On Walking Away, Starting Over, and Having a "Luxury Year"
Denetrias "Dee" Charlemagne is the co-founder of AVEC Drinks. Raised in the Bronx, Dee attended elite preparatory schools and colleges after nearly testing out of the New York public school system as an early teen. She holds an MBA from Columbia Business School and a bachelor's degree from Harvard University.
Before launching AVEC, Dee worked in the advertising and media industry, contributing her skills to creative agencies like Ogilvy and media companies like VICE. Her work involved significant brands in entertainment and hospitality including BOSE, Starbucks, Red Stripe and the Food Network. Dee's creative career also allowed her to live in global cities like London and Hong Kong, where she developed a deep love for hospitality and became the go-to person for planning group trips, bringing people together over shared interests in culture, food, and drinks.
AVEC, co-founded with a classmate from business school, was born out of the desire to innovate the mixer category. Despite launching during the challenging times of the COVID-19 pandemic, AVEC quickly gained recognition, being featured in Fast Company, The Food Network, The New York Times and more. You can find AVEC at grocery stores across America.
Dee was one of the first 100 Black women to ever raise more than $1m in venture capital. She has been featured in Adweek, Forbes, Business Insider, The New York Times and more, and was named Inc Magazine’s Top 100 Female Entrepreneurs of 2022.
Today, Denetrias is the Director of Cultural Strategy at Walmart where she currently focuses on on “putting culture into Walmart and Walmart into culture” via brand and merchant partnerships and campaigns with a focus on younger and/or diverse consumers.
Dee and I first connected when we were both relatively new, wide-eyed, "overnight-success" beverage founders. It was the pandemic, so the way founders became friends at the time was usually through social media or meeting on a virtual conference panel. Once on each other's radar, one of us would suggest a hang on Zoom or Facetime. Many of my closest founder friends were made this way.
The first time Dee and I hung out on Zoom, we both were at a massive crossroads in our lives. We didn't realize this until we started the call. She was planning to step away from her brand and was in the process of breaking up with her long-term partner, and I was mid-divorce and pretty sure our lead investor was about to pull out later that day (spoiler: they did). Needless to say, it was a heavy call, but it set the stage for a special friendship.
Many more Zooms and calls happened after that, as we both navigated immense change in each of our lives, respectively. We met in person for the very first time to do this interview.
This is a good one. Enjoy.
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Hi Dee. I'm excited to talk about the transitions that you've had over the last year.
I’d like to start with your childhood—where you're from and how you grew up.
I grew up in the Bronx. It was predominantly an immigrant community. My mom is Jamaican British, and my dad is from St. Lucia. They met in the Bronx. I lived there until I was around 12 or 13 years old. My elementary school had a strong immigrant focus, almost like attending school in the Caribbean. Discipline was strict, very “Tiger Mom”-esque, though I'm not sure what the Jamaican equivalent would be. The emphasis was very much on education, and I did well. After that, I attended the Young Women's Leadership School in Harlem, which in ‘96 was founded by Ann Tisch with with the backing of female icons, like Oprah Winfrey. It was a unique experience for me, focusing on single-sex education in a public school setting.
By the ninth grade, I was testing out of high school on all the New York State exams. My vice principal suggested looking at boarding or private schools, something my parents weren't familiar with. He was an alum of Exeter, a prestigious boarding school in New Hampshire.
“By the ninth grade, I was testing out of high school on all the New York State exams. My vice principal suggested looking at boarding or private schools, something my parents weren't familiar with.”
I remember thinking how different it would be to attend a school where the students didn't look like me or share my background. So I did everything I could to avoid getting into Exeter. Crying during my interview, you name it. But I excelled in my essay and the SSAT pretest—I guess my competitive nature kicked in.
Despite my efforts, I ended up on the waitlist, while also being rejected from New York City private schools. I was prepared to continue my education in Harlem for 10th grade. But just two weeks before the school year began, I was taken off the waitlist and told I would be moving to New Hampshire. It was a whirlwind, almost like moving to college, but at the age of 13. It was a significant change.
I didn't go to boarding school, but I know people who did. To be leaving your family at such a young age and, in your case, to be leaving with no notice. That must have been a hard transition.
I don't need therapy to tell me it was a huge transition. I was the kind of kid who, up until fourth grade, would cry daily for my parents. I grew up very close to them. I vividly remember the day before I left for Exeter, it was my uncle's wedding. I was in a pink princess dress, surrounded by family, sobbing, just grappling with the reality of going to boarding school.
It was definitely a culture shock in some ways. You see, in the Bronx, I never really thought about the stereotypes people have about the Bronx. To me, it was just home. My parents owned their house, and we had a middle-class lifestyle. In the Bronx, I was even considered the “rich girl,” right? But then I went to boarding school, and suddenly, I was exposed to a new level of wealth. I mean, we're talking about private planes, families who have been going to Exeter for generations, and this insane level of access to networks and opportunities. It was like having to learn a new language and adapt to a new society, trying to catch up on cultural references from years back. It was a very, very intense crash course in a completely different way of life.
“Then I went to boarding school, and suddenly, I was exposed to a new level of wealth. I mean, we're talking about private planes, families who have been going to Exeter for generations, and this insane level of access to networks and opportunities.”
And at the same time, all the kids from New York, they had all done this prep program called Prep for Prep. So, they all knew each other already. And here I was, this new girl from where they were from, but I was on partial financial aid, not full financial aid. I didn't go through the program. There was this feeling of not being rich or poor enough, not black enough, not white enough. It was always this feeling of being in the middle. A lot of my interest in culture and the mixing of different people comes from that initial experience. It was like there were two completely different societies, each with its own way of life and values, but still sharing some common ground. I had to learn to act like a translator, sort of bridging these worlds.
Did you lean in once you were there, or did you want to reject it all?
Yeah. So, in the first months at Exeter, the classes are conducted around a 12-person table, called “The Harkness Method,” which is honestly an incredible way to learn. But in these classes, you're deducing everything. The teachers aren't just feeding you information to memorize. Like in math, it's not just formulas; in literature, you're discussing books with your classmates.
We're all between 13 to 18 years old, so our filters aren't fully developed yet. The teachers are navigating these conversations, and I thought to myself, if I just stay quiet, maybe they'll send me home because I'm not participating.
I managed to keep quiet for about three weeks. Then a friend, who's now a really good friend of mine, pointed out she heard me talking on the phone with my parents and “knew I had a personality.” That's when I realized I couldn’t hide, and I started to find my way.
My ID photo from when I started at Exeter shows me in a Rocawear jumpsuit, with braids, acrylic nails, and then you look at my senior year photo, and I'm in a polo shirt. For some reason, I decided to wear pink every day. That was going to be my identity—the girl who always wears pink. It was a peculiar coping mechanism. I think it was inspired by this girl in middle school who loved pink, and I thought, maybe that's what I'll do—I'll just be the girl who loves pink. Looking back, it's kind of wild.
“My ID photo from when I started at Exeter shows me in a Rocawear jumpsuit, with braids, acrylic nails, and then you look at my senior year photo, and I'm in a polo shirt.”
Wow. Did you feel more settled in your identity before you went to Exeter?
I didn't really think much about my identity back then. Up until Exeter, I was just “the smart one,” you know? And I strongly identified with my family. But it wasn't like, “I am Black. I am female.” It was more about being woman-led, which still resonates with me. It wasn't until I worked in an all-female agency in my mid-twenties that I began to understand that the “Black” part of me had different experiences. At Exeter, for the first time, I had to really break down all the different parts of myself—socioeconomic, race, gender, values, and even understand the different geographies of America.
Looking at my high school group, we were so diverse, beyond America. There was someone from Indonesia, my roommate from Saudi Arabia, Candy from Taiwan who moved to Maryland, Allison from the Greenwich-Stamford area, someone from wealthy Philadelphia, and then me. We all had very different ways of growing up. Imagine one person smoking cigarettes in Bali and then there's me, who was pretty sheltered, all in the same room. It was such an interesting mix of backgrounds and life experiences.
Did you end up feeling a sense of belonging and community?
Once I found my friend group at Exeter, things started to click for me. My dad always emphasized the importance of networking. He'd say, "Network your face off." It's funny, I don't know how he knew so early on, but he always stressed that it's all about your network. He encouraged me not to be afraid. My mom, on the other hand, had a different perspective. A Black woman, growing up in the South Bronx, she was more wary of race relations and gender dynamics and often cautioned me to stay alert. This mindset was part of my upbringing.
So, part of my experience at Exeter was also about educating my parents about this new society I was part of. I think they felt more like outsiders, even more so than I did. I was living in this bubble of boarding school life, somewhat shielded from the outside world. The thing about boarding school is that you don't really see the extent of the wealth until maybe the end. It hits you during graduation week when you start visiting each other's homes. That's when you realize, "Wow, this is how they live." Then it all starts to make sense. But there was definitely a wide spectrum of backgrounds and experiences among us.
So tell me about the path that eventually led you to starting your own thing.
When I graduated from Exeter, I got into Harvard and thought, "Okay, I'm going to be a doctor. Just checking the boxes." But I was a terrible pre-med student, really bad at geometry and physics. So, I quickly realized that wasn't for me. Then at college, I got involved with this fashion show slash entertainment experience called Eleganza. It was a blend of fashion, bands, music, and more. I've always loved fashion and design, and music too. My dad and uncles ran a hip-hop music studio, and my uncle is a producer who worked on tracks like Jay-Z's Blueprint two and songs for Cameron. I was always around this sense of culture and cool growing up, so I think that’s what made me gravitate towards this in college.
“My dad and uncles ran a hip-hop music studio, and my uncle is a producer who worked on tracks like Jay-Z's Blueprint two and songs for Cameron. I was always around this sense of culture and cool growing up.”
Simultaneously, there was my mom, who worked at a bank and was all about ambition. So, I had these two contrasting influences. I've always been outgoing, inheriting my dad's extroverted nature, while my mom is more introverted. My dad's pretty laid-back, and my mom's more of a perfectionist. So, I got both extremes from them. I think this all contributed to my choice to major in psychology, specifically studying when babies start developing biases like sexism and racism. It was fascinating to me, this idea of when people start recognizing differences. All of this would end up serving my career path.
Post-college, I knew I didn't want to go into banking or consulting. I had written a letter to myself at seven, saying that after college, I'd travel. That's when I discovered WPP's advertising fellowship—three years in three different countries, working in different advertising disciplines. I got trained at David Ogilvy's chateau in France, where Madame Ogilvy would greet us in her Chanel suit. I worked in New York, Hong Kong, London, and then at VICE during its transition from a street magazine to Vice News.
I loved the pace and newness of it all. It felt like advertising really mattered. But after Trump got elected, I felt I couldn't just keep doing reels for Bravo and Real Housewives on Snapchat. That's when I got recruited to Joan, a pre-launch, female-founded agency named after bad-ass women like Joan of Arc. We tried to start the female version of VICE , addressing the issue that even though women were running the editorial side of media, men controlled the business side. That's when I started to really think about business.
So, when I was at the agency, this was around the time of the Women's March. Suddenly, everyone was like, “Oh man, we need female creativity.” We were about to launch Joan, and it seemed like perfect timing. But then, everything changed when the Facebook algorithm shifted, and media just tanked. That's when I thought, “Okay, it's time to really look into business school.”
At Joan, I was working on this story about how there were only like 20 black women who had raised over $1 million in VC funding, which was nuts to me. That really hit me. I wasn't sure if I wanted to be a funder or a founder, but it pushed me towards business school to figure that out.
So I ended up going to Columbia. In school, I got into angel investing and VC, realizing it's just BS with numbers. But I liked the building aspect of it. So I was leaning toward the founder path.
Then I met Alex, my co-founder, who had this idea for AVEC, a beverage brand. I've always been the organizer in my friend groups, planning parties, trips, you name it. So, this idea about drinking occasions was really interesting to me. It wasn't about nerding out over the drink itself, but more about what happens culturally when people get together and drink.
But, you know, I was freaking out about the business school debt. Then COVID hit, and they canceled school for a year. I was thinking, “How am I going to manage this? Do I freelance?” But then, things started to align. There was some loan forgiveness, and we decided to start fundraising for our business idea. Things just began to fall into place in a way I didn't expect.
So you left your career in media and advertising, and jumped into co-founding this beverage brand, AVEC. That’s a pretty big change. Did you have any idea what you were getting into?
Having been at smaller agencies and media companies, I had seen firsthand what it takes to build a brand, and also the challenges that come with it. So when we started our brand, we didn't go to a fancy branding agency. I managed the process, and we worked with a freelance designer and everything happened quite naturally and opportunistically. For instance, I had a friend who was doing PR for restaurants in New York, but that business had dried up in the pandemic. So, I asked her if she wanted to help launch our brand.
The biggest surprise for us was the value of earned media and how organically our brand could grow within a year. What I didn't anticipate, though, was the anxiety that came with it. I'm usually pretty confident in my work and the products we create, but I found myself ending each day questioning my decisions and whether I had made the right choices. It's mentally taxing. Entrepreneurship in its early phases can really overtake your mental and physical space. It's hard to be present.
Building the brand itself didn't bring any major surprises. It was more about solving puzzles, which I enjoy. Figuring out things like how we were going to meet certain goals, how the product was going to taste—it was all new and exciting.
That's really cool. Your earlier career prepared you perfectly for the role.
Yeah, it's kind of funny. Before I went to business school, I sort of looked at marketing and thought, “Haha, that's not really serious business.” But then, when you're in business school, you suddenly see the value in storytelling. You realize that a lot of people don't actually know how to do media, how to effectively communicate. It's a real skill, a serious business skill.
Going to business school was a game changer for me. It gave me this boost of confidence in areas I wasn't familiar with before. I came to this realization like, “Oh, I actually do know how to do this stuff.” It's like I had this newfound respect and understanding of the intricacies of marketing and how crucial it is in the business world.
Yeah. And to me, observing as an outsider, the brand grew fast, right?
It didn't feel fast. And I'm always like, is it anything? But then people tell me all the time how they know and see the brand, so I guess it is something.
Well, that's interesting because, you know, I had the same experience. It's hard to comprehend the impact that your brand has, even when you see it in the press, when you’re heads down in the grind. Especially during the pandemic, I think it was really hard to feel the real impact of what we were building because we were just stuck in our warehouse, shipping out tons of product but never actually seeing anyone drink it. We never got to enjoy that part of it.
Yeah. We couldn’t go out and see how our brand was living in the real world.
Yeah. Well I do want to talk about what happened later. You eventually made the decision to step away from the brand. That’s a big, heavy decision for a founder, and you were the face of the brand. Can you walk me through that?
Yeah, I think it was more of a slow burn rather than a sudden decision. I can pinpoint the moment I decided to leave, but there wasn’t a specific moment when I started considering it. It's really challenging to start a partnership with two people who have strong visions. There's no right or wrong, just different views on where the brand could go. For a long time, trying to combine these visions wasn’t doing justice to the brand. Part of branding is clarity, and it was becoming confusing.
The fundraising landscape had also changed dramatically. The benchmarks for success in beverage companies had shifted from $10 million to $100 million, changing the goalposts significantly. On a personal level, people don’t often talk about the personal financial runway needed to sustain yourself, especially in a place like New York City, and I took a pay cut to be a founder. My life was on hold—I couldn’t think about buying a house, getting married, or settling down. Financial lack had become the center of my life, affecting my friendships because I couldn’t afford certain things, which weighed heavily on me.
“My life was on hold—I couldn’t think about buying a house, getting married, or settling down. Financial lack had become the center of my life, affecting my friendships because I couldn’t afford certain things, which weighed heavily on me.”
Being a black woman in this environment presented its own challenges. I never intended to be the face of the brand or to be in all these press interviews, but that's where the media wanted to take it. Yes, I had this goal of seeing if I could raise a million dollars, which I achieved, but that wasn’t my life's purpose. I was always more interested in the cultural impact of the brand, and what I was doing day-to-day was drifting away from that.
I went to business school to grow beyond the CMO title, but I found myself being pigeonholed into that role. It’s hard for me to say no to things, but I knew that wasn’t what I wanted. I didn’t want to settle for something that didn’t fulfill me. There was a day when everything came to a head—the partnership, a personal breakup happening at the same time, me having to find a new place to live—it was just a lot. It felt like the right time for a life cleanse, not just picking off issues one by one, but addressing everything together.
Ironically, my grandma, who’s religious, always talked about 33 being a big year—the “Jesus year.” I was never very religious and didn’t take it seriously at first. But after talking with women in my family, I noticed a pattern. Whether it was having a child or some other major life event, 33 seemed to be a year where something significant shifts for many people.
Oh, wow. I do want to zoom in on this shift. I mean, I remember catching up with you last year and you were in the process of leaving your company and breaking up with your live-in partner, right? Your entire life changed at once. And I can't help but think now about how you went through a shift of this magnitude when you were 13.
Yeah.
Your entire life changed, essentially overnight. And here you are, going through it again.
I didn't even think about that until this moment.
I can only imagine that this was triggering and led to some painful self-exploration. Can you talk about that experience?
For me, this was like facing failure in a way I had never before. It’s like, I’ve always been this person who just said yes to everything, always moving forward, driven by a kind of fear—fear of what happens if I don’t get into a relationship, start a business, or what if it all doesn't work out? And my mind always rushes to the worst possible scenario first.
That whole experience was like living out every fear I had. It was terrifying, and there was this odd sense of “What more can happen now?” The two things I had feared the most were happening simultaneously, and I just let it all unfold, let it melt.
After moving out in September, I didn’t have a permanent home till February. I relied on friends, and I’ve never been the one to easily ask for help, so that was a huge learning curve. The universe kind of just granted me help without me having to ask explicitly. Therapy started around that time too, and it was different because now I was right in the middle of everything I feared. I made that year about introspection, about asking questions, and really contemplating the value of time. There was this constant question in my head: Did I waste time in that relationship, in that business?
“There was this constant question in my head: Did I waste time in that relationship, in that business?”
I was freelancing, but hadn’t fully left the business until January. There were about four months where I was in this limbo, thinking I might reverse my decision. But then, I just let opportunities come to me. I talked to people I admired to figure out what to do next. I knew I couldn’t settle for a job that didn’t excite me. That’s how I ended up freelancing for Walmart, among other projects. Initially, I was like, “There’s no way I’m going to work for Walmart,” but then I surprisingly loved it. I had written down what I wanted from a job and shared it with my network, looking for something that allowed me to create, that connected people and culture, and was, frankly, sexy—I just can’t do unsexy stuff.
At Walmart, all these elements came together in a way I hadn’t anticipated. My boss was someone I had worked with before and knew my personal situation, which was rare. It was comforting to be able to be vulnerable both personally and professionally. It wasn’t just about the job title or the role, it was about the trust in the person. It gave me a sense of stability that I didn’t know I needed so much.
Every time someone said, “You’re doing so well, you’re so strong,” I would just break down because I didn’t feel strong. I was allowing myself to be in this state of messiness. I always saw myself as this free-spirited, wild child, the kind who didn’t follow norms, but I realized I needed stability. That realization was a huge shift for me, balancing my adventurous spirit with this newfound need for stability in my life.
Wow. I think this is going to be really helpful to some readers, because I've had a lot of conversations lately—and not just with entrepreneurs—a lot of people who have decided to walk away from something that just wasn't right anymore. They didn't have anything to replace it with, but they knew they needed to leave anyway. That is a really bold move, right? When I’m talking to folks going through this, I can see the panic, I’ve seen the tears in their eyes. It's very scary, and yet we do it.
Yeah. I cried and cry a lot so I feel them.
Can you share more about the process, tactically, of what you did to get yourself out of the really scary, great unknown place, and making moves toward whatever your future was, without actually knowing what you were working towards?
Yeah, yeah. So on September 1st, it hit me—I didn't have a home. I thought, “Okay, first things first, where am I going to live?” It’s such a basic thing, but it became my immediate priority. I needed to figure out the essentials: where to live, what to eat, what my next steps were. I planned for a month's worth of living, but also had to be really honest with myself about what was working and what wasn't.
“On September 1st, it hit me—I didn't have a home. I thought, “‘Okay, first things first, where am I going to live?’”
I tried staying with my mom, but after three days I realized it just didn’t work. I love her to bits, but being there, I could see her taking on my emotional baggage and it was just amplifying everything. I knew I couldn't stay in that environment. I had this friend whose parents were going on vacation, and I thought to myself, “Maybe I need some alone time.” That was a big deal for me. I’m usually the one with a packed social calendar, always around people. But then I realized I had to sit with myself, no matter how painful or boring it might be. My therapist was like, “You need to just sit and be with yourself for a bit.”
So, that's what I did. I found a place to sit, and every couple of weeks, I’d reassess everything. It was a time of real self-reflection, stepping back from my usually busy life to just be with my own thoughts and feelings. It was about confronting what was going on inside, which was something I hadn’t really done before.
The second big thing for me was navigating the exit from both personal and professional relationships. I found myself wrestling with a lot of guilt, feeling like I was responsible for everything that went wrong. I have this tendency to blame myself, thinking that all of this was my doing. To manage that, I started writing down just the facts of what happened, keeping a daily log of my feelings and the events of the day. I focused on noting down the pure facts to understand what really happened, how I felt, and what my part in it all was.
“I found myself wrestling with a lot of guilt, feeling like I was responsible for everything that went wrong. I have this tendency to blame myself, thinking that all of this was my doing. To manage that, I started writing down just the facts of what happened.”
At the same time, I was conscious of not playing the victim, not falling into the trap of thinking everything was happening to me or that everyone was against me. I wanted to acknowledge my role in these situations, to learn from this healing process. I talked to others who had been through similar experiences, like you and other founders, as well as my parents and my aunt. These conversations were part of my healing.
One significant aspect was spending more time with my father. My parents separated while I was at Exeter, and since then, I hadn't really confronted how their divorce had impacted me. I hadn't dealt with those hard conversations. In my family, we're very celebratory, typical Caribbean style, you know—we deal with the bad stuff quickly and then have a good time. But I allowed myself to not always have a good time, to be alone, and to delve into these harder topics. I stopped putting pressure on myself to always be the fun, positive, bubbly Dee, the life of the party. Instead, I let myself melt into those more challenging, less celebratory aspects of life.
Once I had a handle on the basics I started to refocus on work. At that time, I was still involved with AVEC, but I knew I needed to figure out my next steps. I had a history of freelancing before business school and post-Joan, so I decided to tap back into that network. I reached out to people I had worked with before, letting them know I was open for freelance work. Soon, I landed three different consulting projects which helped keep me busy and also gave me the space to figure out what I really liked and wanted from my career.
Someone advised me to write down a clear paragraph—no more than 6 sentences—outlining what I was looking for in a job, almost like manifesting it. I found this exercise incredibly helpful during my job search. It was important to give myself time to “melt,” to be with myself and process everything. But then, eventually, I needed to focus on what I truly wanted in a job. The idea was to manifest my ideal job by clearly stating the three main things I wanted, along with a broader description and a couple of “wish list” items.
“Someone advised me to write down a clear paragraph—no more than 6 sentences—outlining what I was looking for in a job, almost like manifesting it. I found this exercise incredibly helpful during my job search.”
So, I wrote this paragraph down, detailing my ideal job, and started forwarding it to people in my network, connecting and networking with people. This approach helped me clarify my goals and actively seek opportunities that aligned with what I was looking for in my professional life.
The generosity and support I received from people during this time were astounding. I found myself being more vulnerable in professional settings than I usually would be. For instance, I reached out to John, the CEO of Kings Hawaiian Bread Rolls. I had met him at a conference, and despite him being much older, in his late 60s, I felt comfortable enough to call him and openly ask, while I was in my final days at Avec, “Should I leave my company? You're a smart businessman, tell me what you think.”
I was expecting him to dive into business specifics like margins or equity. Instead, he simply asked, “Are you happy?” That question hit me hard, and I just started sobbing on the phone. That conversation made me think about more than just work. It made me question other aspects of my life—where I was living, what changes I needed to make. It reframed my situation as an opportunity to start over. So, it became about rebuilding from scratch, embracing this chance to reset and rethink my path, both personally and professionally.
Eventually, I realized I needed to be patient with the job search. There were moments I got really scared about money, but I held onto faith that something would come through. It was a lesson in trusting the process and believing that the right opportunity would present itself at the right time.
One of my friend's husbands made a comment when I was feeling particularly anxious. He said, “You shouldn't worry too much. Even if your current path doesn't work out, you can still join the rest of us in middle management. That world still exists, and it's always an option.” That perspective was a bit of a wake-up call. It made me realize that even if things didn't pan out exactly as I hoped, there were still viable options available. I could take a “bridge job,” something to get me from one point to the next. It was reassuring to know that even in the worst-case scenario, I would still survive and find my way. This was about accepting that sometimes, it's okay to take a step back or to choose a path that might not be the dream but is still a solid and viable option.
Eventually I had opportunities in front of me and needed to choose what I wanted to do. That marked another turning point for me. I went back to focusing on the basics, like where I was going to live and what I needed to learn from this job. I asked myself, “What skills do I want to gain from this role? How do I want my personal life to shape up? Will it be fulfilling?” It was about reassessing everything again, determining what was important to me. I ultimately ended up joining Walmart in a full-time leadership role, after enjoying my time working with them as a freelancer.
One thing that really helped during this time was starting to read again. It's one thing to sit with yourself in silence, but reading opened up new perspectives and ideas. It was through reading that I stumbled upon the concept of time, especially from the book "4000 Weeks." Time kept coming up as a theme in what I was reading and thinking about, and I began to accept that time is something beyond our control. It's going to unfold regardless of what we do, and there's a sort of peace in relinquishing that control, in accepting that we can't dictate every aspect of how our lives unfold. It was a process of learning to be okay with the flow of time and the unpredictability of life.
“Time is something beyond our control. It's going to unfold regardless of what we do, and there's a sort of peace in relinquishing that control, in accepting that we can't dictate every aspect of how our lives unfold. It was a process of learning to be okay with the flow of time and the unpredictability of life.”
So, with all these thoughts and realizations, I decided to just let things unfold naturally and embrace what I dubbed my “year of luxury,” my year of stability. For the next year, I made a conscious decision to not take on any side projects. I wasn't going to get overly involved in planning trips for my friends or overcommit myself. I planned to have at least one weekend every six weeks where I did absolutely nothing, just to break the routine and give myself some breathing space.
It was a significant shift for me because I've always been the kind of person who's juggling multiple things. You know, being Jamaican, we joke about always having four jobs. But I decided, for this year, just one job. I wanted to reduce the number of decisions I had to make daily. It was about simplifying my life and focusing on stability and self-care.
As I'm approaching the end of that year, I can see how this approach has impacted me. It's been different, stepping back from the constant hustle and allowing myself the luxury of stability and fewer decisions. It’s a change, but one that I needed and have learned a lot from.
Do you feel like the earlier, culturally cool, exciting chapters in your career in some ways helped you appreciate this chapter of having a more stable lifestyle?
Yeah, definitely. Going through all this, I've learned to appreciate things in a different way. Being in a stable company like Walmart, I feel empowered in a unique sense. It's almost like having a kind of fearlessness. It's not that anyone at Walmart is threatening to fire me, but it’s more about the mindset. If the thought of losing my job comes up, I'm like, “Okay, sure, I'll be fine.” It changes how you operate and move within a company. Having gone through various adventures in my life, fear isn't the same kind of motivator it might be for someone who hasn't experienced those ups and downs.
“Fear isn't the same kind of motivator it might be for someone who hasn't experienced those ups and downs.”
And you know, there's still excitement in my job. I don’t find it boring at all—in fact, I think it's super cool. I always wanted to find newness, and the challenge was how to find that newness within the stability of a job like this. I feel like I've found a good balance at Walmart. I don't have that fear of missing out, that FOMO, about starting a company or taking a huge risk. I've learned that sometimes those risks don't work out, and sometimes they do, but for now, I'm content with where I am, finding newness and excitement within the stability and structure of my current role.
Did you have any worry about going into a place like Walmart, which is massive, and has an established corporate culture? Like, were you worried about having to suppress or edit yourself, like you had to do in boarding school?
I've always had this mindset that I can figure things out. When it came to adapting to corporate culture, I wasn't panicked. Of course, there are moments when I'm just blatantly myself, and I wonder, “Is this too much for corporate? Is this inappropriate?” I'm very upfront about what I know and what I don't know. But, you know, I think one of my strong suits is being able to see how all these different pieces, like merchandising, marketing, and supply chain, come together. I've been in those realms before, albeit not on such a grand scale as at Walmart.
So, I never really had that thought of, “Oh no, it's corporate, this is going to be the end of me.” Instead, it's been more like, “Wow, look at all these benefits! How am I going to navigate all this?” It's almost like there are too many resources at my disposal, which is an interesting challenge in itself. I find it's about adapting to this new environment, figuring it out as I go. There's a certain strength in being able to jump into a new environment and just get to work figuring things out. So, no, there was never that moment of dread about entering the corporate world. It was more about embracing it and finding out how to make the most of it.
After all of the introspection you’ve done this year, do you find that you derive different things out of work now than you did before?
My relationship with work has definitely changed. It's not as personal anymore, not in the same way it was when it was my own business. I don't feel like my entire worth is tied up in my work now. As an entrepreneur, your self-worth is often closely linked to your company's success. And as a Harvard grad, there are these societal expectations, like you're supposed to be running a major company or making some groundbreaking innovation. I've been working on shedding these “shoulds,” like “I should be doing this because I went to Harvard” or “I should be achieving that because of my parents' sacrifices.” Now, it's more about choice: “I could do this, but I'm choosing to do that.”
I've found myself being more present in both my work and personal life, keeping them separate instead of trying to merge them. I used to attend networking events that were also about my business or mix personal and professional discussions at work. Now, I'm trying to draw clearer lines between work, personal time, and journaling. It's about compartmentalizing these aspects of my life to be more focused and present in each area.
I was just telling someone at breakfast this morning that one of the things that I will never do again is base my entire identity on what I am building. Because that's what I used to do—it’s what most founders do. And when I went through my own process of self-exploration in the last couple of years, I realized that I had entirely tied my worth to my work. There was no separation.
Yeah. Even in friendships, I used to think that I had to be the one organizing parties, planning dinners, and essentially being super fun for people to enjoy my company and love me. But when I reached a point where I couldn't offer any of that—where I couldn't be the life of the party or the organizer—I was forced to see what friendships would stick around without all that effort. And surprisingly, I found out that it's not necessary to always be in that role. When I couldn't do it, I discovered that people didn't need me to.
This realization came not just from a mental space but from a physical and emotional inability to keep up that role. I was, in a way, cut off from doing it. I couldn't show up in the same way I used to, and that was okay. It was an important lesson in understanding the value of friendships that don’t require constant entertainment or effort, and it was liberating to see that genuine connections remained even when I stepped back from my usual role as the planner and entertainer.
Do you feel like you got to the bottom of those wounds during that time?
I got to the core of them. I don't know if I'm at the bottom. That's still a process.
I committed to therapy for an entire year, like clockwork—once a week, every week, for an hour. It was a very deliberate choice, almost ironic in a way. As a founder, therapy felt like a luxury I couldn't afford, but with good health insurance, it was suddenly just $25 a session. This accessibility allowed me to really immerse myself in the process.
But eventually, I hit this point where I realized I couldn't lean on therapy or another person forever. I had to start doing some of this work on my own. So, I took what I learned in therapy—like the importance of journaling—and made sure I dedicated an hour to just be with myself, not running around, not being busy. I started to focus on how I could understand and improve myself without someone else guiding me every step of the way. It was about learning to dig deep and find those answers within myself, to prompt my own growth and healing without relying on my therapist to do it for me. It was a huge shift in perspective and approach, but one that I felt was necessary for my journey.
“I started to focus on how I could understand and improve myself without someone else guiding me every step of the way.”
Yeah. Man, What an amazing process that you've been through. I can tell you're like a different person than when we first connected.
It's a strange feeling, looking at yourself and realizing there are parts of the old you that are gone. There are aspects of my former self that I look back on fondly and think, “Oh, I wish I could still be like that.” But I guess it's all part of evolving, of growing and changing.
I never really thought about how drastic these changes were until now. It's like starting over from scratch. When I moved into my current place, the only things I brought with me were my coffee machine, because it's my absolute favorite item, and my mattress. It was a very symbolic fresh start, having just those two items with me. It underscores the enormity of the changes I've gone through and the new phase of life I'm embarking on. It's both daunting and exciting to realize you're at a point of such significant personal evolution.
Do you feel like now that all of your fears came true in life and you survived… have they been replaced with new fears, or do you find that you are actually more fearless overall?
I am more fearless overall, but I have more fears. I guess I'll never completely shake off fear; that perfect state of nirvana seems elusive. But, you know, I've been thinking a lot about time recently. It's like a constant question in my mind: Am I using my time wisely? Is this the right moment for things? In my mid-thirties, I see everyone around me doing different stuff, and it makes me think about things like whether I’ll ever find a partner, or if I’ll ever reach what I consider to be my full potential. These aren't fears about basic needs, like whether I’ll have a house—they’re more high-level, almost philosophical worries. It's not about that raw survival fear anymore, but rather the privilege of being in a place where I can ponder over my values, the possibility of finding someone, and those bigger life questions. It feels like I've moved from a phase of just trying to survive to now grappling with deeper, more existential concerns.
People often say to me, “You went to all these great schools, do you really think you could end up on the streets?” And my answer is always, “Yes.” I find that there's a humbling aspect to fear. It keeps you grounded. I never want to claim that I'm completely fearless because I believe fear serves as a sort of check on our ego. It's important to have that sense of vulnerability. Without fear, there's a risk of becoming overly confident, thinking you're invincible and that nothing bad can ever happen. That mindset can be quite dangerous. Fear, in a way, keeps us cautious and aware of our limitations, which I think is crucial for staying grounded and making prudent decisions.
I agree. Just this morning, on the way to you, I accidentally spilled a matcha all over myself in the subway station. A classic New York mistake. Then I came up and the hot dog stand guy gave me some napkins. I was very grateful. Then I saw there was a CVS right there on the other corner. I went to go get some baby wipes to wipe all of the matcha off of me. But I was not being as cautious as I would like, because I was covered in matcha and distracted, and then I almost got hit by a car, and then I almost got hit by a bike. This was kind of one of these funny moments of remembering that vigilance can be good. I don't think too much fear is helpful, but it's always good to have some. Especially on the streets of New York.
Yeah.
Just to be on your toes a little bit. Always looking.
Exactly.
Yeah. Well, we’re approaching the end of our time here. Any last advice that you would have for folks who are reading, who are considering some major life changes themselves? Who are thinking of going out into the great unknown?
The key lesson I've learned is that life is inherently chaotic. It's not just a few people going through change—it's like constant, unending waves. The ocean metaphor really resonates with me—life is an ocean, and we’re all navigating our own boats through these waves. The crucial part is understanding that stabilizing your own boat is your responsibility, regardless of the chaos around you.
“Life is an ocean, and we’re all navigating our own boats through these waves. The crucial part is understanding that stabilizing your own boat is your responsibility, regardless of the chaos around you.”
Interestingly, now I find myself missing a bit of that chaos, almost seeking it out, but I know it will inevitably reappear. Early on, I remember labeling myself as “chaotic” and feeling guilty about it, like I was a creator of chaos. A friend pointed out how I needed to change that language I used for myself, to stop calling myself chaotic and start believing in my ability to stabilize. This shift in perspective was enlightening.
One piece of advice I'd share, which we didn't touch on much, is to be mindful of how you talk to yourself. One exercise from therapy was to write down every negative thing I said to myself. It was eye-opening to see how often I was negative without even realizing it. The task was to jot down any thoughts about myself, positive or negative. It helped me see that the language I used about myself was not only reflective of my current state but also influential in shaping where I ended up. If you focus on chaos, you feel chaotic. Where your focus goes, your energy flows. If I think I'm chaotic, then chaos becomes my reality.
Right. If you're looking for more stability, it has to start with yourself.
Yeah.
My last question is… how can we support you or follow along on your journey?
Add me on LinkedIn—it’s the best way to follow me. For support, still go follow and buy @avecdrinks and personally, I’m taking on some side hustles as this year of luxury comes to a close so let me know if you have ideas.
Great. Thank you so much Dee.
Thank you.
