How to Start AI Newsletters With AI, Step by Step
Built only from the steps described in 9 sourced AI Newsletters cases. Each step is attributed to the case it comes from; we do not add steps of our own.
How they started
Pick a narrow promise
One curated summary a week for busy professionals.
From Unnamed side hustler (Side Hustle School episode 3152), step 1. About $1,400/mo, Self-Reported
Build a directory
aitools.fyi lists AI tools and draws search traffic.
From World of AI (aitools.fyi), step 1. $6,000 a month, Self-Reported
Test content where you already have reach
He tried AI topics as Twitter threads first.
From Superhuman AI newsletter (Zain and Awais Kahn), step 1. Six figures a month, Self-Reported
Start with an audience
He already had a podcast audience.
From Chris Koerner (The Koerner Office), step 1. $3K to $7K per sponsored send, Self-Reported
Post about AI
He built an audience covering AI on social media.
From Hasan Toor (The ProHuman), step 1. $60,000 a month combined, Self-Reported
Post daily
Two AI threads a day on X.
From Rowan Cheung (The Rundown AI), step 1. Eight-figure business, Self-Reported
Build a newsletter audience
A daily AI newsletter with 100K+ subscribers.
From Ben Tossell (Ben's Bites), step 1. 7-figure business, Self-Reported
Pick an audience
Senior professionals learning AI.
From Alex Fiore (AI Central), step 1. More than $150,000 from the ad network to date, Self-Reported
Pick a language niche
German-language AI coverage.
From The Autopilot (Sascha Hoffmann), step 1. $726 MRR, Independently Documented
What they did next
Draft with AI, edit by hand
AI gets it halfway; personal commentary is the product.
From Unnamed side hustler (Side Hustle School episode 3152), step 2. About $1,400/mo, Self-Reported
Market on LinkedIn
Sample summaries in productivity groups and a two-week free trial.
From Unnamed side hustler (Side Hustle School episode 3152), step 3. About $1,400/mo, Self-Reported
Launch a newsletter
World of AI on beehiiv.
From World of AI (aitools.fyi), step 2. $6,000 a month, Self-Reported
Sell plans
Paid listing and promotion plans for tool makers.
From World of AI (aitools.fyi), step 3. $6,000 a month, Self-Reported
Launch the newsletter
It passed 135,000 subscribers within three months.
From Superhuman AI newsletter (Zain and Awais Kahn), step 2. Six figures a month, Self-Reported
Sell sponsor slots
Ad spots sell out and drive the revenue.
From Superhuman AI newsletter (Zain and Awais Kahn), step 3. Six figures a month, Self-Reported
Repurpose with AI
A custom model turns his material into newsletter drafts.
From Chris Koerner (The Koerner Office), step 2. $3K to $7K per sponsored send, Self-Reported
Sell sponsorships
Direct sponsors pay per send.
From Chris Koerner (The Koerner Office), step 3. $3K to $7K per sponsored send, Self-Reported
Launch a newsletter
He monetizes it with ads.
From Hasan Toor (The ProHuman), step 2. $60,000 a month combined, Self-Reported
Start an agency
He manages other AI creators.
From Hasan Toor (The ProHuman), step 3. $60,000 a month combined, Self-Reported
Funnel to a newsletter
Each thread promoted The Rundown.
From Rowan Cheung (The Rundown AI), step 2. Eight-figure business, Self-Reported
Monetize recommendations and ads
Recommendations funded early hires.
From Rowan Cheung (The Rundown AI), step 3. Eight-figure business, Self-Reported
Pivot to education
An AI education portal.
From Ben Tossell (Ben's Bites), step 2. 7-figure business, Self-Reported
Sell lifetime access
A one-time lifetime plan instead of monthly billing.
From Ben Tossell (Ben's Bites), step 3. 7-figure business, Self-Reported
Build an AI pipeline
Claude Code, Notion and n8n support content.
From Alex Fiore (AI Central), step 2. More than $150,000 from the ad network to date, Self-Reported
Diversify revenue
Ad network, brand deals and affiliates.
From Alex Fiore (AI Central), step 3. More than $150,000 from the ad network to date, Self-Reported
Publish weekly
A free issue builds the list.
From The Autopilot (Sascha Hoffmann), step 2. $726 MRR, Independently Documented
Sell paid subscriptions
Readers pay for the full version.
From The Autopilot (Sascha Hoffmann), step 3. $726 MRR, Independently Documented
How they grew
Fix retention
Bonus digests improved retention by about 20%.
From Unnamed side hustler (Side Hustle School episode 3152), step 4. About $1,400/mo, Self-Reported
AI Newsletters: common questions
How much do people make with AI Newsletters and AI?
Across the 5 of our 9 sourced cases that report a monthly figure, amounts range from $726 to $100,000 a month, with a median of $6,000. These are what each source reports, not typical results.
How much does it cost to start?
About $20 a month plus platform fees in the one case that discloses a cost. 1 of 9 cases disclose a startup cost.
How long until the first dollar?
One case reports just under $300 in its first month; the others do not say. This comes from what our cases report.
Which AI tools do these cases use most?
ChatGPT (3 cases), Claude (2 cases), Canva (1 case), n8n (1 case). Only tools named in the sources are counted.
How reliable are these income figures?
1 of 9 cases are independently documented, meaning a news outlet says it reviewed records. 8 are self-reported. Every case links its source.
What are the main risks?
Many newsletters cover the same AI news. Sponsors usually want a sizeable, engaged list first. AI-written issues still need fact-checking.
How many of these cases say when they made their first dollar?
2 of 9 cases state a time to first revenue. For example: Unnamed side hustler (Side Hustle School episode 3152): "First month (42 subscribers, just under $300 a month)"; Rowan Cheung (The Rundown AI): "He says it was profitable from day one; recommendations brought $30K to $40K a month early on". The rest do not say, so treat any single timeline as one example, not a norm.
What went wrong or held these cases back?
9 of 9 cases list limitations or risks drawn from their sources. Examples: Unnamed side hustler (Side Hustle School episode 3152): Some subscribers left wanting more than one summary a week; World of AI (aitools.fyi): Depends on interest in AI tools staying high, which the founder says is declining; Superhuman AI newsletter (Zain and Awais Kahn): The figures are self-reported and were not independently checked. Each case page lists them in full.
Do I have to report this income to the IRS if I never get a 1099-K?
Yes. The IRS says that whether or not you receive a Form 1099-K, you must report all income from selling goods or services on your tax return. Payment apps and online marketplaces must send a 1099-K when payments for goods or services total over $20,000 in more than 200 transactions, but they may send one for lower amounts. Source: IRS, "Understanding your Form 1099-K" (irs.gov/businesses/understanding-your-form-1099-k), checked 2026-10-20. General information, not tax advice.
Do I owe self-employment tax on side hustle income in the US?
According to the IRS, you must pay self-employment tax and file Schedule SE if your net earnings from self-employment were $400 or more. The rate is 15.3% (12.4% Social Security and 2.9% Medicare), and you may need to pay estimated taxes quarterly. Source: IRS, "Self-employment tax (Social Security and Medicare taxes)" (irs.gov/businesses/small-businesses-self-employed/self-employment-tax-social-security-and-medicare-taxes), checked 2026-10-20. General information, not tax advice.