This is obviously oversimplified but I think this is a big factor:
Singapore is a business masquerading as a country. While it is technically democratic, in practice there are some barriers preventing truly free and fair elections. That being said, the leaders in Singapore are not corrupt and truly do focus on what's best for the country. As a result decisions are made quickly, for the greater good, and are not politically driven. The leadership have the latitude to make decisions that they believe will make the country better. Sometimes these decisions don't have a lot of public support (because people are naturally more short-sighted) but, because of the political system, they don't need to rely on public support.
In the case of Singapore, I think this dynamic has led to a compounding effect of good decisions that have put the country in such a strong place today. You see this similarly with Norway's oil fund; it was likely unpopular initially to reinvest so much money into savings, but today it's paying off where they have a $2T savings account, from which they can withdraw up to 3% annually ($60B) for the needs of Norway.
> That being said, the leaders in Singapore are not corrupt and truly do focus on what's best for the country. As a result decisions are made quickly, for the greater good, and are not politically driven.
But what makes them act this way, lol? That's what every country wants out of its leaders. Why is Singapore able to do it? I know that's a hard question to answer...
> Singapore is a business masquerading as a country
I don't see why this would lead the country to being well organized. All the big businesses I've seen are very inefficient and disorganized internally, where decisions are made slowly, mostly to benefit the decisionmaker's little princedom inside the company.
In my experience (enterprise software), customers buy our products not because we have a moat or some hard-to-achieve technical advantage but because they can speak to us in their words, they know we care, and we try solve their problems quickly.
Just yesterday I was speaking with the COO of a $200M/yr revenue company in the supply chain space. He'd learned Claude Code and built a couple apps to solve internal problems but reached out to talk to us. I asked him "you've been able to build some really impressive tools, clearly you can solve your own problems, why are you talking to me?" And he said "I have a business to run. I shouldn't be coding. I need somebody who understands my business & can solve my problems without taking a lot of my time."
Is there a cheaper way for him to solve his problems? Absolutely. But he wants to put the key in the ignition and know the car will turn on every time without thinking about it. There is an endless list of problems to solve; I don't think software businesses are going anywhere anytime soon.
This should be the top comment. The thing about growth of businesses overall, is that they want outsourced capacity (that’s what employees or contractors are) and that dynamic doesn’t go away because of AI, because like the comment mentioned, it’s not reliable enough in the sense that it can accept high-context vague instructions and ‘figure it out’ like an enterprise developer can.
No, they want "outsourced capacity" from contractors with domain specific expertise. Too many freelance/indie contractors on here scratching their heads as to why to can't land clients or jobs — you need domain expertise and experience, not just the ability to write code.
I even dream of build tools for business to make apps (like Air table, but better) and even if you can do anything that do, perfectly, the software they need not means they want to babysit it all the time.
Is like the person that knows how cook, amazingly, yet hire a chef for take care of it most days.
Obviously a COO shouldnt be prompting Claude Code but your competition is someone in their team doing the same. The person in their team is trusted and knows the business.
I mean its a matter of RoI, isnt it ? Investing in your existing partnership means that specific business can come to you for their problems rather than work up so much expertise bloat. I suppose there a point after which more expertise hurts a business.
A really important part of this is the emotional component. When real money is involved, then you will sometimes face actual losses. It’s hard for a human to completely trust the machine in real world trading
I’ve stayed >150 nights at Marriott hotels this year and was pleasantly surprised when Sonder started popping up as an option. But the thing I noticed is that, at least in the markets I visited, it was often MORE expensive than the local 4/5 star hotel. But with the hotel I got the guarantee of breakfast, a good gym, 24 hour reception, upgrades, laundry service, etc. As a result I never booked one.
My feeling with Sonder is similar to that of my feeling with Airbnb: it’s fantastic for those longer trips where you want some extra amenities in the room like a kitchen. But, for general business or short-term travel, I just don’t get it. It no longer wins on price, and it loses by an order of magnitude on convenience. Why not just pick a hotel?
When I first booked with Sonder back in 2023 in Montreal, they were $20-40 less per night. This year, things were about break even.
At least in Montreal, the Sonder offered a very nice location in the city (especially taking into account my office location) where there were very little chain hotels nearby. I saw it as a "more predictable AirBnB".
Bummer, I really liked being able to stay in that area.
I anecdotally find flight prices tend to follow a cosine wave. Starting high, dipping a couple months before, and shooting back up. You can see these sorts of trends on Google Flights which will show historical pricing for your search query.
And it can be helpful if you’re very flexible. If my dates are very strict then I’ll tend to book further in advance, whereas if I have a lot of wiggle room then I’ll wait it out.
My biggest takeaway from this article is that I should go and see which of these systems have APIs I can query, because if I have a lot of flexibility I think it'd be easier to script it than clicking through a whole bunch of different options on google flights trying to find what the cheapest fare is. I want to be able to write a script that says "here are my dealbreakers, here are the range of dates I can leave on, here's the range for coming back, go and find the best deal"
I guess that's the type of service people typically build and charge for.
Using that as a template, I would find it difficult to argue against a claim. e.g., the evaluator linked above permits any bumper scratches smaller than 6 inches, or a wheel scratch less than 2 inches. I feel like it permits reasonable wear and tear.
However, the example in the article was for 1-inch wheel damage, which would be permitted by the evaluator, so I guess the AI flags _any_ damage. I wonder how receptive these businesses will be to negotiation and pushback. Maybe they'll capitulate if you push hard enough, but it puts an unfair burden on the customer to argue against unreasonable claims (likely by design to maximise cash collection).
I used to be a devout Airbnb user. I never had a horror story on Airbnb, and I certainly had a lot of very unique and interesting experiences that I've never been able to replicate in a hotel environment. But ultimately I gave up on it because there was too much friction. Strict check-in hours, strict check-out hours, a list of chores to complete before you leave, not possible to check in at odd hours, nowhere to store your luggage, spotty wifi, the list goes on. Previously I defended this friction with the economic argument - hey, at least it's a lot cheaper than a hotel - but Airbnb no longer wins on cost.
That being said, I still use Airbnb but now only for very specific cases - e.g., some friends and I rented a large lakefront cabin earlier this year. Previously it was my first choice and now it is my last.
(I admit as well that I travel very regularly - around 100 nights so far in 2025 - and that a casual traveller may, understandably, have a different perspective)
There are two fundamental ways to win a negotiation. By "win", I mean achieve an outcome outside the norm, such as an above market rate salary.
1. Negotiate from a position of strength
You pointed out a couple of these, like when you have a strong personal brand (like Patrick) or when the market dynamics favour employees. The former is not something you can control so, when the market is in this place, you should take advantage of it to propel yourself. However, the former is completely within your control. You can spend some time and effort building a personal brand. Many people discount the value of a brand and the effort spent building one, but it totally works. I have marketing-savvy friends who, since early in their career as juniors, spent a lot of time on LinkedIn thought leadership & brand building. And it totally works. In fact, I have one such friend who was recently part of a restructuring layoff (i.e., not related to performance). Because of the brand they built, once they posted about the layoff on LinkedIn, they had 12 offers within a week all higher than their previous salary.
Another area where you can gain leverage is when you already work at a company that wants to retain you. The only time a business will bend over backwards for an employee is when the conversation is about retention. To make the conversation about retention you need to be completely willing to walk, and your negotiating position is strengthened if you have counter offers. To maintain your political capital (which will be important if you stay) you need to be careful about how you play this game. I've worked with people in the past who approached the business confrontationally, saying "if you don't give me $X, I quit" - that strategy only works once. But there are ways to structure this conversation where you don't leave a bad taste in anybody's mouth.
2. Care about something different than your counterpart
Often the person you're negotiating with cares the most about optimising certain metrics. You should try to spend some time figuring out what those metrics are and see if there is something different that makes a difference in your life.
e.g., your employer might be really under the gun about managing fixed salaries. This is very common in a lot of businesses to try to manage their headcount. So they might be more willing to give you a $50k cash bonus compared to a $25k salary increase. Or maybe they're more open to an extra week or two of vacation vs. salary.
This phenomenon has been really helpful for me in the last year. I run my own business, but my business is fully bootstrapped, so I don't have a board or any investors to please. As a result, I'm not as motivated by ARR as other SaaS companies. Sometimes I encounter customers who would rather pay me a 3-4x one-time fee instead of ARR. By making these deals I immediately guarantee what would have otherwise been four years of cash (potentially with a cancellation risk during the term). A VC-funded SaaS business would almost never make a deal like this, because such a deal would not have a material impact on valuation.
Another example - I was moving recently and sold some furniture. I was chatting with somebody who was an optometrist who wanted to buy a few things, which I listed at $200. They offered $100. I countered, asking for the right to use their employee discount, and ended up getting $500 in value.
So you should also spend some time trying to figure out what your negotiation counterpart cares about. Maybe there is an arbitrage where you can both get exactly what you want, instead of needing to find an outcome where one person wins and the other one loses.
Why would one negotiate on a few hundred dollars when they're apparently capable of negotiating deals worth hundreds of thousands? In my opinion, the marginal benefit does not outweigh the potential downside of being perceived as petty.
The only reasonable conclusion I can draw is that they simply enjoy the negotiation process itself. I guess most of us do not.
That’s an interesting question. I think there are a couple of points here.
So, more broadly, you might be asking me “why waste your time selling $100s of furniture?” which is a completely fair question. The opportunity cost of the time spent selling it was far greater than the benefit I got. From a pure optimization perspective it was a bad use of my time.
But also I just moved to the other side of the world and had an apartment filled with furniture that I needed to get rid of. And I am the type of person who doesn’t like waste, so sending everything to the landfill was misaligned with my personal values. And also I don’t work 24 hours per day, so it’s not like this effort takes tome away from working on the meaningful deals.
It would be reasonable to ask “why not give it away for free?” In my experience, customers that pay you nothing are a much bigger burden than customers that pay you something (and, in fact, I find that higher revenue customers are much easier to deal with on an absolute basis).
And then your more direct question: why negotiate at all? Why not just accept the offer and move on with your life? I think your guess is correct: I am a negotiator at heart. I really truly love the hustle, in all aspects of life. It doesn’t matter whether I’m earning $10, $1000 or $100k: I love making deals. And this part of my character is probably a big part of why I’ve been successful in business.
To your final point - the marginal benefit of negotiating vs. being perceived as petty. In all of these situations the audience is different and their lifetime value is different. It would be foolish to negotiate with a $100k customer over $100s; you’re right to assume that the customer might perceive it as petty (and such a move would probably diminish their lifetime value). But, on the other hand, if you sold something to a random person off Craigslist where their expected lifetime value was in the $100s wouldn’t it be foolish to not try to maximize your outcome, especially if it only added a minute or two to the transaction?
Thanks for taking the time to answer. I think it is valuable to know that some people like this kind of game. Similarly, some people like "making money".
Several people on this forum are confused on why they do not make money, even though they like making products. To an extent, I think the product (and most of its qualities) is irrelevant when you want to make money.
Singapore is a business masquerading as a country. While it is technically democratic, in practice there are some barriers preventing truly free and fair elections. That being said, the leaders in Singapore are not corrupt and truly do focus on what's best for the country. As a result decisions are made quickly, for the greater good, and are not politically driven. The leadership have the latitude to make decisions that they believe will make the country better. Sometimes these decisions don't have a lot of public support (because people are naturally more short-sighted) but, because of the political system, they don't need to rely on public support.
In the case of Singapore, I think this dynamic has led to a compounding effect of good decisions that have put the country in such a strong place today. You see this similarly with Norway's oil fund; it was likely unpopular initially to reinvest so much money into savings, but today it's paying off where they have a $2T savings account, from which they can withdraw up to 3% annually ($60B) for the needs of Norway.
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