Brian Cassady on Business Turnarounds, AI & Leading Through Change

March 24, 2026 00:25:12
Brian Cassady on Business Turnarounds, AI & Leading Through Change
The Victory Podcast with Travis Cody
Brian Cassady on Business Turnarounds, AI & Leading Through Change

Mar 24 2026 | 00:25:12

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Show Notes

In this episode of The Victory Show, Travis Cody sits down with Brian Cassady, CEO of Live Comfortably, the largest manufacturer of bed pillows in North America.

Brian is a five-time transformational CEO with a career spanning consulting, private equity, and executive leadership. Over the years, he has helped drive more than $500 million in EBITDA improvements across the companies he has led, with a clear focus on operational rigor, disciplined execution, and transformation at scale.

In this conversation, Brian breaks down what really causes companies to get into trouble, why fast growth can be just as dangerous as stagnation, and how strong leaders create cultures that can adapt, improve, and win over time.

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Episode Transcript

[00:00:00] Speaker A: Foreign. [00:00:08] Speaker B: Welcome to the Victory show where we interview founders, entrepreneurs and executives to reveal the real playbook behind scaling past the first million or even 10 million or even 100 million in revenue. We go beyond the highlight reel into the hard lessons, the costly mistakes, the key growth inflection points, and ultimately the human decisions that shaped those numbers. And here's the twist. Every conversation becomes a chapter in our Vision to Victory book series so the next generation of builders doesn't have to start from scratch. Today, I'm sitting down with Brian Cassidy, who specializes in one thing, transformation at scale. Brian is a five time transformational CEO with a track record of delivering step change growth in both revenue and profitability. Over the course of his career as a consultant, private Equity Operator, Partner, CEO, Brian has driven more than 500 million in EBITDA improvements across the company seats led. He now serves as CEO of Live Comfortably, the largest manufacturer of bed pillows in North America, where he continues to apply disciplined execution and operational rigor to scale performance. Brian, thank you so much for being here. What, what an interesting career. How often do you get, how do you end up in pillows? [00:01:26] Speaker A: Yeah, probably just about every time somebody looks at my background and says we didn't come from the pillow industry. So how'd that happen? So, well, I think that, and I [00:01:35] Speaker B: get that Live Comfortably is a broad range, but the fact that, that they're known for the pillows like me as a business person goes, there's just a biz company that all they do is pillows. [00:01:46] Speaker A: Yeah, I mean, believe it or not, you know, it's one of those industries where it's kind of a little bit of a cottage industry. There's not that many players in it. It's still relatively large. And you know, it always amazes me when you come across niches like this of products that you see every single day. And you know, there's literally hundreds of millions of them out there, but there's only a few competitors who actually do it right and can produce these pillows at scale to be able to serve the biggest retailers and serve the mass markets. [00:02:12] Speaker B: Yeah, I, I think it, you know, when we were chatting before we got. I wish I would have met you four years ago because I was, I had like a two year window where I probably spent 800 or $900 trying to find a pillow that was comfortable. I finally did, but you could have saved me all that search time. So let's talk a little bit about your journey. You started as a, as a consultant with Deloitte and like, did you, like, was that A sort of by design. Coming out of college, did you know you wanted to be in business consulting or was you had a general idea and life kind of led you that way? [00:02:48] Speaker A: Yeah, no, actually I did target that. You know, coming out of business school, I really wanted to do something a little do the same thing that I did prior to business school, which was to do drive turnarounds of companies, but on a larger scale. And Deloitte had a restructuring practice, turnaround consulting arm that allowed people like myself coming fresh out of MBA school to do just that. So when I was coming out, I knew that they offered that opportunity. A lot of my friends from school were going to bigger names, maybe going to Garmore, I should say bigger names, but names with more cachet, like a McKinsey or something like that, or a BCG. But I knew for the kind of work that I wanted to do with getting my hands dirty and operations and having the ability to really shape the future of a company on a day to day basis, Deloitte really offered that more than anybody else. So I did target that and target consulting. But the objective always was then to ascend beyond that and to eventually become, you know, a CEO and business operator. [00:03:52] Speaker B: So what is it about turnaround specifically that's exciting for you? [00:03:56] Speaker A: To me, it's the ability to make a difference every day. I. I've been in many situations and seen, you know, situations where a company is stagnant and people become stagnant. And in a turnaround environment, you can't be stagnant. Generally you've got to move forward, you've got to improve. If you don't, you end up dead. Whether you end up dead tomorrow or you end up dead three weeks from now or a year from now, if the business is moving in the wrong direction, obviously can't sustain itself. So to me, the really exciting thing is being able to come in and change the trajectory of a business. And the more exciting thing is accomplishing things every single day along that avenue to success. [00:04:38] Speaker B: Are there generally you've done this enough now and I'm assuming you've looked at enough businesses. Are there sort of core things that companies will do that get them into trouble, where they actually need to execute a turnaround and if so, yeah, two or three that come to mind that you could share? [00:04:54] Speaker A: Absolutely. I mean, one of the first one usually is kind of outgrowing your capabilities. We see it all the time, whether it's an entrepreneur who's kind of can't make that inflection point of leaping from one level of revenues to the next because they either don't have the skills or they don't have the team around them or, or they don't have the pos, the processes in place to support a larger business or whether it's, you know, more often than not, you see these days a company that's grown via acquisitions and maybe had grand plans to do all sorts of things with those acquisitions and to integrate them properly and to form a cohesive company out of it and instead just got lost in the kind of the glamour of conducting acquisitions and never did the back end part of making the pieces all fit together. You know, that's kind of one of the number one, you know, that is, I would say the number one issue that I've seen that causes distress at most businesses. Second, there's obviously, you know, economic cycles, whether it's a macro cycle that's the entire economy, or whether it's just a sector specific cycle that is reliant on some kind of external stimulus or some kind of change in technology or whatever. That's probably, you know, the second leading one is the inability to adapt to some kind of macro change in their market environment. [00:06:10] Speaker B: It's, it's so interesting to me that we've got like a company that's growing and they're acquiring businesses and you think, oh, that's great. And then like a lot of times that's ended up what gets them in trouble. [00:06:23] Speaker A: No, but you know, but it happens often and much, much more often than you would think. Probably half of the time in my career that I've been called in to help a company that's in trouble, it's because they grew too fast and more prepared for it. [00:06:35] Speaker B: Wow. So on the flip side then when you come in, let's say you've been hired to come in and execute a turnaround, what's the first like again? Is there like a core, like your first six months? Is there sort of a core process you're going to go through to like go about ready, like riding the ship or getting. Bringing balance back to where they're at? [00:06:57] Speaker A: Yeah. So a lot of people have different playbooks. They apply and I'll talk about it. I don't have a rigid playbook per se, but my management style follows a certain path. [00:07:08] Speaker B: Right. [00:07:09] Speaker A: Which is the first thing I do is come in and explain to people that explain the entire management team and all the way on down the ranks that what we're doing now as a company is not getting the benefits, not getting the results that we want one way or shape or form. I try not to attack the past and try not to attack what's going on now, what's, what's being done at a business. And I more frame it that it may have worked at one point in time, it may have been appropriate and decisions may have been the right ones, you know, when they were enacted, but either the markets have shifted or the longevity of the strategy has played out, or whatever the circumstances are, but the status quo is no longer acceptable. So I try to push businesses to the thought process that there has to be change. Because number one, like I just said, when you're a turnaround situation, if you don't change, you're going to repeat the same mistakes or repeat the same cycle and end up, you know, obviously not performing. So that's the number one thing, is to set the expectation there will be change. Then after that I enact change by ensuring that you're looking at scientifically, you're looking at and very objectively all the variables that go into performance. And when there is a, you know, something wrong with the business, you dive deep into exactly what the problem is, why you know, what is causing, whether it's a cost issue, whether it's a lack of sales, etc, objectively, forget about the past and just say, you know, what is preventing the business from performing and make sure that that decision or that thought process is rooted in data. So you're always looking to validate. So what somebody believes is their hypothesis around what is wrong and what needs to be fixed and how to fix it by looking at hard data and proving it out before you go and do it. You got to walk a little bit of a tightrope between demanding data and demanding analysis and moving quickly because generally you have to move very quickly. But I preach to everybody that you want to make sure your decisions are rooted in data, because if they're not, you have a tendency to kind of follow old paths or to follow truisms and what have you that you know, obviously may have gotten the business in trouble in the first place. So you really need to make sure that people are starting to look objectively at the situation, casting aside any kind of premeditated or pre preconceived notions around what the business should be, how it should operate, what's the path to prosperity, and really just kind of starting with a clean sheet, making sure that you're validating everything. May be things everybody's doing is perfect, but validate it, at least for me, when I'm coming in from the outside. I want to make sure it's validated, to make sure that we haven't missed anything as we go on the journey to success. Yeah. [00:09:57] Speaker B: I once heard a. Had a friend who had a pretty significant business, and the market shifted and wiped out, like, 90% of the revenue in, like, a couple of weeks. And everybody in the company, you know, they had 120 some employees, and they were just, like, panicking. [00:10:13] Speaker A: And. [00:10:13] Speaker B: And his older brother was the operations person. And so he's in there and he's, you know, kind of going on. His brother was just like, okay, just stop. He's like, let's deal with the circumstance, not the emotion. [00:10:24] Speaker A: Yeah. [00:10:25] Speaker B: Saying that was the biggest lesson he ever got in business because everybody was so panicked and running out of fear and whatever. And his brother just came in and said, can't control any of that. This is the actual situation. How do we attack this? And, you know, and then eventually they recovered and moved on. But I thought that was really interesting. And again, right from. From an outsider perspective, and maybe even to point in my own business, just seeing how. How easy it is sometimes to let emotions kind of dictate some of the decisions you're making instead of doing what you're doing, which is like, let's just get data. [00:10:56] Speaker A: Yeah. No, it's hard because, you know, for a lot of people, you know, when they've managed a business to the point of success, and then all of a sudden the success stops coming. You know, they believe in what they've done in the past. They have a lot of pride in how they've built a business. And a lot of times they don't recognize a shift and instead just believe that they're not working hard enough or they're not executing as crisply as they used to. And sometimes that can be the case. But more often than not, there is something that needs to be changed. And if you don't recognize that you need to change it, then, you know, you're generally fighting a losing battle. Yeah. [00:11:32] Speaker B: So what are some things that businesses can do today where it feels like things are moving at such. Especially with AI everywhere, just feels, like, hard to keep up. So how does a business avoid following, falling into the status quo so that they can always kind of, you know, I guess, keep steadily growing instead of hitting the complacency that. That clobbers that. [00:11:55] Speaker A: Well, I think you mentioned it with AI, or at least you alluded to it. I think part of it is intellectual curiosity is never thinking that you've achieved kind of the panacea near that you are, you know, that kind of alpha competitor that is always at the top of your game and is never going to be knocked off. Right? You always need to be looking forward and saying, okay, what's the next thing that could hit us? Or what's the next opportunity? Or how could we do more, you know, be better, etc. I'm a big, big believer in continuous improvement. I've done a lot of manufacturing throughout my career and, you know, learned from some of the best in the kind of the Toyota production system of how to apply continuous improvement methodologies across just your entire culture, which is really what you need to do it. You don't have to be a manufacturing firm to employ those kind of tactics, but you have to understand that every single day is a battle to figure out how to do things better, more efficiently, more safely, to create some kind of new competitive advantage. So the complacency that creeps in is the dangerous part, right? You gotta always be intellectually curious and looking at it. So, like, AI is an example, you know, you can't just sit back and say, okay, I'll figure out this AI thing when it happens. Because by the time you figure in today's culture and today's technology, you know, by the time it happens, you may already be too far behind. So you have to be in front of it and you have to be looking at and evaluating by the same time. At the same time, you need to make sure that you don't adopt something so quickly that you're leaping into something that then will later prove to be kind of a, if you will, a mirage in terms of its efficacy or, you know, in terms of the impact it can have on your business. I've seen that happen a lot as well, too. It goes on in markets as well. You know, there's bubbles that occur all the time that are based on kind of fads or based on, you know, kind of theories of what's going to happen in the future that, you know, you sometimes, you need to be cautious about. You need to step back and again apply a very objective look and say, is this really what it's cracked up to be? [00:13:59] Speaker B: So, so in your own career, what are, what are a couple of the big mistakes that you've made that have also taught you some of the best lessons you've ever had? [00:14:14] Speaker A: Big mistakes. I mean, so there's sometimes some personnel decisions where I've waited too long to pull a trigger on certain people. Right, that happens. Or I don't know if it's pull the trigger on certain people because I generally like to try to work with the people that I have and just try to coach them up to performance. But it's more, you know, not. You're being a little bit bashful about getting in and coaching them up. That was earlier in my career. I think now I'm not nearly as shy about it. But, you know, when I look back over time, you can always say there's a certain point when you relied on either a person or a methodology for a little bit longer than you should have. It's just what I said before, you know, you get stuck in a rut and you say, okay, I'm not wrecking. You don't recognize the change that needs to be had, and then you make it a little bit late. So I would say that's one mistake. I'm sure I've made many, many more. What about mistakes you. [00:15:06] Speaker B: Maybe you've seen people you've worked with that have made mistakes, that have taught you a lesson and doesn't necessarily have to be your own. I was like, yeah, look, everybody with scale, it's always like, oh, we're doing all this stuff, right? And I'm like, yeah, but a lot of times, you know, for me, like, in my business, I've made a lot of mistakes along the way. That's where my business has gotten to the. Where it is. So I'm just curious at the scale you've operated. If there's been some. Some big ones. If not, that's fine. [00:15:31] Speaker A: Yeah, look, I think the biggest mistake is, is losing your objectivity, right? The minute you, you lose your objectivity and you start thinking that, you know, you don't have to rely on information and data and that instead you can kind of rely on your. Your wit and your intuition, your history of what's going on in the past. I mean, a lot of times, history is a good guide to the future. Don't get me wrong. But if it's proven out, but it still has to be proven out in the data, that that's true. Right. But all too often, I see people who just kind of stray from just the foundations, the normal building blocks of any kind of business decision and allow their emotions to take control. And then you start, you know, at that point in time, if your gut reaction, your emotions are wrong, which emotions often are, you start to run into trouble. And I've seen it over and over again. And it's hard, especially for entrepreneurs who've had a lot of success in their life. You know, it's a hard thing to admit that maybe the path you're going down, you know, is not the proper one or you've made a decision that you don't want to, you know, own up to. But I think most successful entrepreneurs will tell you that they made many, many mistakes and the key is recovering from them and it's pivoting and having that ability to kind of recognize it and move forward and be willing to do something different or willing to abandon, you know, kind of a sacred cow that was there before once they recognize that something needs to change. [00:17:00] Speaker B: Interesting. So you talk about, you like to coach your leaders up. So what, what, what do you look for in a, in a good leader and what, what are the skills that you try to help them gain as you're coaching them up to help them get to a new level? [00:17:18] Speaker A: Well, I think the best people that I've met and the most, the best leaders that I've seen are ones who, who like to make sure that their organization is behind them. Meaning that they are developing an organization that is agile and can support the business mission and are focused on doing that and creating both the culture and the enablers behind it. Right. To allow an organization to thrive, you have to give people the ability to grow. And you know, by doing that, you develop a better team and you develop a better culture. When you give people growth opportunities and you give them responsibility and you challenge them to exercise those growth opportunities, you know, I find that you get really great results. So what I look for in leaders is people who have more of kind of a servant leader mentality, who don't make it about themselves and don't make it about kind of command and control, but make it more about developing an organization where everybody in the, in the entire company is focused on delivering better results and contributing to that. Now you're not always going to get there, right? You, you just. It's unreasonable to expect that every person that comes to work every day is going to be thinking of how do I make this place better, how do I do better, et cetera, et cetera. You don't need 100% of the people on board, but if you can get just 20% of your workforce thinking that way, it's really powerful to walk in every day and know that you've got an army of people around you who are all thinking a like minded fashion. What do I do better? How do I get this business to the next level? How do I create a differentiable competitive advantage? Those sorts of things becomes really, really powerful. I've driven some turnarounds in record time just by harnessing the power of the organization and letting people know that, you know, they have the ability themselves to impact the outcome of a business. [00:19:10] Speaker B: So what do you do specifically to motivate employees to get to that point? [00:19:16] Speaker A: I do a couple things. You know, one, I believe in a lot of praise, right. I understand that sometimes, obviously, you've got to give some tough feedback to people if they're not moving in the right direction. But what I find is that if you give people praise and recognize their efforts, and especially if you do it publicly, you do two things. One, you engender a sense in people that, you know, that you really are behind them and you're applauding their victories and that you're relying on them. Two, you also tend to create kind of an echo chamber where others see that and say, okay, you know what? That must feel good. I want to be part of that. And you create a situation where the organization understands that everybody should be kind of pulling their own weight and doing their best to help the company succeed. And as you do it individually, you'll get celebrated. So I like to do a lot of, you know, very public, you know, acknowledgments of great successes. And it doesn't have to be huge things either. I kind of preach to everybody, all levels of the organization should be attuned to opportunities for improvement. So whether it's somebody who comes up with a brilliant idea for a new product or a new technology that is going to change the industry, or whether it's somebody on a shop floor somewhere who just figures out how to do something five seconds quicker, you know, or reduce material costs in their. In their product. Either way, just celebrating that kind of mentality and those kind of improvements and documenting them and demonstrating them to everybody else, I think is. Is a real winning strategy. [00:20:57] Speaker B: So with live comfortably, what are. [00:21:00] Speaker A: What. [00:21:00] Speaker B: What are your goals this next few years with that company? Like what. What are you hoping to. To achieve? Where do you want it to get to? If you can share that publicly, I [00:21:12] Speaker A: probably should some of it in a competitive marketplace. So I think that there are certain things that I'll. I'll reserve. But I'll say as a business, you know, as markets evolve, we have to evolve with them. And I think in our particular business, there are some open segments of the market that I think as an industry in general, we haven't done a great job. One of which is ecom. I know there's a ton of E Comm out there, and you know, Ecom is now, you know, something that's, that's been around for decades and decades know, but still, if you look across the landscape, if you look at market shares in E Commerce, they're tiny compared to the way they are in retail. So I might have a 30, 40, 50% market share at a given retailer and you might find competitors that have similar market shares at within on a shelf space with retailers. But there's nobody out there that really has anything even approaching that market share in the E Commerce channels. So I think that's a big one for us, to tell you the truth. And I think you'll see, you know, there are a lot of our retail partners are taking the lead in that and preaching that as well too. So I think there'll be a lot more emphasis on that in the future and we need to be part of that. That's the one area where I think, you know, us, you know, as a business, live comfortably, probably hasn't participated in the opportunities that are out there. Having said that, nobody has. So it's open space. So that's great. [00:22:41] Speaker B: Yeah, that is exciting. So you know, having done this for, for quite some time now, what is it about sort of the today's world and the opportunities that, that all this technology is opening up that has you excited about the future just as a business leader and as a business owner and, and for business in general. [00:22:59] Speaker A: Look, I think AI is exciting. You know, I kind of look at it as like when, when laptops first came out or computers and then spreadsheets and then databases, you know, all that stuff existed on paper before and you could do the math and you could do things, you could do calculations. But obviously there was a step change in productivity when that technology was applied. Then you had the Internet that came along and allowed you to do faster research and transact more smoothly and took a lot of the friction out of the system, that sort of thing. And I think, you know, AI is going to be a very similar types of type phenomena where all of a sudden people are going to become much more quicker at what they do. I don't think it's going to replace people the way, you know, the way many people fear. I think it's much more going to become just another tool, another enabler when you think about it. I came into the business world at a time when spreadsheets were new and my first job, I'll tell you flat out, my first job I got because I knew how to run a spreadsheet and my boss who was just a few years older than me, had never been really introduced to one. So I looked like a genius for no other reason than I knew how to operate a computer, and he really didn't. Now, there's nothing against him. Very, very intelligent guy or what have you, but it's just that kind of technology, when that's adopted by early adopters and, you know, at first it can be a little bit daunting, a little bit scary for people, but, you know, once it comes, once you are able to adopt it, you differentiate yourself in terms of the skills you can bring to the table, the speed that you can work at. And I see the same thing here. There. [00:24:34] Speaker B: I love it. Well, Brian, this has been a fascinating conversation. Thank you so much for taking time out of your day to be here. I really appreciate it. If somebody's listening to this and they want to connect with you, LinkedIn the best place. [00:24:46] Speaker A: Yeah, that's probably the best place to reach me. You can always email me my. You know, my email address is B, C, A S S A d [email protected] so you can reach me there. But LinkedIn is just as effective these days. [00:25:01] Speaker B: Love it. Thank you so much. [00:25:03] Speaker A: Excellent. Thank you. Travel.

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