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.

I got into Wharton by accident. I was trying to apply somewhere else entirely. In high school, a classmate brought in a magazine article saying actuaries made $150,000 to $200,000 a year. I decided on the spot that that's what I wanted to be. So I only looked at colleges with an actuarial science program. Penn has four undergraduate schools on one campus: • Nursing • Engineering • The College of Arts and Sciences • Wharton The actuarial science program I wanted was in the College. But I thought it was inside Wharton. So I applied there, and somehow got in. That mistake changed my life. My econ class was held in an auditorium named after a classmate's father, who'd donated enough money to get his name on the building. Friends came from families that owned investment banks, billion-dollar companies, and businesses I’d only ever heard about. I had never been around money like that before. People talk about Ivy League schools as life-changing through the network or the brand name. That happens. But for me, what changed was getting dropped into a level of wealth and normalcy around money that I didn't know existed. That's the real value of the right environment. It quietly resets your bar for what's normal. If everyone around you is fighting for $10K, that becomes the ceiling you're aiming at without even realizing it. Put yourself where the baseline is $100K, and you stop negotiating with yourself over whether bigger is possible. You just start working toward it, and most people end up going further than that bar without ever meaning to.

@lukethorburg Rizz ‘em with the tism

An autistic 16 y/o just applied for a job on my team And honestly he’s more impressive than 90% of the candidates I’ve interviewed Can I even legally hire this kid?

@MCovBrown How much are a spouse and 2 kids 😬

@_May_Ham Some variables that will likely change: you want to spend more. You get married, have kids. Etc. But I think the conservative withdrawal rate + extra cushion cover that. Did this exercise a few years ago and it was insightful

I used ChatGPT to calculate the exact net worth I'd need to never worry about money again. It took about 30 minutes: Step 1: Audit your real spend, then stretch it I currently spend around $9,000 a month living in New York. Instead of guessing at some arbitrary number, I asked myself: "What would my ideal life cost if money stopped being a constraint?" That meant prompting ChatGPT to build out my ideal lifestyle: • Rent: $7,500 • Chef (including groceries): $4,250 • Weekend meals: $1,300 • Personal trainer: $1,500 • Healthcare: $800 • and more Total: $19,682/month, or $236,184/year in pretax income needed. Step 2: Turn that into a net worth target The goal isn't to earn $236,184 from a job. It's to build enough wealth that your portfolio generates it passively every year. At a ~23.8% effective tax rate (federal + state), that generates roughly $15,000-$19,000/mo after taxes depending on your portfolio structure. ChatGPT modeled two scenarios to find what net worth generates that: 1. Scenario 1 Pure dividends only (1.5% yield): $236,184 / 0.015 = $15.75M needed This generates ~$15,000/month after taxes. 2. Scenario 2 Mix of dividends (1.5%) and selling stock (1.5%), a 3% total withdrawal rate: $236,184 / 0.03 = $7.88M needed This generates roughly $16,000-$19,000/month after taxes. The second scenario works as long as the market does what it's averaged over the last 40 years, around 8-10% annually. At that growth rate, your net worth keeps climbing even while you're spending 3% of it each year. Step 3: Pick your number The math came to $7.88M under the mixed scenario. I rounded up to $10M because it's a cleaner number, gives me cushion against bad market years, and honestly feels more comfortable as a long-term target. Most people never run this math. They pick a number that sounds big enough, or they never pick one at all and just keep going. Without a real target, you're either running past the finish line without knowing it, or stopping short of what would actually give you peace of mind.

@wifiimoolah Sooner! Got very lucky with business when I was 15/16, am decently on my way there already

@_May_Ham My number is the same as yours $10M It’ll probably take like 10 years for me to hit it What about you?

@tomstefaniuk Never!!

@_May_Ham Withdrawing 4% a year holds up against any period in the history of the stock market. Be more aggressive Nathan!

@alexheiden @CalebGregory304 Yessir! We work with a bunch of finpub offers. Will DM you

@CalebGregory304 @_May_Ham ?

Can anyone reading this effectively run ads for newsletters? I would be interested in your services if so. Reply or send a DM. Thanks!

Every month, my 8 friends and I share our exact revenue and profit and rank each other. Most founders would call this toxic. But it's one of the best things we do because of 3 reasons: 1. It gives us real-time benchmarks Every month I can see the margins and growth rates of eight businesses in the same space. That's proprietary data nobody shares publicly. It helps me level-set my own growth against something real instead of guessing. 2. It raises the bar for what's normal The top person in our group was doing close to $1M/month last time we ran the numbers. They're not exceptionally smarter or more capable than anyone else in the group. They just have a great offer and are an execution machine. A lot of getting unblocked in business is mental. You have to believe the next level is possible before you'll go after it. Seeing someone you know personally hit that number makes it real in a way a stranger's success never does. It pushed me to take swings I otherwise wouldn't have: • A joint accelerator partnership • A bootcamp with a founder doing $10M/yr with email • Hiring directors that felt expensive but freed me to focus on growth 3. Accountability Nobody wants to be at the bottom of a leaderboard. But that social pressure is a tool, not a side effect. There's a difference between negative social pressure and pressure you voluntarily choose because it pushes you to work harder. Same reason as committing to send a friend a gym photo every day, or lose $500 if you miss You're using accountability on purpose. But the only reason this works is trust. We've all known each other since before any of our companies were doing $1M/year. We've watched each other grow, shared horror stories, tactics, massive wins, and moments where we thought everything was going to fall apart. We've grown up together inside these businesses. That's why sharing real numbers feels safe.

@lukethorburg @pageboy @joshsuggss @mattepstein @oliverbrocato @jakewilliammo @jtsarafa 💅👑

@pageboy @joshsuggss @mattepstein @oliverbrocato @jakewilliammo @_May_Ham @jtsarafa Gay and rich

All my best friends own 7-8 figure companies The NY Post calls us the “Media Mafia” Every month we have an earnings call to see what the mafia made The cohort you choose determines your success in this game

Claude Code made this entire video. The voice, footage, script is all AI. Everything was made with a content system I built in Claude Code. In this video, I'll be taking you behind the curtain. This machine will be responsible for my entire content workflow this week. Full video is in the comments below.

@Jacobsklug AI kluggy mogs

A friend of mine had a co-founder who stopped doing any real work but still owned 40-50% of the company. He couldn't fire him or force a sale. A few people in my founder group had been through nearly the same thing. They walked him through: • What to say • How to structure a buyout • What to ask for in the negotiation His co-founder is now open to being bought out at a fair price, something he didn't think was possible a few months ago. That's what happens when you're in the right room. And it's why I spend $35,000-$40,000 a year on paid founder groups like Hampton and an office I don't even need since my team is fully remote. The benefits far exceed the investment: 1. It recalibrates what you think is possible One of my friends runs an influencer marketing agency doing $30 million a year. He's a great operator and works hard, but not necessarily 10x smarter than founders running $3M businesses. Spending time around people with bigger businesses than yours makes your own ambition feel normal instead of delusional. That mindset shift alone is worth more than most tactics. 2. Hearing other people's problems puts your own in perspective Running a company means eating glass constantly. There's a fire every week, sometimes every day, and it always feels like the end of the world. Then you sit with people running companies 10-20x your size, and realize that even the ones who look like they have it together are dealing with something. That doesn't fix your problem, but it makes it easier to keep pushing through. 3. You get access to information nobody shares publicly I know people going through company sales right now. They are completely transparent about price, deal structure, and what's cash up front versus held back. One is raising money while simultaneously fielding acquisition interest. None of this gets shared publicly, only inside the group, because of one rule: what happens here stays here. That openness has fed directly into decisions in my own business. 4. Opportunities arrive that you couldn’t have manufactured Someone in my core group referred a client to us, unprompted. I got featured on the New York Post because of the friend group I work out with at a gym. I also got invited on the Moneywise podcast because of people I met through Hampton. None of that was the plan. It just happens when you're consistently around the right people. If you're building alone, nobody around you can tell you when your 'impossible' problem already has a solution sitting two feet away.

@lukethorburg @joshsuggss @mattepstein @oliverbrocato @jakewilliammo @jtsarafa 🚀

1 year ago we were co-working out of a gym together. Now our group is run-rate $40M+. Media Mafia to the moon 🚀

@oliverbrocato @jtsarafa 😬😬

@jtsarafa * Matt / Andy

Every month, me and 8 of my best friends rank each other by revenue and profit. I’m #6 out of 9. Surrounding yourself with people ahead of you keeps you humble and hungry. Is this toxic or healthy?

A large financial publisher shared with me the #1 metric they use to scale or kill a Meta ad (it’s not CPL): They measure: 30-day eco-sales ROI. In simple terms: Did this subscriber generate revenue anywhere in our ecosystem within 30 days? That includes the initial product, upsells, cross-sells, or any downstream purchases tied to that cohort. Their benchmarks for cold traffic: • 150%+ = scale aggressively • 100% = solid, keep running • 80% = showing promise, keep testing • <80% = likely dead They expect to recoup their investment (and more) within 30 days from cold Meta traffic. CPL is almost an afterthought. This is very different from how most newsletter operators think. Most teams look at Cost per lead (CPL) and make decisions based on it. But CPL tells you nothing about what happens after the opt-in. You can have: • $1 leads that never buy • $4 leads that drive all your revenue If you optimize for CPL, you’ll scale the wrong audience. Here’s how they actually think: "If we put $100 into cold traffic, how much comes back in 30 days?” Example: You spend $10,000 on Meta. Within 30 days, that cohort generates: • $12,000 = 120% ROI = keep scaling • $8,000 = 80% ROI = keep testing • $6,000 = 60% ROI = cut it When you track 30-day ROI, you know exactly how much you can afford to spend per subscriber and stop killing “expensive” leads that are actually profitable Most newsletter operators don’t have a benchmark like this. So they default to: “CPL looks good, let’s scale.” Meanwhile, they’re burning budget acquiring the wrong readers. If you’re running paid, start here: • Track revenue by acquisition source (UTMs or campaign-level) • Group users into 30-day cohorts • Calculate: Revenue ÷ Spend That’s your real performance metric.

@blvckledge guide

q3 gift for you guys 🎁 i've compiled our top google ads strategies in 2026 into a single resource 23 guides including: > the execution playbooks > the checklists we follow > the SOPs our team uses daily like + reply "guide" and i'll dm it over (must be following)

@HenryCrochemore @denk_tweets @SchonbergerJake Slidin’ this over to the ad network team ^^ 👀👀

Coffee with a 26 year old in sf last month who runs a sleep gummy brand $3.7M/year. one full-time employee. his entire customer acquisition is 11 newsletter sponsorships in the productivity/founders niche pays each newsletter $2k-$6k per send depending on subscribers his CAC is $19 LTV at 6 months is $174 he has zero meta exposure asked him why newsletters "Facebook is auctioning my customer to me at peak price. newsletters sell me access to a curated audience at 1/10th the cost and nobody else is bidding." Every brand on meta is bidding against every other brand On newsletters you're bidding against nobody

@thisisharding I LIVE FOR THIS STUFF BABY!!! 🚀 Ty for the shoutout 🙏🙏🙏

Obsession is one of the most valuable skills. You either have it or you don't. @_May_Ham was so obsessed with Minecraft, he started an agency for it at 16. Now his newsletter growth business does seven figures. Probably not a coincidence.

@mattepstein @masonwarner 😂😂😂

@masonwarner @_May_Ham I’m reformed

Word to the wise, don’t ever agree to do cardio with this mf (especially after not hitting cardio for months) You’re psychotic @mattepstein