From Stuck Expert to Thriving Mastermind: Ashley Ebert’s Business Breakthrough
25 Mar 2025 · 22 min
This is a podcast episode titled "From Stuck Expert to Thriving Mastermind: Ashley Ebert’s Business Breakthrough" recorded in 2025. It features Julie Chenell hosting a conversation with Ashley Ebert and Kathy, discussing Ashley's entrepreneurial journey, challenges in marketing, the development of her mastermind program, and the impact of coaching and community on her business growth. The episode provides insights into scaling service-based businesses, webinar marketing, and building mastermind groups.
Welcome to Million Dollar Grit, the podcast that dives deep into the world of entrepreneurship, where tenacity meets strategy and dreams meet reality. My name is Julie, and I explore the raw, often overlooked truths of what it takes to succeed in business and in life. It's not just about the glossy success stories. It's about the grit it takes to get there.
Hey, everyone, this is Julie from Million Dollar Grit. And today I am not going to monologue. Today I have my dear friend and client Ashley Ebert here to talk all about her business, her growth, her diving into webinars, all that good stuff. So, Ashley, thanks so much for being here with me today.
I mean, I'm excited. Million Dollar Grit, best podcast ever. Just happy to be here.
Oh, thank you. All right, so let's just dive right in. I want you to tell my listeners about, just briefly, your business, your niche, the problem you solve, and who you help.
Yeah. So I first became an entrepreneur when I was 23. Started a wedding planning business with the idea to, like, you know, do a coup weddings here and there. It exploded. And it's actually, we have seven locations, a team of 30 planners. We do a million dollars a year in business there. And then a lot of people were like, how are you doing this? And I'm like, well, let me show you. So I'm just very candid about behind the scenes and scaling wedding businesses. So now I own that company fully still. And I own a company called the Abundance Group, where we have a mastermind and I get to coach one on one wedding professionals that have, you know, hit the 100k mark, but want to get to being in the owner's seat in their business.
Yeah. Awesome.
Well, first of all, congratulations. It's not the easiest thing in the world to scale a service based wedding business.
Very true. It's very true. Especially through Covid. Let's just be honest.
Like, oh my gosh.
Yeah, I. I told my husband, I was like, you know, good wife, good mother on my gravestone. No, I'd rather have got a wedding planning company through Covid. Like that. That's like my claim to fame.
So naturally, people wanted to know what you were doing, which is why you began the Abundance Group, which was inspired by the success that you had, because lots of other service based businesses want to know how to do the same thing.
Right. And I feel like creatives kind of give themselves. They. They don't give themselves enough credit and they think, oh, I'm just a creative or I'm just a florist or I'm just A planner or whatever, but I really help them think more strategically and. And have their business be aligned in alignment with their. The life they want to have. Not just to have a job they love, but a life they love, too.
Yeah. Awesome.
All right, let's take everyone to the point at which we started working together. So Kathy and I were doing. We were doing a Disney retreat, which you are a Disney die hard, just like me.
I am.
And so she. So Ashley came on the retreat. We got to know each other, hit it off right away. What do you remember? Like, what was the moment where you were like, I really think I need some more personalized help. Like, what problem were you facing? Or what triggered that? Sort of. I think I need to get some support.
I remember it vividly. I have a. I actually sent my girlfriend, Sarah Dunn, a video of the exact point in Disney where I have this moment, which is so funny. So the biggest challenge I had is for the first eight years, it was like, I knew the content was great, but. And we talk about this all the time at Moxart. I am a coach and a cheerleader. I am not a great marketer. I'm trying to flip that script. But for me, it's really, like, I love and I have such a passion for the community, but I don't necessarily think in that market forward way. And so it's like, you know, I would see all these coaches that were great marketers, but maybe not great at the strategy that we're getting all of this traction. And it was really kind of upsetting for me of like, I know, because, again, I've built it. I. We do a million a year. Like, I have the receipts, but, you know, I don't show up on Instagram or TikTok or all these things. And so it was like, okay. It kind of coalesced with being in Disney with you guys. Kathy and I were friends on Facebook, which is how I heard about all the amazing things y' all do. And we were sitting. I don't know if you won't remember this. Probably. I do. I think about it probably once a week. We were sitting. Because y' all did a VIP tour.
Yeah.
With. With the retreat. You spoil us rotten. And we were sitting in the lawn where the fireworks show is. We were eating Casey's hot dogs, and I. I moved kind of sat next to you and A.C. and I was like, julie, help. And you were like, tell me all the things. And you obviously, like, we got to know each other over the couple days we were together, and you're like, this is it. Like, let's do this. Let's, let's. I want to coach you personally. And I was kind of like, oh, my God, I'm sweating. Oh my gosh. Okay, let's do it. But it was, it is, it's such actually a fun memory because we were just at Disney last week and I walked by and I was like, that's the spot right there where Julie and I connected on her being kind of my coach. Because again, your brilliance is, and I say it all the time, that you are one of the best marketers on the planet. Again, you have the receipts for that. And so for me to be able to tap into that, to know I have the strategy, to know I have the connection side, the community side, the community building side, but that I missed that. And it's. Now I just kind of get to tether into you any time. And sometimes you're like, do it like this. And I'm like, I'm not even going to ask why because I'm just going to do it that way. And that, that shortcut is. It's been game changing for my business. I mean, you know how much my business is last year and it's just been. I absolutely could not have done it without that moment and without you kind of just there whenever I needed.
So I want to bring up something you said that I think is really impactful and is something that we can, A lot, a lot of people can relate to. You said, I have the receip, but sometimes I just am not good at marketing or getting myself out there. And there are other people who don't necessarily have the receipts or don't necessarily have the chops that you have, but they're so good at marketing that they're attracting all these people. And that sort of. It's not jealousy, it's more just like, damn it, what am I doing? Like, I have the answers, I have the receipts, I have the way I can help people. But, like, people don't know that I'm around. And I think that you describe that really well because that's, that's a very classic problem with experts.
When I think too, you always tell me, stop thinking like an expert. I was like, oh, okay, I'm supposed to be marketing. I gotta make it sexy. I gotta make it, you know, whatever. But I think the other thing is there's this layer of tension that I constantly deal with as kind of more in the expert lane is I also want my marketing to have deep integrity.
Yes, yes.
And so sometimes the really sexy stuff, like, it's not going to happen. Like, right here to book 700 people in four minutes. Let's go. It's like, yeah, sure, but, like, how can you really deliver on what you're saying? And I'm talking even down to the webinars that, you know, you and I build together. Like, I want the integrity of the hooks of. Of things that were, you know, promising that I'm delivering them at every single stop. And so that's something that I. There's this tension I think I have and I'm learning through to make that. There's also deep integrity with the marketing. And again, you're so great at that and kind of walking me through the mindset of, okay, here's how you think about it, which has been just a godsend. Yeah.
So when we started working together, your business had a certain structure and it had a certain, you know, all the organization in a certain way, and you had certain offers. And I remember in those first six months, it was a little. It was a little messy because you were kind of going through a pivot and this exact topic. Like, you're very good with people and organization and systems and, like, all of that stuff, but for whatever reason, it didn't have that proprietary nature like it does now in your webinars. When you're talking about the scale and you're talking about the hustle loop and all of these, like, big shifts. Do you remember how messy that felt like as we were starting?
Yeah. I have bad dreams about it. I do. I mean, at night I'm like. Then I wake up and I'm like, thank God. No, it is. It's that feeling of like, I have the thing. I have the. I have the solution, and I don't know how to best package it, serve it. I know what my audience needs, but sometimes they don't know that's what they need. So I was just like, here, it's right here. I got it for you. Shortcut. And they're like, I'm not interested. And it's like, but it's so. But this is it. This is the thing that you're like.
I promise you need this.
I really promise. So. And the beauty I think of me being in you and Kathy's kind of ecosystem of everything you all have created was. And again, I mean, we talk about AI all the time and how this is kind of shifting everything that's happening in business. I think those two things kind of where I was at in the business, and then kind of this Paradigm shift really brought me to that. It is about people, it is about the community, and it is about. You're not selling, you know, the. What's under the hood, what's in the course, what's in the community. You're selling how they feel once they've experienced it. You're selling kind of not necessarily just the result of like, like, you're going to be more profitable. It's like, okay, you're going to feel free. And so what we used to have was like a container of a really heavy course on building a team, which. It's a fantastic course. I love the course, but I think there's more to it. And that was kind of. That season was like, but I need to also help in different layers. And so then I got to experience your mastermind, Di. And I was like, this is it. This is the thing that I want to do in the wedding world. So that's been. Yeah, it's been huge for us.
All right, so let's talk about the design and development of your mastermind, because I think it's something that a lot of people want to do. And we decided that we were going to do a webinar, which, you know, people roll their eyes sometimes when I say, oh, do. Webinars are like, it's not new and different. Can you talk a little bit about the process of developing that webinar and that first webinar and selling those first seats into your mastermind?
Yeah, like the, the traumatizing moment when I sent you my sales copy for the first time. And then I just like, I was like, I need to go have some wine. Because I, I. I've never thought of myself as a great copywriter. And I, I had this kind of this inspired moment where it was at 2 in the morning. I don't know that, you know, this, that I was writing this down. And I was like, okay, here we go. It's like all the Juliana seeped in. And I was like, oh, here we go. We're on a. We're on a roll. And this is actually pre me using AI so the whole, the whole thing was really. Before I dove in and I said, I submitted to you. And you were like, ash, this is so good. I was like, I have achieved. That's also going to go on my tombstone, I think. But it was one of those things. I felt so proud because again, I think when you are in alignment, that not only how you help, but who you are and the strengths you bring. Alignment. It's you, you. It's on, you become unstoppable. And I think that's really what's been happening at the Abundance Group over the last six months. And I think, again, being able to do those iterations of like, okay, you know, and I'm doing another course now where it's like, I have that struggle of, like, I want to write the course first. And then I got to go back and Julie's like, sales page. I was like, julie, I'm just gonna die on this hill. I have to, you know, self more work. And I know it. But it is that idea of. Of when you're. When you really understand deeply who you're serving and what the problem is you're solving.
Yes.
It just becomes the clarity is. Is abundant. I mean, it's like, oh, duh, that's the thing I'm supposed to do. And so at that same time, I was also experiencing Di as a member, and I'm like, wow, this is transformative, and this is what I want my people to go through at the Abundance Group.
So you didn't have a mastermind. You launched this first webinar. I think you got somewhere in the ballpark of eight to 10 people off of that first big push. Right. So your mastermind now is. It's what, six months old? Nine months old? I can't.
Yes, nine months. August, like a soft launch. October was like, the big launch.
And how many members do you have right now? I mean, obviously it's a personalized program, so it's not meant to be huge.
Yes. I think there's. Last I looked for 40 of us all in, and I have a couple people that are. That are al. The cool thing we've also kind of brought together is I also have people that are in the mastermind that serve wedding pros. So they're actually like, experts. So. But they want to grow their teams and they want to scale and they want to use the model. So they're like ash. So they're in the mastermind as members, which I think is a unique for us, because now my members essentially get to rub elbows with some of the top industry educators and service providers. They are in it with them, which is so cool. So we definitely have some of those as well, which again, and I kind of ask them, like, show up and serve in a different way. And they all do. And again, I've had these relationships for eight years, so I feel I understand their integrity. I understand who they are. So I feel very confident of bringing everybody together in a unique way. So, yeah, that's yeah, there's about 40 of us now and growing, which has been fantastic.
So what would you say to someone who is, like, a little nervous about doing a webinar or not sure that that's, like, the right way to. To attract new people? Because I feel like I have to fight so hard for the webinar. And I'm just curious because I know it's not the easiest thing in the world to do, but what would you say?
I think it's a lift for sure. Especially to do it well and do it right. That's, I think, the thing people trip up on. I mean, I did webinars forever, and they, like, I look back and I'm like, oh, my gosh. Like, that is not a good webinar. I'm like, maybe I was charismatic on the thing, but wow. Yeah.
I think your personality definitely overcame whatever was missing in the tactic.
True. And, like, so, again, you know, working with you, it's like, okay, this is the structure. This is the why behind when we do this. This is the transformation that's happening right here. And you're not giving them that. Stop giving them that, Ashley. You're overwhelming all this stuff, you know, so it's just, again, I think having that, you know, your leaders through that has been so great. And I think that's the biggest catalyst for why people don't do it, because it is this big lift. But then if you don't do it right or you don't have the structure and the formula, you're kind of like, I don't know, is this going to work? And so I think for me, we did them, we had success. I can, you know, on a webinar, do it, you know, good job of presenting. But now that I have kind of your formula and your brain behind how it is built, it converts like crazy. It's wild.
Yeah.
Now, for. What about if people are like, I don't know if I want to do a mastermind or not? What do you think about the container? How has it been? What are the upsides and downsides of building your own mastermind?
I absolutely love it. I absolutely love. Now, again, I'm a people person, so that the call.
I think that's a prerequisite. You really do need to be.
Yeah.
Gotta like people a little bit. But I think to coach people or to, like, serve people, you know. Right. And I think the thing, there's. There's this. And I. At first when I started, I was like, they're learning from me and all the things and I have to dump my knowledge and all. But then I realized like I'm a fraction of the value of the mastermind. You know, they get coaching with me, they get all of our trainings, all of our tools. But then the community side, they, because we really laser focused. And these are wedding pros that are scaling that are beyond six figures. They have different problems than most of the market because most of the market is kind of, you know, new in the market, transitioning in and out. There's a lot, there's just a low barrier to entry. So there's just a lot of newbies always. But these wedding pros have a unique, unique challenges and getting in a room of people that also are at that same level or beyond where you are, you know, a couple steps ahead is just, it's incredible and it takes honestly the pressure off. As a coach, I don't feel like I have to have brilliant, perfect aha moments in every single voxer and in every single training that I'm doing because I know there's so much value with connecting with one another. So there is. And I'm still learning and walking into this in an even deeper and better way. But I think that is, you know, you think about the one on one coaching, the exhausting on zoom calls and all this, you know, kind of feeling like you're on a track just, I mean, the hustle loop, right?
Yeah.
But when you really focus on others and the value they bring and leading from that, again, it just takes the pressure off in a different way as a coach where you can still have the impact and the influence and honestly probably in a bigger way because of the other people. So I would say too, if you like people and you can really kind of have this humble view that you're not the show. You know, you kind of are right. When you market. It's your face and stuff, but really like the values and the others that are a part of it. I think masterminds are a perfect way and I think they get 10x better results than just a one on one coaching program.
Yeah, that's awesome.
I agree. I love my mastermind. So I'm, I'm glad to hear you echo a lot of the same, same benefits. Although it is, it's definitely something that you need to do if you, you know, you do it if you love people and you love coaching people. So just to kind of wrap up if, if someone's listening to this and they are in the position that you were before we started coaching. Right. An expert in something. But Sort of not. Not the best at being able to position marketing. Not quite sure of the container. Like, what would you give? What kind of advice would you give yourself or someone else who's like, right on that same spot you were about a year and a half ago?
I mean, I think it's just stop spinning and like, make a decision to invest in yourself. And again, I don't. I guess I don't know if you're taking on more DI members, but join di. I mean, come join. So much fun. We have such a blast. I can't wait to see everybody in just a, you know, a couple weeks. Yeah, but it is that of like, reach out for a hand. If you're feeling stuck, you gotta do something different. And sometimes different feels a little scary and a little challenging. It challenges ourselves, our resources, our time, our energy, our money. And that is where you get unstuck, is when you take that leap and you go, okay, I'm gonna do something different. I'm gonna have a different structure, I'm gonna have a different mindset. I'm gonna have a different community around me to get me out of where I am. And so, I mean, that was absolutely what happened to me on that fateful day on the lawn of Disney, the VIP lawn at Disney. And it is. I vividly remember that moment. And I almost can't picture where I would be. I don't know if the abundance group would still be here if I would not have jump. Made that jump. It was a. It was a moment where I felt like this internal pull. Right. Your gut instinct, your. Your intuition knows and listen and don't be afraid. Jump in. You're either gonna have a beautiful success or you're gonna learn something that was. You needed to learn anyway, so there's no downside. And like I say, I think you have to decide to get unstuck.
Yeah.
And I mean, and there are a lot of details to this story that we don't have time to go into. And as I remember where you were and some of the stuff that you were wrestling with, like, it wasn't a per. It wasn't like a perfect setup. You had to work through the transition. And I guess that's hope for people who are like, ah, it feels messy. I'm not really sure. And you pushed through all of that and you. You hung on to the vision that you saw, and now here it is coming to life.
Absolutely. I think the thing that allowed me to do that was focusing on my community. Like, if I give up, then I either they're not going to have the answers, they're not going to have the frameworks, they're not going to have the connection or someone else swoops in that doesn't maybe doesn't have the integrity or the receipts, the experience. And maybe they teach them incorrectly. Right. So you have to kind of keep your eyes on your people and go, like, I got to do it for them. And that was a huge thing that got me out of the rut, I think, and just pushing through and it was like it was work for sure. You know, I don't. There's no sugar coating it there of like it was. It was a lot of creations and. But again, the results paid dividends, not not only just financially, but in alignment of the business and how I show up and how I serve. I've never been more in love with my business than I am than I am now.
Yeah, that's such a fantastic. Such a fantastic feeling when you're in your zone of genius, which is very obvious that you are.
So.
Yeah.
All right, well, thank you so, so much. If people want to check you out, they want to see what you're up to. Where should they go?
Yeah, you should probably just come to Magic Kingdom at Disney. I'm probably. No, it's on the hub grass. Yeah, I can't, Julie. I'm not there yet. Okay. I don't have that private VIP tour money soon. Just kidding. No, I'm on Instagram. The abundance group is kind of where you find us. And again, we're just. There's a lot of scaling stuff I talk about that isn't just wedding pro centric. It's really about creat, a business and a life you love.
Yeah. Awesome.
Thank you so much. All right, thank you. Talk to you soon.
Bye.
And there you have it, folks. Another dose of million dollar grit. I hope today's episode has left you feeling inspired, equipped and ready to face your own entrepreneurial journey with resolve. Remember, until next time, embrace the struggle. Harness your grit and keep pushing forward. You're stronger than any challenge you face. I'm Julie and this has been Million Dollar Grit.