Two years ago, I never intended to write a newsletter. I simply needed a place to think. What began as a private exercise to process the changes, losses, and lessons unfolding in my life slowly turned into something else. As I wrote, people found their way in. They shared the posts, forwarded them to founders, sent them to students, and brought them into conversations I once never expected to join. Without planning it or marketing it or imagining an audience, a community formed. Today, more than 2000 people read Through the VC Looking Glass, and I am still trying to understand how something so unplanned became something meaningful.

When I started writing, my goal was simple. I wanted clarity. Life was changing quickly, and the pace of everything around me made it difficult to process my own thoughts. Writing gave me a way to slow things down. It helped me see what I believed, what I feared, what I hoped for, and what I still needed to learn. It became a record of an important transition in my life and a way to understand myself more fully.

I also wanted a place to document what I was learning. Every conversation with a founder, every meeting with a corporate partner, and every late night with friends who helped me rebuild felt meaningful. I wanted to remember the people I met and the lessons they shared. I wanted to capture the early ideas that would eventually shape my manifesto and mandate, and understand how they were forming in real time.

In the beginning, the writing was quiet and unstructured. No schedule. No pressure. Just a private place to think and recognize the patterns in my decisions. It helped me stay honest with myself. It helped me separate signal from noise.

Through the VC Looking Glass began as a personal exercise. It was a place for reflection, memory, and defining the principles that guide my work. In those early days, that purpose was enough.

As I continued to write, something unexpected happened. People began to find the newsletter and share it with others. Founders passed it along to their teams. Students used it to understand venture, real estate, and the practice of building. Partners in Japan and across the United States read it to follow the ideas we were exploring together. The writing reached communities that reflected every part of my life.

The growth came without marketing. It came from conversations, forwarded emails, and readers who felt connected to the ideas. Each new subscriber arrived through someone’s trust, and that trust created a steady and meaningful expansion.

Over time, the newsletter grew into a community of 2005 readers. The number matters less than the mix of voices within it: early-stage founders, LPs, operators, students, friends from the Filipino community, leaders from the USF network, and partners in Japan who help me bridge two business cultures. All of them chose to stay.

The reach surprised me, and the impact surprised me even more. Writing allowed me to speak with clarity about ideas I was still forming. The responses and reflections from readers sharpened those ideas. The newsletter became a living dialogue between my own growth and the people who cared enough to engage with it.

Through the VC Looking Glass shifted from a private space to a shared place where ideas could move, connect, and evolve.

Writing changed the way I think. It pushed me to articulate ideas that once lived only as instincts. When I put them on the page, they gained structure. Patterns appeared. Principles surfaced. Assumptions became clear. Writing turned intuition into something I could examine and improve.

It also taught me how to listen. Every founder conversation, board discussion, corporate meeting, or quiet moment carried a lesson. Capturing those lessons made me pay closer attention. I became more aware of the details that reveal conviction, strategy, or character. Writing trained me to observe with intention.

Writing shaped the way I make decisions. The practice clarified what I value in a founder, a partnership, or a market cycle. I began to see the difference between noise and signal, speed and progress, activity and purpose. The process helped me recognize when I was acting from fear and when I was acting from conviction.

I love it when someone replies to a post or shares it with another person. When I meet someone who has read something I wrote, I feel a sense of closeness. There is a familiarity that forms because they have already seen a piece of how I think. During presentations or public moments, I can sometimes sense that something I wrote helped someone understand a point or make a decision. I enjoy those moments. They remind me that these shared thoughts and words have purpose for people I may never meet directly.

The practice of writing also created accountability. When you write publicly, even for a small community, your thinking becomes visible. You grow into your own words. You refine them. You carry them into your decisions. That accountability strengthened my judgment and the responsibility I feel as an investor, partner, and leader.

Most of all, writing taught me that growth requires reflection. The world around us moves quickly. Markets shift. Teams evolve. Opportunities appear and disappear. Reflection gives meaning to those experiences. Writing gave me space to understand the lessons, appreciate the people who shaped them, and recognize the beliefs that continue to guide my work.

As the newsletter grew, several readers encouraged me to introduce a paid tier. They felt the writing had value and believed people would support it. Their confidence meant a great deal to me, and I spent time thinking about the idea.

In that process, I gained clarity. Through the VC Looking Glass was never created as a product. It began as a place for clarity, reflection, and understanding. It grew into a community because people felt connected to the ideas and the honesty behind them. That connection shapes the way I write and the way I show up for others.

A paywall would reduce access for students, new founders, and people who are still finding their path. It would limit the reach of the ideas that brought readers here. It would shift the focus away from clarity and toward content production, which does not align with the purpose of this writing.

I want everyone who finds value in this writing to read it freely. I want the ideas to move without barriers. I want the next student, founder, operator, or partner to have the same access as someone with more experience or resources. Free access supports the spirit of shared learning that shaped this community from the beginning.

Through the VC Looking Glass will remain free.

Keeping the newsletter free is important to me, but it comes with real costs. The tools I use require a subscription. Beehiiv costs sixty-nine dollars each month. There are also the quiet costs of time, energy, and focus required to write while managing venture work, founder support, USF responsibilities, partnerships across borders, and my life as a parent.

I write because it brings clarity and connection. I write because I believe in sharing lessons openly. Still, sustaining the newsletter requires resources, and I want to be transparent about that.

As we enter Year Three, I want to invest more intentionally in this craft. I want to continue improving the substance of the writing and maintain a consistent space where these ideas can grow.

And eventhough it is free, from time time I am going to promote some of space on my newsletter, this month we are partnering with Ad Managed by ROKU.

Over the next year, Roku predicts that 100% of the streaming audience will see ads. For growth marketers in 2026, CTV will remain an important “safe space” as AI creates widespread disruption in the search and social channels. Plus, easier access to self-serve CTV ad buying tools and targeting options will lead to a surge in locally-targeted streaming campaigns.

Read our guide to find out why growth marketers should make sure CTV is part of their 2026 media mix.

Learn more.

To keep the newsletter free and open for everyone, I am introducing a Supporter Tier. It is entirely voluntary. It does not unlock exclusive posts or a separate version of the newsletter. It simply gives readers who want to contribute a way to help sustain the work.

I think about it the way people think about NPR or KQED, but without the federal funding, or at least the funding they once received. These stations stayed accessible because a portion of their audience chose to support them. Without that support, many programs that shaped entire generations would have disappeared into a stack of VHS tapes in a school library. Shows like Reading Rainbow or The Voyage of the Mimi reached classrooms because people believed in them and wanted them to continue. The content stayed open because the community carried it.

I want this newsletter to follow a similar spirit. Through the VC Looking Glass was built on openness, generosity, and shared learning. The Supporter Tier allows that spirit to continue without adding barriers.

For those who choose to support, I will occasionally share early thoughts, behind-the-scenes notes, or ideas that shape future essays. Supporters will also receive a small acknowledgment in a future post as recognition of their role in sustaining this work. The main body of the newsletter remains open to everyone.

If the writing has brought you clarity, connection, or perspective, you now have a way to support it. There is no pressure. The Supporter Tier is simply an option for those who feel aligned with the work and want to take a small step to help it continue.

Whether you join it or continue reading for free, I am grateful you are here.

As the newsletter enters its third year, I feel a growing sense of clarity about the direction ahead. The writing will continue to explore the intersection of venture, real estate, AI, and the lessons that guide how we build. But the next chapter will also reflect the shifts happening within my own work.

Over the past year, I have had conversations with several of my partners about expanding what we do. We feel a strong pull toward builder mode, even as we continue to grow the venture fund. Ideas that began as reflections inside this newsletter are becoming real products, pilots, and partnerships. The line between investor and builder is becoming more fluid, and that evolution deserves to be documented with the same honesty that has shaped this writing from the start.

We have received meaningful invitations to step deeper into creation. These opportunities give us energy and a renewed sense of purpose. As a team, we are excited about the possibilities that 2026 may bring and the new paths that are beginning to open.

Year Three will reflect this movement. The writing will go deeper into the ideas that guide us. It will follow the lessons from cross-border partnerships, the experiments we pursue, the founders who shape our thinking, and the philosophies that influence how we build. It will also continue to explore the personal side of growth: the moments of uncertainty, the clarity that follows, and the principles that are still taking form.

The intention remains the same. I want this space to help people think more clearly, act with conviction, and understand the world with greater depth. I want readers to follow not only what we invest in but also what we create, who we partner with, and how we evolve.

Year Three is about depth, honesty, and forward movement.

Thank you for being part of this community. When I began writing, I simply needed a place to think. I did not imagine that those early reflections would turn into conversations with founders, students, operators, and partners around the world. I did not imagine they would help me clarify decisions, build relationships, or understand myself more fully. The fact that you continue to read, respond, and share these thoughts gives this work a purpose I never expected.

I have made many mistakes, and I am sure more will come. I believe I make more good decisions than bad, even if the balance does not always feel that way in the moment. The mistakes are part of the work. The lessons are part of the journey. We are here to test our limits and search for a deeper sense of truth in the decisions we make and in the people we become.

As we enter Year Three, I feel grateful for every person who has taken a moment to read a post, reply with a perspective, or forward something I wrote to someone else. Those gestures remind me that these ideas carry meaning beyond the page. They remind me that I am writing not into a void but into a community that is growing and thinking with me.

Through the VC Looking Glass will remain free. The Supporter Tier exists only for those who want to help sustain the work. The heart of the newsletter stays open to everyone.

Thank you for reading. Thank you for engaging. Thank you for sharing a part of your own journey with mine.

Here is to the next chapter, the next lesson, and the next moment of clarity.

Year Three begins now.

xoxo,

Max

P.S. Stay with me on this journey. 

Disclaimer

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If nothing else, thanks for reading.

Through the VC Looking Glass will always remain free.
If you want to support the work, you can join the Supporter Tier here.