it is in the Chicago metropolitan area, and figuring out how to how to have access to stuff. So yeah, so we did that for three years, I presume?

Mike Malatesta  32:37

Why Costa Rica, what was what went into the choice?


We had been there, my wife and I, when our kids were very, very young. And we love the place. I mean, we were in the mountains. We didn’t even go to the coast on that trip. And we just love the place and just kind of doing a little research on, on what, you know, some schools down there, and actually visited a school, which we didn’t end up seeing our kids there for a number of reasons, but we just decided we should go down there and check this out. And like visit schools and do see like what it would be like to really do this, you know, I mean, our kids were, this was a few years ago, so we didn’t have any middle school aged kids. We had elementary school, and then it’s very small. One and a half year old. So I guess it was just from that trip, you know, I really love that place. It’s got a very cool vibe to it, the people are very genuine and not in kind of a manufactured tourism way. I mean, that’s really how it is down there. You know, and we wanted to learn Spanish, you know, for our kids learn Spanish. And it’s the same time zone as Chicago, well, half the year. So it was it was doable, that way, you know, we couldn’t go into Croatia or something would have been an option. My wife, or folks have a place there, that’s where they’re from, but that would have been too, too difficult. timewise you know, I would have been staying up all night sleeping all day or something.

Mike Malatesta  34:19

Okay, so I need to explore the thought process here a little bit because at that time 2014 or so. Is that right? That the time? Yeah. So you’ve been in business for six years or so at that point. You already talked to us about how you started with really nothing? And how do you so this is something I know I struggle with I pretty sure most entrepreneurs struggle with and that is taking any time away from their business but detaching in that way, like what you described. I think I had said there’s a very small person unless you start like you where they have absolutely nothing, and they just start, I would think that there’d be a very, very small percentage of people who could do kind of what you did, particularly at the stage of your business only six years or so into it. So, because most of us at that point, we’re barely getting, you know, taking a weekend off without doing anything, for example, right? Like, it’s like, a victory. And here you are, you know, take your whole family and move. How did you have the confidence? I guess, how did you have the confidence to do that would be my first question. And then how do you have the nerve?


I think that are they the same thing?

Mike Malatesta  35:37

No, they’re different. Yeah, they’re, they’re different words. So I’m saying they’re different. I know, they’re different


words, but I don’t know where they come from the same spot, I think, I don’t know. But the I think I had the confidence because of what you just said, you know, starting from scratch, right? That gives a lot of competence to a person, because I had built it up to a point where at that time, I guess at that time, there were just three of us. So there was another attorney, and then one paralegal. So I mean, I knew I could manage it. I would come back for one week, one work week, each month, and just kind of crunch in all of the things that needed to be dealt with face to face, and then do everything else over. I mean, not zoom, the Zoom existed, but I never downloaded it until the late winter of 2020. So yeah, just I had my phone that would ring in my computer, you know, the IP phone. So Chicago number, and I just did it that way. But yeah, I think that I just said, I think it was the same kind of thing. Um, well, if it really, truly does not work, I mean, it does not work at all. We just go back. So which that’s the easy part. Right? It’s going back, it would be the hard part was going down there. So I don’t know, I guess I really didn’t. I was just too excited by the whole idea. My wife and I both were, and it was the greatest thing we could have done. So I didn’t have a lot of negative. I don’t really do a lot of Plan B’s, you know, or I guess I did do a Plan B and we just come back. I mean, there’s you know, and then which is what we did after three years. Anyway. So we’re planning to do that.

Mike Malatesta  37:36

And what was the you had said, you know, planning on two years? And so you extended it to three? What was the reason for not just staying there? And what


I mean, it was, I guess it was, if I could have figured out a way to make money there, I probably would have stayed there. I mean, just me traveling so much. And all my businesses is in Chicago. And again, this is before the tech disruption of COVID. Right. I mean, so maybe it will be different now. But which the internet is really shifting Costa Rica, too. So that may be still on the table. But um I mean, we didn’t. Part of it was because of our kids. I mean, the place where we were at was great. I mean, it was our friends that had older kids. I mean, I saw a challenge in just what’s available for the kids. Okay, in, you know, there’s limited activities. I know, people that are making it work great. But I just know from my family, it would have been pretty it wouldn’t work. Yeah. Super small school situation. But the, I guess the main thing was, I really did want to focus on growing the business. And, again, presume revolution. I had to be here to do it. I think I still need to be here to do it. I mean, not maybe not all the time. But that was really what it was kind of, you know, refocusing on the business. Because I was kind of I guess, with that whole train story and everything kind of shows that I was maybe getting a little burned out. And then when I came back, I was more focused on on growth and really trying to set myself up so that I can, you know, function like, oh, I can do this. Well, what if I did it this way? You know, right. And especially now with Zoom. I’m just trying to think of ways to build my business so that I can do that. Right. So I do feel like that about my business, the same type of excitement, I guess you could say, as I did when I first started, you know, we just hired a guy who just graduated School, he’s going to be sworn in, in the fall. So I mean, we’re, we’re making those steps, you know, and doing those things that are going to, you know, grow the business, the right people in the right way.

Mike Malatesta  40:13

I, I liked the I liked that train station story because I, my wife is from Connecticut, like Southern Connecticut. And when we would go there, we would sometimes take the train into the city. And it’s, it’s probably similar to what you experience in Chicago. I mean, there’s many, many, many people, much seems like mostly men, but lots of people who, you know, drive to that train station, pay a pay a lot of money to park at the train station, and then get on that train, go into the city, do their job, get on a train get home late. Yeah, drive home. And that’s that, I mean, I’m sure they all have great jobs, and they’re making great money. But I just thought to myself, every time I see that, I think to myself, why what? What do you know, how can you do it for? How can you do it? For me, I had a buddy who did it for years and years and years and years. And whenever I would see him, he would say, Well, I only have and he knew exactly how much time he had to continue doing it. And I just thought to myself, What do you mean, before he retired? Yes. Right. How much longer he like he had it to the day, you know. And, but but you know, he had a great it was a great position and stuff. But I just thought to myself, you know, you get it, you get on the train at whatever 630 In the morning, and you get back at seven at night and you got to it’s just a given up. It’s it’s a lot and


the grinds on

Mike Malatesta  41:48

you. Great. Yeah, for sure.


Then you you kind of start to get to the point where that’s all you know, or can even deal with, you know, one of my friends just he did that. I mean, he was a major workaholic, one of these self professed, you know, workaholics like, I didn’t take a vacation. That doesn’t impress me.

Mike Malatesta  42:11

I’m barely saying he says it with pride. But I know Yeah, they all do,


right. And I got to check in on him. It’s a work acquaintance. And he just retired after COVID. He’s like, I got to step well, he’s older guy, but I wonder how it’s going for him. Because I don’t know how you go from that to just doing nothing, you know, I don’t know, I’m trying to I can’t do the just run out the clock on the career thing, you know, I gotta, because then my back will be too jacked up, I won’t be able to ski, you know, 50 days a season or something like I want to do all those other things, you know, so I’m trying to figure out a way to do these things now. Right? I mean, that’s what we’re all doing. That’s what you’re doing. That’s what everybody who’s trying to create a business that, you know, works for them, rather than we just are a slave to these businesses.

Mike Malatesta  43:01

Right. So how do you how do you anticipate? Well, how do you anticipate your education going forward in that in that pursuit, like you, you know, became an attorney, then you started your own firm. So you became an entrepreneur, now, you’re, you’re growing? You’re, you’re probably conflicted sometimes because like you said, you know, I kind of feel like I have to be here. When I’m when I’m growing, but you also have these, you know, the skiing and the other stuff that you want to do with your family. And I’m thinking myself, how do you how have you? How have you become? Or how are you becoming a better? Wow, better? Might not be? I don’t know, a better entrepreneur?


Yeah, I want to be, yes. Oh, I mean, I think now I’m just focused on getting to the point where the business can run without me having my hand in every single thing, which is, that’s what all practitioners are doing, you know, accountants or whoever, you know, whatever you do, right, is making that leap. Which, I mean, we’ve grown but I still feel like we’re, it’s kind of been I’ve just been a practitioner that is running a firm with some employees, right. So now I’m trying to truly get the business running with out me. I shouldn’t say without my involvement, but kind of without my involvement, you know. That’s what I’m trying to do. And that’s what my energy is now. You know, with the goal of taking a month or two off at a time, or not even off but just outside of the office, right. I mean, I like working. So I mean, just checking on things. You know, but not grinding it out? Certainly not that, you know,

Mike Malatesta  45:05

how much different Are you now than when you started?


When I started the business, yeah, I was thinking I mean a lot different, a lot different. I think that now I’m in a lot older now. I think I was I would stress out about so many things then. Financially, specifically, even though you wouldn’t know it from this first part of this interview, but still, I was obsessing about these things, right. I don’t do that anymore. Because we, you know, a lot of stuff has happened through the years with, you know, leases, and, you know, tenants, breaching co tenants, breaching leases, and all kinds of crazy shit, that has kind of scared the hell out of you. And then you figure out a way through it, right? I mean, that’s what we all do, as a business owner. So once you do that a number of times, you kind of start to realize you’re gonna be able to figure out how to how to get out from under these things. And then that’s, that’s a calm, calming, realization.

Mike Malatesta  46:20

and up and up, I feel like you begin to realize after a while, that all the stressing about it doesn’t change anything, you still have to do something. Right? Hey, starter,


was a mess. What is it like today? It said famous quote, it’s like something you’d see on a coffee cup or something was like, today is the tomorrow that you stressed out about yesterday, kind of thing like you, you know, like that no matter what, it’s here. This is what I was freaking out about, oh, wait, it was it’s all good. It’s fine.

Mike Malatesta  46:52

So I think that, that that gets that gets in the way, not just of entrepreneurs, but so many people. It’s like thinking about the what ifs instead of just, you know, moving ahead and addressing things that come along, it’s like, thinking about possibilities, or thinking about what other people are thinking. You’re obsessing about either of those seems like such a, it seems like such an easy thing to do, but so unproductive because you really aren’t changing anything, all you’re doing is just keeping yourself from moving.


Right. Right. I mean, I think that that’s what I mean, the culture is kind of geared towards that type of thinking, you know? Yeah, lots of analysis, lots of self-analysis, lots of analysis of plans, and all these kinds of things. I don’t think entrepreneurs like that, you know.

Mike Malatesta  47:51

So when you get to the point where you think you want to be you know, sort of I, as you were talking, I was thinking about, okay, so Andy needs to get to the point where he’s running the business, but not necessarily from a billable standpoint, right. You gotta like separate yourself and run and grow where so when you get to that point, where, what do you think your life will look like?


Well, I would love to have an apartment here in Chicago, spent a good portion of time in southern Colorado, and then spend a good portion of time in Costa Rica. So I don’t know if you’re speaking emotionally, but that’s what I’m just saying. That’s like, physically what I would like to be doing. Okay, just be able to go between those spots. I mean, that would be that would be it, you know, and I don’t want to, I’m going to run my business, and then I’m going to go on vacation for 10 years. I mean, I don’t want to do that. You know, I want to keep working, as you said, which I think that was embedded in your question. Yeah. And keep growing. I mean, that’s what’s to just do the job doesn’t interest me. I need to figure out a better way to do things. And well, it feels

Mike Malatesta  49:13

like even though you mentioned physical places, it felt to me like there was an emotion tied to each one of those things that you Yeah, you’re very perceptive


there is yeah, there is. I mean, certainly Costa Rica. I mean, that was a very important time in our lives. When we were down there are small kids.

Mike Malatesta  49:33

Can Oh, go ahead.


Yeah, here. I mean, I’ve lived here my whole adult life. So

Mike Malatesta  49:40

I’d like can I ask you a question about the partnership, the business partnership with your wife? Because as Was that something you contemplated from the very beginning when you when you should have broke out on your own and she had the job at the other law firm?


Yes, no, we definitely did not contemplate it. The

Mike Malatesta  50:00

Begin. So okay, so how we come together,


she was had the job. And then we had two small kids. And then she kind of went down to part time. And then as I, my business grew, she, I forget, even when I’m bad about that kind of stuff, but there was a point where I was when she had our sons now going to be turning 12 This summer, when she had him, and then she took her maternity leave. After that, she, we were at a point where I was like, Okay, why don’t you don’t need to go back, just don’t go back. We’re just going to, you know, live off of the business’s income. And then she was all in on the kids. And then when our youngest kid, couple years ago, when we would when we came back from Costa Rica, so that was like, almost four years ago now. He didn’t need so much. You know, he wasn’t one or two year old kid. So he, she had more time. And then at that point, it’s like, well, what are you gonna do Bill worked for some law firm? You know, I mean, we could use the help here. So then she started, we started working together that way, you know, and she kind of focuses on a lot of this young man that we just hired. I mean, that was all her, you know, she kind of we kind of allocate things. So it’s not like we’re sitting there next to each other working on cases. It just allows us to divide the work up better things that have to be done in a business, you know, that aside from billing, the hours and things, but she does that as well. Okay. And kind of organic, it just kind of happened, you know, it was like, come we need help come help us rather than plus, I don’t think after what we did, that she could just work for someone else who could write?

Mike Malatesta  51:55

Yeah, you would think right, yeah, after you’ve had that kind of freedom. And I had to go back, because the expectation certainly wouldn’t be that that would be okay. I wouldn’t,


I’d never, it never occurred to say it wasn’t something we thought about, that she should do. It was just obvious what she should do.

Mike Malatesta  52:14

Yeah, I was. I’m glad you currently qualify. Clarify that, you know, you’re not sort of working side by side. Because every time you I think of that, you know, no, this isn’t realistic or anything, but I think about those TV shows, sometimes when the desks are like, facing each other, you know, so yeah, husband and wife team, and they’re facing each other all day long. And


that would not work out. This barely works. That was definitely not 100%.

Mike Malatesta  52:40

I know, I, I never worked with with my wife except, like, occasionally time to time and wish she would help with something or whatever. But I just, I just thought from the beginning, there’s no way I could,


I mean, I I’ve heard of guys where their wife were attorneys, small term firm attorneys, maybe they’re a solo, and their wife is their, you know, Secretary or administrative assistant or whatever you want to call, right. It’s that dynamic would be brutal. You know, I mean, here, it’s, my wife’s an attorney, I’m an attorney. And she’s doing a separate thing that I’m doing, it’s much easier to manage than having that dynamic of some kind of, if I’m telling her what to do. Oh, yeah, asking her what to do. That would not be good. So. But yeah, this is working pretty well. So it’s just a matter of dividing up our tasks and making sure that we’re not, you know, crossing paths and working closely together all the time, you know, at least that’s how we do it. I know. There’s, you know, others do a different. Suppose don’t do it at all.

Mike Malatesta  53:49

So I think thanks for sharing that. By the way, I think. My last question is, I mentioned this in the bio, it’s on your website as well, helping people get liquor licenses, and I’m thinking to myself, why do you need an attorney to get a liquor license? Like, isn’t that just a form or something? But obviously, there’s something to it if it’s something you sort of specialize in? So what’s going on there? I mean, people know, the back end of this thing.


I do agree with you, why would you need to turn but in Chicago, Illinois, you do. You don’t technically need one, of course, but it’s a very good idea to have one in Chicago. The Chicago bureaucracy is brutal, for lack of a more eloquent word. And we know how to how to work that you know, and how to, what to do, who to call, how to email who to wherever go visit, and how to do it. But yeah, I mean, most places, even in the suburbs around here. Yes, it’s just a form. So, but that was a niche that my friend And from college owns a couple of bars, and I did it for him once, and it was just, you know, crazy. And then once I figured out how to do it, and what all this stuff actually meant, then, you know, I did it for one of his friends. And then he had a second bar, and then it kind of grew from there. So once we figured it out, because of a friend of mine, who is still client. That’s how I learned it, you know, it wasn’t something I went out and is a good area, it’s a good area of law, because there’s a lot of regulation, and, you know, restaurants, like any other business, they need all the things, you know, they need the operating agreement, they they have all of the same issues that any other business has, but they do have this extra regulatory wrinkle, put on them by the city of Chicago in the state of Illinois.

Mike Malatesta  55:53

And just out of curiosity, is it is it? If the restaurant goes out of business, does the liquor license go away? Or can the next company that, you know,


if the place goes out of business and goes dark? You know? Yeah, the liquor license expires, and then you wouldn’t, but if you buy a bar, you have to buy that company. So you buy the corporation that’s running the bar, and then the same license. So people, you don’t really transfer the license, you just the person just buys the I don’t wanna get too technical, but they buy the corporation. So yeah, there’s some there’s some licenses here that have been around for well over 100 years in the city. Because it always keeps getting it keeps getting sold or transferred to the sun or whatever. Now there’s some very old licenses.

Mike Malatesta  56:50

Well, there you go, folks, if you need a liquor license in the city of Chicago, and he is in his firm or your pathway to getting that. Yeah, something I never, I’m glad there’s probably a ton of stuff in Chicago, where you need an attorney to do things that you could do with a forum somewhere else. Maybe now that you’re saying


that, yeah, the further west you get the less forms there are, you know, maybe until you get to like San Francisco or something. But, you know, Chicago and the East Coast, I think they’re, they’re pretty entrenched in the bureaucracy.

Mike Malatesta  57:22

Well, thanks for the free. The free advice there. Andy, thank you so much for being on the show. I I’ve enjoyed this opportunity to explore your story and share it with other people. I do think it’s very unique. And I do. I do love that you identify as an entrepreneur and not just as an attorney as well and that you’re thinking entrepreneurially about your future. So I think that’s good inspiration for everybody. That’s listening, that is thinking, you know, they identify themselves maybe as a lawyer or an accountant or an engineer or something else, and they could very well be an entrepreneur too. Alright, so this is yeah, so this has been fun. Thank you so much.


Thanks, Mike. Appreciate it.

Mike Malatesta

Mike Malatesta

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I help entrepreneurs get unstuck, take back their power, achieve their life objectives, and create the futures they want.

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