Protecting the City Chapter 02
Simulant: Sahil Lavingia
Role: Co-Founder
Company: Gumroad, Flexile
Guided by: Kristian\ Michail
Role: Founder
Company: Simulations
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Start Simulation ↓
Reading Time: 25 minutes
In this simulation, a founder is annoyed at the state of his city. With his own business booming, he cannot sit back and watch things fall. Through simulation, our personal frustrations inspire our most public service.
① Context
Let’s get started, Sahil. In your own words, who are you and what are you working on?
The first slogan I came up with for myself when I was a kid was 'I like building products, and I like building them for fun and profit.' I still think today that this is a pretty solid framing of what I try to do with my time: building stuff for fun and profit. All those things have to be present for me to want to spend time, energy, effort, and intention on something. That's how I kind of think about my identity.
I built a product called Gumroad; that's the core thing people probably know about. Before that, I built Pinterest for iPhone. And yeah, I've devoted my time to building high-quality user experiences, typically in software. I charge money for my product so that I can do it profitably and then use that money to help make my life and other people's lives better."
You’ve built a reputation of not necessarily being anti-VC but definitely a self-funded bootstrapper. How does that speak to your identity?
Yeah, I mean, I think raising money is a tool, right? It's leverage, like debt or getting a loan. It's just a thing that exists, much like America exists—it's a legal framework that you can take advantage of it if helps you achieve your goals sooner and faster. So, I would just think of venture capital as a straightforward utility that exists. Venture capital is well-branded because you become a venture-backed company, but no one says anything about you if you have a loan from a bank; they don't label you as a bank loan company.
That's how I kind of think about VC—it’s just a tool that exists, and you can use it, whether you sell 5% or 1% of the company. If it gives you a lot of leverage to accomplish your goals, then it can be a really good tool. However, it shouldn't be the be-all and end-all, right? Ultimately, I believe you still have to build products for fun and profit. VC isn't required for either of those things. So, it has to become more fun, more profitable, or you have to be able to build more products, right?
Being honest about why we're raising venture capital or using any other instrument, I think most founders are probably not sincerely interested in those core values of product, fun, and profit. Perhaps most just become founders because they aspire to become billionaires or something like that. In those cases, I’m not going to align very much with those kinds of founders.
That's cool. I've never really heard it said like that before. Now that we have context, let’s proceed.
② Challenge
Is there a challenge you are currently working through or thinking about that is super important to you? Anything irritating, aggravating or frustrating you? Whatever it is, make sure whatever you choose is a worthy challenge for us to explore in the next hour. The more important it is, the more potent your simulation.
Yeah, sure. I can give you a few.
One issue is the New York City ferry system; I believe it could be significantly improved. There are a couple of core issues that I think can be addressed with technology. There's a lot to discuss about enhancing its current state, and I believe we can extend this challenge to the entire US federal government.
Additionally, we can delve into exploring how cities respond to fentanyl and drug-related issues.
There are certain things I don't think I can change, such as the weather. It's currently grey in New York City, which makes it harder for me to want to go on walks, hang out with people, and be social. So, the second-order effects of the weather present a challenge.
Flexport is a new product we're working on, adjacent to Gumroad. I often contemplate how to achieve product-market fit for it, which we haven't reached yet by my current definition—being cashflow positive, making more money than we spend building the product.
Cool, a lot of these are external challenges such as things happening outside in the world like fentanyl, for example. I'm happy to go down the external line of challenges. I'll also ask if there is anything internally that’s challenging on a more personal level. I just want to give you the option to explore both before you choose which avenue you would want to go down.
Currently, I feel like I have a pretty good internal state. I've been contemplating improving my morning routine, but overall, I think I'm in a pretty decent place there.
Honestly, I find the New York City ferries to be a rather interesting problem. I believe it's somewhat connected to my internal state because having a much better ferry infrastructure and general civil infrastructure would make my day more compelling. Right now, there's a lot to unpack regarding why I see room for improvement and why this would be such a significant unlock for me.
I also believe we are undergoing a societal evolution, primarily around work, and foresee a significant shift in our relationship with work over the next 20 to 30 years. I don't think people have evolved as much as they believe over the past 2000 years, and the world has yet to grapple with the looming technological dilemma. It's expected to become unbearably intense, especially with increasing automation. Things are going to get crazy.
Additionally, with globalization in the next 50 years, the cost of unskilled labor will no longer be cheap. The demand for robotics will soar, leading to a substantial shift. So, I am contemplating how to prepare the country and the government for that significant change, and the New York Ferry System is a good example of something lagging—just a poor user experience overall.
Cool. Be specific with your challenge. Whatever you choose, just make sure it's the most pressing thing on your mind. Then let's get to work on that.
Let’s explore the New York Ferry System.
③ Character
Which people are the current obstacle regarding the New York Ferry System?
I'd say it's mostly the New York City government, not in adversarial terms but in terms of the government being the decision-makers. This is where I think the bottleneck is.
What would you currently label either the New York City Government or the people who operate the ferry system? In two words, what is your criticism of them?
I would describe them as slow and distracted people. It's not that they have bad intentions; it's just that they wake up every day, and it’s like they are that meme where the dog is in the burning house, yet the dog still acts as if everything is fine. This stems from public servants spending 99.9% of their day trying to put out fires, leading to constant distraction.
Perhaps 'slow' may not be the right word to characterize them because I don't necessarily know if they're slow. It's just that there are so many things happening poorly, and to truly get a grip on the situation, it requires a level of competence that, frankly, I think most people just don't possess.
For instance, the fact that I have a ton of free time due to the autonomous and asynchronous way I have built Gumroad allows me certain freedoms and spaciousness in how I work and live. On the other hand, most government officials have young children, adding another layer of challenge on top of the shoddy work structure and ongoing crises.It's a common issue, making it the worst time to be a government official while raising young children.
Frankly, there's no time left for them to be the best government official. The best government officials, like George Washington or Benjamin Franklin, had the space and competence to excel. So maybe they are not slow, but they are definitely underwater, struggling to breathe. They are like drowning, distracted, flailing people. That's how I perceive it.
So if you could call them a character, are they like Drowning Flailers?
They are Flailing Drowners.
So if they are Flailing Drowners what does that make you?
What does that make me? Interesting. I guess it would make me a sleek and efficient shark. One that swims, floats and flourishes in the water. One that even scares a lot of people, especially those drowning.
Is that it for you? Do you feel like Sleek Shark is your character?
Yeah mean, just in the context of water, drowning and all that stuff. Maybe a Lifeboat Deployer may be a better you know, kind of what I'm trying to get out of this is that I just want to be helpful. And like, help take some load off.
Well, there are two options there between Sleek Shark and Lifeboat Deployer. There is tension here. It’s a good thing. You’ll see why later. If there is one that you would choose that feels most resonant, which would it be?
Let’s go with Sleek Shark.
④ Facts
🅐 Doing
Alright, Sleek Shark. Let’s look at your doings. What are you doing day to day? What are the actions, tasks and jobs that you do in this character?
I pound my nose. I slam against the concrete wall of the city. I’d explore the edges. I try to find the nooks and crannies to squeeze through so I can get in and do stuff. I swim around. I explore all the cities’ waterways. I breathe in all the characteristics of my environment like a good mammal does. I think sharks are mammals, but maybe not. The core thing I do is probably just think about how to solve the problem in front of us. I’m trying to make the system more efficient and get rid of the unnecessary blubber in the body that may not be necessary and may be slowing us down from cleaning up the ocean full of stuff. I am seeking efficient systems.
It's not just about being quick with getting stuff done. It’s about the stuff you don't do rather than the stuff you do. So for example, being productive. It's not necessarily about doing anything. To be productive is easy. You just have to not do three things like don't go on social media, don’t watch content, and don't play video games. It’s like avoiding these things and you’ll eventually become productive. I think being Sleek Shark is about avoiding these dangers.
You know, I don’t sit around and do nothing. I get out of bed, I do stuff. I meet people constantly. I work on ideas, I try to improve my ideas. I hire people who could improve my business and my aspirations in life. I try to explore new parts of the city. I try to think about where I may want to go next. I do stuff. I hosting a meet-up instead of thinking about hosting a meetup.
🅑 Having
Ok, let’s move on to your havings. What do you have in your life Sleek Shark? These may be physical or more ephemeral things that you have in your possession.
I have a beautiful little house. I have two cats. A wife. Nice furniture. Heating and Cooling. A hot shower. A fridge. A freezer. A team of software engineers, product designers and customer support people that allow me to solve any problem on the internet with software. I have a US citizenship.
I have a phone with the Kindle app on it. I think is pretty critical. Just to read a lot. You know, trying to find your stream and not using what you read on social media or other recommendations. I have my own space to read, think and form a worldview.
Ultimately, I think a shark is first. If you're successful in any way, you must be first. You can't follow others and be successful. If you don't find your own stream of thought, you can't be first. You'll be another fish swept with the tide. The shark finds his own stream. The shark is first. I guess that's sort of why I was drawn to the shark. Sharks don't follow other sharks. Maybe they do for mating. But certainly, the best ones don't follow. At least in my head.
How about things that you don't have as a Sleek Shark?
I don’t have full-time employees, I have contractors instead. I don’t have a full-time job. I don’t have a massive family or a strong cultural background. I grew up in Singapore, which is such a young country. The American schooling system within Singapore is even younger. So when you grow up in this Russian nesting doll of cultures, you aren't beholden to any of them. You come to realize that they're all kind of made up. So anyway, yeah, I feel like I don't have a super strong cultural filter. Like if there's some news about something, I don't put it through the frame of my cultural background. Whereas if you're strongly affiliated with certain cultural roots, you may say, ‘Hey, what do people from my cultural background think about this thing?’ I don’t have vegetarian impulses. I’m a shark. I like meat.
🅒 Being
All right. Let's look at your being now. What ways of being do you express in the world as Sleek Shark? This is not how you're feeling, but more so the styles in which you predominately express yourself. Being is kind of like the all-consuming expressions of the character.
I guess being on the hunt is one way to think about that. You know, I'm always trying to search for opportunities. It's sort of the hunter-gatherer thing that most people are familiar with, but I think I have a strong proclivity toward hunting. Generally in the context of looking for food, but, when basic needs are met, and you're not hungry every day starving, there is this proclivity to hunt because you've been trained to do so. It's more about enjoying the hunt. Not for the food, but for the exercise almost.
So is that playful as a way of being?
Honestly, no. I wouldn't say that. No one who knows me would say I am playful., I'm cerebral, but I don't think take things very seriously. So some people would say, you know, you're not very serious. Therefore, you must be playful, but I'm also not very playful. So I don't know. I don't know where exactly I where I sit on that spectrum.
I think the word is irreverent. I don't mind poking fun at stuff but poking fun in an irreverent way. I'm too lazy to be truly playful. You know? I feel like the most playful people in my life are the extroverted people and I'm just not that.
What else in terms of ways of being?
I'd say I’m hard-working. I like doing stuff. I think the word would be restless. I rarely take a break. I'm not interested in the celebratory aspect of my work either. If I were in the NFL or whatever, I would not be interested in the celebration after the Super Bowl. I'd be interested in winning and then going about my day, which I think is quite different to other people operate.
Let’s look at the opposite now. What are ways you're not being? Maybe there are ways you don’t get to be or ways you have not got to be very often.
I am not being reactive. Like someone who's underwater and can't breathe. I guess not being a Flailing Drowner, right? You know, the nice thing about being goal-oriented is that you are choosing your goals and a lot of people don't get to do that because they are stuck with a medical degree and they're just trying to be a nurse because that's like the path that they're on.
I try not to get too upset. Let's say a flight gets canceled or delayed and you have to make a bunch of decisions very quickly that may have other consequences. I think some people struggle. They freak out, they have a meltdown, they start crying. Being flustered is not a very common way of being for me. I tend not to freak out.
Great. Is there a way of being that you want to be but you haven't got to be up to this point? Even as a Sleek Shark, is there a way of expressing yourself still on the horizon that's foreign to you?
I have yet to be a father. So that's like the biggest thing that is sort of on my horizon that will change my way of being quite a lot, presumably. But I can't prepare for that too much. I can't seem to make that change happen ahead of time.
I think the biggest change in me will probably be some level sort of protection. Being protective comes to mind. Where you just care about this one little human so much. That's my guess.
🅓 Wanting
Cool, you said you want to be a father. You also said you would want to see an overhaul of the whole New York Ferry System, which is how we started this conversation. Are there any other things that you want?
I would say wanting them is probably even too extreme. They're not things that I want, but just things to do. The goals that I have, I don't want to even accomplish the goals that I have. They're just something to set a framework for me to rationalize my life. But yes, I think those two things are good.
I don’t want to die. That’s a big one. Cool with everything else.
Anything else you don't want besides not dying?
Generally things around pain. I don’t want physical pain or people around me dying. You know, loved ones dying and things like that.
⑤ Choice
It’s time to make a choice. You’ll be invited to choose a character that can get you what you want. Let’s explore these options together.
Firstly, what’s the opposite of Sleek Shark?
It’s Flailing Drowner, right?
Not necessarily. Maybe they are the opposite. But maybe Sleek Shark has an opposite that’s yet to be identified.
Flailing Drowner seems right.
All right. So it seems quite clear that Flailing Drowner will not be the thing that gets you what you want. Is that correct?
To be honest, maybe it will. I do think that personality would probably be successful at being a good father as well as a potential candidate for improving the New York City Ferry system. There are many fathers and there are many people successfully helping to run the ferry system already. And you know, being Sleek Shark is not a requisite for being a good father. Nor is Flailing Drowner a requisite for running the solid ferry system either.
I see a clear tension. I'm hearing there could be an upgrade that goes beyond Sleek Shark, without completely writing off the Flailing Drowner. A character that allows for something more. I want to give you space to think what that could be. What character comes to mind that could give the efficiency of a shark but also the nurturing side of a father?
I mean there is probably a more nurturing character in the ocean. Maybe a Lifeboat Deployer. Maybe it’s a Whale Shark. Maybe sleek is not the right word. Like it's you know, more mindful. More thoughtful about solving the problem because it's not as caught up in like the detail and like the, you know, the daily grind of just living as a little fish in the ocean.
Maybe it’s something even beyond the ocean. If you could choose two words that speak to who this character is, what would they be? It doesn't even have to be shark-related. It’s time to choose what moves your heart most.
I would say ever-present.
Also, the word moonlighter. The vibe I get from that is not a vigilante, but someone who's working in the background and is always there. I like Moonlighter as a phrase. It's like a freelancer. You know, someone who you can kind of rely on and is always there. Especially in the hard times when most people are not there for you.
I'm gonna say Everpresent Moonlighter.
Very cool. How does that feel now?
It feels good. It’s like a special dedication to side gigs and quests for the good of the people. Some people have a full-time occupation but they still have time and ways to engage and connect with society on top of that, in these moonlighting gigs. It’s pretty awesome, I think.
Your arrival at Everpresent Moonlighter was beautiful to witness. So thank you. Say more about this feeling and where can you locate it in the body.
I mean, it’s probably my hands. I’m thinking about the amount of grip strength and how good it feels to hug someone. I think there's something about the hands. And I think, you know, at the end of the day, when you build stuff, it's mostly with your hands. So hands, yeah.
That is awesome. I'm hearing the feeling is love. That you're feeling a real sense of love.
Yeah, I guess it’s all that it comes down to. It's kind of cliche but just trying to find ways to help other people and it's like a bi-directional exchange, because you help others and then by helping others, you also are seen by them and others as a helper. So it feels good both ways. I think it's a positive sum game, as some would say.
Sweet. Let’s proceed.
⑥ Simulation
Can you close down your eyes now? I'm going to close them down with you. We'll take a deep breath. Then let’s breathe in through the nose and out through the mouth. We want to slow down now and feel the space, Everpresent Moonlighter.
Would you be able to take me to a moment in time, an event or experience in your life, where you felt like Everpresent Moonlighter was undeniably true?
Yeah, it’s when I was pretty young in my web design career. I was doing some design work for a social studies teacher in my high school. I was spending dozens of hours trying to learn web design to deliver a website using HTML, CSS and all that stuff. And yeah, just really feeling like “Wow, I get to make money doing this and I like the feeling of making money.”
I assume at the time it was like the equivalent of doing heroin or something you know? Maybe still it is like that, I guess. It was cool. It’s like I can just like learn this skill and I don't need to talk to anyone. I just have to watch YouTube videos, put my head down and just learn this skill. And if I learned this skill I could make like $5 an hour. And that was all very appealing to me.
Also, this forged a relationship with a teacher outside of the standard student-teacher framework. It gave me an early insight into how society is this kind of a made-up invention. And all these social contracts are just agreed upon by both parties. But like, at any point, the student could become a teacher, the teacher can become a student, right? And like, there are all kinds of made-up rules to make society not implode on itself.
How does that link to your kind of watching out over the city kind as you described a moonlighter does before?
That's a good question. The truth is it's very difficult to contribute as a side hustler in the public realm. One thing that attracts me so much to private matters is you can just find avenues to add value in certain small ways and build up a portfolio and all these sorts of things. But with government and things like that, you have to spend 20 or 30 years committed to the bit to make a positive change. I'm trying to find these kinds of opportunities and problems that I think are on somebody’s to-do list 15 years from now. Like the other day, I was walking around and was like ‘Oh there should be like white noise cancellation on trains, where they install speakers, and then have them emit noise cancelling frequency in certain places in the city where the train is super loud and that are essentially dead zones during transit. The moonlighter is ever-present and always thinking about that stuff. As he goes for a walk, he explores and that’s how I spend time in my day. Just looking around, looking up and saying, “I wonder if there's a way to improve this sort of experience for the next human being who goes on this walk.”
That was beautiful. Thanks for sharing. Let's keep your eyes closed. Take me to a far-distant place in the future. Maybe it has no years. Maybe it's nearing the end of your life. What event has happened in the future that is living proof that Everpresent Moonlighter real?
I would probably be living on the top of a mountain somewhere. A bit like Ayn Rand’s Atlas Shrugged. She writes about this village of people who live in the middle of nowhere, outside of civilization. And they're just hyper-competent people and they just live alone because they're kind of tired of this sort of direction society went in. A lot of people have that similar dream, of moving to the middle of a mountaintop and having people who care enough about whatever they happen to care about, that have others visit them. This is very, popular in India. It’s the same sort of template that Jesus used right, in terms of like, gaining a following and teaching people. I think that's often a sign that you lived your life well is that you can kind of sit somewhere and people will choose to listen to you, which is very rare. I think. One thing I've noticed is most people tend to listen to people who are roughly in the same generation. So if you're rable to get people from the next generation to listen to I think that's very laudable.
So kind of like a holy figure or a saint?
Yeah, I mean, hopefully, I would have something to offer people. And I would be kind of lazy at that point. Hopefully people would be willing to come to me instead of the opposite. And I also just think that there's like a lot of value and you know, in building what I think is needed. Civilisation is largely just housing and agriculture. And some healthcare and medicine. So if you want to create more physical value, just move to the middle of nowhere and build. Once you have enough clout, you can do that. You can move to the middle of nowhere and start a city right? Just start building a school infrastructure buildings. And this is how every city was built. Someone with a following, basically said, “Hey, I'm going to go over there and start a new city.” So yeah, I think someone who starts a city, a cult, a religion, a startup is the same archetype of each other, just manifested in a different form. They're all philosophers, right?
They're basically like the Plato or Aristotle figure. I don't think they are different from Jesus or Naval, Bill Gates or Zuckerberg. They're all just trying to pursue the truth, build things and write down their thoughts for other people to read. And balance all of that with having a family and all that.
Cool. Eyes still closed. One year from now, exactly. You are Everpresent Moonlighter. It's real, it's alive. It's moving in your world. Where would you be? What would be happening? What has come true that currently is not true? You may even deem it a miracle.
I think that miracle would take two forms. One would be in the form of an elected office position where I'm now in charge of something because a bunch of people voted for that. And then the other miracle sort of thing would be a dramatic change in living location. I think dramatic changes in locations are tied to big events, pivotal moments and identity shifts. I just moved to New York recently, so I'd be surprised if it happened again so soon, but that would be miraculous if it happened. I would probably stay in New York, but if I moved somewhere, let's say I moved right next to the ferry system depot or something. That would be a good sign.
Ok, so not straight to the mountain top?
Yeah, that's when I'm old and grey. We have plenty of stuff to do before then.
⑦ Integration
Just lastly, before we wrap things up. Any final things you want to say?
Simulation is fun. I like the format a lot. It's different than the typical podcast, bio, blah, blah, blah. I'm happy I did this. I’ve been visualising naturally since a young age, however, this conversational approach adds another dimension.
Did you notice the clear transformation or evolution in where you started and where you ended up?
I wouldn't say it's a super obvious upgrade. Mostly because I went with Sleek Shark very quickly. But yeah, the awareness of the word Moonlighter. I think is a very interesting one. I hadn't thought about it. There is something nice about the moon and being a shining light in the world.
Here are my comments from what I've experienced. The energy in your voice that arose when you created Everpresent Moonlighter, in terms of decibels and radiance was stronger than where you started. Sleek Shark was cool but there is something very intentional about being a moonlighter. It moved you from swimming in the ocean to the top of a mountain, and looking over New York City, a bit like Batman. I also felt this moonlighter energy wanted to come closer towards fatherhood and being protective as well. That's what I experienced. I'm not saying it's the truth. But as someone who's mirroring something back to you, that's where I felt your evolution. So take it or leave it, but I was inspired to see that transformation, live in action.
Awesome. That's useful to know. Thank you for the experience.