What does it take to move from entrepreneur to trusted advisor, and to help hundreds of CEOs scale with purpose?
In this episode of The Strategic Business Influencer, I sat down with David Chavez, founder and CEO of Assured Strategy – Business Strategy Coaching Firm, serial entrepreneur, and Scaling Up coach. A military veteran, former CPA, and seasoned operator, David has helped over 280 businesses navigate growth, exits, and transformation. His journey spans taking five companies public during his time at Arthur Andersen, building and selling his own CPA firm, and now guiding leaders through high-stakes decisions with practical, battle-tested advice.
David shares:
– How the Army instilled the discipline and leadership training that shaped his career
– Why real growth often comes from learning what not to do—and being willing to let go of control
– The mindset shift required to scale from founder to CEO
– Why humility is non-negotiable for leaders who want to grow
– His definition of freedom—and what it takes for leaders to actually find it
David’s story is a reminder that frameworks and strategy matter, but experience, and the willingness to learn from mistakes, is what truly builds credibility. Below is the full transcript of our conversation!
Want to learn more about David and the incredible work his team is doing? Visit AssuredStrategy.com.
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Paige: Hi everyone, and welcome to the Strategic Business Influencer, my new series for leaders who know that in today’s evolving world, trust is the greatest competitive advantage. Today’s guest is David Chavez, founder and CEO of Assured Strategy, serial entrepreneur and trusted advisor to hundreds of CEOs across the world.
David is also a military veteran, a former CPA, and a certified Scaling Up coach. With more than a decade of experience helping companies grow with strategy, structure and alignment. He has led successful exits, scaled his own companies, and coached over 280 businesses through significant transactions. His approach is practical, battle tested, and rooted in real world experience from taking five companies public during his time at Arthur Anderson to building and selling his own CPA firm.
Now through Assured Strategy, he helps leaders align their teams, sharpen their execution and drive real, measurable growth. The reason I’m so excited to have David on is he’s so unique because it’s not a just about the frameworks of David. He has been in the trenches himself as a seasoned entrepreneur, and his advice comes from real experience, not just theory.
So I’m excited to welcome David to the series. So grateful to have you on.
David: Thank you. I thinking that has to be the best introduction anybody’s ever made. That was fantastic.
Paige: Well, you have an impress – Well, you have such an impressive story and journey.
David: I sound amazing.
Paige: So excited. Well, you are, you are. Thank you.
I’m excited to, to dive into, you know, the, your story and just your experience because you’ve worn a lot of hats, you know, from. Military veteran to CPA to serial entrepreneur, and now advising hundreds of CEOs. I wanna start though, at the beginning of your journey. So what part do you feel of your story has shaped really how you lead today?
David: You know, it’s interesting you asked that question because, because in my childhood I did not have a lot of discipline all throughout my childhood with the way I was raised. And so I would say that the Army really helped me get the discipline. And then also I know contrary to to the public’s belief, the army is.
Great at training leaders, and that’s, I, I, I think I received a lot of really amazing training. Being in the army on leadership, how to deal with people and how to, how to improve myself. Then I went on to Arthur Anderson after I finished college a after the Army, and I learned quite a bit there. So I also learned what not to do.
I remember somebody telling me once to keep my back against the wall and I would do just fine there. It was, it was an interesting time. I think that was the time that the world was starting to shift a little bit and people were starting to understand leadership at a higher level. I didn’t have that everywhere I went in Arthur Anderson, but I definitely saw that, that old style still there.
So it taught me, probably I don’t wanna do, and then what I wanna do with the great leaders that I had there. I, I had some amazing leaders also. So I, I couldn’t say that it was just one way. And then of course I think running my own businesses and learning from doing things wrong is really where I learned quite a bit.
I hate to say that, but I probably have botched leadership several times in my journey and taught, it’s taught me some valuable lessons. It could be with losing somebody that’s really important to the organization. It could be with objectives not being met, things like that. So. I, I would say Scaling Up just had a lot of influence on me too, and then some of the speakers and books I’ve read over time really had a lot of influence and that that has contributed a lot to Scaling Up.
Paige: Mm. I love how you talked about, you know, learning what not to do and learning from mistakes because, you know, there’s that, you know, phrase fail fast and, and you keep moving forward. I think that’s, that’s so crucial and what I love about what you do now, David, is you’re one of the only coaches I know that has built and exited your own companies before, and so I’m curious what has made you decide to take everything you’ve learned?
You know, the, the good and the bad and turn it into a mission to help other CEOs scale and succeed.
David: Oh, what a great question. So, I, I don’t know if that was my intent originally to do this long term, literally I sold my CPA firm and when I sold my CPA firm, I knew I wanted an or start a consulting firm.
I didn’t really know what I was gonna be consulting on. I, up to that time, I had done a lot of valuation work. I had I’ve done over a hundred deals buying and selling companies. I had done, you know, I did IPOs, things like that. And so I I wasn’t really sure what I wanted to consult on though. And after taking a year off, after I sold my CPA firm.
I got online to just get a one page strategic plan that’s Scaling Up offers and they were looking for coaches and literally at that time I didn’t even know what a coach was and I was pretty heavy in the consulting world. So coaches were just really starting to come online at that time. And they were looking for a coach.
So I started investigating it and I threw in my hat in the ring and they asked me to come into Scaling Up. And I’ve been there for 16 years now. I’ve I, we licensed their products, so we have our own company, but at the same time they’ve, they’ve had a lot to do with that. And then, and then I just ended up loving it.
I mean, once you start to be successful at doing this and you have, your clients really have. Huge jumps in their business, then it really starts to motivate you. And I just think my experience with valuation and financial, my financial acumen, like from Arthur Anderson and the time thereafter, and my own CPA firm, all that I’ve learned.
Really comes into play with helping people. So it is some of the transactions I’ve done myself and the challenges that went with that. But it’s also helping a lot of other people do it from the financial side and then now from more of the strategic growth side. So you, you, you just get a lot of that experience.
I think that comes along the way so.
Paige: Hopefully that answers question. And you how, yes. And I’m sure you know too, somewhat how they might be feeling at certain points of their growth just because of your, your own experience as well.
David: Yeah, and I think, I think sometimes, you know, even the clients. May feel I’m judging them and I have to remind them I’m not judging them.
You know, I, I have my own stuff and I’ve probably made all these mistakes, every one of the mistakes they’re making, I’ve made in my own time. I’m just trying to help them see it as fast as I can, and sometimes that, that’s not easy to do.
Paige: Yeah. And as a, as a coach of a CEO, like you were saying, you have to have.
That high trust, especially when you’re in, you know, high stakes moments of their company. So I’m curious, how do you go about building that credibility and connection with these leaders who are used to, you know, having all the answers themselves? I’m sure that’s really challenging as you walk into a room like that.
David: Yeah, I, I, I think that I’ve learned that a, a potential client really has to have humility. And if the client doesn’t have humility, and sometimes it’s not easy to see, you have to ask some questions that they may not even realize you’re asking. And the way they answer ’em, you can sort of figure out whether they have humility or not.
’cause some people come off a little arrogant when they’re really, they’re not. Right. Really that confidence is something they need to scale their company. And as an entrepreneur, getting a company off the ground, you have to have a lot of self-belief. Right. And, and it’s a fine line to where that turns into ego versus humility.
And so, mm-hmm. Yeah. Sometimes it gets a little cloudy in there, but I think I, I. I try to ask them hard questions and really challenge their beliefs with my heart, not judgment. And so I think people feel that when they’re working with me. Like I would probably say that most of my clients would say, man, he is hardcore.
Very frustrating sometimes, but he holds you accountable and he gets you outta your safe space so you can actually make the advances that you really wanna make. And he does it in a way where it feels like feels like he’s pushing a little too hard, but at the same time, you can tell he cares about what’s happening.
So that’s, that’s the general feedback I’ve received from my clients about my, my approach. But they wouldn’t say it was easy.
Paige: Sure. Sure. And I do think it takes so much talent to be able to, to come in a room and, and do that with somebody and take so much psychological safety that you have to build with them as well.
You know, I, I know that you mentioned earlier you discovered Scaling Up after using it to scale your own firm, and so I’m curious, what was it about that model that clicked for you and why do you believe that Scaling Up is the best model out there?
David: Uh, what, I’ll start off with my story first. My business had really just stopped growing for five years.
My CPA firm grew super fast. I mean, it was just on this this really high trajectory. I think the last year before it really stopped growing. It only grew like about 5%, the fifth, sixth. In the sixth year that I had it, and after the first five years, I don’t think I had a year lower than a hundred percent growth and Wow.
And, and it was, it was crazy. At first it had like 700, 900%. Wow. So it, it was just crazy, crazy growth. And then it just stopped and I couldn’t figure out what was going on. I read the book, mastering the Rockefeller Habits, that’s where Scaling Up mm-hmm. First was introduced and, I started to realize that I’m a control freak and that I’m stopping my company from growing.
And it’s really interesting because as an entrepreneur you sort of have to be a control freak when you’re starting the company, but as you’re starting to scale it, you need to let some of that go and you need to plan it out. And what Scaling Up did is it really got me focused on planning out my strategy.
I think there’s a lot of other systems out there that focus on execution. Execution is important. And I’m not saying Scaling Up doesn’t provide that, but it, its focus is getting the strategy down, then executing with excellence, not the other way around. And so I would say that a lot of people come to us from other systems once they hit about 20 million.
I’d say probably in between 10 and 20 million. We pick up quite a few from other systems that say. You know, it’s just not working anymore. And that’s because it’s not connected to a strategy in the company. So that’s where it really I, I, I think the difference between Scaling Up, I think it’s really strategically focused.
It does have a lot of focus on people who, who’s the right people on the bus the old cliche term. Mm-hmm. And then also executing with excellence and building cash flow. So, so that you can do the initiatives you want to do as you grow.
Paige: Yeah. And I think you made such a great point. It, it’s hard sometimes to transition from that founder to CEO as you scale the business.
You know, I’m curious, what type of mindset shift do you feel like needs to happen to start letting go of that control and putting other people in the right seats to lead some of those parts of the business?
David: Yeah, I would say a mirror, right? Mm-hmm. And just hold the mirror up to the client and let them see what’s happening.
I think you know, 85% of our behaviors in our subconscious mind, and we really have no control. And I think what you’re trying to do is get people consciousness so they can actually see what’s going on and that’s not always easy. And it’s not gonna happen in one setting. I, I it’s really interesting.
I was with a client last week and we’ve been together for almost a year now. And I told them the retreat before last, dude, this was the last retreat that we have scheduled in this agreement, but we’re gonna continue on. But in the last retreat, the one before that, I actually told them I was lying to them about some things because if I, if I shared everything right out of the gate.
It would overwhelm them to the point of shutting them down. So I have to balance how much you tell them at and what timing that’s going to be. And so, I think that that’s, that’s one of the challenges I, I see a lot. But the other one, the big one I really see is on leadership teams. There’s people on the team that don’t belong there.
Mm-hmm. Usually what we do is then when we’re a smaller company, we promote somebody. And they become valuable asset to us and not diminishing what they’ve even done up to that point. They’re just not the person that’s gonna take you to the next level. And it’s really hard to deal with that. And how I usually say it to when I’m talking to executives is because.
These people have been to dinner at my house. They know my kids, I know their kids. I know their spouse. I know, you know, they know my life. I know theirs. And, and we become connected through all the challenges that we have overcome. And so the connection you have with that person is so close and it’s really hard to, ha.
When you start to see that that person’s not gonna be the one to help you carry to the next level and have to deal with that and have that hard conversation with them. Right? But I would also say don’t throw that person away. We gotta find the right position in the company for them, because you obviously believe the same values and things like that.
So. It just, you know, that’s probably the biggest issue I run into because I’ve seen a lot of really great companies out there and worked with a lot of ’em, and they won’t switch a leadership team, so they never get what they really wanna get, so they just won’t do it.
Paige: Yeah. And I. Yeah. And I’m sure that’s a, a constant blind spot that you’re having to point out for them that, that they’re not seeing themselves, which is so hard.
Yeah. I, I wanna sp, I wanna look at, you know, some of your time, especially with your CPA firms, so. Once you had your exit, that would be the point that a lot of entrepreneurs would say, Hey, this is the finish line. This was the end goal. But I’m, I’m curious for you, during that transaction, is there anything that you wish you would’ve done differently?
David: Oh that’s a loaded question. It’s probably about,
Paige: I know this might take us a full hour.
David: Yeah, yeah. I, I have to go to my therapist after I’m done. So, so, i, I, I would say I, I made a couple of really big mistakes that I knew that I should have not made. So, so it was, I, I had already been helping people with exiting and buying new companies, and I don’t think I had a goal when I would, when I was selling my firm, I didn’t reset selling the firm was the milestone.
And then when I sold it, I didn’t realize how depressed I was actually gonna become. So, and I think I really became depressed because I really didn’t have an, the next objective. I actually thought I was going to retire. Like you were insinuating, right? I literally thought I was. But. Golfing every day for a year was not fun.
In the end. And I just missed the excitement and that’s why I got back in. And I don’t think I’ll ever retire now that I think my opinion’s totally changed of it. And I think I just love the challenges and it keeps my brain active. Keeps me active with all the challenges and everything that I’m trying to help people through, and then even scaling my own company to challenges right now.
Paige: Yeah, and I love that you jumped into just an entirely, you know, new industry with a shirt strategy as well. It’s a, it’s a whole new challenge, I’m sure, and a whole new type of business to, to scale for you, which is really interesting as well. One of the things that I know you talk about is helping leaders find their freedom.
And so I’m curious, what does freedom mean to you as a founder and coach?
David: Yeah. Our, our, our purpose in our company, our mission statement, if you will, is guiding leaders through change to find their freedom. And one of the things I say to the coaches that if you’re not interested in doing that, please leave because you won’t be helping us.
And I, I think that. Freedom, really in our purpose is not for me to define, but that’s for each individual. But I say what’s freedom to me is being able to spend time really growing my company and really understanding my customer’s needs. I think that that’s really fun and trying to come up with new ways of solving, helping them solve their issues is really fun.
And, I just, I, I, I say that from the freedom standpoint is being able to spend time doing that and not let the operations of the company rule all my time. Right? Sure. So, I, I love
Paige: that it’s really.
David: Yeah, it’s really being able to go out and, and, and you know, the real problem is, is like when we’re small, we’re very close to the customer.
We’re talking to ’em of their day. As you start to scale, you get further away from those customers, but you still act like, you know, and that’s the big mistake a lot of entrepreneurs make. You’re not close to that customer anymore, and so that distance from the customer, I have to go down and spend time there, and that’s what freedom is to me.
To be able to go down there and spend time there and listen and really come up with new ideas and new products we could offer. Things like that.
Paige: Yeah. And, and what do you think it takes for a CEO to actually get to that freedom that they’ve defined for themselves?
David: Well, I think it’s you have to get out of all the things you’re doing now, really.
Mm-hmm. A lot of us when we start companies, and I think you probably experience the same thing. We’re in the doing, I’m still in the doing probably half of my time. I would tell you that I was probably at 90% three years ago, so I’ve come down quite a bit, but I probably need to get down to about 20 to 25% of my time, spending time with clients.
And then the rest of the time spending thinking and then going out and visiting all the clients and there’s finding out what their real needs are so I could help satisfy those needs that they have.
Paige: Yeah. I love that. And, and there are two questions, David, that I, I love to ask every entrepreneur and I’m excited to hear your answers.
So the first one is, who are you in addition to being a CEO?
David: In addition to being A-C-E-O-I am a father and husband and just and I, and also I love to travel and. You know, I, I travel quite a bit even with work, but it’s sort of funny. Like I try to incorporate a little bit of fun into those trips too.
So, so that’s one of the things I love to do. I love to, I, I love to fish. I haven’t done it as much as I would like to do it, but hopefully someday I’ll get back into that. I’m, I’m sure I will. Our, our company’s starting to get to a stage where I can start to back out a little bit more every day and start to really concentrate on what I’d love to do.
But I would tell you hiking is probably the number one and outside of traveling that I love to do. And then so I love to do that. And I would just say friends, yeah, I like to, I, I hate to say this, but I like to do yard work and I, I have people doing my yard now and I really miss it. But I just bought a house to put my office in, so there’s a little bit of yard work here.
Mm-hmm. And I, it is funny, I’m probably gonna hire somebody though because I just don’t have time with all the travel and everything, but I do love doing that. So those things may come back into my life over time. So.
Paige: Sure, sure. I love that. It’s the little things, right?
David: Yeah. Yeah. And, and, and really it’s, it is the little things that more than anything, and I, I just keep my life pretty quiet, I guess, now.
But at the same time, I, I, it’s pretty active with the clients and everything that’s going on.
Paige: Yeah. Yeah. And you know, the last question I have for you is, what is the impact that you wanna have at the end of every day?
David: At the end of every day? Oh boy, I, I sometimes that, that’s a que a good question.
Sometimes you leave the day not really realizing that goal. But my, my, my day would be to have done a little bit that day to move the company forward. To help my clients a little bit. That’s really what my goal is every day. Mm-hmm. And I think I really try to make sure I focus on that. And a really good day is when a client tells me, thank you, that we really made an impact on them.
That would be something that would really resonate with me and feel like I had lived that day correctly. So,
Paige: yeah. Yeah, that’s huge. Just to get that. That feedback in there and, and know tangibly what that impact has looked like for them. I’m sure. Yeah. Well, thank you so much, David. I know that there are just a ton of nuggets that you just dropped in this episode, and so I’m excited for, for others to hear it and just learn from your experience.
But I appreciate you so much coming on the show. I know you’re incredibly busy. And just thank you for, for everything that you’ve shared.
David: Well, thank you. I appreciate the opportunity and I look forward to seeing it on the internet.
Paige: Yeah. All righty. Well, we’ll see y’all next time.