After nearly a decade spent managing narrative on behalf of the most prominent venture-backed companies of their generation, in 2025 I left the corporate world behind to build something of my own.
My core thesis was that narrative is capital.
The zeitgeist was starting to coalesce around the idea that narrative is as important to creating value in venture-backed companies as product innovation or operational excellence. The most talented market participants, whether at the founder or investor level, increasingly share a common core competency: the ability to build consensus out of words.
The function I spent my career in, typically labeled on the org chart as “communications,” was starting to occupy a space much more nuanced than public relations, but the current set of practitioners were too entrenched in their traditional tradecraft to see the bigger picture of how their work could create the kind of value that can be measured on a balance sheet.
I had never really fit into the neat boxes of a comms IC role, and saw an opportunity to take advantage of this market shift.
I founded Dimes Square Advisory, paying homage to a place that was more narrative than neighborhood while reappropriating the label of NYC’s ascendant political class for my own deeply capitalistic purposes.
My goal was to serve as an angel advisor to early-stage founders in fintech and crypto, accepting a small cash retainer and equity stake in return for being their ultimate generalist.
Over the course of a year, and after speaking to more than a hundred founders over thousands of hours of Zoom calls and coffee chats, I realized that while I can generate interest in my advice with the right people, it’s a hard thing for me to price.
I started my career in politics, and when I see a mission or leader that’s irresistible to be close to, it goes against every fiber of my being to charge a toll for ideas that flow so freely in my head. After all, the only way to prove that my ideas are good is to share them. Once you share one idea, there are immediate diminishing returns to the value of the next idea.
The natural solution to my monetization challenge was to spend time building an audience on X. After all, I’d helped plenty of founders, investors, and political candidates successfully do this throughout my career, but for some reason it didn’t seem right yet for me. I thought my ideas were good, but I didn’t have an instinct for how to perform in front of an audience without a clear purpose.
Instead, I chose the riskier path. If I wanted to really test that my ideas could make money, I could do so by putting my own capital at stake.
DSA became the structure for that: not a services practice billing for advice, but a way to generate ideas and test them with my own money.
For angel advisory, this meant that instead of cold emailing every YC fintech from the past four batches, I'd find the companies I'd actually want to invest in and do anything possible to get on the cap table.
It also meant adding public markets to my toolkit, an arena I can participate in immediately, with a much tighter feedback loop on whether my ideas are right.
The craft is its own discipline, event-driven, macro, value, but it sharpens the same first-principles read of technology rather than competing with it.
And the opportunity is real, because the institutions that price public technology companies, the sell-side analysts and the buy-side PMs, mostly aren't built to understand technology the way someone inside it does. That gap throws off returns for anyone who can see what they're missing.
I don't know yet what DSA will become. The reasoning behind the bets lives on the ideas page, and if you're reading this, I've let you see the process in real time, before it's ready for the world.