Updated December 7, 2023

How Brandon Turned A Condescending Client Into A Happily Paying Customer And Increased His Revenue By 525% – In One Meeting (In-Depth Case Study)

“We’re completely stuck. I don’t see how we can make it work,” wrote the COO.

Brandon (name changed) had been negotiating with this client for two years.

And he was at risk of losing them because the COO felt “stuck” – all after Brandon had put in 100 hours of unpaid work.

And you know what the strange thing is?

This was an exceptionally lucrative deal for his client – at minimal cost, with minimal risk.

How much do you think their profits would skyrocket?

$750.000 per year.

So why wasn’t Brandon able to close the deal (even after two years)?

  • What held his client back from implementing the solution?
  • Why was Brandon unable to convince the COO?
  • And how did he finally manage to close the deal?

That’s what we'll talk about in this negotiation case study.

The Client

Brandon’s client has 20 trucks and they wanted to optimize their delivery routes.


Because every kilometer they don’t drive saves them $2.50.

This is HUGE for this company - driving millions of km / year.

The problem?

There are billions of possible route combinations, and it’s humanly impossible to find the most efficient one.

This is where Brandon comes in:

His startup offers an AI-based system that narrows it down from billions of options that “could look good in theory” to the 5 or 10 options that actually make sense.

With this in mind, let’s look into how he got the COO excited in the first place:

Everything went well in the beginning

Brandon’s startup has two types of services.

The first one is about analyzing and strategizing the routes.

That means:

The software collects data, uses it to plan routes in advance and makes simulations.

That’s what they did:

They collected 2 months' worth of data, compiled it, and cleaned up all the errors.

For example, stuff like:

  • The address entered into the “delivery address” data field was the invoice address.

Now, I’m writing this very “lightly,” but cleaning up these kinds of data errors is a TON of work.

And for all this work, Brandon had given the COO a 50% discount.

It took roughly 100 hours, but he only charged 50 hours (= $5,000).

Based on the AI suggestions, his client could see that the improvements would be massive.

For example:

  • Create various “delivery regions” (per truck)
  • Change the delivery frequency in each region (daily, every other day, or twice a day)
  • Change the route patterns (order of delivery points)

So, Brandon had hooked the COO. 

And then he got him excited about his second, more advanced product:

Real-time optimization

The simulations can already be used to optimize the delivery routes.

But it’s better to use the software in real-time.


Because deliveries change fast in the real world.

There is no fixed daily or weekly schedule for

  • what products need to be delivered, 
  • to whom, 
  • at what time.

So, every morning is a “different story.”

That means:

To really maximize efficiency, every morning at ~3 AM, you need to create a “real-time” solution.

Similar to the strategic analysis, but automated and MUCH faster!

Now, here’s the challenge:

The software only works if:

  • The cleaned-up data stays clean.

    This is much more difficult because this requires training everyone who enters data to do it correctly:

    Truckers, route managers, the head of logistics, and the COO.
  • Implement a real-time connection to the client’s resource planning system (API + some coding + testing to fix errors)

You can see: it’s a lot of legwork.

The real-time optimization deal details:

They agreed on a software user license.

$100 per truck per month (= $2,000 per month).

What does the client get?

Based on the first analysis, they would save a conservative ~25,000km per month with Brandon’s software.

Which equals to $62,500 in savings every month.

Saying that this is a sweet deal is an understatement.

The only extra fee Brandon required at the beginning was another $5,000 for the trainings and system integration.

Note: at this point, the COO had not yet paid Brandon the first $5,000 yet, but already ordered the real-time optimization.

That’s when things started to go downhill.

Things started to go downhill from there

Demand #1: A 3-month free trial

Brandon accepted it as a loss leader.


  • He’d been working on building this relationship for two years.
  • He was looking forward to regular payments from the 4th month onwards.

But his startup would lose $6,000 (not earning = losing).

Demand #2: “We don’t need you to train our people to use this system; we will do that ourselves.”

That was the next line the COO hit Brandon with.

Brandon’s response:

“That will be quite difficult for you.”

"A very cool-headed, factual reply, considering the hard negotiation tactics the COO was using.

Let’s face it:

At this point, Brandon could have said, “You cheap bastard,” or simply: “Gimme a break.”

But he’s a calm, patient negotiator who doesn’t let emotions get in the way of good results."

Completely underestimating the workload

The COO was very direct:

“We can handle it. We are not willing to pay $5000. It can all be done in 2-3 hours once the connection to the planning system is set up.”

Now this is a remarkable level of wishful thinking.

And you know what the crazy part is?

The COO still expected to be able to reach Brandon and his team daily for problem-solving.

But it gets even better:

The COO went on vacation for two weeks in the first month of the trial period, leaving his team leaderless during a tough transition time.

Can you see how irrational that is?

  • The COO could have easily gotten the money back five-fold within just one month of using Brandon’s software.
  • But still, he was not willing to pay the $5,000 for training and integration support.

They were able to do nothing

In the first month of the 3-month free trial, the client was able to do nothing.

They completely depended on Brandon and his team, who were supportive, but not “all day, every day,” since the COO had denied them the $5,000 training fee.

That’s when Brandon received an email from the COO.

The COO was ready to give up

“We’re completely stuck. I don’t see how we can make it work.”

The COO was ready to end the project.

So, Brandon was at risk of losing this client (having been paid nothing because “it won’t work” and investing two years into building the relationship).

You see how this client sabotaged themselves out of a fantastic deal, right?

But why?

Brandon was more than frustrated at this point.

But, not ready to give up on this client, he said:

“We know how to make it work. Give me one meeting.”

At this point, Brandon contacted me to give him a 1-on-1 coaching session.

Brandon’s usual negotiation experience, until now

In his own words:

  • my mind is racing and I’m computing while I’m talking
  • I feel robotic
  • emotionless

He also said that this style allows him to negotiate well with some people.

But not with his ideal clients.

So he wanted to adapt his style.

But how?

Brandon’s hidden weakness

He only tried to convince the COO with the classics:

  • Facts and figures
  • Discounts
  • Extreme cost-performance ratio

But he missed one key component in his strategy for dealing with the COO.

He needed to dig a bit deeper.

Where did the COO’s resistance come from?

Do you see how irrational the COO’s refusal to buy was?

Brandon made a variety of mistakes, but one stands out in particular.

By focusing on the rational, professional parts of the negotiation, he ignored the emotions driving the COO’s behavior.

And emotions drive purchasing decisions.

So what did the COO feel?

He felt superior to Brandon.

So he treated him like a lord treats his butler.

  • He showed no appreciation for Brandon’s work. 
  • He pretended it was easy (“we can do that ourselves in 2-3 hours”).
  • He demanded more and more and tried to squeeze every last drop out of Brandon (3-month free trial).
  • He deliberately created a hierarchy gap.

This is a defensive counterattack move, but why does the COO even go there?

Here’s the tricky part:

Brandon made the COO feel unappreciated, too - but without wanting to.

He unintentionally hurt the COO’s sense of status and professionalism.

Think about it:

  • The COO has been doing his job well and worked hard for 25 years.
  • He fought his way to a leading role in the company.
  • Tried every smart efficiency measure to get his workforce to perform at their best.

And here comes little Brandon, a kid just out of college, and says:

“Let’s get you up to speed, Grandpa, and bring your team into the 21st century.”

(Of course, Brandon didn’t say that, but that’s what the COO felt.)

From that background information, I created my version of the COO.

I role-played telling Brandon what I suspected the COO was saying between the lines:

  • "You young app developers haven't got a clue about the realities of my business, about life, or about how the world works."
  • "So, you've got a cute app. Fine, I'll give you a chance. Don't mess it up."
  • "Have you ever driven a supply truck? It's not Disney World, kiddo."

At this point, it's not important whether what I said was 100% accurate.

It was all about emphasizing the COO’s feelings.

Sure, Brandon had felt something was off when speaking with the COO.

But he couldn’t put his finger on it.

And he wanted to ignore it.

Because he judged feelings as something unprofessional that just “gets in the way.”

So, I portrayed the COO in a way that forced Brandon to look at the COO’s emotional resistance.

Suddenly, Brandon saw the obvious power play - and where it came from.

The question was:

How could Brandon get the COO to stop those power plays, but without damaging the relationship?

That’s where the emotional roller coaster technique comes in:

The Emotional Roller Coaster Technique

Three conditions for this technique to work:

  1. An established relationship.
  2. A moment when the other person is vulnerable and has shown a weakness (for example, the COO’s admission in the email that they couldn't make it work).
  3. You have to be willing to show negative emotions without feeling them.

This is NOT a one-size-fits-all technique, and it’s risky if you get it wrong.

So if you’re not sure whether it’ll work for you, tell me your situation in the comment section.

Here’s how it works:

Step 1: Drag ‘em down

Strongly criticize your counterpart’s mistakes.

Be confrontational, but keep it short: 90 seconds max.

Because you don’t want to get dragged into an argument.

Your counterpart should be shocked at the way you’re speaking to them. 

And before they can recover from that shock, you’re already moving to step 2. 

Here’s how Brandon handled step 1:

In their next meeting, after hellos and short small talk, he made his move.

He started by asking: “So, you feel stuck, right?”

COO: “We are stuck.”

Brandon: “And you thought you didn’t need our help. You said that.”

COO: “It should have been an easy integration.”

Brandon: “And you really thought you could just take a 2-week holiday at the very beginning of a major new process implementation. Seriously?”

COO: “A good team needs to be able to function without their COO for 2 weeks.”

Brandon: “I told you they’d need training, and you left them leaderless in a difficult time. Who did you expect to pick up your slack for free?”

The COO’s eyes went wide. 

Brandon could see the shock.

He didn’t wait for an answer because it’s not about getting an answer.

It’s about creating the emotion.

Then Brandon moved to step 2:

Step 2: Build ’em up

In this step, you show your counterpart the way out.

Calmly, compassionately.

That’s why you need to show confrontation in step 1, but without feeling it:

If the first 90 seconds got your pulse racing, it’s much more difficult to be calm and compassionate in step 2.

And this calm compassion makes all the difference.

It not only calms down your counterpart’s brain but also shows that you are 100% in control.

Here’s how Brandon handled step 2:

“Look, we can salvage this situation. In fact, you’ll still earn plenty from it, even now.”

And explained to the COO how he wouldn’t even charge him, at all.

Only take a cut of the eventual savings.

“Every kilometer you save, that’s $2.50. $2 for you and 50 cents for me.”

At which point, the COO, a seasoned negotiator, laughed and said:

“I see what you did there.” (referring to Brandon’s way of putting on pressure.)

And added: “Ok, it’s a deal. I’ll give you 6 months to make it work.”

Now if you’ve been paying attention, you’ll note that this deal increases Brandon’s take from

$24.000 → $150.000 / year

Not bad.

Especially when you consider he actually stood on the verge of getting NOTHING.

Let’s quickly recap:

  • Brandon had a fantastic deal for his client.
  • He proved (rationally) that it works through his analysis at the beginning.

So why was he not able to get the final “go” on this project?

Because facts and figures don’t make people buy. 

Emotions do.

And it’s the emotional component that most people can’t wrap their heads around.

But Brandon did.

And he made the sale.

Are you a startup founder stuck in a sales negotiation like Brandon?

  • Have you been negotiating a deal for weeks or months but have been unable to close it?
  • You can’t figure out what’s causing your client’s resistance?
  • You want a clear and actionable plan?

Check out my close-the-deal 1-on-1 coaching, in which I’ll show you exactly how to flip the switch to “buy.”

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