Rashmi Kwatra, Founder of Sixteenth Street Capital, invests in people, purpose, and prosperity

Effortlessly chic, possessing a million-dollar smile, and entering a room with ethereal grace, Rashmi Kwatra, Founder of Sixteenth Street Capital, is a consummate professional. She is a seasoned-skilled expert, upholding integrity and ethics, accountable and self-regulated, and consistently demonstrates her generosity of spirit—not to seek personal recognition, but to allow others to shine in their deserved spotlight. In other words, she lets her work and passion behind her communal impact do the talking. From graduating top of her class at International School Bangkok (ISB) to carving her path through the prestigious Wharton School at the University of Pennsylvania, her momentous run to becoming the youngest partner at Prince Street Capital Management—a hedge fund with offices in New York and Singapore—solidified her influential and lasting impression in the world of finance. Having founded Sixteenth Street Capital eight years ago with a tight-knit team and offices in Singapore, Mumbai, and Bangkok, she oversees and manages close to $1 billion in investments in today’s market. But there is a deeper purpose fuelling her transformative effect on the community she hails from: meaningful growth. Masala had the pleasure of discovering the essential elements that have gotten her this far and what is to come.

How was your upbringing in Thailand, and what led you to create a base in Singapore?

I had a unique upbringing in Thailand, where my family has been rooted for four generations! Whenever people comment on my achievements, I think back to my great-grandfather Moolalmal and his brother Amarnath, who walked all the way from Punjab to Bangkok, perhaps with a few boats in between, all in search of opportunity. They began by selling textiles door to door before opening a store and then importing fabric scraps from Japan and exporting to other markets in Southeast Asia. Incredible! Each generation since has built something new and remarkable. That spirit of entrepreneurship and resilience seems to run in our family through generations. On my mother’s side, my grandparents moved to Thailand during partition, and together these journeys gave my sisters and me the privilege of calling Bangkok home. Our parents emphasised education and connection, so we attended ISB, where we were exposed to many cultures and were encouraged to pursue our passions in academics, arts, and sports. Though life wasn’t without its hardships, we were fortunate to be surrounded by a very loving extended family and a close-knit community, which gave us a strong foundation of togetherness. After graduating top of my class at ISB, I went on to Wharton. While I loved my time in the U.S., I wanted to be closer to home for my family while pursuing my career ambitions. Given the close proximity, just a two-hour flight from Bangkok, and its status as a global financial hub, Singapore became the ideal destination, making it the natural place to build a base.

Could you give us a brief explanation of your professional responsibilities, sort of your day-to-day for those unfamiliar with your line of work; what does your job entail?

At its core, my work requires a very long-term mindset and a deep understanding of people and businesses. My father, a great businessman and investor, introduced me to investing early on and emphasised the principles of long-term and strategic thinking. He handed me three books when I was very young, which I highly encourage our youth to read: The Intelligent Investor by Benjamin Graham, Common Stocks, Uncommon Profits by Phil Fisher, and How to Make Friends and Influence People by Dale Carnegie. My father’s experiences, and plenty of reading, taught me that great investing is about identifying exceptional people and sustainable businesses. But perhaps the most important lesson was the power of compounding. Not just in investing, but in life: the way small, consistent choices build into extraordinary outcomes over time. Whether it’s relationships, health, knowledge, or capital, what you nurture steadily is what grows meaningfully. At Sixteenth Street, my team and I focus on identifying Asia’s strongest management teams—leaders with vision, resilience, and alignment—who are creating products and services that add genuine value and have long runways for growth. Day to day, this means researching businesses in depth. We speak to leaders and their teams to see why and what is behind their strategic decision-making. Do they think long-term, and are they acting in ways we, too, believe would be sustainable and beneficial for all stakeholders? We analyse financials, speak to competitors, suppliers, and customers, and build out our assumptions of what the future of their impact could look like. We then decide if we can partner with these companies and grow alongside them. We invest with the mindset of being business owners, not traders. That’s why our portfolio of companies that we invest in is concentrated—about 20 companies that we know inside and out. For us, adding a new portfolio holding means making room, so capital allocation and portfolio positioning are critical parts of my role. Our clients are mostly philanthropic trusts, endowments, and family offices of entrepreneurs who trust us to allocate their capital in Asia and do so with integrity and high returns. Beyond investment decisions, I mentor my team, build trust with our investors, and lead philanthropic projects in financial inclusion and community development across the markets we invest in. I’ve come to see that the power of concepts like compounding and the importance of financial inclusion are still not being taught early enough. That gap makes me feel an even greater responsibility to spend more of my time helping to embed these ideas into education and community systems, so the next generation is empowered to create resilience, collective well-being, and opportunity.

From Wharton to becoming the youngest partner at an institutional fund, then launching your own—what internal shifts did you undergo along the way? Were there personal beliefs or fears you had to unlearn to even take that leap?

My drive has always been internally motivated. I have never been motivated by achieving any financial goal except financial independence. While I was at Wharton, I interned on Wall Street and was being offered jobs at investment banks, but I realised I didn’t want to spend years in transactional roles. I wanted to earn skills that transferred into building independence and lasting impact. Family was another motivator. With two sisters, my mom, and my father’s health scares from an early age, I felt the responsibility to excel in his craft so I could support them. That gave me the fuel to give 100 percent, to learn, to contribute, and to grow, not for external recognition but to build enduring skills and help provide. When I joined Prince Street Capital, it was because I knew I would gain the right skill sets, the exposure I was seeking, and the guidance of strong mentors. My mindset then was simple: learn, learn, and learn more; give, give, and give more. As my contributions grew, I became the youngest partner at 25 years old. Still, I felt the need to test myself as the ultimate decision-maker and to create something sustainable. Launching Sixteenth Street at 28 meant walking away from a lucrative, comfortable role into uncertainty. But for me, real growth has always meant leaning into challenges rather than settling for comfort. Eight years into Sixteenth Street, I remain a student every day. Early on, I poured much of my energy into proving myself, often taking others’ opinions too much to heart. Over time, the biggest shift has been learning to trust my own conviction and letting our philosophy, discipline, and grace guide the way we build.

What were the initial challenges in getting Sixteenth Street Capital off the ground?

One of the biggest initial challenges was that I had to wear so many hats, and as a business builder, I still do. It wasn’t enough to rely on my investment acumen. I had to convince clients to place their trust in me, while at the same time building an operational infrastructure that could rival much larger funds. In fund management, you can’t hide behind size, you have to offer the same robustness, governance, and discipline as a billion-dollar firm from day one, while also adding value in ways that make you distinctive. For me, that meant not only demonstrating that I could identify great investments but also creating the systems, relationships, and culture that would allow Sixteenth Street to grow sustainably. Balancing those dual responsibilities—investor trust and institutional strength—wasn’t easy, but it was essential to laying the foundation for a firm built to last.I had also seen many funds launch with sweeping promises, only to struggle to deliver. I wanted to take the harder but steadier path, never overpromising, always staying aligned. That meant working with local service providers who understood our markets, taking the time to build processes from the ground up, and prioritising sustainability over speed. It may have slowed the journey in the early years, but it ensured that we have today an institution designed to endure.

How have your Thai-Indian roots shaped your investment philosophy and leadership style? Are there cultural values – perhaps around family, community, or perseverance – that you consciously bring into your firm’s ethos.

Absolutely! The values of long-term vision, perseverance, and reciprocity that brought my great-grandparents here are the same values that guide Sixteenth Street. Family and community are central, as my grandparents and parents emphasised education, connection, and responsibility; I believe investing is about more than returns. It is about uplifting communities and creating durable development. And like many immigrant families, grit and resilience are in our DNA. Those qualities, combined with grace and generosity, are the foundation of our culture.

In a male-dominated industry, what’s a misconception people have about being a female fund founder in Asia? What do you wish more people understood about your experience, and how do you navigate that day-to-day?

A common misconception is that leadership in this industry has to look one particular way. My experience has been different. I tend to lead from the heart, which I see as a strength, not a weakness. For me, that means mentoring and developing talent, investing in businesses that contribute to long-term development and well-being, and creating a culture where people feel safe to take risks, learn from mistakes, and ultimately perform at their best. The proof is in the outcome as we’ve delivered strong returns while fostering a culture of purpose, collaboration, and trust.

You’ve said you approach public market investing with the discipline of a long-term, private equity mindset. How do you cultivate that mindset in your own life, especially in moments of noise or short-term pressure? Any personal rituals or mental frameworks you lean on?

I cultivate balance. I play tennis multiple times a week, strength train, practice yoga, and dance. Physical activity keeps me fit, clears my mind, and is just so fun! Spiritually, I spend a lot of time with family and friends and find myself singing mantras in the shower every morning. Long-term investing is as much about temperament as analysis. Caring for your health, your mind, and the bonds with family and friends creates the steadiness to look past the noise and stay focused on what truly endures.

As a founder who co-invests most of her wealth in her fund and aligns with long-term investors, what legacy do you hope Sixteenth Street Capital leaves behind—conceptually, culturally, even personally?

Conceptually, I hope we are remembered as a firm that proved you can compound capital sustainably in South and Southeast Asia—delivering world-class returns without ever compromising on integrity or responsibility. But beyond investment results, I want Sixteenth Street to stand for development in the broadest sense: developing talent, deepening markets, and contributing to the long-term progress of the region. We are not just an investment firm at our heart, we are about people, supporting the entrepreneurs we back, the team we mentor, and the communities we serve. Culturally, I hope Sixteenth Street is remembered as a place where people grew and felt a deep sense of purpose, both professionally and personally. A place where mentorship, mutual respect, and shared mission defined the environment. In an industry often driven by short-term pressures, I want our culture to stand for heart-led excellence and a belief that success is greatest when it is shared. Personally, I hope our legacy mirrors the journey of our community here in Bangkok: building opportunity not only for ourselves but for others. Through thoughtful capital allocation, philanthropy, and mentoring the next generation, I want us to leave behind more than financial results. I want us to leave behind opportunity, dignity, and shared prosperity across Asia.

For your younger self graduating with Wharton honours, what’s one piece of advice you’d go back and whisper to yourself?

We often debate what matters more: the journey or the destination. But in truth, it’s the company you keep. I’d tell my younger self to trust her instincts, believe in herself, and only surround herself with people who align with her values. Everything else follows from there.

Who were your inspirations, influences, and mentors along your professional journey?

For one, my mother. She is the most giving soul I know, and she’s always shown me how to welcome others with an open heart and spread warmth. The biggest part of my job is not reading balance sheets or crunching numbers; it’s understanding people. That gift, the ability to connect with and truly see others, comes from her.

Then, there is my father.

His willingness to teach and share his experiences so transparently deeply influenced my path. He had a remarkable global and long-term vision, and he ensured I had every resource to pursue my goals. He encouraged me to take risks, giving me the comfort of knowing he’d be there to catch me if I fell—something he still jokes he’s waiting for. Finally, my grandfather. His advice was clear: never take a loan or owe anyone money. And if you ever lend, do so with the mindset that it’s a gift, without expectation of return. That perspective instilled in me a deep sense of discipline and grace in how I approach finances and relationship. Oh, and maybe Oprah Winfrey. [Laughs] Because she’s the ultimate boss lady. She’s defied racial and social norms, but what inspires me most is how she uses her success to uplift others and share knowledge in a way that feels authentic and lasting.

Which industries or trends in the coming years are you looking forward to exploring or investing your time and effort in?

The case for investing in South and Southeast Asia is only just beginning. Our portfolio today is almost evenly split between India and Southeast Asia, where we see the strongest tailwinds: demographics, rising consumption, productivity, and entrepreneurship. We’re backing founders who are creating real value in people’s lives, whether through digital access, financial inclusion, or alternative healthcare. For instance, we have a large exposure to a healthcare company that draws on eastern traditions like Ayurveda and homeopathy, which we believe will continue to grow as health is redefined more holistically. As people in Asia get wealthier, we also see enormous potential in wealth management—not just for the wealthiest families and organisations, but for companies that can educate and empower the wider population to save, invest, and compound for the long term. Beyond investing, I spend a lot of my time thinking about how to create lasting, positive change for the next generation. I was fortunate to learn early about financial inclusion, the power of compounding, and the importance of balance—mental, spiritual, and emotional. Many young people don’t get that exposure early enough, and part of my role is to help bring those lessons into education and community systems so they endure. To me, the challenge and the opportunity lie in ensuring that as technology accelerates, we also preserve choice, connectivity, and shared well-being at the core of our communities.