In short
Hamlet’s mission is to make local government easy to understand by summarizing city council/commission meetings and using LLMs to explain what residents actually need to know. Sunil argues founders ignore a “$2 trillion” local-economy market because local politics is opaque, meetings are largely ineffective, and decisions are often made before public sessions.
Guest
Sunil Rajaraman. Background: wrote/edited at local publications (high school editor-in-chief; revived Bold Italic after Gannett shuttered it; sold it to Medium). Tech/startups: Scripted (2008–2011 era; built a screenwriter community product; pivoted to a freelance-writer marketplace; backed by Crossland Capital and Redpoint Ventures; “many millions” revenue; first customer Levi’s). Later: employee at GoodRx (joined as employee in late stage). Angel investing.
Key claims
Local politics drives day-to-day life more than federal/state. Public comment is “largely ineffective”; “local vocals” aren’t representative. Most councils act as rubber stamps; council members vote in sync. “Easy to explain” businesses still require deep contextual expertise.
Notable examples
Orinda, CA city council run; empty chambers; Brown Act constraints; developer inbound requests (real estate, data center). Hamlet newsletter MVP with hundreds of subscribers; developer customers asked for planning commission/housing insights.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Case for Solo Founding
0:45 to 1:30
Exploring the unique perspective and challenges of solo founders.
“the kid in high school who was editor-in-chief of the paper, editor-in-chief of the yearbook.”
Path to Local Government Engagement
1:30 to 3:00
Discussing the transition from media to engaging with local governance.
“And that's when I discovered the problem that Hamlet's trying to solve.”
The Insights Behind Hamlet's Creation
3:00 to 4:30
Understanding the motivations behind creating Hamlet and its relevance.
“starting hamlet i feel like it's gonna be a therapy session so uh well i uh my first company was called Scripted.”
The Journey of Scripted
4:30 to 8:00
Detailing the founding and evolution of the Scripted company.
“That business was backed by Crossland Capital, Redpoint Ventures, and some others.”
The Importance of Community Understanding
8:00 to 10:00
Examining the significance of understanding local community dynamics.
“who might be more enamored by building a foundation model or something like that.”
Problems in Local Government Meetings
10:00 to 12:00
Discussing inefficiencies in local government meetings and public comments.
“of Berkeley and Lafayette and Walnut Creek.”
Building Hamlet's MVP
12:00 to 14:01
Exploring the initial steps taken to create Hamlet and engage the community.
“that you end up working to solve with Hamlet?”
Starting a Local Newsletter Business
14:01 to 15:10
Learn how a newsletter about local city council meetings evolved into a broader business.
“You did something pretty interesting, I think at least, which was that you started with this newsletter for your town.”
Navigating Business Focus and Opportunities
15:10 to 17:43
Explore how founders can adapt their business focus based on emerging opportunities and customer feedback.
“for the business was to start with consumers however about seven or eight months into the business, a real estate developer reached out and said, we see what you're doing with city council summaries.”
Leveraging Advisors as a Solo Founder
17:43 to 21:54
Understand the importance of advisors for solo founders and how to effectively collaborate with them.
“listening who have similar situations arise.”
Show all 25 chapters
The Unique Challenges of Solo Founding
21:54 to 24:03
Discover the differences in building a company as a solo founder versus with co-founders.
“What are some things that you feel are fundamentally different about building a company when you are solo versus when you have co-founders?”
Developing an Authentic Editorial Voice
24:03 to 27:38
Learn how to cultivate a unique editorial voice that resonates with your audience.
“I admired it from afar and had a very, very unique editorial voice and point of view.”
Developing Your Editorial Voice
28:20 to 29:10
Discover how founders can cultivate their unique editorial voice amidst industry noise.
“How do they come up with, you know, the thing that will resonate with their audience?”
Shifting from Safe to Bold
29:10 to 30:00
Explore the importance of taking risks in expressing one's viewpoint as a founder.
“They're afraid of getting lambasted on social media, things like that.”
Reflections on Editorial Freedom
30:00 to 31:10
Hear insights on the liberating experience of writing authentically and the impact it has on success.
“of your reflections on this is your life in Silicon Valley now, because I think that if people were to read it, we'll link to it.”
The Challenges of Originality in Business
31:10 to 33:20
Learn about the necessity of original insights in entrepreneurial ventures to succeed.
“Within that, I'm navigating as a founder what the right product is going to be that's going to launch it to the next level.”
Surprises in Local Governance
33:20 to 34:50
Understand the unexpected challenges in local governance and the need for community-focused leaders.
“I'm continually shocked that people don't always act in the best interest of their communities, which is like a sad realization to come to.”
Encouraging Local Engagement
34:50 to 36:40
Discover how individuals can engage in local governance and the importance of active participation.
“And I hope we need better people to run at the local level, in my opinion.”
Building a Team for Success
36:40 to 37:50
Explore insights on building a capable team that aligns with your business vision.
“For the down-ballot elections, only like 20 % of people vote on city council.”
Navigating Early Hiring
37:50 to 40:50
Learn the nuances of early-stage hiring and the importance of aligning team skills with business goals.
“I met someone who was an engineer at Nextdoor, Mike, who became our head of engineering and recruited a whole crew of pivotal engineers who now work with the company.”
Understanding Your Customer Base
40:50 to 42:00
Gain insights into the challenges of selling to unfamiliar customer segments and strategies for success.
“one person who was more or less dedicated uh to hamlet full-time it's it's been a mixed bag um But they all had very, very unique and good backgrounds.”
Navigating Early Startup Challenges
42:00 to 44:18
Learn about the importance of understanding your customer and pricing strategy in the early days of a startup.
“In your case, I don't think that you've ever sold to some of the people that you're selling to.”
Maximizing Conference Opportunities
44:18 to 47:51
Discover strategies for making the most out of attending industry conferences to build connections and learn.
“Some startups, it's a big distraction, especially the more sort of generalized the conference and maybe the earlier the startup.”
The Impact of Niche Media on Business
47:51 to 50:28
Explore how niche podcasts can effectively target specific audiences for marketing purposes.
“One thing I'm deeply interested in is the nature of our customer here is they are usually parts of industry trade groups, whatever.”
The Pros and Cons of Solo Founding
50:28 to 54:18
Discuss the psychological challenges and benefits of being a solo founder in the startup ecosystem.
“It can create an interesting psychology between you and the team that you have to really actively manage.”
Transcript
Automatic transcript. May contain errors.0:00Hamlet:No one's going to care about this problem as much as me. You don't see trendy founders go into public government meetings very often. If you don't have an original insight, don't work on it. Some people are ready to solo phone right away as their first thing. I needed the benefit of all that experience to have the confidence to solo phone. You just have to have a good support system. I am not the best at focus. I want it all. You have a stronger point of view as a solo founder, and there's nobody else there to gut check you. What is the case for solo founding?
0:54Hamlet:the kid in high school who was editor-in-chief of the paper, editor-in-chief of the yearbook. In college, I did the same thing. In grad school, I did the same thing. And then, yeah, and then, you know, I was part of a group that purchased the Bold Italic when it was shuttered by Gannett Publishing, and we revived it, ran it for a few years, and eventually sold it to Medium. But I've always kind of been at the edges of local and cared about local a lot and community a lot. But with Hamlet, it was my city council run that caused me to go all in because I'd just been teetering on the edge. You know what?
1:31Hamlet:Next logical step. Why not try to run for public office? And that's when I discovered the problem that Hamlet's trying to solve. I feel like they're almost intentionally opaque. And kind of the insight I had was so much of our day-to-day lives is influenced by local politics. Everybody's so worried about federal-level politics. Everybody's worried about state level. now we've got a you know scandal after another you know we've got a new governor you know i i don't know what's going on anymore but really what affects your day-to-day life more is local and that was the that was kind of the light bulb moment was seeing you have these empty council chambers and empty commission halls and the city the city's future is basically being decided here but it's all recorded so since covid uh most city council chambers started putting recording equipment in their city halls.
2:18Hamlet:And so it was the combination of that realization plus having LLMs available that made Hamlet the why now possible. And my motivation was all of this should be easy for residents to understand. They shouldn't have to attend a four or six hour meeting at the end of the work because that's the last thing that they want to do.
2:37Sunil Rajaraman:I think there's something really interesting about the story about how you ran for local office and we can get there. But I think it would be really useful for folks who are listening or watching for you to maybe just talk a little bit about kind of the things that you've done after the bold italic you've done some really interesting things um in tech and startups um and maybe just run through a little bit of like how you progress from one to the other and maybe we can start to like narrow in on how that progression kind of led you to starting hamlet i feel like it's gonna be a therapy session so uh well i uh my first company
3:10Hamlet:was called Scripted. And that was kind of around the 2011 timeframe. Really, I started working on it part-time in 2008 during the financial crisis. And I've always been at the intersection of writing and technology in some way, like content creation and tech. That is definitely a theme. What Scripted was trying to do, the first iteration of the business was we were trying to build a community of screenwriters. And we built this Google Documents-like product for screenwriters. And we thought, you know what? hey, if we build enough of a community, we can convince Hollywood producers to discover screenwriting talent from us.
3:47Hamlet:We built up the community with about 80 ,000 screenwriters, which is back in those days, 08, 09, 2010, not insignificant. What we realized, though, is Hollywood doesn't want more writers. They have a guild. They have all sorts of stuff going on. There's too many people trying to make it. then we thought maybe YouTube shorts are going to become scripted and all this stuff. But what actually ended up happening with that business is Levi's was our first customer. They reached out to us and said, hey, we've heard about you. You're that screenwriting community. Could you help us with ad copy for a project that we're working on?
4:27Hamlet:We don't have the time to wait for an agency. And then that turned into Scripted, which was a marketplace for businesses to hire freelance writers. That business was backed by Crossland Capital, Redpoint Ventures, and some others. And it grew to many millions of revenue. But I got back to it with Hamlet. And in between, I've done some investing and things like that. But I've always been at the intersection of some sort of community writing and tech. And that is a common theme, I would say. I know what to do. And I think there's a self-awareness that develops over time. where you know what your weaknesses are.
5:07And I know what I'm not good at.
5:10Hamlet:I know what I don't enjoy. And if you can really deeply examine that and have the self-awareness to do that, I think you're ready to be a solo founder. And I would not personally just, you know, it's a very subjective thing. Some people are ready to solo found right away as their first thing. I needed the benefit of all that experience to have the confidence to solo found because there's just a lot of lessons I needed to learn, good and bad along the way.
5:34Sunil Rajaraman:Would you say that there were things that you kind of were evaluating as you approached building Hamlet? Or did you feel like it was pretty clear to you that it would be a solo-founded company from the get-go?
5:48Hamlet:No one's going to care about this problem as much as me because it's such a niche problem. I really tried to force it and talk to a bunch of people and things like that. But good luck trying to find a co-founder who's into public meetings and is technology-oriented. It's sort of on the fringes of idea that you don't see trendy founders go into public government meetings very often.
6:16Sunil Rajaraman:Maybe we should talk about that, though, because it feels like, in a lot of ways, you've never built for trends. GoodRx wasn't really a trendy company, and it did quite well. Maybe you could talk a little bit about what you think about trends and trendy companies versus these other ones. You've done some angel investing as well. It feels like everybody obviously goes towards the things that are hot. Sometimes there's actually a reason that there's heat there. But there's so much to be found in these great companies. Hamlet is just such a great idea. It feels like it's going to help a lot of people.
6:51Sunil Rajaraman:Maybe just speak a little bit about that. I'd be curious to hear your talk.
6:54Hamlet:Yeah, I like problems that are easy to explain, not just for an outside audience, but it's a good way to remind yourself what you're working on. So for me, local government is very difficult to understand. And making it easier to understand actually turns out to be a good business. Why? Because real estate developers have to operate at the local level, data center developers, we all know that, retailers often look at hundreds of cities before they pick one, $2 trillion of GDP runs through local. It's such an obvious problem that technology hasn't touched. In the case of GoodRx, which I joined as employee 200, it was a late stage company by that point.
7:36Hamlet:But I like that it was easy to understand. Prescription drugs are expensive and there needs to be a way to make them cheaper for cash paying customers. And I've always gravitated toward companies that are easier to understand. And it's not because they're not capable of producing great technology, but it's just boring and often untouched by founders who might be more enamored by building a foundation model or something like that.
8:07Sunil Rajaraman:The easy-to-understand threshold is quite cool. Why do you think that so many of the easy-to-understand companies are so hard to actually come up with?
8:17Hamlet:I think they do require experience, knowledge, and some subject matter expertise. It's, for example, let's just take Hamlet. Let's just say somebody fresh out of college wanted to build this business. Could you get pretty far with Cloud Code right now and process meetings and things like that? Sure. but the knowledge of how all the interplay, the interaction works, what the difference is between a strong mayor system and a council manager system. There's so much contextual knowledge needed in a business that may appear simple. So it's like I was a tennis player in college and growing up and you watch Roger Federer play.
9:04Hamlet:He makes everything look so easy. And is that because it's great but he just it's it's it's it looks easy but it requires a lot of context and practice and that's the type of business hamlet is and many of these easy to explain businesses require that like
9:22Sunil Rajaraman:context and knowledge what uh when it comes to hamlet like i think that a lot of this you said was the story of you running for public office what was that like why did you decide to run for public office what where maybe for people who are listening what what were you doing like where were running for public office? What was the goal behind it?
9:39Hamlet:I was at GoodRx at the time. And, you know, God bless them. I was, it was, I was getting a little bit bored. I was, you know, kind of getting the itch to get involved in community, try something new. We had just moved to Orinda, California. And city of 19 ,000 people, if you're not familiar with Orinda, it's next door of Berkeley and Lafayette and Walnut Creek. So Berkeley and Walnut Creek are better known cities. But I just, you know, I have young kids, and so I never had a chance to really participate in community, yet I know it's really important. One of my friends was a co-founder of Nextdoor.
10:20Hamlet:I always admired him. I almost joined Nextdoor at one point in time. I saw that they were looking for candidates, and so I just showed up. I thought, hey, let me approach this from an entrepreneurial mindset. I walked into the city hall. I got the paperwork. I saw what the filing fee was. I walked around my neighborhood. I got like 20, 25 signatures, whatever the threshold was at the time. And I thought, okay, I'm doing it. And then you just start asking around and you learn about, okay, well, how do candidates win? How many votes do they need? And I think one of the most surprising things I learned is, so city councils typically are nonpartisan positions.
10:59Hamlet:but they raise money. And so in a community like Orinda, you have to raise$20 ,000 at minimum to win an election. And so even in a city like that, you've got special interests. And even though it's not partisan roles, I can tell you with certainty that some of those candidates are plugged into the political machine. And you get a couple of different types of people. You have people who have high political aspirations and want to advance and become a state senator or whatever someday. And then you have people who are retired and want to protect the city that they once knew from changing. And those aren't the people you necessarily want in office.
11:40Hamlet:And this is happening all over America all the time. But fixing that, like, you know, we have a mission, which is to make local government easy to understand, and we have a business. And so I think of it as those two things. But we'll always be guided by this mission of making local government easier to understand.
11:57Sunil Rajaraman:What were some of the other things you were learning about the problem that you end up working to solve with Hamlet?
12:03Hamlet:I learned that public comment is largely ineffective. Say more about what public comment is for people who are listening
12:13Sunil Rajaraman:and they don't know what it is.
12:14Hamlet:Typically in meetings, in city council planning commission meetings, you can submit a comment in advance of that meeting, have that comment read out loud. Alternatively, at the end of a meeting, they allow, or at various points during the meeting, speakers to come up to the dais and speak for three minutes in response to certain things. The meetings aren't well attended. And you have what's called local vocals, who are the two or three people who attend every meeting and comment at every meeting. I guarantee you they're not representative of the city. Very much not. Very much not. They also don't affect the decision-making of the city.
12:54Hamlet:what I learned was most decisions are made before the meeting. So what you see is you see consensus. And so like 90 plus percent of the time, the council members just vote in sync. And even though they're technically not supposed to meet before the meeting, there's workarounds for that. There's this thing called the Brown Act where you're legally not allowed to meet with two other public officials. You can't even go to a bar and like do that stuff. but they talk. There's a daisy chain of information that happens in all of these cities. But decisions are often made before meetings are even taking place.
13:36Hamlet:So the value in the meetings is to actually see where people contradict their positions and things like that, how much they listen to public and what real sentiment is. I just think most city councils are rubber stamp organizations and we need to fix that.
13:53Sunil Rajaraman:When you were getting started with this, because it feels like there are a lot of different ways you could get started with a business like Hamlet where it comes to understanding what's happening in these meetings. You did something pretty interesting, I think at least, which was that you started with this newsletter for your town. Can you say a little bit about what the MVP looked like and how you actually went through the process of starting with the most basic building block and then kind of going one step and sort of pulling the thread and getting further and further down it. Yeah.
14:25Hamlet:During my, or immediately after my run, rather, I committed to, you know, I met a bunch of people. I committed to keeping people in touch with, you know, what's happening with city council and all of that. And I immediately found myself with hundreds of subscribers to that because people silently care. They want to know, and they are intrigued by things like who's raising money from where what is our city doing they have opinions on private roads and so uh the content was like really really highly engaged with so i know people are out there they care um and uh that was yeah and then i had the insight that it's probably scales across many cities and so i started a couple more newsletters i was like yeah no they definitely care and so the original idea for the business was to start with consumers however about seven or eight months into the business, a real estate developer reached out and said, we see what you're doing with city council summaries.
15:21Hamlet:Could you instead do this to help me with understanding the planning commission and what people are doing with their housing building requirements in California? And then another real estate developer came, and then a data center developer came. Ultimately, though, I want to build out all three parts of the business. There's residents, private companies, and governments. all three could get value out of our products but i'm intentionally focusing on private companies
15:49Sunil Rajaraman:right now how do you think about that as a founder when you have sort of an initial intention for the product you build it a certain way and then you start to see things that maybe you hadn't expected or maybe you hadn't expected at that point start to happen so you built this thing that was more of a consumer oriented product and you started to see you know real estate developers come to you how do you sort of interpret that? How do you think about sort of when to focus, when to move the focus? I think it's something that people often try and figure out. When should they take that signal and sort of like maybe move away from the initial thing, even though in your case, you're going to be coming back and trying to serve all these folks eventually.
16:30Hamlet:Yeah, a moment of self-awareness, speaking of being a seasoned founder, I am not the best at focus. I want it all. and so yes, you have to keep the team adaptive, ready to go, etc. And I have a team of people who are good at the organization and the focus and keeping me pointed. But I'll say this, I actually don't think it's my job to remain focused. I need to see the full opportunity scope. Ultimately, it's not interesting to me to build a SaaS company that sells data to real estate developers. I'll just be completely honest. that's not, when you build a venture-backed business, like you're going for it.
17:12Hamlet:You want something real, real big. I don't want a prop tech company that sells data. A, that's just not interesting to me. B, that's not why my investors back me. And C, I just don't think that that's like a multi-billion dollar business. So I'm going for it all. And depending on the day I wake up,
17:30Sunil Rajaraman:I'll be focused on one thing or the other. You were kind of like only focused on the one thing, the consumer. And then you've had this thing pop up. As a founder, you have to sometimes decide where you're going to be allocating resources. So I'm curious how you navigated that then, because that might be something that's useful for people who are listening who have similar situations arise.
17:48Hamlet:Yeah, I think once we got our first two real estate developer customers, I had the team lock into that use case. And I thought, okay, well, we do have a finite amount of resources. Let's do a deep dive of this. these spurts of focus where you get to know what the product need is, what the industry need is, et cetera. I use, see, I'm pretty generous with advisors and having advisors who are expert at these different areas, residents, private companies, and governments on my advisory board because they can help me accumulate that knowledge a lot faster. And as a solo founder, because you own more of the company, I'm much more willing to give a little bit of advisor equity here and there if it's going to speed up my learning on all those areas.
18:38Hamlet:I absorb industry knowledge from advisors. When I go into these moments of focus, that's how I get up to speed as fast as possible.
18:46Sunil Rajaraman:I think it's one of those things where, generally speaking, if you have a couple of co-founders, you're already splitting the company two or three ways. It's usually less advisable to think about advisors. As you were saying, I'm curious if you could share a little bit more about how you approach working with advisors sort of what the right expectations solo founders should have when they're working with them. Because I think that if you look at some of the things that go really poorly, typically, with companies and with founders and sort of the things, the choices that they make, it's often with working with advisors where they feel like they didn't really get what they were hoping out of the relationship.
Read the full transcript
19:23Sunil Rajaraman:Oftentimes, it's way more equity than maybe some people would expect. It's more equity than maybe somebody would get if they invested a pretty significant amount of money in the company. So to the extent that you're comfortable sharing how you do this, I think it would be really useful for people because I think there is a good way to use advisors. But I think that generally speaking, the way people do it is probably flat out wrong.
19:46Hamlet:It's intensely upfront. I mean, that's the way I approach it, is with any relationship, there's momentum. And you lose that momentum with time. That's just the nature of every relationship with some exceptions, your partner, your kids, your dog, whatever it is. Most relationships have a period and then they atrophy unless you really, really actively maintain them. Advisors are no different. And so you just really have to have that intensity up front. Get as much knowledge as you can up front in that first six months. be top of mind, text, interact, and then you won't be disappointed. For me personally, structuring it like, oh, an hour a month, we'll do a meeting, that doesn't work for me.
20:40Hamlet:Sometimes it's just got to be more intense up front. Get everything that you can knowledge-wise, and then if the person continues to contribute after, wonderful.
20:49Sunil Rajaraman:Could you give an example? I think you've done this a bunch of times. Can you give you an example of sort of like what that looks like, more of the upfront type thing. It could be a composite. It doesn't need to be exact, you know, exact example of one case, but I think it would be really useful for people to even understand what upfront looks like. Yeah.
21:03Hamlet:I had an advisor to Hamlet, who was an expert in the real estate development space, make like 25 intros to top developers. And out of that, we converted one as a customer. But in addition to that, you know, I was every day pinging this advisor for an intro request, like for that first 30 days or whatever. And he came through every single time. And then when it got to be too much to handle, I processed it and whatever, and I converted one of the customers. And so it turns out that was good, but I mean, he's a great guy. And beyond that, I can call him any time I want now. I don't do it every day.
21:44Hamlet:I don't even do it every month. but because that rapport and that intensity and all of that was established up front, he'll answer when I call.
21:54Sunil Rajaraman:That's really cool. What are some things that you feel are fundamentally different about building a company when you are solo versus when you have co-founders? Maybe you can talk, some of that will be about team and things like that, but even before that, I'm curious what the differences are for you in your mind.
22:13Hamlet:no one is i say this with all due respect to my team and i wouldn't expect them to to say and i mentioned this comment earlier but no one knows or cares about the problem as much as you as a solo founder period like you can't you can't transfer that desire so to speak my team really cares and they love this problem otherwise they wouldn't wouldn't be working on it spending a ton of time working on it, but it's not the same. It's just not the same. A co-founder cares a lot, sure, but that could be good or bad. I'm torn on whether it's necessary. I personally don't think it's necessary for Hamlet that I need someone else who cares about the problem as much as me or is as deep in it.
23:03Hamlet:Fundraising is all on you. so as a solo founder you better be a good fundraiser and if you're not you better learn how to especially if you're going to be venture backed you just have to have a good support system I think that is so so critical and I don't just mean within the company I mean outside of the company I have a ton of friends who I can count on to call and work through problems and whether it's personally, professionally, things like that. I didn't have that support system as a co-founder previously. So even as a co-founder, you feel that loneliness a bit. And I did not have the relationships I had then that I do now.
23:49Hamlet:And so just be prepared to have a support system. Be prepared to fundraise and walk into it knowing that you're the only one who's going to care as much as you do. maybe in the world about the problem. San Francisco-based magazine for locals here, I admired it from afar and had a very, very unique editorial voice and point of view. For the first six to 12 months of it, I tried to maintain that same look and feel, but it felt inauthentic. The audience knew it, that it was kind of bullshit. What I discovered was I should just, you know what, I should just provide my own voice to it. So what ended up happening was the most successful piece ever written for it.
24:36Hamlet:I wrote it. It was an article about the life of Silicon Valley. I call it This Is Your Life in Silicon Valley. It was a satirical piece about just what the rat race is like in the tech community. I wrote it exactly 10 years ago, almost to the day, by the way, but generated millions of views. We were all of a sudden trending on Twitter. It led to all sorts of weird opportunities. I was interviewed by Kara Swisher. Almost led to a book deal. But then I was just like, you know what? Let's just stick with this. Let's just go with this. Five subsequent pieces all generated hundreds of thousands of views.
25:15Hamlet:And it led to a podcast, which I started with Yasha Kakis-Wolf, who was at the time the CMO of Mozilla. the podcast who we interviewed people like Adam Mosseri, the CEO of Instagram, the mayor of Oakland at the time, Libby Schaaf. We had Tony Hale from Arrested Development. It got as high as top 200 in the US. And so the lesson from that was you can't copy editorial voice, but when I actually just focused on, you know what, I'm going to do my own thing, it worked much, much better.
25:49Sunil Rajaraman:so you just cannot replicate voice you can't do it that's really interesting too because uh it kind of plays into this general theme that we talk a lot about which is um the best startups are very unique um you can't try and copy your way into a successful like a very successful sort of long-term startup it might be a good sort of short-term thing sort short-term cheat code or something way to get some views and maybe a narrow window but ultimately like the thing that's authentic to you is going to probably look or feel or sound very different and it's it's kind of like the editorial voice right so i'm curious um when you think about the editorial voice for what you're doing with hamlet like what is that like what what was it and how has it developed over time
26:34Hamlet:yeah yeah we're going to be the most authoritative company when it comes to knowledge of local government in America, period. And we've started publishing some research based on the data that we have about local government, which is very uniquely us. What I typically see for startups in this space, whether they're in some form of public data, is they publish these dumb maps or these like, oh, look at this. How cool is this? This little insight I had about whatever, it's small potatoes. It's not actually what people care about. It may be for a flash in time, content is so ephemeral, it may capture a little bit of attention.
27:15Hamlet:But I'm focused on longer form, deeper pieces that actually illustrate a deeper understanding of local government. People feel smarter and want to be involved with companies that increase their understanding, not just flash data at them. And we'll always commit to a deeper understanding. People want to know the why, not just the result.
27:38Sunil Rajaraman:If you're enjoying this conversation, then perhaps you're starting your own company. And if so, you should apply for the Solo Founders Program. I've spent the last seven years working with startups and founders who are figuring things out. And I'll tell you, the ones that make the most progress are the ones who make sure that they have relationships that can help them go the distance. The Solo Founders Program is about bringing 10 solo founders together so that they can build solo together versus building solo them. I'll work with you, we'll invest$100 ,000, and we'll make sure that you make the most progress that you possibly can in three months.
28:09Sunil Rajaraman:If that sounds interesting, you should learn more and apply it at solofounders.com slash program. I'm sure a lot of founders who are listening to this are trying to really figure out, like, how do they develop their own editorial voice? How do they come up with, you know, the thing that will resonate with their audience? You know, it seems like there is an iterative approach in a way, and then you've kind of like, maybe discover it through that iterative approach. I'm curious what you've learned over the years and what might be useful for others who are listening.
28:40Hamlet:I liked those industry style kind of, hey, there's a lot of wealth here, but there's a lot of craziness type books, Bonfire of the Vanities, so on and so forth. That influenced me a lot. And to some extent informs my editorial voice. But you can't have an editorial voice if you don't have a view of the world. And I think people are afraid to have strong views of the world. Because they want to play it safe. They're afraid of getting lambasted on social media, things like that. It's okay to have strong points of view. And it's okay to express those points of view. You can't have 100 % approval rating all the time.
29:25Hamlet:and so uh you just have to lean into yourself and express your actual point of view that's it
29:32Sunil Rajaraman:so that that's an interesting point because you were saying about sort of when you were when you were building sort of the the re the revitalized version or attempting to revitalize the bold italic after you bought it you said that you kind of were trying to you know copy somebody else's voice trying to revive this existing thing um but you felt like maybe that was the safe thing to do and also just didn't resonate. But then the bold thing to do is kind of actually try and put yourself out there and figure out your own thing. And in many ways, I'd actually love to hear sort of your reflections on this is your life in Silicon Valley now, because I think that if people were to read it, we'll link to it.
30:11Sunil Rajaraman:I think if people were to read it, some of it would resonate really strongly and some of it would feel like another country, right? It would feel just completely different from where we are today how did that feel at the time that almost it almost felt to me like it was almost like a gonzo uh type of thing uh you know hunder s thompson and you mentioned bukowski which also has this like kind of like gonzo edginess to it um yeah i'm just curious like what that was like going from trying to do the safe thing which was just continue the the bold italics editorial to like doing your own voice developing your own editorial voice
30:44Hamlet:it felt liberating right i mean because you uh i just had all of this going on you spend a lot of time trying to placate and like oh you know maybe everyone will like me if i stick to this thing and try to keep this formula and then it's freeing to actually just be yourself and uh that is probably the moment of my entire you know i've written a lot in my in my career that was uh that was the most authentic you know piece of writing it was the most freeing piece of writing i wrote once i once i wrote it i knew it would do well like i immediately knew it and uh that's uh it's hard to duplicate that feeling um there were there were other ones in this series that that i wrote that you know felt pretty good but that one i was just like yeah no this is gonna work i knew it and by the way like that's that's sort of how i feel about hamlet i think it's gonna work like It's an obvious idea.
31:47Hamlet:Within that, I'm navigating as a founder what the right product is going to be that's going to launch it to the next level. I know it's going to work. There's something within there that's going to explode. It's just going to happen. It's a matter of time.
32:03Sunil Rajaraman:It feels like often people are trying to find the thing and maybe they kind of talk themselves into the thing work they think this is going to work they they they kind of like push on the idea and they say okay maybe they try and talk themselves into it being good but it seems like there is this sense of what do you actually have the real thing you kind of immediately know it
32:29Hamlet:yeah well in the same way you can't replicate editorial voice you can't replicate that feeling on hey i have something i can work on for 10 years you know i see a lot of right now this is over the generations now, since my 2011, for raising my first round for scripted to today, 15-year gap. In both eras, you saw a lot of founders who, like, hey, I'm going to start a freelance economy company. Then I'm going to start a crypto company. Then maybe I'm going to find a way to create a two-person AI company that generates a billion dollars of revenue by selling GLP-1s, whatever the case might be. at every area you have a bunch of those you know almost no one I can vanishingly thin number will make it because you just can't replicate it you can't do it, it's not possible the whole point of it is there's like an original insight, if you don't have an original insight, just don't work on it by original I don't mean you're the only one in the world working on it, by original I mean you have to have an original insight on that industry or that thing that you're working on that no one else has and if you don't have that you know whatever i wouldn't i wouldn't waste your time what would you say is kind of the thing that
33:49Sunil Rajaraman:surprised you the most recently about building hamlet like you you've kind of been pulling this thread on understanding local government you had this one surprise which was wow you started to get inbound um from customers that you hadn't expected but what's something else that kind of surprised you and how have you made changes based off of that?
34:08Hamlet:I'm continually shocked that people don't always act in the best interest of their communities, which is like a sad realization to come to. And you see it all the time in the news, whether it's what's happening with Swalwell right now and the allegations against him are pretty bad at the moment. And you have a new politician every day who's getting hit by something. This also translates at the local level. I mean, people do not always act in their best interest of the community. They serve their own best interests. That makes me very sad, and that makes this a problem worth fixing, but it's prevalent.
34:51Hamlet:And I hope we need better people to run at the local level, in my opinion.
34:57Sunil Rajaraman:How have you, this is slightly tangential to Hamlet, but how have you thought about supporting others when it comes to running at the local level. I mean, it's clearly something you care about, something you just said, we need more people to run at the local level. Like, is there anything that people who are listening to this should take away if they're interested in that and say, gee, maybe I should actually, I know I'm thinking about founding a company or maybe I'm in the process of like working at a company, but it sounds like that might actually be a good thing to do or at least consider doing.
35:25Sunil Rajaraman:I think most people don't even consider it, to be quite honest.
35:28Hamlet:I would say just joining a commission at minimum is the best thing that you can do. Joining commissions in a city like Orinda, for example, or Moraga, which is a neighboring city, those are appointed positions, not elected positions. So you can literally go on the website. Depending on the commission, they're always looking for people. You can go to the Parks and Rec Commission. Three spots available. You fill out a one-page form. They interview you, the city council. You explain why you want to get involved, your candidacy, of course, if there's other competent and good candidates, you're against them.
36:05Hamlet:But it's an interview process. It's not an elaborate election process. Join a commission. Sure, you become a public official and you're in meetings and things like that, but it's a thin commitment. It's three, four hours a month and you could actually be doing something good for the community. So even if you're just mildly interested, join a public commission. I personally joined a commission, served on it for a few months and enjoy the experience. But if you want to get involved in your local community at minimum, you should do that. The minimum bar is vote for your city council elections. Voter turnout.
36:46Hamlet:For the down-ballot elections, only like 20 % of people vote on city council.
36:52Sunil Rajaraman:Yeah, and hopefully when they have more access to information about what's going on in their community that will actually cause people to have a reason to care more i think it's so opaque and it's so hard to follow that when people don't even know what's going on yeah they just check a
37:05Hamlet:box how could they know yeah or they ignore it they just say hey who's running for senate who's
37:10Sunil Rajaraman:running for governor that's it um so i'm curious how you thought about building out a team early on
37:15Hamlet:yeah my uh it's actually interesting my initial team mostly came from good rx in retrospect, you talk about shifting focus, that was not the right move because we weren't a consumer company. So I largely turned over the original team and I hired a crew from Pivotal Labs. And so I had worked with some folks from Pivotal Labs, including a good friend Roger. They have a great engineering culture. Roger Neal, who went on to be a successful founder. Shout out, Roger. I met someone who was an engineer at Nextdoor, Mike, who became our head of engineering and recruited a whole crew of pivotal engineers who now work with the company.
38:06Hamlet:My instincts were consumer initially. I built the team largely based on good Rx people, but given the direction of the business, it made more sense to shift it a bit.
38:15Sunil Rajaraman:And when you were making those initial hires, was it that you were going to hire sort of one engineer to build sort of the early prototypes? What is that actually like? Because I'm sure there are a lot of people who are like you who have an incredible background that sort of complements engineering folks. You have, I would say, I would describe you as a person who's really good at storytelling, at marketing. You have some strong product sensibilities. but like you you have to think about how to supplement yourself and how to to add additional people on board so what was that actually like if you could just be a little bit more granular on that so people could hear especially because i think there are some people who are who have have a similar profile to you who are thinking about starting companies and maybe they're not
38:59Hamlet:not entirely sure the best way to begin yeah it's a great question i actually started off contracting mostly with my engineers and i did not because i hadn't picked a engineering co-founder I wanted to be very, very careful and deliberate about who I worked with. And I wanted to see how they work. And I contracted with a couple of different engineers before I met Mike. And we started working on the version of Hamlet that became our business product. But for me, it was like a slow dating process where I just wanted to get to know the person's working style. and yeah I have maintained that policy actually where with with technical hires in particular I like contracting for seeing how they work getting a feel for at least a few months before extending offers I know you know in the early days Google did a lot of that contract to hire stuff I'm a big fan of contract to hire and I think it's going to be that way for a little while it feels
40:03Sunil Rajaraman:like a lot of people do it and at least solo founders that we've talked to recently and I think that they're always thinking that it's like uncommon so I think it's just one of those things where maybe the industry hasn't actually caught up to the ground truth of it because I was talking with Paul from BrowserBase and he had a similar story where he got started with contract to hire and it was a great it was a great way to get to know someone have them get to know you another thing that people say about this that I've talked to is you know it's really great because if you're contracting to hire you might not necessarily have somebody who is fully capable of letting go from the other company do you have people who are sort of doing it part-time or were you only doing contract to hire with people who are truly full-time on on hamlet in
40:45Hamlet:the early days it's varied i uh i had a couple people who were part-time um and i had uh i had one person who was more or less dedicated uh to hamlet full-time it's it's been a mixed bag um But they all had very, very unique and good backgrounds. I mean, why I ultimately hired Mike as my first proper head of engineering hire was because he had worked for Nextdoor for six years. And so not only did he have great technical skills, but he did care about the problem and had some context on it that others just simply did not. And so he's just a great guy.
41:28Sunil Rajaraman:And when you went from making that first hire through the next few, what was that like? How were you making a decision about what to hire? Was it all engineering? I think it's just really useful for people to hear how different businesses approach this to building the team.
41:41Hamlet:Yeah, a couple of the hires from GoodRx were more marketing and product-centric. And another person who kind of helped with a lot of stuff at the company and was more ops. Lindsay who's now running customer success for us she's awesome and I let Mike recruit the engineers and he created an amazing recruiting pipeline from Pivotal and so we still have several Pivotal engineers at this point but the company's 11 people, 6 engineers right now so we're keeping it very lean for the time being
42:24Sunil Rajaraman:I think that one thing that people sometimes have to navigate when they're getting started with a company is they might be used to building companies, but they might not be used to building for the type of customer that they're building for. In your case, I don't think that you've ever sold to some of the people that you're selling to. What was that experience like? How did you run up that ramp? I think you mentioned part of it was getting advisors to help you understand some of the landscape around this. But when you think about pricing and sort of understanding how to sell to these customers that you've never sold to before, what are some things that you've learned through this process?
43:02Hamlet:I don't know any founder who's like ever said to me out loud, wow, I'm like the best at pricing. I've just got it nailed. But I still don't quite know how to price this product. We have an ongoing use case. And so we defaulted to subscription because it turns out meetings happen all over the place, right? In cities everywhere in America. And so just the logical place we landed was subscription based on the number of cities you subscribe to. And there's some time savings and things like that. In terms of understanding the customer, advisors help a lot. I attended a lot of industry conferences, whether it's the International Builders Show or Blueprint, which is the largest conference dedicated to real estate and technology.
43:49Hamlet:And you just kind of have to meet people in person. you can't just do things over Zoom anymore. You have to really get in there. You have to see what other people are selling, whether it's your peer tech companies or those big pain points for the customer. You learn by being in the room with people. We're still learning.
44:13Sunil Rajaraman:We've got a long way to go. When it comes to conferences, I think that some businesses do really well at conferences. Some startups, it's a big distraction, especially the more sort of generalized the conference and maybe the earlier the startup. I'm curious what you've learned from attending conferences over the years at various companies. And are conferences particularly good for Hamlet? And how should people think about approaching conferences?
44:39Hamlet:Yeah, it depends on who your customer type is. Our customer type just happens to go to conferences. Do I savor going to conferences? No, I really don't. But look, conferences are back. and if you're going to build a business like a Hamlet where you're selling to an industry that's traditionally viewed as older school, etc., this is how people interact. We went to a data center conference in January in Honolulu. 6 ,000 attendees working on data centers. They range from construction to development to financing, everything in between. But that is the place where they get together every year. if you have a few of those in your industry you should probably go to them at minimum attend and potentially exhibit but that's hit or miss it can get expensive but at minimum you should attend and try to get speaking or something like that going
45:36Sunil Rajaraman:This is something that people would probably find really interesting and probably want to learn from what you've learned so far so you go to these conferences there's lots of people who are attending them all sorts of areas within that industry. So data centers is an example, right? But I'm curious, like what other things you've seen when you go to the conference? Like how do you, do you approach people on the conference floor? Do you go and try and talk to people at booths? Like what are some things that you've seen that have been useful?
46:03Hamlet:The thing that's always been helpful for me and I try to walk away, like you want to walk away making some sort of impression. And that doesn't necessarily mean, you know, getting a booth. That could be going to a well-attended session and you know they give you the opportunity to ask questions at the end you force yourself to ask a question and it's a good question a question that everybody in the room is thinking god i wish i asked that question because that's like deeply insightful it's simple but insightful and that's consistent with our editorial voice right being thoughtful about local government i at minimum always try to ask a question at a crowded session of a speaker that i respect and you know part of it is i'm genuinely interested in the answer to the question but there is an element of theatrics to it which is like hey there's that person who asked the question you'll find more often than not they'll come up to you after and say what a good question and that makes it easier to have a conversation starter uh so that's one thing i do we're going to try a lot more this year to so i'm going to a conference in may um i'm reaching out to conference organizers in advance and just offering them free data like that we could share and so that's a way to add value to the you know experience of the conference without having to do a booth or having to go up to a bunch of people but it's like unique original research that we basically we only have that we can give to all the attendees and that's an easy conversation
47:37Sunil Rajaraman:starter obviously but we'll be doing a lot more with that that's cool what are some other areas that maybe you hadn't tried before but have been useful for you when it comes to getting customers or talking to potential customers?
47:51Hamlet:Yeah. One thing I'm deeply interested in is the nature of our customer here is they are usually parts of industry trade groups, whatever. Giving them free or some sort of access to our tool which is easy to try, I'm going to be doing a lot of that more. and that's the nice thing about having buyers who get together a lot is they have industry associations they have they have venues to get together and and so you can if you show
48:24Sunil Rajaraman:them the value of the product it can spread like a contagion in a good way there was one thing that that i saw that was really interesting i probably shouldn't say the name of the company but something that really surprised me was how valuable niche podcasts are for certain types of businesses. There's one podcast that a friend runs for his company. He probably has about 100 listeners per episode, but those listeners are incredibly high value for him. When I think of a podcast before I talk to him about his, I kind of assumed it was hundreds or thousands of listeners. I didn't really know much about sort of this idea of niche.
49:01Sunil Rajaraman:So I'm curious, is there anything around truly niche media when it comes to hyper-targeting the right people. Do you have any thoughts on that or things that you've learned about that over the years? It makes sense that it would work.
49:22Hamlet:I've never personally paid for super niche media because of the high CPMs. I always shied away from it. I will tell you that the most effective marketing that we did at GoodRx and something that I want to emulate a little bit more. We used to spend a ton of money on boxes that we would send to doctors' offices where they would dispense GoodRx cards and the doctors would display these cards. And why would they display the cards? Because they want their patients to adhere to the standard of care. And so they didn't care that it took up real estate in their office space. but it would create a one-to-many relationship.
50:05Hamlet:In addition, there was a lot of trust in the doctor. If they put it up there, it must be a good service. That's something I think about a lot. I'm always looking for analogs for my own business. That's something I think about when I think about other people's businesses. What creates a one-to-many type relationship through a trusted source?
50:27Sunil Rajaraman:Maybe as we close here, I think that there's two questions that we'd love to ask always, which is the first one is sort of the bear case for solo founders, like why you shouldn't do it, why people should maybe have a co-founder or maybe not even start a company in general. But we'll start off with the bear case for solo founders, and then we'll switch over to, you know, we'll take a break and maybe we'll talk about it, and then we'll switch over to sort of the bulk case, the case for solo founding. But maybe start with the bear. oh my gosh the uh i think uh you can feel and you got to be very careful you can feel resentful
51:09Hamlet:toward your team for not caring as much and that's something you constantly have to manage is like you're not in competition with your team to show them like you know you can do more or you should you should you know feel obligated all the time to pull them in a certain direction and things like that. It can create an interesting psychology between you and the team that you have to really actively manage. And if not actively managed, then if there's not good communication, that's a real problem. Because you have a strong point of view, a stronger point of view as a solo founder, and there's nobody else there to gut check you.
51:51Hamlet:And so you have to check yourself and have a team you can talk to about your kind of leadership team that you can talk to about your problems and say like I feel this way, this made me feel all sorts of ways but if that's not managed, it's bad. It's easier to fracture the team as a solo founder.
52:10Sunil Rajaraman:That is incredibly valuable and incredibly important and absolutely true and I've heard similar things but we've never recorded anybody talking about that. Can you share a little bit about how you might be able to as a solo founder kind of notice when that's happening and also maybe do something to address it in yourself
52:30Hamlet:so i spoke to my uh zach and marisa my my two very valued leadership team members the other day i was feeling it i started to write it down last weekend over some stuff and i talked to them directly about it yesterday and uh we had a good back and forth session about it but like you have to be able to do that with your team. It was a list of five things that I wanted to talk through that had been building up. But when I noticed them, I started writing it down. Then I felt comfortable enough talking to them about it. We went through it and that was that. If you don't have the maturity to do that, it's not good.
53:18Sunil Rajaraman:Lastly, what is the case for solo founding?
53:20Hamlet:oh my gosh i uh i love what i do when i wake up every morning i love having the the freedom to decide what i work on um and you can go further faster you can go a lot further a lot faster and i rise to the challenge i'm a competitor and like you know um i don't have to wait for somebody to keep up with me and like you know have the same thoughts feelings insights I think you made this point earlier, which is I think sometimes when there's consensus, there's an average outcome. I feel like I want to optimize for like an extraordinary outcome and crazy ideas. And I feel, I feel, you know, untethered by, you know, kind of like having to go to consensus to come up with ideas, you know, and, and you can get a more extraordinary outcome as a result as a business.
54:16Hamlet:Fulfillment wise, et cetera.
54:17Sunil Rajaraman:so yeah cool well thank you so much for doing this this is great thank you thanks for having me if you enjoyed this conversation we would love it if you could share solo founders with everyone you know particularly people who are considering starting companies solo or who are already doing it you know the entire goal of what we do is to normalize solo founding encourage more people to solo found instead of end up with co-founders of convenience if you'd like and we'd really appreciate it you can go leave a review on apple you can go give us a thumbs up you can subscribe on the YouTube channel.
54:48Sunil Rajaraman:Anything helps. And of course, if you are starting a company or considering starting a company, you should go look at the Solo Founders program. We work together with you in San Francisco alongside of a bunch of other Solo Founders. The idea is it's much better to be Solo together than to be Solo alone. I'll spend a lot of time helping you. And we also invest$100 ,000 in your company. So if you're excited to learn more about that, go check out solofounders.com slash program.
From the publisher
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.




