The only reasonable conclusion I can draw is that they simply enjoy the negotiation process itself. I guess most of us do not.
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?
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.