Nathan May

The old newsletter growth playbook is broken. We're building the new one | Prev @Wharton @BCG

[Nathan May @_May_Ham]

I've studied 100+ founders who turned personal brands into $10M+ businesses. Now I’m launching 𝗣𝗲𝗿𝘀𝗼𝗻𝗮𝗹 𝗜𝗣𝗢 (with beehiiv🐝), a podcast where the founders all over your feed share their playbooks.

Sam Parr, Justin Welsh, and all of our guests share one thing:

Obsession.

Some of them dropped out of college and moved across the country with nothing.

Others left cushy 6-figure finance jobs for ideas Wall Street said were stupid.

All of them stayed in the game, built amazing companies, and created their own luck.

1. 𝗦𝗮𝗺 𝗣𝗮𝗿𝗿 sold The Hustle for $27M and co-founded Hampton, a peer network for founders

2. 𝗝𝘂𝘀𝘁𝗶𝗻 𝗪𝗲𝗹𝘀𝗵 just crossed $10M in revenue single-handedly creating the category of solopreneurship on LinkedIn

3. 𝗝𝗲𝘀𝘀𝗲 𝗣𝘂𝗷𝗷𝗶 has launched five separate 7 and 8-figure businesses firing off viral posts from his phone

4. 𝗗𝗶𝗰𝗸𝗶𝗲 𝗕𝘂𝘀𝗵 ditched Wall Street to build a $700k/month hold-co training the next generation of digital writers

5. 𝗧𝗶𝗺 𝗛𝘂𝗲𝗹𝘀𝗸𝗮𝗺𝗽 has quietly built 1440, a newsletter doing $20M/year

6. 𝗜𝘀𝗮𝗮𝗰 𝗙𝗿𝗲𝗻𝗰𝗵 sold a viral short-term-rental portfolio for $7M in his mid-twenties after an Airbnb delisting nearly bankrupted him

7. 𝗘𝗿𝗶𝗰 𝗦𝗶𝘂 bought a biz for $1 and turned it into a 60-person SEO agency and top marketing podcast

8. 𝗗𝗮𝗻𝗶𝗲𝗹 𝗙𝗮𝘇𝗶𝗼 bootstrapped a $1M/month portfolio of community and SaaS businesses by 28 years old

And we're just getting started. The first episode drops Monday!

𝗧𝗼 𝗰𝗲𝗹𝗲𝗯𝗿𝗮𝘁𝗲 𝗜’𝗺 𝗴𝗶𝘃𝗶𝗻𝗴 𝗮𝘄𝗮𝘆 𝗮 𝗛𝗨𝗚𝗘 𝗻𝗼𝘁𝗶𝗼𝗻 𝗱𝗼𝗰 𝗼𝗳 𝗼𝘂𝗿 𝗴𝘂𝗲𝘀𝘁𝘀' 𝗯𝗲𝘀𝘁 𝗰𝗼𝗹𝗱 𝗲𝗺𝗮𝗶𝗹𝘀, 𝗳𝘂𝗻𝗻𝗲𝗹𝘀, 𝗮𝗻𝗱 𝘀𝗮𝗹𝗲𝘀 𝗮𝗱𝘃𝗶𝗰𝗲. 𝗬𝗼𝘂’𝗹𝗹 𝗴𝗲𝘁:

- Justin Welsh's sales emails behind Creator MBA's $1.6M launch

- Dickie Bush's funnel (landing pages, emails, and automations) from Premium Ghostwriting Academy ($500k+ per month)

- Jesse Pujji's sales call blueprint, responsible for 3 separate $10M+ companies

- Sam Parr's original cold emails to advertisers from The Hustle’s first year

- 1440's top 40 longest-running Facebook ads

Want access?

1. Like this post

2. Comment "personal IPO"]

I'll send you the Notion doc via DM today.

[Nathan May @_May_Ham]

@realcolegordon Setters

[Nathan May @_May_Ham]

@juliapintar @alexandr_wang YES!!

[Nathan May @_May_Ham]

My buddy Oliver Brocato scaled his biz to $500K/mo. I watched him get stuck at ~$80K, then in the $100K–$200K range. Here's what he wishes he knew to reach $500K/mo+ faster:

His business, Bustem, helps eCom businesses protect their brand.

They find stores, listings, and ads that copy you on Amazon, TikTok Shop, Instagram, and more, then take them down.

Getting to $500K/mo taught him some painful lessons:

1. Don’t give your product away for free

Oliver launched Bustem by posting on Instagram and Twitter that he was building a “crazy AI tool for e-commerce brands” and wanted beta testers doing $1M+/month.

The mystery created a ton of interest.

He ended up with 20-30 free users.

But most of them barely used the product to give useful feedback.

Then someone paid $5K/month.

That one customer gave them roughly 100x more useful feedback than all the free users combined.

If people have no skin in the game, they often won’t care enough to use the product or give honest feedback.

Within the first month of charging, Bustem hit ~$30-35K MRR. Month two: ~$80-85K MRR.

2. Don’t keep selling when fulfillment is broken

Oliver initially brute-forced Bustem to ~$80K/month through:

• Strong marketing
• His audience
• Credibility in e-commerce
• Solving a painful problem for brands

But then growth stalled.

The problem was what happened after the sale.

The team was basically Oliver, one engineer, and one VA.

Customers paying ~$3K/month weren't getting enough results. Their takedown success rate was only ~20%.

Sometimes they sent reports to the wrong inbox, were asked for more evidence, and resubmitted the same thing.

Customers churned because Bustem wasn't delivering what it promised.

Oliver completely jumped out of sales to fix the issue.

3. Don’t try to fix everything yourself

He stepped back and gave the team 30 days to reset.

They:

• Increased VAs from 1 to 4
• Pulled their engineer out of Slack
• Hired an operations leader
• Brought in someone to train the VAs
• Built proper processes and SOPs

Their takedown success rate went: 20% > 40% > 60% > 70% > 80%

Only then did Oliver return to selling, marketing, advertising, and networking.

He personally took 600-700 sales calls.

4. Don’t spend $15K solving a $5K problem

Bustem’s engineer was spending a huge amount of time building a fully automated backend.

But Oliver realized they were trying to solve a problem worth only ~$5K/month while spending ~$15K of engineering time to automate it.

There were “embers,” and there were “fires.” They were putting out the embers.

So, he focused their engineering resources on the biggest fires and left the smaller problems alone until they became worth solving.

Oliver has now built the base to scale Bustem to $1M a month.

[Andrew Yeung @andruyeung]

And of course, a big thank you to our speakers:

Sam Parr @thesamparr
Ryan Hoover @rrhoover
Sahil Lavingia @shl
Jay Yang @Jayyanginspires
Andy Dunn @dunn
Nadya Okamoto @nadyaokamoto
Zach Sims @zsims
Nat Eliason @nateliason
Rachel Liverman
Julian Weisser @julianweisser
Lara Acosta @Laraacostar
Alexis Teichmiller
Vitalii Dodonov @vitaliidodonov
Jonathan Javier @JWordsOfWisdom
Nathan May @_May_Ham
Josh Suggs @joshsuggss
Matthew Epstein @mattepstein
Luba Yudasina @LubaYudasina
Samantha Maestro
Rachel Hague
Francesca Albo
Luke Thorburg @lukethorburg
Ben Cera @Bencera
Daniella Alessandra Genovese

[Nathan May @_May_Ham]

Our Meta ads have added 10,000,000+ subscribers to our clients’ newsletters in the past 2 years. Every winning ad we’ve launched passes these 5 filters:

1. Is it clear, not clever?

A hook like "My entire feed is friends from Santorini, the Amalfi Coast, Bali" sounds interesting.

But it’s not immediately clear what the ad is about.

A clearer version would be:

"Is it possible to fly first class without being a trust fund kid?"

This one tells me who the ad is for and what it offers.

2. Does the visual match the copy?

One of the biggest mistakes I see is that the hook says one thing, but the visual shows something completely unrelated.

We had an ad for an AI newsletter about founders building $10M/year companies with <20 employees.

The creative showed a premium home office.

Why?

The visual reinforced the idea that a founder could run a large company from home.

You could use a dancing woman or a waterfall. But why would you?

Make the visual reinforce the hook.

3. Is it specific?

Weak: “I tried a lot of ways to learn AI until I found this newsletter.”

Specific: “I wasted $2,000 on AI tools I didn’t need before I found this newsletter.”

Specificity makes the claim more believable and interesting.

4. Does it call out the audience or the problem?

“Hey, you need to see this” could be for anyone.

Instead, write: “Are you struggling with bloating after every meal?”

Now I know exactly who the ad is for.

Or lead with the problem:

“3 reasons you’re waking up at 3 am and can’t fall back asleep.”

Problem-first hooks create curiosity without immediately feeling like a pitch.

5. Use social proof when you have it

Lead with who reads the newsletter: “Top engineers from Nvidia, Google, and Meta read this newsletter.”

Or how many: “The #1 newsletter for 1.5M+ AI engineers.”

Not every hook needs social proof. But when you have strong proof, use it.

The goal of the hook is to make the right person immediately think: “This is for me.”

That's what we're optimizing for when we spend millions on newsletter acquisition.

[alix @Allips]

i’m not a founder- but i’ve made sure that all of my friends are.

why?

because being surrounded by hyper-ambitious, financially driven, instrinsically motivated psychos makes u wanna be a harder working person

tell me i’m wrong

[Nathan May @_May_Ham]

@jspujji Amen

[Nathan May @_May_Ham]

Someone came to us after spending $4,000 on paid ads to book 13 calls, but only 1 person showed up. That’s an ~8% show rate. 4-step process I suggested to increase it to ~70%:

1. Build a breakout page after someone books

Don't just show them a calendar confirmation.

Give them a 90-second video explaining what to expect on the call, followed by 4-6 short videos answering common questions and objections.

Add testimonials and case studies, too.

Give them more reasons to show up.

2. Send 4-6 follow-up emails

Instead of sending emails like: "Your call is confirmed" or "Reminder: your call is tomorrow," send 4-6 emails between booking and the call:

a) Answer a common question

"Here's exactly what happens on the call."

b) Kill an objection

Address the biggest reason prospects don't buy, ideally through a client story.

c) Show proof

Share a relevant case study tied to the prospect's problem.

d) Set expectations

Explain who the offer is for, and what the process looks like.

e) Day-of

Keep this one short. Include the link and one useful thing to think about before the call.

The goal is to make them more confident that the call is worth attending.

3. Send SMS reminders

After someone books, have a salesperson send something as simple as:

"Hey [Name], saw you booked a call with us for Thursday.

Looking forward to it. Is there anything specific you'd like us to cover?"

It makes the appointment feel real and gives the salesperson context before the call.

4. Retarget booked calls with power content

This is the one most people overlook.

Record 5–20 short videos, answering common questions, handling objections, and showing case studies.

Then retarget everyone who's booked a call with those videos on Meta.

My target would be a frequency of 15-20 between booking and the call.

Yes, that's high.

I want prospects walking into the call thinking: "Oh my gosh, I've been seeing you guys everywhere."

One important caveat:

All of this assumes the people booking calls are qualified to begin with.

If they aren't, fix that problem, too.

But if you're paying to book calls and people aren't showing up, don't just blame the leads.

Build a system that gives them reasons to show up, reminds them why they booked, and keeps your offer top of mind.

[Nathan May @_May_Ham]

My buddy quit his $120,000/yr job and scaled his company to $1M in year one using cold outreach. His 5-step process YOU can use to grow your business to $100K/mo:

@jakewilliammo runs CampusLaunch, a business that has generated 200,000,000+ views for brands like Nike and BODYARMOR.

How did he master cold outreach?

1. Find the person who can actually buy

Jake knew he had to find the person whose job is to spend money on what he was selling.

So he targeted people at large companies who had been there for 2 years, especially brand managers and event professionals.

He used LinkedIn Sales Navigator to find people with those roles, then expanded his list to similar companies.

2. Keep your message short and direct

Here's one message Jake sent:

"I run a company that produces viral sorority activations.

What this looks like: Rush Talk dance videos sponsored by brands, plus influencers we contract to post around the activation.

These activations often get millions of views.

Open to a quick conversation?"

No elaborate personalization or long introductions.

He just stated what he does, what the buyer gets, and a simple question.

3. Share an irresistible offer

One of Jake's early messages to a CMO offered to run a full-day sorority activation for free.

"If it's not successful, you owe me nothing."

The CMO replied on a Friday at 9:42 p.m. and offered to continue the conversation.

4. Send a personalized Loom to anyone who replies

Whenever someone replied, Jake sent them a short, personalized Loom instead of a generic sales message.

He spent more than an hour creating each video.

The goal was to make the person feel like he had taken the time to understand their business.

5. Double-down on what’s working

Jake saved successful outreach messages in a Google Sheet, including how many times each one had worked.

Some had generated one response. Others, two or four.

He used those results to keep testing and improve his approach.

He also sent messages on weekends.

Saturday and Sunday outreach performed almost as well as weekday messages, sometimes better.

Jake spent weeks doing this himself, for nearly 10 hours a day, before delegating.

His advice was to learn the process firsthand before handing it off.

Takeaways:

1. Find the right buyer

2. Make a clear, concise offer

3. Send a personalized Loom to people who reply

4. Do the outreach yourself first. Once you know what works, delegate it

[Andrew Yeung @andruyeung]

Media mafia in the house at Outliers Summit

@_May_Ham
@joshsuggss
@lukethorburg
@Jacobsklug
@oliverbrocato
@shamusmadan
@mattepstein

[Nathan May @_May_Ham]

We're helping a newsletter spend $500K/mo on Meta ads and generate a 30% higher LTV-to-CAC in just 6-7 weeks. Copy our exact process to acquire readers who buy from you:

Most newsletters focus on getting subscribers as cheaply as possible.

But a cheap subscriber who never opens, clicks, or buys isn't necessarily a good acquisition.

Look beyond signup costs and optimize your entire funnel for readers who create value.

How do we approach this?

1. Get more specific with your ads

Start by mapping out your ideal reader profiles.

Don't just target people who might be interested in your newsletter. Figure out exactly who you want reading it.

Then build creative specifically for those people.

This often means testing different formats, angles, and copy variations.

For example, text-over-video ads with multiple copy variations often outperform polished, branded creative.

UGC can work too, but it typically costs more.

Our job is to find the creative that gets you the lowest cost per opener and cost per ad clicker.

And we'll use the data to compare formats rather than assume one is better.

2. Optimize for higher-LTV subscribers

Getting someone to sign up isn't the end of the funnel.

You want Meta to find people who will open, click, engage, and generate more revenue over time.

That's where event optimization comes in.

Set up your funnel architecture to pass back deeper-funnel events to Meta.

Instead of optimizing purely for signups, you can give Meta signals that help it find subscribers with higher lifetime value.

3. Build the dashboards to understand what's working

This is an area where even sophisticated newsletter teams have gaps.

We recently signed one of the top AI newsletters.

They have engineers and AI experts on the team, but hadn't built out dashboards to measure things like:

• Cost per clicker
• Cost per ad clicker
• Subscriber LTV

Without that data, it's difficult to know which campaigns are driving valuable subscribers.

You need to measure beyond the initial acquisition cost and use those insights to make better optimization decisions.

[Nathan May @_May_Ham]

@AlexFinn Appreciate you dude - come hang in NYC soon

[Nathan May @_May_Ham]

I’m excited to announce that I acquired my first company to make your team 5x more efficient:

Introducing: Creme Digital.

I met their team after they started building AI workflows for my friends’ companies.

And immediately knew I needed them to build for my main biz, The Feed.

They did such a good job that I thought, “Would it be so crazy if I just owned this thing?”

So I acquired them to solve a huge problem most companies are having.

See, there’s a gigantic difference between sleepy sales and ops teams…

…and the ones using AI to replace six-figure software contracts and 10x their prospecting and sales.

Creme’s built to bridge that gap.

Most companies are still wasting $200k/month or more in team time doing things like…

1. Manually updating CRMs
2. Researching every prospect for 30 mins before a sales call
3. Manually creating follow-up emails, case study decks, and proposals

So here’s what we do:

1. Train your team so your top performers can build AI workflows that create millions of dollars of value for your brand.

2. Install our AI-native engineers into your company to build agents and advanced tools that add revenue without adding headcount.

We've worked with 200+ brands from award winning agencies like Street Talk to juggernauts like Paramount.

Want us to take your team from AI-curious to building your first fully usable agents for sales or operations in less than 72 hours?

Book time, link in the comments.

[Nathan May @_May_Ham]

@andrehaykaljr Ty ser!!

[Nathan May @_May_Ham]

@AndrewWarner Hell yeah!!!

[Nathan May @_May_Ham]

@themaxyang LFG!!

[Nathan May @_May_Ham]

@austin_rief Ty dude :)

[Nathan May @_May_Ham]

@Jack_Raines @safwaankay Appreciate you my guy!!

[Nathan May @_May_Ham]

@lukethorburg Appreciate you homie

[Nathan May @_May_Ham]

@joshsuggss Love ya brotha