Pricing Pointers Roundup: May, 2026
A monthly digest of my pricing ideas and observations from Substack Notes
It’s easy to miss a valuable idea in a fast-moving social media feed. To make things easy, I’ve gathered all of my pricing insights from my Substack Notes & LinkedIn posts over the past month right here in their original order.
(Note: What Substack calls a Note, LinkedIn calls a post. I share pretty much the exact same quick tips on both platforms.)
I now publish full articles only on Substack. If you subscribe to my free Pricing Pointers newsletter, these articles are sent directly to your email inbox so you never have to actually visit Substack to read them.
This is exactly why you might miss my “Notes,” as they only live on the Substack feed and are never emailed. That’s where this monthly Roundup comes in.
You can’t charge a “fair” price because value itself is always changing.
The actual value of your product or service is not static. It’s subjective and dynamic.
Price segmentation works because it accepts this simple truth: the value of any product or service depends on who is buying it and when (even where).
Offering lower prices for accepting inconvenience or delay acknowledges this. Time-rich but money-poor buyers value your product differently than those who are time-poor but money-rich.
Stop searching for the one perfect price. Start searching for the ideal range of prices.
A successful tiered price menu begins with identifying your core value
Most businesses struggle with tiered pricing because they pack too much value into their ‘Good’ tier. This forces a price point that scares away budget-conscious customers.
To fix this, you must strictly define your “core” offering. This consists of the essential elements that pretty much every customer expects to solve their problem.
Think of these as “deal killers.” If you remove one, the customer walks away because the product or service no longer functions for their needs.
Consider, for example, a tire dealer selling passenger tires.
Mounting the new tires and disposing of the old ones are essential components of the offer. (There’s no way I’m leaving the shop with four dirty, old tires in the back of my car.)
Periodic rotation and inspection of the tires, while valuable, is an enhancement.
To build your “Good” tier:
Identify the “deal killers.”
Strip away the bells and whistles.
Provide a functional solution for the budget-conscious.
This ensures you have a competitive entry point without devaluing your premium work.
The takeaway? Stop over-engineering your entry-level offers.
Stop sorting your buyers, and let them sort themselves
It is difficult to accurately identify the maximum willingness to pay (WTP) for each individual customer. They have every incentive to hide it from you. This is why standard tactics often fall short: negotiating prices individually is expensive, while categorizing customers by demographics is frequently inaccurate.
An alternative is to create a mechanism where buyers sort themselves, revealing their willingness to pay, by the choices they make.
A menu of options at different price points shifts the burden of sorting to the buyer, who will naturally select the level of impact they are willing to pay for.
The advantage of this “self-sorting” mechanism is it’s backed by the customer’s actual spending decision. In short, the choice people make from the price menu reveals what kind of buyer they are. That is, how much they care about the price they must pay versus the results or experience they’ll get.
Setting up such a price menu doesn’t require a complex overhaul of your business model. In fact, I’d be willing to bet you’ve experienced many simple self-sorting mechanisms.
Consider how these subtle choices appear in everyday business:
A convenience store that offers pastries at 2 for $2.49 or 1 for $1.49 is using a self-sorting mechanism.
A movie theater that sells tickets for Saturday evening screenings at a higher price than for Tuesday afternoon screenings is using a self-sorting mechanism.
A hotel that charges a higher price for a “Junior Executive Suite” than for a “Standard” room is using a self-sorting mechanism.
A conference that offers “early-bird” registrants a lower admission price than “day-of-the-event” registrants is using a self-sorting mechanism.
An electronics retailer that offers a lower price for a CPU, monitor, and printer when purchased together than when purchased à la carte is using a self-sorting mechanism.
In each of these examples, there’s a trade-off between the price the buyer pays and what they get in exchange. And their choice reveals how much paying a lower price matters to them.
Stop protecting buyers from friction.
Use behavioral hurdles to force price-sensitive customers to earn every discount you grant.
Stop pricing your product.
Design a menu that prices the specific situation and behavior of every individual buyer.
5 Strategic Lenses to Increase Your Sales and Profits by Designing a Tiered Price Menu
Stop hunting for one perfect price.
Build a menu that forces customers to choose their own level of impact.
There is no “perfect” price.
Abandoning the search for the one “perfect” price is the fastest way to stop leaving your hard-earned profits on the table.
Moving to a range of prices allows you to meet different customers exactly where their budget and needs reside.
This flexibility captures high-margin sales from results-driven buyers while still attracting budget-conscious buyers who would otherwise walk away.
Stop leaking margin by ending blanket price cuts.
Blanket discounts give price breaks to buyers willing to pay more.
Instead, require customers to sacrifice something to earn a discount.
An inescapable trade-off filters out buyers willing to pay more.
Protect your margins by stripping features away from your main offer.
Create a lower-priced version of your existing all-inclusive product.
This allows you to reach budget buyers without extra costs.
What features can you strip away that price-sensitive buyers won’t miss, but quality-sensitive buyers definitely will?
The fastest path to higher profits
While most businesses focus on cutting costs or launching new marketing initiatives to boost profits, these efforts often take months, even years, to show significant returns.
The true, immediate profit lever is pricing.
Protect your premium margins by enforcing clear value trade-offs.
Ensure every lower price point requires accepting less value.
This stops high-value customers from choosing your cheapest option.
Does your budget option feel too good for the price?
Maximize your revenue by adjusting prices based on customer demand.
Charge higher prices for peak times and lower prices for off-peak times.
This segments buyers by how much they value ease and convenience.
Which time slot (hour, day, week, month, or season) could you offer at a premium rate?
Stop Guessing: 5 Ways to Convert Your Single-Price Offering into a Customer-Segmenting Machine
A single price is a one-size-fits-none strategy
It’s too expensive for some and too cheap for others.
Stop looking for one perfect number. Give your customers a menu of options instead.
Offer a basic version for budget buyers. Offer a premium version for those who want the best results. Let them choose.
When you provide a range of options at different price points, you lose fewer sales at the bottom and less margin at the top.
When customers ask for a discount, small business owners often cut their price and sacrifice their margin.
Protect your profit margins by refusing to give money away.
Offer a lower-value version when a customer asks for a discount.
This forces buyers to prove they truly need a lower price.
What feature of your offering can you diminish or remove to create a cheaper option?