Betting on Herself: Sheikha Al Otaibi’s Journey from Fashion Dreams to Building Across Borders

In this powerful episode, we sit down with Sheikha Al Otaibi — first-gen college grad, co-founder of a fast-growing remote staffing startup, and Babson College’s Entrepreneur of the Year — to talk about what it really takes to build something from the ground up.Born in Boston, raised by her grandmother in South Jersey, and navigating life between her Saudi and American roots, Sheikha opens up about identity, resilience, and the hard decisions that shaped her. From interning at Jimmy Choo to launching a company that helps U.S. businesses hire top talent across Latin America, her story is one of grit, reinvention, and radical self-belief.We talk hustle culture, cold emails, cultural disconnection, money mindset, and the very real mental toll of trying to “make it.” Sheikha doesn’t hold back — and her honesty will resonate with anyone who’s ever felt like the outsider in the room.If you’ve ever felt torn between expectations and your truth, this conversation will meet you right where you are.