I think it’s important to ask. This is hard for me too, but the worse that they can do is say no, or reject your offer. Again, the worst that they can say is no, and words are very cheap. Literally, you move your mouth, and spew out a few words, and go from there. At the very least, if they say no, don’t you gain information on what you could have worked on? It’s all good practice and sometimes the stakes are so low that you should go for it.

Kind of unrelated, but when my dad taught me the basics of tennis, this is what he told me:

Do not give a shit about where the ball going outside the tennis court. Don’t worry son, I’ll pick it up. NO WORRIES. HIT THAT BALL AS HARD AS POSSIBLE. IT’S OK IF IT IS OUT OF BOUNDS.

I recently got to go home and play with him, and it made sense! You want to push yourself and hit the ball as hard as possible, so you know your limits. Similarly, throw a couple of words out there and see what sticks.

Here are a couple of stories where I’ve had some success. And also failures:

Insurance Claim

I once called up to file an insurance claim, where the estimate seemed to be significantly lower because of how they calculated the amount for the claim. I told them that their method seemed flawed, and within then minutes they raised my claim amount by $500. So within 10 minutes I was able to save $500.

Internet Bill


Last year, their promotional rate was at $40 dollars a month. However, since we’ve been in their service for a year, they decided to hike the rate to $63 dollars a month. So I called them up the first time and threatened to switch to an alternate service provider. And they told me that the best they can do is to lower my rate to $53 and told me to get lost.

I accepted and a month later, I saw an ad for an alternate service for $40 dollars a month. I called my ISP once more, and told them unless they were willing to lower my rate, I would be switching. And that I just got off the phone with the other ISP(which is true, I was fine with pulling this trigger)

They put me on hold and 10 minutes later came back with $43, which I accepted.

I’m happy they did this. I could now avoid staying at home and monitor the service man setting up internet!

In the grand scheme of things, this 20 dollars isn’t much. But in terms of absolute savings percentage wise, it’s closer to 30%. It leads me to wonder - how many opportunities and things are we missing out, just because we’re a bit afraid to be a little more assertive, and ask?


However, the following year, they jacked up the prices again. I lowered it by 5 dollars, but didn’t have the strength to dance between them. Plus, my parents might end up making the move, so I wasn’t sure if I could aggressively bluff and say that we’re going to switch to another provider since the other provider requires a 2 year contract. Maybe I’ll take another stab next time I’m home.

Job Negotiation

OK, this is the one where I bricked. But it’s fine, I learned a hell of a lot from it.

Basically, I got a job offer, and the starting salary was a lower than expected. I gave the recruiter a legitimate reason why my salary should be increased. But I asked for too much - way too much considering the original amount. He told me to take the original offer or leave it.

I called them a day later, and asked again. But this time, I talked to the company I was contracting part time and they were considering bringing me full time when I told them I was about to accept a full time job.

When I told the first recruiter about this, I suddenly noticed a chance in the tone of his voice. He became very interested in what the other company was offering. But I didn’t have any concrete numbers, and I wasn’t willing to bet on losing the first job offer, so I screwed up and played the situation wrong. The best he said was he could move it up 5k. I got tired of playing the game and was in a bit of a rush so I said I’ll take the original offer. In retrospect I should have pushed for that 5k. Sure, 5k is nothing but a couple of dollars per week and it’s not a lot on a grand scale of things. But if it’s such a small amount, then why shouldn’t you have it as well?

I learned two things: First, it’s always good to have alternatives and a counter-offer. I think this is fundamental. It shows that you have an out, and are desirable. Without this so called alternative, I don’t think any company would budge on their price or be flexible.The jump from 1 to 2 offers is huge, and the minute you have 2 offers, you signal there is competition for you!

Second, if the recruiter said something like, “Hey Mr. Panda, I think the most we can do it 5k. But I’m not sure. Let me do my best and get back to you.” IF he got back to me and said something like, “I’m really sorry panda man. I couldn’t get the management to approve 5k, but I fought hard and got us 2k!” If he did that, I’d think - man this guy is great. And if I knew any other friend that was interested in joining this company, I’d hook this guy up even if I left. So - he’s playing the short term game, and that’s fine by me.

If you can’t meet their initial demands, you should partially meet some of their demands. They’ll appreciate you for it.

It’s also said in the Book of Proverbs too - if a friend comes to you asking for an absurd amount of money, and you turn him down, the friendship is dead right there. Same thing happened with a distant family relatives. Their relationship never fully recovered.

Instead of doing that, meet their demands to the best of what you think is reasonable. Something like, “Hey, I really can’t give you the amount you’re asking for. But I can give you this much - no strings attached. Don’t have to pay me back.Hopefully it all works out pal.” You save your friendship because at the end of the day you still helped!

So yeah, I’m not going to be recommending that recruiter, or have a high opinion of him. His loss.

Gym membership

I went to a boxing gym workout at Gleason’s Gym in Brooklyn, and the owner said it costs $50 dollars to train per week. I went up to him and asked him for a discount. He asked me for a number, and I gave him $35. Thought it was reasonable since the group lesson was a bit pricy. He was down with it, and I got myself a discount. Ask.

Eye Exam Bill

I got charged $250 for an eye exam. It was ridiculous. They didn’t even get me conclusive results after the exam - they referred me to another hospital. I got another bill from the other hospital, and they charged me $178. I thought this was reasonable, so I didn’t call them up fighting for more dollars. I could have, but I felt like the price was fair.

Anyhoo, I didn’t think the first $250 exam was fair. I sent them an email, saying how I enjoyed being at their establishment, how they’re doctors were nice. They were. But I told them I had a problem with their bill, and I couldn’t recommend them to my friends or leave a honest to God positive review. I told them that the fair price for the exam should be $150.

They called me and said they’ll refund me $100. I thought this outcome was reasonable, considering that I didn’t have any powerful leverage. The transaction was already done, and it was more of a courtesy. That or they care about their long term prospects and online reviews.

Yet another tangent, but here’s what would be an interesting experiment. I go to a ton of stores, and try is variations of the above sending different emails to lower the original invoice. So maybe I should only mention reviews. Maybe I should not have started out with the compliment. Or maybe I could vary the extravagance of compliments. It would be fascinating to quantify the effects of what I’ve written and see which strategies are most effective to reduce costs.


Here are a few key takeaways:


I read this from a book. It’s an amazing exercise. Here we go: Imagine a person you hate. You can’t stand this person. You want to hurt them…

Now that person is asking you do pay you loan you some money.

Will you do it?


The principle behind this exercise is that - if you hate the guy, then you will not help them out. Similarly, if the other party hates you because you’ve been rude, and selfish, they will not help you. At a fundamental level, they have to like you to match your demands. I think this is key. The more they like you, the more they are willing to help you out.

Consideration for the Other Party

If you throw out a number that will screw over the other party and treat them as an idiot, they will not be kind to you. They will not like you. In fact, they might end up hating your guts. So for example, if you know that a price good is $100, and offer them $10, you are downright insulting their intelligence. People on eBay do this shit all the time, and it ends up just pissing me off. Because it’s insulting my intelligence. Why?!

Have some consideration for the other party.

Last updated 8/9/19, originally drafted 03/01/2018.