Nathan May

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.

We have 50k email subscribers, but the newsletter doesn’t make money.” I hear versions of this from web-first publishers all the time. Here’s what I’d do to make it a $500k/yr revenue asset: The problem is that your newsletter isn’t actually a product. Most web-first publishers treat email like a distribution channel, traffic driver, or a dumping ground for links. This leads to low engagement, no clear ownership, sales teams ignoring it, and sponsors who don’t care. If you want your newsletter to work, you have to invert the model. 1. Obsess over revenue, not growth If you have 10k–50k subscribers, that’s enough to start. But only if: • Your inventory is clearly defined • It’s not bundled into random web deals • Someone actually owns selling it You need: • A dedicated seller for newsletter inventory • Or an agency (short-term) to prove demand If no one owns it, it doesn’t exist. 2. Fix the product (this is the real problem) If your newsletter only has: • Headlines + lots of links • Thin summaries that redirect to the website to read the content • No actual content people would miss if it disappeared tomorrow ...Sponsors won't pay for that. Readers won't forward that. And no amount of sales effort fixes a product that isn't good. You need to make a real editorial decision: build a newsletter-first product, not a web-first product. That means hiring a writer and developing a content strategy to share: • A strong point of view • Real insights inside the email • Curated + explained news (not just linked) Think Morning Brew, The Rundown, The Neuron. Content that lives and dies in the email itself. 3. Only then should you think about growth Most publishers already have a list. Use it. Start selling sponsorships to that audience. Prove engagement + revenue If demand > supply, then scale with Meta ads. Most web-first publishers don’t have a growth problem. They have a product + ownership problem. Fix those two things, and the newsletter becomes scalable and valuable. Right now, for most publishers, it’s none of the three.

@oliverbrocato Beautiful - apartment is coming along well homie

work from home friday 📍NYC

My buddy gets 30M+ views on socials per month. He shared how he’d get his first million views if he started from zero today: 1. Volume > perfection (early on) Post 21 times in 7 days. You don’t need to spend weeks trying to get your first post perfect. You need data to see what’s working. Just ship it. 2. Remix what already works • Go to your platform (TikTok, LinkedIn, IG) • Search your niche • Filter top content in the last 90 days Now you have proven topics, hooks, and formats. The algorithm already told you what people want. Now give it to them in your voice. 3. Build a series The accounts growing the fastest right now are building series people feel compelled to follow. Think about the accounts doing: • “Day one of digging into my wall until I hit X followers" • "Day one of dropping this blob until it reaches the Burj Khalifa" Sounds ridiculous. But people come back every single day because there's a storyline. There's something to follow. That's how people get 200K followers in a month. The principle works in any niche. Create a series where something is at stake, and people have a reason to come back tomorrow. 4. Jump on trends immediately My buddy got 10M+ views on a single video series by jumping on the Astronomer CEO scandal early. He made the series specific to his audience, explaining: • How the CEO was allegedly having an affair with the Chief People Officer • Why does that become a huge corporate issue • How scandals like this usually lead to executive turnover + new hiring So instead of generic gossip, he turned it into career advice for his audience. Rule: If it’s trending, post ASAP. Don’t worry about how it looks. 5. “Borrow” hooks from viral content This one is underrated. Find a viral video in your space, take the first five seconds of it, and react to it or add your own take. The logic is simple: you already know the hook works. The platform already proved it. Why spend time writing hooks from scratch when you can attach yourself to something that already has momentum?

@itsalexvacca Ads

We built 12 Claude Code skills that run our entire paid media ops across Google, Meta, and LinkedIn at ColdIQ (and we're giving the whole pack away). Our head of growth Ivan Falco runs $200K/month in ad spend from a terminal. It's how we doubled client load this year without losing quality. The skills do the work that used to fill our media buyers' calendars: spot creative fatigue, adjust bids, upload audiences, run bulk edits, flag broken campaigns, build reports. Each skill does a specific job: Google Ads: → keyword-analyzer: audits quality scores and finds keyword gaps → negative-keywords: reviews search terms and blocks wasted spend → performance-auditor: compares periods and flags what changed → search-terms: surfaces queries burning budget with zero conversions Meta Ads: → audience-builder: turns CRM lists into custom audiences → creative-fatigue-analyzer: spots declining CTR before the metrics flag it → fatigue-monitor: flags when your audience is saturated → spend-tracker: tracks budget pacing across every campaign LinkedIn Ads: → audience-builder: builds targeting audiences at scale → bid-optimizer: adjusts bids across campaigns in bulk → bulk-editor: mass edits campaigns, ads, and naming in seconds → creative-builder: generates ad creatives from brand specs You drop them into Claude Code, connect your ad accounts, and tell it what you need. It reads the skill, plugs into the platform, executes. 300+ hours of work went into building these. Comment ADS and we'll send all 12 over.

There's one rule for scaling Meta ad spend that you shouldn’t break. A company ignored it, and it cost $250K in wasted ad spend in a single month. The rule: Never increase Meta spend by more than 20% every four to five days. This company went from $150K/mo to $405K/mo in Meta spend almost overnight. What happened next? Within 2 weeks, • CPMs spiked •CPL 2x’ed • Margins got crushed The ads and landing page weren’t the problem. Even click-through rates were completely normal. The only thing that changed was how fast they pushed money into the market. When you ramp up too fast, you flood Meta’s auction. The algorithm doesn’t have time to adjust. So it does the only thing it can: • Finds more expensive impressions • Bids higher for the same users • Pushes your CPMs (and CPL) up instantly It's not a creative or an audience problem. It's purely a pacing problem. The fix: If you need to go from $300K to $600K in monthly spend, following the 20% rule, that takes six to eight weeks to do cleanly. Which means if you know a high-revenue period is coming (a big product launch, a seasonal spike, a major offer), start scaling six to eight weeks before it. Most people start thinking about this two weeks out. By then, it's already too late to get where you want to go without breaking the rule. And if you do break it and CPLs spike, immediately pull back down. Watch your CPM data daily. Let the account stabilize before pushing again. CPLs will likely recover, but not always to exactly where they were.

I've spent $6M on Meta ads to acquire 4M+ subscribers. Here’s the exact 3-tier framework we use to attract paying readers: Most people run Meta ads like this: Optimize for leads > lower CPL > spend more. Looks good on paper, but here’s the problem: Meta is optimizing for the cheapest users, not the most valuable ones. So as you scale: • You get more subscribers • But worse monetization • And your ROAS quietly dies We’ve been reworking this with a simple 3-tier framework: 1) Stop optimizing for “any click,” optimize for offer clicks A lead event tells Meta: find me someone who fills out a form. An offer click tells Meta: find me someone who actually engages with what we're selling. Those are very different people. When you optimize to offer clicks, you're asking Meta to find subscribers who behave more like buyers from the moment they land on your list. CPL will likely go up, but ARPU tends to go up more. 2) Run dual-event optimization You can optimize for TWO events in one campaign. The problem with optimizing purely to offer clicks is that Meta needs a minimum volume of events to learn efficiently. If you don't get enough offer clicks fast enough, the algorithm doesn't have enough data to optimize properly. The fix: Pass back both a lead event and an offer click event in the same campaign. Meta hits its data threshold on the lead event, so the algorithm keeps running. But you're also sending back a higher-quality signal that tells it what a valuable subscriber actually looks like. You get scale + quality at the same time. 3) Build a predictive LTV signal This is the real unlock: • Watch each subscriber for their first 14 days • Track every action they take: offer clicks, applications, purchases, whatever your funnel looks like • Assign a dollar value to each action • Then pass back the value of the highest-value thing that the subscriber did as a single dollar figure to Meta Instead of telling Meta "this person is a lead," you're telling Meta "this person is worth $47" or "this person is worth $12." The algorithm learns to find more people who look like your high-value subscribers, not just any subscriber.

Your 45% open rate might actually be 20% due to Apple’s Mail Privacy Protection. It fires a tracking pixel the moment an email hits the inbox, whether it’s opened or not. So, what should you track instead? There are many newsletter business models, but the principle is the same: Get as close to revenue as possible. And regardless of model, every operator should care about Click-through rate: Are readers clicking on sponsor links, offers, or anything at all? You want 3 to 5%+ CTR as a baseline. Everything else depends on how you make money. 1. Affiliate newsletters Think ROAS, not opens: How much revenue do you get per dollar spent? The best (MarketBeat, The Points Guy) get purchase data back from partners and optimize at the ad level. They live and die by revenue per user. 2. Sponsorship newsletters Ad click-through rate is your north star. You want 0.5 to 1%+ on your sponsored placements. Below that, sponsors won't renew, and frankly, they shouldn't. For B2B newsletters, especially, you also need to know what percentage of your list is actually in your ICP. A 10k list with 60% ICP > 50k list with 5%. Use Apollo or a similar enrichment tool to find out. 3. Paid subscriptions You want a 2-5% free to paid conversion. Below that, the problem is usually one of three things: wrong audience, wrong offer, or you're not putting the paywall in front of people often enough. 4. Courses/webinars Three numbers matter here: • 3%+ click-through rate on your email CTAs to register If people aren't clicking, not enough are seeing the offer. • 40%+ show rate on your webinars If people register but don't show up, your confirmation sequence needs work. • 10%+ buy or book a call at the end Below that, and something is off, either in the pitch or the audience quality coming in. 5. Service businesses Focus on two numbers: • 3%+ CTR to on emails to book calls • 20-30%+ close rate on the calls you book Low close rate is a sales problem. Low booking rate is a content and trust problem. Most operators stare at open rates and wonder why growth is flat. The real signal is simple: • Are people clicking? • And what happens after? Start there. Get as close to revenue as you can.

@maxwellcopy 🐐🐐🐐

Posting has changed my life genuinely more than anything else I can think of. 1/ It made me a better writer. I hated writing my whole life, never thought I'd enjoy it. But writing so much content and getting good at it... I actually like it now. And more importantly, it forced me to think about the person on the other side and what actually gets people to want to read your stuff. Forced to learn psychology, copy, and getting people to do what you want. Skills I will use for the rest of my life. 2/ It made me a way better communicator. When you write this much, you develop a skill for taking complex thoughts and distilling them into something anyone can understand. I'm way more intentional with what I say now because of it. 3/ Learning about a topic I've learned more about email marketing and ecommerce from writing than anything else. If you want to learn something, write a 50 page guide on it… The art of trying to teach other people forces you to do outside research, look at examples, create frameworks, and all of that information just gets etched into your brain. Almost all of my biggest breakthroughs in strategy and knowledge have come from writing content. 4/ It gave me a business. A multi seven figure, almost eight figure business... all from posting organic content. No ads. Never had to worry about CPMs or meta accounts getting shut down. The hardest part of any business is getting clients… And content just made that happen naturally for us. 5/ It gave me the greatest connections of my life. Some of my closest friends I met online from my content. People doing cool shit want to talk to other people doing cool shit... And if you post stuff that's actually insightful, those people find you. My business partner Michael reached out to me because of a post. 6/ It allowed me to work with my idols. There are 3 specific people I look up to the most in life and business. All 3 of them I’ve been able to work with from them reaching out after seeing me posting online. The fact that people I literally look up to reached out to ME because they liked what I posted is still insane to me. 7/ It made hiring so much easier. When you post good content and build an audience, people want to work for you. Would someone rather work at a faceless company with zero credibility in the space... or work with the guy whose face they see every day teaching them email? It's become way easier to hire great people because of our platform. And it helps with retention too... when people say they work at WellCopy, people go "oh shit, you work at WellCopy?" That matters. 8/ Once a month I get a +157 aura boost when I'm at a bar and somebody comes up to me like "yo, are you Max? I watch your shit all the time" +aura every time especially if you’re in a conversation with someone else at the time. TLDR; Content has given me outsized returns in many aspects. Everybody should spend 2-3 hours on content every day.

My little startup went from 0 to $4M ARR in 14 months. We are going to $12M by EOY. And we are about to make our most important hires: 2 founding engineers. Up until now, we’ve had one absolute tank of a CTO building everything solo. Now we are looking for his counterpart: - Someone who ships at lightning speed - Lives in NYC and is fired up to work in person and lock in - Thinks most people are retarded and gets frustrated by incompetence or slow movers - Neurodivergent, thinks different, acts different. Plus if you can’t hold eye contact, very bullish - I need to sit you down and explain the importance of deodorant, cologne, sunlight, and touching grass We are looking for a needle in a haystack. If that’s you or you know someone, comment and DM me. $10K to whoever helps me land my rainman.

@thesamparr Tried to pay @jackhneel for this when he still did coaching but it was just as he was entering hockey stick growth (now Elon’s tweeting him and he’s too popular!) Maybe buying time from someone’s trailer strategists is the move? Since they’re “mining” eps for top 1% moments

A podcast/interview coach. The best way to get better at sales = review the sales calls with a sales coach. Would be cool for this to exist for podcasts and interviews. Yes, very niche + easy to mock. And yes, the audience critiques a ton. But I think a coach to help you via review your shows, the host, get breakthrough convos + insights + the best content out of a guest...that would be cool. I want this!

@oliverbrocato @allanmaman Wholesome Wednesday

has to be @allanmaman for me 🚀

Your Meta CPL just spiked from $2 to $5 overnight. To correct this, before you touch anything, ask yourself: Are all your ads performing badly at the same time, or just your top two or three? Scenario 1: Every single ad is red Bad news emotionally, but good news operationally because this means you flooded the market. Meta went out looking for the same audience at the same time across all your campaigns, and it ended up paying more per impression. Key signal: • CTR stayed stable • Conversion rate didn’t break • Only CPM > CPL increased Translation: Your ads still work. You just overpaid for attention. Fix: Reduce spend > CPMs normalize > CPL comes back down Scenario 2 (the one you don’t want): Your top two or three ads, the ones that have been carrying your account for months, suddenly go red. Everything else is fine. That's creative fatigue, and it's a one-way door. Those winning ads have burned through their audience. The people most likely to respond to that creative have already seen it too many times. You can't un-fatigue a saturated ad. You can't fix it by spending money. You need new creatives that can replace those winners, and finding new winners takes time. That's the situation you don't want to be in, especially heading into a high-revenue period. So when CPLs spike, run through this checklist before doing anything: 1. Check variance across ads Pull your performance by ad and look for patterns. Is everything red, or just the top spenders? 2. Check CPMs specifically If CPMs spiked and click-through rates held steady, it's a market flooding problem, not a creative problem. 3. Check landing page conversion rate If that's also down alongside CPMs, there might be something else going on worth investigating. 4. Check timing Did the spike happen right after a big budget increase? That's almost always the culprit when performance drops uniformly.

@maxwellcopy Texted you!

NYC for all of May… hmu if you are here!

3 newsletter founders (with $300K, $500K, and $1M+ in revenue) recently asked me for advice on selling their newsletter. Here’s exactly what I told them: The first thing to get honest about is what you're selling. Most newsletters don't have ad partnerships or products generating $100K+. Which means they have a list, not a business. Lists sell for under $2 per subscriber. The Hustle, Milk Road, and The Neuron sold at real valuations because they were profitable operations that didn't depend on the founder. I call it the bus test: if you got hit by a bus tomorrow, would the business keep running? If no, you haven't built an asset. You've built yourself a high-paying job. And high-paying jobs sell at 3-4x profit, not the 5-10x founders often imagine. I watched this play out with The Neuron, a deal I almost acquired myself. Before the sale, Noah, the founder, delegated growth to my team, handed sales to an outside agency, and hired a full-time writer. All-in under $300k. That's what it costs to prove the business runs without you, and what unlocks a real exit. The Rundown, The Deep View, and Superhuman all have in-house writing teams and strong sales functions. The Rundown was at $4-5M in profit as of October 2025. That's a $20M+ exit if they ever sell. The other mistake is trying to sell to other newsletters. It sounds logical: same audience, natural fit. But the buyers think: "Why pay a business multiple per subscriber when I can buy those same people on Meta for less?" Hard to argue with. The real buyers are strategics, companies where your audience is worth more than ad inventory. HubSpot buying The Hustle is the textbook example. When your average deal is $50k+, paying a premium for a warm, relevant audience is a no-brainer. So, if you're thinking about selling in the next 12 months: 1. Get yourself out of the business. Delegate writing, sales, growth, and prove it operates without you. 2. Clean your books. Sponsors paying 2-3 months after a campaign runs is a red flag that buyers notice immediately. 3. Retain your sponsors. High repeat rates tell a story about audience quality that no pitch deck can fake. The founders who walk away with great exits didn't stumble into them. They spent 12-18 months making the business look exactly like what a smart buyer wants to own.

@mattepstein This is literally what @jakewilliammo pulls out of a zip lock bag every day at noon

Can't wait for lunch at the slop bowl trough with the boys today

I just met a 20-year-old who makes $2M/yr from LinkedIn. What he showed me broke my brain: 8 months ago, Shamus Maden was kicked out of college and moved to NYC with just $14 in his bank account. He was on track to lose everything. Then something clicked. He spent months obsessively studying the LinkedIn algorithm and discovered a secret that he’s used to generate $10M+ for startups backed by a16z, Sequoia, and Kevin Durant. I visited my buddy @_May_Ham's office in New York recently, and he introduced me to Shamus. @shamusmadan showed me under the hood of how he writes viral content. He pulled up two posts side by side. One had 24,000 views. Solid engagement. Decent post. It generated 1 sales call. The second post got 2.1 million views. Massively viral. Flooded with comments, likes, and reshares. It generated 84 qualified sales calls. I asked him what was different. He called it the EVC Framework: 1. Emotion — the hook makes you feel something before you understand anything. 2. Value — every line hints at what the reader gets if they keep going. 3. Credibility — proof is baked into the story, never bolted on at the end. Most LinkedIn content gets attention but doesn't make money. He figured out how to do both. If you're a founder looking to blow up on LinkedIn, talk to Shamus. He’s killing it.

@tomaldertweets @shamusmadan is the GOAT

@maxwellcopy @Jacobsklug

Yo I need some AI wizards to help us build some more tools internally. Who got me?

@thesamparr @austin_rief @austin_rief BDE

I was texting @austin_rief about a new business idea he's brainstorming. I asked, "think it'll be successful?" His reply: if i want it to be. Gangster energy is contagious. Surround yourself with it!

@thechrismeade 1,500 = active members or cumulative?

Next month we’ll cross 1500 members in The Founders Club. Never in my wildest dreams would I have imagined it grow this fast, so quickly. We’ll do 50,000 applications this year wtfff