From Social Worker to CEO: How Dr. Kiki Ramsey Built a Thriving Coaching Business

In this powerful episode of Career Coaching Secrets, Pedro sits down with Dr. Kiki Ramsey, positive psychologist, career coach, author of Get Courageous Now, and CEO of the Positive Psychology Coaching & Diversity Institute.

Dr. Kiki shares her journey from social worker and motivational speaker to building a multi-layered coaching business — and the hard lessons she learned about pricing, self-worth, and opportunity along the way. From losing a $2,000 speaking gig over $500 to understanding the true value of exposure and alignment, this conversation dives deep into the mindset shifts that separate struggling coaches from sustainable ones.



Connect with

LinkedIn: https://www.linkedin.com/in/drkikiramsey/
Website: https://www.kikiramsey.com/
 

Transcript

Kiki Ramsey 0:00

I've always been a pretty confident person. That is just who I am. And even when I was new to business, because my husband is a graphic designer, I look like I was 20 years in the game, honey. Like I would I look like a million bucks, but I was only making $2. But you would know it because I look like that, right? I think that over the years, as my confidence grew more, I was able to charge more. But I had to learn some really hard lessons in the beginning, charging. One lesson in particular just stands out to me so much. And this is on the speaking side, but it relates to coaching because anytime I speak, I get coaching clients.

Davis Nguyen 0:41

Welcome to Career Coaching Secrets, the podcast where we talk with successful career coaches on how they built their success and the hard lessons they learned along the way. My name is Davis Wynne, and I'm the founder of Purple Circle, where we help career coaches scale their business to $100,000 years, $100,000 months, and even $100,000 weeks. Before Purple Circle, I've grown several seven and eight-figure career coaching businesses myself and have been a consultant at two career coaching businesses that are doing over $100 million each. Whether you're an established coach or building your practice for the first time, go discover the secrets to elevating your coaching business.

Pedro 1:12

Welcome to Career Coaching Secrets Podcast. I'm Pedro and today's guest is Dr. Kiki Ramsey, a positive psychologist and career coach who helps organizations transform their people through positive psychology and diversity, equity and inclusion. As the CEO of the Positive Psychology Coaching and Diversity Institute, she supports leaders and teams in building purpose, resilience, and a genuine sense of belonging at work. With over a decade of research, coaching, and teaching, Dr. Kiki blends business, psychology, and leadership development to help people advance their careers and do work they truly care about. She's the author of Get Courageous Now and a regular contributor to Forbes, known for helping individuals and organizations thrive from the inside out. Welcome to the show, Kiki.

Kiki Ramsey 2:11

Thanks, Pedro. Excited to be here.

Pedro 2:16

And before we get into what you do now, I'm curious how this all actually started. So, what was going on in your life when coaching became more than just an idea?

Kiki Ramsey 2:27

Ooh, very good. So I started my career as a motivational speaker. And so I was going all around conferences, women's conferences, organizations, motivating people, women, to just follow their purpose, follow their dreams, overcome their challenges. And in the process of doing that, I would have people come up to me saying, I love what you talked about in your keynote. Could you please help me do that specific thing? Like the, you know, overcome this challenge or overcome that challenge. And I'm like, sure. Because you know how we are, honey. Well, listen, when you ask, I shall give. And so I didn't honestly know that that thing was called coaching. At the time, I was a social worker. So I felt like I was great at helping anyway. So I knew I would find a way. But as I was doing my research, I'm like, wait, there is a thing called coaching that I can do. And so I started following the path and really, you know, trying to understand what coaching really was. But then I also realized that there was a thing called positive psychology. And that is the study of what goes right with you versus only focusing on what's wrong. And when I found that and coaching at the same time, I was like, I'm here. Like this is this is what I was supposed to be doing all my entire life. And so that's how I actually fell into coaching.

Pedro 4:00

I love that. I love the transparency. I love how honest you are about it. And I had to emphasize one thing, is which is the social work, right? This is such an identity drive profession. It's like, oh my God. And you just browse through it. But I feel like that is somewhat something that kind of pushed you where you are right now. Yeah. You know? Yeah. The speaking gigs and all that, of course. But being a social worker at the end of the day is I I'm gonna find a way to help people and get paid by, you know, it's something like that, if that makes any sense. Sorry.

Kiki Ramsey 4:32

Yeah. No, it makes perfect sense. Yeah. Yeah.

Pedro 4:35

And and at what point did it stop feeling like a side thing or a calling? And it starts feeling like an actual business you are responsible for.

Kiki Ramsey 4:44

So when, you know, as a social worker, you know, if you know anything about the profession, it's so it's noble, it's beautiful. We're really in the trenches helping clients and everything, but it's also very hard. It's tough. We see things on a daily basis. We see suffering. We see trauma on a daily basis that most people don't see in their lifetime. And as an empath, meaning I feel all the I feel all the things. It was very hard. It got really, really hard to come home every day and not cry or not, you know, be sick over something that I heard or seen. And it just got to be too much. And so for me, I started thinking about, you know, when I started transitioning to coaching, I can still use all my skills as a social worker, all the things that I've learned to help people, but use it in a different way. And what people are gonna come to me for coaching for is not as harsh as social work. So I really started thinking that this could be really my next, my next thing, because I needed something that was lighter, but would allow me to use the skills that I've been paid all this money for to go to school to learn. And for me, it just stopped being this side um hustle. And I ultimately quit my job as a social worker to pursue it on a more full-time basis. Once I realized that this was a viable way for me to continue to do what I love to do, which is ultimately help people.

Pedro 6:21

Okay. And once you are out there helping people, right? Especially in the coaching space now we're talking about, who did you naturally end up attracting? Like, when did you realize, yeah, these are the people I work best with?

Kiki Ramsey 6:34

Yeah, women. I mean, forget all men. No, it was for me, it was always women. And it was always like that because I grew up with a mom who had an addiction. And so basically, she was my first client. So I was always trying to help her be better, become a better, you know, just human for herself. Um, so I always attract women, even in my social work uh, you know, career, I was always helping women. And so as a as a coach, it just continued. One of the things that I believe about women is that we a lot of times play very small, but we are so mighty. And there's so many things that we don't we don't get to these levels in terms of potential for a whole bunch of different reasons. But it's always been my mission to help women succeed and to ultimately walk in their purpose.

Pedro 7:28

And that was from the get-go. They you just naturally attracted them.

Kiki Ramsey 7:33

From the very start.

Pedro 7:34

That's interesting. I like it. You know, now let's zoom out for a second. If someone someone ends up working with you today, how do they usually find you, you know, those women, their way to f to you in the first place?

Kiki Ramsey 7:47

Yeah, absolutely. I believe like right now, a lot of women find me. Number one, word of mouth. My clients speak for themselves. Um, once you work with me, they tell other women about like the transformation that they've gotten. And so it's word of mouth. And then I'm pretty, I'm pretty okay on social media. Um, so people She's being humble, guys. Social media. So people will reach out to me on uh social media. They'll also tell me like they've uh you know been following me for years, and uh and so then we enter into a coaching relationship and then speaking. I do a lot of keynote presentations across the country, and a lot of women see me from there and then ultimately hire me as a coach.

Pedro 8:32

Okay. Now let's talk about mechanics behind the scenes for a moment. So when someone decides to work with you, right, they watch the keynote, they a referral, like word word of mouth, like you said, what does that actually look like from their perspective? You know, how does the the I would say the client journey looks like?

Kiki Ramsey 8:52

Yeah, so for me, if somebody wants to work directly with me, because you all understand, I also have a coaching business where I have other coaches who work for me as well. But when they want to work specifically with me, which I don't take like a lot of clients because I'm doing all the other things, they will normally somehow get word to me, whether it's via email or our web, you know, my website through the contact page or social media, any of that, once they get word that we get word that somebody wants to work with me, we send them a coaching kind of like intake form. And it's like an interest form, right? Basically, like why, you know, what do you want coaching on? What's your budget? You know, have you ever had coaching before? What's your industry? All of that. And then once they do that, then we schedule a 30-minute kind of like discovery call where I get on the phone with them specifically because I want to make sure that I talk to talk to the women who I'm wanna, you know, coach to make sure there's synergy, right? Because there's not always synergy. And once we get on, I talk to them about what's going on with them, what they want coaching on. If I feel like there's synergy, I give them how my coaching works, my rates, and then I let them decide if they want to move forward. And that's how we go about the process in terms of them coaching with me.

Pedro 10:15

Yeah, I mean, your work seems pretty involved, right? You're talking about two businesses, one that you have other coaches, one that you coach yourself, right? We're talking about discovery calls, so we're talking about coaching clients also, not to mention the speaking gigs, right? Keynote. So, how do you think about managing your time and energy so the business doesn't start owning you?

Kiki Ramsey 10:36

Yeah. So I'm very, very fortunate that I have a full-time assistant who works for my organization. We have a full-time director of coaching and training, and we have a full-time CT, we have a full-time business development um uh um person in our organization. So I don't do all the jobs anymore. I used to. I used to do all the jobs, but I don't do all the jobs anymore. So I'm very fortunate to not have to do all the things that I'm telling you. So all those processes, it sh the my client gets to me when I'm actually on the phone. But all the rest of the stuff, I don't have to touch until I get on a phone call with them and see if we are a good fit. So I'm I'm blessed in that sense. But I I know how it is to have to do all those jobs because at once I was doing all of them and then some.

Pedro 11:28

You know, Kiki, I I feel like I have to tap into your experience a little bit, you know, because pricing is such a hot topic in the the coaching space. And obviously, we're not talking about hard numbers, but how do you approach, you know, pricing that now? And what did you have to learn the hard way to get where you are right now? And the reason I asked this is because it's so tied to self-worth, especially in the service-based industries, right? And they're like, oh, I'm not doing anything, my schedule is free, but I'm gonna, should I charge that much? Should I am I charge enough? Am I charging too much? So please enlighten me on price.

Kiki Ramsey 12:04

You hit the nail on the head when you talked about pricing is directly tied to self-worth. Uh I have, I've always been a pretty confident person. That is just who I am. And even when I was new to business, because my husband is a graphic designer, I look like I was 20 years in the game, honey. Like I would, I look like a million bucks, but I was only making $2. But you wouldn't know it because I look like that, right? And so I think that, you know, over the years, as my confidence grew more, I was able to charge more. But I had to learn some really hard lessons in the beginning of charging. And one lesson in particular just stands out to me so much. And this is on the on the speaking side, but it relates to coaching because anytime I speak, I get coaching clients. If I don't speak, then of course, those those clients I don't have the potential to get. So I was someone was reaching out to me to do a keynote, and I was at the time charging $2,000 for my keynotes, and they only had five. But this audience was perfect. These were women leaders at the time. This was the federal, uh, federal government branch. And I was just a real stickler on the fact that I wanted my $2,000. And so I lost the gig. I did not get the gig, which for me, when I speak, it's double whammy because you're number one, you're paying me. And then you're putting me in front of an audience where it's my target market where I can ultimately get coaching clients from. So I didn't, I didn't um do that keynote. And then at the time I had a mentor. He said, Okay, you didn't do the keynote, cool. How much money did you make on that day? I was like, come again. He said, uh, on the day that you were supposed to do the keynote, that you turned down $500 and to be in the front of a room full of your uh target client, how much money did you make? And I'm like, nothing. He said, Oh, that was real smart. Wounded. Okay. I was wounded. So I was like, oh, let me get off whatever pedestal that I'm on to realize the real opportunity. So I think that when pricing, right, sometimes we don't realize the real opportunity out here. There is opportunity, and sometimes we have to grow to a level to be able to give the kind of prices that we want to give to people. And I'm okay with that. And I and I teach that in my classes and everything like that. Where you start is not where you end. But if you start too high sometimes, people will never buy. So, how are you gonna get the experience if you're too high? So I say, still have the work, I still have value, even if I was going in at $500, but I couldn't see the real, uh, the real gift in that was I'm gonna be able to talk to all these women and get coaching clients. And they may see a higher value of me than what they could afford to pay me for in terms of a speaking engagement. So I think that when we talk about pricing for coaching, it is all over the place. But ultimately, I think we need to be in a place where we feel good about what we charge, but it's also accessible to our target market, right? It has to be accessible enough to your target market, which means you need to know your audience to know what they will pay. And to understand that there are gonna be some people who won't pay it. And if you're okay with that fallout, then perfect. If not, then you might need to make some adjustments.

Pedro 15:47

I love that. You know, especially in the part where you highlighted or highlighted the reps, you know. Sometimes, okay, you you need to charge X, Y, and Z, but you actually you need to start doing something first. You need a coaching call to learn, to feel, to understand that is your ICP, you know? And and sometimes, and I I am somewhat of a career coach, like not like your level, but uh I help Brazilians on land tech jobs internationally, and we were talking about Brazil before the podcast. But it's I learned so much in my first calls, it was ridiculous. You know, it's like I'm expecting a mock interview, I'm expecting a resume, a cover letter, and adjusting all of that. And the first mention he tells me and when we're talking like the cover letter, it's like, hey, right here, a personal note, something fun about you, something interesting. You don't have to go too deep. And he's like, There's nothing interesting about me, man. And I'm like, you know, I wasn't prepared for that. You know, like prepare entire lessons, classes, and one-on-ones with him. But then he told me that, I hey, wait a minute, you know. So I think the raps, you nailed it. You know, it's not just about how much you charge, it's where you're at right now. And find your ICP and the middle. A number that works for both of you, and you can deliver value and you feel you know you're being valued as well. So I love that. Okay. Awesome. Now moving forward, I want to hear from you. What's the direction you're aiming this business towards? And I know you have more than one, okay? So I would call it your energy. So are you thinking more about growth, leverage, building a team, or refining what already works? You know, what what feels most exciting right now?

Kiki Ramsey 17:31

Yeah. Yeah, you know, for for for me, it's definitely growth. We have some new programs that are out, um, coach training programs and all that. And my goal is to be able to produce coaches all over the world with our training model. And in order to do that, it's gonna cause growth. It's gonna call, it's gonna call for more marketing. I wanna be the, you know, the first and foremost person that people look to for career coaching, um, especially in the African American community. I don't only coach African American women, but I think that they can see me and see themselves in me. And so I want to be the go-to for women when they're thinking about being burnout or unhappy with their careers. And I also want to train other coaches to be able to do the same.

Pedro 18:23

Great. I love the goals. They're big. That's how they should meant to be to impact more people, right? That's all about that. So even when things are going well, there's always something under construction. Like, what's the main thing you're actively working on or trying to improve in the business right now?

Kiki Ramsey 18:39

Yeah, for us, we are trying to improve our systems and processes. We do a lot of stuff that's manual. We always joke that we're building this plane while we're flying it. You know? And so, and I mean, not to all the startups, you know, we consider ourselves a baby startup. Um, and I think sometimes you just have to get in the ring and you have to, you have to do it. So many of us just wait and we wait and wait and wait till all these things are perfect, and then we don't start, or we start later than we want it to. So for us as systems and processes, we do a lot of things manually. There's a lot of things that we could be way more efficient at if we fixed our systems and the way things worked and we automated things and and everything like that. So we are currently working on getting those things in place so that it frees up the staff to do the important things, which is business development.

Pedro 19:36

Yeah, that makes perfect sense. The structure, right? So you can just plug in a new client and plug in a new employee so they can grow inside that structure. That makes perfect sense. Okay. I mean, Kiki, I have to tap into your experience a little bit more now. You've been around long enough, you know, in the game to see trends come and go. You know, people give business advice non-stop, especially online. So, what's something you hear repeated a lot that you think people misunderstand or overvalue?

Kiki Ramsey 20:06

Overvalue? Ooh, goodness. Let's see. People misunderstand or overvalue. I think that people overvalue trying to get and be perfect, right? Like, I think when I'm out here and I'm looking online or when I'm teaching a class, everybody feels like in order to get online, in order to start talking, in order to get a client, they have to be the perfect version of themselves. And I'm like, who told you that? I am so not perfect. Sometimes I slur my words. I mean, it's it's just it's it's a it's a tough thing when you feel like you can't move forward because you have to, you know, cross all your T's, dot all your I's. And I see so many beautiful human beings not start or not put themselves out there for fear that people are gonna judge them, which people are, because we as a very judgy, a very judgy nation, honey. Like that's what to me, if you're on social media, you're saying, hey, judge me, because people are gonna do it whether you want them or not. But you have to be more confident in your skin to understand that you're gonna be for some people and some people you're not gonna be for. And that's just that's just business.

Pedro 21:24

So yeah, that is that is so true. Especially the, you know, that perfectionist mentality, which is in short sight, it is really fear of judgment, because my work will be so perfect, nobody's gonna be able to talk bad about it, and nobody's gonna be able to call me out on something. And I get it, sometimes it's upbringing, right? Sometimes our people that were raised in ways that I wouldn't call it bad, but it shouldn't be raised in those certain ways, and they create this shell, I can tell, because in some extent, not because I was raised like that, but I had somewhat of that. You know, and I I can resonate with what you just said perfectly. It's like before a website, before is my camera the best module ever ever, you know, out there. Is my microphone perfect? You know, and so nobody's gonna be able to criticize me. But at the same time, it feels like people they don't care, right? Even even they're busy doing their own stuff, also. It's not like, oh, I'm gonna be on TV tomorrow and a million people are gonna look at me. It's not like that. Social media is not like that at all right now. So I really, I really I can really see what you told me here. I really love that. And on the flip side, right? What's something boring or notice hyped that you wish more people actually paid attention to?

Kiki Ramsey 22:43

So I think I'm a I'm a certified coach, right? And I wish more people paid attention to who they're coaching with. And I'm I'm I'm a big proponent of getting certifications. But you said earlier, everybody out there is a business coach, and then half of them ain't never went to coaching school. They never they ain't got a certification here or nothing. And I get it, people think that they know what coaching really is. What most people think is coaching is consulting, is you telling somebody else what to do, how to do it. But in coaching, we believe that the person holds the answers to their problems. We are nobody's savior. And I feel like more clients should pay attention to whether their coach has a certification or has been to some kind of coach training school to know what coaching truly is and a transformation that they can get out of coaching because the coach understands what coaching is.

Pedro 23:45

You know what I've seen, and I want to see if you if you saw that in the market. I've seen coaches positioning themselves not as coaches anymore, because they don't want people to have a misinterpretation of coaching, what coaching actually is. So they kind of position themselves somewhat of a consultant, which eventually will bring coaching into the piece. I'm not sure if you've seen something like that because it sounds like coaching. People think sometimes that we're gonna light up some candles, we're gonna dance kumbaya and all that, but it really is not a lie about that. Or they think we're gonna give them the answers, you know, like it's do you have you seen anything like that? I'm just out of curiosity, really.

Kiki Ramsey 24:28

No, not really. I've I've I've seen so many people hang up their shingles to say I'm a coach, right? And to be honest, right? When I was a social worker, I thought I knew what coaching was. And I started coaching prior to going to coach training school. And I'm like, you know what? I'm smart, I have a master's in social work, I know what coaching is because I am very bossy, honey. So I can tell a person, I think, or two, about what to do with their life, right? And so I knew. And then I was like, you know what? Anything that I, you know, decide to accomplish, set myself a goal for, I'm like, I need to learn. So I said, you know what? Let me go ahead and go to coach training school because I want to be the best. And then I got into coach training school and I'm like, wait, this is coaching, not that. What I was doing. But I was still charging a whole good good sum of money because I thought I knew what I was doing. So I just think that I see a lot of coaches out there, and the majority of them, they have had no training at all as to become a coach.

Pedro 25:34

And something you said actually made me curious about, you know, when was the last time a client asked a coach and a sales call, oh, are you certified? That this doesn't happen so often, right?

Kiki Ramsey 25:46

It don't normally happen at all. When people get on the phone with me like doing those discovery calls, I highlight that. And I and I tell them this I say, listen, regardless of if you decide to go with me or not, look for a coach who is certified. I I tell them, I'm like, look for a coach who is certified because this is a person who understands what coaching is, and they're gonna help you go from A to where you want to be. You like what I did there?

Pedro 26:14

I like it. And I like the way you framed that. That's perfectly framed for a sales call, okay? I'm gonna give you that. That's just like whether we work together or not, look for a coach that, well, it's actually me, but look for a coach that is certified. So yeah, I love that. Yeah, I like that. You know, Kiki, before we close this out, if someone resonated with what you shared and wants to follow your work, where should they go?

Kiki Ramsey 26:40

Well, they can go to my website, which is uh drkiki.com, and you can find me on every social media site there is, it's all under Dr. Kiki. I have tons of videos that you can kind of get some quasi-coaching from before you even ever talk to me on YouTube. Um, and so yeah, I'm I'm I'm all over the place. I can't be missed.

Pedro 27:03

Okay. Yeah, that yeah, I can tell you that. Okay. If you were in any shape, form, or any way you had a doubt, I I'm gonna kill it right away. Uh yeah, I can tell you that. Okay, you know, there were a few moments from this chat that really stood out to me. I I think the social worker part, I think this is the first time I talked to a social worker that is also a coach. I really and I I've talked to hundreds of teachers, okay, which is also super identity-driven profession, but a social worker, and oh my god, social workers. You're losing a bit now. You should be coaching more. This is awesome. I mean, it's just finding another way to make money and help people. So yeah, I commend you on that. That's so cool. And also, Kiki, I have to commend you on the fact that you're you share the way you shared stuff, it's so openly, you know, so vulnerable, which I think is what coaching is about. Because at the end of the day, you're asking your client to be vulnerable. It's only fair you do the same. Like you share with me and with our audience how your mom had addiction, for example, which I can't even imagine to understand what you've been through. But just by sharing that, you know, oh my god, that that is so powerful. So thank you for that, okay? I really appreciate that. And I uh on a on the other side, Kiki, you know, you're telling me that you're looking like a million worth two dollars. I love that. That's also being vulnerable in a different aspect. This is the business aspect, so I commend you on that. That is so awesome. So, Kiki, I really appreciate you taking the time being open with this. It was great having you on.

Kiki Ramsey 28:49

Thanks, Pedro. It's been a pleasure. I I think me and you could just keep on talking because we were having such a great time, even pre-show and all of that. Yeah. Next thing you know, I'm gonna be rolling up in Brazil like Pedro. I'm here.

Pedro 29:05

Well, well, well, but Brazil is pretty big, but we'll be happy to welcome you. And you never know. Maybe you do a keynote here. Hey, how about that?

Kiki Ramsey 29:13

That'd be so awesome.

Pedro 29:14

I'll help you with Portuguese. No, I'm just kidding.

Kiki Ramsey 29:17

No, that would be awesome. My husband really wants to learn Portuguese so bad.

Pedro 29:21

Okay. Oh, well, awesome having you.

Davis Nguyen 29:24

Really appreciate it, okay?

Kiki Ramsey 29:25

Thank you.

Davis Nguyen 29:26

That's it for this episode of Career Coaching Secrets. If you enjoyed this conversation, you can subscribe on YouTube, Spotify, Apple Podcasts, or wherever you're listening to this episode to catch future episodes. This podcast was brought to you by Purple Circle, where we help career coaches scale their business to $100,000 years, $100,000 months, or even $100,000 weeks, all without burning out and making sure that you're making the impact and having the life that you want. To learn more about our community and how we can help you, visit join purplecircle.com, yeah.