Nov. 3, 2025

The Lawyer Who Sees the Whole Deal

The Lawyer Who Sees the Whole Deal

In this episode, we sit down with Thomas Hooks, General Counsel, Chief of Staff at Stately, and City Councilman in Lafayette, Louisiana to explore how legal, strategy, and leadership intersect in M&A and beyond.

Thomas isn’t your average in-house attorney. With a background that spans industrial services, local politics, and private equity dealmaking, he brings a systems-thinking lens to every deal, team, and tension point. He’s also a husband and father of six with a grounded identity rooted in faith and family.

Whether you’re an M&A lead, founder, operator, or advisor, this episode will challenge how you think about risk, integration, and the people side of transactions.

Key Topics Covered:

  • How to balance family, faith, and high-performance leadership
  • The four great temptations in ambitious environments: wealth, pleasure, power, and honor
  • Why general counsel must be the unpopular truth-teller in deals
  • M&A strategy: scale vs. capabilities, and how to think like an operator
  • Leveraging salespeople and product experts for acquisition insights
  • The difference between public-sector and private-sector deal dynamics
  • How to build organizational alignment across visionary and risk-averse leadership

Connect with the Guest:

Thomas Hooks

General Counsel & Chief of Staff, Stately

City Councilman, Lafayette, LA

LinkedIn: https://www.linkedin.com/in/thomasrhooks/

Connect with the Hosts & The Deal Podcast:

Joshua Wilson LinkedIn: https://www.linkedin.com/in/joshuabrucewilson/

YouTube Channel: https://www.youtube.com/@TheDealPodcast

Website: https://www.thedealpodcast.com

Joshua: Good day everybody. Welcome to The Deal Podcast Powered by FA Mergers. Uh, we're here with General Counsel, Mr. Thomas Hooks. Welcome to the Deal Podcast. Thank you. Happy to be here. Yeah. So we're gonna go over some really fun information about general counsel. What the heck does that mean? And, and we're, we're gonna explain some p uh, plate spinning as well, 'cause you have a, a few different roles, responsibilities in your world.

So, Thomas, why don't we start out with this man. Talk to us about a few of the plates that you're spinning. Right this moment. 

Thomas: Okay. Okay. So, uh, day job is, uh, husband and father. So I'm married. I've got six kids, 12 to 12 weeks. So, uh, those are, you know, seven plates spinning right there. Um, otherwise general counsel and chief of staff at Stately, uh, which is a company that's.

Primarily focused on the door and window space, uh, expanding that across the country, and then also serve local politics on the city council, uh, in Lafayette, Louisiana. And so, uh, those are a few of the plates in addition to, you know, the usual dad stuff, coaching, soccer, trying to get people to and from practices and games, and just otherwise keeping things sane.

Speaker: So simple math, six kids, 12 to 12 weeks. If we look at the average kid, how many diapers they go through by the age, you know, until they get to out of diapers. Man, you've, you've invested in some diapers. 

Thomas: Yeah. Our goal is, uh, once we started having kids until we were ready to stop not getting out of the car seat and diaper phase and, uh, so yeah, we've been continuously changing diapers for 12 years.

Wow. 

Speaker: So you're pretty good at it. 

Thomas: Pretty good at it. Yeah. 

Speaker: My wife is better. Describe your diaper bag. Do you have one of the cool ones like the, you know, go bag that has army camo? 

Thomas: It evolves as we've gotten older. You know, it's gotten more sophisticated, more sleek, but, uh, pretty much whatever we can put things in.

Speaker: Yeah. Cool. So, all right. Husband and father, when I asked you, you know, kind of roles, responsibilities, you know, like you, you, you first went to that as part of your, your, your job, your responsibilities. You didn't first go to city council of, you know, Lafayette, or you didn't go to general council chiefs. I mean, you, you talked about your role as husband and father first.

How do you, how do you view that when it comes to plate spinning and roles, responsibilities to them? 

Thomas: I think, uh, it's a constant conversation and something that I think about and talk about with friends often. I mean, um, in the professional world, you know, you can think about the four great temptations.

It's like wealth, pleasure, power, honor, and definitely at different points in my career, um, all four of those things have spun up as temptations. Uh, something that clicked a few years ago, uh, after going on the retreat. Was just remembering that at the end of the day, it's humanity and it's like dealing with the person in front of you.

And that's something that my wife, uh, calls me to quite a bit in terms of don't get caught up in those things. Remember that your identity is dealing with the people who are in your life. Yeah. And on the human level, not as instruments to get what you want to achieve. Yeah. Um, and so in terms of identity, I think it's important to just stay rooted in.

At the core, what's your identity? And for me, two of my big roles are husband and father. 

Speaker: Wow. Dude, that's so good. I, I love this. The, the four great temptations, right? We got wealth, pleasure, power, honor. Mm-hmm. Right. There's some, uh, really great clips on how to decide which yours might be. Why is it important to know what your temptation might be?

Thomas: I think, uh. If you're in a fast-paced environment surrounded by ambitious people, and you too are an ambitious person, you gotta know why are you chasing what you're chasing? So I can get very hung up on shiny objects and you know that shiny objects might not be money, it might be status. Mm-hmm. Um, so whenever in certain roles.

Bigger organizations, that status comes in terms of job titles. It comes in terms of team size. It might come in terms of compensation or bonus, and you get very hung up on, well, I want the next thing, and you get into sort of autopilot and you just do the things that are required to get to that next thing, that shiny object, but.

If you're not rooted in, again, like that identity and what are you actually trying to accomplish here in the present, you're just sort of on autopilot. You're not mm-hmm. Intentional about why you're doing the things that you're doing. So for me, like understanding which of those temptations is currently, you know, flaring up inside of me and how's that impacting the decisions I'm making is very important.

Let's just use 

Speaker: me for an example. Yeah. Okay. So out of wealth, pleasure, power, honor. I want 'em all for sure. But I think the one that, uh, probably is the most tempting to me. I'd give up money, I'd give up pleasure, I'd give up power. But the idea of honor of being recognized or being approved of, yeah, the approval of man like that would be, especially as deal maker, right?

Like I, I love doing deals and put it together. It's part of my mission. It's who, it's part of who I am and who God created me to be. Weird title, king Maker. Right. But like this, this idea of honor. Yeah. How could that get, uh, how could that pull me maybe in a wrong direction? 

Thomas: Well, I think about two paths, um, that are in my own life.

One is more the professional deal making side. You know, everybody wants to get the deal done and. Deal making. There is honor in it. There is like some prestige that comes with being in mergers and acquisitions. I've dabbled in other parts of the law. This is the one I've gravitated toward because it is inherently interesting and it's fun to talk about when people want to know what you do.

When you talk about deal making, it's just interesting, right? Mm-hmm. But you can get so captivated or attached to getting the deal done, like are you being. Kind of an honest broker of information to the parties in terms of giving them the risks and the potential downsides and questioning sort of the deal thesis and say, have we really thought about why we're doing what we're doing here?

And does it make sense? And those are hard conversations. Mm-hmm. And if you have a strong desire to be liked, which I've got, I feel like a lot of people do. 

Speaker: I like you. 

Thomas: Uh, yeah. Thank you. You're welcome. Appreciate that. 

Speaker: Yeah. Then. 

Thomas: Putting yourself in that seat to give people unpopular opinions or ask difficult questions, uh, can be challenging because you wanna be liked, you wanna get the deal done.

You wanna be known as somebody who gets deals done and not an obstacle, but it is important and it's in-house counsel, you know, that is the job. It's just. Being able to sit down and talk about the unpopular things as well as the popular ones on the city council side. Um, it's the same thing. It's local politics, right?

One of the reasons I like local politics is because you do bump into the people that you're working with in the grocery store, uh, at the ball field, um, and not everything has a yes answer or a good answer. So part of my growth in that role as city councilman is just being better able to give people quick answers, especially if it's not a good answer.

Um, because then people can adjust. They can plan their life, they can make alternative plans, but if you keep stringing people along and giving them this false hope, knowing that you won't be able to deliver or it's unlikely that you'll be able to deliver, you're not doing anybody any favors. You're just sort of deferring that pain or that eventual.

You know, negative emotion that's gonna come. And so, you know, overcoming that desire to be liked and just being able to give people the best information you got when you got it. I think 

Speaker: I would struggle in, in the world of politics, city council or, or fill in the blank, because of my, my desire for honor and man's approval.

Right. That's, that's a battle that I, I struggle with. Yeah. Like part of the job to get that. Did they put you through like just. Practicing being yelled at, like, like people just yelling at you or sending you mean emails? Is that part of the training program? So, uh, 

Thomas: I wish there was a formal training program.

Um, I was lucky in that when I went to law school, um, one of my good friends who I met early on was a former reporter, uh, that covered local politics. Oh, cool. So as we were going through law school together, taking local government, taking different courses. I was just getting also a master's course in local politics.

So whenever we graduated, uh, I practiced with a firm for a couple years, uh, and then we're looking to move back home. When I got back home, he was like, Hey, here's some things that you should consider just to be more engaged. One was being on the planning and zoning commission, so if you're not familiar, planning and zoning is where everything real estate development.

Needs approval. So whether it's a new development, um, whether it's rezoning a property so that it can be used for a new purpose, that all goes before a volunteer commission. Um, as you can imagine, people take their homes, take their properties very seriously. There's a lot of emotion tied to that. So when things are changing, um, and maybe something is coming in that.

20 years ago when you bought that property, you never anticipated there would be something commercial there. Or you thought that empty field would remain an empty field forever. Well, that's not the way it is. Things evolve and things change. So the planning and zoning commission, to your point, was a great, uh.

Testing ground. Yeah. 'cause you go into a meeting and if you see a lot of people, you're like, okay, we're in for a long night. Because they are concerned. Some of them are angry, some of them are very worried. Um, often tell people those meetings are difficult because you have the applicant who wants the deal that they're trying to get done.

You've got neighbors who might have concerns, some are supportive, some are not. Uh, what you don't have in the room or the people who are gonna benefit from the change. So people who drive by that area that will live here 20 years from now, that will shop in this place 20 years from now. And so you go into that room knowing that.

You are likely to get yelled at, you are likely to have to make an unpopular decision, but that's what you're called to do. And so that was a good testing ground and I tell people who are interested in local politics, find your local planning and zoning commission. Go volunteer and get start there. 

Speaker: Yeah.

This is, this is, uh, politics training ground on, on this episode. Man, this is fun. Um, we, we moved to general counsel, chief of staff. What the heck do those roles do? 

Thomas: Yeah, so, uh, a couple different things. General counsel. That is my formal training. So I came through law firm for a couple years, uh, on the transactional track.

So I tell people if I'm ever in a courtroom, it's because I'm in trouble. That is not my place. Uh, this definitely pushing paper and pushing deals. Um, from there I went in-house, um, but while in-house with an industrial services company, um. I love to learn new things. I'm one of those people that if there's an opportunity and raise your hand, make eye contact, and it was that type of company.

If you did those things, they'd invite you to get involved. Um, we had an m and a acquisition, uh, coming up. Um. The project manager who was on the team had just left the company. So they said, Hey, Thomas, would you like to project manage this? 'cause they know I'm just, I'm, I wanted to learn new things. And so I did that.

Um, along that path was working with our VP of m and a who was a former consultant. Um, and we really hit it off. So after working on that deal. And seeing her work did a hybrid role for a little while in terms of, uh, legal as well, but more strategy focused. Um, and that sort of turned my career path into focused on, you know, the business unit strategy, um, transformation programs and just how to keep the trains running on time.

So that role that I have now, general counsel, chief of staff, is. Of that blend because I'm in-house counsel for the company. General means it's whatever legal issues pop up. I am not a specialist in each area. It's known when to call specialists in, um, and making sure that we're navigating the legal risks.

Well, the chief of staff role is more about the strategy and the transformation. So does each of our. Units. Each of our companies have a solid go to market strategy. Do they know where they need to play, how they need to win? Um, if they have those things and we have initiatives that we need to launch or that we need to follow through on, you know, do we have that documented and are we hitting it on the regular cadence to make sure that we're getting those things done?

And then there's a change management component as well, which is mm-hmm you can have the best plan. You can sit in the conference room with your peers and knock it out. But if you're not bringing the rest of the organization along. It's not gonna get done. You're not gonna get the value. So it's trying to balance those three things and, uh, make sure that we're executing on each of them.

Speaker: Yeah. Fantastic. Let's just say you and I are working together on, uh, we're working at a industrial firm and, uh, and we're, we're looking at a m and a strategy, and they're like Thomas, Josh. Why should we do, you know, growth through m and a, like what, what benefit would it have for us? And you say, oh good, we've been doing this for the last 15 years.

Here's why you should do m and a or think about it. Yeah. Right. What, what are some of the things that come to your mind? 

Thomas: I mean, I keep things simple. It's like scale or capabilities. Like are you looking to, you know, just continue. To expand what you're currently doing, but bringing the two more customers into more markets, then you might be able to find customers or companies that are very similar to you, either in terms of size, but definitely in terms of what they bring to the market.

And those might be good acquisition opportunities because instead of starting fresh Greenfield, going out there and leasing an office and just trying to build it from this ground up, you know, you can acquire a market in that way. And so you can scale, but the other one's capabilities. So, um, I think. The spaces I've worked, especially in industrial services, um, everybody wants to be the specialist.

You want to be more consultative. You want to be bringing something to a customer or to a market that is unique, um, and more valuable than the commodity they can get everywhere else. So in that sense, it's what do the customers require or, or would they desire that? We're currently not doing, but we could do, or somebody's given that niche and it's not a capability that we can go out and acquire.

So at the end of the day, I think it's those two things. Like are we, are we trying to scale, we just wanna bring the same thing to more people, or is there something new that we're trying to bolt on, um, that will make us a more valuable company and make our solution more valuable to our customers, then great, let's go get that capability.

Mm-hmm. Um, so at the end of the day, like those are the two ways that I'm generally thinking about the deal. 

Speaker: Yeah, I like it. All right, we're gonna go another level deeper on, in terms of m and a strategy, right? Same, same group that we're working with. And they go, okay, great. We're looking for, you know, maybe some scale or some capabilities.

Where do we even begin in, in this process? And, you know, like, how should we be thinking about this that we might not be, you know, here's our books, here's the, you know, walk us through this, Thomas, how should we be thinking about. The scale or capabilities, how should we be thinking about m and a? I love to talk to 

Thomas: sales teams and then the product experts.

Why? So the sales teams are out there talking to customers every day. They get told no more times than they get told. Yes. Um, the really good ones. Have those relationships where they can ask why, and they get that answer. And so they've got a good feel for what is it that customers are actually looking for, and why are they not saying yes.

And then if they're not saying yes to us, they're saying yes to somebody else. And so why, what is that company doing? So the sales teams are a great source of information, um, and you gotta be discerning with any feedback. But I found that to be. Very valuable 'cause they're out there talking to customers every day.

And then the product experts. So if you've got, you know, engineering teams, product design teams, folks who are constantly looking at technology, looking at what manufacturers are bringing to the market, um, they tend to have a good pulse on what's interesting that's coming up. Mm-hmm. And. Is this something that is niche and gonna be very difficult for everybody to do?

Or is it something that's, you know, mass market and anybody can acquire it? They've got a good sense for that, and so you'll get some interesting ideas from them as well. And so I really like both of those teams in terms of ideas for potential acquisitions. 

Speaker: Okay. Let's go another level deeper. You, you and I are, are looking and, and meeting with the sales team, round table discussion.

Uh, is that something you wanna bring the executives into or let, let's just have a conversation with the sales team first and we're gonna, we're, what's the, what's the proper setup? Do you there, do you think? 

Thomas: I, uh, I love one-on-one conversations. I love small group conversations, so when we're doing like a strategy deep dive, we'll generally identify.

A list of folks that we want to talk to. So maybe it's to inform, uh, just organic growth. Maybe it's to inform m and a strategy. So who is that list of salespeople that I want to talk to, operations people that I want to talk to, and pretty much the same list of questions. And then I'll just spend a week or two just dialing up people and talking to 'em for an hour, hour and a half.

Just learning everything that they think about the business, and then taking that and synthesizing it and bringing it to a senior leadership team or an executive team and say, Hey, here's what people are saying that they might not be saying to you because people are less comfortable speaking to the entire executive team off the cuff on a very transparent manner.

Whereas if you're having those one-on-one conversations Yeah, and actually able to dig in, you'll get gyms that you wouldn't otherwise get in a big group conversation. 

Speaker: Let's just say we have a hundred salespeople. Yeah. And we're going through this process. It could take us years. Are you looking at top performers, people with the most activity, people with the most amount of phone calls, emails, rejections, what?

You know, like how, how would we narrow that list down to make sure that we're getting the right feedback? Because the, the, the, the first in, you know, might not be the best. Yeah. The person who just got hired might not have any feedback. How do we narrow that list down? 

Thomas: Well, uh, I think you want a good mix.

I will say that in any organization I've been in, there's usually a list of salespeople that drive everybody insane. Mm-hmm. But they're also the top performers and they drive everybody insane because they are first and foremost like a customer advocate. Anything they need to do to sell the job, they're dialing up everybody in the company to get it done.

They're doing it on Friday afternoons, they're doing it on Saturday morning, and so. They tend to get on that list for a good reason. They're customer advocates, but those people I definitely want to talk to. Yeah, because they just live and breathe getting this next piece of equipment on rent, getting this next product sold.

And that is their mission in life. But then you might have people who come from a different industry, uh, they come from a different company. Um, there. Not yet as successful as those other reps. 'cause they don't have the relationships. So they're out there trying to sell new accounts. They're not forming so much as they're hunting.

And you wanna speak with those folks as well because they'll have a different perspective. Different perspective. Um, obviously they might not have the track record of success, but that alone might be a good reason to talk to them. It's like, why aren't they succeeding and is there something there that we can do to help them?

Speaker: Yeah. So the, the peta, the pain in the butt salesperson. Right? You like that? I like that. Cool. The, the, the guy or gal who doing the most volume, most activity, crushing it in terms of, you know, balance sheet improvements, right? Like this person is, but they're also that person who's the biggest customer advocate saying, we need this.

Why aren't we doing this? Getting on. That's the person we want to talk. I just, I got chills, man. I don't know why, but like, man, like that's the person we want to talk to because they can be the one that sparks the ideas for m and a activity. Yeah. That can scale or increase the capabilities of this company.

Thomas: Yeah. Like the people who are agitating for change. Like there's something to be said for that. Yeah. Like they. They are looking to not settle into the status quo. And you need those people, you need that constant tension because you can get very comfortable in routine. Um, but people who are asking you to work faster or work differently, 

Speaker: yeah, 

Thomas: it's good.

Again, you can't always say yes, but it's good to be thinking about that. It's good to be challenged in that 

Speaker: way. Well, I need to be challenged here, especially with the guy who has a high need for approval and honor. Right? So that agitation, what, what that would, if I don't lean into that agitation, let's just say I'm the CEO of the company that we're, we're discussing.

You're like, Josh, man, you gotta, you gotta put your big pants on because big boy pants on. Because that agitation for change and that tension. Is actually good and here's why. Yeah. But then I go, okay, cool. I need to bring in the team, like fa mergers to kind of walk us through our m and a strategy. We, we want to talk with Thomas, we want to, we wanna do this, but okay.

So we get that, that agitator Right. Which is phenomenal. Right. And we gotta lean into that a little bit and we go, okay, cool. Tell us about, you know, what, what the customers are asking for. Where are we missing opportunity? And we want to, instead of avoid them mm-hmm. Definitely don't wanna fire them, right?

We wanna lean in and go, cool. What question should we ask them? Like then 

Thomas: what I mean in terms of questions that we ask? I mean, the favorite is always why are we winning and why are we losing? Like it's just, it's that simple. Like you can go more granular than that and you'll pick up on things that you can follow up on.

But at the end of the day. I want to know why are we winning with the customers who say yes, and why are we losing with the customers who say no? Like, there's definitely more that you can dig into around, well, what's about the product? What's about the value proposition? What is it about our service? Um, but at the end of the day, again, like customers.

Generally want three to four things, like they want the right product or service. So the thing that you said you could do, they want it. They want it on time. If there's gonna be an issue with either of those things, the product's defective or the product's late, they wanna have a quick path to resolution.

And then the fun one, which is not super fun, it's just they want a clean invoice at the end of it all. So. Regardless of the business, you're trying to deliver those four things, but it's understanding why do some customers say yes and they're satisfied with our performance across those four versus some who we've been trying to crack the code and they're just saying no and could be for any number of reasons, but ask enough people the same question.

You're gonna start to get some common answers, and those are the ones that you really wanna circle and double click on. 

Speaker: Okay. So general counsel, when, when would a company need a general counsel? 

Thomas: So, um, probably at the point at which, and this is gonna be a boring answer, the amount that you would spend on outside counsel is gonna pretty much cover that salary with overhead for an in-house counsel.

And that's not a perfect answer, but there are some things that are relatively simple. And you can rely on the outside council's help. They'll set you up with everything that you need, and then you just operate the business. Um, once you get to a certain scale. If you had to call outside counsel and pay by the hour each time, it would just not make sense anymore.

And that's whenever you could start to look at bringing somebody in, um, on either a fixed rate basis that works with a law firm. There are lots of legal services providers these days that offer sort of part-time in-house counsel. Um, or if you end up with a firm like the one I'm in right now, which is both heavy on base business and organic growth, but also.

Acquisition activity. Um, that's whenever it makes a lot of sense to have somebody there. I would say in general, even if you're not bringing somebody on full-time as general counsel, having an attorney that you trust and rely on on the routine basis, somebody that can come in on the Friday morning and just sit with you for a couple hours, the good ones will do it off the clock.

Um, to just understand your business, understand what you're trying to do. Where the risks are, like those are the people who are gonna be invaluable, and whether or not you bring them on full time or not, doesn't matter. It's just about having that person that you can rely on, uh, to help you navigate some of these risks that for most people.

It doesn't come natural. Like nobody is born thinking, I would love to read 50 page contracts whenever I'm older. Um, but some people find themselves in that situation and can find that they enjoy doing it. So finding those people, uh, early on is super valuable. 

Speaker: All right. There's, uh, when I was studying for investment banking and we were looking at a, uh, we were looking at a deal and I had to read through SEC paperwork.

I was ready to jump out of my, my window. Man, it's tough. You said you can learn to enjoy that process. You could actually like be good. Gimme some feedback here because SEC paperwork is the most dry thing I've ever read in my life. And I think it's, uh, I 

Thomas: was saying this earlier, I am a nerd, so I like to know the finer details of things.

Speaker: Yeah. 

Thomas: Um, and so even from a drafting perspective. You know, there are just some great books out there that I latched onto early and it could be typography for lawyers. There's a person, Matthew Butrick, who wrote a book Typography for Lawyers. That's just all about how to make your documents look good really.

So that was super fascinating for me. Uh, there's also one Ken Adams on drafting, which is just like, there are 13 different ways to draft this wrong. Here are the right ways to draft it so that it's understandable. So I think it's. Learning the craft. 'cause everything could be a craft, right? It can be, uh, something that you can continuously get better at.

You don't just go onto autopilot because you've read one document or drafted one thing, one way you can always get better. So I think if you're taking that mindset of like this craft mindset to either drafting or reviewing documents and draftings can inform how you review them. Mm-hmm. Um, it can make those things interesting.

The SEC documents, it might be more around how much do you. Really dig, understanding how companies disclose what they do mm-hmm. As they're required to do. And can you really tease back what's actually going on here? Because a lot of that is boilerplate that they copy and paste year over year. Mm-hmm. And so when you've looked at enough of them and you see the small things that are changing, it's like, oh, well that's where the money is, so let's go find out why.

Um, and it's just kinda being curious and letting 

Speaker: that guide you. Right. You warned us. You said, Hey, Josh, uh, coming in here, I'm a bit nerdy, right? You like love books and you just. Proved it to us, right? Like I studied the typography of contracts and I, I love that and I find that so fascinating and valuable because that is a weakness of mine, right?

Like I'm, I'm, I'm uncovering myself. I've got a lot of weaknesses, guys, especially people listening in, like Josh has a lot of weaknesses. I love your strengths of, of paying attention to the finer details and actually finding joy in, in that. Talk to us about maybe some other books that you would think that.

I would be like, bro, that's pretty nerdy. 

Thomas: Uh, you know, other nerdy books. I don't know. I'm a big fan of Shrunken White and the elements of Style, you know, that could be out of date. But, uh, great book on writing, um, that I still think about quite a bit if you're an Oxford comma person, you know, great book.

Um, but no, I mean, those are, those are books that I like. There are others like. Professionally, you know, we're talking about deal work. I like to think about integration, which is often, you know, the neglected part of a deal. Thinking about how are we gonna make these companies more valuable together than they were separately.

So diving into different books on integration, um, and not all books. YouTube, obviously tons of content there that is available. Um, but different things to help kind of scratch that itch. Um, and then in terms of personal development growth, I mean my career has not been five year plan. After five year plan, it's been sort of lily pad by Lily pad.

Like what is the opportunity that's presenting itself right now and is that the right one? And for me, legal counsel, uh, going through law school, you get very. Good at identifying risks and being risk averse. Um, I have to be very intentional about also identifying opportunities and being more reward oriented.

And so there are some great things out there. And Nasem Taleb has a book called Antifragile. 

Speaker: Yeah. 

Thomas: Great book. Great book. Great book. That is one that I picked up probably 18 years ago, and that still every few months I think about and try and draw from. Mm-hmm. Um. Things like that that for me personally, I know my thing is I need to be more open to opportunities and accept the risk.

Um, those are the types of things that I'm trying to expose myself to right now so that I'm open to that next new thing and not closing it off because it could not work out for 

Speaker: sure. There's a balance, risk, reward. Uh, I have, mine is geared towards reward, right? Yeah. I I will, I'm heavily reward, driven and focused.

Yeah. Uh, which I need the balance of like my wife who is more risk associated, right? Like she, she's like, kids don't. Play on that slide, right? And I'm like, no, go down it head first. You know, like, have, have fun. I think that there's a, and we'll, we'll, we'll, we'll dive into the, the risk reward kind of drivers of each human and why it might be important to have a few different people at the table.

Yeah. But before we do. When the, I think it was the Vampire Weekend when they came out with the song Oxford Comma. Was that like one of your jams and you were so 

Thomas: excited about that? See, now I need to go make this part of one of my jams 'cause No, I'm not familiar with it. And now I've got, there's a 

Speaker: song 

Thomas: about Oxford commas.

Okay. Yeah, you're gonna have to, which is great. You're gonna have to listen to it. I'm super excited. 

Speaker: Yeah, 

Thomas: we can add that to the, to the pod, uh, playlist 

Speaker: to be awesome. Yeah, I think you will enjoy greatly. Alright, so the song, I think it's called Oxford Comma. Someone could correct me if I'm wrong. All right.

Risk reward scale. And why is it important to have a few as a CEO? Let's just say the, the founding CEO O is probably more driven towards a, a reward. Let's go, let's roll, right? Mm-hmm. And then you get to a point, I think, I think those are the, the great ways to get things started. But to, to grow smart and make sure you, you don't take 10 steps backwards.

It's, it's good to have people who are more risk oriented, right? Yeah. So talk to us about that and how to deal with the. Internal politics of managing that. 'cause you're in city council, right? That city, yeah. But there's also those kind of politics within an organization. 

Thomas: Yeah, absolutely. So, um, I think part of it.

And this could be cliche, just depends on kind of where you are as an organization. Are you a startup? Are you getting to that a hundred, 150 employees where you don't know everybody anymore? Um, where everything can't work on tribal knowledge. Like you've actually have to have processes and systems. So I think part of it's knowing where you are as an organization, um, and that CEO.

Is a risk taker, by definition. I mean, otherwise why would you ever start your own thing? Like it's never a guarantee. 

Speaker: Yeah. 

Thomas: Um, so that's good. Um, but once we get to a certain size, it's like, okay, well they're boring things. Like you do need an expense policy. Like you've got to at some point know where you're spending money.

We could expense the boat. Yeah. It's just things like this. So, uh. Yeah, I think it's making sure that you're surrounding yourself with that team that has both that person who is the visionary and risk taker, but also people who know how to build systems, who know how to make sure that that risk taker, that visionary.

Isn't also driving everybody in the organization crazy. Yeah. Because, uh, they could be shiny object oriented and every week it's a new thing. Well, the rest of the company who's just trying to be the best accounting team, the best legal team, the best finance team, the best IT team, the. They can't do a new thing every week.

Like they gotta get good at the core of what they do and make sure that that is stable so that we can continue to scale this organization. So you've gotta have a good blend of people who can both identify those opportunities and agitate for change. 

Speaker: Yep. 

Thomas: Um, and good CEOs, you know, every so often they're putting those heart, those heart paddles on the organization and saying clear.

Speaker: Mm-hmm. 

Thomas: And then driving some new change. Um, but the people who they surround themselves with who take. All of those desires, all of those shiny objects and say, Hey, here are the two or three things I think you're saying we really want to get done this quarter, this year. We're gonna go out and do those things and we'll keep you up to speed if we're not moving fast enough, challenge us.

But let's go get those things done and then come back and talk about what's next. And as with any plan, it's a living document. It's a living thing. Um, it will change, but you gotta have some core around which you're trying to work every day. 

Speaker: You're fascinating. I really enjoy our conversation. What is your superpower and in the world of deal making, where's, where do you find most joy?

Thomas: My superpower. Good question. I'm obviously buying time to answer it. I don't know. I like to sit back. I like to think about why are we doing the things that we're doing, so I. Enjoy pretty much every aspect of the business. So I want to know how every piece fits together. So I'd say probably that systems mentality is the thing that I like to try to bring to the table.

I'm not gonna say I'm always a hundred percent successful at it, but like why does the sales team not get along with the operations team? Um, why was that integration not successful? Like, what is it that's not clicking? And then. Kind of disassemble everything and see how we can put it back together. So that could be, like we said, go to market strategy.

Is it not clear? Is it not well understood by both teams? Um, if it's acquisitions, it's like, are we not clear on what we're trying to accomplish in our acquisition strategy? And with this acquisition in particular? So. Trying to see the big picture and making sure that we're having those conversations. Um, even if they can sometimes feel theoretical, like they're very important.

Um, so I'd say that's, that's the superpower I try to bring to the table. Your other question was joy. Joy. I really enjoy that too. Like that is the part that I really like. Isn't it cool how the superpowers usually align up with the, the joy? Yeah, for sure. Like, I love a blank, uh, whiteboard. Um, I love a blank word document.

I can find myself super happy in an Excel spreadsheet that is a model of something that we are trying to accomplish. I like sinking into that sort of work. Um, and I found personally that. You know, I still want to be hands on with that type of work too. I, like I said, enjoy doing the work as much as working with the teams to get the work done.

Um, so yeah, that's where I find the most joy, which is why we're trying to, whenever it feels like we've got harmony between all of those moving pieces, like we can bring everybody along and help everybody to see. With clarity what we're 

Speaker: trying to accomplish. You love a blank page? Tablo Ross tell you love starting like and going, what could we create?

What could we build? What could we do? Yeah. Okay. Very cool. If you were an I, if you were, that was a weird way to say it. If we were gonna write a book together, what book would you want write? It could be business, personal, it could be. 

Thomas: I would love to do what we talked about earlier, like I'm a risk oriented person, so I like to think about, or I gravitate toward.

I don't like to think about, you know, here are the reasons not to do something. It sounds like you're the opposite. You're like, here are all of the reasons that this is a good idea. 

Speaker: Yeah. 

Thomas: How do we navigate that? How do we get it right? Like that is the topic that I've been most consumed with probably over the past three to five years in terms of taking those risks.

Yeah. Um, and I'm not gonna say it comes naturally, but, and exploring that space, you know, I'm finding that I'm more open to it. So that would be the book I would love to write, which is how do we identify what are those right opportunities and. While mitigating risks, 

Speaker: still go after him. Okay. So we're on chapter two.

We did the introduction, your story, my story was fun, but now we're gonna dig into the first question about that risk reward mentality. 

Thomas: Yeah. 

Speaker: What, what, what's the, what's the chapter? What, you know, dig into that a little bit and what's the, what's the process? So you get to almost like, you get to like dig into a risk taker 

Thomas: Yeah.

Speaker: And understand how their mind works. Yeah. The deal makers out there. Yep. Right. I, uh. 

Thomas: I think it's knowing what to say no to, regardless of the risks. So even before you get into that analysis. So this is a conversation to have with my wife. It's a conversation we have at work. It's a conversation to have with myself personally.

There are lots of things that we could do in life. Personally, professionally as a company, um, Warren Buffet had sort of the punch card mentality. He was like, just imagine that your career has 20 punches on it. Um, or you can acquire 20 companies. So there are a lot of companies that you ought to pass on before you even consider going forward and executing.

So I think for me, or like chapter two is how do you identify what you should say yes to? Because those things are when you're gonna dig into where are the risks and what are the opportunities and how do we navigate that? Mm-hmm. But there's a whole slew of things that, whether it's because personally you don't find joy in it, it's not gonna give you, uh, energy or, um.

You're just not competent. Like you don't have the skill or the expertise to do that at a high level. Well, those are things that maybe I should say no to or acknowledge that they'll be a hobby, but not something that I do professionally. Um, whereas those other things where I find great joy or I have high confidence, great.

If those two things align, I should be pushing more into that. And when opportunities come across, if they're not joyful and I'm not good at them. Well, I should probably be saying no to them. Even if we talked about desire to be liked. There are a number of people who are like, oh, we would love if you did X, Y, and Z.

It's like, well, that's not good for me or my family, or anybody overall. Um, I think chapter two would be what do we say yes to? What do 

Speaker: we 

Thomas: say yes to? 

Speaker: If we had a worksheet at the back of chapter two? Yeah, I think it would be in column A. List out the things you know, you should say no to right off the bat.

It doesn't bring you joy. It doesn't make you money. It doesn't move the needle forward. It actually, like you hate doing it. Yeah. Or you know, you're weak at it. Right. So we, it's almost easier if, if we had two people to, you know, fill out two people were at our book. Yeah. I think it would be so much easier to fill out the list of the nose first.

Because sometimes it's hard to, it's like, what do I say yes to? Well, does it make me money? Yeah, sure. But if we have, does it make me money? Does it, do I find joy in it? Right. Can we actually do it? Can we deliver? Yeah. Well, I think that no list also, 

Thomas: uh. Probably helps you avoid that shiny object syndrome too.

Sure. Because there are a lot of things that are tempting to say yes to, because again, they're gonna scratch that itch. Wealth, pleasure, power, honor. 

Speaker: Yeah. 

Thomas: Um, for me and you, it sounds like honor might be the thing. 

Speaker: Yeah. 

Thomas: So like, yeah. Will this make more people like me or make me more likable? Maybe that's why you would say yes to something, but.

Again, there are a lot of good reasons to say no to those types of things as well. 

Speaker: Yeah. To that own itself be true. It's, it's very, very good idea to, to know, uh, where your tendencies to make poor decisions are. And, you know, for me it would be like, will this get me more followers? Yeah. But will it cost me a lot of money?

Yeah. Yeah. So maybe I shouldn't do it. Right. Yeah. So, but knowing our, our weaknesses as, as Dealmaker makes us better. It doesn't make us. It doesn't make us worse. It makes us actually better knowing that and being honest about it. Being honest with ourself and I think is helpful. Man. Thomas, you're, you're, there's some depth to you, my friend.

I'm so glad we're having this conversation. We see each other in the halls. We're like, Hey, man, high five, it's good to see you. How's the family and stuff? But like, there's, there's really cool depth. Um. Maybe on future episodes we'll go into chapter three. Maybe one day we, heck we'll even write this book together.

Just started, man. Yeah. Got blank piece of 

Thomas: paper in front of us right now. 

Speaker: That's right. Uh, one thing that I want you to think about after we hit stop recording is a question that you have for future guests. Okay. Okay. But I have a question from it was, um. A guy who came in, he was in corporate banking, and he moved to the world of, uh, the CFO for, for a bank.

And then, uh, it was Tim and, uh, he was on the last episode. He has a question for you, so I'm gonna read the question and then you get to ask the next guest. So when you were at, yeah. Tim, hey, I got it right. When you were asked to do the, the podcast, why did you say yes? 

Thomas: Why did I say yes? Because this is a thing that.

I think scratches that part around opportunity and putting yourself out there. 

Speaker: Yeah, 

Thomas: it would've been very easy to say no and just go back to what's in my inbox and getting the work done. Um, but again, my sort of professional goal, personal goal has been saying yes to more things that are interesting that might expose me to new ideas, new people, and new opportunities.

Um. 'cause doing the same old thing every day is easy. It's easy to get on autopilot. Mm-hmm. Um, for me personally, I know that where I am is it's more important to say yes to different opportunities. And so that's what this was and I've enjoyed it. 

Speaker: Yeah, me too. So, uh, before you write the question for the next guest.

I want you to think of, um, a question that I probably should have asked you, like, Josh, you're such a rookie. You probably should have asked me this in the, in the podcast. What questions should I have 

Thomas: asked you? A question that, uh, has popped up before in talking with people is how does kind of local politics compare to, you know, what you do at work or how things work in the private sector?

Um, and it's similar, but there are definitely distinct. Differences. Like at the end of the day, as a council member, you're responsible for the budget. So it's primarily a fiscal role. Mm-hmm. Um, and so as with any budget, like you're trying to make the best decision for what projects or what deals get done, the different piece in the public sector as opposed to private sector is for better or for worse, in the private sector when you're negotiating a deal.

Everything is sort of mediated by the dollar. Like there are things that there are risk that people accept or won't accept. There's a price that they'll accept or they won't accept. There's a timeline that they'll accept or won't accept, but at the end of the day, if you get the dollars right, people tend to get on board.

Ego doesn't necessarily come into play. How people are going to think about them when they're negotiating the next deal doesn't necessarily come into play. Um, whereas on the public sector side, you're talking to people every day about things that they want. Um, it's not, you know, trying to get the best deal personally.

You're trying to think about what's best for the city or the state, or whatever body it is you're representing long term, but. Not everything's mediated by the dollar. Like there are other considerations mm-hmm. That come into play. Everybody's got their own agenda, their own ego, and that's not a bad thing, it's just you gotta realize it and understand it.

And people are worried about how will this impact my reelection? How will this impact my next role that I want? And so it's not as clean on the private sector side, is understanding those variables that are in every deal. 

Speaker: Mm-hmm. 

Thomas: Here you can have a three hour meeting and be very unclear about what it is that you accomplished, but walk out.

And people who are more experienced that have been doing this for decades are like, oh no, that was a great meeting because we brought up X, Y, and Z. And it's like at work, that would've taken us 15 minutes. Mm-hmm. Here it took three hours. And that's not a bad thing. I'm not saying it's bad, it's different.

It's just different because there are a lot more factors at play and. Those different considerations come into account. And so it's just kind of learning what those are. Yeah. How does that system work? And then trying to adapt to it because it is a very different pace, um, and a very different way of working than on the private sector side.

Speaker: Yeah. Super cool. Now, I probably should have looked at your shoes before asking this next question as I see a Garmin watch. Mm-hmm. So are you a runner or a biker? 

Thomas: I, uh. I like to say I'm a walker who married into a running family. Um, so started running once I started dating my wife. Um, but now I'm more of a hiker.

So I love the weighted vest walk. I love, uh, kind of the, the GORUCK act like that's the thing I'm looking at right now. So as I'm getting older, I'm finding, uh, longer weighted walks is, you know, where I'm finding 

Speaker: more of my time. Yeah. But yeah, my wife and I do that. We, we put on a weighted vest and we walk around and it looks like we're, we look like crazy.

People walk around in downtown. 

Thomas: Yeah. But it's great. Like, it's so good. I love it. And like, you know, I find that I want to do that more often than I want to go on a long run. Yeah. Also, as I get older, my ankles and knees feel better about it as 

Speaker: well. For sure. For sure. So next time you're on your ruck, uh, you could listen to Oxford comma and, uh, we rock out to that.

And think about chapter three. Yeah, think about chapter three, right? Uh, for fellow deal makers in the audience, as always, reach out to our guests. Their contact information will be in the show notes. Um, super fun conversation here. If you have. Questions, uh, about mergers, acquisition strategies, reach out to us.

We'll, we'll plug in with, with one of our guests and, and maybe if you've got experience in that world as a corporate buyer or your private equity group, or maybe you're, that, that salesperson, that, that agitated agitator. Sales person who's just crushing it out there and you wanna talk about, you know, what you think would be good for mergers, acquisitions, or what strategies you might come to mind, man, we would love to talk with you on this podcast show.

Uh, it's the deal podcast.com. You could fill out a quick form, get you on the show, but yeah, we're looking specifically for in a decent sized organization who has that top sales person. Let, let, let's find out what they, that they have to say. But um, we've really enjoyed this conversation. Thomas. Thanks for coming on and everybody, we'll talk to you all on the next episode.

Cheers, guys.