Jay Olos joins as CFO of PayMongo

I'm super excited to announce that Jay Olos has joined PayMongo as our Chief Finance Officer. Jay is our first senior hire, and he brings years of extensive international leadership background in finance, treasury and risk management, among his impressive list of experience. He was part of the founding team of Compare Asia Group where he handled the company's Series A and B—raising a total of $110 million in total capital. Most recently, he served as the CFO of GCash, one of our strongest e-wallet partners, where he led significant improvements in the company's finance processes and brought it to much better scalability.

Over the last quarter, Jay worked with me closely as a consultant, helping me and the management team streamline our core accounting practices. But what got me super excited about Jay when we first met were the diversity of his experience and his strong passion for business. On the side, he also helps others learn more about running a business, making wise investments and doing effective financial planning. He runs online courses on investing and stock trading. I couldn't be more thrilled in working alongside Jay! I'm personally excited to learn from his knowledge and experience.

At our core, PayMongo is a finance and treasury company. Finance is embedded in our products and services. Building scalable financial systems is key to the future of online payments. This means our own treasury capabilities must be excellent. Jay couldn't be more suited for the job. He will lead the integrated financial systems and processes that run the company—ensuring that our customers and business partners succeed in their own endeavours.

To make things even better, Jay is a PayMongo customer himself! Welcome, Jay; I am excited to have you on board.


Since starting PayMongo, a lot of folks have asked me what kind of a co-founder they should look for. I have been told over the years that the co-founders we pick can mean the difference between success and failure of a startup. Still, it wasn’t until PayMongo that I had indeed seen first hand how the grit and passion of a person drive a company.

Every great startup would have at least one person who will push the energy and the drive to make things happen in the company. For me, I’m more than privileged to work with my co-founder and friend: Luis Sia.

I have known Luis since 2014, but I have never worked with him as closely as I do now. Seeing how he can rally everyone even in the most challenging times of building a startup, I am confident that PayMongo would not have been possible without Luis.

He is formidable and committed. I pitched him the idea of PayMongo early in 2019 over sushi and sashimi. He asked me a few questions during that dinner then decided he was in. At the time, we had zero code, no funding and unsure of most of the next steps to take. He started planning logistics and committed to tangible milestones we could achieve. Since then he has been entirely in, from relentlessly gathering all the possible partnerships to obsessively recruiting the best people to add in the founding team.

He is open to new ideas and feedback. As the person in charge of the growth team in the company, Luis is incredibly effective in working across different groups. He is always willing to hear out new ideas and can quickly process them. While he would come in meetings with strong opinions and narratives, Luis is always open-minded and thoughtful in working out something to push our vision forward. I am comfortable providing him feedback on managing teams and setting expectations, without getting offended, just as much as he offers candid advice to me.

He is an incredibly fast learner. Jaime and I were both busy designing and writing code at the beginning. At the same time, Edwin focused on figuring out our compliance and regulatory obligations. Luis made sure that the business was running smoothly even with limited information and a product that was clunky at times. With little background in fintech, he stepped up to learn the inner workings of how a payment platform works, both in the technical and business sense.

Luis played the role of the non-technical technical co-founder, which is impressive and rare to find around here. He is an engineer by training and a great entrepreneur in practice. His understanding of technology allowed him to effectively execute on many of the non-technical roles: pursuing partnerships, selling the product, acquiring the right customers, letting everyone work out of his house, getting the contractor for our new office, among others. In a small startup, many people would gloss over the importance of having someone great in this role.

Founding teams need influential leaders who can drive the vision of the company and keep everyone motivated despite the challenges that will eventually come along the way. While it is indeed also necessary to have an excellent technical team to build a tech startup, I cannot underscore the importance of having a co-founder like Luis. You will have hit the jackpot if you find someone like him because we surely have been.

Thanks to Abi Valte, CB Ablan and Coby Lim for reading drafts of this.

2010s: Lessons from the decade that was

From the iPhone 4 to the landing of the Curiosity rover on the Red Planet, to changing political landscapes around the world—the 2010s were full of ideas and lessons learned. As this decade ends, I am now CEO of a Y Combinator startup based in Manila doing online payments, PayMongo. This story may sound all nice and rosy, but my last ten years did not go by without its bumps and bruises; it even all started with an unimaginable challenging first semester at MIT when I entered at the age of 16. I’ve since had my fair share of hard lessons. As they say, the days are long but the decades are short, indeed.

As we approach the next stretch, I sat down and took a hard look at what has flown by. For what it’s worth, here are ten life lessons I learned along the last decade, in hopes that this will help you along your own next ten.

  1. Seek and embrace failure early. I've failed more times than I'd like to admit. In my first term at MIT, I bombed two classes: Calculus and Physics. It was a massive blow to my ego, mainly because I was great with numbers in high school. I was frustrated, and I felt like giving up. Luckily, I was fortunate enough to get all the support I needed to come back stronger, thanks to TAs spending countless hours going through class materials with me and friends being there for me when I needed a shoulder to cry on.

    But it still wasn't a Cinderella story—the next few years were dotted with more significant failures and rejections both in my personal and professional lives. I would be rejected for jobs and internships at companies like Facebook and Google. I would fail to get into Y Combinator—twice. I would fail in my personal relationships and lose friends in the process. Having experienced failures early in life allowed me to develop compassion, empathy and that oft-thrown about word called “resilience.” There was nothing else I could do but get back up, dust off my knees and keep aiming for the moon and the stars. No setback, big or small, should take us away from our goals.

  2. Take more risks while you're younger. Youth is a great asset. Don't live a cautious life in your 20s. Travel to unknown places. Learn a language; better yet, learn many. Get to know a lot of new people. Fail in business—and fail multiple times. Don't be afraid of heartbreak. To date, I have travelled to almost 40 countries and met a lot of new people; I have also failed in multiple companies (from the crazy idea of peer-to-peer shipping to the chaotic world of election analytics!) and numerous relationships and blew more money than I should have. It's okay to not have the fattest bank account just yet. No money in the world can recover all the time that has passed you by. See the world, meet people and grow old having great stories to tell your kids and grandkids.

  3. Remember: The rules, like streets, can only take you to known places. We were all raised and taught to follow the Yellow Brick Road, because, like Dorothy, it's supposed to take you back to Kansas. It is easy to focus on that clear, laid out street towards success. You find yourself setting rigid rules, rejecting things that you feel are not helping you get there. You refuse to talk about topics that are “unrelated” to your work. You disengage in friendships or reject relationships that you think are unconventional or outright distractions.

    Back in college, starting my own tech startup never crossed my mind. In fact, I was pretty set with my plans after graduation: get a high-paying Silicon Valley job; stay in the US for at least five years and own a blue passport; buy a house and live a comfortable life in Palo Alto.

    None of that ever happened.

    I am paid way less than what I could be earning now in San Francisco. I have just my good ol’ maroon passport. And, though still living comfortably, I don't own a house in Palo Alto.

    But all those hours talking to my college advisor who encouraged me to try entrepreneurship, all those nights spent hanging out with Sloan students and all those other diversions I had opened my eyes to unforeseen paths. And these uncharted roads took me to become a leader I never thought I would be. I left a comfortable life in the US to pursue the challenging—sometimes frustrating—world of startups in Manila. I look back knowing I regret none of the decisions that brought me to this point.

    Would I have been happier had I stayed on the Yellow Brick Road and lived in the US? It's impossible to know the contrary, but I am fulfilled with my choices.

    I learned that while having clear goals is essential, in practice, be fluid. As Bruce Lee once said, “Be like water.” Rigidity won't allow you to succeed when faced with a rock, but fluidity allows you to go under, over and sideways. Great opportunities in life don't always come wrapped in pretty bells and whistles; some come in unappealing brown bags like yesterday's lunch. Some decisions may seem slightly reckless, if not downright dangerous. If the path appears to be clearly laid out, it's not your path.

  4. Your family, friends and your significant other should always be on top of your priority list. In the hustle and bustle of daily life, it's easy to lose track of your most important relationships—especially in your 20s when you feel the need to sacrifice your constants in order to prove yourself. I was very much guilty of this. I used work as an excuse not to be present during the important milestones in my friends’ lives. Starting a company in the Philippines is already hard enough, let alone time-consuming. But one thing I learned: always make time for your family and closest friends. Go to parties with them. Talk about something meaningful outside of your work. Remember that ideas come and go, but relationships remain even after you can't code anymore.

  5. Keep your circle small. Surround yourself with smart, ambitious people. I realised that what made MIT special was not just its renowned name or the whispered awe it evokes from people but the kind of peers one would have as a student there.

    There is truth to what others say that you become the average of the people you spend most of your time with. The few friends I have are the ones who keep me grounded but ambitious. Forge deeper relationships with just the people who are genuinely important to you. Work for them. Hire them. This also means that you have to be ruthlessly selective. It's okay to have fewer true friends whom you can rely on when things get tough than to have a large number of acquaintances who run at the sight of trouble.

  6. Don't be afraid to fall in love. We work so hard every day to keep our hearts from getting hurt. Not only because it's easier but also because it's part of our survival instincts. Here's my take: don't hold love back. Fall in love with moments, with new experiences and with beautiful places. Fall in love with people who are special in your life. Be vulnerable, choose the thrill and be open to get hurt. For some reason, we grew up convinced that avoiding love means protecting ourselves. It may sound easier holding our love tightly, but it's never better. Choosing love means letting go of judgement and apathy. Laugh with the people you love. Cry when you are hurting. Ask the hard questions and listen to the answers genuinely. Get to know people deeply. And let go of the fear of judgement. By falling deeply in love, we become better versions of ourselves.

  7. Say yes, before knowing how. During freshman year in college, I joined a group of Stanford and MIT students who were extremely passionate about service leadership. Part of our mantra was saying “yes” to things before knowing how to do them. It sounded crazy at first; how am I supposed to commit to something I don't know? In hindsight, saying “yes” before I was ready had a profound impact on shaping my leadership skills. When I was sent to lead a project in Southeast Asia with other college students from different countries, I first thought of all the reasons why I couldn't do it. I did not have any international leadership experience; I had never fundraised for such a large scale venture; I had never had to convince other students to join my cause. It didn't feel like I was cut out for it.

    But that one “yes” altered the course of my life. Over the years, all my yesses turned into things I hadn't imagined before—starting a company (and nearly running out of cash), taking on an entirely new role, raising money from VCs, building a team and even starting a relationship. Our character is shaped by our actions, our willingness to figure things out along the way, to learn, to ask the hard questions and to accept that we may fail in the process. Let's keep trying out our firsts. Before we know it, we'll have pushed our limits and have created change with lasting impact on others.

  8. Be optimistic. Saying that starting PayMongo was not easy is an understatement. It was a struggle from day one. We never planned on doing payments at all. Late last year, our pioneering team of seven was just booted out of another startup I co-founded. We had zero external funding and had barely any money left. We turned to outsourcing our skills. From one proposal to another, we spent three months trying to convince all sorts of companies that we were the right engineering partners for them.

    We weren't closing any deals. We had all the reasons to give up. But against our natural pessimistic instincts, we kept on hustling. I had to take charge of keeping an optimistic environment in the team—keeping everyone motivated, ambitious and energetic. We had to think of an idea that was both impactful and buildable. And thus, PayMongo was born. We decided to apply to Y Combinator just three days before the deadline. This time, YC did make a bet on us; the rest is an ongoing story.

    I have always been told that great founders are overly optimistic. They are optimistic because they can see great opportunities behind every challenge, obstacle and setback. I say that we all, even non-founders, should be optimistic. Better yet, be intentionally optimistic. While this sounds reasonable, it is actually hard to do. It can be a struggle to think positively when we live in a world where problems are endless. Optimists, however, are the ones who end up changing the world. I have yet to change the world, but having positive energy around you is both encouraging and contagious.

  9. Learn new things. I was sceptical about the importance of learning humanities or social sciences coming from a strong engineering background. Convinced that I learn better about fluid dynamics, electromagnetics, the ever-expanding universe and what have you, I never really minded studying things like business or the famous riots in America or microeconomics or the Eurozone crisis.

    Things changed when I spent more time with friends studying philosophy. We discussed big questions. Why do we exist? What are the ethical implications of artificial intelligence? Are the abilities of machines limited by the skills of those who made them? I was challenged to engage in topics I barely had any knowledge of. I started having a deeper appreciation of my purpose as a software engineer and, in turn, as a human being. I realised that science and technology don't exist in a vacuum, that learning about more of their global contexts can deepen our understanding of the world.

    If you're interested in mechanical engineering, learn about the impact of the products you design can have on the rest of the world. If you are a software engineer like me, learn how computers shape the way people think and how the way people think shapes computers. And if you are a non-technical person, try to code and learn how you can communicate the business requirements better with your engineers.

    Being open to learning new things, especially those that are outside your core, is a gift that keeps on giving. It removes your pre-disposed stereotypes and makes you more open-minded. It makes you a better problem solver and, in turn, it'll make you a better person. In running a business, I am now more confident in making big decisions even in unfamiliar situations, knowing that, one way or another I can learn.

  10. The days are long but the decades are short. To summarise the above, I take this last piece of advice from Sam Altman. If there's one thing that money can't buy, it's time. Time goes by fast. So don't spend your time doing things that you don't love or enjoy. Don't let others’ judgement limit who you are and what you can do. Forget that so-called image you work so hard to preserve. Few people will remember you hundreds of years from now anyway. Knowing that, in the grand scheme of things, you are insignificant can be liberating. Be who you are and do things that make you happy. Spend time with people you care about and cut negative people out of your life.

    This is the only life we get, so get things done. Take your chances. Grow old knowing you have lived fully and without regrets. So, pursue the career of your dreams, build that idea you have been thinking of for years, travel to places you have always dreamt of going and tell that boy or girl that you like them—this life is not a dress rehearsal.

Thanks to Abi Valte, CB Ablan, Coby Lim, Edwin Lacierda, Julio Villafuerte, Karl Corro, Luis Sia, Martin Gomez and Rita Chang for reading drafts of this.