Why 'CEOs' Keep Asking for Discounts

You’ve been there. You get an email that starts with praise—"Your product is amazing! A real game-changer!"—and ends with a punch to the gut: "...but we're an early-stage startup and can't afford $200/month. Any chance of a discount?"

My first reaction used to be pure frustration. "$200 a month? If you can't afford $200 to solve a core business problem, you're not a real CEO." I’d see them as tire-kickers, "fake CEOs" who would inevitably become my most demanding, least profitable customers.

Then I realized something: I was doing it all wrong.

The anger wasn't productive. The problem wasn’t just about cheapskates; it was about a massive disconnect. And understanding that disconnect is the difference between a business that struggles and one that thrives.

The Problem with Getting Mad

Most founders see a discount request as an insult to their product's value. We get defensive. We rant about "Pains In The Ass" (PITAs) who don't understand the work we've put in.

But the real issue isn't that these founders are cheap—it's that we're talking to a different species of "CEO" than we think. And we've probably done a terrible job of explaining why our price is a bargain, not a barrier.

Your price isn't the problem. Your communication is.

What Actually Works: Three Truths That Change Everything

1. Understand Who You're Actually Talking To

That email signature says "CEO," but you're not talking to Tim Cook. As one wise person put it, you're often talking to an "Instagram CEO," whose COO is their mom and their CIO is a student they found on a freelancer site.

Stop picturing a corner office and start picturing who's really behind the screen:

The Solopreneur: They're a one-person show. Your $200 fee isn't a line item on a budget; it's their grocery bill. Every dollar is scrutinized because it comes directly out of their pocket.
The Wantrepreneur: They have a brilliant idea, a shoestring budget, and zero revenue. Your product might be the key to their entire concept, but $200 feels like a massive gamble on a dream that might go nowhere.
The Side-Hustler: They have a six-figure day job at a big company where enterprise tools are free. They're applying that same frugality to their side project, where their personal risk tolerance is near zero.

These aren't bad people. Their frugality is a survival mechanism.

The key: Their title is an aspiration, not a reflection of their bank account. Treat them accordingly.

2. Make Your Value Blindingly Obvious

Here's the hard truth: If someone says your product is too expensive, they're not really talking about the price. They're telling you that you've failed to show them how it will make or save them more than it costs.

I’ve seen founders say, "Without my API, their business wouldn't even exist!" From your side of the table, the value is obvious. But that's the founder's curse—you're too close to it.

People don't buy a data API. They buy the ability to launch their real estate analytics site in a weekend. They don't buy a SaaS tool. They buy a solution to a problem that's costing them time and money.

If the ROI on your $200/month tool is a foggy "maybe," of course it's too expensive.

The key: Your landing page shouldn't sell features; it should sell a future. Do the math for them. "Building this yourself would take 300 hours and cost $30,000. Or you could start today for $200."

3. Use Your Price as a Filter

The founder who originally complained had a brilliant insight, even if he didn't realize it. He said he’d rather have 50 happy customers paying $200 than 120 paying $100, because the extra customers would be "90% of the work for only 20% extra revenue."

This is a masterclass in understanding the PITA-to-Profit ratio.

A bad-fit customer—one who haggled from day one—will drain your support queue, churn at the first sign of trouble, and burn you out. For a bootstrapped business, your time and sanity are your most valuable assets.

Saying "no" to a discount isn't just about protecting revenue. It's about protecting your focus.

The key: Your price isn't just a number; it's a gatekeeper for your ideal customer. Don't be afraid to fire prospects before you even hire them.

What This Actually Looks Like

So, what do you do when the next email lands? You don't have to just say "yes" or a grumpy "no." You can get strategic.

Here are four ways to handle it:

1. The Ol' Switcheroo. Raise your public price to $499/month. When a "CEO" emails you for a deal, you become their hero. "I understand budgets are tight. We have a special, unlisted Startup Plan for just $199/month. Interested?" They feel like they won, and you get your target price.

2. The Smart Ladder. If your cheap plan is just a feature-stripped version of your expensive one, you’re doing it wrong. Align your tiers to the customer's journey. A cheap/free tier should be for testing an idea. The pro tier is for launching a business. Once they prove their concept on the low tier, upgrading to the pro tier to actually make money becomes a no-brainer.

3. Turn the Tables. A price objection is a cry for clarity. Instead of getting defensive, get curious. "Thanks for reaching out. It sounds like the value isn't quite aligning with the price for you. Could you help me understand what part of the ROI seems unclear from your perspective?" This disarms them, makes them think, and gives you priceless market research.

4. The "Get Serious" Filter. Offer an annual plan. "Our standard rate is $400/month, but for founders committed to building on our platform, we offer a one-year license for $2,400 upfront." This instantly separates the serious builders from the tire-kickers and dramatically improves your cash flow.

The Long Game

This isn't about winning negotiations. It's about building a sustainable business filled with customers you actually enjoy working with. Your pricing strategy is one of the most powerful tools you have to achieve that.

It takes time. You'll have to experiment. You'll have to say "no" to revenue that feels tempting in the short term. But the payoff is real: a business that doesn't just make money, but also protects your peace of mind.

Getting Started (Without the Anger)

Read your own landing page. Does it scream ROI, or does it just list features? Rewrite it to focus on outcomes.
Define your PITA line. Decide, right now, who you don't want as a customer. Build your pricing to filter them out.
Pick one of the plays above. Change your pricing page. Draft a new email response. Test it for a month.
Be patient. You're not just changing a number; you're changing your business philosophy.

The Bottom Line

When a "CEO" tells you your product is too expensive, don't hear an insult. Hear an opportunity. An opportunity to clarify your value, to strengthen your positioning, and to build a better filter for the exact right customers.

The best pricing strategy doesn't feel like a negotiation. It feels like a perfect match between a problem and a solution.

And that's not something you can discount—it's something you have to design.