Sunday mornings, my mom would spread the newspaper across the kitchen table and hand me and my sister a pair of scissors.

We'd cut coupons for hours. Whatever we clipped that week decided what we ate. It decided which stores we'd drive to. Anything to save a few cents.

My dad was in the garage changing the oil on our 1978 Suburban. He did every repair himself. Oil changes, brake pads, whatever needed doing...that truck was older than me and he kept it running by hand.

Here's the thing...we weren't poor.

My mom was an elementary school teacher. My dad was a construction manager at the railroad. We were firmly middle class. But you'd think we were in poverty the way we pinched every penny.

Nobody ever sat me down and explained a philosophy about money. They didn't have to. "We don't waste." "That's not in the budget." "Finish your plate." I absorbed it like oxygen.

I didn't know it had a name back then. I just thought that's how everyone lived.

Thirty years later, I'm running my own company...and I'm still cutting coupons. Different scissors. Same instinct.

I call it the Guilt Tax. I'd bet real money you're paying it too and it’s costing you much more than the check you’ll write Uncle Sam on April 15th.

Pricing is wrong on nearly every company I've worked with. And it's almost always wrong in the same direction.

The founders doing great work — the ones who genuinely change outcomes for their clients — are the ones who chronically undercharge. The worse the work, the higher the price tag. (Think: the $999 "course" that's really a 50-page pdf shat out by ChatGPT.)

But let's talk about the good ones. Because that's who's reading this.

The agency owner who hasn't raised rates on her original clients in four years. New clients pay 3x more for the same work. She knows it's insane. She just can't have the conversation because those early clients "believed in her when nobody else did."

The consultant who charges by the hour instead of by the outcome because charging $50K for something that takes 10 hours "feels wrong"...even though the outcome is worth $500K to the client.

The tradesman who charges $75/hour when the market rate is $200 because they remember being the person who couldn't afford to hire someone like them.

One founder I worked with wouldn't take her flagship program above $5,000. We had a lot of uncomfortable conversations. She moved. Now people buy it for $15,000. Client results actually improved — turns out people take things seriously when they've paid enough to take them seriously.

Every single one of these people is brilliant. Proven. Delivering real value. And every single one of them has a version of my mom's kitchen table running in the background... a money story they inherited long before they started a company.

That's the Guilt Tax. Not a math problem. A wiring problem.

I can only give you my view. I see it caused by a combo of 3 things:

Most founders I work with have at least two of the three. Some have all three stacked on top of each other.

(This is why I don't think it's a hot take to say every entrepreneur needs a therapist.)

When I launched Piper Co, I told myself a very logical and completely nonsensical story.

I started at $6K/month advisory, $10K/month fractional — more than most fractionals, but then again most fractionals don't deliver at the level I do.

What I told myself: I needed the reps, case studies, and easy yes's to build cash flow.

What was actually true: I didn't believe I could ask for more yet.

Different kitchen table. Same coupons.

My blue-collar Texas roots said the same thing my mom said over the newspaper: "Earn hard, spend cautiously, feel guilty about abundance."'

The gap between what I knew I was worth and what I charged has probably cost me high six figures in my first six months. Not exactly a rounding error — more like my baby's college fund.

I recently did a whole MDMA therapy session specifically designed to unwind this thinking. (Told you we all need therapy.) The next afternoon, I put an offer in on a $2M ranch. A literal overnight success that took my entire life to finally unravel.

Now I charge $20K/month base for a Growth Operator engagement, while piloting a new offer that starts with a $250K initial investment. I know that the right deals, structured right, are worth 7 figures to both parties. Yet I've waited.

I see this pattern so clearly in my clients because I am this pattern. Working founders through it is what forced me to start fixing it in myself. You can't tell people to charge what they're worth while quietly negotiating against yourself.

Undercharging doesn't feel like a mistake. It feels like humility. Staying accessible. Honoring the audience that got you here.

But it's none of that. It's just needlessly expensive.

When you underprice, the clients you attract don't value what you do. The anchor you set now is one you'll spend years fighting to escape. The market takes its cues from you — it believes what you signal about what you're worth.

I first sent this Slack message out to my entire company 8 years ago the day we raised prices. I saved it, and I've sent some version of it to almost every client since. I’ve read it dozens of times. I finally believe and live it myself. Now let me share it with you:

Charging your actual value isn't arrogance.

Negotiating against yourself out of guilt isn't humility.

Clarity about your value is kindness — to your clients, your team, and yourself.

So here's the question worth sitting with: where are you paying the Guilt Tax? And what story are you telling yourself to make it feel like the right call?

—Chris Piper
The Growth Operator