Striking out on Your Own

June 14, 2021

On Episode 13, Mark Willoughby and Tom Orecchio speak to Chris Hliboki of Hliboki Law. Chris discusses his decision to strike out on his own as a solo legal practitioner after working as an associate for another firm in the early part of his career. He talks about the challenges he’s faced, the rewards that decision and others have resulted in, and his decision making processes in his work today.

Listen here:


Thanks for joining us on Decision Dialogues. We’re thrilled to have you along. My name is Mark Willoughby, and I’m a Principal and Wealth Manager, and the Chief Operating Officer of Modera Wealth Management, LLC. Today, my partner Tom Orecchio, the Chief Executive Officer, Principal and Wealth Manager at Modera, and I, will be chatting with Christopher Hliboki, an experienced estate tax, business, and real estate attorney; founder and owner of a successful legal practice serving, clients in the New Jersey and New York area. Welcome, everyone to the show, and I’ll hand it over to Tom.

Thank you, Mark. Chris, great to have you.

Hello, Tom—well, thank you very much for having me.

So full disclosure, Chris and I know each other since before we were teenagers, Chris, we’re just gonna go over just some general questions about how you got started and what you do. So why don’t we start with what line of business you favor most, and how did you get started in that?

Well, I’ve been running my own practice now for about 22 years. And so I do a lot of work in the tax and estate planning area. In addition to my law degree, I have my master’s in tax law. So in addition to the estate planning and tax controversy area, I also do a lot of general corporate work and transactional work, we do a fair amount of real estate, and we do some commercial litigation work from time to time as well.

So Chris, when you got out of law school, I know that you were working for another firm. What caused you to go out on your own?

That’s an interesting question, because there were a combination of factors. Number one, I’d just applied and been accepted to the NYU LLM program at the time, and my firm was going to pay for it, and they reneged. So that was a jumpstart for me to realize that my time there was very limited. At that point, my wife’s career was starting to take off, and she, you know, I got to give her credit—she really supported me in the decision to go out on my own. And, you know, timing is everything. At that point, when I left, I didn’t have clients, one, and on top of that, I was leaving my desk every day at 4:30 driving to New York City to get in my seat at NYU at night from six to ten at night for three nights a week. You know, I look back on it now, and I just don’t even know how I did it, but I’m sure glad I did, because it was one of the best decisions I ever made.

So Chris, for our audience, can you describe what the LLM program is all about?

Yeah, sure. You know, it’s a master’s of tax law, so it’s like going back for another two and a half, three years of law school, but specializing in tax.

Okay, and this, I’m assuming that comes up a lot in your practice.

Yeah, you know what—one of the things that I was really impressed with—the partner that I was working for, when I was an associate, he had his LLM in tax. And one of the things that really impressed me was, he just thought on a different plane. And you know, it’s one thing to do a business deal, it’s another thing to look at it from a tax perspective. So I knew very early on, that’s what I wanted to do. So it was just a question of finding my way into the tax program, and you know, putting the time in to go out and study for the LLM.

So 22 years ago, you go out on your own, how long did it take before you felt you started to get traction, enough that you can make a run at this?

You know, every day, even 22 years later, I think the same thing, Tom—even if the phone doesn’t ring for a couple hours in the office, I still get a little bit anxious. But you know what, it was probably about two or three years in, and I started landing some significant clients at that point. And when you really know that you’ve done a good job and things are starting to take off, is when you have clients who are referring clients to you because they told you you’ve done a good job. That validation was really important to me.

That’s great. So when you go out on your own, and you’re responsible for all parts of the business, not only bringing in business and serving clients, but running the actual business, what do you find to be the hardest decisions about running your business?

You know what, the biggest concern that I always have from day one is time management and efficiencies. I will tell you one of the greatest things I ever did was hire my secretary, Rita, because she’s been with me for almost 21 years now, and she puts just a wonderful face on my firm. The clients love her and she wears so many hats in the office. I have to tell you, it’s like having a second wife because we bicker sometimes like an old married couple, but she fantastic. And, you know, I’ve been part of her family now—I’ve seen her kids grow up, and now she’s a grandmother three times over with a fourth on the way, and it’s just, it’s been a great relationship.

That’s great. You mentioned that time management’s a difficult part of the business. Walk us through a typical day. What happens?

Well, there is no typical day—every day is different. And one of the things that I try to do every day, or the night before I walk in the office, I’ll have a list of 15 or 20 tasks that I want to accomplish. I’m a big list guy like that. You know, I walk in the office, especially on a Monday morning, by 10:30, there are ten other things that have been added to my list at that point, because so many things happen between a Friday and a Monday. We get phone calls, and I throw my agenda out the window for the day, and I have to start reprioritizing right away. And that’s the biggest challenge, I think, on a day-to-day basis is that you just never know what’s going to happen. You know, things go wrong, opportunities arise for clients, and you have to jump on them. You have to prioritize—you’re constantly reprioritizing.

So let’s stay with this for a minute. Because we have a lot of clients who are business owners, and I’m sure that we have adult children of clients who are aspiring business owners. It’s difficult to separate your work from your life and your family. Do you find that it could easily be a seven day a week job? And if so how do you separate it, or do you separate it?

It definitely is. If you’re going to be a business owner, you have to be totally invested in it, and it is a seven day a week job. Without a doubt. I’m very fortunate that my family is very supportive of it. My wife, as you know, Tom, works a very big job herself. So she perfectly well understands that my hours are whatever they need to pay. But I gotta tell you, I mean, I don’t struggle with it, only because I don’t mind doing the work, and I don’t mind doing the work at all hours. I try to balance it the best I can. But it seems to work. I don’t really have a big issue with it.

Does the same apply to your personal finances and your business finances? I know that you know, your work’s tied very closely to your life—do you find that there is a bit of an entanglement between your personal assets and finances and your business finances?

No. You know what, we keep them entirely separate. I never make my business decisions based upon my personal finances, or vice versa. When it comes to my business, the biggest challenge, you know, obviously, is staying on top of clients and, you know, in terms of billing and collections and all that. And it’s a constant challenge for I think any small business owner, is to keep the revenue coming in the door. But I have also found that if you are upfront with your clients about it, and you are consistent with your clients, concerning billing and collections, that they are very, very responsive, and they’re very appreciative of it.

As a small business owner, and as an attorney who practices a lot of areas, I’m sure that there are days that you enjoy, and there are days that you don’t enjoy—and there are areas that you enjoy working in and other areas where it’s just part of the job. What’s your favorite?

You know what, my favorite really, is dealing with my business clients. And one of the reasons why is I just enjoy seeing these businesses go from startups literally through to sale. I’ve been along with that evolutionary process with a number of clients over the last 15, 20 years. Or I have clients walk in the door, you know, 16, 18 years ago with a piece of paper and a check for $200 to start their business, and before you know it, they’ve got five centers, they’ve got 65 employees, and they’re selling it out to you know, whether it’s a private equity firm or a strategic partner. And to see that growth and to be part of that along the way, is really—it’s gratifying from a professional standpoint. And I kind of feel, you know, part of, as a small part of that success, I really enjoy it.

Sure. 20 plus years into this, if you could look back, and you started over, what would be the one thing you would do differently?

The only thing I probably would have done a little bit differently is I probably would have hired an associate earlier on. I’ve gone through a series of paralegals, I’ve gone down the route, several times, with associates. The problem for a small firm like mine, is that associates—they come and go, and there’s no consistency. They come in, they learn, then they’re onto the next thing and they move on. And that’s that’s the biggest challenge for a small practice like mine.

So this is a difficult question, and it’s a two parter. What is the best advice you ever received—and if you can recall—what’s the best advice you ever gave?

The best advice I’ve ever received: I was sitting in court one day and I was contemplating whether or not to go out on my own. And I was there with another solo practitioner and we were on opposite sides of the case. And we were sitting outside of judge’s chambers waiting to basically have—I was waiting to get my head handed to me, to tell you the truth. But I asked him, I just out of the blue, I said, “Pete, how do you know when it’s time to go out on your own?” And he said, “You never know. There’s never the right time,” he said. “But you have to trust in the process,” he said, “because when you are on your own, the business will come,” which is a very hard thing to have faith in. But I will tell you, he was 100% right. And when I did finally go out on my own, he was my first phone call. He referred me a ton of business. And I’m happy to say, he actually went on and became a respected judge here in Bergen County.

That’s great! And how about the best advice you’ve given?

The best advice I’ve given? One of the things that I tell all young attorneys and law school students who I come across is, never take a case or a matter solely for the money. Because when you do that, you will end up with a dissatisfied client. And you’ll end up with a whole bunch of problems. You have to be—you just never do anything based solely on the money in this business.

That’s good advice. That’s any business. So Chris, I know you pretty well, and I know that you love to run and I know that you love to read. What are you reading right now?

Right now I’m reading The Splendid and the Vile by Erik Larson, which is about Churchill and the bombing of London in World War Two. I’ve read several of his books—I’ve read The Devil in the White City, and In the Garden of Beasts. But you know, I do fall into those really lighthearted crime-type novels. I’ve read, probably, like 20 Michael Connelly books. He’s a guy who does Lincoln Lawyer. I just read Nelson DeMille‘s book, The Deserter, which, you know, which recently came out. And one of the most interesting books I just read was The Nickel Boys by Colson Whitehead. It’s about a reform school down in Florida back in the Jim Crow era, and my kids had to read that for school, and so my wife read it as well. And she’s like, “You’ve got to read this book,” and I did. And it’s an excellent book. I just happened to find out that he was actually on 60 Minutes about a month ago. So I watched that, because it was a really impactful book for me.

So what do you think has been your greatest business success over the years?

You know, I think it touches on a little bit what I talked about earlier—it’s those clients that, you know, that we started with 15, 20 years ago, you know. Clients that I had when I was an associate that actually moved over into my firm, when I first started out. The fact that they were with me for so long, and the fact that we were able to—and again we’ve moved into the second and third generation with those clients. That to me, feels like the best success that I’ve had, because, you know, we get clients in, they’re not one offs, they stay. We develop that relationship over a long period of time. I treasure those relationships. That’s really the base of my practice.

And how about your biggest personal success?

You know, I think my biggest personal success—I mean, setting aside my kids, of course, and my wife—but my biggest personal success, I think, is being able to juggle it all. You know, one of the things I never compromised, all throughout this process, was getting the opportunity to spend the time to be there with my kids. And you know, that’s the greatest thing about being a solo practitioner, is you do get that bonus time where you can say, “You know what, I’m at four o’clock in the afternoon. I’m going to go see my son play baseball today.”

I was hoping you were gonna say it was when we put together that travel baseball team.

Yeah, those are special moments and ones you never get back, and I treasure all that.

It goes fast. It goes really fast.

It does, it does.

So just to wrap up here, just a couple quick personal questions. Tell me when you think you know it’s time to pack it up.

Wow. You know, if you asked my wife that question about me, she’d say, “when they’re wheeling me out, okay, in a box.” But you know in reality, I don’t know if there’s ever really a time that I would say I would be ever ready to pack it up. I think that there’s a time to ratchet it down, and I think there’s a time to slow it down. I can’t ever imagine stopping cold—I just can’t see that. I don’t see the reason why I would ever do that either.


I enjoy it. There are not a lot of lawyers out there that will unequivocally say that they really enjoy what they do. But you know, I found a space in this practice and a niche here that I really enjoy.

Well that’s good. So tell us something about yourself that our listeners wouldn’t know or wouldn’t expect.

Hmm. Well, one of the interesting things, I think, from a personal standpoint is—I would love to be able to tell you that I’m a good cook or something like that, but I’m not. But one of the things I’ve learned to do over the years, because I just have a sweet tooth that goes beyond—I love my sweets. So over the years, I’ve really taken up baking, because I love to bake. And the other thing that I do all the time, which is just the biggest sunk cost around this house—I love to put a vegetable garden in every year. I spend hours out in the vegetable garden. And I’m constantly battling—


Critters and all the deer and all the fungus and everything else that goes along with trying to garden. But you know, I don’t have a big plot where I do it, but I really enjoy it. I probably spend, I don’t know, like $1,000 a year to grow $100 worth of produce, but it’s relaxing to me. I really enjoy it.

I’d also bet the spend about $1,000 a year on ice cream, because I know you’re a big ice cream fan.

Oh, yeah. That’s for sure. If there’s one thing I bent my wife’s will to, that’s ice cream.

So last question for you. What is the last non financial related decision that you’ve made in the last couple of days?

Well, you know what, every morning when I get up, I really—I just go straight to the coffee machine. I have to have my coffee. There’s no way I can even function without that first cup of coffee in the morning. But the first thing I reach for after my cup of coffee is, I have to have a piece of fruit every morning. My wife tells me, she asks me every day, when she goes to the grocery store on a weekend, “What do you need from the store?” I just asy, “You gotta buy fruit. I need to have fruit.” So it’s always a question, “Am I having a strawberries today, am I having a pear today, am I having a banana today?” You know, I have to have a piece of fruit in the morning. So today was a banana.

That’s great. Well, it’s been a pleasure having you on and thank you so much for taking the time to share your experiences with our audience.

Tom, thank you so much for having me. I really appreciate it.

And thanks very much to Tom Orecchio and to Chris Hliboki for letting us listen in on their conversation. We appreciate their time and perspectives. And thank you for tuning in. We hope you’ll join us next time on Decision Dialogues for more stories from successful business owners. So long for now.

About Chris

Portrait of Chris Hliboki

Chris Hliboki is an attorney in solo practice, the owner of the Law Offices of Christopher W. Hliboki in Hackensack, New Jersey, and New York City. He has been in practice for 28 years, and has been a solo practitioner for the past 22 years. He specializes in wills, estates and trusts; business law; commercial transactions; residential and commercial real estate; and tax compliance. Chris is currently admitted to the New Jersey and New York Bar. In addition, he is admitted to practice before the United States District Court for the Districts of New Jersey as well as the Southern and Eastern Districts of New York. He is also admitted to practice before the United States Tax Court. 

Chris graduated with a Bachelor of Arts in Economics from Fairfield University in 1990. He earned his Juris Doctor degree from Seton Hall University Law School in 1993. He went on to complete a Master’s in Tax Law from New York University School of Law in 2000.

Chris is married to Lorraine, and they have two children, Bryan age 19 and Cara age 17. Chris and his family currently reside in Bergen County, New Jersey.



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