Finding Your Big Business Idea with Jessica Sato

Racheal Cook: Welcome Jess, to Promote Yourself to CEO. I'm so glad to have you on today. I'm excited to be here. I knew I had to have you on today because we've known each other for a while now. You've been working with us inside of the CEO Collective for a few years, and the more I've gotten to know you and talk with you about all of your incredible work, I knew we needed to have a conversation about the evolution that occurs as a small business owner and how that impacts how you're showing up, how that impacts the impact you want to make, how that impacts your messaging. But before we get into all of that, I would love for you to start by sharing a little bit about you and your business. How did you get to where you are now?
Jessica Sato: That's a little bit of a loaded question. Let's see. Well, just from a backdrop perspective, I came out of the corporate world like so many of the other women in the CEO Collective and was really looking to do business differently. And I didn't start out with some big grand, grandiose plan, like the kind of guidance that we are talking about so often about being a CEO and being strategic and having all that stuff. That was just not a thing. Like I literally built a business by accident and that evolved over the last 12, 13 years into what I am doing now, which is really focused around helping female entrepreneurs, particularly those who have a strong impact orientation, who are looking to deal with things on a social impact level or an industry change kind of perspective. Really helping them get crystal clear on their message, their work, the impact.
And that came about for a lot of different reasons. Some of that was just my own evolution, like you said, as a business owner where I could see myself growing. So what I started out is not anywhere near what I'm doing now. Where before it was all about corporate consulting. Now it's all about female entrepreneurs. Before it was a lot around mindset and also early stage entrepreneurs. Now I'm working with later stage entrepreneurs. Mindset's a part of it just because we're doing a lot of visibility work, but a lot of it is really getting very clear on what is it that you're actually trying to say in the world. So that evolution. The business is very much a function of my own evolution as the owner of that business.
Racheal Cook: And I think when you first came to us inside of the CEO Collective, when I first got to know you, you had really kind of made your mark as a speaking coach. Because you not only had been on stages, been on TEDx, but you were coaching others to land those types of speaking gigs. Can you tell us a little bit about that experience and what triggered you going from a speaking coach to really wanting to get into like, okay, what is this big idea and big impact you're trying to make in the world?
Jessica Sato: This is so fun because I fell into the TEDx world by accident. A colleague of mine reached out and she said, "Hey, do you want to be a speaker coach at TEDx Breckenridge?" It was their very first event, and I kind of noodled over that for a while. I wasn't totally sure because TEDx was never on my bucket list. I decided to give it a go and I really fell in love with the idea of big ideas. And TEDx is a very specific platform. It has a very specific structure and I find that it's really good for thought leadership and getting those big ideas out onto the stage. I mean, that's the whole design behind it.
But that really got me thinking about what happens when you have an idea that's not really well suited for the TEDx stage. And some would argue, oh, any idea will work. But I, from my own experience, I haven't found that to be the case. And what I started to realize is a lot of the women that I was working with were definitely leaning into like more social or social impact oriented things and at the time, TEDx was in a big AI tech kind of swing. And so there was just a weird mismatch. And so that really got me thinking about, well, what does it look like to have a big idea and what does that actually mean?
And to me, a big idea is really this sort of audacious idea or concept that demands attention. It's designed to challenge the status quo and then of course inspire action. I think for me, the work has really been about how do we unpack that, whether you're doing TEDx, whether you're doing that for some other part, whether that's, you know, you have deep expertise and knowledge, like how do you actually bring that to the surface in a way that allows the idea that you have or that unique perspective or point of view to really shine.
Racheal Cook: That's so much harder than people realize, I think because I think anyone who's been in business for a long time and has developed your own like thought leadership, your own frameworks, your own content for a long time where you've worked with tons of people, it's so hard to distill everything down into something that's really tight and memorable, and it kind of drives you crazy when you're sitting there going like, okay, I do this and I do that, and I think this, and I know people know me for this and this and this, but there's sometimes it can feel like you're being pulled in a million directions when you don't have that clarity. How do you help people find that through line and figure out like, okay, what is really at the center of all these things that I have built my brand or my business around?
Jessica Sato: I love that you call it a through line, because that's similar language to what I use. Because people have so much expertise. We're mired down in our own expertise and we cannot clearly see how it all fits together and we can't articulate that. So really trying to get back to that core is the actual work. I wish I could tell you that there's just like some magic formula for doing it, but the reality is a lot of it is listening and being on the outside looking in and really trying to hear or read between the lines of what someone else is saying. The analogy I use a lot is sort of like an umbrella where the core is the stem or the handle of that umbrella, and then you have this overarching thing. And each of those spokes is different perspectives that you can bring to the conversation. And we want to make sure that people are able to tie all of that together.
So some of that is going way back into a person's experience or their expertise and saying, "Oh wow, these are the pieces that actually make it go together," right? Like in the moment you're looking at all of your work and you don't totally see that. But if you actually take a step back and dig kind of deep, you can figure that out. Or some of it is just lived experience. And also paying attention to what is it that people start to know you as. So I take people through a pretty robust intensive that starts with some pre-work where they're doing a lot of thought dumping, and then we just talk through it over the course of a couple of sessions to really try to hone in on that very clear, very concise, essentially a statement, if I had to give it a word, that allows them to be able to articulate like, "Oh, this is my stance or my perspective on X, Y, or Z." And then from there, like you said, everything sort of pops out from that core.
Racheal Cook: Could you give a good example of maybe something that's more like consumer facing, that everybody kind of knows? That instantly kind of gives that concept.
Jessica Sato: So if I'm thinking like big, big brands, maybe it's less about the statement, but more about a stance that's very public facing. A great example of that is Ben and Jerry's, they've taken a very specific stand that's more socially oriented. You can look at Patagonia. These are like big companies that have essentially put a stake in the ground and said, "This is what we believe about the earth, about social issues, et cetera," and they sort of build their business around that. So some of that's around the business model itself. Like Patagonia is a great example where they've essentially built their business model around this core belief.
Even in the CEO Collective, a life first business is what I think of. That's the perspective or the stance. And from there, everything builds, right? The values are tied to that, the operating system is tied to that. So all of that is like, what is the stance? I often say perspective or point of view, but what is the stance that you're taking and how do we build the business, build the messaging, build all the content, around that.
Racheal Cook: Yes. And it took a very long time to land on these types of things, and I think that's something that sometimes as entrepreneurs, we tend to want things done yesterday and to have all the answers immediately. I feel like this is where the journey is part of it. Because you're going to have these moments of clarity where the message hits, the big idea, you know exactly what you want to be known for, but then sometimes you outgrow that. Your life has changed, your experiences have changed, or you're just tired of saying the same thing over and over again. And I feel like it almost starts to feel like you've outgrown your previous messaging. So what do you see with people when they're feeling that way? What are like the symptoms that they're outgrowing what they had previously built?
Jessica Sato: To me it feels almost like it's one of two things. Either it feels very grindy like, "Oh, this just doesn't feel good." It's like you're constantly tweaking things and trying to get it to feel right again. That could be like changing your offer a million times. It could be playing with a copy on your website. It could be a new lead magnet. I see a lot of people when they feel like, "Oh, the business isn't quite right. Oh, I think it's time for a rebrand." I see that a lot. And that could be part of it, right? But that exterior has to match the interior. So if you have essentially outgrown the thing that you've built, no amount of window dressing is actually going to make that work.
One of the examples I've used a lot that I think really resonates is sort of like being in a pot. Like you are a plant that's really root bound. You can't keep growing inside this same container that you built. So it's, how do I get back to the core and figure out, okay, what does my container actually need to look like? And I don't mean offer container, right? I mean like big business container that allows you to revisit. What is at the foundation of the business? And is it going to allow me to grow into whatever the next version of what the business needs to be? And I always try to get people to think more long-term than even just the next iteration. It's like, okay, what is this thing that we're building? Is it meant to last? What is it doing in the world? I believe very strongly that business should be a force for good. Is all of that coming together and allowing you to build into the space that you actually want to create.
Racheal Cook: I love that you brought this up, that it's not just rebranding or re-messaging to where you are currently. It's looking further ahead. Because I also see this challenge for some folks, and they don't do this deeper work, this kind of excavating of like, where am I really going? And that level of clarity. And instead they end up doing this huge project. Reworking all the copy, reworking everything on their website. Reworking offers. Just to feel like six months later, as soon as the website goes live, like, okay, I am already done with this. I see that a lot.
Jessica Sato: I mean, I've done that. And like sometimes tinkering small, sometimes going, like you said, big overhaul, but then looking back at it and thinking, okay, this is not where it's at. I really do think we do have to get more internal to that. And the other thing that's interesting about this work is I think a lot of people think it's optional. If I just do these other things right, then I'll get there as opposed to, okay, actually I do need to push the pause button to a degree and get back to what it is that we're trying to do. So that's I think probably been the most interesting part of this work is like, not so much convincing people that it's important, but that this is actually the thing you have to do in order to move forward into whatever the next evolution is meant to be.
Racheal Cook: It's almost like you have to remember that there are no shortcuts in this process, even though sometimes we really want there to be, especially when we're feeling out of alignment and the business results start to show that. Because usually if we're out of alignment, we stop showing up, we stop bringing in the type of clients we want, like other things will go wrong in the business. So it can often feel really frustrating when we tell people, yeah, like, you've got to slow down and pause and do this deep work. That feels really, really challenging to people.
Jessica Sato: Well, yeah, because I think in the moment you think, "Oh, that couldn't possibly be it," or again, like, "nice to have" or, "okay, I wish I had that kind of time, but I don't, I've got to," especially if the business has slowed down, right? Like if your pipeline is sort of dried up, if you're not getting those kind of clients that you really want to be working with or just that grindy feeling that we get. It can feel like, "Oh, if I just do this, it will fix things." And then you do that and then it doesn't, and on and on. It's almost like you hit this point where you're like, okay, literally nothing is working. This is my last resort and I really want people to not get to the last resort because by that point, they're exhausted. They're so frustrated. It's like the thing that they fell in love with when they were building this business is like now kind of just doesn't feel as good anymore.
So my encouragement is just push the pause button and do an actual evaluation, some kind of audit or something that allows you to really take stock of, okay, what is not working in this business and why, just keep digging. Right? That's where having a really good thought partner, a mentor, coach, et cetera. I don't think this is the work that biz besties do together. I think this is like paid work quite honestly.
Racheal Cook: Yeah. And I think it's helpful to have somebody who knows what type of questions to ask to pull things out of you. I know when I've gone through this type of process, it's very much felt like therapy. Like you just keep going down a level deeper, a level deeper, and then you get to the root of whatever you're wanting to talk about and you're like, "Oh, I didn't realize that was kind of underneath." And that's the experience I've had doing any sort of messaging work like this. It takes a lot more introspection and a lot more layers deeper than you realize.
When you were going through some deep shifts within the collective and really even before the collective, when you were going through that, what was it for you that made you think, "Oh, I actually need to do this deeper work that we're talking about" as opposed to tinkering?
Racheal Cook: As opposed to tinkering? That is a great question. I feel like I've had a couple rounds of doing this deep work with a few different people, and each time I get something a little bit different out of it. The first time I went through all of this deep messaging and branding work was with my friend Sarah Omo Ashman. I'll shout her out. She did a huge rebranding process for me when I left the Yogipreneur brand and was starting to come under my own personal brand.
Really interesting to me because I'd worked with other copywriters before and this was when I realized that copywriters aren't the same as someone who's more of a messaging brand strategist. Because that's what we did. Like we had multiple sessions where she literally just interviewed me, pulled questions out of me. And that was really the first time I think I'd done a deeper level values work than I had before, because a lot of other values exercises I'd done were like from books and you know how it goes with values exercises. It's kind of like circle five values on this massive list of values and ta-da, there's your core values, but it didn't mean anything.
And that's when I started to understand like, "Oh, I do have some really strong core values of life before business and keeping things really simple and strategic." And that's because those were the things I was saying over and over again. And so that kind of hit for me.
The next round was when I knew I was going to shut down all of my courses that were like 12 week long courses and shift into this whole new container. And that for me was, like you said, I needed a bigger pot. I needed something I could really grow into and I needed something that would evolve with me in a way that felt really sustainable.
One of the challenges I had with the course model, and this, some of this is personal preference. Like there's nothing wrong with running an online course, but I'm a relationship person. And I want to know people, so I hated it when I would do an enrollment for what was Sweet Spot Strategy, my online course, and like only a third of the people I would get to know the rest of the time. I'd be like messaging people like, "Hey, I want to check in. I can't believe you just signed up for this and never logged in or reached out to me." And so I wanted to attract the type of clients who wanted a relationship. Not clients who were kind of course hopping and I didn't want to just be a Dropbox addition to all of those things kind of kept adding up and that led me to where we are with the CEO Collective. And as you've seen, because you've been with us for a few years, it's always evolving a little bit. Because I'm always integrating and taking what I'm hearing from people and bringing that into the conversation.
Jessica Sato: I love that. And I ask that question because I do think it's really important for people to hear, like, you don't have to be in crisis. Right? I'm guessing none of those were like true crisis points. It was more like you said in one case, "I needed to shift into a completely different business." Another time it was like, "Okay, this doesn't feel as good as I want it to feel." So that's why it's like you don't have to wait until we're in crisis mode. You actually can be very strategic and do this work to set yourself up for success. So that, like you said, it's sustainable, it's repeatable, it's really tied into those core values. And then from there, it's like everything sort of gets evolved.
I just think a lot about, and this is one of the things I love about the CEO Collective, is like, we're actually like living the values of this organization and the people who are a part of it believe in these same things. Right? That's the beauty. When you're very clear on your values, on your stance, on your perspective, the right people come to you.
Racheal Cook: I started my business when I was like 27, 28. And I think the first business, anybody starts the first website, the first photo shoot, like there's a lot of like second guessing yourself and like this is what it should, it's almost like you're pretending to be a persona that you've created. And so I felt that a lot with my original brand, the Yogipreneur. Not that I wasn't, love the yoga world, had run a yoga studio, was a yoga teacher on top of all my corporate background, it just, I was trying to squeeze myself into what I thought other people needed me to be in order to be the face of that brand. And so for me now being in my early forties, this is the most me the brand has ever felt.
I think this is also something, maybe it's just the joy of hitting the stage of life and not caring what people think about you anymore. We have this really strong conditioning and socializing to fit in and to be what other people want us to be. Sometimes that people pleaser tendency or like, "my brand needs to look like this because everyone else is wearing jeans in a blazer or everyone else is wearing," remember the hats. I think if you're going to stand out and have a business that's truly aligned, it means you've got to finally get comfortable with yourself.
Jessica Sato: Yeah. And that's where the work is, right? I had a very similar journey. I started my business in 2012. I did that iteration of it for about eight years. Then I joined forces with a business partner and we did that for a couple years and we parted ways and now I'm doing this and even this has evolved over the course of time and there have been some critical inflection points similar to yours where I had to essentially push the pause button. I mean, yes, the business was still going, but I was doing that deep work in order to figure out where am I really trying to go? Like what am I actually trying to create in the world, and is this thing that I have right now going to allow me to do it? When you're in the midst of the evolution, you're not going to get there. And that's why it is, I think going back to figure out values, really what is that big vision that you have for your life, for your business? All of that is the work.
Racheal Cook: And I think that's something that's really hard when you're first starting out in business. You're just absolutely too close to the startup stage. It starts to happen once you're five or 10 or more years in kind of in that midlife of business, right? And then you start to think further. Like I've been thinking ahead about, okay, what is this going to look like as I'm in my fifties and sixties? How do I want this to continue or not continue? Would this be sellable? And I think that really changes the way you think about your business. Because now you're thinking about the legacy you want this business to be and the impact you want it to make. And that's very different from, "I'm just going to do this so that I can leave corporate." Right. "I just need to make my salary back." Right? Correct.
Well, now that you're talking to people who are kind of in this, you know, messy midlife of business, let's say, now that they're thinking bigger and wanting to figure out what is the impact they're trying to make, what are you seeing? Like what gets in the way of figuring this out for folks?
Jessica Sato: Well, one thing for sure is when things are good enough. It's really hard to do the work. I mean, it doesn't feel as compelling. Like I said, it feels like a nice to do, nice to have. And it's sort of like, if it's not broke, don't fix it kind of thing. Sure. But at some point you do get to that place where just nothing feels good. So I would say for sure a lot of people are at that stage where things are okay enough and they kind of are still stuck in tinkering. I see that a lot.
And I think the other thing too is, I find that people are, they're kind of at that point where they're not quite ready to think like big legacy, right? It still feels premature, like, "Oh, that's too heavy to do this kind of work" and I have tried to talk about this more in the, what are we building in the world? Not like big legacy capital L, but like, what are you building toward? So, like you said at the beginning, it doesn't have to be like this next phase, let's think a little bit more strategically longer term. And let's start putting the pieces in motion. Because in order to get to big Legacy, right, that there's some stages that you're going to go through that are still quite far especially if you're in this middle age space, mid forties kind of thing. But yeah, I would say some of it feels too daunting. Some of it feels like, okay, things are good enough, I'm not going to rock the boat.
Racheal Cook: I definitely hear you on that, and I think what's interesting is I think some of us are really like our natural desire for growth, personal growth, not just growth of the business. I would say for, in my mind, there's a massive difference between chasing like revenue growth for the sake of growth versus people who are internally motivated to grow as a human. And those are the people who get frustrated. Because I'm like that too. Like we get frustrated when that complacency starts to come in and we're like, not that we're bored. Because I never believe in like throwing a dopamine bomb in your business because you're bored. Like go get a hobby. But when you're really feeling that this doesn't fit anymore, this is no longer lighting me up, I'm not looking forward to this work. I don't really want to talk about these things anymore. That is usually to me where I think those who are growth oriented, like we're evolving all the time, and I know some people aren't like that all the time, but I do think it's the growth oriented, the people who love finding that new level in themselves and they love making those new connections internally. I think those are the ones who need to press pause and dig deep when it's time.
Jessica Sato: Yeah. I think that's right, and especially because if you are in that growth orientation, in the way you described it, and I agree with you, it doesn't have to necessarily be revenue, right? If you're a leader. And sometimes, if people have a love hate relationship with the term thought leader, but I think there's something to it. If you are in that space where you're really trying to change something in the industry, or even if it's just in your corner of the industry to shift a perspective, to invite people into a new, a new way of thinking, that is naturally going to evolve as you, as the leader grow and evolve.
If we have that really strong firm foundation of this is where I stand, these are my values, it actually makes that process easier because you actually understand the width or the depth of how far you can take this idea. And it's as you're talking about it, as you're shifting, as you're bringing people into those conversations, it just like, it gives everything a longer runway so that people can actually do something with that and so then you don't have to constantly be going back to the core work. You're just continuing to evolve, but it's still rooted in something really strong and clear.
Racheal Cook: I love that. I think this is such an interesting conversation and I hope those that are listening to it, if you're feeling this way and going back to that analogy of like you've outgrown your pot, something's out of alignment, you know there's something deeper, bigger, probably more meaningful to you that you want to figure out, don't hesitate to press pause.
You're taking some folks on a trip to Egypt soon. Talk about impact and legacy.
Jessica Sato: Yeah. The long and short of it is I grew up there, I studied abroad. I speak Arabic. And a couple years ago I had this dream of - you know, the only thing that really came to me in the dream was Egyptian Women Entrepreneur Initiative. I had no idea what that meant, but I started digging a little, trying to figure out what could this look like? But it was very nebulous and I also recognized like this was not, kind of to your point earlier, this is not an idea that you can just force. This is something that needed to evolve.
And earlier this year, it's been a very crazy year and I was looking at my business and I just thought, what would it be like if I were to really go all in on this idea if I brought a group of American or Western female entrepreneurs who are impact oriented, who are really thinking along the lines of what we've been talking about, like kind of what am I building in the world? Is it meant to last? And we put that against the backdrop of ancient Egypt. And we also did this in relationship with other Egyptian women entrepreneurs. And I honestly wasn't sure like, was that a thing? Is that something people would actually be interested in?
But surprisingly, so many people have really leaned into the idea of tourism and all the things that Egypt has to offer, which is amazing. Some rest and relaxation, but more importantly, the interaction between them and other Egyptian women recognizing like, yeah, we're part of this global sisterhood. We all are struggling with the same problems. The question that we're going to be exploring is, what are we building and is it meant to last? And we'll do that against the backdrop of ancient Egypt and all this juicy goodness, I can't wait.
Racheal Cook: I love it. I truly believe that travel is one of the best ways to reshape, rediscover yourself and your identity. It has changed so much for me personally. One of the biggest things that I think sometimes we don't give ourselves permission to do. I know I've gotten stuck in the, well, the kids and the life and the house and the pets and like I don't have time, but taking time to get out of the day to day if you're needing to think bigger and think differently and get out of the four walls of your office. These are the types of things that it might seem like a lot to say yes to, but I always come back from these types of experiences just feeling like totally changed because I have changed. You change your perspective so much when you get out of your day to day and try something new. And make yourself uncomfortable a little bit is also part of that. You have to be willing without doubt to rumble with the discomfort.
Jessica Sato: Well, and for some people, Egypt is a bucket list place for many people, it's a little bit like entrepreneurship. There's a glorification of this place. But Egypt can actually be a little bit of a hard place to be. It's very populated. It's a developing country. It comes with a lot of moments where you're like, you do have to wrestle with, okay, that did not go to plan, and you can do as much as you can in order to set yourself up for success. But at the end of the day, it's in those moments, like how do you meet the moment and whether that's here in the US as an entrepreneur, on a trip, as an entrepreneur, there's a lot to be learned about who you are as a leader, how you show up and deal with conflict or frustrations, and then all of that gets channeled into the business.
So I'm super excited. I'm actually heading there in about a month to kind of do a lot of groundwork laying and just to check the path and the sort of the pace. So it's not too much. And then we will launch the retreat sometime early October, I think.
Racheal Cook: Amazing. Well, Jess, as we start to wrap up our conversation, you've been a part of the CEO Collective for a couple years now. I'd love to ask you first, what does being the CEO mean to you?
Jessica Sato: This is such a good question, and we talk about this a lot. I mean, for me, it means really having the autonomy and the responsibility. I feel like they go hand in hand of building the kind of business I actually want. To me it has given me permission to actually claim that in a way that, I think I was dabbling before, it was like, yeah, I'm a practitioner, I'm a doer in the business. This has allowed me to kind of pull myself outside of the business and really think about what am I creating.
Is this sustainable for me and for my family? I mean, my daughter is going to be going off to college in two years, and then we'll be empty nesters. We won't even be 50 yet. And it's like, okay, that next phase, do I want this business to look the way it looks right now? And I don't think I, I think I would have just kind of continued. For me, being the CEO means really being able to take that step back and be really strategic about what I'm building, and to also be responsible for what that's doing in my own life, but also in the world.
Racheal Cook: I love it. I love that answer and I love that is how it is showing up for you. It's taking on that self-responsibility and saying, I'm in control of my destiny here. I'm in control of what happens next.
Jessica Sato: Yeah.
Racheal Cook: I love that. And for anyone who's been considering joining us inside of the CEO Collective, what would you share with them has been the best part of your experience?
Jessica Sato: Well, I know everyone says the operating system and that is actually really powerful, like the CEO operating system, which if you've not heard about that, just listen to a couple episodes and you'll hear it. I think that coupled with what we were just talking about, like that strategic piece, that operating system has really given me some structure and rhythm and a way to really think about how am I actually running this business. I would say that has been really instrumental.
I think the other part is just the other women who are in there. I mean, we have got such a beautiful, rich community of. I was going to say like-minded, and I think that is partially true, but maybe it's more like valued where everyone does believe in a life first business people are really seeking a kinder more, just more equitable world and we all are approaching that in our own unique way, and so it feels a little bit like a mosaic or a little bit of a tapestry where we're just bringing all of our stuff together and supporting each other, to me, has been probably the most powerful piece of the whole thing.
Racheal Cook: A great reminder that you have to lead with your values and be very outspoken about them folks, because I love that. That's one of my favorite things is everybody's so different, but it's the through line of the values and the way that we're all showing up in these very different ways to try to build a better next iteration of the world that we're living in and that our kids are going to live in. I love that.
Well, thank you Jess, so much for joining me today. What's the best place for people to follow you and to learn more about your work?
Jessica Sato: Yeah, so I spend most of my time on LinkedIn. I'm at Jess Sato over there, or you can find me on Instagram, Jessica Sato coach. If you are looking for support, you can get all the deets on my website, jessicasato.com.
Racheal Cook: Perfect. We'll have that all linked up. Thank you so much for joining me. I know this is a big idea that has been kind of bubbling up for a while now, so I'm excited to see what happens next with it.
Jessica Sato: Thanks so much for having me.