How Oswald Yeo Quit School, Slept in an Office, and Powered Millions of Careers Across Southeast Asia

In a modest three-story shophouse nestled in the heart of Jakarta, the early seeds of Glints began to sprout. This setting was far from glamorous; it was defined by grit and unyielding commitment. Oswald Yeo and his co-founders lived and worked in that cramped space where four single beds were squeezed into one room. There were no curtains to shield them from the morning light—just the bare essentials and the shared ambition that kept them going. Colleagues passing through often found themselves drawn into the nightly "pillow talks," where the team reflected on the day's" challenges, shared insights, and exchanged hard-learned lessons.

When the space became too crowded for everyone to have a desk, they got creative—making do with staircases and even a washing machine as makeshift workstations. Life and work blended seamlessly in this environment; each morning, the team would rise from their beds, mere steps away from where they would spend the day building their vision. The lines between personal time and hustle were practically nonexistent—everything was in service of a dream that outpaced the limitations of their surroundings.

This scrappy, unpolished environment became the foundation for Glints—a platform that now connects more than 7 million job seekers with employers across Southeast Asia. Even as the company has grown to employ over 700 people, the core values born in that shophouse—resourcefulness, humility, and relentless ambition—continue to drive its operations. Today, Glints' talent hubs span across Indonesia, Singapore, the Philippines, Vietnam, Malaysia, and Taiwan, yet the spirit of those early days remains at the heart of everything they do.

The Humble Beginnings: A Vision Born from Simplicity

Oswald's entrepreneurial drive was shaped by his upbringing in Singapore. Raised by parents who worked tirelessly in modest roles—his father as an assistant chef and his mother as a kitchen helper—he grew up with values of perseverance, generosity, and a sense of duty to others. His mother's words, "I hope you'll grow up and pay lots of taxes because that means you'll be successful enough to help others," Oswald carried forward the belief that true success lies in being able to contribute meaningfully to others. This perspective would guide his entrepreneurial journey toward building value beyond personal achievements.

From Military Service to Startup Beginnings

Glints was born when Oswald and his high school friends, still teenagers, saw a need to help their peers find internships and job opportunities. With US$30,000 from angel investors, they juggled weekends and free time to build the platform while serving in the military. This risky venture nearly got them into trouble with military regulations, but since the business wasn't profitable at the time, they were allowed to continue after completing national service.

The early days were a mix of excitement and hardship. In 2015, Glints was accepted into Southeast Asia's first accelerator, Joyful Frog Digital Incubator (JFDI). "It was transformative," Oswald recalls. "We were thrown into the world of lean startups, fundraising, and product-market fit. We learned fast and had a lot of fun." Despite the exposure, traction remained a struggle. Recognizing that part-time efforts wouldn't suffice, Oswald boldly decided to drop out of UC Berkeley and fully commit to Glints. This decision wasn't made lightly—Oswald was a first-generation college student who had earned a scholarship to UC Berkeley. After one semester of college, he struck a deal with his college, allowing him to return and resume his studies anytime.

This leap into uncertainty marked the start of a challenging journey that required not just persistence but also strategic mentorship and investment.

The Growth Journey: Funding and Strategic Investors

Strategic investors have been key in driving Glints' rapid growth. Since 2015, the company has raised over US$80 million and is valued at over US$100 million. Key investors include DCM Ventures, Lavender Hill Capital, PERSOL Holdings, Monk's Hill Ventures, Wavemaker Partners, and MindWorks Capital.

Peng Ong from Monk's Hill Ventures, one of Glints' early investors, became a significant mentor for Oswald. Peng's advice to focus on building a company that prioritizes long-term impact over short-term wins deeply influenced Glints' strategic direction. Jeffrey from MindWorks Capital describes Oswald as a hustler with a blend of calmness, patience, and unwavering support for his team—traits that have shaped Glints' growth and culture.

The Power of Biographies and Life Coaches: Building a Strong Foundation

Oswald's growth mindset took root at a young age and was shaped by influential biographies. At just 16, he encountered Tony Robbins, whose philosophy on controlling one's destiny resonated deeply. Later, Richard Branson's rebellious entrepreneurial path inspired him to challenge conventions. "Branson's knack for defying norms and Robbins' emphasis on taking charge of your destiny are principles that have guided me," Oswald reflects. Life coaches have also played a critical role. "Working with life coaches has been transformative," Oswald notes. "My current coach, a former entrepreneur who went public, really understands the challenges I face and helps me stay focused on what truly matters."

The Evolution of Glints: Navigating Pivots and Finding Focus

Glints' journey from a simple internship platform to a leading talent ecosystem in Southeast Asia was far from linear. In the early years, Oswald and his co-founders experimented with multiple offerings—white-label recruitment services, employer branding, events, and job classifieds. "We were doing everything to make revenue, but none of it was scalable," Oswald recalls. The early days were filled with excitement but also constant trial and error as the team navigated a rapidly shifting landscape while searching for a scalable, sustainable model.

After years of iteration, they discovered that the most scalable and impactful model lay in technology-enabled headhunting and cross-border recruitment. By leveraging Glints' growing talent database from Southeast Asia's emerging markets, they could tap into a fragmented ecosystem and provide value where others couldn't.

In 2018, Glints made a decisive pivot, narrowing its focus to cross-border recruitment—a critical move that allowed the company to scale more effectively. The team identified a pressing need for businesses seeking skilled talent across Southeast Asia and decided to concentrate all efforts on this area. The pivot wasn't without sacrifices—Oswald and his team discontinued revenue streams that, while generating income, weren't scalable or aligned with their long-term vision. Instead, they doubled down on building a repeatable sales engine that could support rapid growth. Reflecting on this period, Oswald shares, "Pivoting is about making hard decisions and betting on what you believe is the right model for the future."

The decision to streamline Glints' offerings marked a turning point in the company's growth. By focusing on technology-driven solutions and building a scalable infrastructure, the team was able to create a platform that addresses the talent gaps in Southeast Asia more effectively. The impact was immediate—by honing in on cross-border recruitment, Glints was able to scale faster and generate more meaningful results for clients and job seekers alike.

Oswald's advice to other founders is rooted in these experiences: "In the early days, the key is to look at where the opportunity is rather than going against the flow stubbornly. We focused on areas where things clicked instead of forcing growth in places that felt like uphill battles." He likens this to Warren Buffett's analogy of spending years trying to turn around a textile business instead of focusing on the more profitable insurance sector. For Glints, recognizing where to double down and when to pivot became critical to their success.

The Impact: How Glints Transformed Lives and Businesses

The true measure of Glints' success lies in the lives it has transformed. At a Jakarta tech conference, Oswald met Arba, a young volunteer who shared a touching story. Before discovering Glints, Arba was set on a predictable path—working at a bank or joining a large corporation. But finding Glints opened doors he never knew existed. Through Glints, he landed an internship at a startup that exposed him to the world of entrepreneurship. His career aspirations shifted, and today, Arba dreams of becoming a founder himself—an ambition fueled by the experiences he gained and the career content he devoured on Glints.

Businesses have also reaped the benefits of Glints' unique approach. Take the case of a small IT firm in Singapore that consistently lost out on developer talent to bigger players. With Glints' help, they built a robust tech team in Indonesia, transforming their fortunes. The firm eventually became one of the most sought-after IT companies in Singapore, and the founder, after a successful exit, now turns to Glints for talent for his new venture.

A more prominent example is a large insurance company burdened by high costs in Shenzhen. They partnered with Glints to shift operations to Southeast Asia, building a 150-person team in Indonesia at a fraction of the original cost. They've since expanded across Malaysia and the Philippines, a move that has kept them competitive in their industry's digital transformation.

Growth Strategy: Knowing What to Measure

One of Oswald's greatest strengths lies in knowing what to measure. For Glints, the North Star cannot be revenue. "If revenue is the North Star, there are 10,000 ways to make revenue, which leads to a lack of focus," Oswald explains. Instead, Glints' North Star for its platform business is "connected opportunities"—how many successful connections are made between candidates and employers. By focusing on the right inputs, such as matching CVs with opportunities, Glints has built a platform that delivers meaningful outcomes.

Learning from Mistakes: The Art of Making People's Decisions

Oswald is candid about the hard lessons learned from making the wrong people's decisions early in Glints' journey. Without a structured hiring process, the company encountered cultural misalignment and leadership challenges. They discovered that hiring based solely on technical skills or credentials could create toxic environments if there was a misalignment with the company's core values.

To address this, Glints codified its cultural principles, including fostering a beginner's mindset—remaining humble and open to learning despite success. Oswald now prioritizes hiring based on both skills and cultural fit. "We've had to let go of some really smart people who just weren't the right fit for our culture," he admits. The company now relies on structured interviews and value-based assessments to ensure candidates align with Glints' mission.

In hiring, Oswald seeks three key traits: smartness, humility, and motivation. He emphasizes that intelligent problem-solvers with growth mindsets are essential in startup environments, where adaptability and generalist skills are crucial. Equally important is humility; Oswald believes that low-ego, high-self-awareness team members collaborate better and avoid internal politics. Lastly, intrinsic motivation ensures alignment with the company's long-term vision. Oswald often asks candidates about the last time they received negative feedback to gauge self-awareness. "When I ask this, some candidates get defensive right then and there—it's very telling," he jokes. Oswald is also known for his thorough diligence, often making as many as ten reference calls for key hires to ensure both cultural and skill fit.

The Future: AI and the Next Chapter for Glints

Oswald is excited about AI's role in reshaping recruitment. Glints already use AI for job matching, but the future holds even greater potential for personalization and efficiency. "AI will make hiring smarter and more tailored to each individual," he predicts. Glints is poised to lead this transformation, ensuring that both employers and job seekers benefit from these advancements.

Glints'" Enduring Vision

Glints' long-term vision is ambitious: to empower 100 million people in Southeast Asia with career opportunities and build the region's leading talent ecosystem. Oswald sees Glints as more than just a business—it's a legacy that should endure for generations. "I want this platform to be something my son Leo could use when he grows up, whether he's searching for talent or looking for his first job," he shares. To make this vision a reality, the company focuses on building an enduring organization rooted in the right culture and a sustainable business model.

As Glints continues to expand and lead with AI-driven innovations, Oswald's unwavering commitment to these long-term goals remains central to the company's journey. The path may have evolved from those early days in the shophouse, but the spirit of resilience, adaptability, and heart that built Glints remains its driving force.