• 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

In partnership with

Welcome to March!

Two weeks ago, I was at a car dealership with my fiancée. We arrived at 11 AM on a Saturday and left six hours later with a certified pre-owned car we’d 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, it’s 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.

That’s the unofficial theme of this edition, with other OTF content you know and love sprinkled in. Let’s get after it!

No Negotiating These Highlights:

FATTENING THE WALLET 💰️ 
  • Making Cents of Fighting For Every Dollar

  • Expert Advice from A Former Hostage Negotiator

ELEVATING YOUR BRAND 📈 
  • March Toward Health and Wisdom With This Month’s 2-DO LIST

BOOSTING YOUR PRODUCTIVITY 🚀 
  • Lessons from 100+ Entrepreneurs and Much More in Hustle Hub

Expert Advice 💭

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 week’s advice comes courtesy of Chris Voss, a former hostage negotiator. His book Never Split The Difference has sold more than 2 million copies worldwide.

What’s The Advice?

Let me give you two nuggets taken directly from the book.

“People who view negotiation as a battle of arguments become overwhelmed by the voices in their head. Negotiation is not an act of battle, it’s a process of discovery. The goal is to uncover as much information as possible.”

“To quiet the voice in your head, make your sole and all encompassing focus the other person and what they have to say.”

Back to the car dealership: as we were sitting at the table, I held those two gems in my mind:

  1. Focus on discovery, not battle or rebuttal.

  2. Don’t let your mind wander. Don’t plan what your response is going to be. Listen.

The salesman started with an array of compliments…

  • “You’re getting married? Congrats! This is a big purchase for the family.”

  • ”That’s a beautiful dog. The family is already growing!”

  • “You seem like a nice guy, so I really want to help you out.”

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 it…because we’re not focused. We’re 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 “destination fee” for bringing the car to the lot…despite the fact that the car was already there. (Make it make cents sense 🤣)

Notes I took at the dealership

You could argue this was another motive for his complimentary approach. It wasn’t just because he wanted me to feel good and like him; it’s 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 could’ve easily missed one or more of those nuggets and cost myself thousands.

TL;DR Takeaways:

  1. The top priority is learning (discovery).

  2. To ensure #1 is properly valued, listening is key. You should give the person opposite you your undivided attention.

  3. 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 💰️ 

Negotiation = More Money in Your Pocket

Short and Sweet: Every dollar you negotiate is a dollar that stays with you. Who wouldn’t want more dollars?

Whether it's trimming unnecessary fees, questioning hidden costs, or simply asking, “Can we do better on this price?”— negotiation is one of the easiest ways to SAVE. The trick? Stay patient, listen closely, and never be afraid to challenge what’s put in front of you.

Q&A TIME:

Why should I negotiate, even if it’s just a small amount??

  • Because small wins add up. The dealership tried charging me a destination fee for a car that was already there. That’s a charge I could’ve blindly accepted. Instead, I pushed back and saved.

How do I know what’s actually negotiable??

  • Everything is negotiable. If you see an extra or curious charge, ask if it’s required. They have to tell you the truth, and then you can make an informed decision.

What’s 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, “Your website says one thing, but this listing on Carfax (which is a partner of yours) says another. You need to match this number.” Use whatever research you’ve done to your advantage.

What if I don’t like confrontation??

  • You don’t have to argue — just be curious. When I spotted a small issue in the trunk, I didn’t demand a discount. I simply asked, “How are you handling this?” 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, “This is just how it is.” But the reality? Many costs are inflated...until you push back. That’s why negotiation isn’t about winning — it’s about discovery and listening to what’s being relayed to you.

So the next time you’re making a big purchase, don’t 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 📈

YOUR SUCCESS:

Get Negotiating - Let’s wrap this up with data-driven perspective from a Wharton professor’s award-winning negotiating class.

THEIR SUCCESS:

Get Inspired - There are many reasons to start your own business. One that’s under-discussed? The impact you can have on your community. Check out this recent article from Visual Capitalist that backs up the claim “America’s entrepreneurs keep the job market ticking.”

YOUR SUCCESS:

Get BONUS EXPERT ADVICE - Business and leadership lessons from more than 100 successful entrepreneurs!

2-DO LIST 💡 

March

  1. Learn About (and From) The Past - Sunday was “Read Across America Day,” 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 it’s the perfect month to take a break from your usual reading habits and digest some history. Not sure where to start? Here are the “most anticipated” history books of 2025, courtesy of Barnes and Noble.


  2. Commit to Your Healthiest Month Yet - March is also “National Nutrition Month.” With spring on the horizon, there’s no better time to begin (or re-commit) to your health and fitness goals.

Here’s 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 – far below the recommended 10-15x for real security (especially with dependents). Term life insurance can bridge the gap with customizable, affordable plans. Money’s 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, we’ll be back with March’s Personal Branding Edition, featuring Cool Communicator, A Networking Hack you can take with you anywhere, and much more!

Community Poll 📊 

What's The Best Social Media App That You Use?

Login or Subscribe to participate in polls.

Last Week’s Poll Results:

Do You Normally Get 7+ Hours of Sleep??

  • YES - 100%

  • NO - 0%

As always, see you next Tuesday 🤝 

Find me on LinkedIn & Instagram

You are now On The Fly & In The Know.