How Packy McCormick built Not Boring into a solo media and venture empire

Executive overview

Most media companies separate journalism from advertising and keep investing at arm's length. Not Boring collapsed all three into one person and made the conflict the product. In 18 months, Packy McCormick grew Not Boring from zero to 88,000+ newsletter subscribers, crossed $1M in revenue, and launched a $10M venture fund — all without employees.

The key insight: optimise ruthlessly for audience growth first, then layer in business models that scale with reach rather than cap it. Every platform cost him nothing. The business model his readers expected him to use (subscriptions) would have killed growth. The one he invented (paid deep dives) became his moat.

The audience, the content, and the investing are so tightly aligned that each one makes the others more valuable — and no one else can replicate the creative process that holds it together.

Early career: banking, bus parties, and Breather

• Born 1987 in Bryn Mawr, Pennsylvania; made post-it note "newspapers" as a child and wrote funny essays to be allowed to read them aloud in class
• Graduated Duke 2009 with a place on Bank of America's energy trading desk (ex-Enron staff, hostile environment); rotated into public finance — municipal bonds for the state of New Jersey
• Knew early he wasn't a finance lifer; ranked top of his class to stay competitive for business school applications
• Founded Throgo, a weekend party-bus company shuttling New Yorkers to the Jersey Shore and Hamptons — not a real startup, but forced him to handle operations, deal with contractors, and navigate messy real-world problems
• Applied to Stanford GSB (rejected), deposited at Chicago Booth, then found Breather on AngelList and withdrew — forfeiting the deposit — to pursue a job there instead

Breather: operational education at a hypergrowth startup

• Joined Breather as first US employee when the company had six people in Montreal; his job was to sign leases and build the NYC market from scratch
• Persuaded landlords to rent tiny spaces to an unknown Canadian company for 30-minute intervals; literally got on his knees to beg for one key space
• When the cleaning company was acquired by Google and immediately dropped Breather, he became the world's largest consumer of Uber Rush messengers — texting individual bike couriers cleaning instructions for each space, 6am to 11pm, seven days a week
• Grew NYC team to 25 people, generating roughly half the company's revenue across 10 markets
• Promoted to VP of Experience — a catchall title for real estate, operations, design, and customer care globally across a 150-person team
• Over-expansion crisis: the board told Breather to behave like Uber and maximise supply; they signed one new space per day for a year, reaching negative 25% gross margins
• Over Christmas break, Packy and data scientist Ben Roller wrote a detailed strategy memo on how to fix the business by adding monthly rentals and dynamic pricing between long-term and hourly use — the company turned around to positive 25% gross margins
• That experience — that strategy actually matters — was the direct seed of Not Boring

Building Not Boring: growth over revenue

• Left Breather after multiple failed attempts to quit; finally called the general counsel from a sabbatical in Japan
• Tried to launch Not Boring Club, an IRL social club combining Soho House with college extracurriculars — got 150 members, ran debate nights and book clubs, booked the first dinners for late February 2020
• COVID shut down the dinners on March 10th; pivoted the "Not Boring" brand to the newsletter on his mother's suggestion
• Took the newsletter concept to the beach with his brother for a week; decided to write about business strategy mixed with pop culture — explained why creative destruction from COVID was actually freeing people from bad jobs using the Mickey Mouse Club as a lens
• Key early growth move: built a landing page and launched on Product Hunt, jumping from ~1,000 to 2,000 subscribers overnight
• Consistently told readers the subscriber count in welcome emails — "there are now Y of us here" — tracking the journey publicly from the beginning
• Rejected the subscription model even as Pooja asked about health insurance and revenue; conversion rates of 2–3% with a small list would produce a ceiling too low to justify limiting growth
• Ran all writing from his in-laws' basement in New Jersey; made his first $10,000 from sponsorships and bought himself an iPad

The sponsored deep-dive model

• Nick Abbasid at MainStreet (now part of Stripe) suggested that startups would pay for in-depth newsletter coverage; Packy wrote the first sponsored post with full upfront disclosure and the same editorial standard as his Monday pieces
• Personal bar: only write about companies he would personally invest in; disclose every time; never take a sponsored post just for the money if the company isn't genuinely compelling
• Best example: the Ramp sponsored post, where CEO Eric Glyman gave full open-kimono access — timeline of how the round came together, cap table construction philosophy — producing the most detailed piece ever written on the company
• Sponsored Thursday posts get slightly lower open rates (~37% vs ~45% on Mondays) — a trade-off he accepts because the companies are happy and the content still provides real value to founders in adjacent stages
• Substack never reached out to charge him because they philosophically oppose advertising — his primary distribution platform has cost him nothing
• Twitter Blue: pays $2.99/month as a thank-you; otherwise platforms are free
• In December 2021, Mercury account showed ~$750K in revenue with outstanding invoices; crossed $1M including those invoices, hitting the goal he tweeted in February

Not Boring Capital

• Origin: wrote an essay to explain how a friend's company worked; friend raised a syndicate with someone else; Packy launched his own syndicate on AngelList to avoid writing individual memos for every investment
• Evolved into a formal fund because founders didn't want to wait three weeks to learn how much Packy could invest
• Fund 1: $9.99M (sized below $10M for regulatory reasons); Fund 2: $25–30M
• 91 investments in Fund 1; never led a round, never wrote a term sheet, never took a board seat — by design
• Portfolio construction logic: the most you can lose is 1x; the most you can make is 1000x; optimise for catching winners, trust lead investors to do deep diligence on downside risk
• Never goes looking for flaws — openly disclosed to LPs in the same memo he published publicly
• AngelList contact Jen makes the whole operation possible: legal guidance on fund structure, LP reporting, regulatory questions — "AWS for a venture firm with someone who helps you set it up"
• The newsletter is sourcing: founders who have read Not Boring warm-introduce themselves; the binary is whether a founder has read it, not the size of the audience
• Resists transactional framing: bristles when founders ask for open rate data before committing to a deal — wants alignment with the mission, not a reach-for-money exchange

Web3 and the A16z advisory

• Wrote the first crypto/metaverse piece — "The Value Chain of the Open Metaverse" — apologetically in January 2021, worrying his fin-twit audience would revolt
• Approach: tie Web3 back to business fundamentals — what happens when you remove middlemen, where does value accrue, how do you value a blockchain as a platform
• The Solana piece ran three weeks before Solana 3.5x'd — the "alpha" his audience said they missed from the old Packy
• Joined the ConstitutionDAO attempt to buy a copy of the US Constitution; raised ~$50M in seven days — showed both the power (fast coordination around a shared mission) and limits (20,000-person Discord cannot make decisions quickly) of DAOs
• A16z advisory: working with Chris Dixon to help translate what's happening in crypto for mainstream audiences; no obligation to write about portfolio companies; wrote a piece with Dixon published in The Economist in a noticeably different voice
• Grew from 78,000 to 106,500 Twitter followers in a single month (mid-October to mid-November 2021), driven partly by the Discord/Web3 debate blowing up in his replies

The solo corporation thesis and its trade-offs

• The Not Boring flywheel: content attracts a specific audience (founders, operators, optimists about tech); that audience is valuable to sponsors and to companies Packy wants to invest in; investing gives him better content; better content grows the audience
• Every component of the business runs on platforms that didn't exist a decade ago; without Substack, Twitter, and AngelList, none of it works for one person
• Core constraint: Packy is the product — if he stops writing, the flywheel stops; no teammate can write in his voice
• Can't take a week off without worrying growth will stall; can't hire writers without diluting what makes people read it
• Could not deploy a billion-dollar fund with the current strategy — would require competing head-to-head with established firms, leading rounds, taking board seats
• Joining a venture firm full-time would immediately destroy a significant portion of his value: independent voice gone, legal and compliance filters on content, publishing cadence disrupted — the Kiva Systems / Amazon analogy applies
• The business works precisely because he hasn't gotten greedy: hasn't lowered sponsor standards, hasn't launched Paki-branded products, hasn't built an organisation that requires management bandwidth

Seven powers analysis

• Counter-positioning: sponsored deep dives and venture investing via newsletter were treated as ghettos by traditional media; Packy made them genuinely good — incumbents can't copy without undermining their own editorial identity
• Process power: the creative process that produces a great Not Boring essay cannot be written down or handed off; even Packy cannot articulate a repeatable system for how lightning strikes; this is why the business is hard to scale but also hard to replicate
• Weak network effects: value increases as more people in a founder's or reader's circle also subscribe — warm introductions, shared cultural references — but it is well below platform-strength network effects; Packy acknowledges it is weak and identifies building an actual community (Discord, DAO, token) as the obvious opportunity he hasn't pursued
• No scale economies; no cornered resource in the traditional sense; the closest thing is Packy himself, which Hamilton Helmer would call a personal cornered resource rather than a process