Two trillion dollars of GDP flows through local government every year. 90%+ of city council votes are pre-decided before the meeting starts. And almost no founder will touch the market. Sunil is the rare exception. He ran for city council in Orinda, California, lost, and walked away with a newsletter for residents and an obsession with how opaque local government actually is. That newsletter became Hamlet — the civic AI making local government meetings legible to residents, real estate developers, and the cities themselves. This episode is the most concrete civic-engagement segment we've recorded on the show, and incidentally a clean founder thesis on how to spot a market everyone else is ignoring.

Topics covered:

$2 trillion of GDP runs through local government — and almost no founder will touch it
90%+ of city council votes are pre-decided before the meeting starts
Why "public comment is largely ineffective" and why the "local vocals" aren't representative
Most city councils are rubber-stamp organizations
Running for Orinda city council — and the $20K-minimum reality of nominally non-partisan local elections
The civic-engagement on-ramp — join a commission as the lowest-friction way to start participating
The newsletter-MVP-to-Hamlet arc — how a personal newsletter for residents became a civic AI company
Easy-to-explain businesses and why they require context, knowledge, and subject-matter expertise (the Federer analogy)
"If you don't have an original insight, just don't work on it" — Sunil's hardest founder filter
"No one's going to care about this problem as much as me" — niche obsession as the only test that matters
The Bold Italic acquisition, "This Is Your Life in Silicon Valley," and why you can't copy editorial voice
Front-loaded advisor relationships as a substitute for the co-founder dynamic
Pricing humility — "C-minus, D-plus" — and what to do about it
Bear case for solo founding — resentment, no gut-check, easier to fracture
The "let things simmer" leadership rule
Bull case for solo founding — "consensus produces average outcomes"

Guest: Sunil — Founder and CEO, Hamlet. Previously co-founder of Scripted (Crosslink, Redpoint), EIR at Foundation Capital, executive at GoodRx through its IPO. Ran for Orinda city council. Crosslink-backed twice across 15 years and 2 companies.
Host: Julian Weisser — Founder/CEO of Solo Founders and Co-Founder/CEO of On Deck/ODF.

The Secret $2 Trillion Market Founders Are Ignoring | Sunil Rajaraman, Hamlet