November 5

Episode 08: Words of Wisdom From Labor Law Attorney, Dan Gilmore


Mike O’Neil from Bench Builders interviews Dan Gilmore, CEO, and founder of Squire Strategies, in this episode of Get Unstuck & On Target. You’ll hear all about how Dan got himself out of a sticky situation and landed in the career of his dreams, as well as some words of wisdom he has to share with others looking to start a career in law.

In This Episode, You’ll Learn… 

  • How Dan went from passing the bar in Texas and Tennessee to relocating and taking the bar in California
  • The trials and tribulations Dan went through that led him to start his own law firm — Squire Strategies.
  • Words of wisdom for those looking to begin a new career as a lawyer


“Make sure people know what you do.”  – Dan Gilmore

“Don’t limit yourself to what you think you should do or what people tell you that you should do. Keep an open mind, and have faith in yourself. Have courage and don’t let fear prevent you from going for that.”  – Dan Gilmore

“Don’t feel like you don’t have any options. If you feel stuck, then there’s always going to be a way to move on, but you’ve got to have your eyes wide open to what those opportunities are, and to pursue them.”  – Dan Gilmore

Links & Resources Mentioned…

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Read The Transcript

Mike O’Neill:  Hello and welcome back to the Get Unstuck & On Target Podcast. I'm Mike O’Neill with Bench Builders, and we're speaking with successful leaders to uncover tips to help you break down the barriers that are keeping you or your business stuck. Joining me today from Chattanooga is Dan Gilmore. Welcome Dan.

Dan Gilmore: Thank you, Mike pleasure to be here.

Mike O’Neill: I am delighted you're with us. Actually, I should probably say welcome back because Dan has the distinction of being our only repeat guest on our webinar series, and you'll soon see why. Dan's been practicing labor and employment laws since entering private practice in 1990.

He's the founder and attorney at law of Squire Strategies. And I've asked Dan to share his experience of being stuck professionally. And what did he do to get unstuck?

Dan welcome. If you don't mind, I'd like to go back and pick up in your college days. I understand you graduated from Baylor university.

Is that right?

Dan Gilmore: That is correct. Second Bayer's both undergraduate and law school. And in between those two experiences, when I met my wife in Washington, DC, which put me on a different course in life, which, never turned back.

Mike O’Neill: You mentioned you went straight into law school. What led you to go to law school?

Dan Gilmore: A big influence was my father who was an attorney is an attorney. He's no longer practicing in Dallas, but I grew up around him around, his partners, his associates. He was on the city council in Dallas. I spent a lot of time, around city government and he was a great influence, in my decision to pursue law. And my practice is very different than his plus, but that is, I think a direct result of, seeing him, as an attorney growing up.

Mike O’Neill: What type of practice did he have?

Dan Gilmore: His is primarily city law, municipal law school law, probate law, family law... did a lot of adoptions. And that was one aspect of his practice.

I've told him over the years, I'm very jealous about because he has people that come up to him years and years, decades later saying you were the one who did my adoption. And thank you so much. so nothing he's never practiced employment law, or even traditional labor law. But I did a lot of different areas other than that. 

Mike O’Neill: You went to law school. You aspire to be an attorney. What led you to go into the kind of work that you ended up going in labor and employment law?

Dan Gilmore: I should add that, right after law school extra during law school, I was, in the Marine Corps, commissioned in the Marine Corps in 1983.

So my first years of practice were as a judge advocate. Both as a defense attorney, eventually prosecutor. My wife's family had retired at Chattanooga. I'm a Texan as, didn't mention that I haven't gone to Baylor. I should have, I'm a Texan by birth and my wife's a Tennessean. And, I looked both in Texas and here, when we left the Marine Corps and had an opportunity here with a law firm that, was a great fit.

And about a year into that experience, going from the litigation department, which is what I've been doing almost entirely in the Marine Corps at that point. There is an opportunity in the labor and employment department, which is very small at that time in that firm. And I made the move in 1991 into that department.

And I've been practicing that, area of law now for almost 30 years.

Mike O’Neill: Now, that was a relatively large practice. Is that correct?

Dan Gilmore: The firm itself was the, that practice group was. Oh, that's how maybe eight attorneys. And it grew at one point that from two close to 40, and I'm not sure what it is now. But it was a relatively small group at that time.

Mike O’Neill: So as a recently minted lawyer, was this a good opportunity to be part of a larger firm, but a smaller group that specializes in labor employment law. That affords you opportunities you might not have gotten if you had a, bigger firm?

Dan Gilmore: Yeah, I think so. And at that point, that firm had originally one office. in one city, it grew into three by the time I moved to California, we'll be talking about here shortly.

But it was like, it was a good, group of attorneys. People I got along with very professional and an area of the law that I not had experienced it at that point, but just had an opportunity to move into it, and really have enjoyed over the years, the kind of work that involves, which you know very much about being, having your career in the HR world that has been throughout my career the primary connections in with my clients. There's those in the HR role in particular?

Mike O’Neill: We share that. So if I understand correctly, you were practicing and an opportunity came for you to, you've gone from Texas to Tennessee and now comes California.

Tell us a little more about that please.

Dan Gilmore: I've been here in Chattanooga for about six years and it really, I just, made partner, after six years, but at kind of a plateau, and I didn't really see, the, opportunities beyond, that, point in my career. I'm not from Chattanooga, as I mentioned and Chattanooga, like a lot of places, it's very much a city of, where he went to school, meaning high school and a lot of cases.

I was searching for some opportunity to expand when I was doing, not leave the practice of the firm, but an opportunity to, bust out of that, stalemate, as I felt like I was to in a rut or kind of a holding pattern, in my career. And so after the firm had asked maybe two other attorneys, they came to me and said, would you be willing to move to California?

You live in California. And if you can pass the bar exam in California, we'll move your family. So first year by yourself, if you can pass the bar exam, which for those who know the bar exams, California is notorious along with New York and some others as being difficult. At that point, I had taken a pass, the Texas and Tennessee bars.

And how it was not necessarily eager to roll the dice again. but it was an opportunity to, live in a part of the country. I'd never lived before to practice an area. As being an HR California's notorious for its, employment law environment, the litigious nature of it. The laws themselves are very unique, very, progressive.

So it was an opportunity to practice in that part of the country and throughout the west. But, at a risk of if I got out there and failed, the firm was counting on me. It was the firm's largest client that, wanted somebody out there. And so I had to overcome a lot of fear to do that. And that's something I've spoken about over the years in different contexts, but this is in my life, a very prime example of number one, being mindful of opportunities, being opened opportunities, but not being paralyzed by fear, and overcoming that fear, which is not easy, was not easy.

Then, I should add that, fortunately, I passed the bar the first time through. The family moved out the next year. But that first year there was, challenging being by myself. I cut back and forth to visit the family.

But it was a kind of a hail Mary for me at that point, that if, it worked, great, but there was a lot of, risk professionally that if, I didn't succeed and I would've put myself even farther behind, at least that was my concern.

Mike O’Neill: So, Dan let's unpack some of that a little bit. What I understand you to say is you were approached, but you said that at the time that you were approached, you used the word you felt like you're a little bit in a rut.

Did you feel like you were somewhat stuck?

Dan Gilmore: Yeah. And that's when you mentioned the theme of this podcast, that situation immediately came to mind. I was stuck, as I mentioned, I was very proud of the fact that I just made partner. but the opportunities in Chattanooga for me, within that firm were not clear, not being from here.

So I was looking for, how can I break out of that and create a professional life myself. And as it turned out in a process, a very rich, personal life for my family. The time of California, we ended up being out there for 10 years was, was instrumental in all of our lives. And, but that was not a foregone conclusion.

When I got on that plane in August, 1996 and hit it out there with my suitcase to give it a shot.

Mike O’Neill: You said yes, but it came at some risk. You had just been made partner. Yes, you had passed the bar for Tennessee and Texas, but you had a pretty long bit of work that you had to do to prepare for and pass the California bar, but you must have felt when you said yes, that there were a lot of eyes, they say the eyes of Texas, but a lot of the eyes of the firm were on you in this move.

Is that a fair statement?

Dan Gilmore: Very much because this client. As I said it was the largest client. The firm, had grown weary of having attorneys travel from California, from, Chattanooga to California. All the, all of the services we were providing were from Chattanooga. So it was travel time of all. This is 96 where, communications weren't where they are now.

And cell phones, mobile phones were just becoming a part of our lives. So access was something they said either "you send someone out here." My firm sent someone out here to live out here, practice out here on the West coast, but we're going to use a local council. And that was always our worst fear.

Throughout my time with Fisher, with that client serving that client is that we would lose the local attorneys who are there living there, practicing there, or been there forever. So that was a big concerne of ours and my going out there was the firm's effort to try to hit that off.

Mike O’Neill: Can you describe some of the head process as you went through the thinking process, the decisions to do that, you weigh on the pros and cons, but you said there's a, there's an emotional aspect of this.

And that is the fear of saying yes and what that entails. Can you share, what were the kinds of fears that you were experiencing then?

Dan Gilmore: The fear was that, the, what ifs. What if I got out there and, did not, could not pass. And, I just, that wasn't a certainty that I could, I, I haven't at that point, I'd taken the Tennessee bar and 1990.

So it'd been, it would have been seven years by the time I took it and, February of 97. And so a lot of that I've been away from. Any lawyer will tell you that when you study for on the bar exam, that much of it has to do with practicing law. And so a lot of it, I hadn't really spent much time, focusing on or spending part of my practice was not on one of those issues.

And so that was not something that, was a given. And so in my mind, it gives me what if I get out there. I don't get the results I want. And then what happens? I come back with my tail between my legs or beg for chances. Another chance of there was not, I didn't see it as having more than one chance to do it.

Mike O’Neill: So you did feel like your back was against the wall. You knew you were going to be out there solo without family for a year getting established. Preparing for the bar.

At what point after you passed the bar and your family got out there, at what point did you begin to breathe? A little bit of a sigh of relief.

Dan Gilmore: That fall of 98, we bought a house in Pasadena. I've been out there for about a year and a half, and the kids were into their schools there. We felt good about the school situation. I was in a good, thought flow with the client, out there. And as I've shared with you before and your, listeners, that is, those early days in particular with the origin of the name of my practice, which Squire Strategies.

Squire Strategies came from that, experience, in those early years. So it was probably within a year, and a half, I felt okay, this is going to work for how long nobody told me going out, this is going to be for five years, 10 years. That was something that was very much, open-ended And which maybe fast forward 10 years of when the decision was made to come back to Tennessee, which is a whole different set of decision-making at that time with schools and, the work and stuff.

But at that time, to answer your question about a year, and a half.

Mike O’Neill: I want to come back to Squire strategies in just a moment. You're in California. You spent about 10 years out there. You said that the decision that led to you throwing your name in the hat was a feeling of, I might have topped out and this office, because I don't have the same connections as some of my colleagues.

Do you ventured out, you became, I don't know what the right term you use in the military to talk about having an embedded group, but you came in attorney, within the company, almost as if you are an integral part.

Dan Gilmore: Okay. That's exactly right. I learned the term out there, Mike and I had not known before of captive counsel.

I was a captive counsel. My only client there was, that client. I worked in their administrative offices. I worked alongside all their executives. My assistant was an employee of that company and I was by all appearances and employee of that company. People who didn't know the arrangement, I'd carried an ID badge with me and my office was there.

They, most people thought I was an employee of that company, but I was throughout that time, essentially on loan from my firm.

Mike O’Neill: So you made that move. You were there for 10 years, and I know that at some point. You opened Squire Strategies and in interest of time, we may not have chance to do all of that.

But what took you over time between being a captive counsel in California to opening Squire Strategies. What is it that, triggered that?

Dan Gilmore: That was a couple of different, significant, decisions that, led to that first was to come back from California. We, there was never a time they said you've got to come back.

So it became apparent to me we needed to take the initiative. The girls I've got three daughters and one was in college, two ran between middle school, high school and at that stage. So I was here's the window time. I've got to do it now and just did. Went back to Nashville for three years, then I was recruited by a different firm, a firm back here in Chattanooga.

So came here for about four years and after four years in that firm, began to become more and more involved in an entrepreneurial community here, startup community. And that, mindset was something that not had a lot of interaction with the client I'd work with all that time in California, it's been around for a hundred plus years.

So it was, not a startup world. So in that process became more and more interested in doing something, on my own, which is a whole different. Yeah, a leap of faith. And because at that point it wasn't an assurance that needed. The clients that I worked with at that firm, would follow me or if I, want to be professional about it and not, I want to leave under good terms.

And so some did follow me, but for the most part, it was, up to me to develop that business. And, I just thought that the lure and the, appeal of being my own boss, having my direct connection with clients without having to enter any intermediary relationships to deal with was very appealing.

And that's what I enjoy most about what I do now. my relationships with my clients are direct directly with them. And if, I do well, They know, if I don't it's nobody's fault but my own, and fortunately it's not happened. But it was, I think, a direct result of being more and more involved in that part of the community here in Chattanooga that, opened my eyes to that possibility when the time came to make a change.

Mike O’Neill: You mentioned that the move to California was a bit of a leap of faith. And you mentioned the opening of Squire Strategies as a leap of faith. Do you think those two leaps feed into your desire to work with entrepreneurial-minded folks?

Dan Gilmore: I think very much. And, especially my creation, my own practice, I feel like it gives me credibility to that part of the community that I'm not just saying here, go for it and you can do it, but I've done it myself.

And my experience of California, it's been very helpful, for those larger clients that know that I've essentially been in-house counsel during that period. But the entrepreneurial community, the fact that I've done this for my own, that I've ventured out and taking that leap. And it's a scary leap.

I just, for many, years, Mike, I could not imagine doing this on my own. I just thought, how could I ever do that? It was just a thought that just come and just come terrify me. I'm on to something else, but it's, but when that time came and I, have, one person in mind who shoved me over that fence into the decision and two things you told me, and they've stuck with me forever is number one, this is what you are leaning to do.

I would encourage you to do it. And for two, and this applies to anybody in business and what you and I do, what any of our listeners do is make sure people know what you do. And that is, remind myself that all the time.

I'm a lawyer obviously, but what do I do? What kind of law do I practice? Who can I help? How can I help them?

If those who want to help me are not aware of that and don't know if Dan prepares wills or if I'm a patent attorney, then they can't help me. And that's something that, I'm very dependent upon my networks, my referral networks, my hopefully mutual relationships. but it's important for those people to know what I do and remind them what I do.

So that is something that, This opportunity and the opportunities you've invited me to be under webinars, previously this year, really appreciate it. That's really, helps me, help those, that, especially those I've not had contact with before, make them aware of what I do and how I do it in my, philosophy towards the practice of law.

Mike O’Neill: Our listeners might know that my professional background is very heavy HR. And so I had counsel on speed dial. And I've told Dan already this privately, but I can say it now publicly. I wish I knew Dan at the time that I was in corporate HR, because he clearly would be on my speed dial. He strikes me as someone who understands the law very well.

But more importantly, he's able to explain it to me and my team when I was in corporate HR in a way that we could grasp and act on. And that's a unique quality.

You've got another unique quality. Dan I'm, I, I'm a big fan of yours and that is you have a servant heart. And I know that you do tend to give back.

One of the things I know you do is you're adjunct at University of Tennessee at Chattanooga. And you mentioned that someone came alongside you and gave you some good guidance, as a mentor. And I know you do that.

What do you share with those folks coming to you and say, Mr. Gilmore. Tell me what I should know if I want to do the kind of work that you do. What are the kinds of things you share with them?

Dan Gilmore: Mike, it brings up a good point of one of the main reasons I teach and I enjoyed teaching as an adjunct. Is those relationships with the students and helping them, not only during the semester, but afterwards, and I've got. Even once student, this semester, before the semester started, came to me and said, would you talk to me about why you're doing what you're doing and give me advice.

And I love can used to do that. And the messages I. Tell a lot of the, especially if those looking at law school is that they're keeping an open mind of what you can do. The law degree. My mother's father I'm told, my father when he started law school, back in the fifties, you could do anything with a law degree except practice medicine.

And I tell students that, so don't get tunnel vision over, what you may see on TV. If you're thinking about law school, a lot of things you could do with that. Or even graduate degrees. A lot of them asked me about graduate school opportunities and what they should think about. And so the themes with those conversations are be, open-minded be mindful of what's out there.

Don't limit yourself to what you think you should do, or what people tell you, keep an open mind and have faith in yourself and have courage. and don't let fear prevent you from, going for that. My youngest daughter right now, in law school online, like everybody is these days and I've been so proud of her giving her that kind of vibe.

I, my wife too, over the years of just, if that's what she wants to do, go for it and just do what you have to do to get there. And that's what I tell my children have so much children now tell my students and anybody outside of just in the business community, I'm often asked just to provide, advice to, those who.

Look at me as a potential mentor, either officially or not. And, and I, appreciate that. That's a great compliment. Mike being servant, the servant attitude. Sometimes, I feel too much, I can't say no to people and, but that's, I'd rather be that way than in a type of person who's who has no interest in helping others, because I certainly benefit from that from other people in this community and beyond the community of those who want to help each other succeed. That's been helpful for me and I want to pass it on to others as well.

Mike O’Neill: That comes through loud and clear. The theme of this podcast is we're asking leaders to share examples where perhaps they or organizations they lead got stuck.

And you're willing to be vulnerable with us the listener to share examples where on more than one occasion, you found that you were stuck. To get unstuck you had to make bold decisions, that didn't necessarily only affect you. But if that did your family.

Dan Gilmore: Very much.

Mike O’Neill: Yeah. And that you acted, and, in such a way that it was a leap of faith on more than one occasion, and there is a tendency for people to think when you own your own business.

Oh, it's so much easier. It does has an advantages. I'm a fellow business owner, but there are also disadvantages and I applaud what you have done. And more importantly, your willingness to share what you have learned along the way. As we wrap up our time together. Dan, can you think of anything that you would like to share with our listeners that we haven't had a chance to cover?

Dan Gilmore: I think just to reiterate, I made a note to myself before we started, of mindful plus courage in that those two attributes are something that I don't, I've not always lived up to myself. My wife is always saying, widen the lens, why the lens look at things broadly. And that's what I feel that people should, always attempt to do, and identify opportunities.

And don't feel like you don't have any options. That's the things that, if you feel stuck, then there's always going to be a way to, move on. But you've got to be, have your eyes wide open to what those opportunities are, and to pursue them. Yeah, my wife has been a number of situations of, overcoming fear.

I did a program for years ago here for startup week, during startup week about fear. And I well far too many examples, but hopefully most times overcoming it. So that's my words of wisdom. So to speak that I'd like to pass on to those listened to what we've done today.

Mike O’Neill: Very, well said, Dan, if people want to reach out to you and connect with you online, what's the best way for them to do that.

Dan Gilmore: Best way is to, reach me. My website is You can reach me through the website. You can reach me through LinkedIn as well and my email address, you want to email me directly as

Mike O’Neill: We'll try to include those in the show notes as well. Dan, I was looking forward to our time together today.

Thank you again for your willingness to share as openly as you have. So thank you.

Dan Gilmore: Thank you very much, Mike. It's my pleasure. And, I look forward to meeting you in person one of these days, we talked about it. We're going to pull it off.

Mike O’Neill: We've had, you've been on our webinar twice. I've been on a podcast, we've had a number of other conversations. I too, looking forward to that, let's put it on the calendar.

So if I might, as we wrap up, I want to thank our listeners for joining us for this episode of Get Unstuck & On Target. We've lined up great guests like Dan, that I'm sure you'll enjoy getting to know we're uploading the latest episode every Thursday, and we hope that you'll subscribe to this podcast and invite other leaders to do the same.

The easiest way to subscribe is to go to your browser and type again, or go to our website So again to our listeners. Thank you for joining us. I hope you've picked up some tips that help you get unstuck and on target until next

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