Pam and Winston Damarillo’s love story begins, fittingly, with a bit of entrepreneurial problem-solving. “I still remember what she looked like when I first saw her,” says Winston, “and I knew I wanted to be with her. The question was how.” They were freshmen in Manila at the time. A natural organizer, Winston pitched and organized a Freshman Club that would support students’ transition into college – and conveniently, give him and Pam an excuse to spend more time together.
It worked. The two of them spent the last half of college together as a couple, and when Pam left for the US after graduation, Winston joined her several months later.
Fast forward to 20 years later and they are now a happy couple with a home and a son in LA, initiatives across the Philippines, and footprints around the world. Today, Winston is known as a serial entrepreneur and a leader in digital transformation in the Philippines. A true jetsetter, he flies between from the US to the Philippines about three times a month to build his companies and lead PLDT’s Chief Strategy Office. On her side, Pam is an active volunteer, educator, and an aspiring entrepreneur with her eyes set on on new applications of technology in the education space.
Beyond this, they are mentors and active supporters of entrepreneurial Filipino talent – champions of a Philippine nation that truly leads on the global stage. Over more than 20 years, they have embodied circular migration, making the most of their positions as people with one foot in the Philippines and the other in a different corner in the world. For me, a young Filipino growing a venture and working to build the same bridges, the two of them together have formed a strong pillar of inspiration and support.
What was it like during those first few years in the US?
Pam: In the early years, it was much harder. I worked 12-hour shifts as a nurse. We joked that we had a “breast feeding exchange program” – around noon, I would pump breast milk for our son at the hospital, Winston would cook lunch, and we would meet at the parking lot to exchange goods. When Winston got the VC job with Intel, it allowed me to stop working for a while and focus fully on being a mother.
Winston: When I moved to the US, I knew that I wanted nothing less than the best. I was going to work for Intel or IBM, or I wasn’t going to work at all.
I ended up spending almost a year on my uncle’s couch, and eventually realized that they weren’t going to hire me based on my resume because I didn’t have the greatest resume or credentials. I didn’t go to a school that they recognized. So instead, I spent a few months creating my own software, then contacted Intel and told them, “I think you’ll like this…”
That was the start of the rest of my career. At Intel, I started as a programmer, then eventually made my way to business development and eventually venture capital. I was lucky to have great mentors along the way. One day, I remember being out jogging and decided right there that I was going to leave and start my own company.
That first company failed. I raised $10 million off of a business plan on the back of a napkin, then had to stop it and give half of the money back to VCs. Our mistake was that we were less interested in running a company than we were in riding this tech wave.
When did you know you were going to be an entrepreneur?
Winston: My dad was an entrepreneur. He started out poor, built his own business, and was well off by the time I was around. Then we lost it all. When it happened, I had already enrolled at La Salle, and had to figure out a way to make it to college. My mom and my aunt supported my tuition, but eventually I had to figure out how to make my own money. So in college, I started my first business selling bulldozer parts – with a bit of help from relatives, who were my first clients and brought in my first referrals.
I think what allowed me to be an entrepreneur was exactly that experience, which taught me what it felt like to lose it all and start from nothing. Entrepreneurship is made up of moments like that, and I was lucky to learn resilience when I was young.
There will always be that S-curve in entrepreneurship. My first company failed, then we revived it and sold Gluecode to IBM. Since then it’s been cycles of boom and bust. Acaleph and Exist have done well, but other ventures since then have been less successful. Each time, I learn more about running a company and being a leader. And each time, I trip up and make some new kind of mistake.
How has the Philippines changed since you first left?
Winston: Entrepreneurial confidence and ambition are growing. What’s missing are the institutions that make the process of creation easier; the infrastructure that can accelerate indigenous creativity; and an international perspective that really believes in the Philippines as a place where globally relevant solutions can start. Once we have those three I’s, then things will advance much faster.
Pam: One thing that’s exciting to me is that there are more and more people who are coming back home. It wasn’t always like that, and it says a lot about the changes that are happening here, as well as how Filipinos abroad have come to rediscover the resilience and beauty of the Philippines.
Winston: It’s also important that people aren’t just coming back here to “help” – they’re coming back here to prosper. They’re not here to do charity; they’re here to do well. And that’s important because it means people realize that the Philippines is where the future is taking shape.
How has your role evolved in relation to the Philippines?
Winston: I think a lot about the names of my ventures. They come in 3 phases. The first few companies had names that were very “made in America”: Gluecode, Exist, Logicblaze. After that, everything ended in “PH” for “Philippines”: Mor(ph)labs, Acaleph. Now it’s all Filipino names: Amihan, our digital transformation consultancy, which is named after the Filipino trade wind, and Talas, the data analytics startup within PLDT, which is Tagalog for sharpness, as in a cutting edge.
My approach has evolved in a similar way. First it was about borrowing global ideas and architectures from abroad; then it was making it all accessible in the Philippines; now it’s about cultivating ideas that are indigenous and truly from here. The Philippines as a leader in the global conversation.
This also affects how we do our advocacy. I understand the importance of creating social services and creating new institutions, but now I’m more focused on creating networks that allow others to build out their ideas and find partners for growing them.
At Amihan, we’re shifting our strategy in this direction. We’re no longer just going to do strategy consulting; we’re creating a platform on which people can create their own initiatives, build their own teams, and scale their own ideas through our tools and networks. We’re creating a new workspace where innovation teams from different large corporations and institutions can work side-by-side with small ventures and innovators. At the center of that space will be a marketplace where the new ideas can find institutional partners, funders, or buyers that are interested in them.
I don’t want to be just another VC funder. Entrepreneurs need funding, but the worst thing you can do at this stage is give a Filipino entrepreneur a million dollars and tell them to turn it into a billion. More important than anything, they need customers.
On the other side, I’ve seen that large companies are now hungry for ideas on how they can adapt and be innovative. But they’re not finding the ideas that are relevant to them. My role is creating the platforms where those two sides can connect.
Pam: For me, I’m excited about learning and technology and what they can mean in the context of the Philippines. We’re planning to create a school in Cebu where we can house scholars, teach them about new technologies, and connect the to the opportunities where that kind of knowledge can have the most impact. Now we’re also starting to ask ourselves how to leverage this as a way to support social entrepreneurs.
Winston: Not to mention Pam continues to be my best management consultant. She took a class, told me about it, and that became my next venture. I’ve also learned from her to change the way I do things and work with people: from acting like the genius in the room to really understanding people, encouraging them, and enabling them to build what I can’t. Through this, letting a thousand flowers bloom.
Do you have a message for other global Filipinos?
Pam: Don’t be afraid of being Filipino. Celebrate your identity. When I first moved, everything was about assimilating, fitting into a white America. I used to be afraid of cooking adobo when friends are over and scaring them with the smell. But now it’s different. Now, I can say: I am Filipino and proud of it. And that’s fine.
Winston: Young people especially need to come back to the Philippines. If you’re young, you need to be where growth is happening – and it’s not happening in Europe, it’s not happening in the US to the same degree. But it is happening in the Philippines.
Winston Damarillo is a tech entrepreneur who currently chairs Amihan Global Strategies and is Chief Strategy Advisor at PLDT. Pam Ros Damarillo is an educator, volunteer, and an active supporter of education and entrepreneurship in the Philippines and beyond.
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