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📰 newsletter overview
🧪 what I'm building: outreach systems & prioritizing high leverage tasks
🚨 big news: beehiiv’s on demand ads, you can now monetize any issue instantly
🤖 AI tools & skills: scrape, crawl, and extract from any site in seconds with this tool
🛠️ tutorial of the week: write 5 email welcome sequences with AI in one sitting
🎙️ podcast vault: what beehiiv's CEO revealed about launching, growing, and monetizing a newsletter to 120k subs
📊 founder newsletter breakdown: how Sam Parr built The Hustle to 1.5m subs and sold it to HubSpot for $27m
🧪 what I'm building
This week was about focus.
Wrapped up a big client project.
Outreach is going out daily, with a mix of high value manual DMs, Looms, and automated emails.
The numbers aren't where they need to be yet, so I'm not scaling anything. No point flooding a leaky system.
But volume is building, and we're getting close.
Outside of client work, I've been journaling more, sitting with the business and asking harder questions instead of just moving fast.
The biggest shift: 3 priorities per week, max. Not ten. Not five. Three.
If it's not generating revenue, it doesn't get my time.
That one filter has moved the needle more than any tactic I've tried.
Right now, the only two things that matter are outbound and managing inbound.
Everything else is noise dressed up as productivity.
Simple. Boring. Working.
🚨 big news
beehiiv launches on demand ads
Beehiiv just dropped a feature that changes how newsletter creators monetize: on demand ads.
Instead of waiting around for a sponsor to reach out (or cold pitching brands yourself), you can now browse premium ad opportunities directly inside the beehiiv editor.
New campaigns refresh every hour.
You pick the one that fits your audience, drop it into your newsletter, and send.
Once you select an ad, you have 5 days to send it and you can move ads between drafts.
Performance reports land 96 hours after your send and earnings deposit on the 20th of each month.
why this matters
Beehiiv launched their ad network 18 months ago.
Newsletters on the platform now collectively earn over $1m/ month from brands like Netflix, HubSpot, Nike, AG1, and Roku.
Before this, the ad network matched you with sponsors behind the scenes.
Now you have direct access.
You see what's available, you pick what makes sense for your readers, and you get paid.
what to take away
If you're running a newsletter and you've been putting off monetization because you don't have sponsor relationships or a sales process, this removes that barrier entirely.
You don't need 100k subs to start earning.
You can do it with a paid beehiiv plan and an audience that opens your emails.
The sponsors are already there.
You just pick one.
🤖 ai tools & skills
scrape, crawl, and extract from any site in seconds with this tool
Recently, a main focus of mine has been outreach at scale.
One of the problems with this is that when you're reaching out to 300+ leads/ day, you're forced to send a generic pitch to everyone.
Ideally, every email feels like it was written just for them, but that's obviously not realistic at volume. I've been testing a few solutions to this, and I want to share one that I think has serious potential.
It's called firecrawl, some of you might already know it, but for those who don't firecrawl turns any website into clean, structured data with a single API call.
You give it a url and it gives you back markdown, JSON, whatever format you need.
It handles JavaScript rendered pages, anti bot protections, proxies, etc.
But here's where it gets interesting for agency owners, creators, or anyone doing research at scale.
Pair firecrawl with any AI model, and you've essentially got automated research.
The workflow I'll be testing looks like this:
scrape a prospect's entire site with firecrawl
feed that data into an AI model, and get a full breakdown (their gaps, what's underperforming, etc)
Then I use that intel to write a personalised email intro, call out specific weak points in their business, or prep for a sales call with context.
🛠️ tutorial of the week
use AI to write a 5 email welcome sequence in one sitting
Most newsletters have no welcome sequence.
Someone subscribes and the next thing they hear from you is whenever you get around to sending the next letter.
You’re leaving money and engagement on the table like this.
A welcome sequence does three things:
builds trust
sets expectations
moves new subscribers toward your offer.
Here's how to write all five emails in one sitting using AI.
step 1: give AI the context about your newsletter
Open your preferred AI and paste this prompt, filling in your details:
I run a newsletter about [topic] for [audience]. My tone is [conversational/professional/casual].
I publish [frequency]. My main offer is [product/service/community].
Write a 5 email welcome sequence with these goals:
- Email 1: Welcome, set expectations, deliver any lead magnet
- Email 2: Share my best piece of content or biggest insight
- Email 3: Tell my story and why I started this
- Email 4: Provide a quick win or actionable framework
- Email 5: Soft intro to my offer with a clear CTA
Keep each email under 300 words. Sound like a real person, not a marketer.
step 2: review and add your voice
Claude will give you five solid drafts.
Read them out loud, and if it sounds generic anywhere, swap in your own stories, numbers, or examples.
The structure should stay, but the personality needs to be yours.
Pro Tip: Give the AI some of your best performing posts/ newsletters and tell it to "match this voice."
step 3: tighten the subject lines
Ask it to generate 3 subject line options per email, pick the ones that sound like something you'd actually open.
step 4: set up the automation
In beehiiv, go to Automations and create a new sequence triggered by "new subscriber."
Set each email to send 1 day apart and paste in your final drafts.
If you're on another platform, the setup is similar.
step 5: test it on yourself
Subscribe with a personal email and read every email as a new subscriber would.
Check that links work, formatting looks right on mobile, and nothing reads like it was written by a robot.
Or you can ask a friend to test it for you.
🎙️ podcast vault
how beehiiv's CEO built 120K subscribers on the side
Tyler Denk is the CEO of beehiiv.
He also writes a newsletter called Big Desk Energy.
It has 120k subs, he publishes every Tuesday, and he says it might bring in more revenue than his full time job running a $30m ARR company.
He broke down exactly how he built it in a recent conversation with Matt McGarry.
And 3 things stood out to me.
his launch strategy was simple and gritty
Tyler announced the newsletter in December 2023.
He said he wouldn't send the first issue until he hit 1k subs.
He promoted it every few days on X and LinkedIn until he crossed that number, then launched in January 2024.
From there, his growth was a grind:
Every Monday night, he previews the next issue's topic on social. "If you want to be the first to read it, subscribe here." That alone brings in a few dozen subscribers per post.
Every Tuesday after sending, he posts a summary that leaves out key details. If the issue covers five things beehiiv looks for when hiring, he shares three and says, "for the last two, subscribe here."
Every post on the beehiiv site uses an email gate. You can read the first few sentences, but you have to enter your email to read the rest. If someone clicked from social, they're interested enough to convert.
He runs a referral program from day one. His first reward: the unedited Series B deck beehiiv used to raise $33m. Cost to him nothing. His second reward: 20% off merch (he still breaks even on the discounted price). Also, cost to him nothing.
He has a VA send a LinkedIn connect request and newsletter signup link to every new beehiiv user, getting 15 to 25 subscribers per week, every week, for two years straight.
No single tactic was a silver bullet here, all of them compounded over time to get him to 120k subs.
his take on AI and the future of email
Tyler made a point that I understand:
Trust is becoming the scarcest resource online.
Anyone can vibe code a competing product in a weekend (maybe).
When everything is easy to create, the thing that becomes valuable is knowing who to trust.
That's why founder led newsletters work.
People follow people.
A faceless brand sending AI generated content doesn't build trust.
A real person sharing what they're actually building does.
On the tools side, Tyler sees AI as an always on editor.
Not something that writes your newsletter for you, but something trained on your content that knows what's performed well and who your audience is.
It helps you create better content, not replace you.
He also thinks AI will take over the operational grunt work that most newsletter operators hate.
List cleaning, subscriber re engagement, and figuring out which boost publishers are sending quality leads.
The stuff that eats hours but nobody wants to do.
how he monetizes
Tyler monetizes Big Desk Energy in 3 ways:
Beehiiv Boost: He recommends other newsletters in the ecosystem and gets paid $1.50-$3 per lead he sends them (Less than 5% of his revenue, but it's passive).
Events and masterminds: He hosts a founder mastermind in Costa Rica. $10k per person, 7 to 8 attendees, which is $70k in revenue per event with 50 to 60% profit margins. He organizes everything himself. He's done four so far, with a fifth one coming up.
what to take from this
You don't need 120k subscribers to use these tactics.
The pre and post social promotion, the email gate, the zero cost referral reward, and the survey for sponsor data.
All of that works at 500 subs as well.
The difference between Tyler and most newsletter operators isn't budget.
It's consistency.
He's done these small things every single week for two years.
Of course, he was going to be successful!
📊 founder newsletter breakdown
how Sam Parr built The Hustle to 1.5m subs and sold it to HubSpot for $27m
Sam Parr launched The Hustle in 2016 as a daily business and tech newsletter.
Within 5 years, he grew it to over 1.5m subscribers and sold it to HubSpot for a reported $27m in 2021.
Before the newsletter, Parr ran Hustle Con, a startup conference that sold out its first event with 300 attendees.
That event became the newsletter's initial subscriber base.
He turned a room of people into an email list.
his funnel
The early growth came from the Hustle Con attendee list, which gave him a warm audience to launch to.
He also built a premium research product called Trends ($299/year), which offered deep dives into emerging markets and business opportunities.
Rather than feeding the free newsletter, Trends was the paid upsell.
Readers who trusted the daily email graduated into paying subscribers.
It attracted 10k+ paying members before the HubSpot acquisition.
Parr also did what most newsletter operators won't: he spent on paid acquisition early.
Facebook ads, co registration deals, and cross promotions with other publishers.
how he monetizes
The Hustle monetized through 3 channels:
Sponsorships: Daily newsletter ads sold to B2B brands. With 1.5m subscribers and strong open rates, a single sponsorship placement commanded premium pricing.
Trends: A paid research subscription ($299/year) offering deep dives into emerging markets, business opportunities, and industry analysis. This was the high margin product that proved the audience would pay for premium content.
Hustle Con: Annual events with ticket prices ranging from $150 to $2,500, depending on tier. The conference doubled as a brand builder and a revenue stream.
The HubSpot acquisition validated the model.
HubSpot didn't buy The Hustle for the tech.
They bought the audience.
1.5m engaged email subscribers in their target demographic was worth $27m.
how you can replicate this
Start with an event, a community, or a lead magnet that gives you your first 500 email subscribers. Parr didn't launch to 0. He launched to a room of people who already knew him. Your version might be a webinar, a free workshop, or a Skool community. Get the first subscribers from people who've already experienced your value.
Build a referral program on day one, even if it's simple. One referral gets your best resource (a PDF, a template, a video). 3 referrals get a discount on something you sell, and the rewards don’t need to cost you anything. But the behavior of sharing needs to start immediately.
Think about what your audience would pay for beyond the free newsletter. Parr built Trends because his readers wanted deeper research. Your version might be templates, a community, consulting access, or a course. The free newsletter builds trust. The paid product captures the value.
Treat your subscriber list as an asset with a dollar value. Parr grew The Hustle, knowing that every subscriber added to the valuation. Whether you plan to sell or not, an engaged email list is the most valuable thing you can build online. It compounds in ways that social followers never will.
end
📧 ready to build your own revenue generating newsletter?
🎯 No owned audience = you're renting space on someone else's platform Zero recurring revenue = starting from $0 every month
Want Your Newsletter Blueprint?
✅ Pick your $500+ monetization strategy
✅ Set up your first automated revenue stream
✅ Create content that converts browsers to buyers
🔗 Stay Connected:
Twitter (X) → https://x.com/itstreheart
Instagram → https://www.instagram.com/itstreheart/
YouTube → https://www.youtube.com/itstreheart/
P.S. Every day you wait is another day your competitors are building their owned audience while you're stuck hoping the algorithm shows your content.
Your newsletter could be earning $500+ by next month.
Catch you later,
Tre
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