Dec 3, 2021 · 3h 5m · acquired
Not Boring (with Packy McCormick) - Extended Cut · Acquired
Packy McCormick · 1h 44m spoken Ben Gilbert · 38m spoken David Rosenthal · 27m spoken Intro/Outro Singer · 4s spoken
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In this extended episode of Acquired, hosts Ben Gilbert and David Rosenthal conduct a comprehensive business strategy breakdown of Packy McCormick's Not Boring, analyzing how he built a leading business newsletter into an innovative solo corporation combining media distribution and venture capital investing.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Ben and David hold 39.3% of the talking time here. How this is scored →
Ben and David as informed peer 3.8 Guest teaching 2.0 Guest disagreement 0.3 Ben and David pushing back 0.6
speaking balance: gold is Ben and David, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:17:30 Packy's Pushback on Cynical Tech Journalism
Packy forcefully rejects the cynical framing of tech journalism that subjects seed-stage startups to investigative hit pieces normally reserved for political scandals.
Hardest push from Ben and David ▶ 1:25:34 Ben Challenges the Value of Sponsored Deep DivesBen directly challenges Packy on the perception that Thursday sponsored deep dives lack the broad strategic resonance and independence of his Monday editorial pieces.
Biggest teaching moment ▶ 2:37:25 Reframing Audience Size vs Founder Affinity in VenturePacky educates the hosts on deal flow mechanics, demonstrating that raw audience size is irrelevant to winning venture allocation unless the founder is already a genuine reader.
Ben and David hold their own ▶ 2:43:20 Hosts Deconstruct Not Boring Using 7 PowersBen and David demonstrate deep strategic expertise by rigorously applying Hamilton Helmer's Seven Powers framework to categorize Packy's business model under process power and counter-positioning.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Ben and David as informed peer | Guest teaching | Guest disagreement | Ben and David pushing back | Why |
|---|---|---|---|---|---|---|
| Public Launch of the Acquired LP Show | 0 | 0 | 0 | 0 | Introductory housekeeping and sponsor segment announcing the public release of The Acquired LP Show back catalog followed by a presenting sponsor read for Pilot. As a monologue and sponsor presentation, host and schooling metrics remain zero. | |
| Disclosures and Defining the Founder Role | 3 | 1 | 0 | 0 | Hosts disclose LP investments in Not Boring entities and open up Packy's background. Packy shares humorous childhood anecdotes about drawing early mini-newspapers and navigating school essays. | |
| Parental Work Ethic and the Loser Box | 3 | 2 | 0 | 0 | Packy explains his family work ethic, recounting his father's 'loser box' lesson and his early career on Bank of America's energy trading desk post-Enron merger. The hosts engage collegially on shared experiences in 2007-2009 finance. | |
| The Throgo Party Bus and Skipping Business School | 3 | 2 | 0 | 1 | Packy recounts starting his Hamptons party bus business Throgo, turning down Chicago Booth, making bad early stock/crypto trades, and applying to Breather. Ben jokingly challenges Packy's spin on framing a party bus company as a community venture. | |
| Breather Hypergrowth and Strategic Turnaround | 4 | 3 | 0 | 0 | Packy details his six years at Breather, from cleaning rooms via Uber Rush to engineering a strategic margin turnaround using frameworks from Ben Thompson and Good Strategy/Bad Strategy. | |
| Leaving Breather and the Not Boring Social Club | 3 | 1 | 0 | 0 | Packy details leaving Breather on sabbatical in Japan and attempting to launch the Not Boring Club as a physical social club right before COVID-19 shut down in-person gatherings in March 2020. | |
| Pivoting to Digital and Finding Early Traction | 3 | 2 | 0 | 0 | Packy recounts pivoting to digital essays, launching on Product Hunt, and making the decision to write under his authentic persona rather than an engineered online character. | |
| Ad-Supported Model vs. Paid Subscriptions | 4 | 2 | 0 | 1 | Packy and the hosts dissect the trade-offs between paid subscription paywalls and free ad-supported growth. The hosts explain conversion fallacies while Packy explains why generalist cultural strategy fit ad models better. | |
| Financial Break-Even and Fast-Food Nostalgia | 3 | 1 | 0 | 0 | A nostalgic and personal segment discussing living in his in-laws' basement, reaching financial breakeven quickly, and regional fast food favorites like Wawa and Swensons. | |
| Pioneering the Sponsored Deep Dive | 5 | 3 | 2 | 1 | Packy explains how he pioneered the sponsored deep dive format with Main Street and Ramp. He contrasts full disclosure with traditional tech journalism, expressing frustration with cynicism and hit pieces targeted at early startups. | |
| Optimism, Analytical Limits, and Radical Transparency | 5 | 2 | 1 | 2 | Ben pushes Packy on the quality gap between Monday analytical essays and Thursday sponsored posts. Packy concedes that Thursday pieces have narrower design spaces and admits his optimism would have made him vulnerable to missing issues like Theranos. | |
| Independent Creators vs. Traditional Journalism | 5 | 3 | 1 | 2 | Ben raises macro concerns regarding whether independent creator models erode traditional fourth-estate journalism. Packy clarifies that institutional journalism is vital for investigative accountability but misplaced when applied cynically to early startups. | |
| Compounding Metrics and the $1M Revenue Goal | 3 | 2 | 0 | 0 | Packy reviews the compounding inflection point of early 2021, including reaching Hacker News top ranking with his Excel essay and publicly aiming for a $1M revenue target on Twitter. | |
| Exploring Web3 and Decentralized Communities | 4 | 3 | 1 | 1 | Packy traces his transition into Web3 analysis, ConstitutionDAO involvement, and applying traditional business strategy to evaluate crypto protocols like Solana without ideological extremism. | |
| The Solo Corporation and Not Boring Capital | 4 | 3 | 0 | 0 | Discussion centers on Packy's concept of 'solo corporations' and how Not Boring Capital transitioned from AngelList syndicates into Fund I without hiring traditional support staff. | |
| Redefining Early-Stage Portfolio Construction | 5 | 2 | 0 | 1 | Packy transparently acknowledges doing minimal traditional due diligence across 91 investments, relying instead on leading VC partners and power law upside. David and Ben discuss the mathematical validity of power law venture investing. | |
| Sponsor Spotlight: PitchBook | 4 | 2 | 0 | 0 | A sponsor transition to PitchBook leads into an architectural discussion of how platforms like AngelList act as 'AWS for venture capital', allowing single-person funds to unbundle the traditional VC stack. | |
| Vulnerabilities and Limits of Solopreneurship | 5 | 2 | 0 | 1 | Ben outlines the classic startup transition from founder-operator to organizational executive. Packy highlights why that playbook fails for creator businesses where the individual is the indivisible product. | |
| The Growth Ceiling of Individual Media | 4 | 2 | 0 | 1 | Discussion on the growth ceiling and S-curve saturation for solo newsletters. Packy explains his competitive wedge in translating the near future and worries about navigating potential tech bear markets. | |
| Late 2021 Acceleration and a16z Advisory Role | 4 | 2 | 0 | 0 | Packy details his surge in late 2021, including co-authoring an essay in The Economist with Chris Dixon and stepping into an advisory role at Andreessen Horowitz Crypto. | |
| Analyzing the Not Boring Flywheel and Founder Fit | 4 | 2 | 0 | 1 | Packy breaks down his flywheel, clarifying that audience size is not a transactional currency for deal flow; rather, deal access depends strictly on whether the founder is an authentic reader. | |
| Applying the Seven Powers Framework to Not Boring | 6 | 2 | 0 | 1 | Hosts apply Hamilton Helmer's Seven Powers framework to Not Boring. They dismiss scale economies, evaluate counter-positioning and weak network effects, and converge on process power as the defining competitive advantage. | |
| Sponsor Break: NordVPN | 5 | 2 | 1 | 2 | Following a NordVPN sponsor break, hosts present a hypothetical dilemma: joining a multi-billion dollar VC firm as general partner versus remaining independent. Packy explains why going in-house destroys his core value and independence. | |
| Acquired Carve-Outs and Sci-Fi Book Recommendations | 3 | 1 | 0 | 0 | Hosts and guest share personal carve-outs covering infant swaddling techniques, Pioneer Square Labs' technical Web3 post, and sci-fi book recommendations including Rabbits, The Expanse, and Red Rising. |
Statements from this episode (39)
Gilbert: Not Boring is the number one business newsletter on Substack
“I did some research last night. Not Boring is the number one substack newsletter on business.”
McCormick: Wrote roughly one million words for Not Boring in 18 months
“It's been probably close to a million words in a year and a half at this point.”
McCormick: BofA's 2008 energy trading desk was staffed by ex-Enron personnel
“Bank of America's energy trading desk was all ex Enron people.”
McCormick: I bought 38 Bitcoin at $100 and sold at $150
“I bought Bitcoin at a hundred, sold it at one 50.”
McCormick: I was the largest Uber Rush consumer worldwide during Breather's expansion
“We actually, I was the largest consumer of Uber rush messengers in the world for a while.”
McCormick: Breather launched a space daily in 2016-2017, crushing gross margins
“We added a space per day in. 2016, 20 17 for about a year there. Every day we were launching a new space. And so we were deeply oversupplied. Our gross margins were awful, negative, I think -25%.”
McCormick: A DAO with physical locations is perfect for modern social clubs
“I mean, today, what not boring club would have been is really a Dow probably with physical locations. I think actually that model works really well for what I was trying to do at the time.”
McCormick: Playing an online persona makes creator work unsustainably difficult
“If you're not yourself, it's not like a be true to yourself kind of thing. It's like, you're going to have a miserable experience because all of your interactions are going to be other people wanting to interact with this persona, or if I were writing from a d…”
Gilbert: Creators typically convert at best 2-3% of audiences to paid subscriptions
“Creators can typically convert at best two to three percent to a paid offering unless they're significantly handicapping the main content where you'd say like, sorry, every other main post is behind the paywall or something, you know, big like that.”
McCormick: Paid newsletters succeed when companies expense them for specific roles
“Lenny's audience is so specific and like, you know exactly who you are and who should be paying for that, which is people who do product or people who do growth. And not only do they know that they should be reading that and that they need to pay for it, their…”
Rosenthal: Most Wall Street Journal subscriptions are expensed by employers
“Most people who pay for the journal, it's their companies that are paying for the journal.”
Gilbert: Creator businesses transition through financial break-even remarkably fast
“The period of time where Hey, this isn't going to cover our lifestyle is long. And then, Hey, the period of time where, Whoa, this is going to more than cover our lifestyle is long. But the period of like, Hey, this is great. We're like right at break even sus…”
McCormick: Substack is completely free for Not Boring's ad-supported model
“The most beautiful part about sub stack is because they've taken such a strong stand for subscriptions and against advertising. No one on their team has ever even reached out to me. And so I paid zero dollars for my main platform because they want to pretend l…”
McCormick: A tech bear market will lead to attacks on my optimism
“I think when the market turns and when we enter a bit of a bear market and in tech and web three, like it will be really easy to throw stones at me. Like I am unabashedly optimistic about all of this and like things are going to turn on. I'm going to like, you…”
McCormick: I likely would have written a positive sponsored post on Theranos
“One of the tests that I always run for myself, and I probably actually would have failed this test, is if Theranos had come to me on a sponsored post, you know, however many years ago, chances are, frankly, I would have written something positive on Theranos b…”
McCormick: Ramp raised at $1.1B and $1.6B valuations in one deal
“It was ramp. And like they're kind of double unicorn round when they raised at a 1.1 billion dollar valuation and a 1.6 billion dollar valuation in the same transaction.”
McCormick: Independent investigative journalism is severely limited without institutional legal backing
“I think it's really hard to do that kind of journalism. Independently because you need lawyers who have your back and you need editors to make sure that you get everything right. And you need like all this stuff to protect you when you're doing this really bra…”
McCormick: Startup where I worked sold for $3M after raising $120M
“I was an employee, not a founder. At a startup that sold for three million dollars after raising a hundred twenty million dollars.”
McCormick predicts Not Boring will cross $1M in revenue in 2021
“And I have a few pieces kind of coming up, and so I think chances are we're going to just kind of cross a million dollars in 2021.”
McCormick: Not Boring reached 105,000 Twitter followers and 88,000 newsletter subscribers
“I'm like, you know, a 105 or something on Twitter and 88 in the newsletter.”
McCormick: 80% of DAOs will fail, but the top 20% outperform corporations
“I think Eight out of 10 DAOs might totally fail because they have like kind of that leadership issue or like who is the final decision maker issue. But I think those other two are going to do things that like you might not have ever thought to do with a tradit…”
McCormick: Solana's token increased 3.5x two months after his deep dive
“And then of course, Solana, like three and a half X in the next two months.”
McCormick: Running a venture fund scales better than writing sponsored newsletters
“It does scale a lot better to run a venture fund than to show up every week and get a sponsor and then write, write an essay.”
McCormick: I made 91 investments in Not Boring Capital Fund 1
“Fund when I did fund when I did 91 91 investments and not all of them have investment memos.”
McCormick: Not Boring Capital never led a round across 91 investments
“Did you lead a single round? Did you write any term sheets? Were you the biggest check in any one of those 91 investments? Never. And that's all part of the strategy, right?”
McCormick: Not Boring Capital does less diligence than most co-investors
“I wrote in both the public and private memo that like I'm doing probably less diligence than most people on a specific company than most people who are investing in a company will.”
McCormick: Not Boring Fund II would potentially target $25M to $30M
“And fund two, were it to exist would potentially be in the 25 to thirty million dollar range.”
McCormick: Not Boring has severe key-person risk and momentum slows without me
“If I get hit by a bus, like not boring is just done. And that's like the extreme example and the example that everybody uses when they talk about one person things, but that means that like every week, if I don't show up and write something, the momentum slows…”
McCormick: Expanding creator brands beyond core content risks turning into shill factories
“The more I do of that stuff, the more dilutes the core thing. And the more it makes it seem like kind of a shill factory”
McCormick: Not Boring can reach 1M subscribers within five years
“There's a path to this being a million person newsletter at some point in the next five years.”
McCormick: Not Boring adds 1,000 to 2,000 subscribers per week
“It still grows a thousand to 2000 people a week, the newsletter, but a thousand to 2000 people a week is a lot different when you're at 40,000 versus 80,000.”
McCormick details the scope of his advisory role with a16z Crypto
“The advisory there is like, you know, working with some of the companies in their portfolio to think about how they tell their story, writing pieces. Like I wrote with Chris in the economists, like they'll introduce me to companies, you know, that they've inve…”
McCormick: Becoming a full-time VC partner would never be attractive
“I've had that other conversation with funds, too, where it's like, hey, you want to come work and, you know, be a full-time partner at this fund? And no, like, we've talked for the past couple of hours about how much fun I'm having doing this particular thing,…”
McCormick: Winning founder allocation depends on if they are already active readers
“I don't think it's gotten, you know, any easier convincing founders to give me allocation at 50,000 readers or 88,000 readers. Like if they're a reader, then they kind of get it. And if they're not, then You know, they don't on the sponsorship side. It's diffe…”
Gilbert: Public market swings reflect long-term horizons, not short-termism
“Actually, public company shareholders are not short-term oriented. They're long-term oriented, and that's why when you change your guidance for the next quarter, the valuation can change by billions and billions and billions of dollars because people are accou…”
McCormick: I will not raise outside venture capital for Not Boring
“I think I don't want to raise money because then I'd have bosses and I don't think I'd get a valuation that I'd be happy to sell part of myself for.”
McCormick: Independent creator-investors lose value when joining traditional venture firms
“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 I go in-house somewhere. And that is kind of one, even though, you know, I do do sponsored posts and all of that, there is like this independent voi…”