Natalie Dean, Founder of Whine & Cheese, Inc.

Hi, Natalie! So let’s start with your “9-5” job. What do you do for a living?  

Hi! So full-time I work for the American Federation of Teachers, which is a teachers union based in Washington, D.C. Specifically, I engage our more than 3,000 local affiliates on a special project called Share My Lesson, a website where we give educators free resources to be able to successfully teach, manage, and work with students and make sure they’re successful.

My background is in corporate and crisis public relations. For about eight years of my career, I worked at fast-paced PR firms. When you’re fresh out of college and working in corporate and crisis PR it can be very overwhelming. I remember having to have two Blackberrys at the time, and having to take my work Blackberry on vacation with me. So, you know, when you first start in your career in your early twenties, that’s exciting, right? “Oh, I got an extra Blackberry. I’m traveling for work and I’m employed by the top PR firm and get to work with these major brands.” Then, a few years in, you start to experience burnout, and you think, wait a minute, is this really my dream job? But I felt that I had to take on that persona of having it all together, or to at least look like I do. Because I was too young to look burnt out, plus I was one of very few Black women, the youngest one on my team, and I worked for one of the highest-ranking Black women in that particular office and didn’t want to let her down. I was going to grad school at night. I was in a new city. So I could not fail.

Right. So many people can relate to that, I think. Especially Black women. The “work twice as hard” mentality. 

Right, and so what happened —  I would keep a space heater at my desk and one day I went to bend down to turn it on, and I was in so much pain. I went to the doctor, and she couldn’t figure it out — she thought I pulled a muscle. So she sent me to physical therapy and on the very first session, my physical therapist is like massaging my back and asking me what’s going on in my life. I’m telling her about my job, and grad school, and that I’m trying to buy a house. I’m just going down the list. And she’s like, “Oh, that’s awesome but, um, this isn’t a pulled muscle. This stress is manifesting in your body as this pain you’re feeling.” That’s when I realized, wow — I thought I was doing a good job making it look like I have it all together. But on the inside, my body is screaming, No, you don’t girl! That’s when I decided, maybe I need to start looking at a position that doesn’t require so much of my time. I ended up at an education startup that needed a PR manager. The startup was jointly owned by the Teachers Union and that was the start of my transition.

And so from there, how did your nonprofit Whine & Cheese come about? 

In the midst of that transition I realized how stressed I was, but had been holding it in. I started having conversations with friends and admitting how I felt. Slowly but surely they started admitting the same. Like, girl, adulting is not what I thought it would be! (laughs) This whole job thing is way more stressful than I imagined. I thought I was more prepared! And I realized that while our experiences may not have been identical, the emotions behind them were. So I said, okay, these are conversations that I’ve been having with friends that live in different cities. But I know I need women here in my area, so that we can get together and safely say — sometimes with our words, other times with just a look or a sigh — “I’m struggling. I need help.” And to also say to my network that their support is valued and important to me. And to be able to give the gift of community to each other. So I started an organization called Whine & Cheese, a forum where we could express, reflect and reset without pretense. 

That’s incredible. And how would you describe the evolution of Whine & Cheese over time to what it is today? 

It actually didn’t start as an organization. It started as a casual girl’s night in. I invited a few friends and asked everyone to bring a plus one, if they wanted. We all got together in my girlfriend’s living room. I decided that it was not going to turn into a pity party. So while we were definitely going to complain about all that was going on, we were also going to counter those emotions by recognizing and verbalizing all the ways and reasons we still had to be grateful. So we whined, but then we also cheesed or, you know, named things that made us smile.

I love that! And I’m embarrassed to say I didn’t connect the “cheese”  part of the name until just now. (laughs) So let’s sit with this for a second. Can you describe a little bit more about how some of the first Whine & Cheese sessions went? And when did you decide, oh, this could be a thing? 

So you’re asking me to think back ten years. (laughs) But that first night, and remember it was a group of 11 of us and I had probably invited five. And then, some people brought a plus one.

Right, yeah. 

So, there were familiar faces, but we didn’t all know each other. And that actually provided a space for us to be even more open with one another. The first few gatherings, we went deep. We shed tears, we prayed, we held hands. And it was like, Oh my gosh, this was the relief that I didn’t know I needed. So we started doing that every month, or every other month. There was no real formality to it. Our attire was very “show up as you are.” Like, you don’t have to get cute. This is an opportunity for you to let your hair down. So I also think that helped with the atmosphere of people feeling comfortable.

We were doing that for a couple of months and then, I was on the phone with a girlfriend of mine in New York and I was telling her about it and just how helpful it had been. And she said, “Oh, I want to start that in New York.” And I was like, uh no, it’s mine. (laughs) And then it couldn’t have been a day or two when God was like, how could you see how beneficial this has been for the women that you’ve been getting together with and not share this with other women? It was as though He was saying, like, how dare you? So I said okay, I hear you loud and clear. I put a format together. The main rule is that you start with your whine and you end with your cheese. So we’re always ending in a space of gratitude. And I called my friend back up and I said, “Here it is, it’s yours. Run with it!” And since then, she told a friend who lived in Charlotte, who told a friend who lived in Atlanta. And well, we’ve launched over 30 branches since. 

Wow! Congratulations.

Thank you! Thank you. It’s interesting because we’ve really not done a lot of promotion. Everything has been organic. It’s been a lot of word of mouth, which confirms for me that this is a need that women have. And initially, it was all women, whoever wanted to join. At some point, though, I had to acknowledge that the women who were showing up were Black women, between the ages of 25 and 40 at the time. They were the ones who needed this space the most. For a long time, I was hesitant about saying this is an organization for Black women because I didn’t want it to feel exclusive. But at the end of the day, this is who is showing up. So why not create a space that calls us out and calls us in?

Yes. That is so awesome. And is it still, I mean, if someone else were to show up, I’m just curious…?

They’re welcome, but with an understanding of the space. . .I’m trying to figure out how to word this. You are welcomed as a woman, but most of the resources and the conversations are geared toward those who identify as Black women. So if you can find your footing in this space — the way Black people have had to for so long — then you are more than welcome. But I decided to be true to the women who showed up for this. as our membership evolves, our offerings will reflect that, but for now this is what it is. 

Right. And so how did you come into the role of spacemaker?  It can be very hard to do. There’s a delicate way of having to kind of manage different personalities and needs. What do you think prepared you to step into that role?

I wish I had a really good answer for you on that one. It’s  like the Maybelline tag line, you know. Maybe she’s born with it. (laughs) I feel like, you know, innately since I was a young girl, I’ve been a connector. I’m very much introverted, but when I find my people, I turn up and turn on. When I like your energy, I’m just like, come be a part of my people. I just adopt friends and family along the way. I think that part of me has also translated into professional spaces. I’m the colleague who, people — specifically Black women, but, others as well — will come to and say, “Hey, do you have five minutes? I just need to think through this idea.” Or, you know, “I need another perspective on this.” And it’ll become a closed door, hour-long conversation by the time we’re done. So I can’t pinpoint what prepared me for Whine & Cheese other than God and what He placed in me, you know? 

What do you think you’ve personally gained from Whine & Cheese, as a participant?

Oh, gosh. It has given me some amazing relationships. The very first branch that I launched, we were together for six and a half years before there were life changes and relocations. And then, I ended up starting another branch. So, as a participant it’s given me lifelong friendships and bonds. Your friendships are a reflection of who you are, and usually you pick friends that feel safe or that you share some commonalities. But to be able to connect organically with women who you may not have been friends with otherwise, I think has given me a greater perspective and understanding of myself, and opened me up to new and unexpected things. These women have been able to pour into me in a way that I have just never felt before. And that’s not a knock to my day one friends, but there’s something special about being able to form friendships as adult women.

Yes! Yes, that’s so tough!

And, you know, there’s no pretense with Whine & Cheese. There’s no, what can you do for me? It’s just, I want to see you win, sis. And that gives me a renewed hope. When I see that among women — who I believe are the head of society, the changemakers — I get a renewed hope for what this world can be. And, then, I’ve been introduced to so many other gifts and talents that either they poured out, or that have been brought out of me. And just having this cheerleading squad. There’s a  whole list of benefits.

Incredible. I mean, what a wonderful space you’ve created. So, how can women get involved? 

That’s a good question. So to join Whine and Cheese is very simple. Just go to our website https://foreverywhine.org/, and sign up. In light of the pandemic and other life changes that have kept us apart, I've been searching for a way to bring us all together on a safe, yet personal level. So recently, we launched a mobile app to connect women in the same area and around the country. We’re a non-profit organization now, which I decided to incorporate in 2014, so a portion of the membership fee is tax deductible. Once it’s safe, if members want to start a branch, or small group, with other members in their city, that’s certainly an option and points back to the foundation of our organization — being able to move away from the screen and interact in person. 

Once someone decides they want to start a branch, I would schedule a call with her to be sure that this is the right fit. Not so much to vet them, but because there is a responsibility one must have to the collective when deciding to facilitate a safe space for women. So we’ll have a conversation, and then I’ll walk them through the very easy process of getting started. I literally have a framework for them to follow. Within the app, we share everything from funny memes and songs that get us amped, to affirmations and daily devotionals. We host regular events via Zoom that help achieve our personal and professional goals and we also have an annual retreat where we can get together for a long weekend to bond and build community. The last retreat was in this beautiful 15-bedroom villa in Orlando. We had so much fun! So after the country tackles the Coronavirus, we will be planning the next one. So yeah, that’s how it works!

Wonderful. This was incredible and I’m so impressed with what you’ve built and how you’re managing it. Thank you so much for sharing, Natalie!

Of course. Thank you!

Natalie (center) and members of Whine & Cheese.

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Alison Brock McGill, Nonprofit Strategist and Entrepreneur

Hi, Alison! Thank you for doing this interview. Can you share what you do?

I try to succinctly say that I’m a nonprofit consultant. In reality, that can mean a variety of things. At a high level, I work with nonprofit organizations to address any number of problems or areas for opportunity. I got into this work independently when I left a job in corporate social responsibility (CSR) and ventured out on my own in 2016. I started working with small-scale, nonprofit organizations focusing on fundraising and development, capacity-building, strategy, and growth. Over time, one of those client projects evolved into a full time opportunity. 

I’m now working full time as a consultant at Promise54, a talent solutions and advising firm within the education space. We work with all players within that landscape, including charter schools, district school systems, family foundations, and education nonprofits. Primarily we focus on talent-related issues, approached through a lens for diversity, equity, and inclusion (DEI). So that looks like anything from performance management, developing competencies, assessing compensation, and also thinking about DEI belief statements, strategies, and capacity-building. We take on a variety of projects for a variety of clients. It is a startup nonprofit, which has unexpectedly been my wheelhouse for the past three years. 

When you reflect back, was there a pivotal point where you made the decision to focus your career on nonprofit or service-based work? 

It was around the time I was considering applying to business school, which was in 2008 or 2009. I was living in Atlanta, working at Cartoon Network in a very different capacity than what I do now. It was a for-profit company, doing for-profit work. I had a lot going on in my personal life, and realized I wanted to do things I believe are fulfilling. 

My grandmother — my father’s mother — was living in a nursing home and dealing with early-stage dementia. I was visiting her once a week, and I struggled with losing her mentally. I was mentoring this girl through Big Brothers Big Sisters. Her name was Diamond. I was feeling very exposed to how different her upbringing was from my own. My mother was diagnosed with stage 4 non-Hodgkin's lymphoma, and so I got involved in the Leukemia & Lymphoma Society as a volunteer. I was also training for half-marathons. 

So I would be at my desk, and although I should have been working, I was actually planning fundraisers, organizing activities for me and Diamond, or coordinating with my uncle around when I’d see my grandmother next. So I was doing things that I felt were making a difference in the lives of people close to me. I was supporting another nonprofit in Atlanta called The Jerusalem House, that was doing a lot of work for homeless families dealing with AIDS. This ended up being what I discussed in business applications — wanting to create change. 

I joined Management Leadership for Tomorrow [MLT], which really helped me hone my story. When I went to Haas Business School, I concentrated on social impact and marketing. My first job out of school was in CSR, and from there I moved into nonprofit consulting. 

Did you have any individuals or any organizations who were especially supportive to you along the way? 

MLT was super helpful. My cohort would have monthly sessions with a coach to help process what was going on internally and to get that thinking on paper for our business school applications. So we would have a number of homework assignments that we had to bring to coaching calls and if you had done the homework then the coaching calls were great. I trusted the process, so if they said to write journal entries every month, then I would do it and it wound up being helpful. 

In business school, I plugged in really quickly with organizations like Net Impact, which cultivates students and professionals interested in social impact. I was an officer for our campus chapter of Net Impact, and I helped lead a board matching program which paired graduate students with local nonprofits as non-voting board members, who would support their designated nonprofit with projects. I also became president of another organization on campus called Challenge for Charity, and spent a year rallying my classmates around two different nonprofits in the Bay Area, driving volunteerism and fundraising. 

I had two informal mentors: Kelly McElhaney, who led Haas’s Responsible Business program, and Nora Silver who was in charge of the nonprofit resource center and served as the on-campus sponsor for the Net Impact Board Fellows Program. Nora helped me get a fellowship with Points of Light Foundation as a graduate fellow, where I worked on their ReImagining Service initiative, a program to help for-profit entities think more creatively about volunteerism as a core competency for their employees. I spent time going through a bunch of data from a survey they administered a couple years prior called the Civic 50 where they engaged and highlighted fifty companies that were especially civic-minded. I had to pull trends and practices, which would be used in a series of case studies for other companies to learn from. 

All of these individuals and organizations were very helpful when I was seeking jobs post-graduation, and based on my experiences while at Haas, I leaned into opportunities at nonprofits. 

Given your background, what qualities do you feel make you uniquely suited to do what you do? 

I do find that there is something unique and meaningful in having worked in the for-profit sector and then moving into the nonprofit space. I am a person who believes in taking some of the practices and procedures and mindsets that are used and applied to corporate spaces, and applying them to the nonprofit sector. 

It’s interesting, because I’ve been reaching out to friends and speaking with my husband to figure out what they think I’m good at. They all say “You’re always doing something creative and you’re always in charge.” The creative thing is interesting to me. Being in charge makes sense for how I’ve seen myself, but I don’t think I’ve made space for myself to really lean into my creativity. 

I also realize I love puzzles. I think it’s because I have a unique ability to organize things and put the pieces together. In strategic planning, for example, I can see how the different components fit together. Other people may get distracted or get stuck in their silos, and only care about their side of things — thinking about programming and not operations, or the budget and not programming. So I think that may be a superpower. 

I’ve also come to notice that I feel a lot of things, and I pick up on people's energy. I used to internalize it but I’m trying not to do that as much. I’m a pretty intuitive person, though. When it comes to solving problems that I care about at my core, I think that being able to connect the dots and layer in a real sense of empathy positions me to hopefully make meaningful and sustainable change. 

When thinking about your future, what are you excited for? 

My friend brought me to an event and they had a healing room where this Reiki master led me through a brief personal session. In that session, I said I wanted to manifest more rest and more peace. I want to relax the anxiety that is linked to all of the pressure I put on myself to do well in every part of my life, all the time. I want to release the guilt that comes with not being able to be a superhuman all the time. I think I just want to be more selective about the kinds of projects I’m taking on in 2020. I want to focus more on leadership, youth development, and travel. These are the things that I care about and that I’m excited to more intentionally bring into my life.

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Raychl Speigner, Philanthropy Consultant & Entrepreneur

Hi, Raychl! Thank  you for doing this. So what do you do and how would you describe it to a layperson? 

I’m a philanthropy consultant with my own business, Speigner Grant Solutions. In short, I help and educate nonprofits on how to raise money. Recently I started another business, Philanthropy Impact Strategies, focused on sports philanthropy where I work primarily with athletes’ foundations. 

You don’t see many black women in philanthropy. How did you get into this space?

Well, first I worked in the athletic development department in college. While there, I was exposed to the role major donors played in collegiate sports. Also, my major in undergrad was sports and leisure humanities, and so I interned with the community relations office working with sports teams, which I really enjoyed. Then once I graduated college, I worked at another college and got into higher education philanthropy, writing grants, etcetera. 

 What made this work appealing to you? 

I loved the community relations team I interned with in college and they loved me. (laughs) I had actually gone to school to be a sports agent but then I fell in love with community affairs work. I realized the impact nonprofits had, and I wanted to be a part of that. 

And how would you describe the impact you’re seeking to have? 

I want more organizations and nonprofits to be impactful in their work. Tracking metrics, evaluating their data, making sure they remain in service of their mission and maximizing their work. I want to ensure they’re well positioned to serve the community. I consider this both a personal and professional impact I’m seeking to make -- they definitely tie into one another. 

There’s a thread I’m hearing, which is that you’re very driven by doing good. Why is it important for you to focus on mission-oriented work? 

It goes back to my first internship. Seeing the impact players had on kids and the community. How the faces of kids would light up when their favorite athlete surprised the class with bookbags, or visited to read a book to them. It completely changed the attitudes of the kids for that moment, and it’s something they will remember forever. And so I got to see the potential impact directly and that is really where I started thinking, I could do this. 

How do you feel you’re well-suited to do what you do? 

I’ve worked in both nonprofit and sports industries, which gives me a very unique skill set that not many have. I know what it takes to fundraise and make an impactful statement, and I use that to help players build out their programming within their nonprofits or foundations. I educate them on fundraising.

Is there anyone you consider an inspiration?

My family in general. I come from a family of strong women. And as a whole, my family really pushed the importance of education. I think also as an entrepreneur, it’s great because my mom understands and supports me finding other ways to make money besides a traditional “9 to 5”. My job isn’t a standard set up, and I feel really lucky that I have a family that gets that and can see the value in me doing something in a different way. So, yeah, they’re my biggest inspiration. 

You’ve just touched on another aspect of what you do, which is entrepreneurship. What was it like to start your own business? 

It was easy at first because I was planning it while still working at my old “9 to 5”, so by the time I was ready to start my own business, I had already laid a lot of the foundation. I started planning it out as far back as 2015 but wasn’t anticipating that I’d be a full-time consultant until some years later. But in 2017, I started to feel that my previous job wasn’t a good fit anymore, and I left. I wasn’t ready to start a job search because that’s a whole process in itself, and since I’d been planning my business on the side for at least a couple of years by that point, it just made sense for me to jump into it full-time. 

Once I had started my business, marketing myself was the hardest part. In my first year, most of my clients were referrals. Once I needed to build my clientele, I got out there and I was like, “Oh, I don’t know how to do this.” It felt like I was starting my business all over again. It was also a lot about shifting my mindset, and walking into a room or an event and showing people your value. That was one of the biggest challenges I had to overcome. I’m coming up on my two-year anniversary and I still feel like I’m working to determine the best events to attend, how to make new connections. I do wish I had worked to build those skills earlier.  

Speaking of what you might have done differently, what advice would you give someone looking to start their own business?

Try to cut your personal expenses as much as you can. You definitely can’t live life the same way as when you had a “9-5,” I’m going to be honest. (laughs) I was trying to live that same lifestyle and you just can’t. 

You should feel okay to cut back on services if you get to a point where you realize you have a broad set of offerings. Remember that you can always subcontract services out, too, if you don’t have the bandwidth or expertise to provide a particular service a client might want. 

I would definitely suggest getting an accountant. They can help you plan your expenses, anticipate tax issues. In any new business, there are months where you may not have income, so having an accountant help you budget in a way where you can be okay when that happens is so important. 

Also, trust your gut. If you’re on a call with a prospective client and it doesn’t feel right, go with that feeling. It’s probably not a good fit. Just like in an interview, a red flag is a red flag. Every opportunity isn’t going to be for you. 

Those are great tips. Let’s close on a high note. What accomplishment are you most proud of? 

Launching Philanthropy Impact Strategies. I love working for nonprofits, but sports philanthropy is what I went to school for. I just launched and I’m excited. It’s something I have talked about since 2011. I keep looking at my website. I can’t believe it’s real! And of course my second proudest accomplishment is my other business, Speigner Grant Solutions. It feels good just knowing that I can do anything if I put my mind to it.

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