How to Design and Build a Community with The Lola's Eileen Lee

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This is a podcast episode titled, How to Design and Build a Community with The Lola's Eileen Lee. The summary for this episode is: <p>Ten years ago, I joined a newly-formed Fellowship program called Venture for America, a non-profit that takes recent grads and trains them as entrepreneurs to work at start-ups in lower-cost cities like Detroit, New Orleans, Cleveland, and Providence.</p><p><br></p><p>The Chief Operating Officer of the startup that was VFA, and our guest today, is Eileen Lee. Following six years running VFA, Eileen is once again putting her community-building chops to work as the co-founder of The Lola, a physical workspace and digital community for women.</p><p><br></p><p>In our conversation, Eileen teaches me about what it means to be a community builder, how she was initially wrong about The Lola’s target audience, and why the Start, Stop, Continue exercise is undefeated in surfacing the best ideas.</p><p><br></p><p>Like this episode?&nbsp;<a href="https://www.drift.com/operations/review" rel="noopener noreferrer" target="_blank">Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️&nbsp;review</a>&nbsp;and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz and @DriftPodcasts.</p>

Sean Lane: Hey, everyone. Welcome to Operations, the show where we look under the hood of companies in hyper- growth. My name is Sean Lane. One of the perks of having your own podcast is you have a great excuse to ask people you've long admired to sit down and talk to you, you know, for work. 10 years ago, I joined this barely formed fellowship program called Venture for America. It's a nonprofit that takes recent grads and trains them as entrepreneurs to work at startups in lower cost cities like Detroit, New Orleans, Cleveland, Providence. If you know anyone that did Teach for America, it's that, but for startups. What was a pleasant surprise to all of us involved in those early years of Venture for America, wasn't just the fellowship itself, but the community that sprang up from the fellowship. The chief operating officer of the startup that was VFA and our guest today is Eileen Lee. Following six years running VFA, Eileen moved to Atlanta and is once again putting her community building chops to work as the co- founder of The Lola, a physical workspace and digital community designed for women. In our conversation, Eileen teaches me about what it means to be a community builder, how she was initially wrong about The Lola's target audience and why the old reliable start, stop, continue exercise is undefeated in surfacing the best ideas. To start though, I asked Eileen to take me back to the catalyst for why she wanted to start The Lola.

Eileen Lee: After my first, I think, go at starting a company with Venture for America, I did some reflection as we pushed our fellows to do. So, for the first time, I actually took pen to paper and tried to articulate what I wanted to do next and why, and what sort of the mission was behind that. How did that get me closer to whatever career I wanted to build? And I remember looking at the worksheet, and it actually, a lot of the questions are from that co- founder's chapter in Founder's Dilemma because at certain point I realized," Oh, it's starting another company." I was able to articulate things that I never actually knew why I wanted or thought about, but one of them, I remember being like I wanted to be a role model to other Asian American women. And I remember reading that being like," Oh wow, actually I've never even thought of that out loud and that's interesting." So yeah, I think it was, for whatever reason, I knew I wanted to start something else. I also knew that I was moving to Atlanta and leaving New York for the first time in my life, so understanding that startup ecosystem was kind of the first step and the rest is history. I didn't intend on building another community startup. After the second time around I realized, I said," Okay, I think there's... I'm probably onto something. This is a sweet spot of mine." And now, five years into my second company, I am very much like," Yes, I am a community builder." I love creating businesses and filling gaps and making an impact, but particularly in the community space.

Sean Lane: That's amazing. So for folks who don't know, can you tell me a little bit about kind of what the community is at The Lola, right? You said you wanted to do this community, this was something you learned about yourself. What actually was the shape and form that The Lola took?

Eileen Lee: So I think the first problem that we identified and it's something that still continues to persist that workplaces, for the most part, whether it's a big company or a startup is still a challenging environment for professional women. So is there a space? And we talked about space as physical and virtual space. Is there a space that we can create to support women? Because oftentimes these environments cultivate competition, toxic culture, women come and filter what they say, they can't bring their true self. So is there a space that we can create that's safe and comfortable for women to come together and talk through these challenges, support one another, thrive with more ease and less hustle is really what we were getting at. And our initial focus groups and surveys, we wanted to do pie in the sky stuff so we had posted sessions, inaudible VFA and some of the fun ones were, one of the questions would be," What do you think that a physical space designed for women needs to have?" And we had one woman who was convinced that- And pre- pandemic at the time, we were all wearing heels and dressing up and looking our best and she said that once you walk in, you have to take off your heels and then the floors will feel like pillows because we have to conform ourselves into one society deems as appropriate, this is casual or work wear. So we had some fun with that and I think everyone understood when we were like," Okay, realistically, we don't have a budget for that." But yeah, we were able-

Sean Lane: You don't have padded floors throughout, it's like trampoline style.

Eileen Lee: Right. But yeah, we were able to do other things where we took into account typical things like, to this day in 2022, the vast majority of physical environments are still designed with men in mind, everything from office temperatures, they basically gauge that based on a male body and body temperature. I read somewhere, as late as 2008 or something, some of the prescription medications instructions were updated because women were actively overdosing again, because they were mainly writing the instructions and directions for male bodies. So, it's called the coded patriarchy. So we got really deep into that kind of stuff and thought," Okay, realistically, what can we do?" And so we have comfortable seating with again, women and our bodies in mind, different sizes because there's not just one type. We have inaudible everywhere, we have the mother's room, we've got diapers and toys and all the things, if you need backup childcare help. So all the things that I think that offices tend to lack, we made sure to include in our space

Sean Lane: In case you couldn't tell already, Eileen is a thoughtful, purposeful community builder. And while she didn't pull off the floors that feel like pillows, she clearly had a specific vision in mind when she began planning for the physical space that The Lola would become. We're going to talk a lot more about this community that Eileen is building, but because of our shared history, I wanted to go back a bit to learn how her previous community building experience at Venture for America shaped this second go round. What was helpful from last time and what wasn't?

Eileen Lee: I think the number one takeaway, and I didn't even realize going into Venture for America, I thought it was such a great program. We were creating for entrepreneurs, again, it hit me much later on the community and the power of the community, but also the sense of belonging. And I saw that in the fellows and you were in the first class and we were just doing things literally the night before trying to figure out what we were going to do the next day at training camp. And the thing that did hit me, and I remember you all giving us pushback too, it's the sense of belonging. And we would joke around, it's like that fine balance between religion and occult and community, right? So we had you all recite this credo and it was four or five values that we held true and we wanted everyone to kind of live and breathe. And that's probably in a weird way. I think I realized we don't need to make our members stand up every morning and recite those. And we've moved away from that at VFA as well, as far as I know. But that sort of something, that north star that we can all agree on that, yes, this is why we're here. Our backgrounds and our voices may look different, but we are all here because again, and the problem initially, when we first started was it's still really hard out there for women. How can we come together and have an abundance mindset together because to date, there's been too many places that we're in that has a scarcity mindset.

Sean Lane: So you mentioned that north star, one of my favorite parts, I've been spending a bunch of time on The Lola website, but one of my favorite parts is there's this description about your members, right? And so you know this, but I'm going to read it. Our members are purpose driven founders, freelancers, and creatives, corporate women, corporate expats from across industries. We are returners, some of us in our third and fourth careers. We're connectors, philanthropists, community activists, and so much more intentionally building the life and career we need to grow and thrive. So first of all, I think that description is amazing, but I would have to imagine you didn't just arrive at those three or four sentences. So how did you decide that was going to be your north star and that was going to be who you were for?

Eileen Lee: It didn't happen overnight. I think we struggled early days and I remember having strategy sessions because we were convinced that we were placed for corporate women. And my co- founder Martine spent 20 years working at Turner TNT TBS, so in corporate. So we both believed and agreed, corporate women need this. A lot of them don't know that they do, but they need it. So we were very much split in the beginning, almost three... A couple years later, the audience told us, who our core audience was, where our community is now majority founders and freelancers. So that is who we serve now. That is who we focus on. And then I like to joke around that the corporate women either couldn't find a way to engage because their companies take up so much head space, so they couldn't figure out a way to come into a physical space or join our digital community. But also a lot of those women have since left and the pandemic I'm sure has pushed them over the edge to do so, but a lot of... The way that the corporate structure kind of has them operate, they left and they started their own thing. So now they're part of the founder and freelancer bucket.

Sean Lane: It's admirable to me that both in the moment, and now looking back, Eileen can recognize that they were just plain wrong about who they thought this community was going to be for. Even the most perfectly laid plans can go awry. But I think you'll find to be a theme with Eileen, she listened to what her community was telling her, and she reacted accordingly. With her new target audience in mind, I was curious how, as a brand new resident of Atlanta, Eileen went about finding women to build out her new community.

Eileen Lee: Yeah. I mean, from the get go, we knew, especially being in a city like at Atlanta and it being, I think it's over 51%, the population is black. We knew we wanted our community population to reflect the diversity of the city. So early on we recruited ambassadors all women of color. And we said," Hey, our networks only go so far. Will you be open to opening up your networks, pitching and building brand awareness in hopes that we can get more diverse women across races into our community?" And that did some, and I think everybody knows with diversity or any DEI efforts, you can't just do one thing and be like," Cool. That's that check." So that was one of the first things we did. And again, we kept on listening. That's one of the other big take aways from VFA, just having an open mind and always the active listening. I remember we talked a lot about, but when we would go to visit the fellows in the different cities and the one weekend in Providence always comes to mind, we did the posted sessions of stop, start, continue, still do that. Love that exercise.

Sean Lane: Me too.

Eileen Lee: Some of the best ideas came out that start column that we would take back and implement the next day. I remember one was as simple as, have the fellows take over our social media, do like a social media takeover and see what it's like through the eyes of an actual fellow verses the team trying to figure out and talk at you all the time. So I definitely took that to The Lola while building the community. And it still happens. I had a session yesterday with some of our black female entrepreneurs and one of them threw out an idea. And I was like,"Oh my God, we would've never thought of that. That's amazing." And she was really sweet about it. She was like,"Yeah, it's a pretty good idea."

Sean Lane: And has that extended into what you offer to members, right? So, gathering those ambassadors or doing a start, stop, continue exercise, does that then shift also, not just who you want to bring into the community, but what the community might offer to them?

Eileen Lee: Yeah, absolutely. And part of our intentionally inclusive efforts is what we call it, about a year and a half ago, the thesis that we created behind that effort and supporting more black female entrepreneurs in our community, because Atlanta's chock full of them. The thesis was, if we can better support the most underserved and underrepresented amongst our community of professional women, which the underserved and most underrepresented are the black female entrepreneurs, then we will all benefit. So over the past year or so, we have really spent time to listen to them and figure out what are the challenges they have, what are the resources they need and how can we best support them? Because realistically, we're not an accelerator, we don't want to be. We're a community where we really value connections and how can we help curate those connections so you can thrive better in your business life, in your personal life, et cetera?

Sean Lane: Community that values connection. If Eileen and the team at The Lola were there to curate those connections, they had to figure out the needs of their specific community. What types of connections were valuable to her community members? I was curious what Eileen uncovered as she started to build this community from scratch.

Eileen Lee: When we looked at the landscape, even before we started The Lola there's so many women's organizations and groups, they tend to be pretty fragmented by industry, age and race. So we knew early on there's got to be value in cross industry connections and collaborations. You can learn so much from someone who's younger and older in different industries, across races. So I feel like that holds to be true. And if we are trying to support the most underserved, the black community, particularly in the Atlanta area, how can we expand their resources? How can we- And again, we're not looking to teach them courses or anything like that. How can we set up their support system and their tribes so they can be more successful? And one of the things that we learned, and again, it was just an anecdote that when we welcomed our 55 black entrepreneurs early last year, we matched them with, and you're going to laugh because I called them Sherpas, and it's such a inaudible from VFA. I didn't want them to be mentors, peer mentors didn't have a nice ring to it. So they were existing-

Sean Lane: I like Sherpas.

Eileen Lee: Yes, existing members in the community who were charged to welcome and shepherd these new members. So they could help figure out how to navigate the community, tap into different resources and events. And a handful of them, most of the Sherpas were white women in our community and when they were paired with these black female entrepreneurs, we saw this special thing happen where we were intentionally connecting to networks that would've never overlapped and the feedback that we got from both parties was this was not only career changing, but this was life changing for me. From The Lola member, the white woman's side, one of the anecdotes we got was," I've been doing this all wrong." She's an incredibly successful marketing executive. She's been mentoring tons of women behind her. And she learned through that as well as our anti- racism sort of community group we have that she has been trying to tell the younger folks she's been mentoring, what she thinks that she would've wanted to hear when she was their age. But the reality is if you're talking to a black woman, they have different lived experiences, so she's like," I've been doing this all wrong. I need to start over and figure out how I can better support all women, not just me when I was 20." So that was really valuable to hear. And then from our black members, truly the community and a sense of belonging, that was really our intention from the beginning. How do we make sure that we are an inclusive space that not only white women, Asian women, Latinx women, but also black women feel like," This is a space for me." And that is absolutely what we've heard. They've called our space, and when I say space, physical space and digital space, they said that it was a psychologically safe space for them. So that to me was a very meaningful data point.

Sean Lane: Yeah. I mean, even as you started to describe the Sherpa program, I mean, for me, I was thinking," Oh, I can see how that would be an amazing way to get them into the community, get them exposed to stuff faster than they would have without having that Sherpa." But wouldn't even have thought about those additional network effects that you just described. And so it's amazing that it becomes so much more than just about within the quote unquote four walls of The Lola, right? That level of not just acceleration for belonging in your community, but just in their entire career is probably not one of those things that you can put on the spreadsheet and measure, right?

Eileen Lee: No, not at all. And again, when I think back, because we're sort of, I'm trying to now put this experience over the VFA one. We did that for the fellows too. It was a more of a mentor program and some of those relationships, I believe still remain 10 years late, and to me that's where I get my kicks from community building, when you're able to make those connections that people are like," Oh my God, how did you know that we would hit it off?" I probably didn't but it's fun to connect and match folks.

Sean Lane: Can you talk a little bit more about that? Because I admire that about you, the patience that you have to see the fruits of that, right? You're literally talking about a decision you made 10 years ago, right? To match me with Dan Kelley from IAC, right? How do you think about that in terms of knowing that you're playing the long game, as opposed to like the instant gratification of like," Okay, this is done, I did good work. I'm moving onto the next thing."

Eileen Lee: I think that's the trickiest part of it. Because also some people don't tell you, some people are great of saying," Hey, by the way, I wanted to make sure you knew that this thing that happened brought me X, Y, and Z." But some people don't even mention it all and then I assume it was a total failure. But just the other day, this woman had never come into the physical space of The Lola, it had been a year. I assumed she wasn't getting anything out of it. And she came up to me and said," I have built so many friendships and relationships, I just haven't seen you or told you or answered any of your emails or messages." So again, I think it's really tricky from a metric standpoint, but in my mind over time, I particularly enjoy this matchmaking. I want to be clear. I don't think I would be a good matchmaker, but I have always, back in the VFA days, I remember, I don't know why I thought this was the solution, but I had two projectors going with spreadsheets of the fellows and our mentors. And I just sat there manually talking through and making matches based on... And it varies, common challenges and what the mentor's strengths were, personality, industry, whatever it was. And even to this day, I loosely do that. I always have a bad memory and I'm bad with names, I no longer can say that because I've been community building for 10 years. So I have a system in my head now, but yeah, I enjoy kind of thinking of two people, and if they haven't met that, I think that they would hit it off. I will tell you, there's probably, I'm trying to hot in the dark, maybe 30 to 40% success rate if you're looking at a group of like 50 or a hundred, it's a total crapshoot. So the success for even the 10% that will stay in touch for life is good enough for the-

Sean Lane: The longevity.

Eileen Lee: Yeah, for the 20%. I mean, we have some folks that six months into that partnership program, some woman said," Could I have another Sherpa? She never responded." And I looked to her and I said," Oh, I really wish you would've reached out and let me know." And she's like," You're busy. I didn't bother you." And that's the whole point of the program. So, always learning and figuring out how to best increase that percentage of success. We're dealing with people.

Sean Lane: It takes a special kind of person to have the patience and the persistence to curate connections like this. It's honestly incredible to me. On one end of the spectrum, Eileen makes matches that are," career changing and life changing." And on the other end of the spectrum, she never hears a word. What's crazier, some of those matches that are silent could also be going amazingly well. She puts her community members first and that couldn't be more evident. Throughout our conversation you've heard Eileen and I refer a couple times to both a physical and digital component of The Lola's offering. Like so many physical coworking spaces, the Lola was rocked by the pandemic just eight months after opening its doors in July of 2019. So I asked her, what is it like to try to build a brand new community in the middle of a pandemic?

Eileen Lee: Oh, it's so wild. I think, I immediately wished... I remember looking at my husband and saying," Why don't either of us have pandemic proof careers?" Because he works at a marketing agency and everyone kind of hit pause on work like that. It was scary at first. We very quickly pivoted to doing a hundred percent virtual. We launched our digital platform on Mighty Networks, which is a great digital community. But again, the trickiest thing is that we're working with human beings and it's not just... We're obviously providing a service, but their behaviors are constantly changing and evolving throughout the pandemic. So we want them to connect and engage in the community and they pay us for that. But it's so funny because a lot of people continue to pay, but we don't hear from them. They don't do anything. I always go back to it being a gym membership, because there's always people that pay for years and are too scared to cancel it or whatever. And I don't want us to be that, but in the beginning of the pandemic, everybody was just shocked and scared. So we were all gathering online. It was awesome. And then everyone late fall, 2020 experienced that Zoom fatigue. and so then nobody engaged. And so we were constantly evolving. I think it will continue to. I caught myself saying post pandemic and it's like," Oh we're not quite there yet." So I think it's even more important and integral for us to continue to listen because everyone's needs are changing. The future of work is changing. The way our members utilize our physical space is actually in fact changing as well. So just trying to stay nimble throughout all that.

Sean Lane: And so do you envision some kind of hybrid as the long term model for you guys?

Eileen Lee: Yeah. Our assumption early on, before we launched our physical space was that it's 5, 000 square feet over two floors. We thought that we'd maxed out at 350 members. We got to 400 really quickly shortly after we opened and didn't feel like we had reached capacity. So we wanted to see what 500 looks like. We're slowly working our way back to that number. But I'm already convinced because people who used to come five days a week no longer, because we have more flexibility in the way we work. So I think we could push it north of six, 700, maybe more. So I think from a business model standpoint, that's got a lot of opportunity for us. Yeah, I'm interested to see if that stays, if that sticks or if it continues to change.

Sean Lane: I feel like that's a whole new kind of cross section of the different types of people you have in your community too, right? I know for myself, we're digital first at Drift, but I happen to live somewhat close to one of our offices. So I go in once a week because I enjoy it, right? I like seeing people and I like doing some sort of big team thing once a quarter, once every other quarter basis. That gives me energy, but I know that's not everybody. And so I think that would be really interesting for communities like yours to figure out, okay, what is the makeup of our community in terms of the people who thrive off of that in person interaction versus the folks who only want to take advantage of those digital resources and to your point, could be digital only members of your community forever.

Eileen Lee: Yeah, absolutely. And I feel like people share this more easily since we started the pandemic, but being an introvert, I'm an extroverted introvert. So really being attuned to what kind of environment makes me thrive. I think that's really important. We have a upstairs distraction free library space for our introverts who don't want to be in like a coffee shop setting in our main area. So I think it's continuing to play off of that. Especially from a community standpoint, introvert generally, because there's a lot of different types, prefer more one- on- one connections so making sure we have those kind of options versus come to this big event, this wine tasting or something and be overwhelmed. So for sure, it's going to be really interesting.

Sean Lane: And I think too, if you like that library introvert setting and you don't necessarily have a physical space that you can work from on a daily basis, right? That's a perfect little niche to be able to fill that void for folks who might not have a space at home or have a bunch of roommates, right? There's just so many different possibilities that people might have in their personal life that would make a space like that way, way more welcoming and fit for what they need as opposed to the giant, loud, noisy networking office environment.

Eileen Lee: Yeah, absolutely. I think you're tapping into, yeah, I think all the folks who are trying to figure out what the future of work looks like, I think that's really, coffee shops, coworking spaces. I think that's all for sure, what that's going to look like is going to be really interesting.

Sean Lane: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months.

Eileen Lee: I feel like I wish I could give you a learning one. The one that sticks out is Vanishing Half by Brit Bennett and she's a black female author and it's around race and it talks about a white passing twin and one who's darker skin color, but very much as an Asian American and with all the sort of racial injustice, it's a good read for a different perspective on race and how that's perceived.

Sean Lane: Vanishing Half, you said?

Eileen Lee: Yep.

Sean Lane: Nice. All right. Favorite part about working in ops? I still consider you an ops.

Eileen Lee: Yeah. I still consider me an ops too. I think for me, for the first time in my career, I have enjoyed and I've learned the most figuring out how to apply DEI to operations. I think I'm a nerd where I love process, Trello boards, all the pieces of software, Airtable, but how do I track and very much what we talked about, how do I track our points and goals and successes as it relates to DEI.

Sean Lane: Cool. We'll have to have you back to do a whole episode just on that topic alone, I think.

Eileen Lee: Yeah.

Sean Lane: Least favorite part about working in ops?

Eileen Lee: Oh, it always takes a certain personality and it's very much so many thinkless things. As it relates to just people call it admin, all the stereotypes that we ops people are like," It's more than that." I think it still has somewhat of a mixed bag reputation.

Sean Lane: Someone who impacted you getting to the job you have today?

Eileen Lee: Oh man, this is the first person that popped into mind, but I was just telling you that I saw Charlie Kroll, he was a early board member at VFA talk and he actually gave me some really solid advice as I was transitioning from VFA to The Lola.

Sean Lane: And last one, one piece of advice for people who want to have your job someday?

Eileen Lee: Oh. Figure out if it's something that you thrive in, right? And I think, I'm sure a lot of people have said it as it relates to operations, it takes a certain personality to thrive in it. And it's managing a lot of different pieces. I think community building, similarly, it can be draining. So I think figuring out day to day, if it's something that really gives you energy versus drains you, I think that's really important to figure out.

Sean Lane: Thanks so much to Eileen Lee for joining us on this week's episode of operations and thanks to Dan Kelley for being my mentor all those years ago in the beginnings of Venture for America. If you like what you heard today, make sure you're subscribed to our show. A new episode comes out every other Friday and if you learn something from Eileen or from any of our episodes, make sure you leave us a review to let us know what you've learned. Leave us a review on Apple podcasts or wherever you get your podcasts. Six star reviews only. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.

DESCRIPTION

Ten years ago, I joined a newly-formed Fellowship program called Venture for America, a non-profit that takes recent grads and trains them as entrepreneurs to work at start-ups in lower-cost cities like Detroit, New Orleans, Cleveland, and Providence.

The Chief Operating Officer of the startup that was VFA and our guest today is Eileen Lee. Following six years running VFA, Eileen is once again putting her community-building chops to work as the co-founder of The Lola, a physical workspace and digital community for women.

In our conversation, Eileen teaches me about what it means to be a community builder, how she was initially wrong about The Lola’s target audience, and why the Start, Stop, Continue exercise is undefeated in surfacing the best ideas.

Key Points:

  • (1:32) Why Eileen wanted to start The Lola
  • (3:32) What is the community at The Lola?
  • (6:59) The learnings Eileen took from founding her first community, Venture for America (VFA)
  • (9:14) How Eileen determined The Lola’s “North Star” and who The Lola was for
  • (10:53) How Eileen found people to build out her new community in a new city
  • (14:24) How Eileen determined what her community needed
  • (19:18) Eileen’s thoughts on playing the long game vs. harnessing quick wins
  • (22:32) What it’s like to build a community amidst a pandemic
  • (24:28) The pros and cons of a hybrid work model
  • (27:49) Operations lightning round

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz and @DriftPodcasts.