In short
Podcast Summary: The Thoughtful Entrepreneur - Episode 2271
Episode Overview Title: Creating High-Value Group Coaching Programs That Attract Premium Clients Host: Josh Elledge Guest: Cailen Ascher, Founder of Success Made Simple Duration: Approximately 15-25 minutes
In this episode, Josh Elledge interviews Cailen Ascher to discuss her transition from one-on-one coaching to creating scalable and profitable group coaching programs. Cailen shares her insights on developing high-value group offers, pricing strategies, and attracting clients ready to invest in their growth.
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Key Concepts and Discussions
Why Group Coaching Works
- Time Freedom: Cailen transitioned to group coaching to reclaim her time as a new mom, moving from multiple one-on-one sessions to managing group sessions, thus significantly increasing her efficiency.
- Increased Income Potential: Group programs allow coaches to serve more clients simultaneously without increasing their working hours.
- Peer Learning and Community: Group dynamics foster accountability and deeper transformation compared to individual coaching.
Transitioning Strategies
- Audit Existing Practices: Coaches should evaluate their one-on-one offerings to identify which tasks and content can be systematized for a group setting.
- Define Transformational Outcomes: Establish a clear transformation intention for clients and create a framework that can address multiple client needs simultaneously.
- Intentional Program Design: A well-structured program is crucial for scaling while maintaining quality and client satisfaction.
About Cailen Ascher
- Cailen Ascher is a business coach specializing in helping coaches, consultants, and service providers transition to profitable group programs.
- Focuses on efficiency, leverage, and tangible client transformation.
About Success Made Simple
- A coaching platform aimed at helping entrepreneurs streamline processes and design programs that enhance income while granting freedom.
- Offers actionable strategies and systems for faster client results.
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Episode Highlights
- Transitioning from 1:1 coaching to group programs.
- Designing scalable and transformational group offers.
- Effective pricing strategies for high-value group programs.
- Attracting clients who are committed to investing in their growth.
- Creating a business model that supports personal freedom and lifestyle.
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Conclusion Cailen Ascher emphasizes that scaling a coaching business through group programs can lead to greater impact, increased income, and personal freedom without compromising the quality of client experiences. Coaches are encouraged to reflect on their existing practices and client needs to develop transformative group offerings.
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Links Mentioned in This Episode
- [Success Made Simple](https://successmadesimple.com)
- [Cailen Ascher LinkedIn](https://www.linkedin.com/company/cailen-ascher---calm-biz/)
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Additional Information
- For Entrepreneurs: Interested individuals can apply to be featured on *The Thoughtful Entrepreneur* via [Up My Influence](https://UpMyInfluence.com/guest/).
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- Podcast Launching: Resources available for launching your own podcast via [Up My Influence](https://go.upmyinfluence.com/podcast-guest).
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This episode encourages entrepreneurs to rethink traditional coaching models and explore the benefits of group programs for both their businesses and personal lives.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:04Well, hey, Thoughtful Leader. Welcome to the Thoughtful Entrepreneur. On this show, I interview purpose-driven founders, experts, and change makers who are making a real impact in the world. Want to be a guest? Simple. Go to upmyinfluence.com and click podcast. I'd love to promote your story to our audience of over 100 ,000 and across over 2 ,300 daily episodes and counting. Want to get booked on other great shows like this? Simple. Go to podverified.com and get your free guest authority score. Thousands of hosts are looking for high quality guests and Podverified connects you the right way. Now let's dive into today's episode.
0:58With us right now, it is Kalen Asher. Kaylin, you're a business coach and founder of Success Made Simple. You are found on the web at KaylinAsher.com. Kaylin, thank you for joining us. Oh, thanks so much for having me, Josh. I'm happy to be here. Yeah. So, hey, before we get going and talking about what Success Made Simple is and the work that you do, the impact you have in the world, what have you been doing for fun lately outside of work and, you know, kind of the typical mom duties and that sort of thing? Yeah, well, as we record this, it is the middle of summer. So we are navigating the summer schedule.
1:35I've got a 10-year-old and an 8-year-old. Some days they're at camp, some days not. So we're spending a lot of time at the pool in our backyard. My work days are looking very different right now. And in a couple of weeks, we're heading up to our lake house where we're going to fully unplug. It is my happy place. Go paddle boarding and just do some hiking. It's going to be magical. Yeah. What kind of lake? Is it like a chain of lakes or just what? What kind of lake environment is it? Yeah, it's up in the Berkshires in Massachusetts in the middle of the mountains. And it's a smaller lake. It's called Stockbridge Bowl.
2:06And it's so peaceful and quiet. Oh, that's got to be great. Yeah, for anyone who's grown up in a lake environment, I was raised in West Michigan and lakes everywhere. We had family members that lived on lakes. And boy, what great memories. So parents listening, get your kid out to the lake. if you can find one near you. You know, unfortunately, I live in Florida now. And that's the one thing they tell you when you move here is stay out of the lakes. Those are not swimming lakes. They have brain-eating amoeba, apparently, and gators. So we let them, the brain-eating amoeba and the gators kind of rule the lakes here.
2:49Yeah, stick to the ocean. All right. So, Kalen, talk about the work that you do. And by the way, to our friend that's listening, you can follow along. Just go to KaylinAsher.com. We have the link in the show notes so you kind of see what's going on. And Kaylin, I regretted to mention, or I didn't mention, you are also the host of the Soulful Business Show, a podcast. So to our friend listening, you can search around. You can find that show. Yeah, thanks so much. So I'm a business coach. I've been a business coach for about a decade. I work primarily with women and some amazing men who are really looking for a way to shift their work in a more leveraged, scalable format.
3:31When I first started as a business coach, I was doing one-on-one coaching and was also a new mom. And I realized I was just taking up all of my time and energy and I was creating a job for myself. And I really sat with, you know, who do I want to be as a business owner, as a visionary, as a CEO? and I shifted into a group model of coaching and it shifted everything in my business. So now I work with experts, professionals, coaches to create group programs. So they are not stuck in that one-on-one or done for you model trading time for money. Okay, so what types of, like where is group work appropriate and who might not be a good fit?
4:12Can you help us define what a great group offer might be? Yeah, absolutely. And this is something that comes up a lot when you're working with clients because they're like, well, I've been doing one-on-one. Does it really translate into the group model? And the truth is a lot of times it does need to shift. If you're doing highly customizable programs or offers or deliverables, you might need to shift a little bit and either empower your clients to learn how to do the work you're doing on their own or shift your model so it's more high level or create an environment where you're bringing in, you know, coaches and experts alongside you and more of an agency model to support people in that way.
4:53So it's, it does require often a little bit of a shift, but the benefit that you receive, I went from, you know, having 10, 15 client calls a week to one call with all of my high level clients, I got, you know, 90 % of my time back. And so it's really worth exploring if you're feeling that, that time crunch and you sort of hit that plateau where you can't grow anymore and you're not willing to put in more time or you just don't have the time to put in. Yeah. Okay. Well, so what would be examples of program? And I want to make sure that I delineate this because not, maybe not all client personas may be appropriate for groups.
5:38So for example, you know, what we've learned with our clients historically, what we've been working with for the past five and a half, six years is, you know, they're, they're running pretty significant companies. You know, they're high six, low seven figure is kind of pretty common And it's pretty challenging to get them to step into a group, depending on what the format is. I find that masterminds or connecting with other high-level leaders is valuable at that level. But it's a lot less kind of guide on the side as opposed to sage on the stage kind of group coaching. Do you mind maybe just defining a little bit more about thinking about our friend who's listening, who might want to consider starting a group of some sort based on their expertise and who might want to make some of those changes or pivots?
6:36Yeah, absolutely. So you're absolutely right. I think the group model works particularly well for if your client base are at sort of an entry level or a mid level. Absolutely. Those very advanced clients do want those masterminds or those VIP containers where they're working really closely with the expert. And so what I've found, you know, with my clients is that when they are like, for example, if there's if they're a health coach and I've worked with a number of health coaches over the years, they sort of hit a place where if they're specialized maybe in gut health, they're like, you know, I am prescribing this same regimen for client after client after client.
7:17And it's not really tapping their expertise. It's not really tapping their creativity. They're like, you know what? I could create a program where it addresses this specific need within my niche and move people who require that information into that program and then open up space to work with people who need that more high-touch customizable program. Or if they need a little break from that, just lift it out altogether and have that group be their signature offer. Yeah. So when you're working with a client, how do you step in? What do you help them do that it might be a little bit more challenging for them to figure out and do for themselves?
7:57I mean, because it seems like on the outside, anyone might be able to say, okay, I'm just going to offer a group program. Okay, yay. Where are you helping them? Yeah, absolutely. That's a great question. And that's sort of how I started my first group. I was like, hey, I think I'll group instead. And then I realized like, oh, it would have been really useful if I had a framework for this process. So where we come in is we audit what you're doing right now. What does your work look like? How are you working with your clients? What might need to shift or change and what can stay? So we sort of high level understand what's the transformation we're trying to get here so that as we look at what is your signature framework, what is that curriculum that we're going to be building out and what's the structure of the program?
8:45You know, a lot of people come in and they think, oh, well, the longer the program, the more valuable it is. But in truth and where I'm at in my business, I'm like, well, if I could get the results I want in 60 days instead of six months. I don't really care if the price point's the same, if I can get that deliverable in 60 days. So, you know, just re kind of quest making them question, what are some of their preconceived notions of what a group needs to look like? So they can create a container that's really transformative for their clients, but also make sense for themselves so that they get to show up as the expert that they are and make sure it makes sense in the context of their lifestyle too, because that's a really big component of what we're working with our clients.
9:28We want them to shift into a business model that supports and enhances their life, doesn't detract from it. Kaylin, can you talk a little bit about the numbers and the business model and kind of, you know, what price points are we talking about? And like, how does all of this work out into, because I know you work with a lot of, maybe a little earlier stage folks and helping them to create a kind of a stable or consistent six-figure income. So can you talk maybe about how the numbers generally end up working on a group coaching program? Yeah, absolutely. So what we recommend to start sort of as a price anchor is$1 ,000 per month of your program.
10:10So if it's three months, it starts at$3 ,000. If it's five months, it's around$5 ,000. That's not to say it can't be higher, but we really want to challenge people to not think of a group as like a membership where it's 50 bucks a month or$100 a month. We want them to really create a container that feels high touch, even if we're really being smart and systematic about what those touch points are. So when we're looking at that, let's say we help them create a $5 ,000 program and they're looking to make$100 ,000 over the year, then that would require 20 enrollments. So we're not necessarily talking about, oh, now we need to find a thousand people for this group program.
10:52These numbers can be fairly small, especially if you're stepping into that high ticket price point of, you know, 20 clients, maybe even 10 clients. If you're doing a really, you know, high level mastermind, that's$25 ,000. These can bring in six, multiple six, even seven figures as you embrace that group container. And how does one go about attracting the type of clients that are going to be willing to pay those price points. Absolutely. So, I mean, it's always wonderful to think about problems that your clients are already having so that you're not necessarily creating a brand new niche or a brand new needing to tap a brand new client.
11:33I know a lot of your listeners are established business owners. So reflecting on who are their clients and what are the needs of those clients so you can meet them inside that group container. So when it came in my case, when I shifted from one-on-one to a group model, it was because so many of my clients were showing up and talking to me about, I have a three-day work week. And they were saying, I would love a three-day work week. How do you make your schedule work when you're a busy mom and a business owner and all of these pieces? And I thought, you know what? I'm going to solve this three-day work week problem for them inside a group container.
12:08And so there was already buy-in and there was already interest because they were literally asking for it. And so I think it's really important to reflect on, like, what are your clients already asking for? And if you can create a really transformational offer that gets them that result and provides the pathway for that transformation, it's going to be an easy yes for them, even if it is, you know, a high ticket price point, so to speak. Yeah. And one final thing I'd love, Kaylin, to kind of get your perspective on. I think a three-day workweek sounds really nice for some folks. And I can say that, you know, I don't have a three-day workweek, but I generally only schedule appointments on Tuesday, Wednesday, Thursdays, and Fridays.
12:58I generally, you know, again, it's just all like internal stuff. So, and I really try to give myself more than just two off days over the course of a week. And I can tell you that I am just that for me, and there's a lot of evidence about the four day work week, I think a three day work week even sounds better. But can you maybe just address this concept of a three-day work week? A, why? Well, you already talked about how it's possible, but what are the benefits of this or why might that be enough? Yeah. Well, I mean, to go back into history, just for a beat, the five-day, 40-hour work week started during the Industrial Revolution because they determined that a man of working age, a 30-year-old male had 40 good labor hours in him per week to do physical labor.
13:53So it is tied not at all to our current workforce or the way we currently work. So it's just such an antiquated process. But the reason it worked for me and how I found it was as I stepped into motherhood, it was just the season of life that I was in. And I thought, you know what would be amazing if I could figure out how to do my work, my business in three days and then have four day weekends so I could be a present mom with my kiddos. So I think it solved a problem for me in my lifestyle was like, okay, well, we need less child care. And I get to be there for those moments when they're growing up.
14:32And so I don't necessarily prescribe a three-day work week for every single business owner, no matter where you are or what you do. But I do think it's really important to reflect on what would feel good, because I don't think we ask that question enough. And what would make sense? And so maybe it's four full days and a half day on Friday. So you start your weekend at lunchtime on Friday instead of at 6 p.m. We can make these little changes and modifications to move more fully into alignment. And what I've found is the more intentional I become about the hours I work and the container in which I work, the more efficient I am, the more people respect my boundaries.
15:16You know, I've had clients where they're like, you only work three days a week. How do you, you know, fit it all in? And it's like, well, it just naturally kind of the puzzle pieces land as they need to, because I'm, I'm an integrity and, you know, living my values. Yeah. And, and there really is something to be said for honoring boundaries, whether it's with clients, team members, I mean, really anybody, right? And not feeling this pressure that in order for us to be successful, you just have to clock more hours at work. That's not true. You can absolutely be way more efficient. And certainly there are a lot of great tools to help speed up what we can do now with, you know, AI-enabled tools.
16:06And then we can also surround ourselves with really smart people who can help us shorten the learning curve. So we're not spending, you know, 80, 100 hours working on something that turned out to be not very fruitful. Well, you know, a guide could have helped you with that. So kind of part of the value. All right, Kalen, for our friend that's listening and they would like to learn more about what you teach, what you do, where can folks kind of dig into that a little bit more? Yeah, so right on my website, you'll see on the homepage, you don't have to scroll, there is a free training all about how to make$100 ,000 or more a year with one Zoom call a week.
16:50That's kind of our clever way of saying group program, right? Going from all the client calls to that singular call. And so that's available. If you're curious, if this sparked some interest in you, that would be a great place to start. It's about 20 minutes, pretty quick, quick watch. Nice. Kaylin Asher, your website, kaylinasher.com. And you've got some great resources directly on the website. I was going through your praise page as well. But certainly you can click on the free workshop, get the free training, and you can see, you'll break it all down for them, Kalen. Well, Kalen, it's been a great conversation.
17:29Thank you so much. Anything else? Did we miss anything else? You know, I think we covered a lot in our 15 minutes. I feel good. Great, great. Kalen Asher, again, the founder, your business coach, your personal website, kalenasher.com. Thanks, Kalen. Thanks, Josh.
17:49If you've enjoyed this conversation, I'd love to invite you to share your message with the world at podverified.com, where thousands of podcast hosts and thoughtful guests are connecting the right way. Podverified helps match you with the right stages for your level of authority. No more wasting time on brand new shows that just aren't a fit. Your guest authority score is free. And so are your first two podcast matches. Come hang out with me there. I'd love to learn more about your business, support your mission, and help promote you far and wide. Just head to www.podverified.com to get started.
18:33And of course, if you'd like to be a guest right here on The Thoughtful Entrepreneur, just go to upmyinfluence.com and click on podcast. Thanks for being a part of this movement. We rise by lifting others.
From the publisher
Feeling stuck trading time for money as a coach or consultant? In this episode, Josh Elledge interviews Cailen Ascher, founder of Success Made Simple, to explore how she transitioned from one-on-one coaching to scalable, high-impact group programs. Cailen shares actionable strategies to create transformational group offers, price them for profit, and attract clients ready to invest—all while reclaiming your time and building a business that supports your lifestyle.
Why Group Coaching Works
Cailen’s shift to group programs was driven by a need for freedom and flexibility as a new mom. One-on-one coaching required constant client calls, leaving little time for family or personal pursuits. By designing group programs, she was able to serve more clients in less time, reclaiming 90% of her schedule while still delivering real results.
Group programs also increase income potential without requiring more hours. With a structured curriculum, coaches can generate six- or seven-figure revenue while providing deeper transformation for participants. Peer learning, accountability, and community dynamics make group programs more impactful than individual coaching alone.
To make the transition successful, Cailen recommends auditing your current 1:1 work. Identify tasks and content that can be systematized, define the transformation you provide, and design a framework that works for multiple clients simultaneously. Intentional program design is the key to scaling without sacrificing quality or client experience.
About Cailen Ascher
Cailen Ascher is a business coach and founder of Success Made Simple. She helps coaches, consultants, and service providers move from time-intensive one-on-one work to profitable group programs, emphasizing efficiency, leverage, and client transformation.
About Success Made Simple
Success Made Simple is a coaching and training platform dedicated to helping entrepreneurs scale their businesses, streamline their processes, and design programs that generate both income and freedom. The company focuses on actionable strategies, systems, and support to help clients achieve results faster.
Links Mentioned in This Episode
Key Episode Highlights
- How to transition from 1:1 coaching to group programs
- Designing transformational group offers that scale
- Pricing strategies for profit without compromising results
- Attracting high-commitment clients with outcome-driven messaging
- Creating a business model that supports lifestyle freedom
Conclusion
Cailen Ascher’s insights demonstrate that scaling your coaching business doesn’t mean sacrificing quality or client results. By leveraging group programs, coaches can achieve greater impact, increased income, and more personal freedom—all while delivering meaningful transformation to clients.
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