Writing From the Middle
I didn't set out to become an investor in any formal sense. But I grew up around people building things.
On the San Francisco Peninsula, I was close enough to Sand Hill Road to absorb its mythology, but far enough away to never mistake proximity for belonging. Or at least not belonging to the version of the story that gets repeated most often.
I was around the work before I had language for it. Just not the billion-dollar version.
The business lessons came from my mother. She was the person companies called when things were breaking. A contract CFO and controller brought into businesses under strain or public stress to help turn them around.
On the side, she built businesses. A family distribution company. Real estate development. Her own investing. She was an operator and an allocator at once, long before I had words for either.
I didn't understand all of that at the time. I just watched how ideas became real, and how broken things got fixed, through decisions, risk, and follow-through.
What stayed with me was that the right judgment, at the right moment, could move something forward, or save something, that otherwise might not have made it. Ownership or control did not really come into my thought process until much later. I was fascinated with challenges and solutions.
The access came from another side of the family. My father's sister married into tech before tech was quite tech yet. They moved to Atherton, and through her I had a view into a world I would not have otherwise seen.
That access does not matter in the way people might think it does. It does not mean I can text a major VC and get a fund funded. It does not make a person deserving of confidence or capital on its own.
But it did leave a real impression. I also understand more than I used to that relationships are not superficial in this business. They are a significant part of the work. Deals get done through trust, context, and access, and the founders you invest in deserve someone who can help open the right doors when it matters. A lot more on that later.
From around 1997, when I was in middle school, the venture world became an actual set of people I could meet, watch, and listen to. I was a kid at the edge of those rooms, with no claim to be in them, paying close attention.
That is probably where I first started noticing some of the things I still think about now. How some investors add clarity and others add noise. How judgment matters more than intelligence. How much of the mythology is performance, and how much of it is real.
My experience since has been in building companies. From the start, I've been interested in capital itself. How to raise it, and how it shapes behavior, incentives, power, and momentum.
Right now, I'm building two companies while laying the groundwork for an investment fund. Those efforts are happening in parallel, and they inform each other every day.
I'm writing this because the transition from operator to investor is rarely talked about honestly, especially while it is happening. There is a lot of pressure to project doneness before it is real. I have found that my openness to input, my honesty about the stage I'm in, and an interest in learning from mistakes have brought me to some incredible relationships and opportunities.
Most writing about investing comes from one of two places. It is written in hindsight, after outcomes are known, or it is written performatively, projecting certainty before it has been earned. I’m somewhere in between.
Still in the weeds. Still learning which parts of the operator in me are useful, and which parts need to change.
Building companies teaches you to push, solve, and stay close to the work. Investing asks for something different. It asks you to see clearly without needing to control everything yourself.
That is what I’m trying to pay attention to now: what gives people the confidence to believe it should be built at all.
The things I first half-understood at the edge of those rooms, I am now living from the inside. Maybe that is the point.
I'm also realizing that becoming an investor is not about abandoning the operator in me. It is about refining it. Taking what works, letting go of what doesn't, and being honest about the cost of both.
This will not be a newsletter about fund mechanics or hot deals. It also will not be a personal journal. Though at times, it may borrow from both.
It is a working document. A place to think in public about building companies, building capital, and becoming someone I would actually want on a cap table.
That is the place I know how to write from right now: the middle.