Sunil Hamlet is the solo founder of Hamlet, a startup that uses LLMs to make local government meetings and decisions easy to understand. He previously founded Scripted (a freelance writing marketplace backed by Crosslink Capital and Red Point Ventures), was an early employee at GoodRx (around employee 200, pre-IPO), and was part of the group that purchased and revived the San Francisco magazine The Bold Italic after Gannett shuttered it.
The episode traces Sunil’s path from running for city council in Orinda, California, to discovering that local government is almost intentionally opaque — and building a company around fixing that. It covers his philosophy on solo founding, original insights, editorial voice, team-building, pricing, and the surprising discovery that real estate and data center developers would become Hamlet’s core customers.
The problem: local government is a $2 trillion black box
Two trillion dollars of GDP flows through local government every year in the US, yet it is almost entirely untouched by technology.
Local government affects people’s daily lives more than federal or state politics — zoning, housing, data center siting, retail development — but it is extremely difficult for ordinary residents to follow.
Since COVID, most city council chambers started recording meetings, creating a data source that didn’t exist before. Combined with modern LLMs, this made a product like Hamlet technically feasible for the first time.
What Sunil discovered running for Orinda city council
Sunil ran for city council in Orinda, California (population ~19,000) while working at GoodRx, motivated by a desire to get involved in his community after moving there with young kids.
He learned that even in a small, non-partisan city, you need to raise at least $20,000 to win a council race, and candidates tend to fall into two unappealing categories: those with higher political ambitions and retirees trying to freeze the city in the past.
Public comment is largely ineffective. Meetings are poorly attended. A small group of “local voices” dominates comment periods but is not representative of the city.
90%+ of council votes are pre-decided before the meeting starts. Despite the Brown Act prohibiting private coordination among officials, information flows through daisy chains. Meetings function largely as rubber stamps. The real value of watching them is spotting contradictions and gauging genuine sentiment.
The newsletter MVP and the pivot to enterprise
After his campaign, Sunil started a newsletter summarizing Orinda city council activity and quickly gained hundreds of subscribers, confirming that people silently care about local government.
He expanded to a few more cities with similar results. The original plan was a consumer product for residents.
Around 7–8 months in, real estate developers reached out asking if Hamlet could help them track planning commission decisions and housing requirements in California. Then a data center developer came. These inbounds revealed a much clearer business opportunity.
Hamlet now focuses on three customer segments: residents, private companies (real estate developers, data center developers, retailers), and governments. Sunil is intentionally prioritizing private companies for now because that’s where the venture-scale business is, but he plans to serve all three eventually.
Why Sunil solo-founded — and his case for it
“No one’s going to care about this problem as much as me.” Sunil tried to find a co-founder but concluded that public meetings are too niche to attract one. He sees solo founding as essential for a problem this specific and unglamorous.
He did not feel ready to solo-found with his first company (Scripted). He needed the accumulated experience — including lessons from GoodRx and The Bold Italic — to have the confidence.
The bull case: Freedom to decide what to work on every morning. No need to wait for a co-founder to keep up. Ability to optimize for extraordinary outcomes rather than consensus-driven average ones. “When there’s consensus, there’s an average outcome.”
The bear case: You can feel resentful toward your team for not caring as much as you do. That psychology has to be actively managed through direct communication with leadership. There’s no one to gut-check your strong point of view, which makes it easier to fracture the team if you’re not careful.
Sunil’s approach: when resentment builds, he writes it down, then brings the list to his leadership team for an honest back-and-forth. He emphasizes that maturity and communication are essential.
Original insight as the non-negotiable
Sunil’s rule: “If you don’t have an original insight, don’t work on it.” He doesn’t mean you must be the only person in the world working on something — he means you must have a perspective on the industry or problem that no one else has.
He sees founders in every era chasing trends (freelance economy, crypto, AI, GLP-1s) with no original insight, and argues that vanishingly few of them make it. You cannot replicate the feeling of having something you can work on for 10 years.
Building the team as a solo founder
Sunil’s initial team came from GoodRx, but he largely turned them over once the business shifted away from consumer. He then hired a crew from Pivotal Labs, recruited by Mike, a former Nextdoor engineer of 6 years who became head of engineering and brought both technical skills and domain context.
Hamlet is currently 11 people, 6 engineers — intentionally lean.
Contract-to-hire is Sunil’s default policy for technical hires. He contracts for a few months to evaluate working style before extending offers. He compares it to a “slow dating process” and notes that even Google did this in its early days. Some early contractors were part-time, one was fully dedicated.
For non-engineering roles, he hired people with marketing, product, and ops backgrounds. Lindsay, who previously helped in an ops capacity, now runs customer success.
Using advisors aggressively
Because Sunil owns more of the company as a solo founder, he is more willing to give advisor equity to accelerate learning across his three customer segments.
His approach: intensity upfront. He front-loads the first 6 months — daily texts, intro requests, constant interaction — to extract as much knowledge and as many connections as possible before the relationship naturally settles.
Example: An advisor in real estate development made 25 introductions to top developers in the first 30 days. Sunil converted one into a customer, but the advisor remains someone he can call anytime because the rapport was established early.
He explicitly contrasts this with the common structure of “an hour a month” meetings, which he says doesn’t work for him.
Pricing and selling to unfamiliar customers
Sunil admits he’s still figuring out pricing — he gives himself a “C-minus, D-plus” on it. The product is subscription-based, priced on the number of cities a customer subscribes to, because meetings happen continuously across the country.
Advisors help him understand the customer landscape. He also attends industry conferences like the International Builders Show and Blueprint (real estate + tech), and went to a data center conference in Honolulu with 6,000 attendees.
His conference strategy: at minimum, ask a great question in a crowded session — something simple but deeply insightful that makes people remember you and approach you afterward. He’s also starting to offer free original research data to conference organizers as a value-add and conversation starter.
He’s interested in industry trade groups and associations as distribution channels: give a few members free access and let the value spread “like a contagion” through the group.
He notes that niche podcasts can be surprisingly effective for certain businesses — a friend’s podcast gets only ~100 listeners per episode but they’re extremely high-value potential customers.
Editorial voice: why authenticity matters
When Sunil revived The Bold Italic, he initially tried to replicate its existing editorial voice and audience. It felt inauthentic and didn’t work.
The breakthrough came when he wrote “This Is Your Life in Silicon Valley” — a satirical piece about the tech rat race, influenced by books like Bonfire of the Vanities and writers like Bukowski. It generated millions of views, trended on Twitter, led to an interview with Kara Swisher, and nearly led to a book deal. Five subsequent pieces all generated hundreds of thousands of views and led to a podcast that reached the top 200 in the US.
Lesson: You cannot replicate editorial voice. When you lean into your own point of view, it resonates. People are afraid of having strong worldviews because they fear social media backlash, but having a point of view is essential.
For Hamlet’s editorial voice: Sunil wants it to be the most authoritative source on local government knowledge in America. He focuses on longer-form, deeper research pieces that explain the “why” behind local government decisions, not flashy data visualizations. “People feel smarter and want to be involved with companies that increase their understanding.”
How to get involved in local government
Sunil’s minimum recommendation: vote in city council elections. Only about 20% of people vote in down-ballot local elections.
Better: join a city commission (Parks and Rec, Planning, etc.). These are appointed positions — you fill out a one-page form, interview with the city council, and commit ~3–4 hours per month. It’s a low-barrier way to actually influence your community.
He personally served on a commission in Orinda and enjoyed the experience.
The throughline: easy to understand, hard to build
Sunil gravitates toward businesses that are easy to explain but hard to build because they require deep contextual knowledge. GoodRx (make prescription drugs cheaper) and Hamlet (make local government understandable) both fit this pattern.
He compares it to watching Roger Federer play tennis — it looks easy, but requires enormous context and practice. A fresh-out-of-college founder could use Claude Code to process meetings, but wouldn’t understand the difference between a strong mayor system and a council-manager system, or the political dynamics that make local government opaque.
He believes Hamlet is an obvious idea that’s going to work: “I just have to navigate what the right product is that’s going to launch it to the next level, but I know it’s going to work.”
