Five years ago, I left Apple to embark on a quest: 

How might we radically transform the Philippines in our lifetime?

This question has birthed Dream Bigger which is now a group of companies. Over these years, I’ve had the privilege of listening, experimenting, co-creating community, co-leading an accelerator, investing in founders, raising a fund, launching an offshore service company, training leaders and learning what it takes to move the economic needle in the Philippines.

This newsletter is my attempt to think out loud and find the others asking similar questions so we might learn and dream bigger, together. 

Every issue brings you a problem worth solving, an experiment worth testing, a builder worth knowing, and a practice worth considering. 

Sometimes the content will come from me. Other times it might come from the community. The format will evolve. What won't change is the question at the center of everything: how might we radically transform the Philippines in our lifetime?

If you have a story, an experiment, or an idea worth sharing, just reply to this email.

Welcome to How Might We?

— Christeen

The Philippines is one of the happiest countries in Asia. It is also one of the most quietly broken.

Here are the numbers I can't stop thinking about:

These aren't statistics about strangers. These are families we know and care about. The backstories behind businesses we invest in. The weight that Filipino entrepreneurs carry into every pitch.

The root cause of almost every systemic challenge in the Philippines — poverty, corruption, stunted economic growth — traces back to family breakdown.

So what does this have to do with business?

Everything.

When a business pays a living wage with benefits, a father stays home instead of shipping out to the Middle East. When a mother builds a company in Cebu instead of leaving for North America, her kids grow up watching someone build instead of someone leave. When companies cultivate healthy workplace cultures, parents go home to their kids with energy to engage, not burnt out or tuned out.

Business is not the only answer. But it is one of the most powerful vehicles we have.

Since 2021, Dream Bigger Philippines has run a training and mentorship program (accelerator) for local entrepreneurs. Small groups. Early-stage founders. Maximum twelve per cohort.

We learned a lot. Here is the honest version.

Talent is not the problem. Philippine founders are among the most creative, resourceful, and deeply motivated people I have ever worked with.  

But here is what five years has taught me: the path to entrepreneurship in the Philippines is harder than it needs to be. Not because of the people but because of the infrastructure around them.

The ecosystem is still being built. There are not yet enough visible exemplars to show the next generation what is possible at home. Entrepreneurship is rarely presented as a first-choice path. For many graduates, a stable corporate job is the more visible and rational option. That is not a criticism. That is a systems problem worth solving.

Capital is available both locally and globally. But what the Philippine ecosystem needs most right now is not just more money. It is more patient, creative capital that understands the local context and is willing to measure success differently. The metrics and models that work in San Francisco do not always translate to Cebu or Davao. The opportunity here is real and significant. But it requires investors and founders alike to build new frameworks, not import old ones.

That is what we aim to do.

Earlier this month, Dream Bigger Philippines quietly launched a paid membership platform open to both idea-stage and early-stage founders. Members get access to community, mentorship, content, and hands-on support to make entrepreneurship possible, not just aspirational.  

The goal: build a stronger pipeline of Filipino entrepreneurs with a redemptive imagination, a vision for scale, and a clear path to sustainability. When members are ready to raise, we add support for fundraising readiness including connecting them to investors from our global network who believe profit and purpose are not in conflict. And by building a platform that sustains itself, we can keep playing the long game of supporting the ecosystem for generations to come.

It’s too early to know if this model will work. But we’re choosing to build in public which means you’ll hear about the wins and the failures here first.

The Philippines has everything it needs to become one of the most dynamic entrepreneurial ecosystems in Asia. The talent is there. The hunger is there. The infrastructure is still being built, which means there is everything to create.

To learn more visit dreambigger.ph or email [email protected]

Last night I had dinner in Kirkland with someone I'm proud to call a friend: Dexter Ligot-Gordon, Co-Founder and CEO of Swarm.

I affectionately consider Dexter the ultimate “kuya” of the Philippine startup scene.

He left a six-figure salary at the City of San Francisco where he designed the city's Workforce Development Strategic Plan to co-found Kalibrr, the first Philippine startup accepted into Y Combinator. Now with Swarm, he's tackling the next frontier: getting enterprises starting in the Philippines to actually deploy AI at scale, not just pilot it to death.

His finding from the first-ever Philippine AI Adoption Report: 92% of Philippine organizations are using AI but most are stuck. Individual adoption is not organizational adoption. Buying ChatGPT licenses is not an AI strategy.

Swarm builds the infrastructure that makes AI real — embedded in existing systems, auditable, and actually connected to the workflows that drive revenue.

If you’re leading a company and wondering why your AI pilots aren't sticking, Dexter's work is worth your attention. And if you are a US company looking to understand the Philippine tech landscape before building a team there, his Philippine AI Report is required reading.

Learn more at swarm.work

One of Dream Bigger's core values is Wholeness, which we define as “becoming healthy in mind, body, spirit and relationships.” This isn't just a framework. It's something we commit to train and practice imperfectly, each day.

My husband Joe is our Chief Sales Officer at Dream Bigger Squad, a provider of Philippine-based B2B sales teams for US companies. We build together, which is a gift and a minefield.

I'm a recovering workaholic. I love what I do and I can talk about it at all hours of the day and night. If I'm not intentional, work crowds out everything else including the person I'm building this life with.

We have a commitment: Friday nights are date nights. No work talk. Just dinner, connection, and conversation that has nothing to do with clients or pipeline.

It sounds small but it makes all the difference. 

The question for you this week: What is one rhythm that protects a relationship that matters?

Reply and tell me. I read every response.

How Might We? is a community newsletter.

If you are building something in the Philippines, running an experiment worth talking about, or know a founder who deserves a spotlight, I’d love to know. Just reply to this email. The best ideas in this newsletter will come from the people reading it.

How might we build this together?

How Might We? is published every other Friday. To share this with someone building, hiring, investing in, or dreaming bigger for the Philippines — forward this email.