In this episode, we sit down with Jiwon Hong, founder of YesPlz, an AI-powered fashion discovery platform that’s rethinking how we shop online by understanding real human preferences, not just pushing trends.

Jiwon’s journey spans continents and industries: from her teenage years navigating culture shock in South Carolina, to working at global giants like Samsung and Sony Music, to launching not one but two startups. Her first company failed not because she didn’t work hard, but because she built in isolation. Her second? She did it differently. She talked to users. She studied their habits. She listened, obsessively. And from that came YesPlz — a smarter, more intuitive shopping experience designed for how people actually want to shop.

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.

Kalsoom Lakhani, a woman who defies every box—and then builds new ones.

Kalsoom is the co-founder and general partner of i2i Ventures, Pakistan’s first female-founded venture capital fund. She’s spent over a decade building the startup ecosystem in Pakistan and other overlooked markets as the founder of Invest2Innovate, launching the country’s first startup accelerator and supporting more than a thousand entrepreneurs across South Asia. She’s also a published writer, global speaker, and host of “The Comparable,” a podcast spotlighting voices from emerging markets.

Born in Dubai to Bangladeshi and Pakistani parents, raised across continents, and never fully at home in any one place, Kalsoom embodies what it means to be a true third-culture kid. Her journey has taken her from international schools in Dhaka and Islamabad, to the University of Virginia, to the corridors of Washington, DC, and into the highest-stakes rooms of venture capital, where she invests in the builders and change-makers the world usually overlooks.

In this episode, we dive deep into what it takes to lead as a woman of color in a male-dominated industry, the grit required to keep going through rejection and uncertainty, and the life-changing impact of building with empathy and curiosity. Kalsoom opens up about starting her first blog while working in defense contracting, fighting imposter syndrome, redefining power, and why betting on the “unusual suspects” can change the world.

If you’re ready for a masterclass in resilience, cultural identity, and self-trust, Kalsoom’s story will hit you right where you need it.