May 6, 2026

EP 546 Newsletter Email Money Secrets: Making $25K Per Email Without Breaking the Law

Discover how AI entrepreneurs are making $25K per email using email strategy and side hustles—the tactics that sound illegal but operate in a legal gray area. In this episode, we break down the email list monetization playbook, compliance boundaries, and the exact moves separating six-figure emailers from struggling list owners. If you want to scale your side hustle with email marketing, this is the strategy most parents never hear about.

Discover how parents with zero writing experience are building 7-figure newsletter empires using AI and Beehiiv. Learn the exact 4-revenue-stream system that generated millions for creators like The Rundown AI (2M+ subscribers) and Superhuman AI (7 figures in 4 months). This episode reveals why companies pay millions for email lists, how to grow without ads, and the AI content creation process that takes hours down to minutes.

AI newsletters are the most profitable side hustle on the internet right now. While you're trading hours for dollars at your job, parents with zero writing experience are building seven-figure newsletter empires from their kitchen tables using nothing but AI tools and platforms that take 0% of their revenue.

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The AI Newsletter Gold Rush That's Creating Millionaire Parents From Kitchen Tables

Episode Overview

Discover how AI entrepreneurs are making $25K per email using email strategy and side hustles—the tactics that sound illegal but operate in a legal gray area. In this episode, we break down the email list monetization playbook, compliance boundaries, and the exact moves separating six-figure emailers from struggling list owners. If you want to scale your side hustle with email marketing, this is the strategy most parents never hear about.

Discover how parents with zero writing experience are building 7-figure newsletter empires using AI and Beehiiv. Learn the exact 4-revenue-stream system that generated millions for creators like The Rundown AI (2M+ subscribers) and Superhuman AI (7 figures in 4 months). This episode reveals why companies pay millions for email lists, how to grow without ads, and the AI content creation process that takes hours down to minutes.

AI newsletters are the most profitable side hustle on the internet right now. While you're trading hours for dollars at your job, parents with zero writing experience are building seven-figure newsletter empires from their kitchen tables using nothing but AI tools and platforms that take 0% of their revenue.

https://DarkHorseEntrepreneur.com

Key Highlights

🚀 The Numbers That Matter:

  • Top 12 AI newsletters reach over 5 million combined subscribers

  • The Rundown AI: 2+ million subscribers generating 7 figures annually

  • Superhuman AI: 1.5+ million subscribers, hit 7 figures in just 4 months

  • Beehiiv platform: $30 million annualized revenue, sent 10 billion emails in 2024

💰 Major Acquisitions:

  • HubSpot paid $24 million for The Hustle (2021)

  • HubSpot acquired Mindstream AI newsletter (210K subscribers)

  • TechnologyAdvice bought The Neuron (500K subscribers)

You're absolutely right! Here's the timestamped key points section:


Key Points & Timestamps

00:00 - AI newsletters as most profitable side hustle
01:30 - Episode Overview
04:00 - Three Newsletter Success Stories
07:40 - Referral Program Statistics
08:20 - Why Beehiiv & Origin Story
10:20 - The 4 Newsletter Revenue Streams
12:55 - Then Content Strategy That works
14:45 - Growth Without Paid Advertising
16:05 - AI Content Creation Process
18:50 - Why This Matters Now
21:40 - Whiskered Wisdom: Consistency beats perfection


The Three Success Stories

1. The Milk Road - Crypto Newsletter Empire

2. The AI Newsletter Millionaires

The Rundown AI (Rowan Cheung):

Superhuman AI (Zain Kahn):

3. The No-Ads Success Stories

There's An AI For That: 1.7 million subscribers with $0 ad spend

The Beehiiv Advantage

Why Beehiiv Specifically:

  • Founded by Tyler Denk (Morning Brew's 2nd employee)

  • Helped scale Morning Brew to 3.5M subscribers → $75M exit

  • Takes 0% of subscription revenue (vs Substack's 10%)

  • 110,000+ publishers using platform

  • Industry-leading deliverability rates

Platform Features:

  • Built-in ad network

  • Cross-promotion marketplace (Boosts)

  • Referral programs

  • AI writing tools (GPT-4 powered)

  • SEO optimization

  • Free plan: 2,500 subscribers, unlimited sends

The Four Revenue Streams

1. Beehiiv Ad Network
2. Boosts Cross-Promotion
3. Paid Subscriptions
4. Affiliate Marketing

Content Strategy That Works

The Winning Formula:

  • Brevity: 3-5 minute read times

  • Frequency: Daily publishing builds habits

  • Focus: Practical applications over theory

  • Voice: Human perspective with AI assistance

AI Content Creation Process:

  1. Research: ChatGPT/Claude for trending topics

  2. Generation: AI drafts based on research

  3. Refinement: Add authentic voice and insights

  4. Optimization: AI-powered subject lines and social content

Action Steps

Week 1 Checklist:

  1. Sign up for Beehiiv's free Launch plan

  2. Choose your AI newsletter niche/angle

  3. Set up referral program with lead magnet

  4. Create first week of content using AI tools

  5. Commit to 90-day consistency plan

Key Quotes

"Whether you're writing to 10 people or 10 million people, it's the same amount of work." - Tyler Denk, Beehiiv Founder

"We launched on Beehiiv with nothing, scaled to over 250,000 subscribers, and got acquired, all in under a year." - The Milk Road Founder

Resources Mentioned

  • Beehiiv Platform: Free plan available

  • AI Tools: ChatGPT, Claude, Beehiiv's built-in GPT-4

  • Success Examples: The Rundown AI, Superhuman AI, The Milk Road

  • Case Studies: Write With AI, There's An AI For That, AI With Vibes

Episode Takeaway

The newsletter revolution is happening right now. The barrier to entry is essentially zero, the tools are built for you, and companies are paying millions for email lists because they understand email is the highest ROI marketing channel. The parents who start their AI newsletters this week will be celebrating their first thousand subscribers while everyone else is still thinking about it.

Remember: Consistency beats perfection every single time.

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AI newsletters are the most profitable
side hustle on the internet right now.

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00:00:04,469 --> 00:00:05,504
Yeah, I said what I said.

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00:00:05,782 --> 00:00:10,791
And the best ones are simple daily
emails written entirely by AI and

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00:00:10,791 --> 00:00:12,800
hosted on platforms like Beehiiv.

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00:00:13,060 --> 00:00:17,469
This AI newsletter side hustle feels,
I don't know, almost illegal to know

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00:00:17,469 --> 00:00:18,634
if you think about it, and here's why.

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00:00:18,965 --> 00:00:22,486
While you're trading hours for dollars
at your job, parents with zero written

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00:00:22,486 --> 00:00:26,330
experience are building seven-figure
newsletter empires from their kitchen

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00:00:26,330 --> 00:00:31,200
tables using nothing but AI tools and a
platform that takes 0% of their revenue.

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00:00:31,347 --> 00:00:32,156
Yeah, nothing.

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00:00:32,399 --> 00:00:36,834
The top 12 AI newsletters now reach
over five million combined subscribers.

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00:00:37,069 --> 00:00:41,904
Two of them, Rohan Chung's The
Rundown AI and Zain Kahn's Superhuman

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00:00:41,904 --> 00:00:46,208
AI, have crossed over two million
and 1.5 million subscribers

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respectively, and are generating
seven figures in annual revenue.

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00:00:50,278 --> 00:00:53,086
Superhuman AI hit seven
figures in just four months.

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But here's what no one in the
guru space wants you to know.

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Companies are literally paying millions
of dollars to acquire those email lists.

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HubSpot paid $24 million to Sam Parr's
The High Side Hustle back in 2021.

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00:01:04,756 --> 00:01:10,391
HubSpot acquired an AI newsletter called
Mindstream for its 210,000 subscribers,

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and TechnologyAdvice bought The Neuron
for its 500,000 su- subscribers.

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00:01:15,669 --> 00:01:18,182
The barrier to entry is essentially zero.

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The tools, they're already built for
you, and I'm about to walk you through

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exactly how this works from zero to
profitable AI newsletter, step-by-step.

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What is up?

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What is up?

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What the hell is up, my Dark
Horse friends and family?

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Welcome back to another episode of the
Dark Horse Entrepreneur AI Escape Plan,

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where we break free from the grind, share
some AI-powered tips and side hustle

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strategies, and support our parents
out there chasing freedom like the

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modern-day trailblazers that they are.

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And if you know someone who dreams of
ditching the grind while still making time

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for those lovable munchkins in their life,
go ahead and forward this episode to them.

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So let's go ahead and get stuck
right in here, and there's three

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things I want you to come away with.

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Obviously, what we're talking
about is how to start a highly

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profitable AI newsletter on Beehiiv.

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This is the side hustle I think
that feels almost illegal to know.

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But the three things I want you to
walk away with are the million-dollar

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subscriber blueprint, how Rowan Cheung's
The AI Rundown and Zane Khan's Superhuman

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AI have each surpassed a million
subscribers, and they're still growing.

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The Rundown AI now is at two
million subscribers, and Superhuman

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AI is at one point five million
as of, what, twenty twenty-five?

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I'm not sure of the updated figures.

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And they're generating seven figures
annually, with Superhuman hitting seven

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figures in revenue in just four months.

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Plus, why Beehiiv just hit thirty
million in annualized revenue.

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These are some very important
numbers I'm gonna share with you.

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Second, the acquisition gold rush.

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Why there are companies out there
that are paying millions for email

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lists, from examples like HubSpot's
twenty-seven million purchase of The

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Hustle to recent acquisitions of AI
newsletters with hundreds of thousands

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of subscribers, and how this proves
newsletters are having their Shopify

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moment, he says with air quotes.

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And then number three, the
zero to money playbook.

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This is the exact four-revenue stream
system that's generating life-changing

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income for newsletter creators out there,
including how two guys went from zero to

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eight-figure acquisition in ten months,
and why some newsletters are growing

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to one point seven million subscribers
without spending a single dollar in ads.

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But before we go down that road,
here's a truth I think that's

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gonna make some people in the
newsletter space very uncomfortable.

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The biggest wealth transfer
happening on the internet right

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now, I don't think it's in crypto.

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I don't think it's in real estate.

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I don't even think it's in AI startups.

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It's the simple email newsletters written
by AI and monetized through platforms

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that most people Have never heard of.

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While everyone's out there changing--
chasing the next shiny object, there

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are parents who are quietly building
million-dollar media empires one email

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at a time inside the booming creator
economy and digital publishing space.

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And the platform sitting at the center
of almost all of this success is Beehiiv.

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Let me tell you three stories I
think are gonna change how you

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think about making money online.

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Story number one: the crypto
newsletter that changed everything.

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I want you to picture this.

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It's January twenty twenty-two.

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Two guys decided they wanted to start
a newsletter about cryptocurrency.

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They have no current archive, they have
no subscribers, they have no audience,

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and they have no credibility in the space.

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Literally nothing.

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A big fat goose egg.

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They're starting from absolute zero
on a platform called Beehiiv that most

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people, maybe you, have not heard of.

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Their plan was simple, but
it was a little audacious.

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They called it The Milk Road, and they're
going to document the entire journey

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that they're gonna go on publicly.

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Let's fast-forward ten months.

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They built over two hundred and fifty
thousand subscribers and just sold their

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entire newsletter in an acquisition
estimated at eight-figure range.

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The Milk Road went from zero
to life-changing exit in less

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than a year, and they documented
every step of the process.

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Here's what makes this
story a bit remarkable.

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They spent about a hundred and eighty
thousand dollars on Facebook and Meta

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ads to drive over a hundred and fifty
thousand subscribers at roughly, what?

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A dollar to a dollar
thirty per sub-subscriber.

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It sounds like a lot of money
until you realize their primary ad

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slot was generating ten thousand
to twenty-five thousand dollars

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per email send at its peak.

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They were making their ad spend back In
every single newsletter that they sent.

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They tested creatives aggressively,
and they found that meme ads and

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social proof ads worked the best.

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But they weren't just
relying on paid advertising.

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One team member spent a few hours creating
a PDF called What Twelve Crypto Whales

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Are Betting On, and they offered it to any
reader who would refer just one person.

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That's it.

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Not ten, not five, not twenty.

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It was a dead simple referral program.

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What marketers called a lead magnet
strategy drove massive organic

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growth across their paid strategy.

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Their founder said it plainly when
he said, "We launched on Beehiiv with

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nothing. We scaled to over two hundred
and fifty thousand subscribers and

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got acquired in all under a year."

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End quote.

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Yeah, there it is.

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So here's story number two,
the AI newsletter millionaires.

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Now let me tell you about these two
newsletters that prove this wasn't

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just about crypto timing or luck.

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Rohan Chung launched The Rundown
AI as a daily five-minute briefing

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about artificial intelligence.

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Today, The Rundown AI has surpassed two
million subscribers, maintains over a

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fifty percent open rate, which is more
than double the industry average, which

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hovers around thirty-four percent, and it
generates seven figures every single year.

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Rohan runs daily five-minute
briefings that busy professionals

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will actually read because they're
practical and not theoretical.

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Let's talk about Zane Khan.

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Zane Khan took a different approach with
Superhuman AI, and he's focusing on how

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to use AI tools to become more productive.

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Superhuman AI has now crossed one point
five million subscribers and generates

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seven figures every single year.

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Now, here's the part that
should get your attention.

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Superhuman AI hit seven
figures in four months.

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Four months from launch
to seven-figure revenue.

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Zero to seven figures.

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Let that sink in for a moment, would you?

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Both of these newsletters follow the
same pattern: daily publishing, three

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to five-minute read times, practical
focus over theory and wah-wah and loo-loo

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stuff out there, and AI-powered content
creation that scales without burning out

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the creator behind the scenes, right?

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Now, here's story number three, the no-ads
success story, 'cause I know you might be

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thinking, "Yeah, that's great, Tracy, but
I don't have money for Facebook ads like

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The Milk Road." Here's the beautiful part.

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You don't need to.

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An AI let- newsletter called There's an
AI for That grew to over one point seven

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million subscribers without spending
one single dollar on paid advertising.

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They built their entire audience through
organic growth, referral programs,

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and platform discovery features.

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Another newsletter called AI with
Vibes got acquired in just seven months

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using similar organic strategies.

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The data backs this up.

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Referral programs boost subscriber
growth about an average of seventeen

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percent, and referred subscribers
have a sixteen percent higher

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retention rate with acquisition costs
up to ninety-two percent lower than

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all the paid channels out there.

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Morning Brew's referral program alone
drove over a million subscribers

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before they sold to Business Insider.

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These aren't just
isolated success stories.

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I think they're proof of a systematic
approach to building wealth through

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email that's now powered by AI tools that
didn't exist just a couple of years ago.

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So now that you've got the numbers and
some of the, uh, the statistics to help

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prove this is not me just blowing smoke
up your butt, let me break down how to

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build this business step by step using
all the data from these success stories.

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One, why should you use
Beehiiv s-specifically?

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Well, Beehiiv was founded in twenty
twenty-one by, by Tyler Denk, who

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joined Morning Brew back in twenty
seventeen, uh, as their second employee.

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He helped scale that newsletter to
three point five million subscribers

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before it sold to Business In-Insider
for seventy-five million bucks.

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Then he took everything he learned
about what works in newsletter growth,

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and he built Beehiiv as the platform
he wished he had at the Morning Brew.

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Today, over a hundred and ten
thousand publishers use Beehiiv,

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including this podcaster here.

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And as of twenty twenty-five, the platform
hit thirty million in annualized revenue.

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In twenty twenty-four alone, Beehiiv
sent over ten billion, with a B, emails,

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with industry-leading deliverability
rates that keep your content Out of

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those pesky spam folders out there.

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Now, that's just not growth, that's
really explosive adoption by serious

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newsletter creators, perhaps like you.

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I know it's certainly like me.

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Here's the key difference between
Beehiiv and competitors like Substack,

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founded by Chris Best, which takes
about ten percent of every paid

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subscription right off the top.

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And then there's ConvertKit,
which has now been rebranded

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as Kit, Mailchimp, and Ghost.

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Beehiiv takes zero percent of
your paid subscription revenue.

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Nothing.

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Zero.

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Nada.

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Big fat goose egg.

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You keep everything you earn.

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Well, you know, of course, minus
any Stripe processing fees.

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The ten percent Substack charges
compounds fast when you're scaling,

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00:09:39,595 --> 00:09:43,456
and platforms like Mailchimp and
ConvertKit, now known as Kit, are really

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built for general email marketing,
not for the newsletter creator economy

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the way that Beehiiv specifically is.

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And, and on top of all of that, Beehiiv
gives you a built-in ad network, a

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cross-promotion marketplace, uh, called
Boost, which is referral programs.

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AI writing tools are in
there and SEO optimization.

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This is all under the same roof.

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You don't need to go find all
these tools out there and start

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trying to piece them together.

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The best part for getting started
is this: the free plan gives you up

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00:10:09,847 --> 00:10:13,273
to twenty-five hundred subscribers
with unlimited email sends.

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You don't pay a dime until
you're ready to scale past that.

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Okay?

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Step two, the four revenue streams
that create seven-figure newsletters.

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Based on the success stories I've
analyzed, there are four primary

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ways to monetize your AI newsletter
on Beehiiv, and the most successful

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creators out there are using all four.

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Revenue stream number one
is the Beehiiv ad network.

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Once you hit a thousand
subscribers, Beehiiv starts

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sending you ad opportunities
from their premium advertisers.

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They go out there and find the
advertisers, they bring them in,

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and they start sending them to you.

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00:10:42,978 --> 00:10:46,143
And you're looking at five
to twenty dollar SCPMs here.

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That's cost per thousand impressions.

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On weekly sends, which translate to maybe,
I don't know, twenty to a hundred and

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00:10:51,326 --> 00:10:55,065
sixty bucks a month at just one thousand
subscribers with a good open rate.

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A single ad could bring you
fifty to a hundred bucks.

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Okay?

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00:10:57,647 --> 00:11:00,056
That's, I mean, it's not life-changing
money, but certainly good to know.

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00:11:00,117 --> 00:11:01,847
I want you to remember
The Milk Road numbers.

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Their primary ad slot was generating
ten thousand to twenty-five thousand

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00:11:06,439 --> 00:11:10,108
per cent at its peak when they had two
hundred and fifty thousand subscribers.

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That's the power of this
revenue stream at scale.

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Revenue stream number two.

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00:11:14,408 --> 00:11:15,956
This is Boost's cross-promotion.

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00:11:16,043 --> 00:11:20,226
Beehiiv's cross-promotion marketplace
is where you get paid to recommend

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00:11:20,286 --> 00:11:22,182
other newsletters to your audience.

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00:11:22,373 --> 00:11:26,086
The average cost per subscriber in the
Boost network is a buck sixty-three,

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00:11:26,269 --> 00:11:30,426
meaning other publishers out there
will pay you every time one of your

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readers subscribes to their newsletter.

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Sounds pretty simple.

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And this is passive income.

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You write one recommendation,
and you get paid every time

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00:11:37,939 --> 00:11:39,634
someone clicks and subscribes.

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00:11:39,713 --> 00:11:42,008
Revenue stream number
three, paid subscriptions.

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00:11:42,191 --> 00:11:46,356
Even at a, let's say, a modest one
to three percent conversion rate from

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00:11:46,356 --> 00:11:50,434
a free reader to a paid subscriber
can create substantial recurring

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00:11:50,434 --> 00:11:54,382
revenue, and Beehiiv takes none of
that, as I, as I keep telling you.

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Zero.

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00:11:54,930 --> 00:11:58,478
Based on the twenty twenty-five data,
paid subscriptions generated about

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00:11:58,556 --> 00:12:03,582
eight point seven million across
newsletters on Beehiiv, with a ninety-six

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00:12:03,626 --> 00:12:05,600
point two growth year over year.

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So it's growing.

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00:12:06,599 --> 00:12:07,304
It's getting bigger.

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00:12:07,426 --> 00:12:11,939
Write with AI is a newsletter on
Substack It reached $400,000 in annual

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00:12:11,939 --> 00:12:16,530
recurring revenue in 2025 by launching
quarterly digital products that generated

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00:12:16,530 --> 00:12:21,460
$90,000 from a single drop, plus
founding member offers that brought in

247
00:12:21,460 --> 00:12:24,208
an extra $25,000 in just two months.

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Okay?

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00:12:24,808 --> 00:12:27,791
So this-- there's some big numbers
that can go with paid subscriptions.

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And then revenue stream number
four is affiliate marketing.

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Most of us know about this, but
promoting AI tools, uh, software,

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00:12:34,382 --> 00:12:39,147
courses to your audience can generate
100 to $1,000 a month, even when

253
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you only have 1,000 subscribers.

254
00:12:41,017 --> 00:12:43,765
When you scale this, this
becomes much more significant.

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00:12:43,765 --> 00:12:45,295
It has an opportunity to grow even bigger.

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00:12:45,356 --> 00:12:49,234
Stack all four of these together, and
the m-math starts to look very, very

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00:12:49,234 --> 00:12:51,626
good, very, very real, very, very fast.

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00:12:51,721 --> 00:12:54,486
Step three is the content
strategy, and here's a content

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00:12:54,486 --> 00:12:56,104
strategy that actually works.

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00:12:56,304 --> 00:12:59,808
The most successful AI newsletters
follow consistent patterns that

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you can replicate, and here are
some of those consistent patterns.

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Number one is brevity.

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My friends, brevity wins.

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A three-to-five-minute read dominates
because busy professionals simply

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don't have time out there anymore.

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They, they won't read
longer content consistently.

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00:13:14,739 --> 00:13:17,869
They may read it every once in a while,
but you want them to be reading-- opening

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your emails and reading them consistently.

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00:13:19,452 --> 00:13:23,860
Both the Rundown AI and Superhuman
AI stick to this format religiously.

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Daily publishing is another big win.

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Daily publishing builds stronger reader
relationships than weekly publishing

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00:13:29,895 --> 00:13:32,460
does because you're creating a habit.

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Your newsletter becomes a part of
their morning routine, their afternoon

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00:13:36,556 --> 00:13:40,530
break, whatever it is, not something
they might get to later on, right?

275
00:13:40,608 --> 00:13:41,843
'Cause we know what happens then.

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They tend not to do it.

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00:13:42,826 --> 00:13:46,095
The next piece of the content
strategy is practical focus.

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Practical focus is gonna beat
theory's ass every single time.

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Readers want to know how to
use AI in their work, not just

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what's theoretically possible.

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00:13:56,260 --> 00:14:00,147
And if you're not doing a newsletter about
AI, whatever it is you're talking about,

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they wanna know the hows of how they
can use it, not just the theories in it.

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00:14:05,008 --> 00:14:09,947
The newsletters that survive and thrive
solve real problems With actionable

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00:14:10,000 --> 00:14:12,486
advice in that three-to-minute brief read.

285
00:14:12,521 --> 00:14:15,426
This is where AI becomes, I
think, your unfair advantage.

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00:14:15,617 --> 00:14:21,078
Beehiiv has built-in AI tools powered by
GPT-4 that can handle draft headlines,

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00:14:21,426 --> 00:14:23,652
sections, and even full newsletters.

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00:14:23,982 --> 00:14:27,513
You can use Claude for some long-form
drafting and research, and then edit

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00:14:27,547 --> 00:14:30,043
and refine to keep your authentic voice.

290
00:14:30,417 --> 00:14:34,190
The content creation process that
used to take hours with research

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00:14:34,243 --> 00:14:38,104
included now has just been compressed
all the way down to minutes.

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00:14:38,330 --> 00:14:40,365
Okay, maybe let's say 20 minutes.

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00:14:40,573 --> 00:14:40,834
All right.

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00:14:40,904 --> 00:14:41,947
So you, you see what I'm saying.

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00:14:42,000 --> 00:14:44,573
You've gone from hours to
almost less than a half hour.

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00:14:44,869 --> 00:14:47,913
Now, step number four is growth
without paid advertising.

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00:14:48,017 --> 00:14:51,321
Here's where the success stories from
the newsletters There's an AI for

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00:14:51,408 --> 00:14:54,173
that, and AI was vibes become crucial.

299
00:14:54,208 --> 00:14:59,120
You don't need $180,000 in ad spend
like The Milk Road to build this massive

300
00:14:59,147 --> 00:15:00,713
subscriber list for your newsletter.

301
00:15:00,721 --> 00:15:02,817
The data on organic growth
is very, very clear.

302
00:15:03,147 --> 00:15:07,260
Referral programs boost subscriber
growth an average of 17%.

303
00:15:07,686 --> 00:15:10,313
Referred subscribers have
a higher retention rate.

304
00:15:10,347 --> 00:15:12,346
It's about 16% higher retention rate.

305
00:15:12,556 --> 00:15:17,095
Acquisition costs are up to
92% lower than paid channels.

306
00:15:17,321 --> 00:15:17,756
It's cheaper.

307
00:15:18,086 --> 00:15:18,260
Get it?

308
00:15:18,539 --> 00:15:19,234
Duh, of course.

309
00:15:19,373 --> 00:15:22,713
And then Morning Brew's referral
program alone, in the example I gave you

310
00:15:22,973 --> 00:15:25,043
ear-earlier, drove a million subscribers.

311
00:15:25,139 --> 00:15:29,547
Set up a referral pr-program on day
one using Beehiiv's built-in tools.

312
00:15:29,756 --> 00:15:33,443
Create a simple lead magnet, you know, a,
a PDF checklist, a template, whatever it

313
00:15:33,513 --> 00:15:38,243
is, and offer it to anyone that refers and
gets one person to sign up on your list.

314
00:15:38,608 --> 00:15:39,304
That's it, right?

315
00:15:39,373 --> 00:15:41,904
That's exactly what Milk Road
did with their What Twelve

316
00:15:42,017 --> 00:15:43,860
Crypto Whales Are Betting On.

317
00:15:43,895 --> 00:15:47,286
That, that was their PDF, and
it drove massive organic growth.

318
00:15:47,582 --> 00:15:52,939
Write with AI is gaining over 1,000 s-new
subscribers every single week, with 35% of

319
00:15:52,973 --> 00:15:57,339
their subscribers coming directly from the
platform's built-in discovery features.

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00:15:57,565 --> 00:16:00,973
That is the power of consistent
quality content on a platform

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00:16:01,304 --> 00:16:02,817
that promotes good newsletters.

322
00:16:03,104 --> 00:16:04,208
And that brings us to step five.

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00:16:04,365 --> 00:16:06,678
This is the AI content creation process.

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00:16:07,299 --> 00:16:10,169
Here's where it gets, I know, really
powerful for my busy parents out

325
00:16:10,169 --> 00:16:11,482
there, for all my busy entrepreneurs.

326
00:16:11,673 --> 00:16:15,691
The content creation process that used
to take hours now gets compressed down

327
00:16:15,691 --> 00:16:17,821
into minutes with the right AI flow.

328
00:16:17,856 --> 00:16:21,230
Now, don't get me wrong here, you-- I'm
gonna tout AI's benefits, but you wanna

329
00:16:21,230 --> 00:16:23,995
use things right, like I've mentioned
in a, a couple of previous episodes.

330
00:16:24,369 --> 00:16:25,404
Gonna have a research phase.

331
00:16:25,665 --> 00:16:29,969
Let's use ChatGPT or Claude to
research trending topics and trending

332
00:16:30,030 --> 00:16:32,326
tools and news in your niche.

333
00:16:32,439 --> 00:16:32,647
All right?

334
00:16:33,108 --> 00:16:35,073
Then you're gonna go
into content generation.

335
00:16:35,247 --> 00:16:39,308
Work with AI to draft your newsletter
sections based on your research.

336
00:16:39,439 --> 00:16:40,856
Now you need voice refinement.

337
00:16:40,986 --> 00:16:45,100
You wanna edit it for your authentic
voice, and then add your human

338
00:16:45,100 --> 00:16:46,952
touch and your personal insights.

339
00:16:47,134 --> 00:16:48,213
And then optimization.

340
00:16:48,256 --> 00:16:53,334
Use AI to create optimized subject
lines, optimize for things like open

341
00:16:53,334 --> 00:16:56,560
rates and click-through rates, and
then, of course, you wanna use that als-

342
00:16:56,639 --> 00:17:00,352
uh, use AI also to help you generate
some social media promotional content.

343
00:17:00,560 --> 00:17:03,317
And here's the key that
separates successful newsletters

344
00:17:03,508 --> 00:17:05,091
from AI content mills.

345
00:17:05,152 --> 00:17:07,482
Don't let AI write everything.

346
00:17:07,647 --> 00:17:11,543
The most successful newsletters
continue to this day to maintain a

347
00:17:11,543 --> 00:17:13,360
human voice and a human perspective.

348
00:17:13,578 --> 00:17:15,543
AI, yeah, will handle the research.

349
00:17:15,586 --> 00:17:15,700
Yeah.

350
00:17:15,952 --> 00:17:19,517
AI is gonna handle the first
draft, and AI is obviously better

351
00:17:19,517 --> 00:17:20,830
to handle the optimization.

352
00:17:21,065 --> 00:17:23,613
What you should do is you
should handle the strategy, the

353
00:17:23,613 --> 00:17:25,334
voice, and the final polish.

354
00:17:25,517 --> 00:17:29,673
Rowan Cheung from The Rundown AI and
Zane Khan from Superhuman AI both

355
00:17:29,699 --> 00:17:34,508
use AI extensively in their content
creation process, but their newsletters

356
00:17:34,647 --> 00:17:38,265
feel distinctly human because they add
their own insights, they add their own

357
00:17:38,265 --> 00:17:43,030
experiences, and they add their own
perspectives into every single issue.

358
00:17:43,178 --> 00:17:43,369
All right?

359
00:17:43,647 --> 00:17:46,613
So if you're ready to build an
AI-powered side hustle that could

360
00:17:46,613 --> 00:17:50,786
scale to seven figures or whatever
it is that you need, all while still

361
00:17:50,786 --> 00:17:54,795
protecting your family time, the AI
Escape Plan Newsletter is your roadmap.

362
00:17:54,795 --> 00:17:56,126
What a perfect match this is, right?

363
00:17:56,169 --> 00:17:59,978
Each issue delivers practical, tested
strategies to start and grow and

364
00:17:59,978 --> 00:18:03,830
streamline side hustles using AI,
artificial intelligence, all designed

365
00:18:03,830 --> 00:18:07,917
to help work around your parenting
schedule, not despite that schedule.

366
00:18:07,952 --> 00:18:10,621
We cover everything from, from AI
newsletter strategies like the one

367
00:18:10,621 --> 00:18:13,604
we're discussing today, to automation
tools that can save you hours, to

368
00:18:13,604 --> 00:18:17,160
au- monetization methods that can
generate income while you're sleeping.

369
00:18:17,221 --> 00:18:18,126
Actually, it's even better.

370
00:18:18,126 --> 00:18:20,517
It can generate you income while
you're outside playing with your kids.

371
00:18:20,795 --> 00:18:23,021
It is your complete guide to
more money, more freedom, and

372
00:18:23,021 --> 00:18:24,613
more of what truly matters.

373
00:18:24,882 --> 00:18:28,665
The entrepreneurs who build AI
newsletters the right way Aren't

374
00:18:28,708 --> 00:18:29,943
just creating side income.

375
00:18:30,299 --> 00:18:34,030
They're building mini media companies
and digital publishing empires

376
00:18:34,317 --> 00:18:37,421
that could potentially be sold
for millions while they're still

377
00:18:37,421 --> 00:18:38,447
working from their kitchen table.

378
00:18:38,447 --> 00:18:42,517
So whether you're writing to ten people or
ten million, it's the same amount of work.

379
00:18:42,830 --> 00:18:46,334
That's the leverage of newsletters
that Taylor Dink discovered in the

380
00:18:46,334 --> 00:18:48,369
Morning Brew and built into Beehive.

381
00:18:48,656 --> 00:18:51,908
So let's step back for a moment and,
and talk about what's really happening

382
00:18:51,908 --> 00:18:55,865
here at a macro level and why I
think this opportunity isn't gonna

383
00:18:55,865 --> 00:18:57,934
last forever in its current form.

384
00:18:58,013 --> 00:19:01,691
Now, as Packy McCormick, the founder
of the Not Boring newsletter, put it,

385
00:19:01,873 --> 00:19:06,265
"Email newsletters are having their
Shopify moment. Just as Shopify made it

386
00:19:06,265 --> 00:19:10,056
easy for anyone to open up an e-commerce
store, newsletter platforms are

387
00:19:10,056 --> 00:19:12,795
democratizing media ownership." Unquote.

388
00:19:12,978 --> 00:19:13,152
Right?

389
00:19:13,421 --> 00:19:16,778
We're witnessing the collision of
several massive trends right now.

390
00:19:17,108 --> 00:19:19,995
The acquisition trend, there are
companies that understand that email

391
00:19:19,995 --> 00:19:24,273
lists are the highest ROI marketing
channel that exists on the planet, have

392
00:19:24,273 --> 00:19:25,865
been for a long time, continue to be so.

393
00:19:26,195 --> 00:19:29,308
HubSpot paid twenty-seven million
for Sam Parr's Dossel back in

394
00:19:29,308 --> 00:19:32,204
twenty-twenty-one, proving that
newsletters are valuable assets.

395
00:19:32,308 --> 00:19:36,465
More recently, HubSpot acquired another
AI newsletter called Mindstream for its

396
00:19:36,465 --> 00:19:40,665
two hundred and ten thousand subscribers,
and TechnologyAdvice bought The Neuron

397
00:19:40,665 --> 00:19:42,804
for its five hundred thousand subscribers.

398
00:19:42,969 --> 00:19:47,282
Every email address is worth
approximately one to three bucks in

399
00:19:47,282 --> 00:19:52,621
acquisition value, but the lifetime
value can be ten to fifty x that amount.

400
00:19:52,882 --> 00:19:54,952
Then there's a growth
expansion trend going on.

401
00:19:54,952 --> 00:19:57,360
The newsletter industry grew
ninety-six percent year over

402
00:19:57,360 --> 00:20:00,221
year between twenty-twenty-three
and twenty-twenty-five.

403
00:20:00,317 --> 00:20:03,943
Over three thousand AI newsletters have
been launched in the past two years,

404
00:20:04,169 --> 00:20:07,978
but only five have cracked a hundred
thousand subscribers consistently.

405
00:20:08,252 --> 00:20:10,695
The opportunity is massive,
and the competition at the

406
00:20:10,695 --> 00:20:12,678
top is really thin right now.

407
00:20:12,965 --> 00:20:14,460
And then there's the AI advantage.

408
00:20:14,591 --> 00:20:18,539
AI tools have collapsed the content
creation barrier that used to

409
00:20:18,539 --> 00:20:21,800
keep most people like you and me
out of the newsletter business.

410
00:20:21,826 --> 00:20:22,591
It takes time.

411
00:20:22,834 --> 00:20:26,069
I started two newsletters way back
in the late '90s and would dedicate

412
00:20:26,104 --> 00:20:29,678
hours to getting good content
out there, so it was just weekly.

413
00:20:29,756 --> 00:20:30,495
I couldn't do it daily.

414
00:20:30,791 --> 00:20:31,704
Now it's a lot easier.

415
00:20:31,852 --> 00:20:35,469
What used to require a team of writers
and researchers can now be done by

416
00:20:35,495 --> 00:20:38,356
one person with the right AI workflow.

417
00:20:38,678 --> 00:20:42,869
And I think finally, the last factor
here is the platforms have matured.

418
00:20:43,365 --> 00:20:46,504
Beehiiv's growth to thirty million
in annualized revenue as of

419
00:20:46,739 --> 00:20:52,652
last year, 2025, and ten billion
emails sent in 2024 shows that the

420
00:20:52,652 --> 00:20:57,130
infrastructure for newsletter success
is now mature, and it's now proven.

421
00:20:57,200 --> 00:21:00,513
Compare that to building on,
say, MailChimp or ConvertKit,

422
00:21:00,573 --> 00:21:01,756
which I've built on both.

423
00:21:01,878 --> 00:21:03,260
Night and day, trust me on this one.

424
00:21:03,504 --> 00:21:08,086
They simply aren't designed for the
creator economy model as it sits today.

425
00:21:08,286 --> 00:21:11,356
All these factors create this massive
opportunity for entrepreneurs or

426
00:21:11,356 --> 00:21:15,295
parents like you and me who understand
how to build AI newsletters correctly.

427
00:21:15,513 --> 00:21:19,626
While the market gets flooded with
all the low-quality AI slop content

428
00:21:19,626 --> 00:21:24,086
out there, there is a growing
demand for trustworthy, practical AI

429
00:21:24,086 --> 00:21:25,956
newsletters that you could create.

430
00:21:26,208 --> 00:21:30,521
The parents who position themselves as
that reliable, valuable alternative,

431
00:21:30,930 --> 00:21:34,913
they're not just building businesses,
they're building monopolies in markets

432
00:21:34,939 --> 00:21:37,973
desperate for honest, helpful content.

433
00:21:37,973 --> 00:21:41,399
So all that said, here's your
Whiskered Wisdom for this episode.

434
00:21:41,652 --> 00:21:45,878
Tyler Denk captured why this model
is so powerful when he said, "Whether

435
00:21:45,878 --> 00:21:48,852
you're writing to ten people or ten
million people, it's the same amount of

436
00:21:48,852 --> 00:21:53,217
work." That, my friends, as I repeat to
myself, is the leverage of newsletters.

437
00:21:53,382 --> 00:21:58,147
Your effort stays constant while your
income scales with your audience.

438
00:21:58,365 --> 00:22:00,513
But here's what Tyler learned
at The Morning Brew that

439
00:22:00,547 --> 00:22:02,173
most people are gonna miss.

440
00:22:02,339 --> 00:22:05,826
Consistency beats perfection's
butt every single time.

441
00:22:06,078 --> 00:22:10,930
The Rundown AI, Superhuman AI, The
Milk Road, they all succeed because

442
00:22:11,147 --> 00:22:15,530
they showed up every single day with
valuable content, not because they waited

443
00:22:15,530 --> 00:22:17,043
until they had the perfect newsletter.

444
00:22:17,226 --> 00:22:19,339
So here's your specific
action for this week.

445
00:22:19,695 --> 00:22:22,886
Go out there, sign up for
Beehiiv's free launch plan today.

446
00:22:22,886 --> 00:22:24,800
I'll drop a link for it
down in the show notes.

447
00:22:25,139 --> 00:22:30,617
Pick your AI newsletter angle, whether
it's AI tool roundups or industry-specific

448
00:22:30,617 --> 00:22:33,982
applications, tutorials or daily news,
or maybe you're gonna go off on an

449
00:22:33,982 --> 00:22:35,391
entirely different topic altogether.

450
00:22:35,521 --> 00:22:39,217
Find your lane and then
commit to it for ninety days.

451
00:22:39,591 --> 00:22:43,321
Use AI tools like ChatGPT, uh,
or Claude, I like Claude a little

452
00:22:43,321 --> 00:22:47,773
bit better, to help you curate and
create your first week of content.

453
00:22:47,921 --> 00:22:50,721
Keep it short, keep it practical,
and keep it consistent.

454
00:22:51,165 --> 00:22:54,626
And then set up a simple referral
program offering a valuable lead

455
00:22:54,626 --> 00:22:58,765
magnet to anyone who refers one person
that signs up to your newsletter.

456
00:22:59,052 --> 00:23:02,234
That single action could be the
difference between slow organic

457
00:23:02,234 --> 00:23:05,304
growth or explosive viral growth.

458
00:23:05,365 --> 00:23:09,999
The most consistent creators reach 10,000
subscribers within six to 12 months.

459
00:23:10,086 --> 00:23:13,417
At that level, with the multiple
monetization streams that

460
00:23:13,417 --> 00:23:16,208
I've mentioned earlier, you're
generating real side income.

461
00:23:16,408 --> 00:23:19,313
At scale, the numbers get
genuinely life-changing.

462
00:23:20,208 --> 00:23:21,469
Remember Superhuman AI?

463
00:23:21,747 --> 00:23:24,173
They hit seven figures within four months.

464
00:23:24,365 --> 00:23:28,469
The only question is whether you start
today or you go ahead and you watch

465
00:23:28,469 --> 00:23:31,878
someone else build the l- the newsletter
that you could've built, or that

466
00:23:31,878 --> 00:23:32,991
you're thinking of building right now.

467
00:23:33,252 --> 00:23:36,704
Look, the, the newsletter revolution
is happening right this minute,

468
00:23:37,034 --> 00:23:40,269
and it's powered by AI tools that
make content creation faster, and

469
00:23:40,269 --> 00:23:43,982
it has platforms like Beehiiv that
make monetization almost automatic.

470
00:23:44,295 --> 00:23:47,469
While everyone else is chasing the
latest trend, I want you to be one of

471
00:23:47,469 --> 00:23:50,173
the smart entrepreneurs, one of the
smart, smart parents out there that

472
00:23:50,173 --> 00:23:53,808
are quietly building their own little
media empire one email at a time.

473
00:23:54,121 --> 00:23:57,643
This side hustle feels almost
illegal to know because the barrier

474
00:23:57,643 --> 00:23:59,382
to entry is essentially zero.

475
00:23:59,643 --> 00:24:01,113
The tools are already built for you.

476
00:24:01,139 --> 00:24:05,243
The market is growing faster than anyone
can keep up with, and companies are paying

477
00:24:05,243 --> 00:24:09,321
millions for email lists because they
already understand what most people miss.

478
00:24:09,504 --> 00:24:14,973
Email is the highest ROI marketing channel
that exists today, and AI just made it

479
00:24:14,973 --> 00:24:17,199
completely accessible to you, to everyone.

480
00:24:17,530 --> 00:24:18,973
The opportunity is massive.

481
00:24:19,130 --> 00:24:22,217
The competition is thin, and
the potential for life-changing

482
00:24:22,217 --> 00:24:23,573
income, I think it's real.

483
00:24:23,808 --> 00:24:27,747
Rohan Chung, Zain Khan, and the founders
of Milk Road, they weren't special.

484
00:24:27,991 --> 00:24:31,756
They just started before everyone else
realized what was actually possible.

485
00:24:32,069 --> 00:24:35,017
But like every real
opportunity, it requires action.

486
00:24:35,417 --> 00:24:39,391
It re- and it, it, yeah, it requires
consistency, and yeah, it requires

487
00:24:39,391 --> 00:24:41,478
starting before you feel ready.

488
00:24:41,600 --> 00:24:45,713
The entrepreneurs and parents who start
their AI newsletters this week will be

489
00:24:45,713 --> 00:24:49,939
the ones celebrating their first thousand
subscribers, their first ad revenue check,

490
00:24:50,269 --> 00:24:53,791
and their first acquisition offer, while
everyone else is still out there going,

491
00:24:54,034 --> 00:24:55,678
"Hmm, I wonder if I should do it or not."

492
00:24:55,782 --> 00:24:57,026
Yeah, they'll still be thinking about it.

493
00:24:57,260 --> 00:24:57,973
You get going.

494
00:24:58,486 --> 00:25:00,878
You think successfully,
and you take action.