Your Permission Slip to #dothething with Community Builder Lisa Webb

This is The Entrepreneur School podcast where we believe you can run a thriving business and still make your family a priority. This show is all about supporting you the emerging or early stage Entrepreneur on your journey from solopreneur to CEO while wearing all of the other hats in your life. My name is Kelly Sinclair and I'm a brand and marketing strategist who started a business with two kids under 3am, a corporate PR girl turned entrepreneur after I learned the hard way that life is too short to waste doing things that burn you out. On this show. You'll hear inspiring stories from other business owners on their journey, and learn strategies to help you grow a profitable business while making it all fit into the life that you want. Welcome to Entrepreneur School.

Hello, Lisa, I'm super excited to have you on the show today. Thank you for joining me all the way from Paris. area.

Area south of France, but right country, we're good.

Excellent. Oh, that's good. This south of France is nicer than Paris. Right?

Yeah. Got a little more space down here.

Fantastic. Fantastic. Okay, before we jump into this episode, which I'm super excited about, I would love to start by asking you a little bit about like, as a mom and an entrepreneur, if you could think back to the beginning of when you started your business ventures, what advice would you give yourself?

I would probably say, Don't forget your balance. Because sometimes things get hard and they get heavy and we go all in because as entrepreneurs, we are so passionate about what we're doing. We all usually have a why behind what we're doing. And it's so strong for me anyways, and for women that I know and have spoken with that we can get so into what we're doing that we can get off kilter during those crazy busy times. And to avoid burnout. I would tell myself to remain balanced to keep doing the things that make me happy. Keep moving my body don't stay up late working keep all of those important things in check. Because you'll have more stamina for the long run.

Hmm I love that because especially at the beginning we can tell ourselves well it's only going to be for a little amount of time until I get to the X result or goal that I have right and then

Yes and next thing you know four years has gone by you're like oh my god I'm still going at that pace. Because it really intense

yeah and sustainable a little bit right.

Yeah. And so it's kind of like a garden that you need to like, mow the Earth. Clearly, I'm not a gardener, but you need to, like, you go in seasons, and you can have really busy seasons. But it's nice to always like, make sure your own cup is full, and you're taking care of yourself, and in ways that you need to.

Yeah, that's such such a good reminder all the time, for sure. And you have built something really amazing with the wine women wellbeing community, maybe you could just share a little bit about like, your vision for that, what it is how it's evolved as well.

Oh, it's so amazing. And I actually am fairly new to the community myself, I had my first experience outside of like, I've went to a couple of local local branch events. But I went to the wild conference in last spring. And it was just so powerful and amazing. And it was amazing to hear your story as part of that. There were a few things that you talked about that just really resonated with me and I know would like they align with, you know, the way that I think and act and I think that will be really supportive for people listening to this, as well. And you told this story about reaching out to Gillian Harris one time.

Yes, I did. So the brief version of that story is when I moved so I'm originally from Thunder Bay, Ontario. And I moved to Calgary at 22 years old. And I started teaching immediately when I got there. And I was connected with this beautiful spirit, who was teaching across the hall for me, and we were going to be partner teachers. And that was 22 years ago. And so that was or 20 years ago, I guess now. That was Melissa sudo. And Melissa sudo has been a friend and mentor all of the things to me for the last 20 years. And fast forward 15 years later. Her son is, I don't know, 15 years I might be wrong there. I know how long Jolin Jessen have been together. But her son is now with Jillian Harris. They are. We'll call it married. So Jill and Justin are together. So I was overseas for all of those years when they were dating. And in that period of their life. So anyways, I came back from overseas. And I guess so I'm in Calgary. I don't know what it was. I think we were out at sudo cabin in Kelowna. And then we ended up at Jill's house and we're having wine and I was like, okay, really like this is pretty much as good as it gets. I'm drinking wine and Julian Harris's kitchen. And when we left there, we went out for dinner, and Melissa and her husband and myself and my husband, and I was like Jill reminds me of my cousin's she's just so nice. And she just what you see is what you get. I just love her. And Melissa's Husband, husband, Paul says, like, you should ask her to be your mentor. And I'm like, Please do not make it weird. Like can I just Jill's really nice? I really liked her. Let's just leave it at that and not make anything awkward.

And at this point, I hadn't even like started Wine woman wellbeing.

No, no, I had that. I think that was I think this was no she had already done an event with us in Calgary.

Okay.

So we had our like, I met her in Calgary. And then we met. I think this was after our event that we had in Calgary. So I already knew her. I was just rambling about how much I liked her at dinner that night. But we didn't have like a relationship where she was my mentor or anything like that. And so he was like, just, it's not awkward. She's family, your family just sent her a message right now and was like, No, Paul, I'm not sending her message. I've had several glasses of wine, like, we just need to drop this. I'm sorry, I brought it up. And he was like, take out her phone. And so I sent her the most awkward, like, just awkward message. And he took my phone for me. And he made it more way more assertive than I ever would have wrote. Like, it wouldn't send a message like that to anyone. But I did send it to Gillian Harris, and kind of wanted to die after. But she messaged me back not right away. Super awkward waiting period. And then she messaged me back. Yeah. And yes, exactly. And so she did end up mentoring me during COVID Because it was COVID. And everyone was stuck in their house. And we would meet on Zoom, and she would mentor me. And it was just a really kind thing and a great experience for me. And that I always think of that, like I think of what Jill did for me. And if I can pass that on to someone else. Because she's busy. She has a lot going on. She didn't have to do that. But then on the other side of that you never know what's going to come from something because I found out so this was like two, maybe two years ago, she used to mentor me three. I'm my mother's really aren't what is exactly. I'm like there was a streak of German COVID. So how long ago was that? Anyway, it was before the manifest to her for sure. And before the wild conference. And so it wasn't until after the manifest tour that Jill was on Caitlin's podcast off the vine. I was listening to it. And I was multitasking. I was doing something else. I was like, did they just say my name, and I grabbed my phone and I like had to rewind it. And so on Caitlin Bristow was podcast, Jill was talking about how during that time when she used to mentor me, that's when she came up for the idea for the Giulia Academy. Because as we were going through all of this, like I was like, What do I want to do with my life? I might be moving to friends. Should I keep one woman or my being? Should you travel things. And so Jill said, I wish that I just like she was thinking in her head, I just need a handbook or I need some kind of guidebook that I can give her on like the blueprints of what I have done. And that's when she came up with the idea for the jelly Academy. So I thought that was pretty cool. Because you never know where something is going to lead. So she was doing it to help me. And in the end, she came up with a business idea, which was pretty cool.

Yes. So like in summary, in short form, you awkwardly texted someone who you admired, hoping that they would help you like you reached outside of your comfort zone, and way outside of playing like what am like all of the thoughts that are going through your head at that time are like, Oh, what if she says no, what if she like never wants to see me again? What if worst case that she could do? And then that even turned into like, obviously an amazing mentorship relationship and a great story. And it inspired her. So you actually in the end really helped her by doing that. So what if we can all think about things that way that if we reach out and actually ask for what we want, that it's going to be a reciprocal sort of thing?

Yes.

Just about what we get out of it. Right.

And I think that sometimes sometimes it's timing, and sometimes it's, and like, I've reached out to people all the time, you half the people I reach out to don't even email me back. And that's okay. And then you can reach out to someone again, like a year or two years later, and everyone might be in a different spot in their life in their career, a different season. And you just never know what's gonna happen. So I feel like when you get a nudge, just follow the nudge.

Mm hmm. I love that so much. And it's really it's why you're here right now, because I heard that story. I talked to you at that event. And I was like, I'm gonna send you that awkward emails just like that. about something and then later, it's evolved into Hey, just wanted to let you know that I have this podcast and you're like, cool. I'd love to be on it. Yeah, like, yes, the we can make things happen. And you can it'll and Oh, sometimes too, though, don't you find? It's really the small thing that actually can lead to the big results when sometimes we think oh, it has to be this big, complicated strategy that's going to get us there. But sometimes it's just asking a question sending a text message.

Yes, I will be perfectly honest with you. I have no strategy. I'm all just like passion and heart and fire and I just go for things. I would love to say that I sit down and do like annual goal setting and annual business. as clients, I do not do any of that I just like, I strike while the iron is hot, I do what I can. When I feel fiery, I go after things. And when I feel like I need a season of rest, I rest. But I don't have some gigantic game plan. Like I said, one woman and well being was supposed to be one event. And here I am, what, four years later with all these branches across Canada, it was not like you just never know where your path is going to lead.

That's so amazing.

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So what is your like trick to actually giving yourself permission to have no strategy and to actually like feel connected to just do the next thing?

That's a great question. I think that if I had to, like on the spot answer that question, I think that the lifestyle that I have led, being this global citizen and having to move every two years, I've had to recreate myself, every two years. And at one point, so I was teaching or I was an admin. And then I left and I thought I have to do something. So I started writing. And I ended up writing a lot. And I was writing books, and I was on the Huffington Post. And I was like, Oh, wow, I became successful at this. But then I stopped because we moved. And then I had to start something else. And I went back into teaching. I was like, Oh, I can do this again. Okay, I have become successful at this. And I thought, well, I'm going to try this. And along the way, I did all kinds of things. I was like, well, let's see if I like pottery. Nope, turns out I don't. It's okay. But that's not going to be my thing. It's not going to try yoga, I became a yoga teacher. I studied enough to do all the course. And then I thought, You know what I actually, I don't like yoga, as much as I like running. So I'm gonna run instead of do yoga. And that's okay, I give myself permission to try new things, and adapt to change, adapt to where I'm living. And I've just had many, many seasons of my life because the way things have been set up. And so I give myself permission to try things, see if I like them. So if it brings me joy and happiness, and I can find success, and then I keep going. And if not something else will come. Because I remember I was writing when we lived overseas the first time I was writing as Canadian expat mom. And when we said that we were moving back to Canada. So many people were like, what's going to happen to Canadian expat mom? Oh, my God, that's your identity. And it had kind of become my identity was like, Oh, my God, what's going to happen to Canadian expat Mom, I have no idea. And then it was kind of ironic, because I had got a bit of a following on that account. And that's the account I use to launch wine women and well being I said, I'm going to do this other thing. And if anyone is interested in if you're in Calgary, follow along over there. And I kind of sent people from that first account that I had, over to the wine woman and wellbeing account, which is now far larger than the Canadian expat mom account was that I just ended up turning to my personal kind of travel account. So I just think I give myself permission to try new things. If it's working great. And if it's not something else will come and just follow the path as it goes, I guess.

Yeah. That's it's beautiful to hear that and it's also I know, hard to do. Like, I think that myself and a lot of other women entrepreneurs, we He can overthink so much. And maybe that has a little bit to do with what we actually think of as success. And what like, when we're thinking about trying something new, or the fears come in with what if it doesn't work? What if it's not successful? So I'm curious what you think about when you think of success? What is your definition of success?

I think it depends what we're doing success. First of all, it doesn't make you happy. Because if you're not happy doing him, who are you doing it for? That's the I think that's number one. If it brings you joy, their success there. I mean, some people might think of it as a number or a following, I can't handle like, likes on a post, like, Oh, this is success. I don't love that. There is something to it, we're all like that we're in this space where if you want to run a business, you also have to become sort of an influencer, which is a little bit tricky to navigate if that's not your thing. But I don't necessarily define that as success. So I think if it if it brings you happiness, if you can find a way to do it, as your job for a long time, I didn't depend on one woman and well being as my job, I was always a teacher. And then so I always was teaching. So I didn't, I could make decisions in that space. Not with finances at the front. And so I was able to just really do things that felt good. And that felt in alignment with me. Because I had my job, I was a teacher, I had a career, and that was paying the bills that I needed it to pay. And I was doing this other thing on the side, because it made me really happy. And I didn't make that full transition until just after COVID really like after manifest or no before manifest. And while but there was a point. After COVID, when things opened up again, and my husband's company said, like his his contract was due and it was you can either stay in Calgary, but you don't have a job anymore at this point, or you guys can go overseas, and you'll have your job again. So we had to decide if I was going to continue teaching while my husband looked for something new in Calgary, but during COVID. That was like, not an ideal situation. And, and he really likes his job. And he's been with this company for like 18 years. So we can either have all of the financial pressure on me, or we can move back to the south of France, where I could go all in on one woman and well being not have to teach anymore. And then he would keep the job that he had. And I was like, Okay, I choose Plan B, I choose to go all in on one woman and well being. So that's the point that allowed me to do that. And so I've been able to make it work for us. And I guess we just have to wait and see where the path leads.

Yeah. Do you think that you change, like, make decisions differently from like, you were talking about how before, you know, the financial pressure, and maybe the financial pressure for your family, and everybody has their own different like situations of where things are coming from? Obviously, when you have a business? In order for it to be a business, it has to make money? So let's just put that out there as fact, right? Would you make decisions differently like now thinking like you're all in on one woman and well being versus when it was like, kind of just considered a passion project, or maybe even still considered a passion project and that you get to be all in on it.

I think I do make decisions a little bit differently now. Because the stakes can be a lot higher. When you put on an event like manifest or wild. There's a large, large financial risk involved, because those are just massive, large scale events, which I didn't even to be perfectly honest, I didn't even know the size of the implications that came with all that I'm not an event planner. I'm an educator. And so there were just things that I had no idea I was just thinking like, Okay, this is how much it costs to rent the space. And this is how much it costs for the speaker. There was just things that I didn't even know about, like lighting and sound and all of these extra things. And so I definitely look at things through a financial lens first, a little bit more now just because really, there's just more of far greater risk. Because things have I mean, of course, renting out the Telus Convention Center is a far larger commitment than renting out a coffee shop for two hours for 30 people, which is what we did the first time, like our first event compared to where we are now. It's kind of like when someone is you know, selling things out of their spare room like selling T shirts or whatever. And then they get a brick and mortar. Those are two very different things. Like you just you can't operate the same way.

Right. So what helps you, like, continue to have confidence,

Yeah, to be able to put up some boundaries in a secure place. Mm hmm. Okay, well, Kate, first, maybe a little context, if anyone's listening in, they're like, what's wild? What's manifest what's the Action Center? People are not necessarily all from this lovely area, though, you should all come and visit and definitely check us out. But like, just give some context to what those events are, like scope wise.

Okay. So like I said, we started just renting out tiny little coffee shops that had a capacity of 30 people. They would close in the evening, and we would rent those. And then as things scaled, and I kind of had this idea like let's go bigger, let's, let's get a celebrity involved. And so the Telus Convention Center is like in Calgary, and that is our large I don't even know how you started large convention center. But so we had, we got Caitlin Bristow, for the manifest tour. And we went to Calgary, Edmonton, Saskatoon and Kelowna. And on average, we had 700 Women at every event. It was fantastic. And it was exciting. And it was all of the things. And then the wild conference is women inspiration, leadership and development. And with that, we had Dr. Jody Carrington, and Elizabeth Gilbert and myself. And that was a full day Women's Conference. And you can watch for that coming again this fall. So that's very exciting.

Yes, so these are, these are big, these are not like, Oh, I think I'm going to throw an event and 700 people are gonna count. This is next level stuff. So that's amazing. And I hope that you're so proud of what you've been able to build. How does it feel? Actually, I mean, I heard you speak on the stage. So I got some of that. But like, I'd love for you to share a little bit of how it feels to stand up there and look around and go. I made this

Goes crazy. I don't think it sinks in. I don't think it has sunk in yet. Once in a while, like someone will post something on a picture. And I'll be like, to that hat like was that my life did that happen? Which is amazing. But I feel like I genuinely feel like I don't know when that when will that hit me? Well, that hit me when I'm like, 80. I don't know. Because I don't feel like for me, it just is like, oh, yeah, that was fun. That was a fun thing that happened. It was great. And okay, let's keep going. Let's see what's next.

Did I don't feel like that much more than what you like the 30 people in the coffee shop, like in terms of your own like view of the success you've created? Does it just feel the same?

Like, no, it kind of does unless someone that like what you're doing right now says like,

Isn't that crazy? Well,

I don't have to like if I sit back and I look at it, I go, Yeah, wow, that's a big deal. But on a daily basis, like my husband keeps me pretty damn grounded. I will tell you that, like, not letting my head get too big. I just like I just see like, Okay, well, let's see. Let's see what's next. And I don't know,

Do you know what there's a term for this? And I can't remember what the word is. I can't remember what it's called right now. But it's like, and I've experienced this because you think I'm gonna write a book. And when I write that book, my whole life is going to change

Yeah.

Nothing changes. When you write a book. Like I'm and especially like, a book is a weird thing because it's not like, like maybe have a book tour or something like that, but I've written many books like I've started reading kids books. And then I was in anthologies, I published anthologies. And then I got like a traditional publisher published my book. Years ago when we were living here in France the first time. And nothing changed. Once I wrote the book, it was great. And I was proud that I did it. But my life didn't change. I mean, if I was Elizabeth Gilbert, and they wrote, Eat, Pray, Love, My life would have changed. But for the majority of people, like it's a great accomplishment, you feel good. But it really doesn't change that much. Like, for example, that has happened, it was amazing. I was on this high, I loved it. I, I did. And in those moments, I felt like I was on top of the world, it felt amazing. But I came home and my kids were like, Mom laundry, this and then life carries on. And you know what I mean, life has a way of just keeping you grounded. And like dishes need to be done. And you just You carry on, and then you're like, that happened. Remember? Like, what are those high heels? I haven't worn those heels. Since I'll tell you that right now. Like, where am I going to wear them? So it's just life has a way of marching on. And then I guess you just think, Okay, well, what's the next thing and you keep working? And then your your goals get bigger, and you continue? Like, I still like on my goals? Like, yes, I want to speak on giant, large stages. And, and it doesn't end? I think it just continues.

Yeah, it's making me think like, what if we could just act as if our goals are already here? Because like, we think that when we like, so often we think about a goal. And like, once that goal happens, I'm going to change, something's going to be different, like the feeling that I think I'm going to, I heard this said before, that the reason you set a goal is because of the feeling you think you're going to have if you achieve it, like and what you're saying is like even if you do achieve it, you're probably not going to feel that much different. So why don't you just feel that way now? Yeah. Or you just like do the goal, right? Continue doing it, but like, embody that feeling now?

Yeah. It's like when people want to get stronger. And they want to start like, I'm going to use weightlifting as an example, because that's what I'm currently doing these days. Because I was like, Oh, I have, I have some back pain. And my doctor told me, if I start lifting weights, like just moderately lifting, I'm not going to competition or anything. So don't get excited. But it just started instead of running. I started doing some weight training. And it did actually really help my back. So my back is better. That doesn't mean I'm going to stop lifting weights, right? I just want to get stronger now. So once I'm strong, it doesn't mean a quit. They're like, okay, that check that was done. That was great. It does feel really good. But now I'm just going to continue. Kind of like when people get like a healthy eating plan. They want to change the way they're eating. Once they get there. They don't stop and turn around and go back. They just continue on. That's now their normal your I guess like your benchmark just changes, right?

Mm hmm. Yeah. Yeah, that's so interesting. Ooh.

And I remember the first time I spoke in front of 200 people, I actually genuinely said to my doctor was getting a physical she's like, how are you? I was like, Oh, my God, I'm so good. I'm so anxious. I have I'm speaking at this event for the first time. And it was when I moved back to Canada, the first time was speaking on embracing change. And one woman and wellbeing did not even exist yet. And that was going to this woman's event, and there was gonna be two to 300 people. I was like, I have a friend who takes Xanax do I need that? Like, I am so anxious about this? And she's like, I think it's really normal to be anxious about public speaking. And I remember that was two to 300 people. Yeah, manifest was 700 people over and over again. And of course, I was nervous, but I switched that nervousness for excitement. And I wouldn't told myself I'm not nervous. I'm excited about this. And so what once was terrifying and so exciting, and the biggest thing I thought I'd ever do, was a stepping stone to something else.

Yeah. Yeah, exactly. We're always gonna keep wanting more, like, setting the new goal and everything because that's how we, you know, evolve. Yes, it's never gonna be done. Like you're a like, that's life. You're never done until you're done and entrepreneurship on top of that, it's that's what it's all about. Like you've never done. So be here for the ride, right?

Yes. Enjoy the journey.

Yeah, exactly. Okay. I want to ask you just a question about, like, motherhood and entrepreneurship and how you navigate that, especially like uprooting your whole family every couple of years and moving to new places.

Oh, and it's such an important life lesson to have, like, you have to like you can do hard things to try new things. Yeah, I love that.

They don't know any different. They know, their mom's a teacher. They know their mom runs a business. They know their mom's written books. They know, their mom had to leave her business, so to speak, like geographically. And they know that we're going to go back and that's okay. And that we just make the best of the situation that we're in. They know that there's things that we miss at home like, Oh, this is happening. It's so and so's birthday. Wish we could be there. They know that and we can't. So what's the next best thing we can do? We can Skype them, we can make them a video, we can send them something. We're going to see them in the summer. We just we're teaching them I think a lot of resilience to.

Yeah, that's amazing. Yeah, that's a skill that you need to to navigate life and especially one when you're an entrepreneur, right?

Yeah, they got a front row seat to it all.

Amazing. Well, Lisa, I feel like I could just talk to you for hours and hours. So thank you so much for sharing all of this. And I'm super excited to see what's coming up next. Is there anything that you wanted to share about right now or just let people know how they can connect with you?

Like I said, you can watch for the wild woman inspiration, Leadership and Development Conference coming in the fall. And if you want to connect with me, my Well, I live in a couple of places online. You can of course find me out one woman while being on Instagram and also Lisa web official. And winewomenwellbeing.com Is the website.

Perfect and I'll make sure all of those links are in the show notes. So please go reach out to Lisa she loves it when you send her awkward messages asking

Awkward. All the time. Do it ask me for what you want, and we'll see if we can make it happen.

Practice. Go practice doing that with Lisa.

Yes, I love it. Now I'm gonna be like wait now. Let's see how weird this could get. Bring it on.

Okay, awesome.