AcquiredNot Boring (with Packy McCormick) - Extended Cut
CHAPTERS
Subscriber milestone banter + what this episode is about
The hosts open by joking about getting Packy past 100K subscribers, then frame the episode: an Acquired-style deep dive on a “one-person company,” Not Boring. They tee up why Packy’s growth is notable and how he’s blending media and investing into one empire.
Show announcements, sponsors, and disclosures (LP feed + Pilot)
Ben and David announce a new public feed for the Acquired LP Show back catalog while preserving paid perks for LP members. They also introduce presenting sponsor Pilot and explain how Pilot blends software and human accountants; then they disclose their investments in Not Boring entities and clarify this isn’t investment advice.
The “Founder” identity problem: what does Packy do?
David probes Packy’s LinkedIn title and the challenge of describing a hybrid career: writer, founder, investor, media operator. Packy explains why “founder” is the catch-all when the role keeps evolving.
Early signals: class clown + serious research + work ethic origin
Packy recounts childhood “newspapers” and humorous writing, then connects it to his current voice: playful but rigorously researched. He attributes his work ethic to his parents’ intensity and shares a formative “loser box” story about honesty and accountability.
Duke years and landing a 2009 Wall Street job in a recession
Packy describes Duke activities (debate, a cappella) and then how he entered finance during a tough hiring market. He clarifies his role was public finance/trading-adjacent, starting with a 2008 BoA internship amid ex-Enron culture and then rotating into muni bonds post-merger.
The MBA that never happened: Throgo, rejection, and a leap to startups
Packy explains applying to business school with a party-bus startup (Throgo), getting rejected by Stanford, accepted at Chicago, then deciding not to attend after a deferral was denied. He chose instead to pursue a startup opportunity (Breather) and spent an in-between period trading—making classic early mistakes (Tesla/Facebook/Bitcoin).
Breather: the gritty GM job—leases, cleaning, and building a city from scratch
At Breather (6-person Montreal team), Packy became the first U.S. hire and NYC GM, navigating landlords, furnishing, operations, and customer experience. He describes extreme operational realities—personally cleaning spaces and coordinating Uber Rush couriers—before scaling to leadership roles.
Strategy matters: overexpansion, negative margins, and a turnaround memo
Breather expanded too fast (one space per day) and ended up oversupplied with negative gross margins. Packy and a data science colleague wrote a strategy memo to add monthly rentals and dynamically flip inventory; the company bought in and margins swung from -25% to +25%.
Learning to write: David Perell’s Rite of Passage and Ben Thompson as godfather
Feeling stuck, Packy took Perell’s writing course and started publishing. He wrote early pieces remixing Ben Thompson’s thinking, framing Thompson as a key inspiration; this launched the habit and identity of publishing regularly.
Quitting from Japan and the false start: Per My Last Email + Not Boring Club
Packy took a sabbatical, realized he needed to leave Breather, and quit while in Japan. He continued a link-roundup newsletter (Per My Last Email) and tried to build Not Boring Club—an in-person social club combining Soho House vibes and extracurriculars (debate club, dinners)—right before COVID shut it down.
COVID pivot: porting “Not Boring” to the newsletter and committing to the craft
With his wife pregnant and the club paused, Packy went all-in on writing; his mom suggested moving the “Not Boring” name onto the newsletter. He experimented with pop-culture-meets-strategy essays, focused on growth, and used tactics like Product Hunt to jump from ~1K to ~2K subscribers—enough to feel real momentum.
Monetization begins: ads, the sponsor deck, and “covering the lifestyle” fast
Packy resisted subscriptions and even ads to preserve growth, but sponsors began reaching out (Market or Hire). He built an audience survey and sponsor deck, filled slots through 2020, and began seeing revenue milestones (including the “earn enough to buy an iPad” moment).
Inventing sponsored deep dives: transparency, access, and a new content format
Packy explains his contrarian model: a clearly labeled sponsored post that still aims to be the best analysis ever written on the company. He argues the sponsor relationship unlocks behind-the-scenes access that improves quality, and he maintains credibility through strict selection and explicit disclosures.
Optimism vs. journalism: incentives, credibility, and where investigative reporting fits
They debate “journalistic integrity,” cynicism in tech coverage, and Packy’s explicit optimism as a differentiator. Packy argues transparency about incentives is more honest than hidden biases, while acknowledging investigative journalism’s importance for true fraud/corruption cases.
Not Boring Capital: from syndicate pain to fund economics and portfolio construction
Packy describes how writing led to investing: helping friends explain businesses, then running syndicates, then raising a fund to reduce friction. He emphasizes a deliberate strategy: many small investments, minimal term-sheet/board work, reliance on trusted leads for heavy diligence, and transparency to LPs and the public.
Platforms make the solo corporation possible: Substack + Twitter + AngelList as “AWS for venture”
They zoom out to how modern infrastructure enables one-person companies at scale. Packy highlights that Substack is effectively free for him (no paid subs) and that AngelList’s platform—and dedicated support—lets him run a fund without building a full back office.
Web3 leap: translating crypto with business fundamentals and staying tethered to reality
Packy describes gradually shifting into crypto/web3, beginning with value-chain thinking and moving to Ethereum/Solana and DAOs. His goal is a middle path between “it’s a scam” and “it saves the world,” grounding web3 in platform strategy, competitive advantage, and human coordination realities.
Breakout month + a16z advisory: mainstream moments and new collaboration
They recap a rapid series of wins: Discord web3 controversy (with Mario), Economist co-authored piece with Chris Dixon, and CNBC appearances, alongside major follower growth. Packy explains his a16z advisory role: helping translate complex web3 ideas, support portfolio storytelling, and contribute to broader ecosystem understanding.
Seven Powers + the future of Not Boring: process power, control, and the limits of being the product
They assess Not Boring through the Seven Powers lens and converge on process power: Packy’s hard-to-replicate creative/research synthesis and voice. They explore trade-offs of remaining a one-person company (bus factor, difficulty taking breaks), debate whether he should join a big VC firm, and discuss whether Not Boring Capital could scale to billions without changing strategy.
Carve-outs and closing: swaddles, web3 engineering notes, and a sci-fi recommendation
They wrap with personal recommendations: David’s practical new-parent swaddle tip, Ben’s “hype-free” PSL web3 engineering essay, and Packy’s sci-fi thriller book pick (Rabbits). They close by reiterating where to find Not Boring and Packy online.
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