Adam Joseph, entrepreneur, 5-time PE-funded CEO, two-time Fortune 100 executive, and Summit OS Guide™, shares how developing people through ownership, mentorship, and trust drives leadership growth and organizational success.

We explore Adam’s journey from first-time founder to leading multiple private equity–backed companies, and how his Leadership Growth Framework—Identify Talent, Launch Careers, Mentor, and Allow Them Room to Fail—has helped him build empowered, high-performing teams. Adam explains why potential matters more than experience, why CEOs must coach forward instead of managing backward, and how giving people space to fail builds resilience and confidence.

He also discusses the “Burn the Boats” mindset—what it means to go all in as a leader—and shares how to balance ambition with purpose, family, and fulfillment.

Good day. Dear listeners. Steve Preda here with the Management Blueprint podcast, and my guest today is Adam Joseph, who’s an entrepreneur, a five time private equity funded CEO. A two time Fortune 100 executive and the Summit OS Guide. Adam, welcome to the show, 

Steve. Thank you. It’s been a long wait. I’m thrilled to be a part of blueprint.

It’s good to have you here on the show and, you know, let’s dig in. I always ask guests about their personal why and how they manifest it in their professional life, in their business, in the practice. So what is yours? 

So, I know this sounds cliche, but you know me a little bit, so I think you can validate that. I really try to live life to its fullest when it comes to my career. I love to fill my days with people that share my passion for building. When I come home, I wanna be with people I love, and when I have time off, I want to enjoy the adrenaline sports that give me energy, whether it’s skiing or biking or hiking. Or climbing, whether it’s with other experts or newcomers who wanna learn. For me, that’s what energizes me. And I have found in my career that it’s possible to do this in business as well. I can remember as a young entrepreneur, building my first company, trying to get my very small team to be as productive as possible and to work as hard as possible. And part of the magic with that was to get the most out of them. I bought two cheap hockey goals at a Costco, and every day at lunch we play a little roller blade hockey. Not only did it make them more fit, but they, we really got to know one another and, and enjoy one another aside from sling and code. And I, not only rewarded them with a little bit of fitness, but we were fortunate to get a trade sale just a few years later. 

Wow. 

I truly believe in all things you need to savor the journey, not grind to the finish line. It’s true in a bike race, it’s true over dinner, and it’s certainly true with a business.

Yeah, I like to say also that it’s so hard to make a business successful if you don’t at least enjoy the ride and you don’t have fun along the way. 

Absolutely. I mean, and there was absolutely times in my business career where it was nearly impossible for me to come up with that right balance and it impacted my family, it impacted my personal wellbeing. I would argue that many of the management skills I developed as an operator were so that I could make the time to recover that balance between work and everything else. 

So what does it take to create the time? What does it take to have this balanced life as a top executive? It’s not something that CEOs brag about, that they are having balanced lives.

Well. A lot of it is being part of or building a great team.

To me, the best thing you can do is have people that you know and trust, that you can not only delegate things to, but know that they'll be done as well or better than you can.
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So what does it take to be at a team, such a team around you? How, how do you attract these people? 

Great question. So important and rewarding. One of the things I’m most proud of in my career, you know, are some of the people that I brought along the way and certainly appreciate others doing the same for me,

the first piece, and again, this is one of the parts I also really enjoy, is identifying talent.
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Sorry Adam. So how do you know who has potential? How does it show up? 

So some of it is just, you know, understanding what drives them, understand how they interact with you, how they interact with others that, you know, get, oftentimes you’re finding out about them because of a reputation, because of something they’ve done. Peel under the covers, understand, you know, where they want to go with this, how they got these skills, et cetera, and so forth. And in many cases, it’s giving them a test drive, taking people that have never managed anyone in their lives and saying, today you’re not gonna manage people. You’re gonna manage a project, a blueprint, what have you. And maybe that becomes a business and you get to read it or lead it, or maybe it doesn’t. That the main thing to me, whether you’re developing a leader or an individual contributor, is work with them on an idea that they can own with plenty of wiggle room for them to grow and innovate within that idea, right?

The concept of a business within a business or an entrepreneur, working for an entrepreneur makes absolute sense and really gets you to exploit the best of that person, the things that they're passionate about.
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I like what you said about ownership. You  mentioned, you used the word ownership. You’re looking for people who are willing to own their function. What do you mean exactly by owning their function? 

Owning their function. So again, it begins with you as their leader, giving them lots of rope saying, we have a problem. Right? We’re trying to, I can look at my, think back to my experience with Dan Grom at Concur. Dan was a star collections manager at Concur. He was collecting millions of dollars from some stingy CFOs who didn’t want to pay us. He came to me and said, I want to be part of your customer success organization. I wanna touch customers on the positive side not take their money after they’re already onboarded. So we came up with some ideas on things he could help me with on a fledgling business that was auditing customer expense reports. I said, Dan, figure out a way to do this less expensively and more effectively than we do today. It took months and months just to come up with the scheme, eventually resulting in us creating a thousand person global operation that Dan, who managed, you know, five collection agents when he joined me, was overseeing and generating over a hundred million in revenue. We applied his ability to connect with people. The idea that we could automate a service that we were previously doing with people to create a business that represented roughly 10% of our company’s revenue before we sold it. 

Okay. So, that’s ownership. He had an idea and you let him run with it. And he created a business within the business, kind of an entrepreneur type of situation. So, when you identify the talent, what’s the next step? What do you need to do with the talent that you identified? You give them ownership. What’s the next step? 

Oftentimes, when, before giving them ownership, getting them hired means really enticing them, right? And leveraging, you know, their own entrepreneurial spirit. For me, as a grower, right, and someone who’s building businesses, having someone with that passion is important and convincing them. That joining our team, being part of a, a bigger function and taking on a meaningful role is something they really wanna do. You know, once I bring them on board, once we give them that challenge, it certainly requires a great deal of investment in them. Training, mentoring, et cetera and so forth. You know, when it comes to mentoring, my guidance is really think about coaching people forwards, not backwards. Spending a lot of time on the things they should, or could or would’ve done isn’t gonna help them scale, you know, instead provide a framework that allows them to make mistakes. I mean, let’s face it, we’re not surgeons or nuclear scientists. So if a mistake is made, no one’s going to die. But oftentimes,

that leader or potential leader learns more from making that mistake and getting collective feedback on how they could have handled it differently than watching someone else do it or telling them how to do it.
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Yeah, yeah. Just an aside, so I just got off the call with a client. And he told me that he was very frustrated because one of his team members made a $50,000 mistake. And I said, okay, and what did you do? He said, the first thing I did was I called that person and I told her that her job is safe. This is not gonna count against her, and we are going to figure out how to solve this. And just don’t panic. Do your job and you’ll figure this out. So I think this is super important. Even Jack Welch tells a story when he blew up a factory and then he got a promotion afterwards. 

No, I think that’s great. All right. As an entrepreneur, you gotta be in it for the long haul. Right? And bumps will happen, mistakes will be made, and great ideas will evolve over time. But having people with the spirit and the confidence that you’re invested in them just as they’re invested in you and the business is critical. And by the way, just because you’re giving them a lot of rope doesn’t mean that mentoring, you know, in the form of informal conversations and feedback is super important. I strongly suggest having those conversations, if not monthly, then quarterly with your highest potential people. Keep it human, keep it informal questions like, ‘Hey, what’s working great’, ‘What would you have handled differently next time?’, ‘How can I better support you?’, those are all amazing conversation starters, right? You don’t have to end there, but start there and you’re having a conversation as peers and you’re learning. What they’re learning and helping them evolve.

Yeah, that’s great. When you actually help the person grow and they feel that you have their best interest at heart and you’re doing it not just for the business, but because it’s the right thing to do for them, that creates tremendous loyalty in my experience. 

And it’s better for the business. Right. You know, it just goes along with, you know, when there’s an opportunity to highlight. Those people share the spotlight. Get right, give them the win. Think about their next career step in the business, even if it may not be with you. My best leaders were always promoting their people, not just within their own function, but talking about to their peers and saying, this person really deserves to be a manager. This person would really develop great if they could do a stint in Europe, whatever it might be. We’re all in it for the long haul, and I view leadership development not as a nice to have, but, but really one of the highest responsibilities as a leader and truly your company’s growth, your profitability, your exit value depends on, on developing people.

I mean, it’s all about the people that run the business for you. So we talked about identifying talent. We talk about empowering them, having them own their function, and then mentoring them, help them become entrepreneurs and, you know, allow them to make mistakes. Obviously, they, you want, don’t want them to make mistakes. They don’t want to make mistakes. You’re willing to grant them the right to take some risks. Reasonable risks that can have a positive outcome and help them grow and learn what else is needed to grow your people. Anything else that you do or, or you have done over your–. 

I mean, those are certainly the primary ones, a lot of it as we’ve talked in past is also creating that framework for success. Things that they can apply to their teams, right? It’s great when you see a smooth running senior leadership team, but after all, everyone in the room has been doing that job for, in some cases, decades. Figuring out how to push it down to the next level. Give them tools, give them examples, give them processes and playbooks that they can use with their teams. And oftentimes they may come back and say, ‘Hey, the playbook that we use up here doesn’t work down there’, so this is what we’re going to do differently. But providing proven tools and being available not just to them, but being available to do the skip levels,

to learn from their team, what we may not be doing right in the boardroom, is super important to support those various parts of the business and set those leaders up to be part of your succession plan.
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Yeah. And, this is a great segue because I’d like to ask you, you know, having gone and exited five companies as a private equity funded, CEO working for Fortune 100 companies and executive. As an executive, I mean, why don’t you just keep doing what you’re doing and what made you decide to become a Summit OS Guide and help other businesses as a guide climb the mountain, so to say.

I certainly loved what I did for, well over 30 years, as an entrepreneurial CEO and operator. I still love working with high energy people who truly wanna build businesses. But honestly, after being hands-on and neck deep for that long, I decided now was an opportunity for me to pay it forward as a professional leadership guide, it gives me a chance to apply my expertise using a framework you might have heard of called Summit OS to continue my work as a coach instead of a team captain.

So what is it that most excites you about being a coach rather than working and, and running the business? After all, it’s the CEO who has all the power, right? The coach can only lead people, they can help them see things that they don’t see themselves, but ultimately, you’re not gonna make the decisions and the power is vested to the CEO.

But I love working with those CEOs, right? Even in my own businesses. Working with a line of business leaders, right? They’re the ones with the passion, they’re the ones with the vision. I’m helping them identify blind spots. I’m helping them empower their team and get more from their organization. I get to be in the meetings when they’re making some very critical decisions or really thinking about how they accelerate growth, how they apply their profits to expanding their business, et cetera, and so forth. But at the end of the day, I get to go home and see my family, and they get to spend the night doing email they couldn’t do during our meeting. And preparing to, then execute on this grand plan that I got to have some small part of. 

Yeah, I totally relate to this idea that you want to work with passionate people. You know, I find the same, that when I work with a passionate entrepreneur and I spend eight hours in the room with them in heated discussions and, you know, solving difficult problems on my feet. And when I leave, I feel energized. I feel I have more energy leaving the room than what I walked into because this passion that they have is so contagious.

Right. Well, no, absolutely, and I’m certainly, there’s days where I want to, you know, come back the next day and, you know, figure out what I can do to help. But honestly,

I believe at this stage in my career, I'm more valuable providing the tools and helping to tune the operating system of the company and allow people who created that idea,
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Yeah. And, and the CEO, you know, as you said, they have to go back and still do their days, work often after the session, and, and they really, have to go the extra mile, and make tough decisions. What was the hardest decision that you had to make in your career? 

I’d say I’m not proud to say that I had to do this more than once, but I think the hardest decisions are doing company restructurings. Good people, unfortunately, lose their jobs, even if the drivers are, things like investor issues, or product slips or a global pandemic, it’s always gut wrenching and at some level it’s your fault. 

How do you get over this and how do you process it as a CEO, especially when you feel like it’s your fault or partially your fault, maybe you could have done something that you didn’t realize at the time or, and then you have to make the decision and then you have to break the news. How do you process it? How do you move on? 

Well, you know, to begin with,

regardless of whose responsibility it is. It's your responsibility to be professional in managing the changes, determining what is necessary for the longevity of the company, making sure the team is treating the departing talent with respect,
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Yeah, I think there is momentum in businesses is super important, and when you feel like you have momentum, then maybe you are going to keep the stuff on longer because you feel like the momentum is going to carry you through the difficult patch. And often it does, right? And then by the time you are willing to put the plug, it’s already too late to some extent. And then you have to make a deeper cut. And I don’t know if that can be alleviated entirely. 

Yeah, no, it’s hard, right? I mean, certainly, you know, in companies where you have a, a direct sales organization for example, and at the end of the day the number of feet on the street, you know, directly correlates to how quickly you can grow. And it’s easy to be mesmerized and say, we need to put people in every NSL city not realizing that, that some markets for some products are going to be stronger. You find that all of a sudden. Putting offices in secondary cities or setting people up that don’t have the resources they need from headquarters or regional experts makes it that much harder for them to get productive. So you’ve made this very significant investment in an organization, in a team that’s not even been given a chance to prove themselves before you say, ‘Hey, you know what? We’re gonna shrink the sales organization and count on the people that are already performing for us.’ 

Yeah, it does happen. And sometimes it’s a board level decision. Maybe there’s a merger that happens or the board gets jittery and  they are going to mandate a change that is counter to your vision. And,  sometimes this, a CEO, a heightened CEO will have to, you know, execute. 

Right. No, it’s a painful process. I will say I learned from every one of those, right. And I bled along the way. Then you find yourself in another situation, or in our current world, right, in the role where you know you are coaching an organization and saying, you know, for whatever reason it appears that you’re really overweighted in this department and you need to figure out how you can do more with less.

Yeah, absolutely. So what is the most important question that any entrepreneur should ask themselves on a regular basis in your opinion? 

So to me, and, and first and foremost, you gotta do it day one, right? Before you tie other people’s lives to your vision. It’s, you know, are you ready to burn the boats? Right? And not just necessarily for the idea, that first idea you had, that was the spark that motivated you to quit your job and start your own company. But are you so committed to being an entrepreneur in this segment, leveraging your knowledge and passion that you are going to bet everything to turn it into a success, which not only has financial implications about lifestyle implications and you know, certainly is going to be all encompassing as you build that team. ’cause you know, you start out with a team of one and a business plan and your bank account. So unless you’re truly committed to doing those things and then making sure your significant others support you, then you may fail before you start. If you have that passion and you can’t let it go and you’re willing to, to play the long game, it’s a wonderful experience and, and so rewarding, but absolutely not for the faint heart. 

So why is it important to burn the boats? 

I think if you’re half in, you can’t get there unless you’ve invented some new industry with no competition. There’s someone else who’s staying up later and working harder, I’m not sure. And in the entrepreneurial world, smarter helps, but smarter doesn’t usually get it done. It’s passion and hard work and strategy and execution that get it done. And I think if you’re already thinking of your plan B. Or where you’re going to get a job to rebuild the piggy bank, then you’re not ready to start off as an entrepreneur. We’re a strange breed, but yeah, you need to make sure you’re one of us before you take on the risks and, and the pressures of building a business. Even you have, having done it multiple times, every time I look back and say, wow, that was a lot harder than I thought it would be, with a lot more mistakes than I intended, and it took a lot longer than I thought.

It takes twice as long and costs twice as much or more. I relate to that. So who are the ideal clients for you that you can really help climb that mountain? What kind of businesses do you love to work with the most? 

Based on my experience, I love SaaS businesses, so I’ve spent my career in enterprise software. Nearly all enterprise software is now software as a service. So that’s an area where I have a lot of passion and experience, I think. Being tested by your customers every day, having to deliver in order to collect that recurring revenue stream is also something that I thrive in. I’ve worked in a number of different segments. I certainly have enjoyed being an early innovator in the cybersecurity world. Even more recently in the physical security world. I had some great experiences in the financial technology world that just continues to scale and scale. I look at the way we did expense reports at Concur, and it seems so antiquated now that people are basically being given a third party credit card, and all they do is spend their money and it allocates and reimburses them in real time. But for me, it’s really tech enabled services and enterprise software that is my core.

But honestly, I’ve worked with a number of companies, well outside my domain space, and have come to discover that growth stage companies are independent of the product, whether they’re selling an individual skillset or a hard good or a service, the challenges we face, right? You know, with people, with the performance of the organization, with how we measure against our competition and benchmark what’s possible. And then in turn, ideally, and sometimes it takes a while, turn that into profits that then power new investments for the company. And expansion is surprising how similar businesses that I thought I knew nothing about. Once peeling under the covers  and talking to the leaders and saying, these are the problems I’m facing. Might say, well, yeah, I’ve been there and I’ve been there and I’ve been there. And let’s, you know, talk about  your alternatives. Oftentimes they have the vision and they have the answers.

It's just having the conversation of how we put them in order and work with the broader management team to execute against them.
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Okay, so if someone from our audience would like to learn more and, and connect with you and maybe have a conversation about their business, where can they find you? 

Well certainly they can find me on LinkedIn. They can go to ACJ Advisors, my website. And there’s also a wealth of information on the Summit OS CEO website. Not just coaches like myself, but there’s always fresh information on the site that you might find interesting as an entrepreneur. 

Awesome. Well, Adam Joseph, entrepreneur and five time CEO of private 200 businesses, twice Fortune 100 executive. So been in the trenches and now helping other small to medium sized businesses scale. Thanks for coming on the show and sharing your experience and wisdom, and those of you who enjoy this conversation, stay tuned because every week I bring another seasoned entrepreneur or CEO to discuss their framework that they came up with on the show. So thanks for coming, Adam, and thank you for listening.