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A CEO’s Blueprint for Career Success: Leading with Love to Drive Performance and Culture

Leadership right now feels heavier than it did just a few years ago. Teams are stretched, expectations are high, and many employees are quietly disengaged. In fact, Gallup’s 2025 U.S. data shows that only about 31% of employees are actively engaged at work, leaving the majority feeling disconnected or indifferent. For CEOs and senior…

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By Mike McCalley · Automotive IndustryBusiness TurnaroundCeo LeadershipCompany Culture
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Key takeaways

01

Robby Humble's 'leading with love' philosophy—combining nurturing and tough love—drove 20% YoY growth in Q3 cash collections at Penn Warranty without new products or marketing.

02

Creating psychological safety encourages teams to surface problems early, enabling faster resolution and stronger organizational performance.

03

Career breadth across six industries and a difficult period outside corporate America shaped Humble's resilient, people-first approach to leading complex turnarounds.

Leadership right now feels heavier than it did just a few years ago. Teams are stretched, expectations are high, and many employees are quietly disengaged. In fact, Gallup’s 2025 U.S. data shows that only about 31% of employees are actively engaged at work, leaving the majority feeling disconnected or indifferent. For CEOs and senior leaders, that’s not just a cultural issue—it’s a performance risk. And in many cases, it’s the difference between a “storybook” career success narrative and the harder, messier reality of leading when it counts.

So what does it actually take to re-engage a workforce and drive meaningful growth at the same time? And can something as unexpected as “leading with love” become a serious business strategy?

On this episode of Get Vertical!, host Mike McCalley sits down with Robby Humble, Chief Executive Officer of Penn Warranty and Preferred Warranties, to explore an unconventional leadership philosophy that has fueled a company turnaround. Humble shares how leading with both nurturing and tough love helped reinvigorate a struggling automotive warranty business, delivering 20% year-over-year growth in Q3 cash collections—without introducing new products, services, or marketing initiatives.

Key highlights from the conversation…

  • How redefining accountability through “nurturing” and “tough” love transformed leadership dynamics inside the organization.
  • Why creating psychological safety allows teams to bring problems forward early—and solve them faster.
  • How career breadth across six industries—and a hard-earned detour outside corporate America—reshaped Humble’s definition of career success and prepared him to lead a complex turnaround.

Robby Humble is a CEO and investor with leadership experience spanning seven industries and every major go-to-market model, including B2B, B2C, B2G, and D2C. He has held C-level roles in public and private equity–backed companies, helped lead a $720 million company sale, driven a 40%+ EBITDA CAGR through an eight-acquisition roll-up strategy, and overseen more than $1 billion in annual sales as Chief Revenue Officer. He is currently CEO of Penn Warranty and Preferred Warranties, where he is leading a multi-year transformation centered on performance and culture, and is the author of the forthcoming book Love & Leadership, a blend of memoir and leadership framework drawn from real experiences inside high-pressure organizations.

Article written by MarketScale.

Video TranscriptExpand ↓

Hi. I'm Mike McAuley. Thank you guys so much for joining us for today on Get Vertical. My guest is Robbie Humble. He is the CEO for Preferred Warranties. He's got an incredible story about his career and just being able to go from setting hard targets and achieving incredible storybook type results. But also the story behind the story, which is it's not always as clean as it looks. Right now he's in the middle of, leading a turnaround with preferred warranties and, just some great results there. Can't wait to dive in and I'm excited for the story you guys are going to be able to hear about an unorthodox approach to leadership that drives incredible results. Robbie, thank you so much for joining me, man. Thanks for having me. Yeah, this is great. I know we've been talking about doing this for a while and, just hearing your story personally has inspired me. And I just want to say thank you for sharing it so far. And I can't wait to be able to hear more about it. Yeah, Mike, thank you for saying that. Yeah. So, you know, everybody's got a story, and it starts at different points. You know, when I think about you and I looked at your, your background and your bio, what's out there on LinkedIn, it just, it looks like everything's always gone perfectly, right? It's one of those, went to a top engineering school in the country. And then from there, you know, went into one of the, a blue chip company with Raytheon, part of their leadership development programs. And, and then from there to Harvard Business School, and then through another series of different leadership profiles and development and whatnot. Do you mind, how did you end up in how'd you start? Right? Which where did does it start back in in high school and when you were younger and learning a work ethic? What what happened? Yeah, no, thanks for the question. So I always say that if you just looked at LinkedIn or looked at my resume, you would get, the wrong impression about me. As you said, top tier engineering school, Harvard Business School, a career that, in many ways looks up into the right, but it really all started in a small town in Oklahoma. I grew up in a town when I graduated high school, we had three thousand five hundred people in my own town. Okay. Which is less than Not for graduating class. Oh no. The, the entire town. Okay. Graduating class of one hundred and twenty. Okay. And, I was very active as a kid. I played all the sports. I played in the band. I sing in the choir. I was academically excellent. And, I just, I had a very active mind and that mind went into literally at every asset or facet of life from the arts to athletics, academics, philosophy. Even as a high school, kid, I was thinking about things of that nature And I was a big fish in a small pond. I'm very grateful for the upbringing that I have because that combined with the experiences I've had since enabled me to have the same conversation with a blue collar farmer as I can with the CBO of a fortune five hundred company. So I always start with that. And, and it's important to also mention, yeah, went to a top ten university, but I paid my way through school. So I've given my parents more money than they've given me since I graduated high school. And, I worked anywhere from two to four jobs in addition to like selling in an engineering program. I got a mechanical engineering degree, but I learned work ethic from a very early age. I also learned the value of not procrastinate. So I was very quick to do my assignments so that I had plenty of time to study for exams. So work ethic and focus were very much a part of my upbringing and through my college years. And then I entered corporate America at twenty three years old. I was leading a team of nearly fifty people, in a manufacturing environment. Had never been in a manufacturing factory before. I'd obviously never led people before. So this was my first real job. And, by all outward appearances that went swimmingly well. And, eighteen months later, I applied to Harvard business school and I'd always had a vision. I would say my sophomore year of college, I was inspired to attend Harvard business school. And so eighteen months in, to my career, I applied to Harvard and got in. I was in the bottom, youngest ten percent of my class when I got here. And that's been a theme of my career as well. I've always been the youngest person in the room, repeatedly. You know, you're hitting the point where that's gonna change. It's already changed. My yeah. My, VP of ops is, three years younger than me, and, I'm starting to feel like an older man. Yeah. But with age comes wisdom. So, you know, I value that. So, went to Harvard Business School and, graduated. I wasn't at the top of my class, but I wasn't at the bottom. So, graduated from there and was really inspired there to be a CEO. And there's a quote by Clay Christensen, who a lot of your listeners will know, just a, business guru, a, Innovators Rule of May I? What's that? The author of the Innovators Dilemma. That's right. And he coined the term disruption, in the 1990s. And Clay, my second year of business school got diagnosed with brain cancer. And he, as a result, thought he was dying. He ended up dying ten years later, but he, the prognosis was not good. And so he gave my graduating class at HBS, a speech called How Will You Measure Your Life? Where he took the frameworks that he uses to teach in his class, which I attended. I was in his class and, he applied those frameworks to life. And I've forgotten a lot of what he said. It's now a book called How Will You Measure Your Life? Highly recommend it, if you're so inclined, but I'll never forget something he said. He said, management, when done well, is the noblest of professions because you have a more profound impact on the lives of your employees and the people in their lives than virtually anyone in their lives. And that not only inspired me to be a CEO because I wanted to affect the lives of as many people as possible. And in fact, when I graduated from HBS, they had us write a letter to ourselves where we wanted to be in ten years and my letter and put in a not low and my letter was, I want to be leading a business of enough significance that I was affecting the lives of a thousand people or more. And so Clay really launched my vision for what I wanted to do in my career. And then I went out into the real world again. And, over the course of the next fifteen years, again, my career looked like it was up into the right. I worked for Celanese, a global chemical manufacturer. I, in fact, I won't run you through the whole resume, but I've worked in six different industries. Actually, it is worth noting. Okay. Because it is right. You you were you were at a defense contractor. Yeah. Then you went to back to school. Then you went to a chemical manufacturer. Yes. Then to rent a sutter. Yep. Right? So furniture consumer goods. Right? And then from there, where did you go? I went to Netspend, which is consumer finance. Okay. So bank account alternative. Yeah. After we pay debit card. And then? And then I went to an automobile warranty company. Okay. So, and we'll, and then, and then you bought a company at that point? So an auto franchise is. All right. So you bought into a franchise and then you went back into corporate. So we'll come back to all the details behind that in a second, but I think it's important. I was talking to a friend and colleague of mine, and he's been extremely successful in his career as well. And one of the things that, that people told him at the beginning was you can choose to go breadth, you can go for breadth or depth. And, but a lot of times what they found when he was talking to, the senior HR person in the company that was responsible for placing top talent is the people that had a series of different experiences that would go flat or even take demotions on paper, right? To go into other functions and get more exposure or go to other regions of the world or whatever, were the ones that ended up and were the most successful leaders because they had a better perspective, a more holistic perspective on the role. That really resonates with me. When I had the vision for being a CEO, my philosophy from the very beginning was I want to see as many different business models as I can. And so I've worked in business to government, business to business, business to consumer and business to business to consumer. I've scanned or spanned the entire spectrum and I have worked in pretty much every function other than HR and IT. And so my philosophy was if I want to lead an enterprise in an unknown industry, twenty years out, I want to understand every business model that's out there. I want to understand every go to market strategy that's out there. And I want to speak the language of as many functions within that organization as I can. And so it has been a career of breadth very much so, and, relatively rapid iteration. You know, I was with my last company for six and a half years, but before that it was, the longest I'd been was three years for one, one gig. And before that it was typically eighteen to twenty four months. And so I rapidly iterated through different business models, different industries, different functions with the guiding principle of I'm going to be a CEO one day. And I want to understand how every, all the different parts fit together. Yeah. That's great. That's fantastic. Okay. So yeah, you had this exposure across different industries and different functions and, and each one set up the next stage for you, so to speak. And then at some point you got to a point where you're like, okay, I'm ready to, ready to lead a business. What, what happened? Yeah. So I was ready a long time ago, or at least I thought I was. And, about, I guess it's been two years ago now. I got impatient and I decided I was not going to wait for somebody to make me a CEO. Was going to make myself a CEO. Okay. So this is great. Right? Because I know a lot of people get anxious or a little bit enthusiastic about their careers. Yeah. And impatient is what I can word. Yeah. I can't tell you the number of times that I had people in my career, my leaders or whatever said, just be a little more patient, slow down. Right? And I'm like, no, gotta go, gotta go, gotta go. And there were times that even looking back now, was like, okay, yeah, I should have been more patient there. Or, and then there were other times where I was like, no, I needed to be more impatient. Right? Because hindsight's twenty twenty. And, but as I, as I think about that, before we dive into that, that impatience or that drive, Let's hit pause real quick and talk about your current role. Okay. And talk about your current company. And then let's come back because I think as, as we, I think this sets a lot more better about like the experience that you had and the path. Yeah. So tell us about Preferred Warranties. What hap you know, what's the company? What was the situation when you came in? What's it look like now? Yeah. So Preferred Warranties, is an amazing company. It's actually, it's two companies, historically known as PWI and Penn Warranty. Okay. And they're owned by the same parent. We are owned by the same parent and we are actively working on integrating those two companies into an umbrella of preferred warranties. Okay. What do they do? So we are in the automotive warranty industry. We sell auto warranties. So you call my house? No, no. And thank you for asking for the clarification. We sell automotive warranties through car dealerships. Okay. And, and then adjudicate the claims on the backend. Okay. We've got about a hundred employees spread across the country, and run roughly total sales about forty million dollars a year. Okay. That's great. Yeah. With a hundred employees. That's efficient. Yeah. Yeah. Yeah. All right. So automotive warranties through auto independent automotive dealers. Yep. That's right. Okay. And, yeah. So you guys sell exclusively to automotive repair shows. Correct. You don't sell to the consumer. Correct. All right. Yeah. So what was, how's, how'd you find the company and what was the situation? Yeah. Well, I was looking for a job, which we'll revisit. Yeah. But I called, this is helpful for those that may be in this transition time in their lives. I called investment bankers. I called private equity guys that I knew and I called recruiters. And it was actually an investment banker that knew the company well and introduced me to them. I got to know a gentleman named JT, who is the CEO of a parent company. So we're publicly traded and it's essentially a holding company. And so JT, the CEO of Kingsway Financial Services, interviewed me, gave me a very thorough interview and, things were a doubt. He handed me the role and I started in, on March thirty first of this year. So I'm, about eight months in at this point. Okay. And the situation, the company to be frank had been struggling for some time. And, and, you know, I think in many ways people were looking for hope of a different kind of future from what they were experiencing. And I came in and, and started to change things pretty quickly. And this will run-in the face of some business books, but, made some pretty major personnel changes early on. I made the decision for us to go fully remote on my first week in the office. I, started the work on a number of strategic initiatives that were going to help us drive growth for the long term. And the current state of the story, it's not the end of the story, but it's the current state. We have reinvigorated this organization. And I talked to the founder a couple of weeks ago and gained perspective that we're not doing anything new. In fact, in many ways, we're just remembering who we are. Okay. And we can unpack that if it's helpful, but, the company has really been reinvigorated. And there's a couple areas I would draw attention to. The first is financial performance. And in the last few months, we have, and we're publicly traded, I can reveal only so much, but from a cash collection standpoint, we went from flat to down prior to the new leadership to, the last few months for delivering twenty percent year over year growth in each month. That's And it's important to note, we haven't had new products. And is it okay for you to share that? It is. Okay. It is. That's, that's on the street, for Q3. I'm only speaking to Q3. Yeah. So, we have, we had delivered that and it's, it's incredible, the financial performance that we've achieved. And I should note, no new products, no new services, no new marketing, just a different way of lead. And that's not to say anything about my predecessors. Yeah. Cause they're good men, that were doing, the right things, through their perspective. But I bring a very different perspective to business leadership and it's working for us. Yeah. So, all right. Oh, there's a variety of different, operating and leadership philosophies that are out there. So when you say you bring a different leadership style and different philosophy, what does that mean? So I bring a very unconventional philosophy, and that is one of love. Okay. So you guys hug each other a lot? No. Or what? No. It's not weird. Thank you for the clarifying question. For me, love is two parts. Yep. Commonly refer to nurturing love, and we talk about tough love. And love without tough love is not what's going to drive business performance. So it's not about hugs and kisses. Yeah. It's about creating safe spaces for people to be themselves, creating safe spaces for people to show up without all the answers. I people like the phrase, don't give me problems, give me solutions. I say, give me the problems, come with some ideas, But you have the safety to not spend all night thinking of bracking your brain and stressing out and not spending time with your family, trying to figure out the answer to the problem. Shut your day down at the end of the day, be present with your family, and when you come back tomorrow, share with us where you are and we'll figure this out together. Yeah. And so we create a safe, a space of safety for people. And we also have tough love. So we talk about courageous leadership as one of our values and courageous leadership, as we articulate it, is having the courage to speak what's on your mind, to have hard conversations, to, to make sure that, that all the perspectives are at the table and having the courage to do so. Now to make that happen, as I've said a couple of times, you have to create a space of safety. And we've done that. And we also bring the nurturing side of love, which is creating that safe space and showing people appreciation. And we've built systems for this. We have a digital high fives that we're operating in the, in the remote environment. We're bringing to bear a capacity management system where on a monthly basis, our, every single person in the company does a quick survey and adds comments as to what their experience is in the company and are they overcapacity or under capacity? And you can get a heat map for what's happening in your organization across the board. And that facilitates conversations. Some of them warm and fuzzy, some of them more difficult. Right. And so it's not just a philosophy, it's an operating system, as I referenced earlier, and operating systems have structure and tools and systems to be able to drive the results you won't get. I love that. I think that's fantastic. It sounds a lot, a lot like, what Patrick Lenzioni would look at in his dysfunctions of teams. Right? And, I'm I'm a huge fan of what he's written and his approach to it. I we've talked about that in the past, but, you know, he talks about, you know, you've got to lead with trust. And, if you don't have trust, you don't get out of the gates. Right? And the difference between transactional trust and inherent trust, which is somewhat of what you were talking about. Right? And the difference, the way that I understand it is transactional trust is when I place an order with Amazon, I've got a ninety eight, ninety nine percent confidence level that it's going to be there when they said that it's going to be there. Right? Well, to a certain extent, for a while, I had one hundred percent confidence, you know, and then a couple of glitches along the way. But still, there's a high level of trust that it's going to be there. Well, that's transactional. But inherent trust is the ability to be vulnerable with one another and, and share our strengths and our weaknesses, the moments when we, when we blow it, right? Without with, and to your point, the tough law still exists, right? There's got to be accountability, but there's a difference between blowing it for the right reasons and blowing it for the wrong reasons. And the way I always thought about it is blowing it for the right reasons is we tried, we, we gave it our best effort. We, we set the goal. We did all the right things and it still didn't work out. We're not sure why. And that's when you were talking about bring the problem to the group, we'll solve it. Right? It's like, Hey, I, I assigned, I'm the res I'm the one that's responsible for delivering this result. It's not on track. It's not hitting the right paces. I think I've exhausted my well of knowledge and ability to do this. I need help. Right. And you're doing that proactively. And when you do that proactively, right, the team can get ahead of it and figure it out. It gives you the ability to look around corners. And Lenciani's model is, has been highly influential on me. He talks about vulnerability based trust and only with trust can you have conflict in a healthy way. And only with conflict can you get commitment because every voice is heard. And only with commitment do you have accountability and only with that can you get results. And, you know, I'll draw a bridge for people because I understand that love is a provocative word in business. Really what I'm talking about to borrow phrases from the past is servant leadership and accountability. And I want to mention one point before we move on, Mike, the financial results are astounding. And I'm so proud of what this team is accomplishing, just by unlocking their inherent capability. Right. What's even more important is the change we're having in people's lives. And I have spoken with a number of people in my company about how are you experiencing this leadership style. Right. And I've had numerous bits of feedback from people and bits is probably the wrong word. I've had numerous people pour out, their emotions around this experience. Indeed we're not just producing financial results. I'm hearing stories of people who are more present with their families. They're working harder than they ever have, but they feel light. And, and they're, my, one of my favorite, scenarios was, one of the, one of the leaders on my team said that for years she had the Sunday night threat. And she said, I've always lost sleep in this company, but it used to be because I was so stressed about what was happening the next day. Just said, now I lose sleep because I'm so excited about what I have to do tomorrow that I can't stop my mind for thinking about it. And, and it's changing just as my vision was, when I wrote on that piece of paper and put it in an envelope at Harvard Business School. We are not just changing a company, we're changing lives, and not just the lives of our employees, but the lives in their closest spheres, the communities, the families. Yeah. And that's what it's all about for me, Mike. I'm very ambitious and I'm very proud of the external performance indicators. But the reason I wanted to be a CBO and what drives me every day is to change lives for the better. And I really, I really genuinely mean that. That's fantastic. I love that. And, well, and when you're, I guess there's there's two parts to it. Right? There's when you're executing on that and it's, it's incredibly rewarding. I think there's another part of it, which is, you know, they, they say values are great and they're easy to live by when things are going right. But you really find out what your true values are when things aren't going right. Right. When that's when they get pressure tested is, are we making the decisions outright? So question for you, stepped into a turnaround situation, things were going down into the right. All right. And, and headed in the wrong direction. And you had to stop that and stop the bleeding, correct it and, and go. So when you came in, by definition, you came into a tough situation where the values get tested right out of the gate. Did they get pressured tested as you were going through that? I mean, or did things immediately respond the way you wanted them to each time? There were difficult moments along the way, even in this fairytale story of the last eight months. Yeah. No, it's less a story of getting resistance and pressure testing and more of a story of courage. Okay. So I am immensely grateful to JT, my leader, CEO of Kingsway for giving me the trust and the runway to lead the way that I thought I should lead. And he absolutely pressure tests business decisions and he that's his job and he does it really well and I'm grateful for it. And it took a lot of courage for me. That's my first role as a CEO. I had a theory about the way things should be done, but this was an experiment. And it took a lot of courage to do this the way that I thought should be done. And I mentioned early on, I made some big decisions early on in ways that a number of the business books out there would advise against. Right. But I had very clear vision for where I thought this organization could go and the way that we should get there. And so the courage to make the big choices and there were some very scary moments along the way. I lost nights of sleep over the decisions I had to make and the ways that I'd made them, but I never met material resistance from the support I get from the top and from the people in the organization. And if I'm, in a reflective on that, I think it's, it is a reflection of the conviction I had around this philosophy of leadership and my conviction that if I did this in the right way, we would produce the results that gave me the runway to keep doing in this room. So I love that you were talking about the moments of courage, because I was thinking about, I was, I saw a video reel recently of a college student talking about being in class and a professor had a different belief system than they did. And, you know, they were like, I, you know, I don't feel comfortable, you know, standing up to that professor. And the person they were engaging with was like, well, do you have to? Right? If you don't stand up, if you can't stand up to a professor in a classroom, how are going to stand up to somebody in real life? Right? And it was like, this is the best opportunity for you to do that versus just fold and take the A, so to speak. And, because I do think there's a certain element to where as we go, I remember going through school and having people advise me both ways, right? One is just to just take the A, do what they tell you to do, spit back, regurgitate, and take the A. Then others say, because it doesn't matter which belief system you've got, that you're going have somebody that disagrees with you at some point, right? Doesn't matter what operating philosophy you have, somebody's going to disagree with you. Right? Specifically in business, there's going to be people that are going to be like, it's all about results. I don't want hear about process. You're going have people say, it's all about process. Let's not talk about the results yet. Right. And at the end of the day, you got to do both. And, and so, but the glue that holds the organization together is the culture and it's the way that we operate. And there's different cultures and different organizations and different people thrive in different cultures. Some people, they love hard knuckle, punch you in the face culture, right? They love that, that, that blood sport combat culture. And then there's other people that are like, no, I want, I want encouragement and I want enthusiasm and I want, I want us to be upbeat about it. I have, I personally have an example where I was at, the number one and number two companies in an industry and the number one, we'd walk through the halls, just crushed a quarter, but everybody looked like they had just been beaten down like that. It was it was depressing to be in the halls. It was depressing to be in meetings. People loathed coming to work. The whole nine yards crushed numbers year over year over year, quarter over quarter over quarter, and it didn't matter. Everybody felt beaten down. Go to the number two company. They're rapidly gaining on the number one company, by the way, but upbeat, enthusiastic. They hit their numbers. They crushed it. People were just excited to come to work and excited to work together. Two fundamentally different cultures, both delivering outstanding results for their shareholders. Right? One was truly gaining ground on the other. The one that was losing ground was like, no, we've got to work harder. We've got to push harder. Our results aren't good enough. We've to set harder stretch goals. We've to push people focus on what's what's wrong. We're going to hunch that they focus on what's wrong. And for me personally, that that culture was was borderline toxic for the way that I'm made. Whereas I I thrive in a trust based, encouraging culture. I don't thrive in a beat out culture. I've got dear friends that work in that company to this day, and I love them and we get along great. They thrive in that culture. Right? So I think it's important for people to know where they fit, Right. And, and how they do that. When you talk about this and leading with love, that really is unorthodox. It's highly unorthodox. Wow. So how did you get there? So let's, let's hit rewind because you're talking about delivering, you said twenty percent year over year. Yeah. Right. And you went from underperforming. And, I don't know if you were losing money, definitely flat to declining. Right? And to now you're, you're delivering outstanding year over year results, which is outstanding and amazing. How did you build this toolbox of an operating philosophy? Right? You said you developed some early on and then you were ready to be a CEO and you didn't have that opportunity where you were at. So let's, let's hit rewind and go back there. Yeah, I'm going to go way back. Okay. So I have always felt like a misfit in business. My very first job out of college, I was running a team of fifty people as a measurement and I was, it was a high stress environment and I would spend twenty minutes before work. I would show up early so I could just breathe because I was so stressed and I would go in my office, shut the door and watch Ted talks. I cannot eat lunch. My lunch hour was watching Ted talks because I had no appetite. So my very first introduction to business was a high pressure environment. And it was obviously in contrast to my constitution as a, as a, as a person. And, Harvard Business School was a wonderful place of inspiration. And, but then I went right back into a Fortune five hundred company, and it was run from a high performance perspective. It was all about the numbers, all about the stretch goals, very high bonuses for people, extremely highly paid people. But their headquarters had the turnover figures of a retail environment and this is people making a hundred thousand dollars a year. And so there's so much fear in the organization. And I internalized that fear and very early in my career, I decided to go for the A. And so I began, even though I felt torn up on the inside about the environments that I were in, I was in, and I'd, let me be clear, this was not universal. I had a number of bright spots where I worked for some amazing people and some amazing companies, but the overarching journey was one of feeling different and feeling like, this choice between profits and people was a false one. Developing a belief as I was, early in my career, I was very heavily involved after my MBA in strategy work. And so at twenty eight years old, I was leading all leadership off sites and and biweekly leadership meetings of a Fortune five hundred company, at the CBO's top team. And so I started to develop my own beliefs around how to lead. Ever since then, in fact, my whole career, I've had direct access to the CEO. So I've had a front row seat at six different industries on how companies are led. And in most of those cases, had direct access to the CEO and even the power of a pen. And so I was given the opportunity to test my theories in an influence way, but not in an authority way. And I was met with resistance along the way. People that, you know, we get, we, we behave the way we do based on the cultures that we grow up in. And I believe a lot of leaders lead with that, you know, performance at all costs philosophy because they believe that that's the right way to do it. They believe that if they don't do it that way, their board is going to judge them or they're not going to get the results and they're going to lose their job, which is why I say it takes courage to lead this way. Yeah. I felt like a misfit for most of my career. And there were half a dozen times where I seriously considered leaving corporate America for something different. And in fact, interesting note, six months after I got my Harvard MBA, I was, I was genuinely concerned that I'd made one of the biggest mistakes of my life by getting a Harvard MBA. Okay. That's something you don't hear every day. Yeah. But I have heard before. I'm now, I now believe it's one of the best decisions I made. Okay. Because, it gave me, it gave me a lot of things that probably get to it. You know, they call it a golden passport. Yeah. Yeah. It, you walk in the room with, well, you walk in the room with either credibility or no credibility, depends on who's in the room update. Cause it's a polarizing, environment or institution. But for me, it was the golden passport to direct access to the CEO's office in every single role that I've had since I graduated from there. And so I spent my career, trying to influence leaders to lead with love. This has been my operating philosophy from the very beginning. And I wanted to go to Harvard so I could have the access to the top to try to change organizations, but I didn't have the power. And at, I guess it was forty years old. Yeah, I was forty years old, two years ago when I got to the point where, as we referenced early in our conversation, I decided to stop waiting for somebody to make me a CEO and I decided to do it on my own. And, I, I took, my last day was June fifteenth of twenty twenty three. I left corporate America. I had no job on the other side and no intention of getting a job. I was very fortunate in that I had the time and financial resources take a bra. And so I spent the summer with my kids and we traveled all over the world. And, then when they went back to school, I started getting serious about what I wanted to do next. And I went through a lot of iterations of what that could look like. And I ultimately landed on buying into a franchise. And as I like to say, I MBA ed the heck out of that decision. I, looked at the franchise itself, the product market fit, the capabilities that I would need to have to operate that business at the highest level, The cashflow statements that they were providing about, you know, what the potential was for the business. So I MBA ed the heck out of it. But I think what MBAs often miss, people with MBAs often miss, especially if you have my career where, I've always had access to the top and always operated at the top of organizations. You don't have an appreciation for what it takes to get a business off the ground. And I ran headlong into the most challenging experience of my entire career. And so you think about this moment, this freedom to lead corporate America, and I've got a vision for building this business and I'm going to do it my way. And, and I got a few months in and realized that, this was not the right path for me. Faced a number of operational challenges early on. It was an industry that I wasn't familiar with, which was not new for me. Right. But stepping into an existing company in a new industry is very different from starting a business in a new industry. And for all of you listening who think that a franchise is a business in a box and the easy path to success, make sure you really understand that because it really is a startup if you're buying into a new system. And, and I wasn't built for startups. I know this about myself. I know about myself more now. And Mike, it brought me to my knees. There was a Thursday afternoon in June of last year, just eighteen months ago. And this is, you know, what a difference a year makes. Eighteen months ago, I came home from work early on a Thursday afternoon and, was shaking, physically shaking. That evolved into tears. And, I was having what you might imagine from the movies as a nervous breakdown. And I made the decision on that day that I needed to do something different. And that took a lot of courage too, because I was going to have to admit that I had failed. And if you look on LinkedIn, it says I sold a business, which is true. And I sold the business at a three hundred thousand dollars loss. Whoops. That's hurts. Yeah. Good lessons. Wish some of the best lessons. Yeah. It was cost more than my education and taught me more than my education. And. And I had to face the reality that I felt like a failure and I may look like a failure, but it wasn't in alignment with the life I wanted to live and the way that I wanted to feel. And so, and it was scary. I'm very grateful to the franchisor for the grace they showed me, but by the letter of the law, I owe them a lot of money. And, they helped me navigate that situation. And I found a buyer and was able to get out, almost exactly a year after formation of the business. And that put me in that place in October of last year of, again, I'm, I've got the resources still to not scramble to find a job, but to have discernment. And I made the phone calls and one thing led to another. And, I think it's okay to say in retrospect, I really only had one real lead when I took this role. I wasn't juggling multiple offers and very similar. I applied to one undergrad university. I applied to one business school and I was really applying to work job. Yeah. But I felt like I could really trust the system I'm stepping into and the man who would be my leader. And we had a lot of conversations I didn't trust. I also verified. We had a lot of conversations about the way that I wanted to lead and the implications of that on perhaps near term financial performance. And I knew before I took the job that I was in an environment that with the information I had at the time would nurture exactly the kind of leadership that I wanted to embody. Yeah. That's awesome. That's so good. No, it's, it's interesting, but, there were a few thoughts that came to mind as you were talking about, you know, the moment of coming home and realizing you got to change. Oh, I, I had one of those about eight, eight, eight years into my career. I was in operations and small family owned business. It was my family's business. They were highly entrepreneurial. I didn't fit. Was running plant. Was miserable. I've been there, man. Yeah. And I was like, okay. And, and we were simultaneous. I'd been part of we we'd done a startup as well. And we'd been, somewhat successful with that, getting that up and off the ground. But I was doing the strategy, marking the sales. I was doing the front end business. I love that. And so that's how I ended up making the pivot in my, my career. I was thinking about, you know, the freedom to be able to be vulnerable with each other and knowing your audience. Right. And back with, with Patrick Lencioni, when he was talking about trust and, there's a story he talks about where he was facilitating a workshop with a team and they were working on trust and everything. They're seemed like there was this one team member that was just there was a little friction there. And he said, you know, later that evening, they all went out and they, had dinner and, you know, they had some drinks or whatever. And this person got a little loosened up and they became very forthright at that point. They're like, there's no way in the world I would ever trust anybody ever. And they're like, oh, okay. So they had the next day in that workshop, he had to go meet with the CEO and say, you know, this person said this in there. If you want to have a trust based team, this person can never be on this team because this person says they will never trust any by definition. And that be something's got to change either. You're not going to operate with trust or you are, and this person's not going to be on it. And so they had held up the workshop and then had that conversation, and it was like, oh, does this get religion wrong? One of the things that I was thinking about though, is in that ability to trust and be vulnerable is, pride and shame are two sides of the same coin. You know, there's times when we're ashamed of something. But the reason we're ashamed is because we're proud. Right. And we're like, oh, I don't want to share that. It's embarrassing. Right. It's embarrassing for me to share that. The freedom comes once it's shared and once it's out there, it's released. Once it's released, there's no need to be ashamed of it. Know? And what I found to your point earlier and being able to tell some of these stories is the freedom that comes with that authenticity also allows the team to recognize that we're fallible. Right? We don't hit a thousand. Right. And when they know we don't hit a thousand as leaders, then we're also not expecting our team to hit a thousand. And that creates the freedom for them to let go of their ego, check our pride at the door. Like, I'll often tell my team, I don't care who gets the credit if we get the win. Yeah. Lover. Right? It's like, dude, who cares? Let's check our egos at the door and let's get the win. And let's get an let's have an ego as a tea. Yeah. Like, yes. Yeah. Yeah. You know? I mean, it's and Pat Lanchione talks about this as well in humble, hungry, smart, the ideal team player. Being hungry is about having ambition for not yourself, not hungry for your own advancement, but hunger for ambition with the tea. Yeah. That's so fantastic. I love that. Absolutely love that. And, you know, you were you were talking about leadership. I was thinking about one of the, most transformative experiences I ever had as a leader was when I was threatened to be fired a month into a new job. I had come from and it was amazing, it was absolutely amazing. I had come from a company that was hyper controlling. So I was a VPGM of a global business and flying all over the world. But the president that I reported into was hyper, hyper control. Even though you had levels of authority, he would say, I don't care what it says on paper. You come to me if you're going to spend over, I don't know, five thousand. Something absurd, right? I mean, really absurd. Then there were times he'd say, If you're going to spend over one thousand dollars want to know. I was like, Woah, okay. So, I switched it in this new job where I'm leading marketing and product for a multi billion dollar company. And, I've got a level of authority in that, and we're about to spend a material amount. It's literally within a thousand dollars of my level authority to spend. Right? And it's, it's material. Yeah. And so I go meet with my, my leader and I sit down with him and I walk through it, all this stuff. They're, they had already essentially gotten to this point, but they're asking me to sign off on it. And this was, you know, I was less than a month in the job, so all the pre work had been done. And so, and I, I walked him through it and I said, this is what we need to do. And he was like, okay. So do you think that's the right thing? I was like, yeah, it makes sense. I said, okay, great. I'm good with it. And I get up to walk out and I'm halfway from his desk to the door and he goes, Hey Mike, hold on real quick. He goes, what's your level of authority? And I told him, he goes, this is below that. Right? And I said, yeah. He said, if you ever come in here and ask me to sign off on something that's below your level of authority, you're fired. I love it. Yes. And I was like, I have never been more happy to be threatened to be fired in my life. I love that. I was just like he was like, either I hired you to do a job and I expect you to do it or you can't do it. You know, it's it's do the job or don't. And I was like, yes. I was kicking my heels going down the hall, called my wife. I was like, you're not gonna believe what happened. This is awesome. Right? And it was just just this freedom to fly. Yeah. Yeah, I love that. And he was like, look, I get it if you're taking a risk and you want to bounce some ideas around, but you don't need my approval for what I've already given you approval for. Yeah. You know, responding to that, I think leaders that feel the need to control are overwhelmingly operating from the place of fear. And I would encourage leaders who feel the need to control to understand what they're afraid of. Yeah. Is one thing I would say to that. If you have a leader that is over controlling, I think it's really easy to demonize them and villainize them. And I think it can be humanizing to understand what might they be afraid of. If you have a leader that feels like they need to control and you can understand if you're able to connect with them and understand what they're afraid of, you can address that directly and maybe get the freedom you're looking for. That's powerful. That's powerful. Yeah. So how does that play out? Right? Do you have an example where that's happened with you or if not, then, you know, how, how would you advise somebody that's mid management, right? And, or it doesn't matter. They can be senior management and then reporting it to, you know, CEO or reporting into the C suite. What, how do you advise somebody to, to play that out? For the, well, first I'm going speak to the top leaders. I'm very fortunate in my role and I'm, I'm fortunate and every time I've managed people that I have been either lucky to inherit really good people, or I've had the courage to change some people out. And what I look for in a team is yes, technical competency. Can you understand the job and are you capable of doing the job? But more importantly, would you make the same decisions I would make if I had the same level of information that you do? So when I put my team in place, I trust that if I had the same information that they have, I would make the same decision that they're going to make. Yep. If you don't feel that way, you need to look real hard at who you have on your team. Because they're either not aligned from a competency standpoint or they're not aligned from a value standpoint. Right. So first I would speak to leaders. If you're feeling the need to control, and if you're feeling like you don't trust your team, at, look at competency and look at values. Yeah. Because you're feeling, I would, I would argue that if you feel the need to control, you're questioning one of those two. Yeah. For the people that report to the leader who feels too controlling or micromanaging, First of all, that's not a nut you're gonna crack every time. So understand that. And if that creates high cortisol levels and stress and disruption to your personal life, whether that's the presence you show up with at home or the time you spend at work or with work, it's important to assess whether or not the person you're working for has the capacity to let go of control. If they're a good person and you do feel aligned in values, but you feel like, they're operating from a place of fear and things could be different if you could alleviate that fear. What I found is connect with them on a human level. Not everyone gives you access on a human level and that probably leads you down the first path of, is this the right place for you to be? But if you're able to connect with them on a human level, share with them about your kids, get to know know things about their kids, hobbies. I'm really migrating away from, so what do you do? To what are you passionate about? Yeah. Right? Like what gives you inspiration? And if you can understand what inspires someone, and if you can understand, look, we all come with wounding and, and life experiences that lead us to believe we need to operate in a certain way. And if you can understand why someone's behaving the way they are and what wounds they are operating from, you have data that you can use to connect with them in a different way and build trust that you wouldn't otherwise be able to build. And so, you know, it's a bit of a flow chart. If you have a manager who's controlling and they, they can't connect on a human level or choose not to, you probably have your answer. You're probably in the wrong spot. Yeah. If you had a leader who's controlling and it feels like it's coming from a place of fear or a lack of trust, either in people in general or in you, but you feel like they're a good person and you, you can connect with them on a human level. That is an opportunity, not only to create a better environment for yourself, but to help them grow as a leader. And this is something that, you know, we talk about courageous leadership on my team. I'm not just looking for people to help us make better business decisions by having healthy conflict and bringing the hard things to the surface. I'm looking for them to make me a better man and a better leader because every time, yeah, every time they bring something that is a different perspective, I come into the room with a lot of energy and it's really like, I really try to contain it and try to speak last the best I can. But I come in with a lot of energy and almost always a perspective. And the people that have the courage to challenge my perspective. Yeah. And I try to, as we talked about at the beginning, I try to create a safe space where they feel comfortable doing that, but it is the greatest gift that you can give to your leader to challenge their perspective because you will help them grow. And if you have a leader that can't take that, again, you probably have your answer. Yeah. I, there's a couple of thoughts that come to mind. One is I used to have a, like a, a work philosophy, which was love it, change it, or be with it. Which was the idea of love what you're doing. Spend more hours at work than you do doing anything else during a certain section of your life. And you should love what you're doing. If you don't love it, you should start to affect change. And if you can't affect that change, you need to be prepared to leave it. There's I've second guessed that a little bit in my as I seasoned through my career where don't be so quick to leave because some seasons just take a little bit longer. Yeah. Right? But I still somewhat stand by it because exactly what you're talking about. If you're in a toxic situation and by definition, toxic doesn't mean necessarily that it's, it's unhealthy in its own way. It just means that it's unhealthy for you. Hundred percent. Right? Yeah. Right. We're all different. That's right. And we're all unique and it's adult fit. I heard somebody once, give me incredible. I heard this saying and I loved it. It was, skills get you hired and culture gets you fired. That's so good. Right. And they, they're like so many organizations interview for skill and don't interview for culture. Well, my, that is the trajectory of my career. I, as I return to the future analogy, I got the a in every career that I had and I got the promotions, I got the money, I got the influence, but love it, change it or leave it. I rarely loved it. I was continually trying to change it because that's who I am. Like I can't, I can't sit in a situation that feels, as if it needs change and not help to drive that change. And at every juncture in my career, when I felt like I couldn't change it, I had to leave it. Yeah. Yeah. And takes a lot of courage to change and leave. Yeah. It's easy to love. Yes. It's it's hard and takes courage to try to change and and try to leave. And I I think that's when we talk about controlling bosses, it is not a character flaw. It is a conditioning. And they have been taught in their careers that I need to leave this way in order to keep myself safe. And so it all comes back to safety, Mike, like what makes you feel safe? Well, know, and it's interesting. There was a peer I had at one of the organizations that he was a president for a, know, for one of the main operating groups in the company. And we were having lunch one time and he said, Mike, your problem is you trust first. He said, I he said, I I understand you need to trust your team. He said, but you trust first and you wait and then allow them to hurt you. And he said, that's, that is hurting your career at this organization. He said in this organization, you have to be skeptical first and have to earn your trust. He said, this is not a trusting organization. And I was, that was one of the quick flags for me. It was like, okay, this is not going to be, I'm not going be here much longer. Yeah. Right. Because I do trust first and I'm not going to change that. That was something about me that at that point in my career, had come to terms with this. Like, want, I want to trust first. And I choose to trust first. And I allow people, I give them that trust. And I heard this, it's trust comes in drips and it leaves in buckets. And, and I'm, I'm okay when people violate that trust. But to that point, it leaves in buckets. It, you, you don't get it back instantly. Right? So recognizing that some organizations are not trust based organizations, that's okay. That's the way they operate. And that's great. And some of them produce incredible operating results that way in short, deliver incredible results for their shareholders. That's great. That's not a good organization for me. Right. And that's okay. Well, to be clear, I lead the same way. I just hear your mic. I dressed first and it, I mean, I am just built that way. So it doesn't feel like it takes courage for me to do that. I think it does take courage for some people to do that because trust has been violated in the past, but, I trust first and that has that has, not always worked out well for me. Yeah. But my philosophy on that is for me, I'm going to trust first. And if you violate that trust, you never get it back. Yeah. Or it's really hard. I just said leaves in buckets. But it's the way that I want to live. Yeah. I don't want to live my life looking over my shoulder. Well, and the other part of it, this is the thing where I'm okay with is we all make mistakes. Right? So like, one of the talks at when my firm engages another firm, one of the things that we have at the beginning before we ever sign statements work or MSAs or anything else is look, at some point in this relationship, we're going to get sideways. We know we I it's there's going to be conflict. It's going to happen. I don't know what it's going to be over. It could be over something obscure. It could be over something significant. Doesn't matter. There's going to be some conflict. But because we choose to lead with trust, truth, and transparency, that's the way we want to navigate through that. And, I'm yet to have found an organization that we've engaged with who didn't say, yeah, that sounds great. What we, what I have found is as we've engaged with them, when it gets pressure tested, you find out whether they do that or not and whether we do that or not. And I like to think that we consistently do that. But that's how we find out if it's a fit. If I can, Mike, there's, there's another kind of business step that I'd like to share with you that comes along those lines. So, my last large organization I was at before starting a franchise business, I was head of strategy and corporate development. So strategy, but also buying companies. And, and most of my job was leading the acquisition. Just so we're clear, corporate development is not business development, right? Mergers and acquisitions. Yeah. M and A. I'm so proud of this track record. The team that I led signed during my time there, we signed nine letters of intent or excuse me, ten letters of intent and closed on nine deals. That's insane. And we had a, and that's in a world where that number is typically below fifty percent. So we are at ninety percent where most are typically under fifty percent and our success rate in terms of what was the underwriting of the deal and what was the performance of the deal was, well, there, there were two deals that didn't go the way we want it. Okay. So, you know, you're looking at sixty five, seventy percent success rate compared to, I think publicly, static figures. It's closer to twenty five percent. That's yeah. It's, it's like a venture pulled. Yeah. So not only did we complete deals at an extraordinarily high rate, but those deals were, met the targets we set for them. And the reason I wanted to bring that up is, people are like, how did you do that? And the way we did it was one, we only, we only went for deals with people that were aligned with our values and the way we wanted to do business. And two, the very first thing that I did when I engaged in a conversation with them was to establish a vision. Yeah. What do we look like together? What are the amazing things we can do together? What can we do together that neither one of us could do alone? And then I would say, we're going to achieve this vision together. I'm certain of it. We're going get to the bench line. And it's going to be very difficult. Every deal feels like a miracle at the end of the day, and everybody is equally dissatisfied. That's it. You know, you got a good deal. And it always got hard, and we renegotiated. I mean, was a moment where the the the profit that we estimated for the business we were buying, due diligence was cut in half. We still got that deal done. And I'll note that was our number one customer at the time that we were looking to buy. So the stakes were very high and we told them the business was half of what they thought it was worth. Oh. That's hard time. Got it done. And by the way, we structured the deal in a way that through an earn out, an equity stake in the larger company, they got more money at the end of the day than they thought they needed when we had their EBITDA twice the number. So having that vision and acknowledging upfront that we are going to have rocky times. And I think this applies not just in business, but in relationships in your life. Having the vision and understanding there will be rocky times and holding that vision when the hard times come is, is the key to everything. And that applies to employee employer relationships. Yeah. I mean virtually every relationship. Sales life. A hundred percent. And I'll note, fun fact, the one deal out of ten that we didn't get the deal done on, was the acquisition of a relatively small company that was brand new. They were growing rapidly, and so the numbers were moving quickly. And, the number we gave them at the beginning didn't hold up in diligence just because of timing and dropping one month from last year and adding one from this year, And it was the right decision for them to go in a different direction. But because we established the trust and the vision together, one of the principles of that agency is now my VP of sales. That's insane. That's awesome. Yeah. So the one deal we didn't blue or one deal we didn't win Yeah. Was maybe the best deal of my entire life because I got Steve. I love that. I love that. Well, man, Robbie, thank you so much. I really appreciate it. Is there anything that we haven't talked about that you want to talk about? I don't think so, Mike. You covered a lot of ground today. Yeah. This was, an incredible discussion. I appreciate your curiosity and taking the time to let me share a little bit about myself. I love this, man. Thank you very much. If people want to get in touch with you, what's the best way? Wow. That's a good question. And we'll put it in the show notes as well. Yeah. Well, you can reach out to me on LinkedIn and kind of have an open profile there. Is that Robbie Humble? It is Robbie Humble. Okay. It may actually be Rob Humble in some spaces. I don't know if LinkedIn changed my my URL link because I used to go by Rob. That's only the story. But Robbie Humble, if you search on LinkedIn, you can find me or shoot me an in message there. Yeah. I won't share my email too broadly. Okay. Just because I'm not gonna go there on on a podcast just yet. Yep. But you can find me on LinkedIn. Perfect. And if you if if this is compelling and inspiring, I'm looking to connect with like minded leaders and not only learn from them, but to support them in their growth. So, please reach out. Yeah. Cause I, I can imagine some folks would want to beat some ideas up. Yeah. I'm here for it. I, I learned everything I shared today the hard way. And if I can help others short circuit that process and get to the answers faster, I'm all about that. Thank you. Yeah. It's awesome. Hey. Thanks so much for being with us today. Huge shout out to Robbie for just being authentic and sharing the way that he's led and the lessons that he's learned. If there's anything else that I could take from this, it's it's the willing willingness to be able to be authentic and lead with love, and the power of leading with love. So, thanks so much, and join us next time.

About the author

MM
Mike McCalleyFractional Chief Growth Officer & Consultant

Mike is a leading marketer with expertise ranging from start up ventures to fortune 50 companies. With a passion for B2B and community building, Mike has evolved how traditional companies go to market and truly educate, inform, and inspire their community. When Mike isn't building out media and strategy plans for companies you can find him announcing his local high school football games and spending time with his family in Plano, TX.

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About the Experts

MM
Mike McCalley

Host, Get Vertical! with Mike McCalley

Mike McCalley is the host of Get Vertical!, a podcast focused on growth stories and lessons from industry leaders in the Pro AV and adjacent sectors. He brings experience as a senior executive and advisor to his interviews with CEOs and business leaders. McCalley uses the show to explore leadership, business transformation, and career development themes.

RH
Robby Humble

Chief Executive Officer

Penn Warranty / Preferred Warranties

Robby Humble is a CEO and investor with leadership experience spanning seven industries and every major go-to-market model, including B2B, B2C, B2G, and D2C. He has held C-level roles in public and private equity–backed companies, helped lead a $720 million company sale, and driven a 40%+ EBITDA CAGR through an eight-acquisition roll-up strategy. He is currently leading a multi-year transformation at Penn Warranty and Preferred Warranties and is the author of the forthcoming book Love & Leadership.