Why GTM Is Suddenly Everywhere (The Shift from PLG)•
The OKR Paradox: Why Google's Goal-Setting Framework Became Its Own Enemy•
Your Dashboard Is Lying to You (Stop Hiding Behind Data)•
Pricing is Power: If You Can't Raise It, You Don't Have a Business•
The 'Glass Slipper' Trap: Why Early Retention Metrics Mislead•
The 'Imaginary Customer' Problem: Why ICP Often Misleads•
The Hidden Cost of 'Friendly' Feedback•
The Hidden Crisis: How Silent Quitting Reveals a Broken Feedback Loop in Modern Organizations•
The 'Global Market' Myth: Why Local Wins First•
The PM Role is Evolving. Enter the Producer.•
Get Off the Sidelines: It's Your Turn to Play•
GTM 101: Startup Revenue Architecture•
Agile: The Secret Behind Success vs. The Reason We Fail•
The AI Revenue Illusion: GMV vs ARR•
The Hidden Crisis: How Silent Quitting Reveals a Broken Feedback Loop in Modern Organizations•
Agile: The Secret Behind Success vs. The Reason We Fail•
Get Off the Sidelines: It's Your Turn to Play•
Pricing is Power: If You Can't Raise It, You Don't Have a Business•
The PM Role is Evolving. Enter the Producer.•
The Hidden Cost of 'Friendly' Feedback•
Your Dashboard Is Lying to You (Stop Hiding Behind Data)•
Why GTM Is Suddenly Everywhere (The Shift from PLG)•
The 'Imaginary Customer' Problem: Why ICP Often Misleads•
The OKR Paradox: Why Google's Goal-Setting Framework Became Its Own Enemy•
The 'Global Market' Myth: Why Local Wins First•
The AI Revenue Illusion: GMV vs ARR•
The 'Glass Slipper' Trap: Why Early Retention Metrics Mislead•
GTM 101: Startup Revenue Architecture•
Get Off the Sidelines: It's Your Turn to Play•
The 'Global Market' Myth: Why Local Wins First•
The AI Revenue Illusion: GMV vs ARR•
The OKR Paradox: Why Google's Goal-Setting Framework Became Its Own Enemy•
Pricing is Power: If You Can't Raise It, You Don't Have a Business•
Your Dashboard Is Lying to You (Stop Hiding Behind Data)•
The Hidden Crisis: How Silent Quitting Reveals a Broken Feedback Loop in Modern Organizations•
Agile: The Secret Behind Success vs. The Reason We Fail•
The 'Glass Slipper' Trap: Why Early Retention Metrics Mislead•
The Hidden Cost of 'Friendly' Feedback•
The PM Role is Evolving. Enter the Producer.•
The 'Imaginary Customer' Problem: Why ICP Often Misleads•
Why GTM Is Suddenly Everywhere (The Shift from PLG)•
GTM 101: Startup Revenue Architecture•
Agile: The Secret Behind Success vs. The Reason We Fail•
The Hidden Crisis: How Silent Quitting Reveals a Broken Feedback Loop in Modern Organizations•
The Hidden Cost of 'Friendly' Feedback•
The OKR Paradox: Why Google's Goal-Setting Framework Became Its Own Enemy•
Why GTM Is Suddenly Everywhere (The Shift from PLG)•
The 'Imaginary Customer' Problem: Why ICP Often Misleads•
Pricing is Power: If You Can't Raise It, You Don't Have a Business•
The PM Role is Evolving. Enter the Producer.•
Why GTM Is Suddenly Everywhere (The Shift from PLG)•
The OKR Paradox: Why Google's Goal-Setting Framework Became Its Own Enemy•
Your Dashboard Is Lying to You (Stop Hiding Behind Data)•
Pricing is Power: If You Can't Raise It, You Don't Have a Business•
The 'Glass Slipper' Trap: Why Early Retention Metrics Mislead•
The 'Imaginary Customer' Problem: Why ICP Often Misleads•
The Hidden Cost of 'Friendly' Feedback•
The Hidden Crisis: How Silent Quitting Reveals a Broken Feedback Loop in Modern Organizations•
The 'Global Market' Myth: Why Local Wins First•
The PM Role is Evolving. Enter the Producer.•
Get Off the Sidelines: It's Your Turn to Play•
GTM 101: Startup Revenue Architecture•
Agile: The Secret Behind Success vs. The Reason We Fail•
The AI Revenue Illusion: GMV vs ARR•
The Hidden Crisis: How Silent Quitting Reveals a Broken Feedback Loop in Modern Organizations•
Agile: The Secret Behind Success vs. The Reason We Fail•
Get Off the Sidelines: It's Your Turn to Play•
Pricing is Power: If You Can't Raise It, You Don't Have a Business•
The PM Role is Evolving. Enter the Producer.•
The Hidden Cost of 'Friendly' Feedback•
Your Dashboard Is Lying to You (Stop Hiding Behind Data)•
Why GTM Is Suddenly Everywhere (The Shift from PLG)•
The 'Imaginary Customer' Problem: Why ICP Often Misleads•
The OKR Paradox: Why Google's Goal-Setting Framework Became Its Own Enemy•
The 'Global Market' Myth: Why Local Wins First•
The AI Revenue Illusion: GMV vs ARR•
The 'Glass Slipper' Trap: Why Early Retention Metrics Mislead•
GTM 101: Startup Revenue Architecture•
Get Off the Sidelines: It's Your Turn to Play•
The 'Global Market' Myth: Why Local Wins First•
The AI Revenue Illusion: GMV vs ARR•
The OKR Paradox: Why Google's Goal-Setting Framework Became Its Own Enemy•
Pricing is Power: If You Can't Raise It, You Don't Have a Business•
Your Dashboard Is Lying to You (Stop Hiding Behind Data)•
The Hidden Crisis: How Silent Quitting Reveals a Broken Feedback Loop in Modern Organizations•
Agile: The Secret Behind Success vs. The Reason We Fail•
The 'Glass Slipper' Trap: Why Early Retention Metrics Mislead•
The Hidden Cost of 'Friendly' Feedback•
The PM Role is Evolving. Enter the Producer.•
The 'Imaginary Customer' Problem: Why ICP Often Misleads•
Why GTM Is Suddenly Everywhere (The Shift from PLG)•
GTM 101: Startup Revenue Architecture•
Agile: The Secret Behind Success vs. The Reason We Fail•
The Hidden Crisis: How Silent Quitting Reveals a Broken Feedback Loop in Modern Organizations•
The Hidden Cost of 'Friendly' Feedback•
The OKR Paradox: Why Google's Goal-Setting Framework Became Its Own Enemy•
Why GTM Is Suddenly Everywhere (The Shift from PLG)•
The 'Imaginary Customer' Problem: Why ICP Often Misleads•
Pricing is Power: If You Can't Raise It, You Don't Have a Business•
The PM Role is Evolving. Enter the Producer.•
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Pricing is Power: If You Can't Raise It, You Don't Have a Business

Pricing is Power: If You Can't Raise It, You Don't Have a Business

4 min read

There is a moment in every startup's life that reveals its true nature.
It is not the launch. It is not the funding round.
It is the moment you send the email:

"We are updating our pricing."

Most founders dread this. They delay it for years.
They grandfather early users forever.
They apologize in the first paragraph.

Stop it.
If you cannot raise prices, you do not have a business.
You have a hobby subsidized by venture capital.

The "Grandfathering" Trap

"Grandfathering" means letting existing customers keep their old, cheap price forever while charging new customers more.
It feels like loyalty. It feels honorable.

In reality, it is cowardice.

By grandfathering everyone, you are creating two companies:

  1. The Zombie Company: Serving 80% of your user base at 2019 prices, often below your current cost to serve.
  2. The Real Company: Trying to grow with new pricing, but dragged down by the support burden of the Zombie Company.

Oswarld’s Rule: Never grandfather forever.
Grandfather for 12 months. Maybe 24.
But eventually, everyone must pay the market rate.
If they leave, they were not customers. They were beneficiaries of your insecurity.

The Only Three Pricing Strategies That Matter

Forget the textbooks. Forget "Cost-Plus."
In software, there are only three ways to price.

1. The "Commodity" Price (Race to the Bottom)

"Competitors charge $20, so we charge $18."
This is the death spiral. You are admitting your product has no unique value.
You are fighting on margin against incumbents who have more cash than you.
Avoid this.

2. The "Value" Price (The 10x Rule)

"We save you $5,000 a month in labor, so we charge $500."
This is the only sane way to price B2B SaaS.
You anchor your price not to your competitors, but to the problem you solve.
If you solve a $1M problem, charging $10k is a steal.
If you solve a $100 problem, charging $10 is extortion.

3. The "Pain" Price (The Scream Test)

How do you know if your price is too low?
Nobody complains.

If 100% of prospects say "Yes" to your price, you are leaving money on the table.
You want 20% of them to say "That's expensive" — and then buy anyway.
That friction proves you have found the ceiling of your value.

How to Raise Prices (The Playbook)

Do not write a long, apologetic letter explaining that "AWS costs went up."
Customers do not care about your AWS bill.
They care about their value.

Step 1: The "Repackaging"

Never just raise the number. Change the package.

  • Old: $29/mo for Basic.
  • New: $49/mo for "Pro" (includes Basic + 2 new features).

Psychologically, paying more for the same thing hurts.
Paying more for a better thing feels like an upgrade.
Even if the "better" features are minor, they provide the narrative cover for the hike.

Step 2: The "Anchor"

Introduce a new "Enterprise" or "Business" tier at a shockingly high price.

  • Pro: $49/mo
  • Business: $499/mo

Suddenly, $49 looks cheap.
Before, they compared $49 to $0. Now they compare it to $499.

Step 3: The Execution

  1. New Customers First: Change the pricing page today. No announcement. Just do it. See what happens to conversion.
  2. Existing Customers Second: Give them 60 days notice.
  • "On Dec 1st, we are moving to the new Pro plan."
  • "As a loyal user, you get a 20% discount for the first year."
  • "Or, lock in the current price for 1 year by switching to Annual billing today."

This last point is crucial.
A price hike is the best churn reduction tool you have.
It forces monthly users to commit to Annual plans to "save" money.
You get cash upfront; they get a discount. Everyone wins.

The Churn Fallacy

"But Oswarld, if I raise prices, customers will leave!"

Good.
Let them leave.

Let’s do the math.

  • You have 1,000 customers paying $10. Revenue = $10,000.
  • You raise price to $20.
  • 30% of customers leave (Massive churn!).
  • You now have 700 customers paying $20. Revenue = $14,000.

Result:

  • Revenue up 40%.
  • Support volume down 30%.
  • Server costs down 30%.

You are making more money with less work.
The customers who left were likely your noisiest, least profitable users anyway.

Conclusion

Pricing is not math. It is a test of confidence.
It asks: "Do you believe your product is worth it?"

If you don't, why should they?

Raise the price.
If nobody screams, raise it again.