Building A Powerful Community Of Women To Fight Entrepreneurial Loneliness With Alexis Dean

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TTB Alexis Dean | Entrepreneurial Loneliness

Entrepreneurs can get lonely too. With the pandemic, loneliness is a very real thing. People want to talk to other people who share the same interest in the business. This is why Alexis Dean founded The Dovetail Community, a global community of world-class women entrepreneurs. Join your host Mitch Russo as he talks to Alexis on how she started the community to fight entrepreneurial loneliness. Learn how she grew her community of women by referral. Find out how she manages her summit events. And discover why purpose is more important than a product when it comes to community building. Don’t be lonely today, and tune it to this episode!

Listen to the podcast here:

Building A Powerful Community Of Women To Fight Entrepreneurial Loneliness With Alexis Dean

Our goal is to help you be a better leader, inspire more people, create the passion your community wants and profit from the experience. Readers, I want to hear from you. Tell me what you want, who are you interested in hearing from and what community that you have? What action do you take from every amazing guest we talked to? If you’re a coach then you may want to check out my newest SaaS platform for coaches, which boosts productivity and saves time on your session admin for $20 a month. Check it out. It’s

My guest is the Founder and Lead Steward of the Dovetail Community. A global organization of women on a mission to advance female entrepreneurship through generosity, collaboration, education and unforgettable shared experiences like the Dovetail Summit and Camp Dovetail. I can’t wait to hear about those. With many years of experience and as an educationist, professional facilitator, trainer, consultant, educator and speaker, she has worked in 21 countries, with more than 100 corporate teams, nonprofit and school facilities. If she’s not at her desk, you’re going to find her hiking, paddleboarding, swimming in lakes and rivers, skiing and exploring. Welcome, Alexis Dean, to the show.

Thanks so much for having me, Mitch.

It’s my pleasure. One of the things I like to do at the top of the show is I like to set the tone for the show and I do that with a statement. In this case, what basically is a community leader and what is a tribe leader? What is a tribe builder? My answer is this. A great tribe leader can polarize passion with purpose and mission. If you can share with us how you do that then that would be incredible because that’s what this show is about but before you do, we all are very curious about how all this got started for you.

Our origin story for Dovetail starts with me because I am an entrepreneur and I have been an entrepreneur for years and I essentially built the community that I needed. I had been in business a few years, running a corporate team building and training company. We’d grown our staff team and we were starting to work across the continent. I’m based in Canada but we had American clients and clients across North America.

I didn’t know any other woman who was like me. I knew women with small, without any teams and I knew lots of guys that had bigger companies but I didn’t know anyone that had the same ambition, wanted to talk about the same things, that had big dreams of leaving a big legacy and making a big impact with their business. I started off thinking, “I’m going to host a weekend and I’m going to have a dozen women come and we’ll go up to a lake house in Ontario. Maybe some ladies from the States will come and from Canada. It’ll be a good group of about a dozen.” That was years ago and we ended up with a list of 50 and they all wanted to come.

I ended up renting a big lodge that we could have about 50 women. I think it’s 49 that first winter and I planned a winter weekend. I thought, “This is going to be amazing. I’m going to make friends that get me and I’m going to get them. Maybe in the future, we’ll have a get-together or something,” but the plan was not to have a full business out of this. The plan was to find my people.

What happened was that other people found their people. At the end of that weekend, the ladies asked what we were doing next and one of the ladies owns a vineyard and she said, “Why doesn’t everybody come to the vineyard and let’s plan a vineyard weekend.” That was the beginning and it’s been a few years of leading this incredible community of women.

I cannot ignore the parallels between what you’re doing and what many entrepreneurs do. I think the greatest gift of an entrepreneur is to have a need and look for a solution. If you can’t find it, let’s build it and that’s what you did. That’s what I did with the software that I talked about. It’s all about the fact that you didn’t have this community, you didn’t even know people who could and now you do and you started to serve you which later grew much deeper and much broader to serve many. I love that. How would you describe your tribe’s core mission? What would you say that is?

If you can't find a solution, build it. Click To Tweet

I’ve been working on this for years and at first, it just happened. People came together and I realized we were there to solve business challenges and we have a couple of different core groups that we serve. We have our very established women entrepreneurs and then we have our slightly newer women entrepreneurs, still in business for a couple of years but slightly newer.

With both of those groups, I used to think that our mission was to serve them in their businesses and to help them leave a greater impact. I still think that. We are a very impact-focused group. All of our ladies are very purpose-filled whether they’re running a SaaS company whether they have a construction company, restaurants or whatever it may be. Product-based businesses, all the range.

In the end, our mission as a community is to help to eradicate entrepreneurial loneliness. It’s something that is so prevalent and so incredibly common especially during these times. It’s something that other entrepreneurial groups strive to do as well and that’s probably our core mission at the end of the day. Close to all the other staff.

There are other things but what I love about what you’re saying is that it didn’t take some super complex manifesto to build this. It basically started with, “I’m lonely. I’d like to surround myself with some other incredible women. We all have similar interests and needs so let’s get together.” That’s fantastic and it’s a great way to start. You had 49 people come. Was it that very first session?

That was the very first weekend that I hosted and it was in the middle of winter in Canada. A couple of hours North of Toronto. We had people fly in from Georgia, Florida and California. We had a whole truckload of extra winter gear for them because it was minus 30 Celsius that weekend and they still came. It was amazing.

What is the size of your tribe?

Between our ladies who’ve been part of our ongoing year-round mastermind, which started before COVID and our ladies who are in our Summit group, which is our more established entrepreneurs, plus our ladies who’ve been part of Camp. Most of them stay in touch through our Facebook group whether they’re part of our ongoing programs or not. We have about 250, give or take a few.

That’s pretty good growth. You’ve done a great job there. The thing that I’m curious about is how do you go from 0 to 49 people in one event? How did you get the word out? What mechanisms did you use?

My goal was never growth. There are communities out there that have thousands or hundreds of people and that was their goal for their founders. For me, I want depth. I didn’t want growth. I wanted a real connection. The way that we have grown for any of our programmings whether it’s the Camp, Summit or anything else, has mostly been through referral.

When I started, when I wanted and I thought, maybe a dozen women. It sounds great. Maybe ten, I don’t know. I knew two people that I thought I’d met at something and I was like, “You might be interested in this. Would you come for a weekend? We’ll cover the costs. Would you be into it?” They were like, “Can I invite this person or can I invite this friend? I know somebody who’d be a great fit.

TTB Alexis Dean | Entrepreneurial Loneliness
Entrepreneurial Loneliness: You need to help to eradicate entrepreneurial loneliness because that is something prevalent, especially during these times. A lot of entrepreneurial groups are striving to do this too.

There’s this person that I met that I would love an excuse to spend a weekend with her.”

I said, “Yeah. I like to make a connection. I’d love to meet her.” I ended up with 5 or 6 women who knew when I talk about this. I call them our pillar women. They are women who are hyper-connected and are the ideal fit for our community. They are generous lifelong learners, who are adventurous, purpose-filled, humble, have a lot of fun and have that little bit of courage to do something that’s outside of their wheel that they would do all the time.

Those pillar ladies help build the community. Once I had that core group and I said, “It looks like we’re over a dozen, do you think there are some other people you can introduce me to?” They came back and we had people that couldn’t even attend because we had too many women on the list. Some of those ladies came back with a list of at least twenty and they were like, “These women should be there and we should do something with them.” Having those early pillars helped in getting people who are excited about what we were doing and wanting to get activated.

Once this group started to form, did you panic and say, “What kind of a monster have I created,” or were you ready for it?

I think I got ready in the months leading up to it. Once I decided, “We’re going to do more than 10 or 12 people and now I’ve rented this lodge. We’ve got to have a whole thing. We better have enough food for everyone and make sure that the lodge is providing great food, drinks and everything else,” I then started ramping up for it.

From that point, when I started to realize like, “At least this weekend needed to be something.” It helped to get the ball rolling for the rest of it. After that first weekend, when they said, “What are we doing next?” I turned to the friends that had volunteered to help me that weekend and I said, “I’m going to need your help with this.” They had been there ever since. I’m so lucky to have a core group of friends that I’ve helped them with their events and they’ve shown up for Dovetail since the start and it’s been incredible.

We’re talking to the amazing Alexis Dean. She is the Founder of the Dovetail.Community. She is telling us her story about how all this happened for her, which is incredibly interesting and important because what we’re talking about is how this whole thing unfolded quite naturally. I’m hoping that the clues are there for you.

As we go through this conversation, take some notes. It seems so logical and yet, where she came from was a place of passion it goes right back to our statement. What was she passionate about? How did she communicate that passion to others? Alexis, now that you’re a little bit more formalized, did you start to add some tools? Did you start to add software or infrastructure? Tell us a little bit about that.

Because it was gradual and yes, that first year we did a winter summit and then we did a winery trip. One of our ladies in New York said, “Come to New York,” so we did a New York weekend. That first summer, we did a trip out in the Rocky Mountains. Because of that growth, we needed a few things. At first, we have a PayPal, Ticket Tailor or something like that. That wasn’t effective. At first, I started to merge with my other company. We started using some of the same software and opportunities for people to jump in.

You have some basic tools now in place for payment and for communication. I understand that you’re in the process of building a new membership site, is that right?

When building a community, you should want real connection over community growth. Click To Tweet

Yes. Over the course of COVID, we built out a membership for our ladies because we couldn’t gather. We had plans for camp, for dinners and different cities and for our annual summit for our more established women and all of that was canceled. When we couldn’t be together in person, we started gathering online.

We started mastermind groups, which are small cohorts of peers that were heavily curated to 6 or 7 women per group. They met with the facilitator every two weeks. We have monthly gatherings for the whole community. We started using a platform called Circle, which is great software. If you’re a community leader and you want to get your group on Facebook, software like Circle can save the day.

We experimented with Mighty Networks and our ladies didn’t find it as user-friendly. We had Circle for our members and then Facebook for our regular group and then we use ActiveCampaign for our mailing list. I send out a weekly email called DoveMail. If you’re a member of the community, you get a slightly different one than the public does. We have ThriveCart, Stripe and all the usual subscription, payment things.

Our website is on Squarespace. We don’t use anything too high-tech. Our programming is simple. It’s not designed to be convoluted or complex. It’s designed to be user-friendly because I do all of the calls with all of our ladies if you’re coming to our summit or any of our more intimate gatherings. I speak to everyone and then I send them personalized invites. It doesn’t go through any big convoluted funnel system or anything like that. It’s literally coming from my inbox either for myself or one of my team members.

I will say this. You have a more sophisticated system than many of the tribe builders I speak to on this show. While you go, “It’s this and that.” It’s quite beautifully constructed. Detailed and well-organized. I want to commend you on that. Again, I want anyone who’s reading to basically see how all of these things can be used and still keep that very natural feel for a very closely-knit community, which I love. Let’s go a little bit deeper on that. You talked about trying to help people not be lonely. That was the original mission but it’s evolved from there. What benefits do you think you and the tribe now provide to your members?

Curing entrepreneurial loneliness is what a lot of entrepreneur groups try to do. For a lot of our members, they’re all women or folks who identify as women and they’re all entrepreneurs. We don’t have any corporate participants or anyone else who is not an entrepreneur. There is so much that they learn from each other.

Whether you’re a part of our more established group, at our Summit whether you’re coming to Camp or pretty much everyone from the community comes to Camp. Whether you’re running a $1 billion business or you’re in your second year of business, there is so much that we can learn from masterminding and peer-to-peer support through our round tables or our workshops and then through having conversations with each other.

I love the stories from our ladies who will sit down at dinner. They run a software company and they sit down next to someone who owns a chain of pet stores and suddenly they’re talking about the things that seem obvious in the pet store world, probably don’t seem that obvious in a tech company and vice versa. There’s so much cross-business learning that happens so many insightful moments to a level of relate-ability that again goes back to that entrepreneurial loneliness. It also opens people’s eyes to a different way of doing business and a different way of showing up as business leaders in the world.

This is what great masterminds are for and this is what a great mastermind, as defined by Napoleon Hill, is simply two minds together who are greater than the sum of each other. I love that and the fact that you’ve done that. I want to ask you something that I have never asked before because no one’s ever said it before. Your members are women and those who identify as women.

TTB Alexis Dean | Entrepreneurial Loneliness
Entrepreneurial Loneliness: There is so much cross-business learning that you can get from a group of entrepreneurs—from masterminding, peer-to-peer support, roundtables, workshops, and just conversations.

I don’t know if that’s the correct terminology right now. It’s changed a bit over the past years but we have non-binary folks in the community. We have transgender women in the community. We say women typically but in an effort to always be as inclusive as possible, I try to include terminology. We’ve also had a couple of folks who identify as men who were keen to come to Camp and so they came. We try to be inclusive as possible.

The goal is not to exclude anyone especially with our Camp. At our Summit event, which is for the more established women entrepreneurs, there is a reason we’re slightly more exclusive because there’s a type of conversation that happens when you’ve been in business that long. It’s a different conversation when you’re talking about millions of dollars in your business versus your first six figures.

That’s the only time when we tend to lean a little bit more to the exclusivity but with Camp especially, we want to create a space where every entrepreneur with their own business, who is an actual entrepreneur, can come together, learn from one another, learn from the workshops that we host and the guest experts and mostly from each other.

Every time I interview somebody, I learned something and me being an old guy, I’m still a little new at how all this stuff works and that was fantastic the way you described it for me. If you’re reading this, I hope it was a benefit to you too. Let’s get into the money because after all when you heard the introduction to the show, what we said is to build a great community based on your passion and profit from the experience. Tell us about the evolution of how you chose to set prices and what services that you guys have created an offer.

That first event, I thought, “We’ll cover the costs and maybe a little bit more,” because it’s always going to cost more. If you are planning your first event for your community, estimate that it is going to be more than you could have budgeted for. There are always additional fees, costs, extras, swag and whatever it might be. You can’t always count on your sponsors even if they commit.

You have to have enough in the budget to compensate if a sponsor backs out last minute or anything like that. At that event, I didn’t lose money but I didn’t make the money but we put on a really good event. After that, when I started hosting, I started to try to build enough of a buffer that I could be compensated for my time and then any team members from my other business who at first, pulled them over from my other business and put them in this business to help out so that I could compensate them.

When we looked at doing trips to Wine Country, New York or our summer summit, the prices steadily increased at every summit and at camps so that we could pay for things. It costs money and this is maybe something we’ve talked about before but people say, “I don’t think I should need to pay for friends or I shouldn’t need to pay for a community.” They’re not paying for friends and they’re not necessarily paying for the community or connection with each other. They’re paying for the hard costs of the realities of running a business. I need to eat and pay the staff. I need to pay venue costs because we run all-inclusive events so our venues, foods, drinks or swag, which as much as we don’t need fancy swag, we always like to have the creature comforts.

We get people tuque if we’re in winter or blankets if it’s fall or whatever we need for the venue. I started low and started without making money and then gradually over the years, it’s got to a place where I can at least afford to pay myself from it, pay the team from it and have a bit of a buffer for incidentals because it’s always going to cost more.

The first product was the Summit itself and then you gradually increased the price as you have continued to run it. What was the next product?

When building a community, growth and service shouldn't be first. Having a purpose should come first. Click To Tweet

After that, I would say the pop-up events. We started doing those weekends I mentioned, New York, Toronto, Collingwood, Wine Country in Ontario and then our BC weekends. Those were smaller pop-up things and then we did the Summit. The summits were the first big revenue generator then the pop-ups, dinners and then Camp, which we ran pre-COVID.

I couldn’t run during COVID but it’s coming back and it’s going to be amazing. I cannot wait for that and that was 150 women and a little bit of an investment for them but not something to have which would be too prohibitive. We did have scholarship spots for those who come from disenfranchised communities who might not be able to budget for it despite having a business. That was another way that we generate it.

During COVID, we’d sold all these tickets to these events and because this has happened to other people, it’s important to put it out there. When we make money on tickets, almost right away, we have to put deposits into venues and then these are not cheap. Oftentimes, when you’re making a deposit, they sometimes want a 50% deposit on a venue upfront when you make the booking. When you see us selling tickets early, it’s because we are paying big venue deposits and those deposits don’t come back. Usually, in contracts for things like this, you can get a reschedule date and you’ll lose part of your deposit or they’re not going to refund. Either you reschedule or you lose that money.

What happened during COVID was I couldn’t refund everybody because I’d paid a huge venue deposit so that money was not available. I didn’t have it sat in the bank waiting to be refunded and I’d had to pay for staffing and have to pay for other supplies for the event because we’re close to a couple of them. I then was faced with more than 100 people that had paid money.

In some cases we were able to postpone the events so that was great. I could say, “You’re going to have a ticket to the next time we were able to do this.” In the meantime, what we did was offer them membership. We started a mastermind membership. For those that had tickets, they could either hold their ticket for the next event or they could use the credit towards the mastermind program. That’s how the mastermind started. We brought in more women in order to generate enough revenue to pay the team, pay for the business and keep going through COVID. That was the next revenue generator for the community was the mastermind program.

You’ve done an incredible job. I’m proud of you. I love seeing the work you’ve done and you’re setting a great example. I’m going to ask you to give us a little advice to my community. This is a question I ask every guest because each person’s situation is different. For those thinking about building a community, should they create the community first or should they have a product or service in mind to sell first?

Neither. I think they should have a purpose first. I work with purpose-based and impact-driven businesses. We don’t do anything unless there’s a reason to do it. If you want to build the community like what I see happening is influencer people. Having followers and saying then that’s a community. We need to look at the meaning of community and have a reason why you want to bring people together. Not together to follow you but together to support one another. I would start there and then I would look at, “If you’re bringing them together to support one another, how are you doing that? Is that something that’s going to cost you money?

Do you need team members and software? Do you need things to be able to do that effectively? Do you need to be compensated for your time if you don’t already have a product to offer them? If you do then it’s like, “How can you generate revenue for that?” It depends on how you see a community. The influencer world is so foreign to me and I know some people do start by trying to influence. I think being an influencer, unless there’s a purpose for influencing that you’re educating people on something or you’re offering them something or giving them something, you probably can’t start by amalgamating people because they won’t follow you unless there’s a reason to follow you.

If we go back to the statement at the top of the show, “A great tribe leader can polarize passion with a purpose and a mission.” We start out as a tribe leader with a polarizing passion and polarizing to me means you’re not included and you are. We want to as strongly exclude as we do include because that gives the community boundaries. That’s what all great communities have.

In fact, all great entities, countries and companies, most are supposed to have boundaries and hopefully, they do. When I go back to the question I asked about, should one build the community around their polarized passion first, without having an idea of what they’re going to sell? Maybe they have a company with a product and service that they’re already selling and then, “Maybe I can build the community around that.” What is your thinking around stuff like that?

TTB Alexis Dean | Entrepreneurial Loneliness
Entrepreneurial Loneliness: If you’re planning your first event for your community, you have to estimate that it is going to be more than you could have budgeted for. You can’t always count on your sponsors, even if they commit.

I talked to business owners who don’t have communities yet. They might have followings and if they’re starting and they already have a great product or they have a service and especially if they have a little bit of a following behind that already and want to bring together their people to support each other and using it. Software companies are another great example of this or pet companies. Pet lovers love other pet lovers and they can work with each other.

I don’t know that there’s a clear answer to that. I think if you have a business, there is an opportunity to build a community around it, whatever that business may be. If you don’t have a business and by business have something that you can sell. If you don’t have that yet then there’s an opportunity to come up with a reason for gathering people and then start from that reason.

I don’t know if I’m giving you a straightforward answer but I think it depends on your personal circumstance. If you’re starting with a company, yes. There’s always an opportunity. I’ve seen companies build community in the wildest of ways. You wouldn’t think that they could build a community but all of a sudden, they’ve got people gathering and they’re gathering either on their property or off their property or online. They’re supporting each other with it and then they potentially in the future do want to gather together in person.

I think your answer is right. It’s instructive because a lot of the folks I speak to have companies and then come to me. I build tribes. That’s what my second book was all about, Power Tribes. One of the things that I love to talk about is what is a tribe? What is the structure of a tribe? What does culture mean inside of a tribe? Those things need to be defined before the tribe starts or else you end up getting in trouble. Sometimes if you’re a corporation and you try to create a community without boundaries and what I call a code of ethics, with no value structure and no leadership, it results in chaos. What you end up with is not a tribe but a mess.

That’s part of why I’m leading these questions because I want to show people that even folks like you, who happened almost by accident, had a strong purpose and a strong vision for where you wanted to go and that’s incredible. Let’s move on to the future. Let’s look into our crystal ball here and say, “What’s in store for Alexis Dean? What does that world look like?”

It has been such a wild ride. I will be completely transparent. I have paused our online programming and so our mastermind ladies are not gathering. I did that because we are re-imagining what Dovetail could be. We’re still planning for our summit. For any established entrepreneurs who are reading, that is coming up in the Bahamas. It’s going to be phenomenal. It’s an intimate gathering.

I’m excited about that. I don’t think that will ever stop. I love hosting those and the same thing with camps. In a couple of years, I will still be hosting the camp and that will continue but what our online programming looks like and everything else in between, I’m not entirely sure. I love facilitation and speaking so that’s something that I’ve been doing a little bit more of while slowing down our online programming.

I would love to own a property that we could host our own gatherings on. That could be something where we do quarterly gatherings in the future. I have a couple of friends that do that with their communities. I would love that and my partner and I live up in the Canadian North and would thrive on that. That’s an opportunity but honestly, I am not 100% sure. This is the first time in years that I am not completely sure what the future holds. I’m rolling with it and sticking to those core programs that I love, like our Summit Camp and then everything else in between. I’m sure it will fall into place.

I love your answer because it’s honest and it’s the truth. We don’t know what’s going to be happening. You’re building your own little Galt’s Gulch. If you haven’t read Atlas Shrugged then you have no idea what reference I made. If you haven’t, now is the time to read a book like that because it basically spells out all of what we’re experiencing. Ayn Rand wrote that decades ago. It’s amazing.

What I love about what you said is because if you then buy that piece of land, that potentially could be a homestead of sorts at some point in the future and as you say, a physical location to basically put a signpost up and say, “This is our community.” I love that. Alexa, how do people get ahold of you? Where do they go to find out more about you?

If you have a business, you can easily build a community around it. Click To Tweet

You can learn about the community and what we’re offering from Camp to Summit and then when we do relaunch online. It’s all over at www.Dovetail.Community. People get confused sometimes and they can’t find us. All of the stuff is there. If you are a more established entrepreneur, who’s been in business a number of years, typically a 7 to 8-figure revenue business. You can go to

I understand that you have a podcast that where you get to talk to people in your community and about your community. What’s the name of your show?

It’s called Think About This and it’s not for people in our community but I started it because I make so many introductions, as many of us who are community leaders do. I don’t interview women on it. I have people support each other. What happens at our events is often that two people will gather together and as I said whether they’re from a similar industry or a completely different industry, they end up sitting there and talking through meals or after hanging out and jamming.

I wanted to be able to be a fly on the wall for that. Think About This is the name of our podcast and I bring together two smart entrepreneurs plus myself and they support each other with a specific challenge that one of them is having. If one is wanting to get back into the media and she’s built a cool business but she’s fallen off track with being covered in the press. That was one of the episodes of the season. Then I brought in somebody from our community who is an expert in that area. She talked her through exactly how to get her company back in the press and get herself back in the press and that thing.

We’ve had everything from one mom who went through great maternity leave. She owns a very successful business with about 100 employees and it was growing. She went on mat leave and she supported another one of our ladies who was pregnant and was looking at how do I do this. How do I leave my business for maternity leave when we’re right in the thick of it? I looked for ways for all entrepreneurs, men and women, any gender identification to come and support each other and it’s been a real joy.

I’m going on with that pause. We’re doing a short series. We’re talking about entrepreneurial burnout. Instead of having the two other entrepreneurs come, I, myself is going to be one of those smart entrepreneurs on the podcast. I have a variety of different fascinating experts from my personal therapist to a woman who specializes in Psychedelic Integration Therapy to all sorts of people. A nutritionist who works with burnt-out entrepreneurs. There will be quite a number of folks and that will be our next series in the podcast. You can find us at Think About This with Alexis Dean on Spotify or Apple.

I have a feeling that you’re going to be getting some new audience and including me. I love the idea of what you’re doing. I am very excited about the community you’ve built because you’re a shining example of what can be done. I appreciate you and our time together. Readers, if you enjoyed this episode, let me know. If you want more people like Alexis on the show, tell me and I’ll go get them. That’s my job and I want to hear from you. Did you get something out of this? Are you building a community? Do you want to? Let me know? Alexis, thank you so much. We’ll talk again soon.

Thank you.

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