Transcript Episode 29

Transcript Episode 29: Building a Business Strategically Using Instagram with Christina Galbato


Transcript Episode 29

Stephanie Skryzowski:  

Welcome to the 100 Degrees of Entrepreneurship Podcast, the show for purpose-driven entrepreneurs who want to get inspired to step outside of your comfort zone, expand it to your purpose and grow your business in a big way. 

I’m your host, Stephanie Skryzowski, a globe trotting CFO whose mission is to empower leaders to better understand their numbers to grow their impact and their income. Let’s dive in!

Hey friends, welcome back to the 100 Degrees of Entrepreneurship Podcast. I am your host, Stephanie Skryzowski, and I am excited to be here today with Cailen Ascher. Cailen is a soulful business coach with a three day workweek. A mom of two little girls and the creator of Success Made Simple Accelerator, a programme that helps women attract their first clients with one high ticket offer. 

Best known for helping our clients become 100k coaches. Cailen has been featured in Business Insider, Huffington Post, and Inspired Coach Magazine and has been interviewed on top of podcasts like Entrepreneur on Fire and She Means Business podcast, among many others. She’s also host of the soulful business show podcast which airs weekly. Her masterminds and teachings have helped thousands of women transform their lives and businesses with her proven strategies for working less, making more and living better. 

Cailen lives in Bucks County, Pennsylvania with her husband, two small daughters and a spunky dog named Olive. And we are going to share so much today about Cailen’s work, her journey, her programmes, and I will just give a quick shout out right now if you’d like to learn Cailen’s three step method for attracting soulmate clients Grab a seat for her upcoming masterclass at And we’ll put that all into the show notes for you to have all of that. 

But I just wanted to give you a quick little overview of what Cailen and I talked about today. And I’m really excited to share this episode with you because it’s not necessarily full of tactical, practical, use this spreadsheet by that software type things today, we’re really talking about honouring your own energy, and using that energy to help you make good decisions for your business and to help you build a business that feels really aligned with what you love and the way that you want your life to look like. 

Like me, Cailen has two young daughters at home, and she has maintained a three day workweek for years, meaning she’s got this balance between working on a business that is not only really profitable, but also something that she really loves, while also maintaining that dedicated time to spend time with her family with her two little girls and do lots of fun things. 

So I really love the balance that she brings to this episode and talking about some of the things that she’s done to help her get to where she is now. So without further ado, I will get started with my interview with Cailen Ascher. 

Hey, everybody, welcome back to the 100 degrees of entrepreneurship podcast. I are really excited to be here today with Cailen Ascher. And I’ll tell you a little bit about how I know Cailen in just a second. But Cailen, welcome!

Cailen Ascher:

Thanks so much, Stephanie. I’m so excited to be here with you!

Stephanie Skryzowski:  

So I’ve been following along with you on social media for years now. And so I feel like I’ve known you for years, we don’t actually know each other in person, but I was a guest on your podcast a couple years ago. And we’ve just sort of stayed on social media in touch over the years. But I love having connections with people like you that I feel like we’ve sort of followed similar paths, and we have like a sort of similar story. And so I’m just really excited to chat with you today about all that you do and how you serve women entrepreneurs.

Cailen Ascher:

it’s so nice to actually have a time to chat with you, because I feel like I’m in touch with you more than I probably am, because I’m just following all the goodness on social media.

Stephanie Skryzowski:  

Exactly! I know. That’s one of the good things. It’s like it brings us together in that way, even if we’re not actually talking to each other. So when I think of you, Cailen, I think of the three day workweek. And I feel like you have made yourself known in the online business space for this three day workweek, and that’s a dream I feel for a lot of people who are in corporate or who are moms that are managing businesses and trying to balance all the things. And I imagined that your journey didn’t start out with being an entrepreneur with a three day workweek. And so if it didn’t, what did that journey look like?

I’ve been an entrepreneur for a long time, but I didn’t step into my three day workweek until six years ago, six and a half years ago to be exact when my first daughter was born. And prior to that, honestly, it was just a long journey of self discovery. I was trying to figure out exactly what I wanted to be doing work-wise and how to energetically kind of get myself in a space where I thought it was possible, you know, the whole mindset piece, and then just figure out the practical action to take. 

Cailen Ascher:

So I went down a number of different roads, tried my hand in a number of different things, everything from interior design, to freelance writing to teaching yoga. And what I did accumulate in that time was a lot of life experience, a lot of do’s and don’ts in business. And throughout all of it, I was really educating myself and how to show up in the online space. 

I started my first blog back in 2008, when people were saying in the online world, they wanted to be bloggers, right. And I know there are still very successful bloggers out there. But that was like, the way to show up in the online world was like, be a blogger and get people to advertise on your blog, or you write, you know, paid posts and stuff like that. 

And so I gathered a lot of information, but I didn’t know quite how I was going to piece it all together. And then I found out I was pregnant with our first daughter, which is very exciting. But I was like, “What am I doing? How am I going to do this, once she’s born? Should I continue on in business at all?” And I took some time off, and I took about three months off after she was born to figure things out. And what I realised was that even though I wasn’t totally clear on what I wanted to be doing, or how I wanted to be doing it, I knew if I just gave up on this dream that I had of packaging up something within me and offering it to the world in a way that would be useful, that at some point down the road, I would regret it and that I would be a better mom for having gone for it and tried at the very least. And so I had this idea, all of a sudden, like dropped out of nowhere, one of those divine downloads, that I wanted a three day workweek. And it was almost ridiculous, because I still wasn’t totally sure what the business was going to look like or how I was going to serve people prior to her arrival – my daughter’s arrival. 

I was kind of hitting my stride in business advice, business strategy for yoga teachers in the yoga community because I had the business stuff kind of in the works. And then I got certified as a yoga instructor, but I didn’t know if that’s even what I wanted to continue doing. 

So I had this idea for the three day work week she arrived. And I just kind of stepped into it. And I thought about, “Okay, if I’m going to be working just three days a week, I’m going to make the highest and best use of my time.” And as I kind of embraced what felt right and good for me, things and opportunities and people just started lining up. At the time, I wouldn’t have maybe even had the words to say like I was in the flow. But that’s totally what it was where I made an aligned decision with a three day workweek. It felt really good in my body, I was vibing with that, it felt so right, and then I kind of fell upon the coaching world. 

And previously, I had never called myself a coach, I didn’t totally get what that space was, I didn’t feel acquainted with it. And I found a coach and I started following her. I was really inspired by her. I bought one of our programmes. And I started to see, “Hey, I could hold space like she does,” I could help other women because of my life experience at that point, seven years of trial and error in business and give them just a little bit that would help them on their journey – that would feel amazing for me. And I could totally do that in just three days a week. 

You know, if I’m thinking about coaching and charging slightly higher prices than I was previously and really owning my self-worth in that way. And it all started to land. And within that first year, stepping into my three day workweek, I started landing some of those high end clients. And then the next year, my second year as kind of my first full year really as a coach was my first six figure year in business. And so it felt like this amazing, magical thing I just cracked open for me that I made a choice that felt right for my family with this three day workweek. And then over the course of a year or so everything kind of just fell into place. It was the most in the flow that I had been probably ever up to that point. So it was pretty cool.

Stephanie Skryzowski:  

That’s amazing. I love how you sort of tapped into your own intuition and how things were feeling. And that just gave you the sense like, “Okay, this is the direction I want to go.” And I know that it’s really easy to overthink things a little bit too much. And I’m a very analytical person, as you might guess. And so I’m doing all the spreadsheets and all the analyses and sometimes you just need to like, go with how you’re feeling. 

Was there any moment in that journey that you felt was really outside of your comfort zone? Are you really scared or did this part of your journey just naturally play into what it became?

Cailen Ascher:

Honestly, I don’t feel like I had any of those real rock bottom fearful moments. I feel like a lot of that happened before. Then once I was in that space, I felt so much potential, so much possibility. And it’s not to say everything worked out, I remember, I started my three day work week to be really specific, I think it was February of 2015. And by the summer, I started landing those high end clients. So it took a number of months, but during that time, I really felt like I was putting a puzzle together like, “Okay, I want to be a coach. So I’m going to educate myself about how to do that, what that looks like, how to package up what I’m offering and all of that.” 

But I remember by that fall, I was making $3-, $4-, $5,000 a month, which was great and so exciting, but it didn’t feel consistent. And there was one month where I was like, I’m gonna make $10,000 this month. And I made half that or a third of that. And there was a moment that was like, “Oh, gosh, like, do I really have this figured out?” 

You know, it wasn’t all smooth sailing completely, but especially hindsight is 2020. Looking back at that journey, it was really leading me to a place where by February of the next year, I launched my coaching in a bigger way with the guidance of a private coach that I’ve been working with. And I had a $32,000 launch of that coaching. And that was even more money than I’d made in a previous year. And so that really boosted me for a while! 

I was feeling pretty good. My mindset got a huge uplevel. And since then, you know, my business has been a six figure business ever since it gave me a new kind of ground floor. Even though in January of that year, which was 2016, I made like $200. But then in February, I made $32,000. So there was still a bit of a roller coaster that I was navigating, but I could feel the momentum building and where I was going. And I think my trust in faith and flow in kind of that divine support was really getting curated. And I continued to develop it ever since I’m deeper and deeper levels. But that was the first time where I felt like, “Oh, things are supporting me in this. I’m not just out there doing it alone.” 

Stephanie Skryzowski:  

Mm-hmm! And I feel like one win like that – that’s a big win! And I feel like one win like that, like you said, can propel you into the next season. So that’s amazing. 

You mentioned you invested in a private coach. And obviously you have had thousands of women who have invested in you as their coach or working in your programmes. What do you think about that? I feel like I did a podcast episode a few months ago, I think that it was released, talking about the investments that I’ve made in my business over the years and one of the biggest ones for me, I don’t remember the percentage that I said. But aside from the team, the next biggest investment was in professional development for myself. And so that is coaching, that’s masterminds. 

What would you say to somebody who doesn’t feel like they have the money or that it’s worth it? I’m using air quotes or that there’s not an ROI. Because I know that investing in first a business coach and different masterminds over the years has catapulted me to levels that I 100% could not have gotten to myself. 

So what do you think about that? Is that something that you build into your own financial plans and budgets as well? 

Cailen Ascher:

Completely? Yes, I totalled up in the last six months or so, and I’ve spent nearly $100,000 on coaching in the last six years since I started my three day workweek. You know, it’s been a lot. I see it as an investment in the business and investment in myself. 

Now to be 100% transparent, it’s gonna feel funny me saying this because I am a coach. I don’t think anyone needs coaching. Like I don’t think anybody can’t do it by themselves. But what I think coaching does is, it is a catalyst for quicker growth, quicker expansion, gives you some shortcuts – and it’s a trade off. 

When you say I’m going to do this by myself, I’m not going to invest in outside support, you’re going to put in your time and your energy. When you invest in a coach? Yes, it’s time and energy, but a lesser amount because you’re balancing that out with a monetary investment and external support. And so I would never ever say to a woman you will not get where you need to go without investing in a coach, or you will not get there without investing in me. That’s not my sales pitch. That’s not what I think this is about. But I do think that coaching with the right person, someone who aligns with your values, with your lifestyle, with your business model can absolutely expedite that. 

And we have my entry level programme for our newbies, who are brand new, it’s often one of the first investments they’re making – it’s a 90-day programme. 

And what we’ve designed within that 90-day container is really to get you in those 90 days, where we see most people after a year or two on their own. And so that’s what coaching can do, it’s $1,000 for that programme, but you can make more progress in 90 days than you would in 12 to 24 months of just kind of gathering stuff on your own and trying to figure it out. And also, the mindset piece is huge, when you’re working with a coach, or you’re in a mastermind, and have been a part of a number of high level masterminds. It’s just a different support system, when you’re just alone with your own thoughts all day, it can be the Wild West. But when you have a group of successful women who think in this expansive way, it just lifts you up. Even when you’re maybe feeling a little unsure, it can boost you right back up, instead of sinking and sinking and sinking lower into that spiral of worry or fear or whatever it is. 

Stephanie Skryzowski:  

Yeah, I completely agree. And any masterminds that I have been part of, have helped me to think bigger than I ever think on my own. I would say, I don’t necessarily find myself naturally like a dreamer, but being part of masterminds and sort of with other people that have that really like high energy and vibration, and you feel that and it just has allowed me to think way bigger than I could have ever thought on my own for my business my life. It’s like so, so powerful, so definitely worth the money. So what does your business look like today? How do you serve women entrepreneurs today?

Cailen Ascher:

Yeah, so we have two programmes, we have an entry level programme, which is called Success Made Simple Accelerator™, that’s the one I was just speaking about. That’s for women, usually who are dreaming of starting a business. And they’ve kind of been sitting on that for a while or have been maybe trying things for a couple months, sometimes even say a couple of years, and they really haven’t hit any consistency with clients or money, and they can feel their mindset dipping to a place that they know they need some support to get out of. And so that programme is really great because it meets where they’re at and helps them over the course of those 90 days to really see significant progress. And we have women posting in there every day that they’re getting their first hired clients. These are clients paying them multiple 1000s of dollars for the work that they’re doing. And these are brand new online service providers, brand new coaches. 

And then the other programme that I have is my mastermind, it’s called Uplifted™. And this is really a space for more established entrepreneurs who are making a couple $1,000 a month, or maybe even up to $5,000 a month, but they haven’t hit that six figure level yet. And they feel that they’re kind of maxed out with their time, their energy, they feel like they’ve hit that income plateau. And they can’t totally see their way clearly to, “how am I going to make more money without putting in more time, without dedicating more energy, and effort to making this happen?” And so we really support them with, yes, the mindset but also the systems and strategies to streamline the business and grow it to that six-figure level, so that they really can show up like a CEO, instead of kind of this like scrappy solopreneur trying to hold it all together all the time. 

So those are our two main programmes that we have. So we’ve got something for the newbies and something for the more established women as well.

Stephanie Skryzowski:  

And are the women in your programmes? Are they drawn to this idea of a three day workweek as well? Is that part of the goals that they step into working with you? Because they’ve seen you do it very, very successfully over the years. So is that something that they’re doing? And are they moms as well?

Yes, a lot of them are moms… not all of them, but we definitely don’t exclude anyone who is not a mother. I do find that a lot of moms, especially with school-aged children, or even younger than school age, find a lot of support in our programmes. And we really do try to encourage them to create a schedule that feels right and good for them. 

Cailen Ascher:

Of course, the three day workweek is really appealing, but I also know that’s not going to work for everyone. And so what we do teach inside our programme, one of the many things is how to create a feel good schedule that makes sense for you, your business, and your lifestyle, and is a part time hour schedule. I don’t think I have any women who are working 40 plus hours a week on their business at this point. All of them come because they want to be working definitely less than 40 hours if not closer to around 20 hours a week.

Stephanie Skryzowski:  

I like that idea of creating a feel good schedule because for some people working Tuesday, Wednesday, Thursday – full days – that doesn’t really feel good. But I like the idea of building a schedule around what really works for you and your family, because everybody is so different. And I feel like that concept of balance looks so different for everyone as well. 

So when you think about balance, that’s like such a loaded word, and I know that, but what does that mean to you? You’ve got two young children as well, and a business and a husband and all the things. So when you think about balance for your life in your business, what is a good balance feel like for you?

That’s such a good question. Balance, for me, feels like time for the things I enjoy, the people I enjoy, and the work that I love, because I do really love my work. I am guilty of you know, it’s one of the things I find fun. Like, if I do have some free hours on a Friday, sometimes I actually want to work. And it’s not because I’m feeling pressured to where I’m like, “Oh, I have to do this in order to make money.” It’s just because I truly enjoy the work that I do. 

Cailen Ascher:

But balance is really about honouring my energy and valuing my time. And so I normally wrap up my workday around 330. That’s also when our girls are usually done with… they’re in camp right now or school. And I can tell if I push it past that point, I’m starting to get bleary eyed, I can feel kind of rushed. Even my computer slows down like things will start feeling harder. And I know that my tendency in those moments is to be like, I will make this work and push forward. But if I can recognise that and honour that and step back, that’s when I can bring myself back into balance. 

And so balance isn’t like the static thing that I’m like, “Okay, this is the perfect workweek. And I must live it this way, every single day, in order to achieve this,” it’s more like something that I come back to, and I circle back to. And so that means I build in time for me. I meditate every morning, I have that yoga background. So that’s really important to me. I try to get movement in every day and time for myself, and also feel like spending time with my girls. I don’t want to be that mom that they don’t see because she’s working all the time. But I also am okay with different moments where my husband’s like, “Hey, I’m gonna take them out,” because I have a call or I am working. And I think it’s healthy for them to see that part too, that I have this business, that’s a priority as well. 

And so balance is something that I try to find or curate by paying attention to how I’m feeling and how my energy is. And when I do that, I can find that peaceful, most of the time flows, not to say it’s perfect all the time. There’s stress in business and parenting and all the things like I have a real life. But I know that when I go to the pool with my girls in the afternoon, instead of powering through and getting some more work done, that I feel better. And so when you build that in and begin to validate it with your own experiences, it becomes easier to see that, “Hey, when I actually take time off and end the work day at five instead of seven, I feel better, I show up better, I’m more productive.” That’s not a word I use a lot but you are and things flow in a healthier way and actually support you instead of you feeling so like there’s so much resistance meeting you. 

Stephanie Skryzowski:  

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I keep coming back to that phrase of yours, “honouring your energy.” And I am very much I gotta power through because there’s not enough time because I have to do this and I have to do that. But there are some times like when I step out of that to-do list in my brain and I really think about how I feel. Sometimes I just feel like laying down, like sitting outside in the sunshine with a cold glass of water and just relaxing for a minute. 

And I’ve read a couple books this year. Let’s see what does that… A Happy Pocket Full of Money? Have you read that one? 

Cailen Ascher:

I have not. That’s a cute little title though. 

Stephanie Skryzowski:  

It is! It’s a cute title. But it goes into like this sort of existential concept of time. That time is unlimited. And the time is almost like… I’m completely butchering this, I’m sure but like that time is not real, basically. 

There’s a whole lot of science that talks about that as well. But thinking about that, and quieting that little voice in my head, that’s like, “there’s not enough time you have to do this.” And then honouring that energy. I feel like that combination has helped me so much to achieve balance as well. And just like you said, really listening to your body and listening to really what you need. And then for me combining that with, there is no time, there is plenty of time to get everything that you need to get done. You don’t have to live by this clock. I feel like it has been super powerful. And it’s like a practice, I feel like listening to an honouring that energy is a practice. I don’t know about you, if you feel like…

No! Completely. I remember it was before my first daughter was born and since then it’s been a good seven or eight years, and I had this moment where I was like, “I am choosing to rush.” That was the energy I had in my business. I just always felt a little anxious, a little rushed. There was that never enough time kind of thing where I always felt behind. And it was all sudden, like this thing clicked in my brain where I thought, “I’m choosing this, I’m choosing to rush through my life, through my day, to feel this anxiety, about not getting enough accomplished. I could change that choice!” You know, it was a weird moment where I suddenly de-identified from that thought. I wasn’t that thought any longer. I saw the separation and saw that I could choose something different. 

Cailen Ascher:

And I love reminding myself of like, having little affirmation throughout the day of like, “I have enough time, money and energy for all of my desires and priorities,” and if I’m  feeling really good, like “I have plenty of time, money and energy for all of my desires and priorities.” Little things like that really do make a difference? Because we can cut these deep grooves in our brain thinking a certain thought for so long, and it takes a while to repattern. Sometimes I’ll even set things I want to remember, like a calendar reminder on my phone. So it pops up as a daily reminder every day. Here’s this affirmation, you want to say. 

Stephanie Skryzowski:  

Yeah, oh my gosh, I love that. I’m gonna have to go back and listen to the affirmation, you just said, because that’s a really good one that I have enough time for all of my desires and priorities. That’s a really good one. So for somebody who is just kind of starting out on their journey. 

I know that we have a lot of clients who are, I would say, in the early stages of their entrepreneurial journey, I’ve got lots of friends that are there as well. What tips do you have for women who are just starting out and seeking to find that purpose in their work, as well as the balance with their families and their home life? Whether it’s like a practical tip or a mindset tip? What would you say to those women? I think especially that they are just starting out?

Cailen Ascher:

Yeah, I think the first thing I would say is that very few of us start out knowing exactly what we’re going to do. I think that was a misconception I held for a long time, I thought that the most successful people had it figured out from the beginning. And now I realise listening to lots of podcast episodes and things like that, reading lots of books, that people often have a journey to get to where they’re meant to go. And honestly, I don’t think I’ve reached my destination. I think there’s going to be many iterations beyond where I’m at and I’ve made peace with that. I’m okay with that. 

And so a lot of the women who join my programme, my new coaches, new service providers, they’re like, “I don’t know quite what my business is and I’m thinking about this or this,” and it’s like a slightly different version. And they’re so caught up in picking the right one that it keeps them paralysed and stuck. And, and there really isn’t a right choice or a wrong choice. There’s just one that maybe feels a little better, even if maybe your logical mind is saying that’s not as good of a choice because of XYZ. But just start somewhere, just choose something and commit. 

We had a woman who joined our programme, after four years of dreaming of her business, thinking about her business, and having the START-STOP energy, I think it was within her first month, if not the first couple of weeks, she landed her first client, because she finally just stepped into it. She just started! And I’m sure… I mean, it’s been about a year now since we worked with her. I’ve checked in a couple times and our business is doing great. But I’m sure as she develops, her business is shifting and growing. And we see that. I’ve seen that in myself. I’ve seen it in my friends and colleagues. 

And I think that’s just such an important reminder that you don’t have to have it 1,000% perfect, 1,000% clarity to begin, you can have 80% clarity and have 50% of it thought out and just begin and that’s why I think it’s so important to find support and I’m not saying you need to invest in a coach or a programme, but connect with a mentor, connect with a business buddy, someone who can hold you accountable, someone who you can chat With who kind of gets it. I know, for me, my family is super supportive. 

But some of them don’t totally understand what an online coach does. And they’re confused. And they still talk to me about interior design, even though I haven’t done that in a decade. “How’s that going?” and I’m like, “Well, that’s not quite what I do, but thanks for checking in.” But I think it’s so important to have a little bit of community around you, especially if you don’t feel like your family or your support system, in your real non-virtual life, totally understands what you’re doing. I think it’s really so vital to find some connection and community beyond just doing it yourself.

Stephanie Skryzowski:  

Yeah, you’re right. I think that’s so important. And like you said, it doesn’t need to be a paid coach, it can be a friend or somebody else in your network that you know that you can just like send, you know, I send Marco Polo messages, like the app – on my phone, and little videos, to some business friends of mine or my inbox. Like it doesn’t have to be anything formal or expensive. But having that person there that you know, is rooting for you. Because like you said, some families, maybe they’re not supportive, or they don’t understand, so knowing that you’ve got somebody on the other end of the phone that does is so so helpful. 

Cailen Ascher: 

And like you said, I just want to reiterate like, it doesn’t have to be something formal, if that’s not feeling right and good. Like I get on a call every Monday with two of my girlfriends, they both have online businesses, one’s a parenting coach, one does colour analysis. So different businesses got different things going on, all of us have two girls, you have two girls, it’s like the wave of the future. It’s so helpful just to get on and if I’m having a great day, they’re there to celebrate with me, and if I’m having kind of a low day, they’re there to listen and provide the right kind of support and feedback because they get it – they’re in the same kind of industry. So it’s really, really helpful. 

And then when the timing is right when you find that right coach or that right programme, and you’re having those like, “am I gonna do this butterflies in my stomach?” I think one of the best things you can do and I give this homework to my clients all the time when they’re on the fence about my mastermind, because it’s a multi $1,000 investment, is just do a body check. Is this feeling nervous? Excited, expansive? Like, holy cow. Am I gonna do this? This is so big. Am I ready? But like, it’s uplifting, like my mastermind – Uplifted™? Or is it? Oh, my gosh, this is scary. And this is heavy. And I’m not quite sure. 

And you can see me on camera, but like my body language changes with those two feelings. One is kind of like turning in, covering your heart and protecting yourself. And that’s your body’s way of like, ‘no, not right now, this isn’t the right thing.’ 

But scary doesn’t always mean bad. Sometimes scary is like you’re on the leading edge of your comfort zone about to break through. And it’s that final test to really get you in check, like how committed are you, and then you step into it. And so much goodness can unfold.

Stephanie Skryzowski:  

Yeah, that’s so powerful to just pay attention to the cues that your body is giving you. And I feel like when I say we I mean me often, we’re moving so quickly through life that we often don’t slow down enough to really listen to those signals that our body is giving us. And sometimes when you do slow down, it is crystal clear. Like you can make that decision with such clarity because your body’s already telling you the answer. So I love that!

Cailen Ascher:

It’s so true. And I think we’re kind of in a world where we’re taught to just think things through. But as women, we’re feeling beings. And so bringing the body into some of those decisions, like at least giving it a say, I think is really important. Instead of just trying to like logic, your way through everything with your pros and cons list, just do a body check to just be like, ‘how do I actually feel about this?’ Because your mind can convince you that one thing is the right decision or a wrong decision, when your body is telling you something very, very different. It’s just interesting to bring a little awareness to it. 

Stephanie Skryzowski:

Yeah, I like that a lot. So I like to ask this question to a lot of our guests because as you know, I’m a finance person. So I’d love to hear how different entrepreneurs manage their numbers in their business. And so you don’t have to give us any details or anything by any means. But how do you manage your numbers? What does that look like for you? And how does that really empower you to help you and your business?

Cailen Ascher:

Yeah, that’s a great question and one that I think is so important to have, because I think a lot of us, we can be a little awkward and uncomfortable talking about the management of our money that it’s sort of like, ‘Okay, well, it’s a hot mess. I don’t want to think about it,’ but I’m pretty organised. I mean, just like I like my organised schedule. I like my organised finances, or at least… probably not as organised as you, but organised to a degree that is useful to me. 

And so for a long time, I’ve been kind of just keeping my own books. I like doing that. I’m kind of reaching a point where I’m like, that’s probably not what I need to be doing anymore with my time. But it’s worked up until now, my husband actually is in banking. And so he is great when it comes to any tax stuff that we need organised. 

And in terms of just kind of my approach to money, what I love, and what I have my members of the mastermind learn is Profit First. So I’m sure you know that very well. I’m sure most of your listeners have heard you talk about it at some point. But that approach in that book by Mike Michalowicz is so, so useful. And something that I really love getting my women to do is pay themselves a paycheck, because a lot of them… the money just comes into the business and then the business spends the money, the business is in charge of all the money, and they don’t take. Even if they’re really bringing a nice amount of revenue, they’re not paying themselves. So they don’t feel like any of the money is like, really, theirs to use. And so I love having that. Even if it’s just a little account transfer, right, like a couple hundred bucks or a couple thousand bucks every month that goes from the business to them and pays them. 

I think that just shifts things in your mind that in a healthy way, it gives you some distance from your business. Because in the beginning, we can feel like we are our business and our self worth can be totally wrapped up in the business. And I’m speaking from personal experience here, and giving a little distance where the business is an entity and the business pays me that’s so healthy. 

And I think the management of the money, when the money is all complicated and confused and messy, it doesn’t make you feel empowered and successful. You feel like, “Ugh! I’ve got to sweep that under the rug and not let anybody know about it.” And so I think what you do in your work is so so important, Stephanie, because I think it’s something that a lot of women have shame around, and there’s no need, because we’re not really taught how to manage money. And we’re not really taught as entrepreneurs, especially how to manage our money, especially with the long term picture in mind. 

I actually just hosted a wealth workshop with my husband last week for our mastermind members, because we were recognising, “Okay, we’re teaching these women how to make money now. But we want them to be wealthy, moving forward, not just ‘oh, I can make a lot of money and then spend a lot of money right now.’ But how are we planting the seeds for the future.” And so that’s another piece that I bring in when I’m thinking about the money that I’m bringing in now, and how we’re managing it is also what we’re allocating for, for future – for retirement for our girls, or the things we want to create for ourselves in the future.

Stephanie Skryzowski:  

I love that. And I like that you have listed a number of goals that are outside of the I want to make six-figures, I want to make seven-figures. Because one thing that I talk about all the time is like “Well, why? Why do you want to make seven figures? Because that’s what the internet told you to do?” There has to be a deeper why behind that. And whether it’s retirement or saving for your children’s education or investment or real estate or whatever that might be like building that long term wealth strategy, it should be absolutely a part of your business goals. Because otherwise, a goal to hit seven figures or six figures is just hollow, like why am I hitting that? I don’t know. It doesn’t really drive you when there’s not really a purpose behind it. 

So I love that and love that you use Profit First and that you recommend paying yourself to all of the women that you work with. Because what I have seen is that you kind of start to resent your business if you’re not making any money, like personally. And so if your business isn’t paying you, you’re like, “Ugh! I’m spending so much time and money, and I’m not even getting compensated for this.” So I think that’s so important. I’m glad that you instil that in all the people that you work with.

Cailen Ascher:

Yeah, it is so important. And it shifts things. It really, it makes such a difference. You suddenly feel like a boss with a business. 

Stephanie Skryzowski:  

Exactly, exactly. Yeah, it’s not very boss-like to be making nothing. Yeah, totally, totally. Well, I’m just gonna wrap us up with a couple quick questions. So I would love to know what is your favourite book that you’ve read? And let’s say a nonfiction book doesn’t have to be business, so let’s say nonfiction.

Cailen Ascher:

Yeah. Recently, I have been loving the books by Tosha Silver. She has a book called Outrageous Openness, which it was the first one I read. And then I read another book called, It’s Not Your Money, which is really, really cool. And her approach, she’s got like a yoga background like I do. So a lot of the terms that she uses feel very familiar, but it’s basically about how to lean on universal support, divine support, in your life, in your business, in your finances. So you’re not feeling like such a lone wolf out there trying to do everything by yourself and leading so heavily from the ego, with like our wish list of demands and desires, but rather trusting that you’re right where you’re supposed to be. Trusting that life is bringing you opportunities that it’s meant for you. Trusting that the things that aren’t coming your way just aren’t meant for you. And just resting in that deep sense of trust. 

And honestly, her books, I tend to have occasional bouts of anxiety and things like that, especially when it comes to my business. And I have been like, mellow and chill. For the last couple months, reading your books. It’s been like a really, really nice little vacation, hopefully, permanent vacation from the energy I was living. And even though I’ve been doing spiritual work and energetic work and mindset work for years, this has taken it to a whole new level for me. So if anybody’s ready to go there to that deep trust, I highly recommend her work. 

Stephanie Skryzowski:

Oh, I’m definitely going to have to check that out. Thank you for that recommendation! I like to use our podcast guests to basically help me create a reading list for myself. Everybody has such good recommendations that I haven’t heard of before, so that’s my favorite part.

 Let’s see, I guess my last question is, where can people find you? Is there anything you want to share with our listeners or where is the best place to find you online?

Cailen Ascher:

Yeah, so you can always find me over at my website at, we’ve got lots of like, great resources and my podcast is over there. We’re kind of in transition right now, so depending on when you arrive at the home page, you’ll either have access to my 3-day workweek schedule download or we just created a new quiz, which kind of gives you your soul business archetype. Kinda like your inner makeup, are you a healer or are you nurturer or creative or a visionary… There are 6 different types that you can be. So, that’ll be something of a surprise there, but one thing that I know will be available is my masterclass, which is all about attracting high end clients with a single high ticket offer and you can find it at and we’ll make sure that’s available to everyone with the link. 

And in terms of social media, Instagram is where I’ve been hanging out. You can find me @cailen.ascher over there.

Stephanie Skryzowski:

Awesome! Thank you so much! Well, there is a lot to check out. I’m really excited to see this quiz when it goes out – very very cool. But Cailen thank you so much for sharing your time and your wisdom with me and with our listeners today. I really appreciate it. And I think there’s so many goals here, and I can’t wait… like I said I’m going to rewind and go back to that affirmation that you said earlier and that’s going up on my whiteboard. 

Cailen Ascher:

I love it! Yeah, thank you, Stephanie. I’m so honored to be invited to be a guest and it was so much fun catching up with you!

Stephanie Skryzowski:

Thanks for listening to the 100 degrees of entrepreneurship podcast. To access our show notes and bonus content, visit Make sure to snap a screenshot on your phone of this episode and tag me on instagram @stephanie.skry and I’ll be sure to share. Thanks for being here friends, and I’ll see you next time!

Transcript Episode 29

@stephanie.skry Episode 29 podcast blog