As told to Bryna Jean-Marie

Oxford defines a wave as a sudden occurrence of, or increase in, a phenomenon. Some definitions even include the word disruption. Enter Kahina Van Dyke. She is unequivocally a quiet storm that has caused culture shifting waves in her revolutionary fintech career. And she has taken a meticulous and impactful journey through the unfolding of a lifelong dream—to own property in Oak Bluffs—that is reframing how African Americans experience Martha’s Vineyard.

When she used to come to this magical New England Island for three-day jaunts with her father, Leon Van Dyke, she was just a little girl. And the Atlantic Ocean was simply a backdrop to her carefree toddler existence. Now when she sits on the porch of one of her families’ three 150-year-old Bed and Breakfast properties, and gazes into the vastness of the infinite water, her hopes span as far and wide as the deep blue sea. She is looking at the depth of legacy that she has created in this beloved islet. A shore that once placed a grain of sand in her heart, that has now produced a priceless gem.

Kahina passionately shares the arduous passage to fulfilling her sacred dream. A story that has poetically come full circle into a golden spherical blend of reality and fantasy. Her beloved Oak Bluffs is now the ultimate happy place for her children, her children’s children, and for many generations to come.

UPTOWN: How have your memories on the vineyard led to building a legacy here?

Kahina Van Dyke: Some of my earliest memories are of the Black community of kids, parents, and grandparents enjoying themselves. Owning property on Martha’s Vineyard was my unspoken dream. I remember when my dad used to bring me for a few days because, honestly, that’s all we could afford. He was a civil rights activist and an educator. And a bunch of the activists used to come to hang out and relax together. They worked hard and put their lives on the line, and this was their place to meet up and chill. So, I grew up watching my dad and his friends enjoying themselves at the beach and on porches with food and laughter. When I became a teenager, I had this awareness that this was unlike any other place because I had started to travel to other places. And nowhere compared to this island. This was the only place that I felt free. I saw my neighbors as well as strangers all in this kind of state of easy freedom and relaxed joy. This was when I made a commitment to own a home here. I didn’t personally know anyone who owned property. And I didn’t come from one of those families who have been multigenerational homeowners. But I made a commitment to myself that I would buy a home in the Copeland district, walking distance to the beach, so that my children could experience this Black joy. They could feel this sense of freedom that they would grow up with as normal. And it wouldn’t be this rare treasure that happens occasionally for a few days. Instead, it would be their normal. And so that was my unspoken promise. Because it sounds kind of crazy when people ask, “What are your life goals?” and you say “Oh, to own a Victorian home with no heat on an island that I go to for two weeks every year.” That’s not most people’s sense of an American dream. But it was mine.

UPTOWN: That’s a huge dream to hold. Why did you keep it so private?

KV: I didn’t come from this life, so it seemed crazy to dream that I belonged here. Also, I lived a very corporate life, and I kept my work and personal life very separate. I didn’t tell anybody about my Oak Bluffs life. I was working in Silicon Valley. In fact, I didn’t tell anybody at work that I had bought a hotel. I was one of the only female executives at my level. I was very visible, and I just felt like people would want to understand why. And I guess it didn’t feel that safe to share this very personal part of me. To talk about my commitment to culture and my safe space and creating spaces of freedom and joy. I couldn’t tell the story without saying that part of it because it would not make any sense to many people. But I always knew I’d get an immeasurable return on my investment because it wasn’t a financial return I was looking for. There was no way to talk about it without really revealing a lot about things that are sacred to me. And I think as a Black executive in corporate America, especially when you’re at the top of your game, and you have a lot of visibility, you don’t want anything to come up that could be weaponized against you. I was on a break between two companies when I decided to buy the first hotel in 2018. I called my now ex and told him that I was going to buy the Narragansett House. He thought I was out of my mind because I was working 90 hours as a global executive in Silicon Valley. I told him that it would be easy, and we would just hire people and make it work. At that moment, I didn’t know how I was going to do it, and I definitely didn’t realize how hard it was going to be. But I did it anyway.

Narragansett House

UPTOWN: You were laser focused. Where were you living at the time?

KV: I bought my first house on Martha’s Vineyard in 2011 before I was married and before I had children and was living in Europe at the time. The last 20 years I have lived all over the world, and it’s been great to learn multiple cultures and languages. I have lived in New York City, London, Prague, Madrid, Dubai, Germany, and Singapore. I’ve worked on the ground in dozens and dozens of countries, but I’ve only lived in seven. My children were born abroad, and they are dual passport holders. My job put me on assignment everywhere, and I was saving money for my dream for decades. I didn’t buy anything overseas. I would rent because I was clear that I wanted to own a house on the vineyard. Over the course of many years, I started looking at houses every time I came to the island for vacation. I put in seven offers that did not get accepted. I had a budget and I stuck to that and frankly didn’t understand how the real estate market worked here. Eventually, I walked into the house that is now my family’s summer home. I call it my spiritual home because I knew immediately that this was the house I was going to buy. It was over my budget and when I applied for a mortgage they said, “You want a mortgage for a house that was built in 1870 and has no heat? We don’t take houses that don’t have heat in New England.” And I think if I hadn’t worked at the bank, I would not have been able to convince them. I ended up getting the mortgage. I finally got my house—before marriage, and before kids—it really was the fulfillment of a lifelong promise to myself that I made as a young woman with a big dream.

UPTOWN: Did you ever second guess your plan?

KV: People always questioned my journey. They asked, “What are you doing? You don’t even live in the states.” And I would say, “Let me tell you something. I may travel and live all over the world, but you’ll know where to find me every single summer for the rest of my life. I’ll be sitting right on my porch having a sundowner—likely a gin and tonic.” So, for me this is a lifetime investment. That’s the way you must think about home ownership on the Vineyard. You’re making an investment, not a financial investment, but you’re making a lifestyle investment in a place that feeds your soul because these homes tend to be older. They’re Victorian seaside cottages. They are at least 100 years old, and they need constant care and attention. It’s not about the non-existent central a/c, it’s about the community that you’re a part of. It’s about the way that it makes you feel. It grabs you. So that was my first home purchase, and I was very happy to sit there on my porch every summer and not do anything really. I just went to the ocean, rode my bike, and restored myself to go back out into that world.

UPTOWN: What inspired you to purchase more property and to become a hotelier?

KV: I had owned my first home for about seven years. And I was on a break between two jobs. I took two weeks off, I was spending some time on the vineyard alone, and I walked by what would become the Narragansett House. I saw that scenario, which is nearly five years ago now. It had been for sale, at that point, for a couple of years. And gentrification was happening in the community which made me very nervous, especially after Lola’s was sold. I had been eating fried chicken at Lola’s with my daddy since I was three years old. The fact that her restaurant disappeared after I saw President Obama’s nomination speech there was heartbreaking. I had so many memories in that space. Everybody was so shocked that it was gone, but nobody thought to buy it. So I decided to buy the Narragansett House because it was a way to preserve another important property. But also, a place for writers and artists-in-residence. And literally, as I bought it, I was contacting writers to see if they would do chats in my garden.

UPTOWN: Why is holding space on the vineyard for artists so important to you?

KV: Our writers and artists are being priced out of the Vineyard. So it’s important that we create space for them. Our writers, painters and artists are the people who capture our culture and create pieces that last for generations. And if they’re not part of our community, then our culture suffers, and our legacy will not be told. So, it was my intention to create a place that brings together the community by having events in the garden for everyone to stop by and visit. It is a home to our important connections and conversations. This idea of inclusive hospitality is to be able to tell our story and who we are in a much more complete way. My mom, Linda Van Dyke, was a writer. She wrote for the love of the craft and to tell the story. There was no financial gain. I’m a creative person too. I grew up with an appreciation for art. What it means in all forms and the sacrifices that artists make to tell stories. So one of the first things I did was to reach out to the woman who runs the writers institute here on the vineyard to do an artist in residence program for writers and artists. They could stay with us and do their work. This is how we continue to build our legacy. We are living this wonderful life because James Baldwin, Phyllis Wheatley, Frederick Douglass, Dorothy West and so many more wrote our history. And now we are artists and caretakers of our culture. Our painters give us images before we even can articulate the words. Photographers grab moments of real life that even today touch us in a profound way. In my store, Jubilee on Circuit Avenue, I have vintage photos from the 1800s of us because we’ve always been here. And we’ve got to align ourselves with our history and our shared cultural inheritance. This is our town. We co-created this sacred space from the very foundation. Before it was a town. It’s the reason that on the African American heritage trail of the 35 sites 20 of them are in Oak Bluffs. We need our children to know that our people walked these streets 150 years before they did. We are part of an elegant and dignified community. And it is imperative that our artists continue to document our history.

UPTOWN: And you’re continuing to preserve our history with Dunmere by the Sea?

KV: Yes. I discovered that this house was in the Green Book [a guide published from 1936–1967 listing places that extended its business to African Americans]. And it was near my family’s home. I was invited to put in an offer even though they already had multiple offers on the table. For me that was more about the preservation of a legacy, and I wanted to make sure that home that was in the 1964 Green Book was honored in the right way. Luckily, I was successful, and I got it in 2020. Now it’s on the African-American heritage trail which is well deserved. It is the story of the McBride brothers who are from Harlem, New York. They bought this house in the 1960s and created a haven for beach access for African-American families who wanted to vacation without the aggravation of racism. And that’s what led me to owning this beautiful property. I’m an intentional investor. I trust the step in front of me even when I’m not quite sure where it’s all taking me.

Dunmere by the Sea

UPTOWN: What’s your philosophy on having such a profound ability to manifest?

KV: I always say I have a very strong connection to the past, the present, and the future. Because the actions of the past determine our present and our present determines the future, which is why for me, they all intersect in the here and now. For example, this conversation that we’re having, and the conversations that happen on the porch, conversations and connections that happen on the beach, on Circuit Avenue, or over a meal… Those connections that are happening right now are helping to shape what this place will continue to be. So we just need to continue to engage with intentionality. We can be in the middle of the best party in the world and manifest greatness. Listen, I know how to turn up, and if you’re doing it with intentionality and joy, it’s an expression of freedom. Freedom is how you move in the world. And so I think that we have an incredible opportunity to continue to move in very intentional ways and build off this legacy to ensure that it’s here but also to expand our own idea of what the Vineyard is and what it can be for all of us.

UPTOWN: How did you juggle family, work and your dream?

KV: When I first started the hotel, season one, it was crazy. Every Thursday night I would fly the red eye from California to Boston. Land in the morning and take the bus down to the Ferry so that I could greet my guests for the weekend on Friday. Then, I would leave on a Sunday evening flight back to California so I could be at work on Monday. I had to be at the inn for my first season because I’ve never been a hotelier before. I needed to greet my guests and understand everything they wanted and expected. That’s an important part of the entrepreneurial journey. You need to put in the preparation, the work ethic, and the time it’s going to take to master a new craft. I had 25 years in financial technology at that point, which enabled me to make that purchase. The bank gave me that purchase based on what I had proven in my day job. Not what I provided from my entrepreneurial venture. So putting in that fintech work was very important to the fulfillment of my dream. The following year, my second year as a hotelier COVID hit. I was terrified. If I did not have a day job, I would have lost the hotel. Instead, in the middle of the pandemic, I trusted my gut and I decided to buy another property and bought the Dunmere by the Sea. I am very grateful that I was so practical. You know, I always say you need a Plan B and then you need a Plan Z because Plan Z is for things like COVID which shut everything down and changes the world. You need to know, despite it all, you can still support your family and your dreams.

UPTOWN: And what led to the purchase of the Inkwell Beach House?

KV: This was an obvious choice that I made in 2021 because it is an iconic ocean front property that overlooks what I consider to be our public town square and our community gathering place—the Inkwell Beach. It is also right next to Dunmere by the Sea, literally on the property line. So when that came up for sale it felt like a once in a generation opportunity. I remember looking at that house and the other houses as a small child on the seashore. And at the time, most of them were not owned by African Americans. Historically we owned the houses throughout the Copeland historic district but not many in our community owned property on the oceanfront or Ocean Park. And I remember thinking to myself, “I have to try it.” I may not get it but I have to try. Because if I’m successful then the next little 4-year-old girl can look up and see the American flag and the Juneteenth flag. Or her mom, or dad, may say to her, “That’s owned by a Black woman.” And maybe that will inspire her, 30 years later to buy her own property and continue building this legacy.

UPTOWN: You were part of the launch of the revolutionary fintech movement. Tell us about that epic journey.

KV: My first job in financial services was being one of the first employees on Citibank’s new Internet team. I was in fintech before the word “fintech” existed. Then it was called Internet digital banking. I may look like this visionary genius. But the reality is I just was curious about how this new thing called the Internet was going to potentially expand and change access to financial services for people.

It was an emerging field that led me to move abroad and overseas where the technology and digital payments were moving faster. Mobile and other technology was much more advanced outside of the U.S. While we were posting checks, Europe was processing electronic real time payments. Twenty-five years ago, I was conducting the first tap and go pilot in London. I was able to go abroad and get a set of experiences that allowed me to accelerate my learning curve far beyond my colleagues who are in the U.S. In 2022, I had just returned back home after being an executive overseas for almost 20 years. And it hasn’t been announced yet but I’m transitioning to be an operating partner for one of the largest private equity firms in the world to do investments in financial technology which is a different aspect of the industry for me. This area also has very, very few women and almost no African Americans in this area of finance. So I’m very excited about being part of their team and helping to bring a new perspective to this area of finance and investing.

UPTOWN: Your career and your personal dreams are melding. That must feel amazing.

KV: Yes. I’m now at the point where I can help companies, CEOs and founders expand their dreams. And the fact that I’ve had this entrepreneurial experience over the last five years helps me to be more empathetic to how that journey feels as an entrepreneur. It feels amazing to know that your passion project is bringing financial services to underserved communities in Africa, or it is driving community and culture. In order to secure capital and to be able to expand and scale, you need people who believe in you. So this new opportunity is going to be really interesting and impactful as a platform to enable the dreams of others. Now I get the chance to fully integrate my two worlds. Everybody at the firm knows about my hospitality business. Now I can be one person. I can be a holistic person. I can be an investor; an entrepreneur; a board member; and a hotelier. I can make muffins, talk about contemporary Black art, and I can discuss global trends in financial technology. It’s so beautiful for me to be able to be at a point in my life where I can be uniquely me as an individual without feeling like I have to hide parts of myself. That’s real freedom for me. To be myself.

UPTOWN: Congratulations on the opening of Jubilee on Circuit Avenue. Was having a store in Oak Bluffs a part of your Vineyard vision?

KV: No, it wasn’t, but sometimes people are angels who can see things clearly when you can’t. This opportunity was presented to me earlier this year at an incredibly challenging personal time. So my initial response was no, and to give it to somebody else. Two months later the woman came back to me, and said I know you said no, but I really believe that this is something that’s perfect for you, and it’s supposed to be yours. I have two other people who want this store, but I think it’s supposed to be you. So could you please think about it again. Thank God for people who have that sense of discernment. I prayed and meditated on it. It wasn’t an easy decision. But I said yes not knowing how I was going to find the time or the energy to do it. I wanted to be a platform to support the dreams of entrepreneurship of other folks. I realized that this is a unique opportunity to have a store in the middle of Circuit Avenue to be a platform for so many great designers, creators and entrepreneurs who don’t have other places to connect with a conscious community of consumers. This allows me the unique opportunity to be of service to entrepreneurs in a different way. Jubilee, a word that has a lot of meaning for us, has a celebratory nature, and a connotation towards freedom. And in my own personal journey, I think this store is my statement of this next chapter of life that I’m in, and that we’re in as a family. I am fully expressing myself to be of service and to support my own ventures as well as those of others. We can do well when we invest in both individual and collective well-being.

UPTOWN: Do you think that the island is losing its small-town charm? 

KV: During certain months. And it’s a minority of people. Film studios and corporates are paying for the housing and that’s why renting has just gotten astronomical. People are not paying for it themselves. You’re not seeing average families renting houses. You’re seeing entertainment industry executives, directors, producers, audio engineers, etc. using corporate money to secure their housing. It’s fantastic that everybody’s here to see and support Black film and Black filmmakers. But on the other hand, it does shift the character of the island for a specific number of weeks in August. In the north, we don’t go back to school until after Labor Day. Down South they’re in school by the third week of August. So the early August meet-up made a lot of sense because no matter where your friends were from you could connect with each other during that week. So we have manufactured this August meet-up in the vineyard. And people are now realizing things are priced out. Even July is packed and has become a very busy time. Part of the solution is that we have to be intentional about gathering here all summer long—from Memorial Day to Juneteenth to 4th of July to Labor Day, summer is three months long, folks.

UPTOWN: Why did you decide to start a Juneteenth event in the Vineyard?

KV: About three years ago I said, “I’m doing Juneteenth in the Vineyard.” And the reaction from some of my people was, “There are no Black people in the vineyard in June.” And I said, well we are going to start celebrating it because it’s time and our freedom is worthy of celebration. So we started small on the porch with a culturally focused program with music, food and history with like-minded people, others will come. And that’s exactly what has happened. The Amistad sailed into town this summer. Grammy-nominated musicians performed. We had a fireside chat with Nikole Hannah Jones, and services by Dr. Eric Michael Dyson. We also had a water ceremony, led by Dr. Jessica B. Harris, where we honored our ancestors. And 30 of us celebrated the fine culinary traditions, and really the foundations of American fine cuisine, at a Juneteenth Eve dinner prepared by Chef Martin Draleck. These are just an example of new memories that we can create. This opens up people’s minds about when they can come to the Vineyard, and they don’t always have to come in August. So, we can also determine our own destiny. And we can create something so much more meaningful that is going to really feed our souls in a completely different way. We must reframe our narrative about this magical place. The Vineyard is all summer long and that’s one of the reasons why I felt so strong about having a Juneteenth event. During this celebration we can honor Black culture, Black history and Black trailblazers in a place that has literally been shaping all this dynamic culture for 150 years. So, we’re just continuing our legacy. We’re not starting something new.

UPTOWN: Do you think that having events like Juneteenth will reshape the culture again?

KV: Absolutely. And I see things taking place organically that are setting the tone for that to happen. Two weeks ago, I was on my porch greeting guests. Suddenly, I hear a girl scream in recognition of a new friend. Two young ladies saw each other and discovered they were both going into the same Freshman class at Spelman College. They found each other because they were in a group chat and one of them said, “I’m staying right across from the inkwell,” and the other one said, “Oh my God I am too.” They were both here on a mother-daughter getaway trip before college. A few days later a third girl shows up who is also an incoming freshman. And one of the young ladies ended up reading at a ceremony on the beach “The Meaning of July 4th for the Negro,” a speech by Frederick Douglass which is a 20-year tradition held on the 4th of July by the descendants of Frederick Douglass. She was a part of this sacred community gathering. So, no, she didn’t have a white party, but she had something that she will carry in her heart for the rest of her life. Because she got invited to read, she feels very much a part of the Inkwell community. Labor Day used to be popular because there were events around the Jazz Festival. I think it’s important for us to bring new events and not compete with the 150 events during the same 12 days in August. We can be more strategic and have events that we and our children enjoy. This also helps to bring the original MV culture and feeling back to the island. Your holiday on the vineyard should not be stressful. That is only a specific time. The rest of the season is the island that we all know and love. My goal is to make this a haven from Memorial Day to Columbus Day. And anytime you come for your children they will find culture. They will find community. They will find history. They will find relaxation and restoration. They—and you— will find that freedom inside that is hard to describe but so easy to feel when you are here.