Mady Dewey’s Multi-Passion Journey: From Tech Startup to SI Swimsuit Model

In a world that often tells women to pick one path and stick to it, Mady Dewey has proven that ambition doesn’t have to fit neatly inside a box. She’s a tech entrepreneur, a podcast host, a model, and a passionate advocate for women in media — all at once. Her story represents the kind of multidimensional career that modern women are beginning to embrace unapologetically. And for Mady Dewey, that journey from building a startup to gracing the pages of Sports Illustrated Swimsuit isn’t a contradiction — it’s a celebration of her authenticity, creativity, and drive to rewrite what success looks like.

Mady Dewey first made her mark not on a runway, but in the tech industry. After studying communications and technology, she quickly found her footing in Silicon Valley’s fast-paced startup culture. She worked at major tech companies and saw firsthand both the possibilities and the pitfalls of social media. While she was fascinated by the power of digital communities, she also recognized how social platforms often encouraged comparison and perfectionism. That insight became the spark for something greater — a platform designed to change the way people connect online.

Together with her co-founder, Mady launched Herd, a social app built with mental health and authenticity at its core. Unlike traditional social platforms that prioritize likes, followers, and filters, Herd aimed to create a positive environment where users could share ideas, creativity, and experiences without judgment. It was an ambitious goal — to reimagine social networking in a way that celebrates individuality over validation — and it reflected Mady’s own evolving perspective on what it means to live confidently in the digital age. Her vision wasn’t just about building an app; it was about shifting the culture of online interaction entirely.

Even as she was establishing herself as a thoughtful voice in the tech world, Mady Dewey began exploring another side of her creativity. She had always loved storytelling and visual expression, and when the opportunity to compete in the Sports Illustrated Swimsuit model search presented itself, she decided to take a leap — not to escape tech, but to expand her definition of self. That decision changed her life. In 2022, she was named the Sports Illustrated Swimsuit Swim Search winner, earning a feature in the iconic issue and immediately gaining attention as one of the magazine’s most refreshing new faces.

But for Mady, modeling wasn’t just about photoshoots or fame. It became another form of empowerment. Standing confidently in front of the camera, she wasn’t representing an impossible standard of beauty; she was representing a new kind of woman — one who can be smart, ambitious, and glamorous without compromising any part of her identity. Her participation in Sports Illustrated was deeply symbolic of her mission: to break stereotypes about what women in tech, media, or leadership should look like. She’s often spoken about how being both an engineer of ideas and a public-facing creator allows her to explore different parts of her personality. She doesn’t choose between intellect and artistry; she thrives in the intersection of both.

Her authenticity has struck a chord with a generation of young women navigating similar expectations. Mady Dewey has become a voice of reassurance in a culture that often pressures people to specialize too early or fit into narrow career molds. Through her podcast and online presence, she encourages others to explore multiple passions — not as distractions, but as complementary forces that build a fuller, more resilient sense of self. She often says that life isn’t meant to be lived in one lane, and her career stands as proof.

As her modeling career grew, Mady continued to champion the principles that defined her tech journey. She uses her platform to promote conversations about mental wellness, body confidence, and digital authenticity. In interviews, she’s been refreshingly honest about the tension between technology and self-worth — how easy it is to get caught up in algorithms and aesthetics instead of focusing on personal growth. Her voice is calm but compelling, balancing vulnerability with strength. That balance has made her stand out not just as a public figure, but as a thought leader for a more mindful era of media.

Mady Dewey’s duality — being both a founder and a fashion figure — highlights a broader shift happening across industries. The modern entrepreneur doesn’t need to hide behind a screen, and the modern model doesn’t need to be defined solely by her looks. By existing comfortably in both spaces, Mady represents a new archetype of womanhood: intellectually engaged, emotionally aware, and unapologetically ambitious. It’s not about defying expectations anymore; it’s about dissolving them altogether.

Her story also resonates because it’s grounded in relatability. Before she was a magazine cover girl or startup founder, she was a college student trying to figure out what she wanted to do — just like anyone else. She admits that much of her success has come from saying yes to opportunities that scared her. When she applied for Sports Illustrated’s Swim Search, she didn’t have a modeling background. She just wanted to tell her story and connect with people who valued authenticity over perfection. That vulnerability is what makes her success so inspiring. It wasn’t about being the most experienced or traditionally “fit” for the role; it was about having the courage to show up as herself.

What’s particularly fascinating about Mady’s journey is how seamlessly she’s blended technology and media into a unified purpose. Her career reflects an understanding that modern influence is not limited to one medium. Whether she’s designing an app interface or stepping onto a red carpet, her work is connected by a consistent message: that confidence, creativity, and community are at the heart of true empowerment. She’s part of a generation redefining what personal branding looks like — less about curation, more about alignment with one’s values.

Her time with Sports Illustrated Swimsuit has also positioned her as a leader in the body positivity movement. The brand itself has evolved over the years to celebrate diversity and realness, and Mady’s inclusion helped strengthen that message. She represents the everyday woman who works hard, takes risks, and isn’t afraid to evolve. Her confidence radiates not from perfection, but from purpose — from knowing who she is and what she stands for.

Off-camera, Mady continues to build on her tech foundation. She remains passionate about supporting female founders and mentoring other women entering male-dominated industries. She’s spoken at conferences, partnered with organizations focused on entrepreneurship, and continues to highlight stories of women who are building companies with compassion and courage. That through line — using technology and media to uplift others — is what makes her influence so genuine.

In many ways, Mady Dewey embodies the spirit of the digital age — multifaceted, creative, and guided by authenticity rather than convention. Her journey from tech startup founder to Sports Illustrated model isn’t about career hopping; it’s about integration. It’s about recognizing that innovation and self-expression can coexist, and that the modern woman doesn’t have to choose between ambition and artistry. She’s living proof that identity is expansive, not restrictive.

What makes her story so compelling is that it’s still being written. With every new project, whether in front of the camera or behind a laptop screen, Mady Dewey continues to inspire a generation to chase their passions boldly and to redefine what success looks like on their own terms. Her multi-passion journey isn’t just a personal triumph — it’s a cultural statement. It reminds us that strength comes from authenticity, creativity thrives on curiosity, and that sometimes the most powerful way to lead is to live fully, fearlessly, and without apology.