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Think you know non-proft?

Non-profit owners, employees, donors, supporters—this week’s episode is for you! There are a lot of assumptions and stigmas surrounding non-profits and what it’s like to run them. This week’s guests debunk many of those, and show what has made theirs so successful for the last seven years.

We operate like a for-profit, but we are always mission driven.

Shawanda Mason-Moore & Jennifer HolderCo-Founders The Chattery


Running a Non-Profit like a For-Profit with Shawanda Mason-Moore & Jennifer Holder (The Chattery)


Katie Hankinson (00:01):

Hi, I’m Katie Hankinson.


Mickey Cloud (00:02):

And I’m Mickey Cloud.


Katie Hankinson (00:03):

Welcome to Building While Flying, a Sasha Group podcast where we interview business leaders about how they tackle challenges, stay resilient and navigate ever changing skies.


Mickey Cloud (00:21):

Shawanda and Jennifer, welcome to Building While Flying. Thanks so much for being our guest today.


Shawanda (00:25):

Thanks for having us.


Jennifer (00:26):

Thank you.


Mickey Cloud (00:27):

Awesome. So Jennifer and Shawanda founded The Chattery in 2014 to help Chattanooga area adults connect with one another, encourage each other’s passions. They developed their friendship under similar circumstances, first meeting as adults where Jennifer was Shawanda’s property manager. I’m sure there’s some stories there as well. And they both recently moved to Chattanooga at the time and while they had friends and family in town, they were looking for a place to belong. And so as their friendship group, sort of their idea for The Chattery to build a place for all adults to learn, connect, and grow. So I know that’s a quick little background, but I’d love for you guys maybe just start just by giving an overview of what The Chattery has become and where you guys are today.


Shawanda (01:07):

Yeah, so we are a nonprofit learning collective that offers fun, affordable and accessible classes for adults. So our classes can range from anywhere from cocktails and calligraphy to learning Excel and personal finances. And what started out as, I guess, sort of a side hustle I would say, for us, we both were working full-time jobs when we started it and hosted about four to five classes a month. Now, seven years later, it is our full-time job, but now we host 30 to 50 classes a month, just depending on what we have on the schedule. So yeah, it’s grown from just hosting a few classes a month to now a larger community, which is the goal of why we started this was to build a community of learners.


Mickey Cloud (01:59):

That’s awesome. And I guess I’d love to dive into just kind of what you just said, that building a community of learners. And I know you guys met kind of under interesting situation and that what you were looking for that kind of place to belong when you started the organization. But could you talk a little bit about why was it important to you to have a place like The Chattery that offers adult education and a space to connect around hobbies and passions, specifically in maybe a growing mid-sized market like Chattanooga?


Jennifer (02:29):

Sure. So it was important. So when we moved here, it was really difficult to find our people. I’m from Dayton, which is about 45 minutes away from Chattanooga. And I had friends living here, but I had changed. I had lived in New York and then New Zealand and then moved back here and I was a different person and well, I’m still friends with them. [inaudible 00:02:51] It just wasn’t that… A lot changed for all of us. As we grew up, we became different people basically. So finding that community here was really difficult. Shawanda and I talked about it a lot in our blossoming friendship, trying to find the people that we wanted to hang around with and grow with more. But so we had both taken… The way that we worked on finding community was we had both taken SpringBoard at the time.


Jennifer (03:27):

Now it’s CO.STARTERS. I took it through LAUNCH. Shawanda took it through CO.LAB. I took it to develop The Chattery and Shawanda took it for another business. But we kind of, from that, we recognized that learning was the way to connect those dots. And really, from there, it just grew where learning brought down the barrier of not knowing the other person, because you’re all kind of walking and being like, “Okay, maybe you could do one macrame knot. But none of us… We’re all novices.” And so you can learn together and you can joke when you mess something up. It’s all very… It’s a safe space, that was the word I was looking for. It’s a safe space to learn so that helps build community.


Shawanda (04:10):



Mickey Cloud (04:11):

So I was curious, and maybe this came out of your experience going through CO.STARTERS or that type of program, but I was curious, I guess, to learn why you’ve launched the company as a nonprofit versus an LLC and kind of what opportunities and challenges that has maybe presented as you’ve been building.


Jennifer (04:31):

Yeah, so we debated that for a very long time. So I had taken that CO.STARTERS… I mean at the time, SpringBoard class.


Mickey Cloud (04:40):



Jennifer (04:41):

The first year I was back and I don’t think we started The Chattery for another year and a half, two years until after.


Mickey Cloud (04:46):



Jennifer (04:46):

So we went back and forth, and back and forth, and back and forth. And ultimately, we decided that we wanted The Chattery to be a space for all, which meant that we wanted to provide more affordable/free learning for adults. Of course, the costs, we just try to keep them lower. We hire local community members to teach. And so we really focused on that portion. And with that too, we’re able to apply for grants to help bring in speakers. We brought in Austin Channing Brown a few years ago. We are looking forward to bringing in more people in the coming years, but that just provided more opportunities in that sense. I don’t know Shawanda if you have something to add to that.


Shawanda (05:27):

No. I always like how you answer that. So that’s how it’s like.


Jennifer (05:32):

I will say it was…


Mickey Cloud (05:32):

You’d say that one.


Jennifer (05:34):

It was a difficult decision.


Shawanda (05:34):



Jennifer (05:34):

And we’re asked that a lot, but really, it was just a decision that made the most sense for us. We both worked in nonprofits for a long time. We had a mission and it’s not like you can’t be a for-profit and have a mission.


Mickey Cloud (05:47):



Jennifer (05:47):

And also just because we’re a nonprofit, doesn’t mean that we don’t want to be profitable.


Mickey Cloud (05:53):



Jennifer (05:53):

It just means money stays within the nonprofit. We’re not trying to be [crosstalk 00:05:59] forever.


Mickey Cloud (05:58):

You’re charging for the classes. They are certainly revenue generating, what you’re doing.


Jennifer (06:04):

Opportunities. Exactly.


Shawanda (06:05):

Yeah. Exactly.


Jennifer (06:06):

And a lot of nonprofits are always looking for a social enterprise. Well, we are a social enterprise. That’s what we are. So we’re able to kind of continue to provide learning opportunities. We found really unique ways to do that.


Shawanda (06:17):

Yeah. And we run our nonprofit as if it is a for-profit.


Mickey Cloud (06:23):



Shawanda (06:24):

Like the mentality of it. And I think part of what we’ve discovered having worked at many nonprofits and now starting one is that there’s a stigma attached to a nonprofit that you should always be begging. You shouldn’t be making any money. And so Jennifer and I are sort of on our soap box about nonprofits don’t have to do that. And so we think strategically about how we want to run our nonprofit so that it’s successful. And part of that, yes, there is a fundraising strategy, but we also think about how we can monetize our space that we moved in. We think about how we can work with different local organizations and bigger brands and how we can work together to fulfill our mission. So yes, we are a nonprofit, but we do work as if we are a for-profit.


Mickey Cloud (07:12):

Right. Yeah. Could you talk more about that mission and just how you guys articulate it and how it informs kind of the classes you offer, the courses, the kind of the ways you are building The Chattery?


Shawanda (07:29):

Yeah. So our mission… I’m trying to think of where to start. So our goal is to create a community of learners, that’s the simple part of our mission. And so how we do that is we host a myriad of classes, workshops, and events. And so whenever we are putting together any type of event, a series or whatever, we’re always like, “Is this fulfilling our mission? Is this fulfilling our mission? Is it continuing to create the community that we want to do?” And so that’s a question that we ask ourselves whenever we are planning any type of class. And even with our events that we do, I think Jennifer and I always, we love hosting and planning events and some of them, from the surface, may not seem like they’re mission focused when we put our little themes on them.


Shawanda (08:20):

But everything that we do, whether it’s working with a local business that maybe you’ve never heard of before, or having a certain play… Everything that we do, we think about it so that when you’re coming and you’re having fun, there’s some type of learning element. Just recently, we hosted our first in-person event since March of 2020, and it was a market for Mother’s Day. And so just even things like that, like when we moved into our space, we knew that we wanted to host markets so that people could learn about different vendors. We had some pretty well-known to us vendors that set up shop with us, but there are a lot of people who maybe hadn’t heard of some of them. So we want to provide a space where people can learn and it doesn’t have to be in a traditional classroom setting.


Mickey Cloud (09:11):

Yeah. That’s awesome. You mentioned it started out as a side hustle, but it’s not going to fully blossom into your full-time gig. And so I guess we’d love to talk about that moment and the decision kind of making process behind that. Was there a catalyst that kind of led you all to have the conviction to make that leap and say, “All right. Let’s take this on full-time.”


Jennifer (09:34):

So yes, there was multiple catalysts, I would say. So I was working at a full-time. I was working a full-time job at a housing nonprofit here in Chattanooga. Shawanda was working part-time at another nonprofit and she also runs a blog, Eat. Drink. Frolic. So doing lots of things. And it was basically, we entered… One of the things is we had the opportunity to take part in Arts Forward Chattanooga, which was a collective of 18 different nonprofits, arts nonprofits that work together. And we had consultants who walked us through growing basically. And it was a lot of arts organizations that were our size that had been doing it for five years or less. We were at five years at that point.


Jennifer (10:20):

So we were accepted into the program and that was almost the kick that was like, “Okay. We now are… Little do they know, we now can…” We applied for a grant and we received it. And so that’s when I was like, “All right. Full-time job, bye.” And then I took a part-time job for one year. And when I walked in, I said, “This is lasting one year.” And then we worked that whole year for us to… And Shawanda and I both left our part-time nonprofit jobs at the same time so that’s been two years now.


Shawanda (10:55):

I don’t know what time is. Yeah. I think it’s in two years.


Jennifer (10:59):

I think.


Mickey Cloud (10:59):



Jennifer (11:01):

We skip 2020 sometimes. And sometimes, we [crosstalk 00:11:06].


Mickey Cloud (11:06):



Jennifer (11:06):

…because of it so it’s…


Mickey Cloud (11:06):

Well, let’s talk about that next, because you made that decision in 2019 and it became a full-time thing that you guys are building. And then one of the first things that happens is a global pandemic.


Jennifer (11:17):



Mickey Cloud (11:17):

And you guys are doing in-person events around learning and connecting and community. So when that first hit that last spring, how did you guys react? What was the kind of game plan and transition pivot opportunities you guys went after?


Jennifer (11:38):

Yeah. So… Oh.


Shawanda (11:40):

Oh. Go ahead.


Jennifer (11:42):

Go ahead. Well, four months… I would say four months before the pandemic, between us leaving our full-time jobs and the pandemic, we actually signed a three year lease on a space. So that’s a really big decision that we made and we crowdfunded for it through IFundWomen. We raised $32,000. We were so excited. Okay. And then I’ll let Shawanda take it from there when we pivoted.


Shawanda (12:04):

Should we insert doom music?


Mickey Cloud (12:06):

I’ll call on to Eric, yeah.


Shawanda (12:11):

So yeah, we…


Mickey Cloud (12:11):

Pam, pam, pam.


Shawanda (12:11):

Yeah, exactly. So, yeah, we raised, as Jennifer said, $32,000 in four weeks on IFundWomen to help us move into a bigger space, to continue with growing our community. We get the space. We find it. It’s awesome. I’m actually in it now. And then, we have to shut down. So we took a breath and said, “All right.” Also, I should also say I was seven months pregnant at the time.


Mickey Cloud (12:38):

Oh. Easy. Sure. Yeah.


Shawanda (12:41):

So everything was fine. Yeah. Nothing to worry about. So not only were we trying to plan for me having a baby and then trying to hire someone to help out Jennifer while I’m on maternity leave, but now we’re trying to figure out like, “Does our business even exist?” And so even though our business, yes, it thrives on in-person connection and that is why we created The Chattery, we did have an awesome opportunity which was to go virtual. Luckily, we have amazing teachers that we’ve built connections with who were on board. And so we logged on to Zoom like everyone else and said, “All right. Let’s try this online.” And we’ve spent the last year virtual and it’s so much fun.


Jennifer (13:24):

15 months. No. How many months? 14 months. 14 months we’ve been on Zoom.


Mickey Cloud (13:31):

Has there been any… Has it made it more accessible? Has there been any data that you’ve said that you’ve seen that says like, “Hey, maybe just going forward, we’re a hybrid model that has some in-person events, has some virtual events” or do you think you’ll go back to kind of the way it was?


Jennifer (13:46):

Yeah. So one of the other things we did at the beginning of the pandemic was a lot of our teachers were losing their jobs. So we kind of changed our pricing structure a little bit with teachers. And we also lowered our prices at the same time a little bit, just because also everyone else was losing their jobs.


Mickey Cloud (14:00):



Jennifer (14:00):

Unfortunately. And this is before any… And before there was a government response.


Mickey Cloud (14:05):



Jennifer (14:06):

So we changed a lot of things. So we did actually, we were able to lower the prices because you can get up to a hundred people just on the basic plan.


Mickey Cloud (14:14):



Jennifer (14:15):

Which is great. So we were able to get a lot more people coming on. And so that’s something that’s been really great. And we also have people from all over the country and world. So our very first class, we had someone from Scotland.


Mickey Cloud (14:32):

That’s amazing.


Jennifer (14:32):

It’s like, “Okay, great. Never had anybody from Scotland. Right?”


Mickey Cloud (14:36):

We’re now an international business. Yeah.


Shawanda (14:37):



Jennifer (14:37):

Exactly. Just like that overnight. Thanks COVID. But yeah, so that’s been a really cool thing is that we do have followers now that don’t live here and that hopefully, will one day come to Chattanooga and take an in-person class.


Shawanda (14:51):



Jennifer (14:51):

But we at least can see them online.


Shawanda (14:55):



Mickey Cloud (14:56):

Well that was…


Shawanda (14:57):

And we’re…


Mickey Cloud (14:57):

Oh, go ahead, Shawanda.


Shawanda (14:58):

I was going to say we’re planning… Like we said, we’re going back in-person. Actually, our first outdoor classes are launching in a couple of days… Wait, what is today? Friday.


Jennifer (15:09):



Mickey Cloud (15:09):

Yeah. Soon.


Shawanda (15:09):

Saturday. Tomorrow. We’re launching soon. But there is an element of our business that we will keep online and what that looks like, we’re still figuring it out. But as tough as it was the last year, I think COVID did have some opportunities, like Jennifer said, for us to have someone from Scotland. We had someone from FIT come to a class. So there are some opportunities there, and if we are glass half full people…


Jennifer (15:37):

Are we?


Shawanda (15:38):

Insert eye roll. [crosstalk 00:15:40].


Jennifer (15:41):

Are we supposed to be?


Shawanda (15:45):

There are ways that we can still optimize those opportunities. And I think there are some good things that’ll happen from us having some classes online, but we are very excited to get back in person.


Jennifer (15:57):



Mickey Cloud (15:57):



Jennifer (15:58):

And we had somebody from IFundWomen speak from New York, so that was great. Our original plan was to bring them here for Startup Week Chattanooga, but it didn’t work out. But we were able to bring her virtually. And then also we have a teacher now in Utah, a teacher in Texas, a few teachers in Nashville so we actually could expand our teacher base too.


Mickey Cloud (16:18):



Jennifer (16:20):

We’re just trying to take advantage of all the opportunities.


Mickey Cloud (16:24):

And one of those opportunities I know is also the kits that you started selling, that kind of at-home kits. So could you talk a little bit about where those came from and how those are doing kind of in the portfolio of offerings?


Jennifer (16:35):



Shawanda (16:36):

Yeah. So that was another idea that came out of, “Okay. We’re online. How do we continue to try to make this business work? Okay. Kits.” And the kits were to continue to encourage people to learn at home. We didn’t know how long we were going to be virtual. And so when you’re sitting in front of a laptop all day, it gets really monotonous and just boring. And so the kits are a fun way that you can sit at home with your quarantine friends and do a macrame or whatever it is.


Shawanda (17:12):

And so with the kits, we’ve also started to develop themed kits. So for Black History Month, we had one featuring black owned businesses that focus on self-care. We’ve had obviously ones for Mother’s Day, which were really cool. I think Jennifer and I, we’re planners and we love brainstorming and thinking of things. So that part has been sort of fun just to think of the different kits outside of the ones that accompany classes that we can do. So we’re working on one for Juneteenth soon, which will be awesome as well. So I think that’s also another part of our business that might stick around.


Mickey Cloud (17:53):

Do you have a favorite kit or online class or bestsellers that you guys are particularly excited about?


Shawanda (18:01):

Well, I’ll say the self-care, the one featuring the black home businesses, sold out within a day or two.


Mickey Cloud (18:08):



Shawanda (18:08):

We had all this marketing plan surrounding it that we didn’t even really get to do because they’re like, “Oh, they all sold out.” And that was a fun one to put together. And I think it was one that was needed. We needed self-care, but we also needed to see these awesome black businesses be put together and this awesome kit to teach people self-care. No matter who you are, self-care is important, especially during this year that we’ve had. So that box has prompted us also to think about Juneteenth and what we can do with that box as well. I don’t know if Jennifer has another one.


Jennifer (18:42):

So class-wise, we did a whole series called the Jumpstart Series that was for artists and arts organizations. And it was 30 free classes on everything from product photography to bookkeeping. And so that was really great. It was great to have people participate in that and learn from that. But our most popular online classes, it’s always hand lettering, but the other one is cocktails. So we worked with the Bitter Bottle, which is local. She makes bitters here in Chattanooga and so she’s actually about to drop off some boxes on my porch right now for tonight’s class. But so she was able to package little bottles as a box and so that’s been really popular. And it’s been really fun to see people get on. We had a really big crowd for Valentine’s Day.


Mickey Cloud (19:31):

[crosstalk 00:19:31]


Jennifer (19:31):

And get on and everybody’s videos on and everybody’s drinking safely at home.


Mickey Cloud (19:36):



Jennifer (19:36):

Honestly, we’re not bearing the liability of that.


Mickey Cloud (19:39):



Jennifer (19:39):

So that’s my favorite class. My favorite online class because you’re at home and you’re not driving anywhere else. That’s great.


Mickey Cloud (19:45):

Yeah. Wow. Well, you’ve both mentioned fundraising through kind of some national organizations like IFundWomen and some of the grants that you guys have gone after. I know you got a grant from Sara Blakely’s Red Backpack Fund. And you both have nonprofit experience so I’m sure that has factored into this, but I’m curious for the nonprofits that are out there that are listening, when it comes to kind of how do you evaluate your time and energy and what you’re going to go after from a grant writing perspective or from a fundraising activities perspective, would love to know about what your process is there.


Shawanda (20:20):

Yeah. We would like to know as well.


Jennifer (20:25):

I was going to say… I was going to say we have wasted our time on some grants. And I think at the end of the day, even if you’ve met with the people and they say, “Yeah. Apply.” But if you’re still having a reservation, maybe if it’s a really complicated grant, maybe don’t apply, unless it seems really positive. I don’t know how else to say that. I’m not saying it very well, but like [crosstalk 00:20:50]


Shawanda (20:50):

Yeah. Every grant opportunity we’ve learned is not worth our time, no matter how much we need or want the money, whatever the amount, whether it’s 5,000 or 50,000, I think we have to sort… And now we’re the queens of beginning and starting spreadsheets. So now we have a new spreadsheet of grants, grant opportunities. We look at a few things like the date, like when is it due? Do we even have time on top of what we’re already doing? And then we have a husband too. Do we even know who they are? Because we’re [inaudible 00:21:25].


Shawanda (21:28):

It’s just I think people, especially in the nonprofit world, we stress ourselves out because we’re always trying to apply for more grants, apply for more grants, we need more operational support. And that is true. But like Jennifer said, we have definitely wasted our time on some grants. And I think just learning from it, and it’s funny, the ones that we haven’t stressed over, like even the Sara Blakely Grant.


Mickey Cloud (21:51):



Shawanda (21:52):

It was a great opportunity. Multiple people sent it to us to say, “Hey, you guys should apply for this.” So we took a stab at it and got it. We were out of 75,000 people, or however many of us, we were a thousand, I think. I don’t know.


Jennifer (22:06):

Right. They only selected a thousand.


Shawanda (22:07):



Jennifer (22:07):

And we were in the first round too. So we were selected at the beginning.


Shawanda (22:10):

Yeah. And so I think we just have to choose our [crosstalk 00:22:15].


Mickey Cloud (22:15):

So it sounds like it’s a little bit of… So it sounds like it’s a little bit of just opportunity costs and time and evaluating that.


Jennifer (22:21):



Mickey Cloud (22:21):

But then also having a running list of criteria that maybe it has to work on that it make a call on, it’s worth our effort putting it in.


Jennifer (22:31):

Well, and never invent a program. That’s my number one advice. Never ever invent a program for a grant. That is a huge mistake. If it doesn’t apply to you, it doesn’t apply to you. Just remember maybe that grant’s yearly and if something comes up during the year, you can always apply for it next year. But we’ve even had grant opportunities that are like, “Well, if you change your mission.” I was like, “We’re not going to change our mission for a grant. This is who we are.” So it’s being firm in who you are and just realizing you’re not going to fit in everything. And I think too, going back to money and nonprofit versus for-profit.


Mickey Cloud (23:03):



Jennifer (23:03):

We operate like a for-profit, but we also are always mission-driven. So we’re never going to go after money. We’re never going to go after a sale, whatever it is, I’m trying to apply that to both for-profit, nonprofit.


Mickey Cloud (23:15):



Jennifer (23:16):

Just for money, because that’s going to ruin the integrity of our nonprofit and what we do every day. So yeah.


Mickey Cloud (23:24):

Awesome. That’s super helpful.


Jennifer (23:25):

That’s how we feel about grants.


Mickey Cloud (23:26):

Yeah. No, no. It’s super helpful.


Jennifer (23:30):



Mickey Cloud (23:30):

And so I guess I’d love to know about as you’re starting to get back in person, you’re starting to kind of come… We’re coming out of the pandemic, hopefully. What are kind of growth plans from here? What’s next for The Chattery?


Shawanda (23:45):

Yeah. So definitely, we want to continue to grow our menu of classes, but I think one of the things that’s really important to us is to continue our work with having learning opportunities around the subject of social justice, gender equality, LGBTQ learning opportunities. We’ve done some of those, but I think we have an opportunity to dive deeper into that work. And as Jennifer said in 2019, I think it was 2019, we brought in Austin Channing Brown to Chattanooga to do sort of a free workshop on her bestselling book, I’m Still Here: Black Dignity in a World Made for Whiteness. And so that sort of lit a fire under both of us to continue that work, and then the pandemic happened. But I think that’s something that is on our radar almost immediately that we’re starting to work on. So in addition to having classes where people can come and make art, or you can come and learn more about your personal finances, we want to have these classes where people can sort of be a better human.


Mickey Cloud (24:53):



Shawanda (24:54):

So that’s something that is immediate on the horizon.


Mickey Cloud (25:00):



Jennifer (25:00):

Yeah. And I think too, we recently had a conversation with someone who’s kind of mentoring us. He mentioned that in this past year, we’ve changed so much, not only just because of the pandemic, but Shawanda became a mother. And so there’s all this stuff about us personally that’s changed. And so I’m excited. We’re planning to sit down and figure out… This organization is always about the community, but also we’re definitely part of that process.


Mickey Cloud (25:24):



Jennifer (25:25):

And we infuse ourselves into a lot of what we do. And so I’m excited to figure out how have we changed personally? How has our business changed? How is our business going to change in the future? Because everything’s going to be different. So I’m the most excited about planning because we’re planning about…


Mickey Cloud (25:39):

Yeah. Awesome.


Jennifer (25:42):

That type A.


Mickey Cloud (25:43):

Wow. Well, the planning side of this, I’ll be curious, this last kind of question, we love this Building While Flying analogy, because as entrepreneurs, you kind of know you need the nimbleness, the flexibility, the foresight in order to operate but also those pilots are kind of renowned for their in-flight checklist. So when things go awry, they are trained to keep calm under pressure. So I’d love to know what your internal kind of checklists are when you’ve got kind of backed against the wall or you’ve got to make a tough decision, how do you kind of keep calm and what’s the process that helps you get through it?


Shawanda (26:18):

Yeah. I think one of the things that we do is we like… Which I don’t know the opposite. I don’t know. We leave it alone for a minute. So if we don’t know what to do or how to handle something, what should we do, we both are sort of like, “Let’s just come back to it.” And I think there’s something to that. Again, you feel like there’s this immense pressure to make decisions all the time. And so for us, it helps to not make a decision, especially when you’re feeling a little stressed or whatever. We sort of were just like, “All right. Let’s move on to something else.” And then we were seeing today if one of us brings it up, then we bring it up. But not… I don’t know how that would work if you’re flying a plane but…


Mickey Cloud (27:05):

Well, awesome. Well, thanks so much Shawanda and Jennifer for joining us on Building While Flying today. You guys have been great guests and I’m super excited for what’s next with The Chattery.


Shawanda (27:13):

Yeah. Thank you. Thanks for having us.


Jennifer (27:14):

Thanks for having us.


Katie Hankinson (27:17):

Well, now that we’ve finished that thoroughly interesting interview, we’re getting ready to land, but before we do, Mickey and I caught up on some of the themes and topics that stuck out to us.


Mickey Cloud (27:27):

Yes, we liken this to the post-game show where we break down the key lessons we all can benefit from, including us here at the Sasha Group. Here is the Sasha Sidebar.


Mickey Cloud (27:42):

All right. Well, on today’s Sasha Sidebar, we have a little bit of a special guest for you. Katie is on vacation today and we have Kate Robertson who is a long time VaynerMedia Sasha Group employee, what, six years this summer, Kate?


Kate Robertson (27:54):

Mm-hmm (affirmative). Six years in July.


Mickey Cloud (27:56):

Amazing. Kate has done everything from community management to copywriting to now is working on some internal training and kind of… As well as our education team, our training team and all things, kind of still work for these, all the work that we do. So Kate, so glad to have you on.


Kate Robertson (28:15):

Thanks for reaching out. Happy to be here.


Mickey Cloud (28:17):

Yeah. And Kate, you actually really want to introduce me to Shawanda and Jennifer from The Chattery, so maybe you could start by just giving a little bit of the story how you guys met.


Kate Robertson (28:26):

Yeah. So I met Shawanda first in 2017, somewhere around there. We are both food bloggers outside of our full-time jobs and we met as judges at a local food competition.


Mickey Cloud (28:46):



Kate Robertson (28:46):

She was one that I had seen on Instagram and then we met in person and I was like, “Okay. So I put a name to a face.”


Mickey Cloud (28:54):



Kate Robertson (28:55):

And then I had a short-lived podcast for a little while.


Mickey Cloud (28:58):



Kate Robertson (28:58):

And I had her on my podcast in the first… She was one of my first 10 episodes or something.


Mickey Cloud (29:05):



Kate Robertson (29:06):

And we had this moment in the episode, we’re like, “Wait, we know each other. We’ve met before.” Because that would have been two years after…


Mickey Cloud (29:16):



Kate Robertson (29:16):

…that we first met at that food judging thing. And then I met Jennifer through her and have just come to know them and admire them and everything that they’re doing with The Chattery. So was super happy to make that intro.


Mickey Cloud (29:29):

Yeah. Yeah. And you’ve taken a couple of The Chattery classes.


Kate Robertson (29:34):

Mm-hmm (affirmative).


Mickey Cloud (29:34):

But what class did you take and what was that experience on the customer front?


Kate Robertson (29:39):

I took a calligraphy class a few years ago and I was just at a point in my life where I was like, “I’m ready to try something new.” And I’d always admired pretty handwriting and my mom has the most beautiful cursive, almost calligraphy everyday handwriting. So I was like, “Oh, calligraphy, that sounds fun. I’ll take it.” And I was not very good at it. There are a lot of rules with calligraphy in how you have to hold the pen and the size that everything has to be, and the proportions. And it was just not as free flowing as my spirit is so it was lovely. The teacher was awesome. It was 15 people or something like that in the class. And we got to take home our pen and the little worksheets and tracing papers. So I definitely learned a lot.


Mickey Cloud (30:28):

It sounds like you were in the mindset that kind of exactly is what The Chattery is built for. Right?


Kate Robertson (30:32):

Mm-hmm (affirmative).


Mickey Cloud (30:33):

Someone who’s like, “I just want to learn something new.”


Kate Robertson (30:35):



Mickey Cloud (30:36):

And that’s what The Chattery is there for. So yeah. So yeah, having listened back to the episode, be curious kind of what your thoughts, what are the highlights from the conversation for you?


Kate Robertson (30:47):

So for me, it was really interesting listening to them talk about The Chattery in a situation with you because the conversations that I’ve had with them have been just very different in general. And it was interesting to hear them really dive into starting their business as a nonprofit versus an LLC, which is something that I never knew. And it was just interesting their mindset or the thought process that went into deciding to go nonprofit or LLC and how they talk about like, “We are a nonprofit, but we operate like a for-profit business.” Because at the end of the day, they’re a business. They still have to make money. But letting or having their business as a nonprofit lets them keep it truly affordable and accessible for so many people.


Mickey Cloud (31:38):

Yeah. It’s also about creating that community of learners and not just something that only is accessible, like you said, to certain people and so. But they run it very much like “We’re going to sell things and we’re going to make money by selling things and we’re not going to have to beg for money.” It’s almost like a mentality thing that they’re running it like a for-profit, but it’s not… Operationally, I’m sure there’s some things they’re probably doing that maybe the average nonprofit isn’t, but it almost… They talked less about that and more about just the mindset that they bring to running it like a for-profit.


Kate Robertson (32:15):

And they have a board as well that is involved in big decisions and things like that. So that’s another thing that I think is really cool about them is that they do have a board.


Mickey Cloud (32:26):

Yeah. I think one of the… They also kind of talked about in the fundraising and kind of grant writing world, by putting for-profit hat on when they’re running things or that mentality, they’re more discerning when it comes to what grants are going to go after. They talked about never invent a program just to apply for a grant. It’s like yeah, you would never create an offering as a business just so a bank would give you a line of credit or something like that.


Kate Robertson (32:59):



Mickey Cloud (33:00):

It’s got to make sense for the business. And therefore, it’s got to make sense for the mission that The Chattery is after.


Kate Robertson (33:07):

Or like for us, we never invent an offering just to get one client. Right?


Mickey Cloud (33:11):

Right. Right. No, yeah. It’s got to be something that makes sense for the business. So I appreciate you making the intro to them. Do you have a… We always, at the end of the episodes, like to ask kind of a question of the episode of the day, kind of something for folks to chew on after the episode. What do you think we should ask the audience after this one?


Kate Robertson (33:34):

I feel like something nonprofit related.


Mickey Cloud (33:36):



Kate Robertson (33:37):

Or maybe about what’s one thing or one skill you’ve always wanted to learn, but you never have?


Mickey Cloud (33:44):

Oh, I like that lean into what The Chattery offers. Yeah. What’s something you want to learn even maybe as an adult, but maybe not even related to your career, but just something that you want to take on and learn? Awesome.


Kate Robertson (33:57):

That sounds good. Let’s go with that.


Mickey Cloud (33:59):

Let’s go with that. Awesome, Kate. Well, thanks so much for joining Building While Flying today, and we’ll talk to you soon.


Kate Robertson (34:04):

Thank you.


Mickey Cloud (34:06):

Thanks for joining us again, and for Building While Flying with the Sasha Group today. I hope you learned as much as we did. We’ll meet you right back here next time for another flight. If you’d like to hear more about how business owners and brands are navigating these times, tune into the next episode. And if you’re so kind, please rate and review us, plus we’d love feedback so let us know what you think, what you’d like us to dig into next on Building While Flying across brands, businesses, marketing, and more.


Katie Hankinson (34:32):

Original music by Fulton Street Music Group.

Welcome to Building While Flying!

This weekly podcast is brought to you by Sasha Group. We’re the consultancy meets agency arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding media and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Our pilots, Katie Hankinson and Mickey Cloud, will be talking to a diverse range of business leaders and founders. They’ll explore how these guests tackle various challenges while staying resilient and committed to growth. Through these real-life examples of strategies put into practice, we hope to inspire you to experiment and develop your own strategies as we all navigate these uncertain times together.

Shawanda Mason-Moore and Jennifer Holder launched The Chattery in 2014 to fulfill a community need—and one of their own.

As friends who were both new to Chattanooga, they sought a community, a place where adults could learn, grow, and connect. In 2014, they launched The Chattery, a non-profit that makes adult learning accessible, affordable, and fun. Over the last seven years, they’ve hosted thousands of classes led by hundreds of community members, fostered countless relationships, and created a welcoming, safe space for everyone to learn and grow. And they’re just getting started!


In this week’s episode, Shawanda and Jennifer share The Chattery’s origin story and mission, and explain how their mission drives everything they do—from the classes they offer to the grants they apply for. They also explain how they run their non-profit like a for-profit business (and why that’s okay), and why you should be picky when choosing grants. They also discuss how they pivoted during the COVID-19 pandemic, and which of their pivots will be sticking around.

Other in-flight topics:

  • Starting a business as a non-profit vs. LLC
  • Building friendships and community for adults
  • Staying true to your mission
  • Transitioning to online and at-home programming
  • Opportunity costs of applying for grants
  • Preparing for a hybrid model future

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Chattanooga, TN
Los Angeles, CA