How Can Companies Stay Exit-Ready and Build Long-Term Value with Carter Gaither

Welcome to the B2B Growth Blueprint podcast, where we talk with entrepreneurs, founders, and leaders at B2B services, tech, and SaaS companies to learn the systems and processes they've used to create success for their business. We'll also learn from marketing and sales experts to provide insights to help you grow your business. I'm your host, Mark Osborne, and the podcast is brought to you by Modern Revenue Strategies and their 10x ROI B2B Growth Guarantee. Schedule a free diagnostic call to learn the fastest path to double your B2B revenues in just 90 days. Hello and welcome to another episode of the B2B Growth Blueprint Podcast. I am your host, Mark Osborne. And today, I'm very excited to welcome my guest, Carter Gaither. Now, I'm going to read Carter's bio to make sure I get this right because he's done a lot of stuff. Carter is a results-driven executive with deep expertise in corporate strategy, finance, and organizational transformation. Over his 25-plus-year career, he has built and led value creation strategies for middle market companies, directing successful merger and acquisition pipelines, and structured transactions that delivered meaningful shareholder returns. His leadership roles span managing director, chief finance officer, and chief operating officer positions, where he has driven operational turnarounds, implemented enterprise systems, and executed growth strategies across biotech, pharmaceuticals, consumer products, and financial services companies. Carter's experience includes guiding companies through private equity sales, negotiating debt and equity offerings, and creating innovative investment programs. Earlier in his career, he contributed to high-profile sports franchise acquisitions while at River Cities Capital Funds and Arthur Andersen. He's a Boston University graduate and former varsity swim team captain. Carter remains actively engaged in coaching, nonprofit board service, and community leadership. So Carter, welcome to the show.

Thanks for having me, Marc.

Yeah, absolutely. I've been looking forward to this conversation. So, before we dive into some of the topics that you've got a lot of expertise, I know our audience is going to gain a lot from, tell us a little bit about, you know, sort of your career path and what brought you to where you are today.

So, yeah, I've been— I've kind of weaved in and out of boom and bust since I got out of school. And, you know, ended up where I am out of just, you know, luck, maybe misfortune. So, you know, did the thing, you know, worked hard, got into my— got into Big 6, and, you know, had the— was in DC when I did that and got into the world of leveraged buyout venture capital. And then, you know, parlayed that into working for a VC firm here in Cincinnati where I was from. I'm, you know, at the end of the day, I'm a good Cincinnati and I did what everybody else did. I moved away, I found a great wife and moved back.

So— Upgrading the neighborhood as you go.

Upgrading the neighborhood. That's, it's actually part of what we're supposed to do. You get that at birth, you get instructed at birth. So. And then I got the itch to get in on the build side and the investee side and did, went to work for a startup, which by the time I'd gotten there and accepted, turned into a turnaround.

Oh.

And a re-envisioning of the business. And then that was my first jump into healthcare pharmaceutical drug development. And then kind of built a career around founder-led organizations, helping them get to their next step, whether it was turnaround, taking risk off the table, selling outright. And so, and that's where I am today. I've been doing, I've been doing that work for the last 15+ years.

That's great. So it's interesting to sort of hear your perspective from kind of both sides of both funding or being funded, uh, and, uh, the sort of different perspectives that, that, that comes in. And, uh, you know, both of us kind of work in the, the exit space where we're helping companies, you know, prepare for exit. And one of the things that, you know, people always want to do, but it's very hard to do, which is time the market, you know, because a rising tide raises all ships. If, if you could sell at the right time, as they say, yeah, uh, it makes a big difference. But That's, you know, fundamentally a pretty hard thing to do. And in fact, it's sort of overestimated in terms of its ability to impact the success of, of your sale or recapitalization or, you know, other M&A activity. Talk to us about what the market looks like now. And we're in August of 2025 as we're recording this. So heading into fall of 2025, how are you seeing the M&A markets or private equity markets?

Yeah, I would say that in the lower middle markets, middle markets, that M&A activity is, I would say last year was frothy. It was, there was a bunch. And I would say that this year it's not come to a complete stop, but it's, there are a lot of questions out there. And a lot of these companies are, I don't wanna say, fragile is probably an okay term to use. And so, Yeah. the questions around tariffs. There were— what's that? That put a freeze. That was like, well, we don't know what to do. What are we getting? What interest rates? How are we— what's happening with the interest rates? Then you're seeing just trepidation maybe, and like, now's not the time. Capital's not flowing. The deals that are getting done are, I would say, are more strategic. You're not getting max value full buyouts. And so, you know, another bite of the apple type deals are what you're seeing, but it's certainly not as plentiful as it was last year.

So that might not be the most welcome news to a founder who's like, wow, I really wanted this to be my last year in the business. But many founders, operators can recognize that, you know, it's probably worth continuing to stay at it for a while and get the most from the opportunity. So, no reason to rush it. And oftentimes they say, you know, a 3 to 5-year timeline is really what most companies that have successful exits operate on.

Yeah.

So, given that that might stretch what was originally a 3-year timeline into a 5-year timeline for some folks, what do you advise companies that you work with or other people that you advise? What's the best thing for them to do in this environment that's going to really set them up for the greatest success when maybe the market conditions change a little bit, or You know, even just to sort of prime them for that, you know, kind of one in a million unicorn opportunity that does come along, given that it's not as frothy as it was this time last year.

So that question makes me, I mean, it kind of points me back to, or brings back memories of one of my mentors when I first started my career. And they called, the partners called a happy hour on a Friday, afternoon at like 3 o'clock. And I wasn't—

That's either really good or really bad, uh, based on places I've worked.

Yeah, no, it was— I mean, it was, it was, you know, it's time to be social. We, we busted our butt, um, it's time to be social. Let's, you know, and let's do it now. And, you know, it took me like, I don't know, 20 or 30 minutes to like wind down and get ready and, and My mentor came over and was like, "It's time to go. What are you know? What are we doing?" And I said, "Ah, you know, I had to wrap up this email and I had to do this and blah blah blah." And he's like, "No, always be ready. Always be ready." And and that stuck with me, not just you know be ready to exit the office, but just kind of as a philosophy on you know on building business. You know from there we got you know we got into Sarbanes-Oxley. right? I was at Andersen. And so, you know, we all know what happened there. And then Sarbanes-Oxley was born. And the counsel that we provided post-Sarbanes-Oxley was, look, if you're not a publicly traded company, you need to act like a publicly traded company. You may not be spending all the money and, you know, making all the, you know, all that investment, the unnecessary investment, but you need to act like a company. And that's my counsel to to companies now that are like, yeah, you know what, I see an exit coming down the road. I'm 60 years old, I wanna go do these things. This has been my life for the last 40 years, and so I see it coming down the road. And even startup companies, people that are like, hey, this is, I'm gonna start this up and flip it in 5 years. My counsel is always be ready. And so what does that mean? And that means that, look, you wanna be in a position where if you get that offer, if an offer comes across the phone, you're ready, right? And you're gonna get maximum value. And so you need to operate as if you're for sale.

Yeah.

Or you can withhold, or you can withstand a process. And so it's, you know, so today when, you know, you said don't time the market, and I think that's great counsel. I mean, you never want to time— you're not timing the market. I'm, I'm not, I'm not selling in a year, but I'll be ready to sell in a year. And maybe that turns into 3, and maybe that, you know, maybe that's, maybe that's a year and 3 months, whatever it is. But you always want to be ready.

So That's really good advice, obviously. And the thing that also occurs to me about that is the things that you do to be ready are actually things that just make it a better business to run today.

Yeah.

And oftentimes, one of the biggest challenges that businesses have when they get ready to sell is this owner dependency. And owner dependency means you can't go on vacations. You always feel like the roof is caving in on you. If you can either build a support team or build the systems and processes that aren't reliant on you or any one key person, that makes it a better business. And it also makes it more enjoyable to run. And I think there's lots of things like that.

Right.

That are ways to not only improve the experience of running the business today, but that also pave the way for better exit or M&A or recapitalization or any of those sort of activities. So, what's one of the things, what's one of the biggest tips that you would give if a company's like, all right, I do want to make it a better business today so it's more enjoyable to run today, but also a better sale in the future?

What's one of those kind of biggest tips that you might give to So I think there's like a 1 and a 1A, and you touched on it, you just touched on it. But when you're getting ready to sell your company, think about it as you're telling somebody a story.

Yeah.

And you want, you know, what is your story? Is your story, is the main character of your story, is it you? Or is the main character of the story the company?

Yeah.

And if you look at it and you say, hey, the main character is me, you're not ready. You're not ready. If the main character of your story is the company and it's, you know, it's the people getting opportunities to develop, it's, you know, the sales are scalable and sustainable. You're in, you know, you're in the right industry, you're in the right market. You're, you know, you have the ability to pivot, navigate the grays. If that's your story, then you're well on the path. You're ready, right?

Yeah.

And regardless of what the market says, you're ready. And so I think that's one. I think that's one is, you know, who's the main character of your story? The second piece is, and I, you know, I have a bias, but I view the back office, I view the finance department and the accounting department as an opportunity to drive investment. And that's easy, right? Oh yeah, of course, you got all the cash and you put in money and you— no, no, no, no, no. It's, do you have the right people in that group? that are thinking strategically about, you know, how to grow the company. And so, you know, FP&A is a big piece of that, but you can carry that across, you can carry that across the group. What's your AP person doing? Are they just paying bills?

Yeah.

Or do they have a real, a good understanding of impact of cash flow and needs and growth and AR? What's, you know, What's the timing on the AR? I mean, can we negotiate better terms? Can we, you know, can we keep that cash in the company? Are you thinking strategically in terms of looking at the sales? What are those, you know, what sales are driving revenue? And what's, you know, where are we spending money and where are we losing money? Where are we gaining money? So it's really an opportunity right now, I think, to be able to look at your back office and say, hey, are we strategic? Are we, you know, I'll go and I'll talk about, you know, old world CFOs as historians, right?

Okay.

Accountants are, they're historians. They tell you what happened.

Yeah.

And I, you know, there's value in understanding what happened. Those, you know, those who don't learn their history, yada, yada, yada. That said, you know, it's that you really have an opportunity there to be proactive, to say, okay, here's, we know the history, here's the impact. If we make these changes, these things can happen. And we can take, you know, we can take a center within the organization, it's really been an expense center, it's been a cost center, and make it a center of investment and return.

Yeah.

And really drive value. And I go to a great example of that was a company that I worked for and, you know, they were in drug development and the average customer spend in this space was $2.5 million over 5 years. Nice little chunk of change. this company was only capturing the first 6 months of that spend and getting $250,000. And we started to ask why. We started to notice that and started— and we started asking why. And well, there were gaps, right? There were gaps within the offering. And so how do we fill those gaps? And, you know, what's the analysis that we need to do? Do we— is that an acquihire? Is that a merger? Is that— what do we need to do? And the long story short is that we were able to fill those gaps with people that we felt were excellent like everybody else that was in the company. And we took that company from— we increased the value of the company by 5x over 4 years, 3 to 4 years. And so there's tons of opportunity there, especially now that, again, you don't want to time the market, but Market's not really happening. And so, right, are— what are you doing with your time? You know, how are you looking at your business and, and how are you— and what are you thinking about and what, what can you do? And it's— and, you know, it's not— the answer is not always, well, we need new systems, let's spend $200,000 on a new system and we'll spend 18 months and everybody will hate each other by the end of it, but we'll have a new system. Let's, you know, we need, you know, let's invest this in marketing. Let's— it's not always spending capital.

Yeah.

It's just looking at your company. Do you have the right people in the right spot doing the right things? And where, you know, where— what's supporting the company and how— and can you make pivots within the organization to make that grow?

Yeah. So, 2 things you touched on there that really resonated with me. And first is that idea of what's the story of the sale? Is it of you and what you built or of the company? And it's very often interesting to me. So, we work with companies oftentimes preparing for sale and from that marketing and sales perspective, and we'll sort of say like, well, who's your best salesperson? And very often the founder will be like, me, no one can sell it like I can.

Yeah.

And I'm like, I know that you're proud of that, but that's actually a problem. And we sort of try to lead them to that understanding without kind of saying, well, that's a bad thing. Instead, it's, well, then what do you think the new owner is going to think when you're gone? You don't want to be the top salesperson for the company anymore. And so, it's about sort of helping to remove that dependency. And then I also love that idea that sort of these, what are seen as cost centers. And oftentimes marketing is seen as a cost center for companies. And so often it's because they've just been trained to think about top-line revenue as the outcome from marketing. But if you just shift that and think about it as, you know, EBITDA as the outcome of marketing and the sort of structural and customer capital that comes from marketing that's focused on things that drive EBITDA, like getting faster renewals, larger upsells, more referrals and testimonials, then it starts to become an investment center where you can look at the forecast and say, well, for every dollar we put in, we get 3 out. That's also a much better story to tell, you know, that potential buyer than, well, we spent some money and it drives some top-line revenue, which keeps us really busy. But the impact on the bottom line isn't that great. And we kind of never know what it's going to be because we're always, you know, throwing spaghetti at the wall to see what sticks.

Yeah, no, I think that's a great point.

So, we talked about the thing that they sort of should be doing. What's one of the pitfalls that you see within companies that are, you know, sort of thinking about, you know, in preparing for, you know, some event on the horizon? What's something they should be aware of Not just from a positive perspective of, you know, make these sort of model shifts in how you think about some of that back office, but what are some things that they might be overlooking that could be a watch out?

Yeah. And so we talked about creating or telling a story and 90% of the time when your story is about the company, you know, if you Turn the page. It's about the people. Yeah, and and it's you know the what is is not as important as the who. Yeah, and so and I said it earlier, and and you know I a mantra of mine is right people, right spot, right time. Sure, and it's you know and and so if you don't have that, if you have look I've got. I've got my guy. He's been with me for the last 15 years and he knows, you know, he knows everything. And without him, I'm, you know, I'm crippled. That's, you know, that's great loyalty, you know, but look at the role and has the role evolved? And if it's the same role doing the same thing, you know, there are some people out there that are like, hey, this is what I want to do for my life. Right? That's work-life balance, etc. But a lot of times they're, you know, they're there because of, you know, job security and, and they're not really adding value. And so for me, you know, when I, when I get into a company and I start looking at a company, a big red flag for me is somebody that says— you ask them what they, you know, what, what do you, what do you do? And they're like, uh, it's different every day. Every day it's different. Or, you know, I go from one fire drill to the next. And invariably, my experience has shown that those people are creating the fire drills, they're starting the fires.

Yeah.

And then putting them out to, you know, to elevate the importance within the organization. And so I've seen it many, many times. And it's just, it heightens your senses to, again, and it helped me develop my philosophy on what an organization is. And so, and what good looks like. And it's, again, it's, you wanna build a company where people wanna be challenged and they wanna grow. And so, yeah, I mean, those pitfalls are, do you have— are the people, are they doing, you know, are they doing the job that's needed to help you get to achieve your goals as an owner?

One of the great— I love that, you know, they're the arsonist and then the chief firefighter. And they love all the accolades they get for the firefighting. And one of the ways that we smoke out those folks is, you know, by instituting process. Because once you have a process that ensures that you sort of show up as your best self every time, whether you're busy or distracted or whatever it might be. And very oftentimes, it's the people that are like, oh, it would be impossible to document the process that we use for this because it's just too complex, or it's too much between my ears, or whatever it might be. With some coaching, we'll sort of say, well, let's just kind of write down the outline of it, just the skeleton, the bones of it. And then from there, they start to— many people will start to realize actually process can set you free. It's not restrictive. It actually gives you a baseline from which you can iterate and get more creative. But then the folks that continue to resist, we're like, maybe that's the bottleneck.

Yeah, it's, uh, and you need to be careful with the term process, not, not process in itself. A lot of companies, especially the, the lower middle market, middle market companies, there, there are these— I don't know, they consider themselves family businesses, right? We're all, we're all a family. We're not corporate, right? And, and so, you know, being a, you know, they're selling themselves to people as we're not, we're not corporate. And so process is a very corporate idea. And so it's not, it has to be there, right?

Yeah.

You need accountability in your organization if you wanna maximize value, it has to be there. But how you sell it and how you implement it is really important. And so, you know, making sure that, you know, it's not, and I go to, I worked for a company, and worked with a company, and they were a consulting firm, and they didn't have any— like, they were supposed to turn their time in every month, and people were like, well, you know, people are just watching me. I'm like, no. And so we had to really sell why, you know, we were doing— you know, we wanted everybody to turn their time in because It turned out you had about 5 people that were just killing themselves.

Yeah.

To get, you know, to get through this, and they needed help, but they wouldn't raise their hands. They're like, I'm being evaluated on what I can produce. And so flat out were killing themselves. And so once we got, you know, once we got time and billing and we got a process in place to be able to do that, and then people understood what benefits they would get from that, you know, it became part of the culture. But it was— they were, you know, we don't want to work at a place like this that tracks our time. And it's not— it's like, look, I want you to be able to get out of here by 5:30. And that's right.

And hopefully they don't want to work at a place where their person in the office next to them is getting a divorce and losing touch with their kids because they're working all the time.

Yeah, I want you to go see your family.

That's right, that's right.

You elected to have a kid, go spend time with them, right? So it's, you know, it's not a negative. If you throw too much at people too quickly, then that can be a negative. So it's how you work it into the organization, but ultimately it's about the benefit, right? It's about changing the mindset of the organization from being reactive That's right.

That's right. So you're obviously an expert in tons of topics that we could spend all day talking on, but I gotta be mindful of your time. But before I let you go, tell us a little bit about, you know, sort of your work that you do today. Who do you work with specifically and what kinds of things do you help them achieve?

Yeah, so I work with lower middle market companies and founder-led organizations in Yeah, again, helping them. My sweet spot again is helping lifestyle businesses become more sophisticated and increase value so that when the time comes, they can do what they want to do and help them achieve their goals.

Awesome.

And so I'm building out a platform. And so the easiest way to get ahold of me is through LinkedIn. Yeah, it's just linkedin.com/MarkOsborne. I am Carter Gaither. And, you know, as I figure out this platform that I'm working on and the partners that I'm with, we'll have something to roll out here in a bit.

Fantastic. Well, Carter, thank you so much for taking the time to join us today. I learned a lot. I'm sure our audience gained a lot from your insights as well.

Hey, it was a pleasure. It's always fun to talk about building value.

That's right.

It truly is. So anyway, thanks for the time.

Talk to you soon, Carter.

Sounds good.

Thank you for joining this episode of the B2B Growth Blueprint podcast. We hope you've gained insights to grow your business. If you enjoyed this discussion, please rate, comment, like on your favorite platform, and share to others who will find it useful. Do you know a CEO, founder, or leader at an early-stage B2B services tech, or SaaS company who would like to be a guest and share their story, send us a note. Let's schedule a conversation.