Scan time: 2-3 minutes / Read time: 3-5 minutes
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Hey rebel ideapreneurs 🦸♂️🦸♀️
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🙋♂️ Miles’s community that costs him money
Say hi to Miles.
He’s a customer success manager,
and on the side he runs a free online community for new dads who work from home.
Four hundred dads swap tips there every week.
Naps, baby gear, getting work done with a baby in the house… all of it.
There’s just one teeny-tiny problem.
It costs him sixty dollars a month to host,
plus about five hours a week of his time.
So Miles makes a plan.
Charge every member eight dollars a month.
Easy, right?
He mentions it…
and a few of his most active dads say they’d leave.
Gulp. 😬
🧩 His struggle:
He thinks charging members is the only way to cover his costs, so he could lose his most active dads.
Then, in the waiting room at his daughter’s checkup,
he picks up a magazine.
Inside is the true story of a man who also ran something free that people loved,
and who later became worth $1.3 billion.
And it all began with… an email to his friends.
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📋 The man who sent his friends a list
Picture this.
It’s 1995, in San Francisco.
Craig Newmark is typing up a list of things to do around town,
to email to his friends.
His day job?
Charles Schwab, a big investing company,
where he kept the company’s computer systems safe.
The list was just for fun.
Then people on the list started asking him to add things.
Could he add job openings?
He said yes.
Then they asked for more, and he kept saying yes.
The list grew so big that he moved it from email onto a website.
And he kept the name his friends had given it:
Craigslist.
Soon a lot of people were using it.
So Craig had to decide how it would make money.
In his own words, his decision in early 1999 was to make money from Craigslist “as little as possible.”
Ha.
Not exaaactly a business-school answer.
He didn’t charge the people reading the listings.
Even years later, the site showed no banner ads.
Instead, he charged one group:
companies posting job ads in San Francisco.
Until then, they had posted for free.
Wait, why would a company pay?
Because to a company, one good worker found through a job ad is worth far more than the fee.
And the people looking for work?
They still paid nothing.
Bingo! 🎯
In 2004, job ads in New York and Los Angeles started costing twenty-five dollars.
By then, a job ad in San Francisco cost seventy-five.
Today, most posts on Craigslist are still free.
Almost all of the fees are paid by businesses:
companies hiring, car dealers, and landlords renting apartments in a few big cities.
And those fees?
They bring in hundreds of millions of dollars a year.
Cha-ching! 💰
Free for readers ain’t the same as free for everyone.
Get this — Forbes once put Craig’s fortune at $1.3 billion.
Wowza. 🤩
And bankers and investors wanted to give him about eleven billion dollars more, he says.
He turned it down.
That kind of money ain’t easy to walk away from.
Today, he is giving almost all of his money away.
Craig never charged the people who came to read Craigslist.
He charged the businesses that wanted to reach them.
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🔥 The recipe
➡️ Let the Business Pay, Not the Reader
Craig kept Craigslist free for everyone reading it,
and charged the companies that wanted to hire those readers.
This strategy is called Let the Business Pay, Not the Reader.
Your readers come for free.
The businesses that want to reach them pay.
So who’s that business for a newsletter or a community?
A sponsor:
a company that pays to tell your readers about something it sells.
Remember Craig’s job ads?
He didn’t make his readers pay to use the site.
He found the companies that wanted to hire the people reading his job ads,
and asked those companies to pay.
But when most of us want a free newsletter to earn money,
we look at our readers first… and try to charge them.
So look at who wants to reach your readers instead, and let those businesses pay.
Today your AI sidekick can list those businesses for you in a minute.
Your job is picking the ones your readers would be glad to hear about.
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🛠️ Miles’s turn
So what about Miles and his free community for new dads who work from home?
Remember, he was about to charge every member eight dollars a month.
That night, he runs the prompt at the bottom of this email,
and asks how else the community could pay for itself.
His AI sidekick says:
Keep it free for the dads, and ask a company that sells baby carriers to sponsor your weekly tips post.
Huh.
He hadn’t even thought of that.
Before bed, Miles sends a short note to a baby carrier company
that his members keep recommending to each other.
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🌅 Ten weeks later
The community is still free.
And it has grown to six hundred dads.
Two companies sponsor the weekly tips post now:
the baby carrier company, and a maker of quiet desk fans.
Nobody left.
Not one dad.
Three of them even wrote in to say the fan was exactly what they needed for nap-time calls.
Your readers don’t have to be the ones who pay you.
Somebody already wants to reach them.
Keep the list free for readers, and charge the company that’s hiring.
That’s it, my fellow anti-status-quo-ers!
Yours ‘helping you skip years of pain and frustration in your life and business’ Vijay Peduru 🦸♂️
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🏄♀️ The prompt
Give your AI sidekick who your readers are and what you planned to charge them, and let it find who should pay instead.
🧰 What you’ll need
Who your readers are, and what they talk about
- A minute’s worth. Type it, or say it out loud with a voice tool, messy is fine.
- e.g. A free online community of 400 new dads who work from home. They swap tips on naps, baby gear, and getting work done with a baby in the house.What you were thinking of charging, and why
- One or two lines.
- e.g. I was going to charge every member $8 a month, because hosting the community costs me $60 a month.
🚀 How to run it
Open your AI sidekick, ChatGPT, Claude, or whichever one you use. The best is one that can already see your notes, wherever you keep them (on your computer, on the web, or in the cloud).
Swap the two examples, the text inside the curly brackets, for your own, then run it. If your AI sidekick can already see your notes, you can run it as is.
🧪 Want to test it first? Run it without changing anything, and it will use the examples.
CONTEXT
- Use my own material first. If you can see my notes, my sent issues, or my community's posts, wherever they are stored, read them there. If I uploaded a file, read that. Pull the real details from them instead of the examples below.
- Write in plain, friendly words, like a friend who wants my free newsletter or community to pay for itself.
- If you know who my readers are, write for them. Otherwise assume new dads who work from home.
- If I have replaced the examples, use only mine. If an example is still there, fill it in from what you already know about me, and mark it as your assumption. If you don't know anything about me yet, use the example exactly as written. If I dictated an input, it will be messy; that is fine, do not ask me to clean it up.
- The one rule for this build: my readers stay free. The money comes from businesses that want to reach my readers. Only suggest a business my readers would be glad to hear about, ideally one they already mention or recommend to each other.
INPUTS
1. Who my readers are, and what they talk about (typed or spoken, a minute's worth):
{e.g. A free online community of 400 new dads who work from home. They swap tips on naps, baby gear, and getting work done with a baby in the house.}
2. What I was thinking of charging my readers, and why (one or two lines):
{e.g. I was going to charge every member $8 a month, because hosting the community costs me $60 a month.}
END OF INPUTS
OUTPUT
1. What my readers need: from input 1 and my notes, list the things my readers already buy, or keep asking each other about. Five short lines.
2. Who wants to reach them: for each line, name the kind of business that sells it. Only name a real company if my readers already mention it, or if you are confident it exists. If you are unsure, say so.
3. Rank the five businesses by how glad my readers would be to hear from them. Put first the one my readers already recommend to each other.
4. Ask me one question to check the top pick fits my readers, and wait for my answer.
5. Write a short note I can send to the top business: who my readers are, how many there are, where their name would appear, and one plain sentence on why my readers would be glad to hear about them. Keep it under 120 words, in my voice.
6. Finish with one line I can post to my readers once a business says yes, saying the newsletter or community stays free, and who is helping keep it that way.