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]

A client was burning 80% of their $280K/mo Meta ads budget on the wrong audience. Meta had no idea. Here's how we fixed it:

In this client’s case, women engaged more with the ads and achieved lower CPMs.

So Meta kept pushing spend there.

But when we checked back-end revenue, men and women were converting at nearly identical rates.

Meta was optimizing for engagement. The business needed to optimize for revenue.

Huge difference.

And this happens constantly with newsletter businesses.

You think Meta is finding your best customers.

Often, it’s just finding the people most likely to click, engage, and consume content.

Not necessarily the people most likely to generate revenue.

In this case, women were winning the engagement battle early, so Meta stopped serving men altogether.

That creates a dangerous feedback loop:

Women engage more > Meta serves them more > Meta gathers more female conversion data > Meta becomes even more confident that women are “better” > Male audiences get ignored.

Meanwhile, there’s an entire profitable audience sitting there untouched.

This is why relying only on platform metrics like CPLs, CTRs, and CPMs is dangerous.

Here's the diagnostic to catch this issue:

1. Pull your spend breakdown by gender from Meta

2. Then cross-reference it against your real back-end revenue data

Ask one question: Is the audience getting the most spend actually generating the most revenue?

If not, Meta has been spending on the wrong people, possibly for months.

Here's how we're fixing it:

1. Build male-specific creative with hooks and messaging designed for that audience

2. Push spend deliberately toward men and watch whether the conversion rates hold at scale

If they do, the client has unlocked a growth channel that had been sitting untapped in their existing account the entire time.

The audience was already there. The conversions were already happening.

They just weren't happening often enough for Meta to notice and act on them.

[Nathan May @_May_Ham]

@aaliya_va Thank you for sharing my event with folks - this is extremely thoughtful!! Excited to see you there

[Nathan May @_May_Ham]

Your newsletter might be making $1.50 per subscriber when it could make $20. The difference comes down to one funnel mistake.

Most operators are stuck at $1.50 without realizing it.

A $50 product converting at 3-5% generates roughly $1.50 to $2 per subscriber.

You spent weeks building it, you're burning email slots promoting it, and that's your ceiling.

The $20 version looks completely different.

A $2,000 coaching offer (or a similar service) converting at just 1% gets you there from the same list, the same emails, and the same audience.

The difference is what you're selling and how you're sequencing it.

And the sequence should match the amount of trust you've earned.

Cold prospects buy based on curiosity. High-ticket buyers purchase based on trust.

That's why, for cold traffic, sell products under $50 on the front end.

At that price point, impulse buying kicks in, and copywriting alone can close the sale.

Someone sees your ad, doesn't know you yet, but $49 feels low enough to take a chance on.

Above that ($99, $199, $299), the purchase requires trust.

And trust takes time, which means the right sequence becomes: free newsletter > nurture > conversion.

This is where most operators accidentally kill their upside.

They spend weeks warming readers up, then use that hard-won email inventory to push a $29 product.

Every slot spent on a low-ticket offer is a slot that didn't move someone closer to the $2,000 offer on the backend.

If you have high-ticket offers, your newsletter should be doing four things:

• Building trust
• Increasing perceived expertise
• Segmenting intent
• Moving readers toward high-LTV offers

A $29 ebook doesn't help with any of them.

That said, low-ticket monetization isn't worthless; it just shouldn't live in your email sequence.

Plug in Sparkloop and let it run passively in the background.

That revenue comes in automatically while your emails stay focused on what actually moves the needle.

[Nathan May @_May_Ham]

@slashapp @heyStreetTalk @joshsuggss Hell ya!!!

[Nathan May @_May_Ham]

@SeanODowd15 Appreciate you man ❤️❤️

[Nathan May @_May_Ham]

@danielcberk @thesamparr Been looking for a tall handsome podcast host who knows a thing or two about newsletters if you got a guy

[Nathan May @_May_Ham]

@shamusmadan @thesamparr ❤️ YOU

[Nathan May @_May_Ham]

@jakewilliammo @thesamparr Ty ser

[Nathan May @_May_Ham]

@mattepstein @thesamparr 🫡🫡🫡

[Nathan May @_May_Ham]

@tomaldertweets @thesamparr Glad we’re homies, you’re the 🐐🐐

[Nathan May @_May_Ham]

You have 80 subscribers. You add a paid tier. But only 3 people convert. Is the offer broken, or do you just not have enough subscribers? Here's how to know and what to do about it:

Even strong newsletters with warm, organic audiences typically convert at 5 to 10% from free to paid.

At 80 subscribers, a 5% conversion rate is 4 people.

A 2% conversion rate is less than 2.

Zero conversions and a broken offer look identical at that size.

You can't learn anything useful from the results.

Wait until 200 to 300 subscribers before launching.

At that size, a 5 to 10% conversion rate means 10 to 30 people converting; enough signal to know if something is working.

A Rolex newsletter on Substack shows how this plays out.

They have 10,000 subscribers and 1,000 paying readers, a 10% free-to-paid conversion rate (one of the strongest I've seen).

They built that list by pulling followers from a 50 to 60K Instagram account.

And even at 10%, they needed 10,000 free subscribers to get there. That's the reality of paid newsletters.

You either need a large audience, higher pricing, or patience because only a small percentage of readers will ever pay.

When it comes to structuring paid newsletters, I generally see 2 approaches work:

1. Gate part of your existing newsletter

This is my preferred approach.

Readers open your normal email, get halfway through, and then hit the paywall.

I like this because:

• You don’t need to create a second newsletter
• Readers always know there's more content available
• The upgrade prompt lives inside your existing distribution

Ruben Hassid does this really well in his AI newsletter.

He’ll share tactical workflows and prompts, but the deeper prompts, videos, or advanced sections are locked for paid subscribers.

2. Create a separate paid-only newsletter

This works too.

Free readers still receive the email, but the full edition is locked unless they upgrade.

The downside is the workload.

Now you’re effectively creating an entirely additional newsletter every week.

Finally, how much should you price your paid offer?

Don't default to $7 to $9 a month just because that's average.

The right pricing depends entirely on your goal and your audience size.

If your goal is $10K a month from paid subscriptions, you need to back into what that requires.

At $9 a month with a 10% conversion rate, you need roughly 11,000 free subscribers to get there.

That takes time to build if you're starting from zero.

If you price at $25 or $30 a month instead, you need far fewer paid subscribers to hit the same revenue number.

[Sam Parr @thesamparr]

My buddy @_May_Ham grew up in a hoarder house in Ohio and didn't leave the state until he was 18. His family made $30k/year. Today he runs one of the fastest growing newsletter agencies.

How he got here:

- Overweight at 13, 2.1 GPA, addicted to Minecraft
- At age 14 starts selling custom Minecraft maps, by the time he graduates high school it’s a 6-figure business
- Gets accepted into Wharton
- Joins BCG after graduation
- Starts a crypto newsletter, sells it for a small exit

In Feb 2024 starts The Feed Media (newsletter agency):

- 0 to $1M revenue in 10.5 months
- $4-5M revenue this year
- Clients include Arnold Schwarzenegger, Jay Shetty, and more.

Became a millionaire at 22.

And yes, he’s a Hampton member.

[Nathan May @_May_Ham]

@mattepstein Deets

[Nathan May @_May_Ham]

A client's landing page was converting at 25%. One change took it to 40%:

For context, the landing page was collecting first name, last name, and email.

The CMO was convinced that collecting first names was important to personalize emails.

So we ran a simple test: What happens if we remove the first name?

Landing page conversion rate went from 25% to 40%.

That’s not a small improvement.

Going from 25% to 40% conversion means 60% more subscribers from the same traffic.

A good benchmark for a free newsletter landing page is roughly 40-45% conversion.

So if you’re significantly below that, the first thing I’d look at is friction.

And asking for someone’s name creates friction.

People don’t consciously think: “I refuse to give my first name.”

But subconsciously, each additional field requires more effort and hesitation, especially with cold traffic.

And honestly, the first name is usually vanity data.

What you should care about is the qualification data.

For example:

If you run a recruiting newsletter, I don’t really care if your name is John.

I care about:

• What role you have
• What size company you work at
• What industry are you in
• Whether you fit the ICP

That information is actually useful.

A simple framework I like:

Ask for the minimum information required to get the signup.

Then collect richer first-party data after the subscriber converts.

That can happen through onboarding surveys, welcome emails, subscriber polls, and preference centers
But subconsciously, each additional field requires more effort and hesitation, especially with cold traffic.
But your landing page has one job: Get the email.

[Nathan May @_May_Ham]

@cooldeep_me @beehiiv Big! Is this all ad network - why not do direct sold if so?

[Nathan May @_May_Ham]

My buddy Jonathan gets 30-50M views on socials per month. He shared the full system behind it:

1. His strategist finds viral formats in their niche
2. They brainstorm adaptations for their audience
3. Scripts get written and reviewed
4. Everything gets recorded in one day

That's it.

But what makes it work is what he calls archetypes: proven content formats he knows will go viral every time.

His biggest one is “hiring POVs.”

The structure is always the same:

An emotional visual in the first 3 seconds, a strong, controversial text overlay, character and story setup, and a twist ending.

One video opens with an employee crying.

The text reads: "POV: You have to lay off your employee despite a record month."

People get angry immediately.

They're ready to fight him in the comments. Then, at the end, she got promoted.

Once he confirmed the structure worked, he built a custom GPT that generates new versions automatically.

He just feeds in the details and gets a ready-to-record script based on every past version that went viral.

Guaranteed minimum 300K views. Every time.

He also runs controlled experiments to find new archetypes.

He tested two nearly identical tier list videos. One got 5 million views. The other got 100K.

The difference:

In the successful one, his guest rated something everyone does as F tier, the strongest possible stance.

In the weaker version, a different guest rated something C tier.

His framework is simple:

If people strongly agree OR strongly disagree with something, you're probably onto a winner.

So, check the comments.

If people are fighting, the algorithm keeps pushing it. If everyone's nodding along quietly, it dies.

One more tactic worth stealing:

Take the first 5 seconds of a video that already went viral and stitch it onto something new.

You already know the hook works. The platform proved it.

Why write hooks from scratch when you can borrow a proven opening and pivot the content in a new direction?

He calls it using content like Lego blocks.

Once you have a base that works, build the next thing on top of it.

[Nathan May @_May_Ham]

You don’t need 10K newsletter subscribers to sell sponsorships. You can start with <1000 subscribers if you do these 4 things:

If somebody came to me and said, "I have a 100,000-person newsletter, want to sponsor it?"

That's mildly interesting.

But if somebody came to me with a 300-person list and said, "My subscribers include 50+ SVPs at companies you actually want to reach..."

...That completely changes my perception of the value of that list.

That’s what sponsors care about. They don’t buy audience size, but access to the right people.

So, how do you actually do this with a small list?

1. Find out who's actually on your list

Self-reported data from sign-up surveys is a start, but it's not reliable.

People put whatever they feel like.

Use Clay, Apollo, or enrichment tools to figure out:

• Company
• Title
• Seniority
• Industry
• Company size

Your sponsor pitch changes dramatically once you can say:

“We have CMOs, founders, and senior operators from these companies reading every issue.”

That’s much more powerful than: “We have 2,000 subscribers.”

2. Identify your best names and lead with them

If you have 25 CMOs or SVPs from recognizable companies on your list, those names can carry an entire media kit.

A sponsor doesn't need to know your total subscriber count first.

They need to know whether the right people are reading.

3. If you don't have the right logos yet, go get them

You have control over who's on your list, especially if you're growing organically.

Reach out to 75 CMOs or senior leaders at companies your ideal sponsors want to reach.

Try to get 25 of them on the list.

Now you have something to sell.

4. Create a media kit around audience quality

Most media kits show:

• Subscriber count
• Open rate
• Click rate

That’s fine.

But for niche newsletters, the real asset is audience composition.

Your pitch should sound more like: “This is a concentrated group of senior GTM leaders and founders.”

Not: “We have 1,800 subscribers.”

That positioning matters a lot, especially early.

A lot of creators think, “I’ll monetize once I’m big.”

I actually think many people should monetize much earlier.

But only if they stop selling quantity and start selling audience quality.

[Nathan May @_May_Ham]

@ishverduzco @NotionHQ Cool! Space left?

[Nathan May @_May_Ham]

@CliftonSellers $100 CPL / $200 CPBC - what’s show rate, close rate, first purchase AOV?

[Nathan May @_May_Ham]

@oliverbrocato Don’t forget to lever up SPY 30%