In this episode of Hustleshare, we sit down with Clive Aranha, General Manager of Hotel Casiana, to talk about how he went from running bars on cruise ships to leading one of the top hotels in Tagaytay. Clive shares how growing up in the hustle of Mumbai sparked his love for hospitality, how he built and sold his own restaurant in Australia, and what brought him back to the Philippines. He also talks about the ups and downs of entrepreneurship, building strong teams, and how he helped turn things around at Hotel Casiana in just over a year—with the help of partners to fix key challenges and support their rapid growth.

In this episode of Hustleshare, we chat with Stephanie Sy, founder and CEO of Thinking Machines, to unpack her journey from Stanford and Silicon Valley to building one of the Philippines’ leading AI and data science companies. Stephanie shares how her early startup attempts and time at Google shaped her hustle, why she made the leap back home to start from scratch, and what it took to grow Thinking Machines in a market that was still new to data science. She also gets real about the challenges of building an AI team in a resource-constrained environment, the scrappy moves that helped them thrive, and how purpose-driven projects are helping shape the future of tech in Southeast Asia.

In this episode of Hustleshare, we sit down with Jake Go, Founder and CEO of Springboard Philippines, to trace his path from coasting through a dead-end dev job to running one of the country’s most resilient niche staffing firms. He shares how lessons from his grandma’s tiny Recto canteen stuck with him, the career-shaping mentorship he got at Kalibrr, and the leap into entrepreneurship that saw him earn back his first investment in six months—completely bootstrapped. Jake talks about winning boardroom deals as a baby-faced 23-year-old, how teaming up with his wife brought a much-needed dose of frugality, and why balancing “push” and “pull” has kept Springboard profitable for over a decade. He also opens up about teaching at La Salle, mentoring students, and the leadership shifts that turned him from a people-pleasing founder into a decisive, purpose-driven leader.

In this episode of Hustleshare, we sit down with Bimbo Adewoyin, founder and CTO of Doublesquare Networks Inc., to talk about how he went from installing DIY wireless setups in college to leading a nationwide tech company. Bimbo shares how growing up in Nigeria shaped his work ethic, how he adjusted to life in Bicol, and how he hustled his way into city-wide projects—all while figuring things out on his own. He also talks about building a team, learning the ropes of government procurement, and how PLDT Enterprise helped them grow through the toughest moments of the pandemic.

In this episode of Hustleshare, we chat with Alex de Leon, Group VP of Marketing at PropertyGuru, to unpack the wild journey that took him from tinkering with computers in Manila to working at Google in Silicon Valley—and eventually marketing for one of Southeast Asia's biggest proptech companies. Alex shares how growing up between cultures shaped his hustle, what working three jobs in college taught him about grit, and why it took 26 tries before he finally landed at Google. He also gets real about what it’s like starting from customer support, how being a generalist became his edge in tech, and why building from scratch in the Philippines was the most career-defining move he made.