Dear Reader,
A few months back, I told a young handyman—my nephew by marriage—he was charging too little.
He was booked solid, working himself to death, and proud of it.
“Raise your prices,” I said.
He hesitated. “Won’t that scare people off?”
“Good,” I told him. “You need to find the line between busy and profitable.”
That line is where most people lose it.
Too low, and you bleed.
Too high, and you break trust.
It’s not math that decides it. It’s empathy.
A diner owner once told a friend he was done. Too much work. Not enough money.
The advice? Raise everything by a dollar.
He did. Nobody complained. They already knew he was too cheap.
Sometimes the market knows your worth before you do.
But push it too far, too fast, and customers vanish.
Not because they don’t need you—because they stop believing you’re fair.
Price is a mirror.
It shows who you are, what you value, and how much you respect the people you serve.
There’s a sweet spot between greed and generosity.
That’s where real business lives.
If that hits home, that’s what this week’s conversation with Roy is about—The Truth About The Price Being Too High.
In This Episode, You'll Learn:
- The psychology behind pricing confidence and customer perception
- Why some companies are raising prices too far, too fast
- Understanding cancellations as a warning sign of lost trust
- Todd’s nephew’s story: how to know when you’re undercharging or overcharging
- Don Cool’s diner lesson: when raising prices actually saves a business
- The fine line between profit and greed
- How market conditioning, inflation, and fairness influence pricing strategy
- Aaron Gaynor’s toilet ad and why options matter more than ever
- Price discrimination, data tracking, and ethical business practices
- Why serving the masses is still the fastest path to wealth
Episode Chapters & Summary
1. The Price Too High
“You've raised your prices one notch too high.”
Roy opens the episode with a simple but piercing observation: when customers start booking and then canceling shortly after, it's not bad luck — it's price shock. People still need the service, but they've decided you're no longer “the right company.”
Key Takeaways:
- Cancellations often signal lost trust, not lost demand.
- Customers decide if your confidence matches your value.
- Price testing reveals the ceiling — not just your ambition.
2. Pricing as Strategy, Not Emotion
“Pricing is two things: business survival and strategic positioning.”
Todd expands the discussion: pricing isn't just math — it's psychology and timing. He explains how many companies have increased prices beyond earned credibility, mistaking confidence for strategy.
Key Takeaways:
- Strategy sets prices, not ego.
- Confidence must be matched by competence.
- Price hikes without value increases lead to cancellations.
3. The Greed Creep
“Maybe we're getting a little greedy.”
Todd reflects on wage inflation and the ripple effect through the trades — technicians earning $200K, $300K, and the industry chasing inflated expectations. The danger: mistaking a short-term boom for sustainable growth.
Key Takeaways:
- Overpaying today can collapse margins tomorrow.
- The market always self-corrects.
- Greed hides as “momentum” until results decline.
4. Don Cool and the Dollar Menu Lesson
“Raise everything by a dollar.”
Roy shares Don Cool's diner story: a restaurant owner on the brink of closing follows Don's advice to raise every menu item by $1 — and no one complains. The truth: sometimes you're too cheap, and the market knows it.
Key Takeaways:
- Modest price increases often go unnoticed.
- Underpricing is as dangerous as overpricing.
- Customers value fairness more than low prices.
5. The McDonald's Effect
“The $3 meal is now $10 — and Americans have been conditioned to pay it.”
Todd compares fast-food inflation to home services. Prices doubled, yet customers still line up — but wages haven't kept pace. The takeaway: inflation has stretched perception, but not everyone can follow the same curve.
Key Takeaways:
- Inflation trains consumers but tests loyalty.
- Service experience must justify rising prices.
- Price elasticity varies by category and audience.
6. Aaron Gaynor's Toilet Ad
“This toilet is $650 installed. This one is $6,500 installed.”
Roy praises Aaron Gaynor for balancing empathy and profit. By creating ads that present clear, tiered options, Gaynor honors every customer — from modest budgets to luxury buyers — without judgment.
Key Takeaways:
- Options empower customers and reduce sales pressure.
- Serving all segments builds long-term brand strength.
- Price transparency is empathy in action.
7. The Fairness Dilemma
“Some companies are quietly charging more based on your zip code.”
Todd exposes the rise of algorithmic pricing — adjusting costs by location or income. What used to be a private practice is now public. Roy connects it to government programs that scale benefits by income, asking: is this fairness or discrimination?
Key Takeaways:
- Technology enables personalized — and controversial — pricing.
- Fairness is subjective but perception is everything.
- The future of pricing ethics will define brand trust.
8. Serving the Masses vs. the Classes
“If you sell to the classes, you'll live with the masses. But if you sell to the masses, you'll live with the classes.”
Roy reminds listeners that true wealth comes from scale — serving ordinary people extraordinarily well. Luxury markets are small; the middle defines prosperity.
Key Takeaways:
- Accessibility outperforms exclusivity.
- Serving “average” customers builds extraordinary companies.
- Great business is grounded in empathy, not elitism.
9. The Balance of Business and Compassion
“Pricing is about the business and the customer.”
Roy concludes with the ultimate tension — the dance between profit and compassion. Over-focus on margin alienates customers; over-empathy erodes sustainability. Wisdom lives in balancing both.
Key Takeaways:
- Profitability without empathy is greed.
- Empathy without profitability is collapse.
The right price serves both sides fairly.
