Family, Leadership, and Philanthropy: Sydni Joseph’s Inspiring Journey

• Sydni Joseph brings a strong entrepreneurial spirit shaped by her family into her leadership at Big Plan Holdings, a diverse family office.
• She and her team lead a range of ventures, from music publishing to large-scale hospitality and real estate projects including a notable partnership with Jon Bon Jovi.
• Sydni values strong relationships and clear communication, while spearheading the philanthropic efforts of The Joseph Family Foundation with her immediate family.
• Grounded by personal passions and family roots, she continuously seeks new growth opportunities.

1. Could you tell us a bit about your childhood and how it may have shaped you into the person you are today?

I grew up in the Chicagoland area in a very close-knit family. My parents, middle school sweethearts who’ve been together since eighth grade, set a strong example of love and loyalty. They had my sister, Sophie, and I in their mid-twenties, during a time when money was tight. Right before I was born, my dad rollerbladed to work in Chicago with just $20 a week and reusing sandwich bags to save money.

Despite the challenges, our parents raised us with strong values–kindness, respect, and the importance of education. We were encouraged to try everything. Sophie did horseback riding and cheerleading, while I was into ice skating, dancing, and Poms. I joined the National Honor Society and student council while Sophie led Best Buddies, a large nonprofit supporting people with special needs. 

We were raised to be well-rounded, and that foundation still shapes us. Our bond with each other and our parents remains just as strong. These days, we all work together in our family office, something none of us expected but have fully embraced. 

2. You started your professional journey at a young age. What inspired you to dive into entrepreneurship so early on?

Entrepreneurship has always been part of my world, thanks to my dad. He built his own company from the ground up, working long hours and taking big risks. Watching him inspired me early on. I admired his independence and drive, and it made me want to build something of my own. 

In 2019, while I was still in college, my mom introduced me to two women—one from the music industry and another from the cannabis space—who wanted to start a women’s subscription box company. They pitched the idea of delivering curated lifestyle and wellness products, including CBD items, through an e-commerce platform. My mom asked if I wanted to be a founding partner, and I said yes even though I was managing three majors, a minor, and a part-time job in the university’s events department.

That company became 3rd Eye High. We launched just before COVID-19 hit, which helped with e-commerce demand but made brand-building harder without in-person marketing. Still, the experience was a crash course in business—business development, vendor relations, e-commerce, marketing strategy, inventory management, point-of-sale operations, and customer relations experience—all from my college house in Kentucky.

I had also been following my dad’s entrepreneurial journey closely. He started one of his companies in 2014 and sold it five and a half years later, which eventually led us to launch our family office. When live events paused during the pandemic and 3rd Eye High wrapped after 14 months, my dad asked if I wanted to help co-found the family office. Just like that, I pivoted again. This time, to something we could build together as a family.  It all started earlier than I expected, but those years gave me real-world experience I couldn’t have learned in a classroom.

3. Were there any specific challenges you faced starting so young, and how did you overcome them?

One of the biggest challenges of starting young was navigating the massive life shift our family went through in 2020. My dad co-founded a cannabis company in 2014 alongside his commercial real estate business, and by July 2020, he sold it. He was still relatively young and planned to travel the world with my mom, but then the pandemic hit. Suddenly, he sold off one of his companies, had no routine, and we were all stuck at home.

It turned into an identity crisis for all of us. My family’s always been driven and busy. We’d experienced both financial struggles and successes, but nothing prepared us for the strange mix of isolation and life-changing transition we felt at that moment. 

That’s when we decided to start our family office, which we jokingly call the “Joseph Family COVID Passion Project.” It gave us a renewed sense of purpose. My dad’s instinct has always been to turn challenges into opportunities, and that mindset shaped Big Plan Holdings. We wanted to become a resource, a platform that supports other entrepreneurs chasing their own dreams. The challenge was redefining who we were in a completely new phase of life, and building this together helped us move forward with intention. 

4. Can you tell us how Big Plan Holdings came to life and what your day-to-day role looks like across its different ventures?

Big Plan Holdings started during the pandemic, but the roots go back to my family’s long-standing love for music, sports, hospitality, and entertainment. In 2019, after my parents bought a second home in Nashville, my best friend Spencer–who’s been in music his whole life—suggested we explore music publishing. That idea led to the creation of Edgehill Music Publishing, our first venture. Around the same time, my dad fulfilled a long-time goal of investing in real estate on Nashville’s Broadway Street. The real estate acquisition and the launch of our music publishing company eventually fueled what became Big Plan Holdings.

Today, we’re a full family office with about 10 team members and a growing portfolio that reflects what our family genuinely cares about. We also launched The Joseph Family Foundation, our family foundation from a philanthropic perspective. We’ve built our portfolio companies around what our family genuinely loves. That focus has shaped a strong, value-driven investment approach.

As for my day-to-day responsibilities, I split my time doing business development, supporting our portfolio companies, and handling key family office tasks. I also lead marketing for our hospitality group, which has about 250 employees across three venues, and stay involved in our family foundation and other special projects. No two days look the same, but everything I do ties back to growing what we’ve built.

5. What’s one project under Big Plan Holdings that holds a particularly special place in your heart?

The Broadway real estate project holds a special place in my heart. It was a full-circle moment watching my dad achieve his dream of owning property there. Seeing that vision come to life after years of hard work meant a lot to our whole family.

Professionally, it’s been incredible. What started as an L-shaped parking lot is now a 37,000-square-foot, five-story venue with multiple stages, rooftops, a mechanical bull, phenomenal food and drinks, a tattoo parlor, and a team of 150. Partnering with international icon, Jon Bon Jovi, made it even more surreal especially since he was my mom’s favorite artist growing up, and we went to all his shows as a family.

Most bars on Broadway are country-focused, so we wanted to offer something different. We just celebrated the venue’s one-year anniversary and had our most profitable day yet. After years of hard work, it’s deeply rewarding to see it thrive and to know it was built with heart, history, and family at its core.

6. You’re deeply involved with The Joseph Family Foundation. What causes are closest to your heart, and why? How do you envision the Foundation evolving over the next few years?

The Joseph Family Foundation is a passion project of my family. It’s our way of giving back to those who haven’t had the same opportunities we’ve been fortunate to have. While we have a strong team at our family office, the foundation’s work is handled entirely by the four of us: my parents, my sister, and me. My sister, who serves as president, has led much of its growth.

We started with four focus areas: scholarship, dignity, equity, and welfare, donating across those pillars. But over time, our approach evolved. Now, we host community-focused events like panel discussions in our Nashville office to raise funds and awareness around specific causes. We also support art, books, literature, and other resources that tie directly into the missions we care about. 

Education is especially close to our hearts. My sister teaches special education and has developed a certified human rights curriculum available globally. All proceeds from the curriculum go to the organizations chosen by our foundation. Going forward, we’re focused on scaling that impact using education, storytelling, and community engagement to support meaningful, lasting change. 

7. As a young woman in leadership, what has been one of the biggest lessons you’ve learned so far?

First, surround yourself with incredibly smart people who are genuinely willing to teach you and support your growth. The right people will challenge and elevate you.

Second, build a personal board of directors and not just a big network. A strong network is fantastic, but the people who will actually show up for you and help solve real problems are invaluable. Identify and nurture those relationships.

Finally, communication styles matter. Everyone has their preferences, and learning to adapt, whether it’s email, text, or in-person, makes collaboration stronger and shows respect. It’s a small effort that makes a big difference in getting things done and leading effectively.

8. Who are some of the women who have inspired or mentored you on your journey?

First and foremost, my mom, Tara, and my sister, Sophie. My mom inspires me through her deep love for people. She sees art as a powerful form of expression and brings that perspective into everything she touches, from fashion to interiors in our hospitality work. She is the voice of the creative. She reminds me that their seat at the table matters as much as anyone else’s.

My sister is just as passionate, especially in the philanthropic space. She is a fierce voice for the underrepresented and sets boundaries with clarity and compassion. 

Outside my family, Ashley Picillo has been a major mentor. She’s a sharp, successful entrepreneur in the cannabis space, and someone I trust and turn to often. She’s part of my personal board of directors and has shaped how I lead and grow.

Dr. Kendra Ward, my cardiologist since childhood, is another mentor. She’s part of Lurie Children’s Hospital in Chicago. She walks into a room, commands attention, is smart, dedicated, and loves her people well. Her commitment to truly understanding and helping people has taught me a lot about compassion, precision, and showing up for others.  

And finally, Alyssa Syputa, my babysitter-turned-mentor. Alyssa helped raise me, instilling many of the morals, manners, and life experiences I had growing up. 

I am eternally grateful for all these women in my life in some way, shape, or form, and I firmly believe I would not be who I am without them.

9. What’s next for you, personally or professionally, that you’re most excited about?

I’ve been focusing more on balance and making space for things that ground me outside of work. There was a point when I felt stretched thin, constantly in motion but never truly recharging. That shifted when I realized I couldn’t even slow down enough to call my mom. It was a wake-up call. Now, my family is more intentional about setting boundaries. When we’re on family vacation, it’s family time, not on a work retreat. That change has helped me stay grounded.

I’ve also found energy in simple things like long walks, reading, working out, and even learning to cook, which is something I never took interest in growing up. These are the things that reset me and help me show up better each day.

Most importantly, I’m grounded by the people closest to me–my boyfriend, Jordan, and my sister. They’ve been my constants through everything, and I’m most excited about continuing to build a life that leaves room for growth and connection.

10. How do you stay grounded and motivated as you continue to grow and take on new ventures?

While there’s always something exciting happening professionally, travel is what really keeps me motivated. It’s one thing that fills my heart like nothing else. Ever since I was a kid, my top bucket list goal has been to visit all seven continents. 

I’m especially looking forward to an upcoming trip to Costa Rica with my dad and my sister for Father’s Day. It’s one of my favorite places in the world, and I’m excited to see my dad finally take a break and decompress.

I’m also planning a fall trip to Europe–hopefully Paris, Spain, and maybe Portugal. Culinary, cultural, religious, and just immersive experiences of seeing the world are what recharge me and keep me motivated, even more than the work I love.

Sydni Joseph’s journey reflects resilience, adaptability, and purpose-driven leadership. Shaped by a strong family foundation and an innate entrepreneurial spirit, she carved her path across music, real estate, hospitality, and philanthropy with heart and intention. From building meaningful relationships to championing human rights and education through The Joseph Family Foundation, Sydni blends business insight with a deep commitment to people. Her approach to leadership offers a refreshing reminder that success isn’t just about what you build, but how and why you build it.