The myth-busts, hot takes, explainers, and tools worth keeping.
◆Hot Take· 1
◆Hot Take1:15:30
The Journalistic Integrity Debate: Sponsored Content vs. Traditional Media
Packy and the hosts debate whether independent, transparently-sponsored writing undermines or complements traditional journalism, arguing that disclosed incentives plus a smart audience can be more honest than opaque institutional incentives.
Packy argues post-2016 skepticism of mainstream journalism opened space for alternative, transparently-incentivized media.
He contrasts hit-piece style coverage of small startups with journalism's traditional role of exposing real corruption.
Acquired's hosts note their own rule of 'assume the audience is smart' as a parallel principle.
All agree independent creators can't fully replace investigative journalism, which requires legal/editorial infrastructure.
“well what is journalistic integrity right and like i think like you know post 2016 and donald trump and everything like you know this is…”
“rule number one it acquired is assume the audience is smart”
#journalism#media ethics#independent media
✶Explainer· 2
✶Explainer2:12:00
Power to the Person: The Rise of the Solo Corporation
Packy explains the thesis behind his 'Power to the Person' essay: modern platforms let individuals snap together sophisticated back-office capabilities on demand, enabling solo operators to run businesses once requiring large teams.
Predicted trillion-dollar organizations could eventually be run by a single person, citing Bitcoin as an existing example.
Platforms like Substack, Twitter, and AngelList let one person 'snap in' capabilities (publishing, payments, fund administration) as needed.
This removes the organizational overhead traditionally required to run a media company or venture fund.
Packy credits AngelList's team (not just software) as essential infrastructure for Not Boring Capital's existence.
“there are just all of these things that you can snap off of a shelf and so instead of having to deal with all of…”
#solo corporation#creator economy#platforms
✶Explainer2:14:30
The Hidden Costs of Being a One-Person Media Empire
Packy candidly discusses the downsides of running Not Boring solo: constant pressure not to miss a week, inability to build unrelated product lines, and the risk that adding staff would dilute the voice that makes the business work.
Missing a week of writing risks slowing the newsletter's growth momentum, with no team to cover for him.
He deliberately avoids becoming an editor overseeing other writers, wanting to preserve a single consistent voice.
Building spin-off products (e.g., merchandise) would dilute the core content-focused brand promise.
Scaling into a real organization would require pausing content output, which is itself risky.
“if i don't show up and write something the momentum slows a little bit and so it's like very very very hard i think from…”
#solopreneurship#trade-offs#burnout risk
❝Story· 9
❝Story10:00
From Post-it Newspapers to 'Golden Memories': Packy's Earliest Creative Instincts
Packy recounts childhood habits — making mini post-it newspapers modeled on the Miami Herald, an embarrassing early 'book,' and a class-clown streak paired with genuine work ethic — as early glimmers of the Not Boring voice.
Made mini post-it note newspapers as a kid, inspired by his dad's consulting client, the Miami Herald.
Wrote an embarrassing early illustrated 'book' called 'Golden Memories of a Young Boy's Life.'
Deliberately got in trouble in school to be assigned essays, then tried to make them funny enough to read aloud.
Describes himself as a combination of class clown backed by serious research work ethic.
“i used to make these little books or newspapers on post-it notes”
“so i think kind of always combination of class clown with the backing of kind of serious research”
#origin story#childhood#writing voice
❝Story15:00
The 'Loser Box': A Tough Parenting Lesson in Honesty and Work Ethic
After lying to his parents about his grades, Packy's dad had him put all his trophies and certificates in a 'loser box' — a harsh but formative lesson in honesty that Packy says still shapes how openly he admits mistakes in Not Boring.
Packy told his parents he was doing well in school, then got a C+ in French.
His dad had him box up all his trophies and certificates and label it the 'loser box.'
The lesson was about honesty, not the grade itself — he had lied about his progress all semester.
Packy ties this directly to his habit of publicly admitting when his predictions or investments go wrong.
“i want all of your certificates all of your trophies anything that would suggest that you might be a winner i want them in a…”
#work ethic#parenting#honesty
❝Story18:00
Landing a Wall Street Job at the Bottom of the 2009 Recession
Packy describes interning on Bank of America's ex-Enron energy trading desk in 2008, then landing a public finance role after the Merrill Lynch merger, at a time when investment banking jobs had all but disappeared.
Interned on Bank of America's energy trading desk, staffed by ex-Enron employees who resented not taking physical delivery of oil.
As an unlicensed intern, he could sit on the desk but not trade, and wasn't allowed to join intern social events.
After the Merrill Lynch merger, was rotated into public finance (municipal bonds) rather than a fixed desk.
Was top of his class in public finance despite finding the work fairly boring.
“so i i was to be fully fair uh kind of an investment banking light in public finance”
#career#finance#recession
❝Story22:00
Getting Rejected by Business School (And Getting Into Breather Instead)
After being rejected by Stanford GSB and denied a deferral by Chicago, Packy abandoned business school entirely to chase a conversation with Breather's founder, spending the summer trading (and losing money) on Tesla, Facebook, Apple options and Bitcoin.
Rejected from Stanford GSB; got into Chicago but was denied a deferral.
Chose to skip business school entirely to pursue an open-ended conversation with Breather's founder found on AngelList.
Spent the interim summer actively (and badly) trading stocks and crypto, including selling Bitcoin at $150 after buying at $100.
Acknowledges it's hard to buy-and-hold when unemployed and cash-constrained.
“applied to stanford got summarily rejected uh from from gsb”
Breather's Grind: Landlord Pitches, Uber Rush Cleaners, and Zero Glamour
As Breather's first US employee, Packy had to convince landlords to lease tiny spaces to a quirky startup and personally coordinate cleaning via Uber Rush messengers, illustrating the unglamorous reality of early operational startup work.
Literally got on his knees to convince a landlord to lease Breather its first NYC space.
Wrote his own job description (NYC General Manager) as part of an unconventional hiring process.
When Breather's cleaning vendor abandoned them, Packy used Uber Rush messengers to clean spaces across the city.
Worked essentially non-stop (6am–11pm) coordinating logistics via text message.
“i literally like got on my knees and in one case this is actually like i mean literally got on my knees and begged to…”
“i was the largest consumer of uber rush messengers in the world for a while”
#startup operations#early employee#real estate
❝Story41:00
Quitting From Japan: How a Sabbatical Confirmed It Was Time to Leave Breather
After years at Breather, a company-granted sabbatical to Japan intended to re-recruit Packy instead confirmed he was ready to leave, and he resigned by phone from abroad.
Took a month-long sabbatical to Japan as a last effort to decide whether to stay at Breather.
Realized during the trip he didn't want to return and quit by calling the general counsel.
Notes the irony that disconnecting from a job often confirms the desire to leave rather than reconnect.
Believes the sabbatical was also useful for the team to see the company survive without him.
“i just realized that i did not want to did not want to stay there uh and so i quit from japan by calling our…”
#burnout#career transition#sabbatical
❝Story54:30
Naming 'Not Boring': A Mom's Suggestion During COVID Soul-Searching
After his in-person 'Not Boring Club' social experiment collapsed at the start of COVID, a soul-searching conversation with his mom led to porting the name over to what became the Not Boring newsletter.
Not Boring Club (an in-person social/debate club) was shut down as COVID hit in March 2020.
Packy felt embarrassed running a trivia night with only seven attendees despite his background.
His mom suggested applying the 'Not Boring' name to the newsletter instead of the defunct club.
His parents were broadly supportive despite having no clear backup plan on the table.
“well i like the name not boring club like maybe you should just like apply that to the newsletter and just go all in on…”
#Not Boring origin#pivot#COVID
❝Story1:02:30
From Zero Revenue to a Six-Figure Sponsorship Calendar
Packy describes building his first sponsorship media kit from an audience survey, tweeting it out, filling all of 2020's ad slots, and betting on 'the math' of CPMs to justify staying independent rather than getting a job.
Surveyed his audience for demographics after a sponsor asked for a media kit he didn't have.
Tweeted the resulting deck, which filled his 2020 sponsorship slots.
Relied on optimism plus a simple CPM-based math model to justify projecting future revenue.
Made roughly $10,000 in revenue by late 2020, enough to finally 'earn' an iPad from his wife.
“he's like great send me your deck and i didn't have a deck and so i surveyed the audience and i asked them for their…”
#monetization#sponsorship#early revenue
❝Story1:56:00
Building Not Boring Capital: From a Favor for a Friend to a Multi-Fund VC Firm
Packy traces Not Boring Capital's origin to an essay he wrote to help a friend explain his company, which snowballed into a syndicate and eventually a formal, AngelList-powered rolling venture fund.
Started by writing an essay to help a friend's startup explain itself, unrelated to fundraising initially.
The friend raised a syndicate off the back of it, which led Packy to run his own syndicate.
Writing new memos for every syndicate deal became too slow, prompting the move to a formal fund.
Fund I deployed $9.99M across 91 investments; Fund II is expected to be $25–30M.
“it really came from like one time where i you know wrote an essay to help a friend who was trying to explain how his…”
#Not Boring Capital#fund origin#AngelList
?Q&A· 2
?Q&A2:40:00
Grading Not Boring with Seven Powers: Counter-Positioning, Weak Network Effects, and Process Power
The hosts apply Hamilton Helmer's Seven Powers framework to Not Boring, concluding it shows counter-positioning against traditional media/VC and process power in Packy's idiosyncratic creative process, but only weak network effects.
David identifies counter-positioning relative to traditional media and traditional venture capital structures.
Network economies are present but weak — Packy hasn't built an organized community with real network value.
Ben argues Not Boring exhibits process power because Packy can't articulate a transferable process for creating his content.
Packy agrees he's never been able to clearly explain his own creative 'process' despite being asked repeatedly.
“i've tried to explain this many times it's one of the first questions that i get from people if i go talk to a group…”
Should Packy Join a Big VC Firm? Weighing Control vs. Cash
The hosts pose a hypothetical: a big VC firm offers Packy a GP role with double-digit carry on a billion-dollar fund. Packy explains why joining in-house would strip away the independent voice that makes him valuable in the first place.
Packy argues going in-house at a large fund would immediately cost him much of his independent value (legal/compliance review, loss of spontaneity).
He frames it as a trade between long-term guaranteed carry/salary versus current control and independent upside.
Managing billions would require a completely different, less friendly, more competitive investing strategy than his current approach.
He reiterates that avoiding 'greed' (not scaling headcount or diluting focus) is what keeps his current model working.
“as soon as i go in-house somewhere like i lose half of my value or you know x percent of my value as soon as…”
“this works if i don't get greedy and this stops working if i get greedy”