THA S02 EP#17 - The Unscalable Habits That Build the Best Communities

Most people think “community” is something you scale with software. But the best communities are built with habits you can’t automate. Showing up, remembering details, making thoughtful introductions, and creating spaces where people feel seen.

In this episode of The Habit Architect, host Michael Cupps talks with Leslie Greenwood, founder of Wednesday Women, about the unscalable practices that make a community stick. Leslie shares how a single LinkedIn post (“Which women CEOs should I know?”) turned into a Google Sheet, then into a weekly spotlight ritual that grew into 10,000 organic followers in 14 months and eventually a real business with layers: a public mission to amplify executive women, and a deeper executive membership experience. 

They dig into what separates communities that thrive from communities that stall: strategy before tactics, facilitation over “management,” and identifying the sticky glue that keeps people engaged. Leslie also explains why she uses AI selectively, not to replace the human element but to enhance it (like remembering details that make introductions more meaningful). 

The conversation gets personal too. Leslie opens up about being diagnosed with ADHD at 50, how it shaped her work rhythms, and the practices that help her stay centered like carving out short meditation moments (often in the car) and building support systems that make habit change feel doable instead of overwhelming. 

This episode is for community builders, founders and leaders growing networks, anyone tired of “engagement hacks,” and professionals who want relationships that lead to real opportunity, especially women pursuing visibility, connection, and support at the executive level. 

This Show is sponsored by TimeBandit.io

Check out our Live Show Events here: The Habit Architect Live Show

Subscribe to our Newsletter: The Habit Architect Newsletter

Transcript

Oh, and welcome to the Habit Architect. My name's Michael Cupps. So sorry for the late start. We just had a little technical thing we needed to get through and we're happy to be live now. Today it's a great guest. I'm really looking forward to conversation and we've talked a lot in past episodes about tying your habit building to values. Cupps: 0:23

And if you don't anchor those habits, they tend to be just something that you're trying to do on the side and they lose priority. But when you find somebody that actually does tie their habits to their values, you actually see them excel. And that's what I'm really excited about talking with Leslie about today because she runs a community called Win Wednesday Women. Cupps: And she's gonna tell you all about that in a little bit. But when you watch the way she interacts with the her members and the way that she carries herself, you can tell that the habit she has as a community manager. Carry over based on her values, which is she's living her authentic self. And that's what I really encourage people to do when you're thinking about building habits, especially as we look at July, January 1st, coming in a few weeks, those people are gonna start new resolutions and if you want 'em to stick, you really need to tie 'em to your values. Cupps: So we're gonna talk about that today. We're gonna

talk about empowering women. We're gonna talk about a DHD and family. We got a lot of topics to cover. Flora, why don't we bring Leslie online and we'll get her introduced. And while we're doing that, I just wanna remind everybody. Time Bandit io. Cupps: 1:23

This month we're doing a cyber cell for the bundled training so you can learn how to assess your hierarchy values link your habits to those values, prioritize, things like that. So do go out to Tom bandit.io, check out that training. And if you have a college student maybe that struggled last semester or you want to just get ready for the new year, go take that bundled course. Cupps: So we appreciate that. Alright, there she is. Hello Leslie. How are you today? Hey, Leslie: I am living well. I'm in Seattle and there's this thing called the Atmospheric River, which I was like, I don't understand the words that are coming out of your mouth, but there's been nothing but rain and gloom for the last three, so I'm doing great. Leslie: I'm, I've had coffee and I'm excited to talk to you. Cupps: Yeah, absolutely. You're primarily, you're in Dallas, right? Is where you I Leslie: am from Dallas, so I'm like a sunshine and warm girl. Cupps: Yeah. Leslie: And I am here

in it is. I, they say it's, this is like not normal and extra grainy for Seattle. And I'm like, yeah, no, you're not convincing me to ever live here. Cupps: Yeah, exactly. I will tell you, I, I'm in Dallas and it's sunny. It's a little cool, but it's sunny but no rain, Leslie: oh, we need to meet for real coffee then. Cupps: Exactly. We can we do this next time in person. Leslie: Yeah, let's do that. Cupps: Yeah. Great. I did see your LinkedIn post about your trip. It looks awesome. Cupps: Are you having fun? Good trip. Leslie: 2:23

I am. Yesterday was amazing. I had two coffees with women in the area. And then we have a nice set of members here. So we had a little dinner last night. We went to La Loba, which was a Spanish restaurant and a whole bunch of things. So it was really nice. And then stay another coffee and, just give me out in the community and let me network, not, I hate the word network, but let me community with the people and. Leslie: Hear them and listen to them and I feel like with great friends already Cupps: Exactly. Just looking at your posts and things like that, I can tell that this is what you love to do. So why don't you tell everybody about it? What, tell us about Leslie.

Leslie: Yeah. I any, anytime people ask me this, even in interviews, I'm gonna tell you first I'm a mom of three kids. Leslie: They're not kids anymore. They're all adults. They're all one of them is, not on payroll, but two of them are still fully on payroll. In college I have been an entrepreneur three times. Now I've. Never worked at a company over the size of 250 people. And I felt like that was horrible and the worst bureaucracy I've ever seen. Leslie: I am definitely an entrepreneur by heart. I love to build things with gum, duct tape and spit. Cupps: Yeah. Leslie: 3:23

And very oh and a Google sheet. If you gimme a Google sheet, I'm definitely good. Yeah, and I, I'm from the Midwest I'm from Indiana, but we've continually moved south and I love sunshine and warm weather. Cupps: Tell us about Wednesday women, why don't we get that at least out on the open so we as when you refer to the community we'll know what you're talking about. Leslie: Yeah. And it's so funny because the, when you say the word community, people have so many different interpretations of what community is. Leslie: It's like saying the word Kleenex. It's really tissues and there are

75 different types of tissues, and some are nice and plush and beautiful, and some are scratchy and are gonna make your nose bleed. Exactly. Yes. So Wednesday women, we started actually just as a single post me saying, who are the women CEOs I should know because my feed is desolate. Cupps: Yeah. Leslie: And that turned into a Google sheet, funny enough. And then I would just, as I saw more posts, I would have the fiber guy add to the goop Google sheet, and I would just drop it around to other people who ask the same questions. Yeah. It's like when you buy a white car, you see all the white cars. Cupps: Yeah. Leslie: 4:23

I met my co-founder Melissa Moody, who lives in Anchorage, speaking of cold and wow, it was negative five and it's snowing and all the things. I would never live there either. And we basically got on a call. She's what are you gonna do with this Google Sheet? I'm like, I don't know. I was just making a Google sheet. Leslie: That's what we were, I was doing. And then she's what if we did one thing? What if we. Made a post about one woman a week and we sh shine a spotlight on her. And I'm like, okay, great. So we opened up a LinkedIn business page with no business. It was a passion project. We both had kids at home. Leslie: This was just outside of our full-time jobs. Cupps:

Yeah. Leslie: And we made those one post a week. We decided we'd do it on Wednesday, and that's why we're called Wednesday. Women are one of our board members. It's do you think that Wednesday women still serves the brand? I'm like, no, but it's not the right name. Leslie: But that's name. So that's what it's gonna be. And then 10,000 organic followers later in 14 months. Partners, our first partner came to us. We had to become a business Melissa and I never even met before. Cupps: Yeah. Leslie: 5:23

And then yeah, and then after, then people, what we did was we created, and this is something both she had done at her previous startup and I had done with a previous community and my work is we created a bunch of raving fans, people. Leslie: Would say, I'm a member of Wednesday women. I want to be our first dinner. Someone said, I wanna be the chapter head of Wednesday, women in San Francisco. This was early 2024. I'm like, dude, I've not even written a newsletter yet. There's nothing to be a chapter head of. Cupps: Yeah. Leslie: We even have a talk about how to build community without building community, making people feel part of something, having

them attached to your brand. Leslie: And that's what happened. And after a hundred dms saying, how do I become a member? And we said, you DMed us. Congratulations. You're a member. We actually decided to build a community, meaning we have a virtual space. We have, lots of introductions, curated meetings virtual events. I'm doing a little traveling to come around and see members. Leslie: 6:23

But so yeah, so that's how we started. And that's, we have really, I think it's important to note is that we have really. There's multiple layers to our business. Our global mission is to amplify outstanding executive women. Get them in more LinkedIn feeds, on more stages, on more podcasts and sharing their authentic voices. Leslie: Really talking about the one behind title that's for everyone. Like you're probably a follower. Like we have, so ma everybody can be a follower of that mission. We can believe in that mission. That's for everyone. And then what lies underneath is the executive membership for women who wanna go a little bit deeper with that. Cupps: Yeah. Leslie: And so that's who we are and then what we do, and it really is, like I

said, it's a passion project that turned into a business. Melissa and I are both full-time on it now, which is amazing that I wake up every day and get to do something I'm passionate about. So it's a great, Cupps: that's awesome. Cupps: That's awesome. So it's interesting the way you described it and it's almost like it found you in a way, but years ago I worked for a, one of the first community software companies, right? We were selling a community package and then people would build their community around it. And it was fascinating to me because. Cupps: 7:23

Some of 'em would take off just just go and then others would struggle and they they had the same playbook, right? This, these are the things we're gonna do to create community engagement. But in some cases they don't. In some cases they do. What do you think it is? Is it the topic? Cupps: Is it the people? Is it combination of things? Leslie: It's probably a combination of things. Like one of the things that because between being the VP of member success at a very large community and then going out on my own, I think a lot of people, what they do is they build a community, but they don't actually spend time on the strategy. Leslie: Who are the, who would be the members? What are their

personas? What problems can I solve for them? What problems can I solve for them that other communities don't solve for them? And there's always an overarching. Thesis, even if I'm a brand community, it's an overarching thesis. It's not about, it's not about the widget, it's about the problem that you solve. Leslie: 8:23

And so really think taking time to think about that. But it also does, you do need good community facilitation. Yeah. Management to me is I'm just enforcing rules. It's facilitation. And you need to create the love between the people so that it feels sticky. And that's what I will say a lot is like you need to find the sticky glue that will keep your members there. Leslie: And it's not what, it's usually not what the community first thinks it is. Cupps: Right? Leslie: And so it takes a lot more digging to figure out what that sticky glue is. Cupps: Yeah, it's interesting and I did that a few years ago and, but I've watched communities build and I think we share a mutual friend Derek, who wrote Unfair Mindshare. Leslie: Oh yeah, Derek, he, of course, yeah. I've met Derek

actually. He's one of our. He's one of our board members. Oh, he's, I didn't know this. He wouldn't, yeah, no. Cupps: Yeah. That's fantastic. He and when I read his book, it was, he made a lot of really interesting points about community building. Cupps: 9:23

One of the things that I, that strikes me nowadays with ai, automations, things like that, I would venture to say more authenticity is most important thing in a community. But maybe I'm wrong. Maybe it's. Scheduled scope, scope of things or what's your thing about AI and automation? Cupps: Do you use it at all? Leslie: We. We do use ai. I want to use AI in the fact that I want to, like Melissa and I both have a unique skillset. My brain remembers miscellaneous things about people, which actually makes me a very good connector. It's one of my superpowers. Cupps: Yeah. Leslie: Which also makes me a very good community person. Leslie: Yeah. And but my brain can only take me so far. And so the Ai, I, what I wanted when we first bought our first platform was the AI to help me

remember or find those minute details about people so I could say, ah, Michael needs to talk to Jane. Not that Michael would be a member of our community. Leslie: Michael needs to talk to Jane because they both love kite surfing. Like those, that's what I want somebody to help me scale that part of my brain. Plus I'm a menopausal woman with a DHD. Gimme a break. I can't remember crap. So yeah, that, so that's where I want, if you go to our website, to, you always have the bot. Leslie: 10:23

There is no. Me and Melissa, we answer every, and that is something we will always do. If you come to our website and ask a question we're the bot. We really believe in that authenticity. And honestly, I will tell people this, like, how do you think AI is going to change your business? AI is gonna make me much more valuable. Leslie: Yeah. Because I will, the skills that I have and Melissa have and this ability to create rapport and make relationships and make connections become even more important. So let everybody go do all their AI stuff. I will use it to help me be more efficient.

Cupps: Yeah. Leslie: But the person never stops. Cupps: Yeah, I like that too. And I'm a big user on LinkedIn and, i'm a little saddened by where the community's going on LinkedIn, because I think automation is flooding it right now, but it's doesn't take long to sort out the au thought authentic people versus a, a script or something like that. Cupps: 11:23

It, and it just, I know it may catch up at some point, but right now it's so obvious that it's frustrating I think. But that's the world we live in. That's good that we can connect. But what about that? So when you think about. Posts and or things that you need to do and to engage the community. Cupps: What's the motivation or how do you plan it? Because it's really about habits, right? You may have certain days that you mentioned you, you highlight a woman on every Wednesday, so that's a habit. But how else are you in involving habits in the overall community management? Leslie: Yeah. And I think that's like in community world, they'll talk about habits and rituals. Leslie: And that's one thing I think, I'll just be honest, we need to do better at coming up with the rituals that are part of our community. One of the rituals is we do. And this is

what this happens in our dinners, which does is not a community only thing is that we talk about gives and gets and a lot of people talk about gives and gets. Leslie: We just reverse it and we ask the women for a get first. And so we will start off many calls with what's your get? Creating that neural connection. And it's okay to ask for help. It's okay to say I need help in this area, whether it's personal, professional, it might be big or small. I will guarantee you in a room of even 24 women, there's someone else that can help you. Leslie: 12:23

And so that's one of our rituals and habits that we do within there. But we could do definitely better on that. And then as far as posting, luckily I have a social media person who, Oh, Cupps: you. Leslie: Oh yes. We have, we, that was the first, because I was in charge when we first started. Leslie: Melissa made the carousels and my. Self was supposed to remember to post on Wednesdays on at a reasonable time. That was, I'm like, as soon as we get a dollar, like every time we made a hundred dollars, I'm like, we're $100 closer to hiring y Yana. You know what I mean? So I need to get this off my plate. Leslie: I still do my personal

posts, but she does all of our other social. Cupps: That's great. That's great. And you started when you introduced yourself first as a family around your family and mother. So tell us a little bit about that. You don't have to talk about necessarily your kids, but just how does that, how do you handle the entrepreneurship and three kids? Leslie: 13:23

Yeah. I think at this point of my life, it's much easier. Like I, I'm not, I'm on the other side of what so many of the women that I work with and talk to are. However, I did start my first business when my daughter that my previous employer changed their this was back in 19, in 2000, my previous employer changed their, maternity leave policy or whatever it used to be, you could just bring your baby to work. They changed that while I was on maternity leave. I said screw you. I will start my own. I'll just start my own business. So five months old, I had a baby on a hip. I would, it was basically a virtual, still a virtual business. Leslie: So was like a. Broker of food and feed ingredients, and so phone, fax, and modem. And, five months old and I had two

more kids after that, and I, honestly, I just did the best that I could. I was taking PO numbers and writing 'em on a diaper with a crayon. And I had my Blackberry and I thought I was all that. Leslie: And I'll here's what I'll tell to, it's like almost everyone is, I'll say this often, and then they're like, oh, that's o that's fine. I say, I always felt like a half-ass mom and a half-ass worker. Leslie: I al as a founder, I always felt that way. I'm like, I could be doing better at my work. I could be better at doing a mother. Leslie: 14:23

But I think that's also like ambitious women, ambitious people feel. I don't know that I'd ever say I was a hundred percent at something. But then that's how I always felt. And so when I talked to like other women that are doing that and they're feeling that way, I'm like, oh, that's totally normal. Leslie: Yeah. Everyone feels like that. And if you, and the fact that you feel like that just means you're a great mom. Exactly. It's can they say this? If you talk to a psychologist and say, I wonder if I'm a narcissist. They're like you're not, because no narcissist ever thinks they're a narcissist. Cupps: Yeah. Leslie: That's the easy diagnosis. Yes. Cupps: Yeah. Exactly. Yeah. I think you're right. That's interesting. And it's when you talked about the

gets with, with your group and your community. When you talk about that you also mentioned a small ripple philosophy, but there's some big ripples in women's career or arc, right? Cupps: There's menopause, there's children, there's when the children are young versus when they're teenagers and things like that mean there's a lot of ripples and that lifestyle, so I'm guessing your community has people in all of those stages, but do you have groups that support each of those kind of topics? Cupps: Or how do you handle that? Leslie: 15:23

Not quite yet. We don't have groups. We're still very small. We just launched in, in, in May as far as our formal community. But like we have a woman in our community that's a coach about with, for executive women and parenting. We will do, we do member led sessions and it's all based on what the members wanna talk about. Leslie: So we've done time management we have done negotiation. We also are gonna be doing some parenting ones. There's gonna be a menopause one. There's gonna be a thinking about having children and. Do I get on or off the career path? These are things that people talk about in our dinners, like we've talked about IABF, we've talked about freezing eggs. Leslie: We talked about what happens if I get off the path. Cupps: Yeah. Leslie: You know what, all this

kind of thing. So it's like we've all, I think, traveled what we say in our community is because it's for women who have had a VP or equivalent title in the past. 'cause a lot of women have I'm just gonna do my own thing. Leslie: So we've all traveled a very similar path to get where we've gone. But then everybody else, we just, all everybody else is a little bit different and all the different stages of life and I think people really appreciate to hear, those different. Those different things. Cupps: Yeah. Cupps: 16:23

And it's still I know there's, I don't wanna get political or anything like that, but it's still, it feels like there's still more resting on the women's shoulders than the men's. And, men have different things, but it still feels like there's a. There's, I don't wanna, I don't know if it's more obstacles or perceived obstacle, that we're, it, it's still not equal. Cupps: If maybe that's what I say. Leslie: No, and that's why you mentioned the ripple. That's one reason why Melissa and I said what could we do? Because we thought about can we ch, you think about. Change. Making change, yeah. The change of the, of women and there's pay disparity and extra pay

disparity for women of color. Leslie: There's all these things that need to be changed. And I will tell you some of the stories that I've heard, Michael will you will, you would literally say, I cannot literally believe that happened. So that is like a very large challenge and. As, a single person, one human on the earth, it feels very overwhelming to tackle. Leslie: 17:23

And so that's why we said we're gonna post one woman a week. We will make a ripple because we believe that making and all of us can make a ripple of some sort in whatever we're passionate about. And the one ripple will eventually turn into a wave. And that's what like keeps me centered and makes me still feel very positive about the work that we're doing. Leslie: Despite that, and there is a lot of feeling right now and a lot of unease within. The women we work with. 'cause the world is changing and it's oftentimes not changing in a positive favor for women right now. And but you know what? That, but we'll go do our one thing. We'll do our ripple. Leslie: We'll shine the spotlight on a woman. Let's make her feel fabulous today. Let's show an example to a woman coming up,

et cetera. Cupps: Yeah. Yeah. And now are your children involved in the community at all? Are they, do they participate? Leslie: No. My oldest is 25. She is a double bass player and Irish fiddler, and she's very much into music. Leslie: 18:23

She is doing things like that. A lot of our women wanna do, she's already on our first nonprofit board at 25. And so my, it's like a international society of basis. So it's not a little tiny one. It's a big global one my youngest actually is 19. She's a sophomore a swimmer at UCSD, and she's our intern. Leslie: She decided that she had time to stay on with us, so she helps us with the sustains, but like she went to college knowing HubSpot. Slack, Airtable and all this stuff. And oh, I if I make a post or something, she'll repost it on her own LinkedIn feed. I'm like, oh, look at you. Go girl. Leslie: She's got 500 followers on LinkedIn. I'm like, you have more than a lot of people I know. Cupps: Exactly. Leslie: Yeah. And my son, I tried to hire him as an intern, but I had to fire him 'cause he just did. I had he and I make

my, our youngest she actually has an employment contract. So good. Oh yeah, no, this, there's no, whatever you have, you're, if you're a worker, you're a real worker. Cupps: Yeah. Yeah. That's fantastic. And so that's wonderful. And the are they. Following in your footsteps? Are they entrepreneurial or are they, do they wanna go the corporate route or don't know yet? Leslie: Probably, my husband is super corporate, like he's fp and a big multinational companies. Leslie: 19:23

If it fits it like we are so polar opposite, I'm like, Dre all day, no black and white. For me. If your answer is no, it just means no, not right now. I might ask you later. He is, if it doesn't fit in the spread, it's the cells do not line up. Cupps: Yeah. Leslie: Life is off. Kind of thing. And so I think my, I don't know, I think the, my daughter, my oldest is obviously entrepreneurial because as a musician you need, you always have more of a, what we would call in corporate life, a portfolio career. Leslie: My youngest wants to be a lawyer. So I think she'll go that way. And I think my son will probably be some type of, some type of founder of something someday, but I don't know what, and I don't think he

knows what, but he's he has a DHD and dyslexia, so he is always been like, I remember when he was six, I said, the things that are making you so annoying at six, like the questioning and the thinking outside the box. Leslie: I'm like, I don't need you to think's outside the box. I needed to get your shoes on. I'm like, the things that made him so annoying as a 6-year-old, I'm like, are gonna make you such a great CEO one day. And so I just have to reframe it in my mind and be like, okay, these are positive things. These are positive things. Leslie: 20:23

Yeah. So yeah, they, they might run a little bit that way, but, we'll see. They're off to the what works best for them. That's what Cupps: it's about. Do you have Leslie: kids? Cupps: I do, I have a 28-year-old son who did not go into the business world. He's an lec, he's a journeyman electrician. He's doing great. Cupps: He's out in Fort Worth building schools is what he primarily they're primarily focused on and the daughter's in getting her master's at Texas Women's University. So she's almost out of out and she must be a counselor. Yeah. That's Leslie: amazing. That's amazing. Cupps: Yeah. I've got two women in my life that would probably love your community One's, one's a teacher at Hockaday and

then the daughter who's up at TW. Cupps: So I'll master. Yeah. Yeah. Leslie: Awesome. Thank you. Cupps: Yeah. But so you mentioned A DHC. We had a few weeks ago, months ago, I don't remember when we had a, the Gen A CEO from Fringe, which they sell benefits to school not to schools, to co companies, just alternative benefits for. Wellbeing all that. Cupps: 21:23

Learning opportunities, things like that. He was a great guest and he was talking about his A DHD. Can you tell us a little bit about that and how you navigate A DHD and still be an entrepreneur and a parent and all the other things? Leslie: Okay. It's a pig. That's a real thing. Interestingly enough, I was not diagnosed with a DH ADHD until I was 50. Leslie: It turns out there's a high correlation of the drop in estrogen in a woman's brain, and a lot of women are diagnosed later on in life. Because of that, my son, I knew I I. We, we got him diagnosed at six. I did every res, I researched everything. I read every book I took him. He's also incredibly intelligent and dyslexic. Leslie: So if you,

people are familiar with the term twice exceptional. So you're like gifted and habit learning, disability or learning difference. I, we flew to the foremost expert in the world to have the valuation and all of this kind of thing. So it's not like I was. Ignorant on a DH adhd. I never thought I, it never crossed my mind. Leslie: 22:23

I had gotten a new therapist and she's every challenge you're telling me is the sign of A DHD in a adult woman. I'm like, huh. Interesting. Yeah. Okay. She's you probably should try see about getting diagnosed. And so I went and had dinner with my friends not long after that and I said, my therapist told me that she thinks I have a DHD. Leslie: They're like, you didn't know. I'm like, okay, I thought we were friends. How come you didn't tell me before now? Cupps: Yeah. Leslie: You know what I mean? So I was like, okay. And so like the things that I, and as I look back now, like I, when I was a kid, I could not sleep. My brain was always moving. I, it was 3:00 AM and I'm still trying to like. Leslie: I

breathe through like my brain to fall asleep and things like that. You're of the age, you'll remember a Daytimer planner, that I would carry around. It was in a nice leather folder. I had all my credit cards and it was my purse, like everything was written down in there. The task, the list, everything. Leslie: 23:23

Yeah. And I think to a certain point, I could manage everything. I had come up with my own coping strategies to get around it. And then this time I think also being a consultant. So like I had two or three clients. I also had my own business. I had kids at home. It was just more than I could actually handle. Cupps: Yeah. Leslie: And the, there are listeners out there they'll know this, like the procrastination, the feeling of overwhelm. It's so for me it's like I had to push myself to the absolute limit. Like I can do amazing things at 3:00 AM with five hours left to a deadline. Yeah. Cupps: Yep. Leslie: But give me three weeks. Leslie: And I'm like, Nope. No, too, way too early to start that. Which then pushing the procrastination that far then creates anxiety, which

creates the overwhelm, but then for me, creates shutdown. Cupps: Yeah. Leslie: Which creates more anxiety. Yeah. All the things. And so yeah, so I, I'm still on my journey, I have, I, it's been, it's been a couple, maybe I was over 50, but, i'm still on my journey. I have, I'm, I take medicine. That is helpful. Cupps: Oh, you do? Yeah, Leslie: I do. Oh yeah, I do. I definitely take medicine. He's oh, you do. I can't tell from this interview, but you Cupps: 24:23

No. But he, I get it when my, 'cause my son is a DH ADHD and he's he's on medication, but he, we saw that when he was younger, not when he is 50. Cupps: So I just, it just struck me as Yeah, that makes sense. But Leslie: yeah. Yeah. No, I'm on medication. I'm getting a I'm. I've done a lot of, as you talk about habits, like I've not a great habit, but a habit as far as it's continued throughout the years. I've meditated for 1200 minutes this year, and that really helps me calm and center my brain. Leslie: And that's better than again, see there's, this is my absolute mindset. It is it's a habit, but it is a habit and it's better than the zero minutes I meditated the year before. So that is something that I'm

doing, but I also need more support. Yeah. And so I'm finding a new therapist. Leslie: She's also like an A DHD coach kind of therapist. So like I need, I need to talk about the whys and all that stuff. Sure. But I really need tactical, like accountability and. These, like you said, these habits. I have my Pomodoro timer. Yes. I carry it around. I never use it. I, I read, I bought Atomic Habits, but it's so overwhelming to even read it. Leslie: I get overwhelmed and I'm like, I can't do all these things and I close the book. Cupps: Yeah. Yeah. Leslie: 25:23

So I just know that I need more practical support and so that's exactly, that's my journey right now. And that starts like next week. Cupps: Yeah. That's exactly why I wrote Time Band. It was the how do you apply all the science that there and I used two concepts. Cupps: Eisenhower Matrix for priority management. Just know if you, sometimes just knowing you can schedule something to later removes it from your mind in a good way. Yes. And focus on what you need to focus on and in habit tracking. And I think it's, it can be overwhelming, but you don't do 1200 minutes of meditation without getting to a habit of

some kind, unless you really just dedicated to it. Cupps: But the I love the meditation piece and I've, I didn't. Maybe I did earlier in line from it in some other way, but now I think it's so important. I just movement meditation and moderation are the three things that I really try to help people on. Because, and meditation is such a powerful tool to just to slow down and take a pause and. Cupps: 26:23

Kinda reset. It's, such an important thing. And you don't it's not always like with your legs crossed and, and humming. It's anything that can help you get there and that mindset just kinda release. Yeah. Leslie: It's my deep breathing. It usually happens in the car in the morning after I've driven through Starbucks, and I'll sit in a parking lot for a few minutes and just have some moments of calm and quiet. Leslie: Then the sound is better 'cause it's in my car, and and then my husband's not looking at me like, and then coming to talk to me like, are you meditating? And I'm like, no, I am so go away. So it's just like my, that's my more likely time to meditate. But yeah, I can tell a difference in my mindset. Leslie: And if the people that you work with are like, they're, if

they're high achieving, they're fast moving. It's like my brain is always going, like even to stop and notice Cupps: Yeah. Leslie: Something. I'm like, oh wait, there's a nest in my tree with baby birds. I never noticed that. And it, you just are always going. Cupps: 27:23

That's exactly right. And even sometimes just feel your feet on the ground or your heels and your shoes if you were standing in a line in a airport or something just to Yeah. Just to get reset. But, so I wanna go back to I male. I'm feel like I'm following your pattern here, but the I wanna go back to something you said about your, you're getting together with women that are part of your team and you talk about the gets what are. Cupps: Could you summarize one or two or three big gets that you keep hearing over and over that women are looking for these days? Leslie: First, the first thing I'll tell you is when I say we're gonna do gets I do tell them usually in advance that we're gonna do it. I send them an email or two. Cupps: Yeah. Leslie: But the, they're like, oh my God. I feel very anxious right now. Like asking, they, they're like, oh, I don't know. Like they can't think of something. A lot of the women that we work with they,

they're thinking about visibility, 'cause visibility equals opportunity. So it's I would like to be on more podcasts. Leslie: Just I think how we met, I made a get on LinkedIn. I said I want to be on more podcasts this year. I made the post, I've got booked on six podcasts. You. So that's what I tell other women to do too. I'm like, just make a pose. Ask to be on podcasts. So a lot of women want, are looking to be on more podcasts. Leslie: 28:23

They're looking to increase their stage presence. Some are just looking for friends. Like in Seattle, there's a woman that just moved here six months ago. It's her, I guess there was a beautiful spring and now it's about to be, the dark season. And she's I just wanna meet people. Leslie: I want people that I want, will you just invite me to the things that you do? And that was her gut. Sometimes it's so it could be just like I want to meet more friends. I wanna meet more professional women. It could be also like business wise women moving into their own businesses. Leslie: This is what I'm doing, I'm building my own business. So I would love to meet CEOs that do X or have this, challenge. So it could be business related.

Yeah. And or it could be something super tactical. It's like I'm working on my first board presentation. Will someone look at my slides? Cupps: Yeah. Exactly. Yeah. Leslie: It could be any of those any of those things. Cupps: Yeah. Yeah. And it's nice that you're given an opportunity to ask that without feeling overwhelmed, even though some of 'em may feel overwhelmed asking for that. But it's it's great for that community. Cupps: I'm guessing that, do they find you on LinkedIn and then get to the community, or do they just look up Wednesday women and find your community? Or how are you, how are members finding. Leslie: 29:23

Yeah. Yeah. We are not doing very good. We're not doing much marketing of it right now. Leslie: It's mostly word of mouth and referral. We have these followers and so people that have been following this for a long time, they understand the vibe and we'll mention, of course, mention membership and I'm talking about going around to meet members. Cupps: Yep. Leslie: And people are like, oh tell me more. Leslie: And then, they'll decide if it's a good fit for them. I think you probably have the same experience. People there are. Different communities for different stages of your life. There are different communities for different needs, whether it's a learning community or a more of a connection community and like

finding your right community home or homes. Leslie: 'cause some people have more than one community home. So we just have, we have a lot of conversations and, if it makes sense for someone then and they have, it's just you have to have had that VP plus. Title at some point or equivalent. I know a woman who is the senior director of some kind of sales at SurveyMonkey. Leslie: She has 150 people underneath the her Leslie: 30:23

Yeah. She has more experience than most VPs of sales and startups that I talk to. And it's like that or equivalent because that's what connects us that path that we've all walked. Cupps: Yep. Leslie: Despite being in. Wholly different industries being public, private multinationals to one person starting their individual business. Leslie: Yeah. That's the thing that connects us. Yeah, mostly they'll find us out through, through that or someone told them, or, we go to a lot of conferences and we host a lot of events. I think for us it's once people experience a Wednesday, women, this dinner format or the coffee format that we do in person they get it. Leslie: They just ah, this is what we're talking about.

And yeah. So yeah. Cupps: That's fantastic. And so I've got one more question for you about the business side of it, and then I want to get to our, we asked two final questions in the end. But I know that you I was looking at Wednesday Women's website and you have sponsors. Cupps: What is a sponsor? Getting doing what's that about? The sponsor? Leslie: 31:23

Yeah. I would say mostly because we are new, we are not a huge community. I I don't promise anybody leads or anything like that, so it's mostly they're attracted to the mission. I would say I was talking to a woman before this, and there's. Leslie: I think you mentioned this a little bit, but like authenticity people, most of the sponsors that come to us we don't do outbound at this point. They already know and trust us in some capacity. So they're familiar with us personally. And they're like tell me more about that. So it's that resonating with the mission. Leslie: And then there's some familiarity and they may sponsor a dinner. And in that case, they are there, like their executive woman on their team will be there as a guest. And the goal for them is just to be there as a, an executive woman.

Like we're there together and then what happens is they resonate with that woman. Leslie: And even though I may not be buying Sendo right now, maybe I know someone and I met Patty at dinner and I'm like, oh my God, Patty's amazing. You should talk to Sanso. So it's that kind of, it's a brand. You know that? No. And trust, I mean it's really building that up with the women. We do series, so like we just finished a series on called Founders and Focus. Leslie: 32:23

So focusing on women founders, growth stage women founders, yeah. That were at 3 million revenue and above. I will tell you, those are purple unicorns. They are very hard to find. I should not have been shocked how hard they were to find based on the data of VC funding for women. But indeed they were. Leslie: Challenging. So like a sponsor may sponsor series, like Women in Product, women in something. And for example, one of our sponsors is a 30-year-old Nordic company moving to the us. We, I've known the CMO forever. And so we did a Women in Finance because it helps them with the brand visibility and also the positive of association with our brand and they believe in the

mission. Cupps: Yeah. Leslie: For us, one thing that's super important to be able to say is I need, and we'll be doing an announcement. Monday for a new partner, we always need to say, why? Why am I partnering? Why is Wednesday women partnering? Because if I cannot say why meaningfully, then I am no longer staying true to the mission. Leslie: 33:23

Yep. Now I always put asterisk if Salesforce wants to come to me and just give me a million dollars to put their, slap their logo on their website, I may not say no but in general, I wanna be able to say why this company is, it's important to us to partner with, and we ask them the same thing. Cupps: I think that's great. The community, but also get people in the community that can help lift it. That's fine. That's the way it should be. Yeah. Okay. I've I asked two, two simple questions, but I do have one get that I'd like to ask of you. Leslie: Oh, please. Cupps: So those women that wanna be on podcasts send 'em our way. Cupps: 'cause we love talking about various topics. So that's my get, we would open up. Leslie: I have some

amazing women already in mind for you. They have one woman that just ran a time management class or like meeting with us. Amazing. I was like, oh, I love all these things, but oh, you name it. Leslie: Give me personas. I will give you names all day long. Cupps: That's great. Let's do it. Let's try to get the Women Wednesday guests coming. Yes. So there we go. All right, so the first question is, what is a non-negotiable habit you do every day? Leslie: Ooh. See, I'm a really bad person to ask that question. Cupps: 34:23

I thought that was gonna be a, I thought that was gonna be a tough one Leslie: and not, brush my teeth. Cupps: Yep. Cupps: That is one. Leslie: Drink, coffee and drink coffee and brush my teeth. I am I will make, I'm the worst. I will put time blocks on my calendar and ignore them. I will say, I'm gonna use my p pomodoro timer to keep myself on track and I will not do it. I am the. I am the worst. I do drink a lot of water and then I have my morning coffee and I brush my teeth. Leslie: Those are the things I promise you that I habits that I will do every day. Cupps: Yeah. Yeah. Somebody wrote she need, you need the time banded out.

Leslie: Yes. Alright. I'm gonna, I'm gonna have to look into it because I am I swear I think I've, every year I'll buy a new schedule or meeting thing and all these things, like every new tool that I think is gonna help me. Leslie: Every year I obviously need, yes, I need, or enablement. I am just, gonna be just vulnerable and say, I need more enablement. Cupps: Yeah. Yeah. Cupps: 35:23

Yeah. That's true. And then the other question I have for you is I talk about this, tomorrow's more important than yesterday, and I think your whole mission is about that, right? Cupps: But anything you'd like to comment on that Leslie: tomorrow is more important than yesterday? I think I. Do I? Yes. Do I believe that? Do I fully believe that? I feel like as long as you learn from something from yesterday. Leslie: Then yes. Because I think there are lessons that we have that we need to learn, that are given to us or something. Leslie: As long as we take that learning from yesterday into tomorrow. Yeah. Because that's where we make the impact. I can't make an impact in yesterday. I can make an impact in

tomorrow. And I can make an impact in today. I guess maybe even for me, because I'm a person that has constantly thought I don't wanna say wishing away my life. Leslie: I remember as a kid saying, oh, I can't, when I'm 13, it'll be so much more amazing when I graduate high school. It'll be so much more amazing. So for me, I think it's like today is more important than yesterday, and today is actually more important than tomorrow. But that's also some A DHD in there. And you're talking about making habits and I'm saying, no, man, let's just talk about today. Cupps: 36:23

And that's fine though. I like that. When I started contemplating that statement, it was because I was, I think I did a session with a group that was really stuck in yesterday. They were, they couldn't get out of their way because that's the way they did the things. And this is what we've always done. Cupps: And I couldn't, couldn't get 'em to think of that. And I think anybody that's looking to. Change, whatever change is for you, you have to start, you gotta focus on what's ahead instead of what's behind you. But I agree with you have to learn from mistakes and

lessons and all the stuff from behind, great. That's great. Everybody should find you on LinkedIn for sure. Are there other ways that you wanna share with them how to find your group and. Leslie: Yeah, Wednesday women.org, that is our website. You can find more about our global mission, more about our membership. Our Wednesday women Follow Wednesday women on LinkedIn. Leslie: 37:23

That's where we put out our content. That's where we share the features of women, the series things that are going on with us. But yeah, I'm on LinkedIn, just Leslie Greenwood and I'm on LinkedIn way too much my. My, my phone app tells me that regularly. Feel free to DM me or chat. I'm always always open to connect. Cupps: Thank you so much for getting up early and sharing your thoughts with us today. I really appreciate it. Get an umbrella. Stay dry until you can get back to Texas where you can warm up and dry. Leslie: I'm going to Denver next. I'm afraid it's gonna be real cold. Not, I, we live in Texas. I don't even own a coat I don't know what's gonna happen there. Leslie: But thank you so much for having me. It has been such a pleasure. I love this conversation. Cupps: Yeah, thank you so much. We enjoyed it too. And everybody watching Tune in Next week we're gonna talk to Carson and