Nearly a decade teaching at 3 leading universities.
What the curriculum gave my students: rigorous frameworks and competitive analysis.
What it didn't give them: how to price with conviction, not caution.
That gap travels into your business every day.
#LastMileofTrust
Leaders define what the business is worth. Managers manage around whatever price already exists.
When pricing decisions fall to people whose job is to reduce risk, the default is always caution.
And caution, without vision behind it, is how pricing power slowly disappears.
Copying competitor prices doesn't help you find your voice.
It flattens your story.
It makes you one more option in a crowded market rather than the right one for the right customer.
Every dollar spent on marketing, sales, and brand points at one moment.
The moment the price appears and your prospect says yes or no.
Most businesses treat that as a pricing decision. It's not. It's a trust signal.
The Last Mile of Trust out June 9th. https://t.co/h9fyl5GJe3
I'm tired of watching great entrepreneurs freeze the moment pricing comes up.
Not because they lacked data. Because pricing forces a question no spreadsheet answers: do we believe in what we built, at the level our price requires?
That's this book. Jun 9 https://t.co/h9fyl5Hh3B
It's happening. My book comes out June 9th/
The Last Mile of Trust, I look at why pricing fails, why discounting makes it worse, and the system to fix both.
Most businesses have a pricing problem. They just don't understand what kind.
π https://t.co/BdlIsN2ZR3
I sat in a pricing meeting recently.
8 ppl. 90 mins debating "Professional" vs "Premium."
Asked to see their data: 80% of revenue from 12 customers in the same vertical. None on the tier they were redesigning.
This is pricing without Signal.
Who are your best customers?
Sales rep: "I give 20% discounts on every deal."
CEO: "Sales is crushing it!"
Pulled the data: He's giving away $144K/year because his team doesn't believe in the price.
And they don't believe because HE doesn't believe.
Can you explain your pricing in one sentence?
Founders will obsess over every pixel in their pitch deck but their pricing page looks like it was built in 2014 by an intern.
As if the one thing customers actually pay for doesn't deserve the same craft.
Your company and product deserve better.
I've watched 3 startups run out of money in 6 mths.
None died from product or competition.
They died b/c they were underpriced by 3-5x and too scared to fix it.
More startups die from underpricing than overpricing.
Underpricing is a slow bleed.
Are you underpriced?
Do you ever find pricing meetings have become performance art.
Someone shares a spreadsheet with 47 tabs. An hour later you've debated "good better best" tier names but haven't asked "who is this actually for?"
The best part? No decision made.
Theater, not strategy.
Founder at $3M ARR. 500 customers at $500/mo.
Best 10 customers save $12k/mo.
If he'd priced for those 10 from the start ($2K/mo), he'd have 30 customers instead of 500. Same revenue.
Completely diff biz. Better margins. Lower CAC.
Are you priced for your best customers?
I recently watched a group of co-founders copy competitor pricing from companies that are now dead.
Four out of six startups in their "comp analysis" have shut down.
You're not doing market research.
You're doing startup archaeology.
#pricingmultipliersystem
The best pricing I've seen comes from founders who asked their top 5 customers what they'd pay.
The worst comes from founders who surveyed 1,000 random people who'll never buy.
Data theater vs. actual insight.
How are you gathering + using actual insight?
Here's what to include in your 2026 plan:
Q1: Validate Signal + Match
Q2: Build + Refine
Q3-Q4: Scale
If pricing isn't in your 2026 plan, you're planning to leave money on the table.
What's your pricing strategy for 2026?
October is when most CEOs are doing 2026 planning. Revenue targets. Headcount models. GTM motions. Product roadmap.
I've reviewed 20+ annual plans in the past 2 weeks and exactly ZERO mentioned pricing strategy.
The best annual plans include:
βοΈQuarterly pricing reviews (track the 5 multipliers)
βοΈContinuous testing cadence (experiment backlog)
βοΈPricing narrative refresh (update the board story)
This is Pricing as a CEO System - not a project, a capability.