The only time you can afford to have this behaviour is when you have leverage over the other party either by connections, dependencies or assets. People often forget that without leverage being rude will get you nowhere. Try this at work tomorrow and I bet you in no time your manager will show you the door. If both parties are on equal terms when it comes to negotiation power then it will either turn into a pissing contest or gets resolved quickly.

I often think that bullies get a lot of perceived leverage. They may not have real leverage but they intimidate people.

Once word gets around though, it starts to harm you in the long run. I worked for a company where one of the owners seemed to have a world view that everyone is trying to screw you over, so you better screw them over first.

After I left I had a friend ask about the company, because they were about to a deal with them. I gave my honest opinion and suggested they be sure to get any money up front and be very careful to reduce their risk.

I am not so sure about that. When I was consultant I had several clients that were a complete pain to deal with but they also had a lot of money to spend so it was worth it in the end. When I read business biographies I get the impression that a lot of successful people/companies like Gates, Jobs, Ellison or Walmart are really hard to do business with. They will exploit you as soon as you make the slightest mistake but if you play everything right you can make good money.

I would advise never to do business with Walmart, Apple, Microsoft as a small business. They have so much leverage over you, mistake or not things are out of your control from the start. The more work you do for them the more they take over the rest of your business. Get bigger then talk.

If the monopolist is huge enough, they control an enormous cascade of wealth transfer.

There are many points for a small business to tap into one or more of their streams in a way which everybody wins. But this usually requires that no disruption takes place. Without actually adding value (to natural resources) yourself, you are allowed to remove enough value to grow an operation having share price which can outperform the underlying monopoly.

This is a common strategy with oil & chemical companies.

They can also afford to not be a pain or make you wait until the end to be financially worth it.

This kinda seems like a just world fallacy. It might get around, it might not - I'm not sure its really known either way. But we like to hope people that regularly behave like assholes eventually get punished for it.

I've encountered two types of people who attempt the asshole strategy: A) those stick around in town and after about 10 years, eventually build a bad reputation that they can't shake, and B) those who have to move every 2 to 3 years to keep ahead of their bad reputation.

The first group finds they eventually have to move to get back to progressing in their career (hopefully learning from their mistake). I've known guys who moved and did change, running into them again and finding them to be completely different people, settled into family life, and quite happy. I've known guys who moved and didn't change, found themselves needing to move again in 10 years, all while cursing the world for being against them.

The second group just never progresses in their careers. You see them try to move into positions that seemingly fit such behavior, like "serial entrepreneur" or "SEO consultant". They never really grow, always behaving like they're still in their early 20s. By the time they hit their 40s, they can't pick up chicks at bars anymore and it hits home that they've wasted their life. Unfortunately, I've never met anyone who changed and turned it around.

It does come around. It just takes longer than internet scale time.

It does surely go around often. It also looks like it doesn't often (but this one is a negative, so one can not be sure).

No alternative is rare, so the ratio is the interesting measure. (And no, I don't know this one.)

>Once word gets around though, it starts to harm you in the long run.

Does it? It seems to have worked for the president of the USA just fine and that was his exact tactic in all of his business "deals".

> Once word gets around though, it starts to harm you in the long run.

How sure of that are you? One of the big proponents of this strategy is currently President of the United States.

> A lot of people will give in just to keep the peace.

IME it works only if the party is the only way in town and negotiation is only on scope and price (i.e., the other party cannot take their business elsewhere). Otherwise they get known as "assholes not to deal with" which is a very hard thing to shake off. My 2c.

> It’s a common negotiation strategy to be a complete ass and wearing people down. A lot of people will give in just to keep the peace. It also works to ask for more concessions right before closing the deal. You just have to be shameless. I think that’s why sociopaths tend to do well in business.

For lawyers, at least, this might work...once. The second time they try it, you know there'll be no "give" in "give-and-take", so you're not afraid of going in for trench warfare. If they're assholes through-and-through, it's not unheard of for party B to ask party A to switch lawyers.

It's an excessively short-term view of "winning", and it doesn't benefit anybody in the long run.

Source: former corporate lawyer.