393. We Spent 3 Days With Entrepreneurs Worth Over $100M - Here’s What We Learned…
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Just a quick note to let you guys know that we will now be releasing episodes on Thursdays and Saturdays instead of Tuesdays and Thursdays. We've noticed that so many of you listen more on those days and so we're going to release the episodes accordingly. We'll do it as a test and see how it goes. I'm always open to feedback if you want to drop me a DM at IamNatalie. But yeah, the episodes will now be Thursdays and Saturdays.

Welcome back to the Boss Babe Podcast. Okay, today we're going to talk all about some of our biggest takeaways from being in our CEO Mama $100 million room. And we were talking about wanting to do this because I think it's always really important anytime I get back from any kind of mastermind, I'm like,

I always want to bring everyone else into the fold. Like even if you weren't there, I want you to feel like you have a seat at the table. So just for this episode, Lindsay and I were going through what our biggest takeaways were and we'll talk through them and just really open it up so you still feel like you were there even if you weren't. So Lindsay, you want to kick us off? Yeah, I love this conversation because I feel like the...

A lot of people are so secretive about their masterminds and they gatekeep and they, you know, it's like until you're in, you won't know what's going on in the room. And we're the total opposite. It's like every time I sit in those rooms, I get full body tingles of like, this is so incredible. And, um,

The, the energy in here and just the, the humans like they're just real humble people who have figured out ways to be successful, not without their troubles and obstacles but yeah so we really wanted to share so yeah I think you know my my biggest takeaway, we were talking before we press record.

Just on you and I personally in our like life is going to life situations that are happening. And I think that's really my biggest takeaway of being in these rooms with super successful women that have huge followings and have built really, really successful businesses is.

Life is still going to life. Like they, there is no one and no level of success that makes you immune from hard shit happening and hard shit happening in the periphery to the business. Yeah. In the business too. Like people quit or a launch doesn't go well, or like something happens in the business you have to deal with. But I'm talking about in the periphery of life and you around the business where I don't think there's a single woman that's ever been in any of our rooms that has

not had something happen personally or in their relationship or with their health where it threw them for a loop and it threatened the business because they were taken offline. Their nervous system was taken offline and that they had to find their way back. And the ones of those who, you know, during the mastermind were currently in something like that, I think that was some of the most epic moments

impactful conversations that we had was when someone was like, I don't really need business advice, but like this is happening with my home situation and my childcare and it's throwing me for a complete loop or like this is happening in my relationship and it is so distracting. I can't, I, I don't care about my business right now or I'm having this health thing happen and I'm scared to death and I kind of just want to set the whole business aside while I go on a healing journey with my health. And so,

And I think it's important from the outside looking in when you look at really successful people to know they are not without the life is going to life situations. And I think what differentiates really successful people and then the benefit of being in rooms like that is

as soon as something like that happens, you have this place to come and you can be completely transparent and vulnerable and say, this is having my relationship or this is happening with my health. And it's really scary. It's really distracting. I can't say this publicly because I don't want to freak my team out or I don't want to freak my clients out, but I need help. Do you guys have a resource for this thing in my marriage or this thing in my health or this thing in my money or my family? And then watching everyone else in the room be like, girl, I went through this too. And here's what I did. Here's the person you need to talk to. Um,

and the generosity and the openness of people who are like, let me help, you know, like we, we want you to be okay. So I think that's my biggest one is, is just watching humanity and, and the, the, the sisterhood aspect of it, you know, of like, I just want you to be okay. I don't even care about how much money you make or how you can help me in my business. I just want to know you're okay as a human. I really agree with that. And I do think it's really important for,

people to have that kind of space to go because like you said this is one of the few places where they can be really vulnerable and open you know they have these huge online followings or are very well known in their industries and might not feel comfortable just dropping into a random facebook group or a mastermind that they think is going to be filled with their own clients i know i've had that too sometimes where i've joined something and it's a lot of clients that i work with and for me you know i still want to hold that professionalism so i can totally see that

that's one of the only places they can be. And to go and just get the answer that you need and have that full confidentiality, which is something that we make everyone agree to when they come on board is really important. And I think also it goes into the real curation element of all of these groups. I think curation is incredibly important because if you just let anyone in and you don't know how, you know, in integrity they are, you don't know, you know, what's their experience in the past with masterminds,

then I think that can cause problems. You want to have people in that group who are genuinely supportive of other people, who are willing to do their own work in rooms like that, who are willing to show up and be vulnerable and also commit to being confidential. I think all of those things are really important. And there's only been probably one instance where we had a feeling of, I don't think this person would be an amazing fit. And we kind of overlooked it.

And instantly we were like, okay, we need to take the application acceptance back because we just knew this kind of thing can affect the entire group. And it might sound like a you can't sit with us kind of vibe. That's not what it is at all. But we take it really seriously when someone trusts us enough to bring their really intimate

personal and professional challenges to the table that we won't just let anyone in. So that is really, really important. And there's definitely been, you know, comments in the past about how hard it is to get in to see your mama. And I really think that's what makes it so good, though, is, you know, when you're in the room, you can trust being in the room. Yeah. And I think those of us and people listening, if you've ever been in a room where you felt like

you couldn't tell the truth you know exactly what we're talking about and I've been in those rooms where I'm like I feel like I need to sugarcoat something or I need to kind of dance around what's really happening and like make it sound less bad or like better because I don't want I don't want to look like I don't belong here or I can't handle this by myself or I don't want to like

feel shame for needing support on something that's not business related if I'm in a business mastermind. And I think that's something, especially with CEO Mama, and I think that's just inherent to a mastermind that's for women who are mothers. Of course, a lot of what we do is business focused. And I mean, we can talk about it, but one of the takeaways of being in that room is

people apply what we talk about. They apply the business advice and then they have like multimillion dollar launches and they've never gone above low six figures. And all of a sudden they're making a million dollars on a launch or they apply a system and then they can work part time or, you know, like we have real tangible business advice results in there too. But I think, yeah,

We set the expectation with the program up front that it is just as much about your life and your humanity and your nervous system and your motherhood as it is about your business. And I think sometimes I can sound fluffy coming in. They're like, oh, yeah, well, that's great, but I'm still here for my funnels. And then when we look at all of our feedback forms and stuff after retreats and people who are cohorts that have completed, 95% of the feedback is like, yeah, the business advice

changed my life. But the much bigger, deeper impact was the people I met and the lifelong friendships and the feeling of being able to come into a room and express stuff that I have not said to anybody else about how, you know, life is lifing or, um,

And to feel no judgment and that I'm completely safe here. Nobody's going to put up a reel or a story that's like, did you know that this I can't mention her name, but she's in a mastermind with me. Like, I don't know about you, but like I've been in those rooms before. People would have like sidebar conversations publicly about like what they're hearing in their mastermind. And I'm just like, oh, I never want to feel like.

build a room or host a room that doesn't feel safe to be in. Yeah, there's something too that I've noticed since the first ever retreat we did with CEO Mama. We can teach something on the business side. So we always teach the most cutting edge funnel and digital marketing strategy, like very cutting edge and it's very direct. Implement this, it will work, like very, very direct. We can give that piece of advice

And do no nervous system work. And that advice will probably not get implemented. Or get implemented the way in which. Is going to get results. Or we can give that advice. We can do deep nervous system regulation.

and we can integrate and that advice goes and gets implemented on such an expert level. That's what always blows my mind because I just feel like the strategy without that regulation and deep work never really translates the way people want it to. I think that's something that knowing it now and seeing the direct results of it, like seeing the wealth that that kind of strategy has created and like we're not the kind of mastermind that shares these screenshots.

You know, that's just important to us. But seeing the wealth that it has been able to create really has me realize I will not do it without the nervous system regulation and anything I do moving forward. It's really, really, really important. Yeah. So what's your biggest takeaway? Is it that or is it something else? No, mine is different. So

One thing I was going to mention is, yes, they hit their biggest financial milestones they've ever hit. However, I feel like they do it in a different way. So my biggest takeaway from being in these rooms is these women are sick of scaling for scaling's sake. And sometimes they're not even aware that they do it until they kind of say it out loud and we dig into it deep and we ask a lot of the questions. And before you know it, they realize they're scaling for scaling's sake.

And the profits going down, the stress levels are going up, the team size is getting bigger, they're getting further and further away from doing the thing that they're really good at or they enjoy. And when we dig into why, like, why are you doing this? Most of the time, the answer comes back.

I don't know. I thought this was what I should be doing. And I thought it was going to make me happier. And I thought it was going to give me more freedom. And actually, it's done the opposite. And there's a lot to be said for that. Because yes, all of that is true. And it doesn't mean that when you're not scaling for scaling's sake, you're making less money or you're capping your wealth. That's not the case at all. And I think we've been able to demonstrate that really deeply at Boss Babe with the way that we have changed things up in the last couple of years. Our numbers have never looked better.

But it's very intentional. And I do think it takes a lot of the inner work to be able to run the business like that and to make those kind of decisions. But whenever someone is scaling for scaling sake, they are so deeply unhappy because it feels unaligned. And I will say, you know, the women in this room, they aren't building VC-backed companies and most of them aren't building businesses they're going to exit. Yes, we have had women and do have women in the room that have had nine-figure exits or

you know have had that but it's not necessarily the reason that they are doing the business that they're doing now they're in these kind of rooms because they're wanting that level of freedom with abundance but the freedom

And so I always get really excited when I can dive into someone's business and help them hit those huge, abundant wealth and freedom goals, but without doing it in this like templated, blueprinted way. Like, let's dig into what you want. How do you want your life to look? And I just realized a lot of people don't believe that they can put out, here's the money that I want to take home. Like, here's the exact number and here's how I want to spend my time.

They don't realize they can be really intentional about those two things. And there's always a way to reverse engineer it to make it happen. And that's the one thing that I get so excited about in these rooms is when we are doing spot coaching and I ask those questions and we're able to reverse engineer a way that they could do it. That makes me feel really happy because you just know it impacts them on every single level, their relationship,

Their motherhood, their health, everything is impacted so positively by them changing and doing it that way versus the typical, I did this because I think I should and eventually I'm going to have this and it's chaotic and it's exhausting and they're sitting in these rooms saying,

I've built something that on the outside looks absolutely incredible, but honestly, I feel like burning it down. And I'm always the first to raise my hand saying, I've been there and I walked away from my entire company. Let me tell you what I would have done differently and what I have done differently. And I like being able to give that perspective. Yeah. And I feel like some of it is,

how do I say this? It's like almost like they need permission to think differently. It's not like they need permission to do something different because they're bosses. Like they run businesses. It's not like anybody in there needs permission to do what they want, but it's almost like they...

they get into the room and then they ask the question and there's this sense of permission to hear other perspectives and kind of surrender to it almost to say, Oh, maybe that would work for me in a way where perhaps in the past they're closed off to the idea that that model or that reverse engineering answer would even work for them. You know, people who have never done webinars or never launched group programs or never done one-on-one and, and,

You know, we're challenging them to look at all these options and and they're like, oh, well, I've never thought that that would even work for my business, you know, and and so it's not necessarily permission to do what they already know that they want to do, but it's also permission to apply different things and and.

different models into your business. And I relate to that so much in my past entrepreneurial stuff, because it's like, well, I'm already down this path. I got to just keep going down this path. And this, you know, I've built this type of business. This is the only model that will work for me. And then you come into those rooms and you hear kind of the lateral moves or the kind of out of the box way other people are running their businesses. And you're like, wait,

Maybe that would work for me. And then we get the real tactical support from not only you, you know, and the marketing expertise that you give in those coaching, those one-on-one coaching sessions, but also like,

other people in the room going, I did that and here's how it worked. This is, you know, I applied this, I used this tool. And so you just get massive transformation so quickly. And I think the other part of that that I wrote down is, is you said it, it was the intention. And I think that's the other thing that is so interesting in those rooms is watching people come in with one intention and leave with a different one. Like, and you said it, but I think it, it,

warrant saying again, which is a lot of people come into those rooms with the straight up intention of business growth. Like I want to grow the business. I want to hit this milestone and investing in this mastermind is going to help me hit this milestone. And then they sit through a few sessions. They hear other people get coaching. We're in those mastermind sessions. And all of a sudden you can see the intention shift to going, wait a second,

maybe the number isn't why I'm here. It's like, I want to grow, but I want it to be enough. Or I want to actually, I don't even care about the top line number. I just want to be doing less of everything in the business. I want to learn to delegate or I want to systematize this thing or I want to put this on evergreen so that I work less, but make the same amount of money. And I think

I love those moments where you see someone's brain switch in those coaching sessions and they're like, oh, maybe I don't need a seven-figure business. Maybe I need a high six-figure business with a couple delegated team members at high profit margin and me only working half as much, you know? So I...

permission and intention, I think are, are subtleties that you touched on that I think are also really prevalent in the room that would be hard to, like, I don't know how we put that on a sales page, but I think once you get in the room, it's like, Oh, being around other people who are, who have, or maybe a little bit ahead of you or who have made kind of confronting decisions in their business gives me the sense of permission to think differently about how I would reverse engineer into a different outcome. Um, and nothing is off the table. Like

I can do anything I want in my business. I'm not locked into a previous model. Agree. And I also, I love watching the shift when people let go of the sunk cost fallacy, like you said, they've gone so far down this path or they feel like they're stuck to this path.

and the realization that, wait a minute, I am the boss. And I had my own realization around this, but wait, I am the boss. I get to decide. Like what we would throw suggestions out and it would be, I can't, there's no way I can make that work. That wouldn't. And then all of a sudden something clicks and they're like, holy shit, I'm the boss. Like I get to actually decide. I get to change things up and this all gets to start with me.

And I think when you have built a big business and you have a lot of clients and you have a lot of team, it's really easy to like get caught up in feeling on the hook for everybody else. Brendan Burchard always says this to me, but he says the tail doesn't wag the dog. So when the tail wags the dog, it means that like your team is actually dominating the situation. The usual roles are reversed.

But he's like, the tail doesn't wag the dog. The dog wags the tail. And what he always means by that is he never, and I see this firsthand, he never ever lets his team stress him out or push things on him that feel misaligned. He refuses to have stress in, like bad stress in his business. And that's how, and whenever his team start wagging the tail, he's

he's able to switch it out and has awareness around that. And he says, he always says, if you want longevity in business, this is something you have to figure out. And it's something that he said to me numerous times. And sometimes it takes a while to land because I have all these excuses of, you know, I can't because of this and I'm on the hook for this. And what about this? I've committed to this. And he's always like, remember,

The tail does not wag the dog. And it's such, at first, a mindset shift. Then it's something you can execute. But again, it comes back to the mindset stuff, the inner work. That part's really important if you want to make the changes on the outer world. It makes me think, as you're saying that, I'm like, ooh, it makes me think of a conversation you had with James Wedmore a few weeks ago around fear and fear.

And how fear also starts to be the tail that wags the dog. Like if you start operating in your business from a sense of fear, you're making decisions in your business for some future outcome that you'd actually don't want. But now that's what's driving you. And so, yeah, now the fear tail is wagging the dog.

And the dog is starting to go down the path of telling the universe, okay, well, now I'm making decisions based on this fear outcome. The universe is like, okay, fear outcome. That's what we should give you. And you end up down this path of like, this isn't the business I wanted. It's not making the money I want it to make. I'm working way harder than I want to be making. And it's making motherhood feel hard. It's making relationship feel hard. It's making my body whack out, you know, and it all kind of comes back.

to, in that moment of like, yeah, is the tail wagging the dog? Like, are you, whether it's team or, or perception, external perception or fear, making you make decisions in your business in a way that you know, intuitively are not the right decision for the business, but you're doing it out of one of these other metrics, you know? And I think that's something I do feel like that's something that

in a nuanced way, almost every conversation in those CEO Mama mastermind sessions comes back to is like, what's, what do you really want? Like, what's the truth here? When you cut through the team member who wants this or the clients that are asking for this or the fear outcome you're trying to avoid in your business or your life, when you back up one more step and you're like, Hey, okay, this stop wagging the tail. Like, what does the dog want today? Like, what do you actually want?

And I feel like what we've created in these rooms, and this is like the core of this conversation, is we've got to create safety in this room for a woman who is a CEO and a mama.

most of them are breadwinners. Most of them are, have been ambitious women from the day they were born. We have to create the safe space for them to be like, you know what I really want is this thing or this or less of this or more of that. And the emotions come out and like, God, how many of us have cried in those rooms? Right? Like every time we have to create the safety in the room for the truth to come out. And usually when the truth comes out now, we can actually help people. And that's when the reverse engineering is this light bulb moment. Cause it's like,

Okay, if the truth is that you don't want to do six launches a year and you don't want to do all these things, like then let's find a way for you to make the income that you need with one launch a year. Here's how we would do that. Or if you don't want to do this program anymore, but it's the main revenue generator in your business. Okay, great. You don't want to do it anymore. That's totally okay. Let's figure out a way for you to generate equivalent revenue with other offers in your business. Okay.

Or like, you don't want to have a big team, but you've hired a bunch of people. Okay. Not the end of the world. We can find a way for you to let people go and, and build, you know, restructure the business in a way that is graceful and feels good for everybody. Like, and those are all real conversations we've had. Right. And it, but it took the person getting to this moment of like, actually the, the truth is here's what I want. And can you guys help me with this thing? And I just think like,

I haven't been in a lot of rooms where I felt safe to tell the truth. And I think that's the biggest thing that we've done with CEO mama is with everything we've already talked about with, with the acknowledgement that life is going to life with this acknowledgement that like, we don't want you to scale for scale sake. Like we want you to scale if that's really what you want. And this acknowledgement of like, we're here for, to have real permission, permissive conversations. Like anything can come up. You can tell us the truth about anything and we'll help you. Um,

And I just think that's what's rare. And then you take the step back and you're like, damn, and this is a $100 million room. Like most of these retreats, when we get 20 or 30 of the women in the room together and you total up just the annual revenue of their businesses, we're over 100 million. And it's like, okay, this is the microcosm of the future of business that you and I are after, right? It's like we want women who are influencing business like the women in this room are to

to have to feel like they can tell the truth and they can come in and they can sit in here and say here's what's really happening in my life or my business and here's the support I need with it and not be judged and not be told that not gaslighted you know like oh you should just keep going like why would you throw that thing away they can come in and feel really held and I think that's that's why I do it that's why I wanted to be a part of it from the very beginning is like

There's nothing else like this. There's nowhere else like this that feels this safe to be truthful and honest. And not only can I just be truthful and honest, but I get honest, truthful, supportive advice and

ongoing support back yeah oh it's whenever we're interviewing women to come in a lot of time we hear you know i'm just i don't know something isn't feeling right right now i can't put my finger on it i don't know what it is and it's almost like when they walk into the retreats we like give them truth serum because all of a sudden they get to the root of it and they're like oh this thing i've been sitting with for two years i've got it now i understand it and i also just want to call out too

Just because the answer to, for a lot of these women might be scaling down, doesn't mean their revenue goes down, doesn't mean their profit goes down. But it's expanding to that conversation of you can create massive abundance and your revenue and your profits can grow, but you can do it in a way that actually gives you more freedom versus less. Because I don't know about you, but I've also been

and masterminds and programs where, you know, anyone can give out a quick, get rich quick strategy that's going to work.

And I've done that. But on the back end, the amount of chaos and stress and time it takes to be able to maintain what you implemented or deliver what you implemented is really freaking challenging. And I never wanted that to be what we do in See Your Mama because, like we said, these women are holding a lot for their entire family, for their teams, for their clients, and

we don't just want to throw something out there so that we can get the screenshot saying look at the money I made that's not what this is about that's why we don't share the income screenshot but we do it in a way where we get to the truth of what would work for them and then share this you know the cutting edge strategies but in a way that's not going to increase the load that they're carrying and so it doesn't have to mean doing less means earning less it doesn't have to mean that and

I think we're testament to that. The women in there are testament to that. And that's something that I really want to get across in this podcast for anyone listening who is feeling like the Lord is getting bigger and bigger.

And we often do upper limits exercises that we work through. And I remember when I was scaling from seven figures to multiple seven figures, I did an upper limits exercise. And in my head, you know, I was like, no, there's nothing stopping me. Like, there's no fear I have about scaling to multiple seven figures at all. Like, I'm ready. And when I really, really dug into it, the fear that I had was that it was going to be so much more work.

And I had to really overcome that to know that was another way of doing things to then feel really comfortable to scale. So that's really what I want to get through in this and that you are the boss. You get to decide how you do this. Yeah, I think that's the perfect summary of it. And I think you and I ultimately, one of the reasons we love CEO Mama specifically and why we at this point anyway, like we reserve everything.

that type of room, we're curating it specifically for mothers right now, is that both of us in becoming mothers, that felt really hard, you know, to stay in that mindset and be a mother where

it is so self-sacrificing, you know, and, and that's a whole other conversation, but it, it rewires you to be so oriented to self-sacrifice it. Cause in those early motherhood years, that's what's required for the most part. And, and I think there's this extra level of support and care and nourishment that we really wanted to bring to mothers. Cause we didn't have it. Right. And we felt the impacts of that in those early days where it's like, Hey, you

your business is the first baby that you had, but it's, it's not the only one and it's not the most important. And so as you grow your heart and your empathy and, and your life outside of your business and becoming a mother, how, how can we take some of that nourishment and that nurturing and that softer energy and come back into the business and go, what if I looked at this with like a whole different motherly mothering lens? And I was softer on myself and I was, um,

I cared more about the experience everyone is having of me in this moment. And I cared that my, my motherly nervous system being regulated regulates my child's nervous system. So surely my CEO nervous system being regulated regulates the nervous system of the business. And like, and I think you and I make those parallels a lot privately and it's, it's like, okay, how do we do this work now? And, and,

and help more mothers like us feel like, oh yeah, I can, I can soften. I don't have to ride so hard into the business all the time and burn myself out and have this hypervigilance. And like, you know, I've been talking about like addiction to work and how so many of us are like literally addicted to our businesses because it's just how we're wired. And, and before we were mothers, that, that was our hobby. That was our passion. That was everything to us. And now we're mothers and we're like, oh, this addiction actually kind of feels like,

not so good sometimes. And how do we change that? And I think it is this like softening and the calmness that we're trying to cultivate as mothers, because it's so important to our babies, like how to bring that calmness back into the business and make decisions and have these conversations in a different state of mind. And I think we've done that really well. And I think the group of humans that are in CEO Mama,

reflect that type of work. Like everyone is deep in that work. And I think it shows in their businesses, it shows in their lives, it shows in how they help each other, even outside of the mastermind and the friendships that they develop. Like, yeah, that, that piece of it, I think is so important to me and why as we keep doing it and we'll preserve and protect that aspect of it is like, this is a safe place to come and have a calm nervous system and look at your business and

in an anti-hustle way, you know, and it's not that no one in there is scaling. There's a lot of people scaling, but they, they are doing it so intentionally without that like rigid edgy hustle feel. Yeah. With a regulated nervous system. I love that. Um, and I think we can also do a full episode on work addiction. I think that would be really interesting. So let's, let's mark that one. Okay. I love this. This was so fun to dive into. Yeah. Yeah.

Same. Let's go prop the work addiction one and do that one next. Okay. Sounds good. Okay. Follow us for more. Yes. Work addiction. Bye everyone. Bye.

Okay, if you loved this episode and you're also really interested in joining us in CEO Mama, applications are actually open for our August enrollment. So if you're interested, drop me a personal note on my Instagram at IamNatalie and tell me a little bit about you and your business and I can put you in the right direction, but I would love to get to know you first. So that's my Instagram at IamNatalie and we can chat about it and I'll let you know whether I think it would be a good fit for you.