If you want to find the future of family entrepreneurship, look not to a single city or industry, but to the many airports, hotel lobbies, and vibrant public squares where Deborah Haile and her son Jonah Seyum have mapped out their mission—one passport stamp at a time. Sophisticated and relentlessly purposeful, Deborah is that rare figure who can lead a global Legal Operations team by day, brainstorm a book plot with her son at night, and still manage to travel across three continents before the season changes.
Deborah’s story, and the family brand she’s built with Jonah, isn’t just a tale of globetrotting and boardrooms. It’s a living, breathing lesson in style, ambition, and what it means to raise the next generation of culturally fluent, globally minded leaders—all while keeping a perfectly packed carry-on and an even more organized calendar.
From Boardroom to Boarding Gate: Deborah’s Story
Born in Eritrea and raised in Minnesota, Deborah Haile now balances life between California and the world, her roots as diverse as her resume. Her background in public affairs and nonprofit strategy gave her the foundation to build a mission-driven business, but motherhood brought clarity and new urgency: “I wanted Jonah to grow up grounded, compassionate, and globally aware,” she says. “Traveling together gave us that opportunity—and writing our books together made those lessons real, not just for us, but for every family who picks them up.”
Deborah’s days are demanding. As a global leader in Legal Operations for an international company, she manages cross-functional teams and high-stakes strategy calls that could intimidate even the most seasoned professionals. And yet, what sets her apart is the way she treats travel and storytelling not as escapes, but as extensions of her leadership philosophy. For Deborah, excellence is portable, discipline is non-negotiable, and style is about intention, not excess.
“I believe in classic, professional pieces—tailored blazers, versatile accessories, a statement watch. These are things that work anywhere, from a San Francisco office to a literary festival in Asmara,” Deborah shares. “But more than that, my sense of style is about showing up—organized, prepared, and ready to represent not just myself, but our brand and our mission.”
The Family Business—Runway, Runway, Everywhere
If family entrepreneurship once conjured images of lemonade stands, Deborah and Jonah have shattered the mold. Together, they co-founded Tiny Global Footprints: a dynamic brand that blends multicultural children’s literature, a hit podcast, annual events, and a fast-growing platform for global learning.
By age 12, Jonah has visited 22 countries, co-authored three books with his mother, written three solo titles, co-authored a book with his two best friends in Eritrea, and helped launch the Young Eritrean Writers Program—mentoring peers in Eritrea and working with them to help them write their own stories, as well as translate Tiny Global Footprints’ books into Tigrinya. (Four titles have already been translated, with more on the way.) Their annual book events in Eritrea have blossomed into community celebrations, connecting young readers with the possibility of seeing themselves on the page.
Their joint bibliography reads like a travelogue for the modern family:
- Finding My Amigo in Cuba – A tale of friendship and discovery.
- The Search for Elephants in Thailand – Jonah’s wide-eyed adventure among his favorite animals.
- Filling My Pockets with Nakfa in Eritrea – A family story about homecoming, tradition, and what it means to belong.
- Basketball or Soccer?, What Does Daddy Do All Day?, and The Torture of Chores – Jonah’s solo projects, each capturing the everyday questions, dreams, and dilemmas of childhood.
- The Eri Basketball Boys – Jonah’s latest, co-authored with friends in Eritrea over two years and two continents, using video calls, summer visits, and boundless imagination to create a story of teamwork and identity.
Each book is a passport, a memoir, and a gentle lesson in empathy. “We want to show kids everywhere that the world is big, beautiful, and theirs to explore,” Deborah explains.
The Art of Grounded Glamour
For all the jet-setting, Deborah remains fiercely practical. “Routine is my anchor,” she confides. “Early morning planning, regular check-ins with Jonah, and making time to connect—even if it’s just a quick call from another time zone—keep me grounded.” Preparation, she says, is her secret weapon. She doesn’t just plan outfits for versatility; she plans every meeting, every trip, every launch.
This focus on preparation extends to her role as Jonah’s coach and mentor. She has helped him develop not just as a writer, but also as a public speaker, podcast host, and entrepreneur in his own right. Their partnership is built on mutual respect, clear communication, and the shared understanding that “family is the first and best team you’ll ever have.”
Her travel philosophy is rooted in substance: “Glamour and elegance, to me, are about being composed and confident in every situation. Whether I’m leading a board meeting or helping Jonah finish a chapter, I want to show him that poise and presence matter. You can be both approachable and polished. And you can make room for joy and wonder—even when you’re working hard.”
Family Brand, Global Ambition
As Tiny Global Footprints has grown, so has its visibility. The duo’s work has been featured in Fortune, Variety, Authority, and ThriveGlobal.com. Their podcast, Global Footprints Stories, has found an audience of families and educators who want more for their children—more adventure, more empathy, more worldliness.
“Travel and storytelling are two sides of the same coin,” Deborah says. “Every trip we take inspires new ideas, and every story we write opens doors for the next adventure.” It’s an approach that resonates with brands, educators, and parents alike, making Tiny Global Footprints not just a family business but a movement.
Raising the Next Generation—with Grace
Deborah’s life is a modern-day masterclass in balancing ambition and grace. She is proof that women can lead global teams, nurture their families, and build businesses rooted in vision and values. Jonah, for his part, is the kind of confident, articulate young man who makes you believe the next generation is ready for anything.
Their travels aren’t just for Instagram. From navigating Tokyo to brainstorming book ideas on planes to Europe, they model resilience, flexibility, and a deep commitment to their mission. “It’s not always perfect,” Deborah laughs. “But it’s always worth it.” If there’s one thing Deborah’s story makes clear, it’s that glamour is more than what you wear—it’s how you live. She’s created a legacy that’s equal parts ambition, adventure, and heart—a true original in a world that too often settles for the ordinary.
