One Lawyer’s Journey from Law Practice to Public Service

Episode Notes

Transcript

Announcer:
New approach, new tools, new mindset, new solo.

Adriana Linares:
We’re going to start today’s episode with a riddle. What came first? The lawyer or the CPA, and how did it hatch a county controller? My guest today is Phil Diamond. He is the Orange County Controller in Florida. And I’m Adriana Linares, the host of New Solo. I’m pretty stoked to have you on the show here, Phil. Welcome.

Phil Diamond:
Thank you. Great to be here.

Adriana Linares:
I love talking to lawyers or someone with a law degree. I’m not sure exactly how to describe you yet, who decided to go in a different direction with their law practice. So I’ve got a bunch of questions for you, but let’s start with the beginning. What came first? The CPA or the lawyer?

Phil Diamond:
The CPA. CPA was necessary to become a lawyer because after I graduated from college, I didn’t have a lot of money. And I went to work for an accounting firm, decided it wasn’t for me, and I wanted to go to law school. That was always in the back of my mind, but I needed to do something and raise some money to pay for law school because like I said, didn’t have a lot of money.

Adriana Linares:
Like many of us don’t when we come out of college. Where did you go to college and did you get an accounting degree? So did you start there?

Phil Diamond:
Yeah, I am a proud and loud graduate of the University of Florida.

Adriana Linares:
As you all are.

Phil Diamond:
Yes. The loud part, I assume

Adriana Linares:
You mean.

Phil Diamond:
Yes.
But proud too. But yeah, I went there, graduated with an accounting degree. I don’t know that I took my accounting studies as seriously as I should have because I wasn’t sure it was going to be what I was going to do for the rest of my life. But what I did know was that it would probably be a path or a way to accomplish a lot of what I wanted to accomplish. That was my father’s advice was I had other ideas about majors and he said, “You go with accounting, you can always get a job and pay to do stuff that you might like to do more.”

Adriana Linares:
Well, I think that sounds like great advice. And I think a practical degree like accounting might be better than some other degrees that many of us get. Okay. So you get your accounting degree, but you weren’t like, “I love this. I’m going to love rolling around in numbers for the rest of my life. What will I do?” What made you look at law?

Phil Diamond:
Well, I always had an interest in it and I realized that I liked some of the things with Law more, like writing and reading and speaking and the idea side of things as opposed to what I was doing as an accountant, which I just didn’t enjoy that much. I was doing auditing and – Sexy work, Phil. Sexy

Adriana Linares:
Work.

Phil Diamond:
I always heard that all the time. Especially when you’re the junior person working at a CPA firm, you get the work obviously that no one else wants to do. I didn’t enjoy it. I just didn’t enjoy it. I didn’t see how it helped people. I didn’t see it as being really interesting. Auditing work in a CPA firm. And there’ll be a part of the story later on about auditing work and how I have found a different part of auditing, which I think is just awesome.

Adriana Linares:
Yeah, a little teaser. Okay. I can’t wait to hear it. A little, what do they call that? Foreshadowing. But okay, so you started at a CPA firm, but then you decided to open your own.

Phil Diamond:
That’s right. And I did that. And that was something that by doing that, I could do accounting work while I was in law school. And oftentimes when you’re in law school, a lot of demands on your time, a lot of structure. So a lot of the work I would do at nighttime or on weekends or
Whenever I had a spare hour, which often happens at night or on weekends. And so that was a chance to do it. And my clients, they didn’t care what time of day or what day I did it. They just wanted me to do it right. I could charge a reasonable rate. I was cheaper than more established larger CPA firms. And a lot of the work I was doing, be it tax returns or compilations, what we call write-up work, I was the right skill level for them and I could charge a fee that they could afford, worked with a lot of small businesses. I remember to this day, I loved a lot of the businesses. I remember a yogurt shop and a restaurant. And I remember one of my law school buddies opened a restaurant and we would trade accounting fees for great food. And as someone who liked to eat and still does, that was a good combination for me.

Adriana Linares:
I love it. Okay. So you graduate from law school and then what happened?

Phil Diamond:
Well, I got a job with a small law firm in Orlando and I practiced tax law. I got into EriISA. I got into estate planning. I got into corporate law and I enjoyed that. I made partner there. And after about eight years or so, I was contacted by a friend who worked at the Carlton Fields Law Firm. They recruited me.

Adriana Linares:
No schlep of a firm.

Phil Diamond:
No, great firm. Great firm, that’s for sure. And I worked there for 22 more years.

Adriana Linares:
Wow.

Phil Diamond:
I did 30 years in the law. I like to tell people I’m a recovering attorney now.

Adriana Linares:
Right. And did you find that your CPA accounting and maybe even your entrepreneurial skills were helpful, especially when you were a younger lawyer? Were the skills interchangeable? Did you find it was a great combination? So you’re like, “Dad, you were right. Great choice. And now I have these two very honorable and interesting skill sets, but they mix.”

Phil Diamond:
Oh, absolutely. A lot of people I worked with were small businesses and I think understanding how it works, understanding some of the real nuts and bolts stuff, which you do as a

Adriana Linares:
CPA

Phil Diamond:
Had a lot of value to people. And I think understanding a lot of that helped in looking at contracts or writing contracts or looking at documents. So I think it was incredibly helpful.

Adriana Linares:
It certainly sounds it. What was your favorite area of law, if you had to pick one? And did it end up sort of leading to you deciding to run for office eventually and get into public service? I don’t know if they’re related, but I do want to know if they are.

Phil Diamond:
Oh, that’s a great question. I really loved helping clients. I really got a lot of satisfaction out of helping people achieve their goals or to get good results on something I was working on. My favorite part was probably when I got involved with any IRS controversies, tax court, and that’s something that you can really make a difference for your clients. I think good representation makes all the difference in the world in that area. I think the IRS respects that. I think the tax court respects that. You can really do a lot for your clients. Oftentimes you can show them exactly what value that you have brought to them. And I just enjoyed that just because I find it interesting. I enjoyed that.

Adriana Linares:
Do you also have your LLM then? It sounds like that’s obvious.

Phil Diamond:
Actually, no. It’s something even to this day, I toy with the idea of going back and getting that. I took a lot of the courses at the University of Florida Law School that you need for that, but I don’t have it. And it’s one of those things I think it’s kind of unfinished business that I’d like to do someday.

Adriana Linares:
Phil, I love that for you. I totally think you should do that. And by the way, I think you’d be a shoe in. You could probably just go take the test. You could sit in. It’s never too late. I should, and I don’t know if I’ve ever mentioned this, the lawyer I live with has had his law licenses from California and New York. He probably had them for about 25 years. And then when we met, he decided to take the Florida Bar. He was definitely the oldest attorney in the room or the oldest student in the room. And by the way, interestingly, this was probably six or seven years ago. He was the only Windows user in the room. Everyone else had Mac. So he did not get that law license until very later in life. But on top of that, because he had such a good time doing it, and Phil, this is the inspiration for you, you might have to take it further, he decided to sit for Louisiana because he’s like, “Oh, I forgot how fun it is to study law, practice law and get really into something.
So now I’m going to go take the other hardest bar in the country.” So I don’t think it’s ever too late. And maybe we’ll inspire some other listeners who are more mature and experienced in getting, again, like you said, unfinished business. Let’s cross that off the list.

Phil Diamond:
For sure.

Adriana Linares:
Let’s take a quick break, listen to some messages from some sponsors. When we come back, I’m going to ask you about making that transition from private lawyer to public servant. We’ll be right back. I’m here with Phil Diamond. He is currently the Orange County controller. Phil, are you the comptroller or the controller? I have a real problem with the phonetics here.

Phil Diamond:
And that’s something I probably got asked that more than so many other things, but it’s the C-O-M-P-T comptroller. A lot of people kind of say, “Which is it? What should we call you?” And I tell them, “Call me Phil.”

Adriana Linares:
So Phil, Diamond, the Orange County Comptroller doesn’t roll off the tongue as well. You’ve had an unusual combination of careers. You were a CPA, a lawyer, a business owner. And what made you turn to doing something really hard, which I think is running for an elected office?

Phil Diamond:
I’ve always had a passion for community and trying to make a difference. At one point when I was very young, I though, “Gosh, maybe I should think about running for Congress someday.” But I realized the way to make a difference is in local government. I thought that there were some issues in my neighborhood, and I think this is what inspires a lot of people to run, especially for local office, is that they may see something happening in my neighborhood or your neighborhood.
I remember that our daughter was registering for a swim class, which especially in Florida, I think every child should learn how to swim because there’s so much water, you want your child to be safe. So the city of Orlando had a really good swimming program, great teachers. They would teach your kids how to swim. And the only thing that I didn’t like about it was the fact that you had to go stand in line. This was an overnight thing. People would camp out overnight. You’d see your neighbors, the other school parents there, people would bring donuts or coffee and it was kind of fun, but you spent the night waiting in line so you could register the next day for swim programs. And I remember thinking, why don’t we do that online?

Adriana Linares:
Yes,

Phil Diamond:
That

Adriana Linares:
Seems so obvious.

Phil Diamond:
Well, and even to me, and I’m not a tech person, but I thought this is really. The thing is you got busy mothers and fathers, everybody can’t do that. People work.

Adriana Linares:
Sounds so barbaric.

Phil Diamond:
Right. So I remember talking to the mayor of Orlando at the time, Glenda Hood, and she was very receptive to it,
And we made that happen. That was one of the things that I thought was huge because government should be convenient. It shouldn’t be difficult to deal with. And whether you’re talking about registering your kid for swim classes or recording a legal document in my office or looking at something, it should be convenient for citizens. It shouldn’t be a struggle to work with your government. I was a practicing attorney at the time and I thought, just think about how much we can do for the citizens by going and being more e-government friendly, doing more like that and really just trying to make government work better.

Adriana Linares:
You have such a gentle tone and you are so obviously helpful and enjoy helping people. And it sounds like most of the parts of the law that you enjoyed were more transactional. Do you have a sort of litigatory background in there somewhere, Phil, that we don’t see where you could have been just as good in the courtroom? I think sometimes that’s an interesting topic for lawyers, especially young lawyers that kind of think they want to be a litigator and go in there and fight, fight, fight or not.

Phil Diamond:
I think every business, every person from time to time has issues, conflicts, if you will, that they have with other people or other businesses. Those conflicts need to be resolved. Maybe you can resolve them easily, maybe you can resolve them without litigation or through mediation. And I think every lawyer should have a sense of that, have a sense of how the conflict process works. Our code of ethics says we have to be zealous advocates, and you can be. You can be short of litigation. I did not do commercial litigation. I did do tax litigation in the tax court, which is a slightly different version of it. But still, you have to be ready to fight for your clients. You have to be ready to negotiate for your clients. So I think you can still be in that process. You can look at results for your clients, but at the end of the day, you’ve got to do what you feel comfortable with, and I’ve always been comfortable with what I’ve done.

Adriana Linares:
So you decided that advocating for the people and for your neighborhood was something that you really enjoyed. And is that when we decided to run for Orlando City Commissioner? Was that your first role?

Phil Diamond:
Orlando City Commission, that’s right. First time I ever ran for anything. That’s hard. It’s hard to run for office. Tell us about it. Yeah, I ran against an incumbent. I ran against somebody who had been in office for 10 years, I think. It’s a hard thing to do. It takes a lot of time, a lot of effort, knocking on a lot of doors. But honestly, that’s one of the things I liked about the campaign was you talk to people. It’s amazing. When you’re standing on somebody’s front porch,
They’re going to tell you what they think and you’re going to learn a lot. And I knocked on thousands of doors. One question I always get is did you feel comfortable doing that? And the answer is initially, no. I was terrified. I was terrified to go knock on doors. The whole idea of having the nerve to knock on someone’s door, disturb their Saturday afternoon or their Sunday afternoon and tell them that you’re here to ask for their vote, that you’re better than other people, it’s a little bit intimidating, but I really grew to love that. I really grew to enjoy that. And you can tell right away whether somebody is just being polite, they just want you to hand the flyer to them, or sometimes when they kind of step in front of the door, you know that they want to talk. It’s really interesting.
I got to meet some really incredible people, got to learn a lot. And one benefit that I’ve always enjoyed is you learn all the streets. If

Adriana Linares:
You ever

Phil Diamond:
Have any trouble finding your way around district one in Orlando, I can tell you where the streets are.

Adriana Linares:
You’d make a great cab driver today.

Phil Diamond:
I know, right?

Adriana Linares:
Without Google Maps.

Phil Diamond:
Yeah, without any of that fancy GIS stuff. So it’s great.

Adriana Linares:
Okay. So you were the city commissioner. What does the city commissioner do?

Phil Diamond:
City commissioner, at least in the city of Orlando, there’s six commissioners who serve with the mayor of Orlando. You’re the only one elected from that district, so you represent them. You’re their voice. As a result, I think to be a good commissioner, you need to be in the district, you need to talk to people, you need to go to neighborhood association meetings, homeowner association meetings. You spend a lot of nights, evenings doing that. You also, to be involved in the community, you go to a lot of community stuff, be it chamber of commerce, professional associations, you name it, you get invitations for it if you’re a city commissioner. Also, the one thing that I didn’t realize is that even when you go to the grocery store, you’re going to find that there’s people that see you and they want to talk about this. They want to

Adriana Linares:
Talk

Phil Diamond:
About that. People will say, “There’s a pothole in front of my road. I’ve called the city.” Or one person, “I know the city garbage trucks must have knocked over his mailbox six or seven times.”

Adriana Linares:
Call Phil.

Phil Diamond:
Yeah. That’s the kind of stuff you do, but then you also vote on other stuff that has a larger impact with a lot more people. And that’s part of the job too. You vote on the budget, you vote on changes to the city code, you vote on all sorts of things, and it’s really a wonderful job.

Adriana Linares:
It sounds fun. And it also sounds like, maybe I’m just stating the obvious here, all your previous experience between lawyering and CPA and advising and learning rules, regulations, and really getting into the nitty-gritty of text was incredibly helpful.

Phil Diamond:
It really is. People will say, “Oh, there’s too many lawyers involved with this. It’s a bad thing.” And I think like anything else, it depends on the person. But I think

Adriana Linares:
Lawyers,

Phil Diamond:
Given the skills you have, the fact that one of the things that I think every lawyer has is through law school and through being a lawyer, you learn to read a lot of stuff and really learn to figure out what’s important in that stuff and focus on things and understand stuff quickly. And those are all things that are really helpful. When I was on the city council, there would be probably about 200 items at every meeting you have to vote on. And obviously if there’s a contract to buy paperclips, you’re not going to read every page of that contract, but at least you’ll figure out here’s what this is. Here’s what’s important. Do I need to read this? No, I really don’t. But here’s a contract to change the whole composition of a neighborhood. That’s worth learning about. That might be worth driving out and seeing it.
Those are things, those are skills that you have, and I think it’s important for lawyers to get involved. And lawyers in general, I think have this gene inside of them that makes them want to get involved and make a difference.

Adriana Linares:
And

Phil Diamond:
They may not want to run for office. They may want to do other stuff. I’d encourage every lawyer out there to get involved. Every government has citizen committees, whether it’s a planning and zoning commission. I was chairman of the Parks and Recreation Board for the city of Orlando before I ran for office. And I think lawyers can really add a lot. I think a lot of them get involved in the planning and zoning committees. I think that’s good because I think their knowledge and background can be really helpful. They understand stuff. A lot of what governments do is governed. Well, pretty much all of it is governed by the law. Sometimes you make decisions you may not want to make, but if it’s the law, you do it.

Adriana Linares:
Sounds like you met enough people to decide that you were going to do this for a while. So I think you were city commissioner for about 10 years?

Phil Diamond:
That’s right. And I did that at the same time as I was practicing law.

Adriana Linares:
Oh

Phil Diamond:
My gosh. Yeah.

Adriana Linares:
Phil.

Phil Diamond:
Yeah.

Adriana Linares:
Busy guy.

Phil Diamond:
Well, my firm was good. We worked out an arrangement where we agreed that I would work less hours, but make less money.

Adriana Linares:
That’s usually how it goes.

Phil Diamond:
Yeah, usually how it goes, right? But it enabled me to do two things that I really enjoyed.

Adriana Linares:
So for those 10 years that was an elected position, how long were the terms?

Phil Diamond:
It’s a four-year term.

Adriana Linares:
Gotcha. So you had to run a couple more times, and then again, you met enough people. They said that Phil, he’s doing a good job. We’re going to vote for him again. And then there was an opportunity to run for Orange County Comptroller?

Phil Diamond:
Yes. That came along later. I was off the city council for four years, I think, when that occurred. I hadn’t planned on getting back into the political realm, but as it turned out, my predecessor, Martha Haney, who I thought did a great job and had served 28 years,

Adriana Linares:
Seven

Phil Diamond:
Terms.

Adriana Linares:
Holy moly.

Phil Diamond:
It’s scary math when you think about it. Long time, but she did a great job.

Adriana Linares:
Obviously.

Phil Diamond:
Yeah. So it was a matter of talking with her a few times, finding out what it entailed, learning about it, learning about stuff I had no idea that we did here. And the more I talked about it, the more I learned, the more I thought it was really a perfect fit.

Adriana Linares:
You talked a lot about getting to know people, but right back at you, they were getting to know you. So I was going to ask you, do you think in the back of a voter’s mind, they say, “Well, he’s a lawyer. We don’t need any more lawyers,” as people like to do until they need a lawyer. And they would say, “But he’s also a CPA. He’s good with numbers.” Were those important parts of your profile to the people who were making important decisions about who was going to help them run their city and the government better?

Phil Diamond:
I think you’re exactly right. I think they get to know you. I do think the CPA background is incredibly helpful from that standpoint. It’s something that there’s not a lot of CPAs involved in politics, and I wish there

Adriana Linares:
Were

Phil Diamond:
More. The CPAs I’ve met, I mean, we all have a certain kind of personality, and I tell people I’m an extroverted CPA and an introverted lawyer. It seems to be a good combination. It seems to work pretty well. This term will take me to 12 years, and if I’m fortunate enough to get reelected again, that’d be 16 years.

Adriana Linares:
Well, I have the highest of confidence in this possibility. Let’s take a quick break, listen to some messages from some sponsors, and we’ll wrap it up with comptroller Phil Diamond of Orange County, Florida. All right, I’m back talking to Phil Diamond. He’s the comptroller of Orange County, Florida. I spend a lot of time in California, and there’s an Orange County here too, and I feel it’s the lesser of, as lovely as it is. So now I always feel compelled, kind of like Winter Park. If people don’t know Winter Park, Florida, you have to say it’s not Colorado. So Phil, sometimes lawyers or someone with a law degree might worry or think that leaving a traditional practice is wasting their law degree. I feel like you have certainly convinced us otherwise because now you’ve been, since you’ve become the comptroller, full-time, you couldn’t do both jobs, so you had to leave the law practice, and that was probably one of the decisions you had to make, was leaving law practice full-time.
So what do you say to somebody who says, “Oh, I don’t want to waste all that money in my law degree and do something different?”

Phil Diamond:
Well, I get it. I mean, you work hard, it’s three years of hard work, then it’s the bar exam, and then it’s whatever you do after you get out of law school. You certainly invest a lot of time and effort in learning your craft, if you will. And it is a commitment and it’s a change. I enjoyed the practice of law, but the practice of law has changed. I forget when and where it happened, but I just remember being on a short vacation somewhere and spending a lot of time on the phone, helping clients, taking calls from colleagues at my law firm who needed assistance. If you’re in a private law firm, there’s always the economic pressures of having to work a certain number of hours of being a good colleague. So those are things that made me think, well, maybe as much as I like helping people, I like helping my colleagues, clients, whoever, I enjoyed tax law.
On the other hand, you don’t have much truly private time to

Adriana Linares:
Yourself. No, I agree with

Phil Diamond:
You. You’re pretty much available to people twenty four seven, and that’s a big commitment of your life. We all have these skills and there are some great places. Some people choose to go

Adriana Linares:
Work

Phil Diamond:
Inside of a business as a in-house counsel. Some people do government work in-house at government offices, some public interest. They work for nonprofits, and it’s a chance to use your gifts. I easily could have practiced law for another 15, 20 years, whatever. It’s a job you can grow old with, but I decided I wanted to make more of a difference in more people’s lives.

Adriana Linares:
And I do think that a lot of times lawyers underestimate how marketable their skills are outside the traditional practice of law, which is why I love talking to professionals like you who did that and speak so positively of it. A last question for you, and I don’t know if this will be easy or hard for you to answer, but if a lawyer came to you, and maybe they do, and said, “Oh, I’ve been practicing for 15, 20 years. I’m successful. I’ve made all the money I need to make, but I don’t know if I want to do this for the rest of my life,” what questions would you ask them to ask themselves when making that type of decision to do something alternative with their life or with their experience?

Phil Diamond:
I think it’s the questions, things like, “Are you happy?” That’s

Adriana Linares:
Number one. Seems obvious. It’s a good one.

Phil Diamond:
Right?
Yeah. Are you dealing with the people you want to deal with? Are you helping people do things that you want to see and help them do? I’d say, “Where are you financially? Are you in a good spot financially? Is this something where you could make a change? Is this something where you could do something different?” Some people have more of a desire, are more community focused, more of a communitarian, if you will, because they’re more focused on the community at large. Other people want to focus more narrowly. Those are both great. This is a conversation that people have before they might run for a judge or try to become a judge. Sure.

Adriana Linares:
Yeah.

Phil Diamond:
And it’s a change, but I think it’s a good thing. And even if people ultimately decide, “No, I’m happy where I’m at. I’m happy working at this firm, or I’m happy working in-house for this company,” great, but it never hurts to ask yourself these questions because you don’t want to look back when you’re older and say, “I had a good career doing this, but I kind of wish I had done this. I kind of wish

Adriana Linares:
I had

Phil Diamond:
Started a business. I kind of wish I had done something a little different and I could have afforded it or my family could have made it happen. We could have worked something out.” I think it’s good to do kind of a check-in every now and again. No, I agree with

Adriana Linares:
You. Maybe

Phil Diamond:
Not every year, but every couple of years, it’s probably a good thing.

Adriana Linares:
Well, Phil Diamond, comptroller of Orange County, Florida. Thank you so much for your time, your sage words. I know my listeners are going to love it, so thank you so much, Phil, for your time.

Phil Diamond:
Oh, thank you. I enjoyed it. I appreciate what you do. I think it’s great to get the word out to people. I look forward to seeing this.

Adriana Linares:
Thanks for listening every Everybody, we’ll see you next time on New Solo on the Legal Talk Network.

Announcer:
I was thinking this was the way to go and you put up your show.

 

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