AcquiredNot Boring (with Packy McCormick) - Extended Cut
CHAPTERS
- 0:00 – 3:07
Mission: Get Packy to 100K — why Not Boring is an Acquired-worthy “one-person company”
Ben and David set the stakes: this episode “fails” if Packy doesn’t cross 100K subscribers. They frame Not Boring as a rare case study—a solo creator business that has become a media brand and investing platform in just 18 months.
- •Goal-setting as a narrative hook: 88,460 subscribers at recording time
- •Not Boring as Substack’s top business newsletter and an emerging media/investing hybrid
- •Packy’s distinct voice: serious research + playful tone
- •Promise of the full “Acquired deep dive” treatment
- 3:07 – 7:09
Housekeeping: Acquired LP Show feed + sponsor setup (Pilot)
Ben and David announce a major distribution change: the LP Show back catalog is now available publicly via a new podcast feed. David then introduces Pilot and explains how their software-plus-humans accounting model works for startups (including solo corporations).
- •New public feed: “Acquired LP Show” with back catalog access
- •LP perks remain (early access, community calls, etc.)
- •Pilot’s hybrid model: software ‘Iron Man suit’ for finance pros
- •Listener discount and positioning Pilot for modern startups
- 7:09 – 8:37
Who is Packy McCormick? The identity problem of a modern creator-founder
The conversation opens with a deceptively hard question: what does Packy even call himself—writer, founder, author? Packy explains why “founder” is the most flexible label for an evolving, multi-pronged business.
- •Creator roles are fluid; titles lag reality
- •Not Boring as a brand that spans writing, investing, and community
- •‘Founder’ as a catch-all for a constantly changing job
- •Early hint: the “Not Boring empire” isn’t just a newsletter
- 8:37 – 16:49
Origins: childhood ‘newspapers,’ humor as a weapon, and the work-ethic engine
Packy recounts early signs of his future: homemade mini-publications and a lifelong drive to make serious work entertaining. He connects his comedic style to deep diligence—and credits his parents’ intense work ethic and a defining ‘loser box’ lesson about honesty and effort.
- •Early publishing instincts: Post-it-note newspapers
- •Style blueprint: class clown + real research rigor
- •Parental work ethic as the foundational operating system
- •Formative ‘French C+’ story: honesty, accountability, and owning mistakes
- 16:49 – 29:26
Duke to Wall Street (in the recession): Enron vibes, public finance, and the MBA that never happened
Packy describes landing a finance role during the 2009 downturn, including a brutal internship environment and a rotation into municipal bonds. He then pivots into entrepreneurial experiments, applies to business school, and ultimately walks away from an MBA path when a startup opportunity appears.
- •Bank of America energy trading desk culture and constraints (no license, no fun)
- •Rotation to municipal bonds (“boring,” but Packy excelled)
- •Entrepreneurial itch persists alongside finance career
- •Rejected by Stanford; accepted to Chicago; chooses startup path instead of MBA
- 29:26 – 39:53
Breather: first U.S. hire, on-the-ground hustle, and learning ‘strategy actually matters’
Packy joins Breather as employee #1 in the U.S., doing everything from begging landlords to coordinating cleaners via Uber Rush. As Breather scales and then over-expands, he helps engineer a strategic turnaround—an experience that becomes a direct precursor to his writing on strategy and business models.
- •Breather’s original product: tiny on-demand rooms booked by the hour
- •Extreme operations: leases, furnishing, cleaning, customer experience
- •Uber Rush used creatively to solve ops/cleaning logistics
- •Overexpansion leads to negative margins; strategy memo flips margins positive
- •Strategic frameworks (Ben Thompson, Good Strategy/Bad Strategy) shape Packy’s future writing
- 39:53 – 42:01
Rite of Passage & quitting from Japan: writing as therapy becomes a serious craft
As Breather professionalizes and Packy feels underutilized, he takes David Perell’s course to reignite his brain. He quits (from Japan during a sabbatical) and begins using writing to remix ideas—starting with Ben Thompson—while searching for what’s next.
- •Rite of Passage as the catalyst for consistent writing
- •First course piece: introduction/remix of Ben Thompson’s ideas
- •Sabbatical becomes clarity: ‘the company didn’t fall apart without me’
- •Writing becomes a tool to think in public and rebuild momentum
- 42:01 – 52:39
Not Boring Club (the original plan): community-first, then COVID hits
Packy’s initial startup thesis is an in-person social club blending Soho House with extracurriculars like debate. He grows a Slack-based early community and hosts dinners—until COVID abruptly shuts down the model, forcing a strategic reset.
- •Per My Last Email newsletter as early distribution and idea lab
- •NYC Debate Club as proof-of-concept for community programming
- •Early cohort: ~150 people; dinners begin in Feb 2020
- •March 2020: ‘two weeks to flatten the curve’ kills in-person plans
- •A key failure that redirects Packy toward a media-first business
- 52:39 – 1:01:12
Not Boring becomes the newsletter: three-month bet, Product Hunt growth, and refusing subscriptions
Living in his in-laws’ basement with a baby on the way, Packy goes all-in on writing. A landing page/Product Hunt launch accelerates growth, and he chooses ad-based monetization over paid subscriptions to preserve compounding distribution.
- •Mom suggests porting the ‘Not Boring’ name from the club to the newsletter
- •Early content experiment: business strategy through pop-culture lenses
- •Addiction to growth metrics (‘welcome new subscribers… now there are Y of us’)
- •Subscription model rejected: conversion math + audience breadth + friction
- •Early scale marker: 2,000 subscribers felt like ‘this could be full-time’
- 1:01:12 – 1:09:39
Monetization breakthrough: ad deck, early sponsors, and the ‘buy an iPad’ milestone
A sponsor inquiry forces Packy to professionalize his audience story: he surveys readers, builds a sponsorship deck, and books a calendar of advertisers. Revenue grows from ‘proof of life’ to meaningful income, marked by small but memorable wins like finally being “allowed” to buy an iPad.
- •Market or Hire outreach triggers the first real sponsorship system
- •Audience survey produces a high-value advertiser profile (decision-makers)
- •Tweeting the deck fills sponsorship slots through year-end
- •Revenue psychology: growth-first, monetize later; then rapid blow-through to abundance
- •Personal milestone: iPad purchase as symbolic validation
- 1:09:39 – 1:39:28
The ‘Thursday sponsored deep dive’ model: reinventing sponsored content and redefining integrity
Packy explains how he turned sponsored posts into a premium product: only write about companies he believes in, disclose sponsorship prominently, and maintain analytical rigor. The hosts debate how this fits into modern ‘journalistic integrity’ and why transparency plus usefulness beats faux neutrality.
- •Origin: MainStreet proposes paying for a real Packy-style company deep dive
- •Rules: explicit disclosure, high bar, honest trade-offs, no time-wasting
- •Founder value: behind-the-scenes access yields unique private-company analysis
- •Critique of tech snark and misapplied investigative framing to startups
- •Integrity reframed: incentives disclosed + audience treated as smart
- 1:39:28 – 1:53:55
Web3 shift: from apologizing for crypto to writing the playbook (and surviving the backlash)
Packy describes his gradual move into Web3: starting with value-chain fundamentals, then increasing frequency as crypto keeps intersecting with broader themes. He emphasizes a middle-path stance—neither dismissal nor evangelism—and discusses audience reactions and the importance of staying grounded in business fundamentals.
- •Early web3 piece (‘Open Metaverse value chain’) was apologetic; reception was strong
- •Rule evolution: from ‘one crypto post a month’ to crypto embedded everywhere
- •Approach: translate new primitives into familiar business concepts (platforms, developers, users)
- •Backlash exists but the bigger risk is losing ‘fundamentals tether’
- •DAO case study: ConstitutionDAO shows both coordination magic and governance friction
- 1:53:55 – 2:14:23
Not Boring Capital: from syndicates to funds, transparency as strategy, and AngelList as ‘AWS for VC’
Packy outlines how investing emerged organically from writing and community—and why the fund structure beats syndicate friction. They discuss his high-volume portfolio approach, what he does and doesn’t do (no term sheets/boards), and why AngelList’s platform + human support makes a one-person venture operation viable.
- •Fund genesis: syndicate pain + founders wanting faster certainty
- •Portfolio construction: 91 investments; focus on ‘what can go right’ vs heavy defense
- •Radical transparency to LPs/public (with practical limits)
- •AngelList enables solo VC operations; ‘Jen at AngelList’ as critical force multiplier
- •Trade-offs: less traditional diligence; relies on trusted lead investors
- 2:14:23 – 2:38:40
Scale limits and future optionality: solo-corp trade-offs, potential S-curve, and a16z advisory role
The group interrogates what caps a one-person company: dependency on Packy, difficulty taking time off, and challenges scaling beyond the creator. Packy then explains his a16z advisory partnership—focused on explaining Web3, helping portfolio companies tell stories, and supporting the ecosystem—while keeping Not Boring independent.
- •Solo-corp fragility: if Packy stops, momentum slows; hard to ‘take a week off’
- •Scaling tension: hiring risks diluting the voice; audience expectations constrain monetization sprawl
- •Growth mechanics: weekly subscriber adds feel more linear as base grows
- •One-month surge: Discord/Web3 controversy, Economist piece with Chris Dixon, CNBC appearances
- •a16z advisory: translation, education, storytelling support—without becoming an in-house writer
- 2:38:40 – 3:05:50
Seven Powers, ‘should Packy join a mega-firm?’, and closing carve-outs
They attempt to map Not Boring to Seven Powers, landing mostly on Process Power (the non-replicable creative engine). The episode ends with a thought experiment about Packy joining a major venture firm, plus sponsor reads and personal carve-outs—from baby-swaddle tactics to Web3 reading and sci-fi recommendations.
- •Seven Powers debate: counter-positioning vs traditional media/VC; weak network effects; strong process power
- •Core defensibility: Packy’s creative process can’t be fully codified or delegated
- •Decision framework: control and independence vs big-firm economics and constraints
- •Carve-outs: Velcro swaddles, PSL’s Web3 engineering write-up, sci-fi novel ‘Rabbits’ (and The Expanse)
- •Wrap-up: where to find Not Boring and Packy online
