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Ana Chaud With FiftyPages

July 21, 2025 by Jacob Lapera

High Velocity Radio
High Velocity Radio
Ana Chaud With FiftyPages
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Ana Chaud is the Co-Founder and COO of FiftyPages and a seasoned entrepreneur with nearly three decades of experience guiding startups and scaling businesses. Born and raised in Brazil, she immigrated to the U.S. at 21 and built a life marked by personal reinvention and professional achievement. From strategic planning and funding to operations and financial modeling, she has worn every hat in the business world—and now, she’s turning her focus to thought leadership, helping others discover fulfillment beyond career success.

Raised in a home that championed female independence, she grew up believing that women could do anything. Yet her life has been a testament to the idea that a singular “calling” isn’t always revealed early on and that meaning and reinvention can occur at any stage.

With a BA in Communications, an MBA in Finance, and a wide range of professional certifications, she combines academic depth with lived experience. Her career journey has reflected constant evolution, with each chapter revealing new possibilities and passions.
Ana’s true zone of genius lies in helping high-achieving individuals reconnect with what matters most.

She is known for turning abstract visions into tangible results guiding clients through transformative moments with clarity, purpose, and action. She is not interested in empty motivation; she is relentlessly focused on helping people make the most of what they have now, chart what comes next, and pursue lives of deeper satisfaction and significance.

Outside of the boardroom, she brings joy and discipline to everything she does. A classically trained ballet dancer and passionate salsa enthusiast, she remains deeply committed to movement, wellness, and vibrant living. She’s also an avid reader, a devoted cook who finds expression through food, and a curious student of human biology and behavior.

Now an empty nester with two college-aged sons, she continues to explore what it means to live fully with freedom, intention, and joy.

Connect with Anna on LinkedIn.

What You’ll Learn in This Episode

  • Success Isn’t Always Fulfillment: Why High-Achieving People Are Redefining What Comes Next

Transcript-iconThis transcript is machine transcribed by Sonix.

 

TRANSCRIPT

Intro: Broadcasting live from the Business RadioX studios in Atlanta, Georgia. It’s time for High Velocity Radio.

Lee Kantor: Lee Kantor here. Another episode of High Velocity Radio in this is going to be a good one. Today on the show we have Ana Chaud and she is the Co-founder and CEO of FiftyPages. Welcome.

Ana Chaud: Thank you. Thank you for having me, Lee.

Lee Kantor: Well, I’m excited to learn what you’re up to. Tell us about FiftyPages. How you serving folks?

Ana Chaud: Yeah. So it’s basically the result of over 30 years working with high performing leaders, mostly founders and CEOs and 50 pages. We created a program that helps high performance, um, create what we call a strategic life design. It’s basically applying the strategic thinking that they put into their businesses, into their personal lives and creating, um, either a life currently or maybe a next chapter in their careers that is a little bit more aligned with what they want. Uh, something that’s more fulfilling, that’s going to bring them more joy and, and just more happiness in general. So that’s what we do.

Lee Kantor: So what’s your backstory? How did you get involved in this line of work?

Ana Chaud: Oh, it’s a long back story, but in summary, it’s been over three decades now that I worked one on one with leaders, either as a coach, as a consultant, uh, collaborated and also have been a founder myself and have grown, scaled and sold a few businesses or have been in the founders shoes. And along this journey, what I noticed with my clients is that the majority of them have no problem On hitting business goals, right? They can do whatever they put their mind into. But what I noticed is that that wasn’t the truth in their personal lives. Like, they wouldn’t bring the same passion and same enthusiasm personally. And then a great portion of my clients graduated to that, that part of life where you think, what’s next for me? What am I doing this for? What? How am I going to live the next, you know, 30, 40 years? So it’s time to think what is the next stage in our lives? And a lot of them get really stuck because they don’t know what they want. They spent so much time growing businesses, you know, making sure that they were successful professionally and always thinking that achieving success in your career would eventually bring happiness and fulfillment in personal lives. And it’s not always the case. So when in a few years after the pandemic and after I had sold my business and I went to coach clients. I realized that that was a big stock. It was actually figuring out what they wanted personally, so that they could create a business strategy that would support that personal vision. And and in that, during that process, I met my current business partner, Elliot Weisel. And he had created a fantastic program to take leaders through. And what is today 50 pages. So we decided to join forces and create a comprehensive program that takes leaders into a systematic approach, which is a, you know, a step by step approach to help them design what they want personally, and then they can go back to the business and then create a strategy for the business that’s actually going to support what they want personally.

Lee Kantor: So the people that are open to this kind of thinking and might be ready for the shift, I guess a mindset shift. What what are kind of some of the symptoms? What are some of the clues that, hey, this leader maybe needs, um, kind of a a new game plan for this next stage.

Ana Chaud: Usually it starts with a nudge. Right there is we all come to that point in our lives, I think, after 40. I mean, most of our audience is 40 plus where you are. You are rethinking everything you’ve done. You either going into a new phase of your life, say you kids are grown and now you’re becoming an empty nester, or you have hit a point in your business that you feel like it’s time to exit or you’re approaching the perceived age of retirement, right? If you’re a high exec now, you’re thinking, oh, am I going to retire? So there’s always a trigger point where I need to think what’s next for me? And what we identified with our clients is that the more successful they are, the more they identify what the position that they’re in, and it’s harder for them to let go. Right. There is a piece of, I have this title, or I am the CEO of this company, and in particular for women, because even though I do work with, you know, the general audience, I definitely focus on women leaders because I am one of them. And I’ve been in their shoes more than not. And women in particular get to that point where what’s next for me? But if they have hit a very high position in their careers, it’s a lot harder for a woman to say, oh, I’m just going to, you know, start over. So it’s having the ability to identify that you have a nudge to know what’s next for you and have the courage to try and pursue something that would make you happier. So there is a Venn diagram there of acknowledgment. Feeling that trigger and then wanting to pursue something else new, more exciting perhaps.

Lee Kantor: So the type of coaching you’re doing in this regard is, is more about kind of this next step rather than the nuts and bolts of their business.

Ana Chaud: Correct. I’ve done my 30 years of coaching and advising has been on how to make your current business as successful as possible. I’ve done that left right, you know, up and down. That is not really the big question. I think that making a business successful today is not the biggest challenge. I think the biggest challenge is am I happy and fulfilled in this particular position today? Is this what I want to be doing for the next 30 years? 40. And if so, how do I Well, how do I align with what I’m doing? I think that’s the most important part. So the coaching is the acknowledgment of where I am. I don’t believe anybody has to have a transformation. It’s not like everyone needs to change or it’s not like everyone needs to transform. But I am a firm believer that everyone should be aligned with what they want personally. And if that position, their career, their job, whatever it is they’re going through. If that is aligned with what they want, then that’s fine. Then then that’s a beautiful thing, is just having that awareness that they are where they’re supposed to be.

Lee Kantor: And like you said earlier, like a lot of their identity is wrapped up in what they’re doing. And then to take that step into the kind of an unknown or the next thing is scary for a lot of people because all of a sudden they’re not that CEO anymore, or they or they I guess they in your case, they could be the CEO and do this other thing too. But if they want to align with their purpose, sometimes it means leaving some things behind.

Ana Chaud: That is exactly it. I think that but but, but but more importantly is figuring out what that purpose is. Right. I think a lot of us don’t know. So we we hang on to what we have. And there is also a piece you can’t forget which is not only aligning with the identity. Like if I wake up the next day and it happened to me personally when I sold my business, and when I woke up the next day and I was no longer the founder CEO of my company, there was that moment of like, who am I right now? There is that piece, but there is also a piece that we never talk about with the guilt and shame. A lot of people who achieve high positions in their careers feel like they have better than most people, which is true. And so if they feel a little bit unhappy or dissatisfied, they don’t understand why that’s happening. And there is a guilt that comes with it of feeling, you know, unfulfilled or feeling, um, misaligned. So we also addressed that piece because the identity is easy to see. I think for any leader, it’s easier. It’s easy for them to recognize that they have an attachment to an identity. Right? They they are attached to the position, to the power, to the accomplishments. What are they going to be? But they don’t like to acknowledge that there is a piece of guilt and shame of feeling, um, misaligned or feeling like they’re not what they want to be. So we address that as well. And then what we do is we try to figure out a way that we design what is the the what is the the picture that would make you feel good. And then we create steps towards that that will help them leave the identity, leave the guilt, leave the shame behind, and then get into what they feel. It’s what they want to do.

Lee Kantor: Now you’re talking a lot about entrepreneurs as the, uh, coaching clients that you’ve had. Do you ever work with like executives that maybe are with enterprise organizations and, and they get maybe laid off or something happens late in their career and then they don’t have that cachet they thought they had, like when there was Bob who worked with, you know, IBM. And then he was getting his phone calls returned. But when he’s Bob with Bob’s Consultancy, he’s not getting his phone calls returned. And that kind of, uh, you know, when they get punched in the face with that realization that may be their company was what people were attracted to. Not them as individuals. Uh, then they get into kind of a tailspin. Do you do you work with clients like that?

Ana Chaud: Yeah. As a matter of fact, most of our clients are like that because the the high execs have it. It’s a little different. Right. Because they have to. They put their their heart and soul into their business. And then what you described happens very often. All of a sudden they’re no longer part of that organization. And everything they put into it, it’s not there anymore. This happens as well to to founders. You know, it really does, in particular founders who end up getting acquired more times than not. The original founders CEO gets like, it’s like go or it leaves the company with nothing. It happens very often. So it happens on both sides. But we do work with high execs because that is the one where, um, a lot of times the execs don’t have the same sense of agency that that a founder and entrepreneur does, like a founder entrepreneur. They do have a sense of agency because they realize they created or started a business by choice. So they when they take the consequences, they have a little bit more like, oh, I chose this. And, and then they, they manage or handle that different than a high exec. But we do work with execs, in particular women. Like I said, I do work with the audits, but the, the the executive level for a woman is a lot harder than it is for a man. And I am leaving.

Ana Chaud: And then in particular after 50, which no matter what we say, there is a lot of ageism. A lot of women get pushed out after that age, and it’s much harder for them to find a position, and that is for men after 50. So what we do is, um, we start figuring out really what who they are. You know, they they take everything that they have learned over the years working for that corporation. What are they strengths. What they bring value. And then we define that person. And what is it that they want to be doing based on? That is how we create what’s next for them. But the idea of what we do is that they step into that next chapter without the fear of the unknown, because no matter what we do, there’s always going to be a piece of the outcome that is not controllable, right? Nothing we do can dictate what the outcome is, but what we help is figure out how to react and how to adapt to what that outcome is. And that’s our job is figure that out. And it’s helping them know that they don’t know what that next step is going to be, but they know how to act and react to it as they step through the path that they’re going to go to get to the next, to the next steps. You know what I mean?

Lee Kantor: Yeah. Now, what does the kind of the early conversations when someone is, um, considering working with you? What some of the questions you asked them to make sure they’re the right fit and their, you know, their their mindset is going to be open to this type of, uh, I’m sure, hard questions you’re asking them and challenges so that, you know, to make sure that this is going to get them to where they want to go, what is kind of either the pre work or the early kind of, uh, conversations you have with a potential client.

Ana Chaud: Yeah. So the first thing we start to talk about is, you know, is there a is there a voice. Is there something that they feel that’s missing in their lives? And when I say missing, I’m not talking, oh my gosh, I need a boat or I need another bag I’m talking about. Is there something inside Side that you feel that you’re asking yourself, you know, is this what I’m here to do or do? I love what I’m doing. That’s one of the things we ask. Another thing that we identify is if you’re having a feeling of burnout. Burnout is a big indicator that somebody is not doing or is not aligned with what they want to be. Because what’s happening is when you do something and you don’t feel energized by it, that’s when the feeling of burnout comes in because you have no nothing else to give. So burnout is something that people describe it a lot. Another thing that they feel is this, uh, sense of over commitment. And, uh, so when when we’re having the first conversation and we’re talking, I start to identify based on what their struggles are. So I say, I ask, you know, what keeps you up at night? Or give me an idea of what your day to day is like. And based on these answers, what we identify is there’s a lot of over commitment, right? You’re going from one thing to the next, to the next, to the next.

Ana Chaud: And that over commitment becomes the reason why they don’t promote self-care. So if somebody doesn’t promote self-care and they say, I don’t have time, I don’t do this, I have to do this. I have to do this. There’s always a reason. That is where you notice that what they’re doing is, is that they are putting themselves into this hamster wheel that prevents them from actually promoting self-care. So that’s over commitment, over scheduling. Um, another symptom we notice a lot is working. It’s like having a default life, right? I have to do this because I have to pay for my kids education, because I have to pay a mortgage, because I have to pay a car. So when you feel like you have the sense of obligation and you’re doing what you’re supposed to do. That is another sign that there is misalignment. So those are things that we pick up when we have a conversation. And we know somebody has basically checked all the boxes of success. Right. They they either succeed in their career. They they have material things that they always wanted to. So they they fit all the boxes of success. But there’s still the sense of fulfillment. That’s when we identify that.

Lee Kantor: So what is some piece of advice or some, um, action that a person could take right now if they’re feeling kind of stuck like that? Is there something that they can do today, right now, after listening to this, that could maybe give them a glimmer of what it could be?

Ana Chaud: Yes. I think it always starts with acknowledgment. It really is accepting the feeling. So first thing that I would recommend is if you have a discomfort, if something is not feeling right, don’t try to find a reason right away. Right. I’m not feeling happy. Oh, it’s because I didn’t sleep last night. Oh, I’m not feeling this. Oh, it’s because I did this. So I used to stay with that and then and then start tracking when it comes. So the first thing is acknowledging that you have a discomfort, whatever the discomfort is. And then once you acknowledge it is actually name it. I am feeling depressed or I’m sad today and then start to notice what’s causing it. Is the sadness coming? Like every Sunday night I don’t want to go to work. Is the sadness coming? Every time that I have to step into a board meeting is that is, do I have anxiety? Start to notice what is it? And then once you start to do that, you start to name it. Then you have something a little bit more concrete to work on, because if you you can’t change something that you don’t know exist. And if every time I get anxiety I reach for a pill, then I’m not really fixing. What I’m doing is I’m getting anxiety. I reach for a pill, I feel better, I step to the boardroom. But if I know that going to the boardroom is giving me anxiety, if I know that every time that I have to, I don’t know.

Ana Chaud: Look at my financial statements. I’m getting so tense and I don’t want to do it. You start to realize that there is a misalignment. So one thing that I, that I suggest my clients will do is take inventory on the activities of the day, what gives them energy and what sucks energy out of them. And it can be super simple, just taking a piece of paper and writing down and say, you know, I’m having a meeting today, and after the meeting, did I get energized about it? Did it get drained? Like, if I have to do and read financial reports, do I get energized or have you start to you start to take inventory of how your energy is either replenished or drained during the day. That’s a huge indicator of alignment and misalignment when you’re aligned. If you energize more than you don’t. So that is one big thing that anybody can do. Any time of the day is just take it a week and then analyze it. All the things you do. They give you energy and all the things that you do. They don’t they don’t give you energy. That’s one. That’s one practical step. Another practical step I can give to if you want to thank you, is to share, of course, one thing that I also give a tip to my clients is this you take a piece of paper and you write down all the areas of your life.

Ana Chaud: Just do columns of your life. So for example, your, your health or and that’s one column and then you have finances is another column. Your relationship with your spouse partner boyfriend girlfriend, whatever. It’s another column. If your spiritual your spirituality, your time. So what you do is you make these columns and the first thing you do is you rate them. Okay. How do I feel that from 0 to 10 that I am with my health and I say it’s a seven. And then with my finances it’s a eight, I just rank it. And after I do, I go into each column and I think, what would it be for me to rank as a ten? Why didn’t I rank, not rank my health as a ten? And then I list 2 or 3 things that I didn’t rank, you know that I didn’t know that I don’t have, that. I if I had those things, I would rank as a ten. It could be maybe I’m 10 pounds lighter, maybe I can, you know, run ten miles, whatever it is that I believe that if I had these things, I would have ranked eight at a time. Once you do that, what you’re doing is you’re identifying the gaps in each area of your life that are preventing you from saying, I have ten across the board, but what’s and then those give you practical things to work on.

Ana Chaud: But most importantly, is that what he does? He gives you the perspective of which area of your life needs more attention at that particular point in time. This is very Keeley, because people talk the word balance a lot. Balanced. Balanced, balanced. There is no balance. There is harmony. Why do I say that? Balance means you have to give equal weight to each piece of your life. If I balance work in life, I have to have equal on both sides, and that’s never going to happen because at different points of your life You’re going to have to give more attention to certain things. If I have kids in college, I have to give more attention to my finances at this particular time of my life because I need to pay for, you know, tuition. If I have if I’m going through a health, um, struggle, maybe I need to give more attention to my health right now, but maybe not two years from now. So when you know where you need to give more attention, it allows you to give more, um, energy towards that part of your life. And then once that part is taken care of, then you’re taking inventory again. And and then what you do is you find harmony and you make sure that everything is working in unison. That usually brings a lot more fulfillment and health to people in general.

Lee Kantor: That’s a brilliant, um, analysis. And I think harmony is such a better word than balance. I think you’re just right on the the money there. That is that is just just that sentence alone is a mindset shift for a lot of people. I mean, that was brilliant that that.

Ana Chaud: Thank you.

Lee Kantor: Thank you. Now, um, what exactly does the the program entail? Is this something that’s one on one coaching? Is a group coaching like what’s included when somebody signs up for the 50 pages, um, kind of, uh, experience.

Ana Chaud: Yeah. So it’s it’s six weeks and it’s one on one. Um, and usually one on one, either with me or with Elliot. And we guide our, our clients through the process. So each week we go through a different module. And, and there is a community, a community of peers that are usually in the same, you know, they’re going through the same struggles and they connect. Once in a while we could we do some group calls just for people can connect. And also So once we go through the program, which is six weeks, but the program is six meetings, each ideally will be six weeks, but usually people have ten weeks to complete. So obviously if you don’t, if you cannot make a week, it doesn’t mean that you’re not going to do it. But we do go through a very structured step by step. And at the end of the program, um, our clients come out with a very with a solid roadmap of what they need to do to, you know, to get to the picture that they designed. We come up with a picture of what they want in the next three years. Then we come and then we bring it to the 12 months, and then we break it down into quarters of what they need to do each quarter to get to the 12 month goals and then to the three year goals. And then after they complete the six weeks, we have a 12 month quarterly support where we have every three months, we have group calls where everybody comes in and we talk about, you know, how are they progressing on their goals on whatever they were set out to do. So that’s what the programing tells at this point. We have, you know, a series of there’s a lot of like thinking and deep, deep self-discovery. And so we do that one on one to allow this, this, this time and attention that they need to get to that place that they have to go in order to bring up the things that they need to bring in order to move forward.

Lee Kantor: So if somebody wants to learn more, have a more substantive conversation with you or somebody on the team, what’s the website? What’s the best way to connect?

Ana Chaud: Yeah. So they can either go to our website right now is being redone, but they can still go there and see what the program is about. It’s called 50 pages Dot life. So it’s just the word 50, the word pages about life because we’re we try to bring this idea to your life. It’s your story. You know, you write it, but you know. Always connect with me on LinkedIn, too. I am, you know, we’re very approachable. It’s very much we do this because we really want to change, uh, to make a bigger impact in people’s lives and particularly the leaders, because we believe in the ripple effect. Right. If we can change one leader by default, we’re changing so many other lives that they touch. And I think that’s important for us. So yeah, so connecting with me on LinkedIn on a child is great or we have social pages, but everything is 50 pages life.

Lee Kantor: Well, Ana, thank you so much for sharing your story. You’re doing such important work and we appreciate you.

Ana Chaud: Thank you. Thank you so much. It was a pleasure to talk to you.

Lee Kantor: All right. This is Lee Kantor. We’ll see you all next time on High Velocity Radio.

Filed Under: High Velocity Radio Tagged with: Ana Chaud, FiftyPages

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ABOUT YOUR HOSTS

Lee Kantor has been involved in internet radio, podcasting and blogging for quite some time now. Since he began, Lee has interviewed well over 1000 entrepreneurs, business owners, authors, celebrities, sales and marketing gurus and just all around great men and women. For over 30 years, Stone Payton has been helping organizations and the people who lead them drive their business strategies more effectively. Mr. Payton literally wrote the book on SPEED®: Never Fry Bacon In The Nude: And Other Lessons From The Quick & The Dead, and has dedicated his entire career to helping others produce Better Results In Less Time.

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