- On The Fly
- Posts
- #109 Negotiate More...Make Every Dollar Worth It
#109 Negotiate More...Make Every Dollar Worth It
Plus: Business and Leadership Lessons from 100+ Entrepreneurs

Welcome to March!
Two weeks ago, I was at a car dealership with my fiancĆ©e. We arrived at 11 AM on a Saturday and left six hours later with a certified pre-owned car weād found online the night before.
It was exhausting both mentally and physically. Sitting around all day and going back and forth on pricing can get to you. Seriously, itās a pain in the you-know-what.
But it was also incredibly satisfying, not only because I got the vehicle I wanted at a price I could stomach, but also because I achieved that goal using negotiating advice from one of my favorite books.
Thatās the unofficial theme of this edition, with other OTF content you know and love sprinkled in. Letās get after it!

No Negotiating These Highlights:
FATTENING THE WALLET š°ļø
Making Cents of Fighting For Every Dollar
Expert Advice from A Former Hostage Negotiator
ELEVATING YOUR BRAND š
March Toward Health and Wisdom With This Monthās 2-DO LIST
BOOSTING YOUR PRODUCTIVITY š
Lessons from 100+ Entrepreneurs and Much More in Hustle Hub

Expert Advice š
Never Split the Tab Difference.
For our new readers out there, this section regularly features words of wisdom from successful entrepreneurs, authors, psychologists, Fortune 500 CEOs, and anyone we might reasonably deem an expert to give you fresh perspectives applicable to your personal and professional growth.
This weekās advice comes courtesy of Chris Voss, a former hostage negotiator. His book Never Split The Difference has sold more than 2 million copies worldwide.

Whatās The Advice?
Let me give you two nuggets taken directly from the book.
āPeople who view negotiation as a battle of arguments become overwhelmed by the voices in their head. Negotiation is not an act of battle, itās a process of discovery. The goal is to uncover as much information as possible.ā
āTo quiet the voice in your head, make your sole and all encompassing focus the other person and what they have to say.ā
Back to the car dealership: as we were sitting at the table, I held those two gems in my mind:
Focus on discovery, not battle or rebuttal.
Donāt let your mind wander. Donāt plan what your response is going to be. Listen.
The salesman started with an array of complimentsā¦
āYouāre getting married? Congrats! This is a big purchase for the family.ā
āThatās a beautiful dog. The family is already growing!ā
āYou seem like a nice guy, so I really want to help you out.ā
Sure, all of these compliments felt great, but we all know the motivation behind it. Salespeople will say anything to close a deal, and sometimes, we fall for itā¦because weāre not focused. Weāre not listening (and paying attention to expressions, body language, etc.) with intent. Because I was present the entire time, I never fell for his tactics.
Instead, I was locked in on the relevant information, which was:
There was a small issue with the trunk.
There was a discrepancy between their price and the Carfax price.
There was an optional add-on included in the base price that I was not obligated to pay for.
There was a ādestination feeā for bringing the car to the lotā¦despite the fact that the car was already there. (Make it make cents sense š¤£)

Notes I took at the dealership
You could argue this was another motive for his complimentary approach. It wasnāt just because he wanted me to feel good and like him; itās possible he was trying to distract me from this important info that, in the end, would save me a lot of money. This is what I discovered while listening intently. Reflecting on it after leaving, had it not been for my focus, I couldāve easily missed one or more of those nuggets and cost myself thousands.
TL;DR Takeaways:
The top priority is learning (discovery).
To ensure #1 is properly valued, listening is key. You should give the person opposite you your undivided attention.
Read Never Split the Difference by Chris Voss if you want to learn how to squeeze every last penny out of each negotiation you take part in.
MAKING CENTS š°ļø
Negotiation = More Money in Your Pocket
Short and Sweet: Every dollar you negotiate is a dollar that stays with you. Who wouldnāt want more dollars?
Whether it's trimming unnecessary fees, questioning hidden costs, or simply asking, āCan we do better on this price?āā negotiation is one of the easiest ways to SAVE. The trick? Stay patient, listen closely, and never be afraid to challenge whatās put in front of you.
Q&A TIME:
Why should I negotiate, even if itās just a small amount??
Because small wins add up. The dealership tried charging me a destination fee for a car that was already there. Thatās a charge I couldāve blindly accepted. Instead, I pushed back and saved.
How do I know whatās actually negotiable??
Everything is negotiable. If you see an extra or curious charge, ask if itās required. They have to tell you the truth, and then you can make an informed decision.
Whatās the best way to get leverage in a negotiation?
Information. I compared the Carfax price with theirs and noted the difference. That gave me the confidence to say, āYour website says one thing, but this listing on Carfax (which is a partner of yours) says another. You need to match this number.ā Use whatever research youāve done to your advantage.
What if I donāt like confrontation??
You donāt have to argue ā just be curious. When I spotted a small issue in the trunk, I didnāt demand a discount. I simply asked, āHow are you handling this?ā That one question opened the door to them rectifying the problem. Before you knew it, I was signing a document acknowledging that they were obligated to fix the issue. Ask those questions.
O.T.F.
O.F.T - One Final Thought

Most people accept prices at face value. They assume, āThis is just how it is.ā But the reality? Many costs are inflated...until you push back. Thatās why negotiation isnāt about winning ā itās about discovery and listening to whatās being relayed to you.
So the next time youāre making a big purchase, donāt just sign on the dotted line. Slow down. Ask questions. And remember: every dollar you negotiate is another dollar that stays in your bank account.

HUSTLE HUB š
YOUR SUCCESS:
Get Negotiating - Letās wrap this up with data-driven perspective from a Wharton professorās award-winning negotiating class.
THEIR SUCCESS:
Get Inspired - There are many reasons to start your own business. One thatās under-discussed? The impact you can have on your community. Check out this recent article from Visual Capitalist that backs up the claim āAmericaās entrepreneurs keep the job market ticking.ā

YOUR SUCCESS:
Get BONUS EXPERT ADVICE - Business and leadership lessons from more than 100 successful entrepreneurs!
2-DO LIST š”
March
Learn About (and From) The Past - Sunday was āRead Across America Day,ā which emphasizes the importance of literacy. Couple that with the fact that there are numerous important historical dates in March (on this day in 1789, the first-ever meeting of Congress under the Constitution took place), and itās the perfect month to take a break from your usual reading habits and digest some history. Not sure where to start? Here are the āmost anticipatedā history books of 2025, courtesy of Barnes and Noble.
Commit to Your Healthiest Month Yet - March is also āNational Nutrition Month.ā With spring on the horizon, thereās no better time to begin (or re-commit) to your health and fitness goals.

Hereās why workplace life insurance might not be enough
Unexpected events shouldn't leave your loved ones financially exposed. And while employer coverage is a nice perk, it usually only offers 2x your salary ā far below the recommended 10-15x for real security (especially with dependents). Term life insurance can bridge the gap with customizable, affordable plans. Moneyās Best Life Insurance list can help you find coverage starting at just $7/month, providing the peace of mind your family deserves.

Before You Go!
Thank you again for joining us for another edition of OTF!
Next week, weāll be back with Marchās Personal Branding Edition, featuring Cool Communicator, A Networking Hack you can take with you anywhere, and much more!
Community Poll š
What's The Best Social Media App That You Use? |
Last Weekās Poll Results:
Do You Normally Get 7+ Hours of Sleep??
YES - 100%
NO - 0%
As always, see you next Tuesday š¤


You are now On The Fly & In The Know.

