Summary

The article emphasizes the importance of building trust with an email list by providing value and not rushing to monetize, suggesting that over-asking can damage relationships and reduce the effectiveness of marketing efforts.

Abstract

The author, Scott Stockdale, prides himself on infrequently asking his email list subscribers for sales or promotions, having made direct asks only three times since April 2021. Instead, he focuses on offering free valuable content, such as guides, courses, writing challenges, business ideas, and consulting calls. Stockdale argues that the key to successful online entrepreneurship is to establish credibility and solve problems for the community without asking for anything in return for at least the first year. Drawing on insights from Tim Denning, he illustrates the pitfalls of aggressive marketing and the benefits of a patient approach, where the community's willingness to engage with asks is likened to a rechargeable battery with a 30-day cycle. The article underscores the significance of genuine connections and the natural progression of opportunities, including sales, when trust is established.

Opinions

The author believes that passive income is not about quick transactions but about nurturing a community over time.
Stockdale suggests that an email list's value is not solely in direct sales but also in the organic growth and reach facilitated by non-paying subscribers.
He criticizes the common practice of immediately monetizing an email list, comparing it to a one-night stand, which is ineffective and shortsighted.
The author endorses Tim Denning's view that a community's tolerance for promotional asks is limited and should be managed carefully, with no more than 12 asks in the second year of engagement.
Stockdale shares a personal anecdote to demonstrate how providing consistent value can lead to meaningful relationships and genuine support, including purchases and testimonials, without the need for aggressive marketing.
The article conveys the idea that making money online becomes more feasible once you've established a reputation for not needing immediate financial returns from your audience.

“Put Out Content, Build an Email List, Sell a Product” — Why Isn’t It Working For You?

You’re likely forgetting this crucial detail

Photo by Demian Tejeda-Benitez on Pexels

With my email list, do you know what I’m most proud of?

How little I ask for.

Since April 2021, I’ve sent 76 emails, and I’ve only made a direct ask of my subscribers three times.

Once was for my girlfriend’s book. Once for my podcast relaunch. And once for my freelance writing book.

In return, I’ve given away:

My free 19-page guide: Everything I Did to Quit My 9–5 Job & Transition Into Profitable, Sustainable Solopreneuring
My free online course: 0–500 Email Subscribers Through Writing
A Free 30-Day Writing Challenge
350+ business ideas
My freelancing proposal template
Free 1–2–1 consulting calls
A free “Headlines Masterclass”
Inspiring content creator stories
Tips and tools to improve their writing

This isn’t to say how great I am. Nor am I an expert at this stuff.

I’m really not.

However, I have been able to make thousands of dollars online and create opportunities out of thin air — all from an email list that has less than 1,000 people on it.

Here’s how.

First, don’t do this

Tim sums it up best:

“Passive income isn’t a one-night stand. You don’t wake up, start a community, get five people in there, and then attempt to have your way with them on the first night. That’s what most people do. Join an email list and find out. Within 24 hours you’ll be offered a one-night stand.

“To prove it, I joined ten email lists in the last week of creators I admire. Nine out of ten tried to sleep with me in the first email. So what did I do?

“Unsubscribe.”

— Tim Denning

“Nine out of ten tried to sleep with me in the first email.”

The temptation will be great. You’ll want to share an affiliate link, sell a PDF, or do something that progresses your side hustle dream.

Resist.

Takeaway: Don’t ask for anything from your email list for the first 12 months.

Do this instead

Focus on the needs of your community and solve their problems for free for a year. Show your worth. Prove your experience.

When year two rolls around, you can make a few asks.

But don’t f*ck it up.

“The best way is to pretend you get one ask with your community […]

“Your community’s patience with asks is like a battery. As soon as you ask for something, the battery goes to 0%. It takes 30 days before they’re ready to get an ask from you again.

“So in year 2, you get a maximum of 12 asks. See the difference? Now you see why it’s stupid to ask your community to pay for an unproven product that may make you a $1 commission.”

— Tim Denning

What might an ask look like?

An eBook
A membership community
Coaching
An affiliate link to a product you get a commission on
An online course
A live event

So it’s okay to ask for things — just don’t over-ask.

Also remember this:

Not everyone on your email list is a customer. 90% of them will never buy from you. 10% will. The other 90% still have enormous value because they’ll share your work and increase your reach.

Show my working

Back in April 2021, a young man from Budapest found one of my Medium articles.

He clicked the call-to-action and joined my email list.

Then, between April 2021 and December 2022, he received these emails:

Screenshots from my ConvertKit dashboard (sorry it’s so blurry!)

After my announcement email about becoming a full-time writer, he reached out to me for the first time:

We met up in Budapest, shared ideas and stories, and we’ve emailed a number of times since.

I love chatting with writers.

When I told people about my mum getting cancer, he was one of the first people to reach out.

And when I launched my ebook, he didn’t hesitate to buy it and leave a testimonial.

This is what friends do.

Takeaways

Over-asking is the quickest way to destroy trust.

No one wants to be sold to.

Instead, give away all your best stuff for free, build genuine connections, and let opportunities present themselves.

And if you do make an ask of your network, make it meaningful — not for a poorly thrown-together PDF.

You’ll make money online when you don’t really need it.

“One of the secrets to getting what you want in life is creating the perception that you don’t need a thing.”

— Curtis Jackson