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Boss Gave A Huge Discount To A Rich Client, Instantly Regretted It

by Annie Nguyen
November 4, 2025
in Social Issues

Pricing strategies in commission work often balance foresight with flexibility, especially when supply chains signal trouble ahead.

A department manager crunched the numbers last fall, factoring in warnings from vendors about shortages and hikes, then set bids to secure a modest profit margin. Most clients accepted the adjustments without fuss, recognizing the value in quality and speed.

One affluent regular pushed back hard on a major project, leveraging past deals and threats to shop elsewhere. The owner overrode the manager’s calculations, demanding cuts to match lower-grade rivals.

Invoices arrived months later, devouring nearly the entire payment before labor even entered the equation. Scroll down for the boss’s stunned reaction, the quiet reminder of ignored alerts, and Reddit tales of billionaires who still haggle over pennies.

A forward-thinking manager raises prices for looming inflation, but the boss slashes them for a whining VIP, forcing the project to be done at cost or worse

Boss Gave A Huge Discount To A Rich Client, Instantly Regretted It
Not the actual photo

Dont want to heed my warning about giving Deep Discounts to Wealthy Clients?

I work for a company that does commissions for clients.

I am the manager of my department.

This comes with a number of responsibilities, one of them is bidding on work.

Last fall I evaluated the current global situation

and how it would be affecting the costs of our supplies

and possible shortages as well as inflation.

As a result, I priced a few of our pieces of work

to help prepare us for the price increases I had predicted,

giving us an 8–10% profit upon completion.

A well-known client came in and contracted us

to do a rather large and time-intensive project.

This individual is very well off and is in no way in any danger of going broke any time soon.

However, this client complained about the new prices.

He had contracted us in the past on certain items and wanted the same work done again,

but seeing the new price, he complained to the boss and threatened to go elsewhere.

The owner, my boss, decided I had priced the work too high

based on the complaints of this one customer.

(Previous customers had not batted an eye.)

Boss asks me to adjust the price down to be the same as the "competition."

Just so you know, the competition does not carry the same quality standards

and often has a 2–3 year turnaround.

I explained this to the boss, that my numbers were based on the increases

from suppliers and subcontractors, who I speak to regularly.

These companies we work with warned me beforehand

about what was coming, and I took it all to heart.

I had passed the warning on to the boss at the time,

but it appeared he blew it off or forgot about it,

and at the time of making the new price list, he didn’t complain.

It wasn’t until this one, somewhat well-known local client raised a stink

that he decided to bring the issue up with me.

So Boss insisted that we should be pricing lower to keep up

with the competition or we would lose this customer.

Of course I argued that it would hurt us in the long run

and all we would be doing is attracting tire-kickers.

He stood his ground though, and I didn’t have the energy to fight him on it.

So in the end, he’s the boss and got what he wanted.

So the time came to order the supplies and pay the subcontractors.

The costs of these materials as well as the work done on them

were 90% of the price Boss had agreed to with the customer.

This is before my own labour costs were factored in.

Boss sees the bill and gets really upset and asks me

what the customer was paying to have the work done.

I gently reminded him this was for Rich Tire Kicker Customer, and I had warned him well beforehand.

But because he wanted to retain Rich Tire-Kicker Customer,

he got what he wanted, but the company did the work at cost,

and perhaps more with my labor factored in.

Boss later came to me and asked me to make up a new price list.

I told him I didn’t need to, I did that last fall,

and as long as no one gives deep discounts, we will be in the green. He’s listening to me now.

Discounting services for affluent clients to undercut perceived competition often erodes profitability, especially when informed pricing accounts for rising costs.

In this department manager’s experience, forward-thinking bids incorporated supplier warnings about inflation and shortages, targeting 8–10% margins.

Yet, the owner’s intervention, slashing quotes for a high-profile, financially secure customer, reduced the project to break-even or loss once materials hit 90% of revenue, excluding labor.

This validates the manager’s caution: selective concessions attract price-sensitive buyers while alienating those valuing quality and timeliness.

Pricing strategy experts stress aligning rates with value delivered, not rival undercutting.

According to a Harvard Business Review article, relying on reactive discounts can undermine a firm’s value positioning and erode long-term pricing power. Maintaining premium positioning and limited discounting helps protect margin integrity.

Similarly, the Professional Pricing Society advises cost-plus models incorporating subcontractor forecasts, as ignored in this case, prevent margin compression, evident when actual invoices shocked the owner. Supply chain disruptions amplified the misstep.

A recent McKinsey analysis of the materials industry highlights rising price volatility across supply chains and custom-manufacturing sectors, showing how early cost alerts and proactive strategy moves by managers can build operational resilience.

The owner’s oversight, dismissing warnings until bills arrived, exemplifies confirmation bias, where client complaints override data. For managers, documenting rationale via email or memos creates accountability trails, shielding against reversals.

When overridden, compliant execution with gentle reminders, like quoting prior discussions, fosters learning without confrontation.

Owners benefit from delegated authority on bids, coupled with quarterly reviews tying discounts to metrics: require approvals only if below 15% margin, per Deloitte’s governance frameworks.

To rebuild, revise contracts emphasizing fixed pricing amid volatility, notifying clients of adjustments. Train sales on value articulation, highlighting superior standards and faster turnarounds, to deter tire-kickers.

This incident transformed skepticism into deference; sustained listening ensures viability. Ultimately, equitable pricing sustains operations, rewarding expertise over expediency.

Wealthy clients, capable of full rates, respect firms that uphold them; discounts breed entitlement, not loyalty.

Check out how the community responded:

These Redditors share tales of billionaire clients or key accounts getting kid-glove treatment, losing money to “keep” them despite no real flight risk

ThatHellacopterGuy − Billionaire helicopter clients demand excessive documentation,

yet the company fears losing them and undercharges, resulting in near-zero or negative profit.

BlueFootedBoobyBob − Complains about bosses underpricing for massive corporations

but charging full for small clients; follow-up contracts rarely come.

RockNRollNBluesNJazz − Describes big pharma letting key customers pay months late

without penalties due to fear of losing them, even though it’s irrational.

This user notes their boss inflates quotes for wealthy contacts, turning “deals” into easy sells without pushback

firedmyass − Boss doubles quotes for wealthy acquaintances

to make them think they’re getting a “discount,” and they never complain.

Commenters suggest getting boss directives in writing and spot a fun spelling swap of “bass” for “boss”

inabighat − Advises employees to get all questionable boss orders in writing for protection.

reidmrdotcom − Notes the thread’s funny typo where “bass” was written instead of “boss.”

This Redditor marvels that the boss actually learned, boosting company longevity odds

Stabbmaster − Amazed the boss actually learned from mistakes,

giving hope for company survival and profit.

Users recount new bosses ignoring veteran advice, wasting resources on doomed ideas

try-catch-finally − Shares story of CEO chasing useless “influencer” requests,

ignoring practical dev input, wasting resources.

Dramatic_Explosion − Says new bosses always redo failed ideas

despite expert warnings, wasting company money but not his hourly pay.

Redditors advise preemptive client calls on price hikes and warn of ongoing 8–13% supply jumps.

QuelleBullshit − Advises bosses to communicate price hikes upfront

and manage entitled clients’ expectations to prevent manipulation.

PhreeBeer − Warns about frequent 8–13% supply cost increases

and urges companies to update pricing regularly.

Boss’s bargain blunder boils down to a pricey pedagogy: discount a diva, devour your dough. Community swaps similar sagas of spineless concessions, but cheers the wake-up win. Was the manager’s mic-drop reminder genius or just desserts?

If a VIP griped at your gates, would you hold the line or halve the fee? Dish your deal-gone-wrong dramas below, we’re popping corn!

Annie Nguyen

Annie Nguyen

Hi, I'm Annie Nguyen. I'm a freelance writer and editor for Daily Highlight with experience across lifestyle, wellness, and personal growth publications. Living in San Francisco gives me endless inspiration, from cozy coffee shop corners to weekend hikes along the coast. Thanks for reading!

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