Not Boring (with Packy McCormick)

Episode Summary

Executive Summary: Acquired profiles Packy McCormick and the rise of Not Boring as a one-person media and investing empire. The episode traces Packy’s path from finance and startup operations to newsletter writer, sponsor innovator, and venture investor, emphasizing his optimism, original voice, and emergent strategy. It also explores how platforms like Substack and AngelList enabled a new solo-corporation model.

Main Topics: Packy McCormick’s formative path (Priority: 5/5): Packy’s childhood love of writing, class-clown energy, work ethic, Duke debate/a cappella background, and early finance/startup experiences all shaped the voice and diligence behind Not Boring. Breather as a proving ground (Priority: 5/5): His years at Breather taught him operations, real estate, design, hiring, and strategy, while also showing him how to turn around a business with disciplined strategic thinking. Birth and growth of Not Boring (Priority: 5/5): Not Boring began as an experiment in writing and community-building, then evolved into a newsletter with rapid audience growth, a distinct optimistic worldview, and eventually a real business. Sponsored content as product innovation (Priority: 5/5): Packy reframed sponsored posts as high-quality, transparent, value-added deep dives rather than low-trust ad units, creating a new media monetization model. Web3, optimism, and intellectual positioning (Priority: 4/5): Packy’s move into crypto/Web3 content reflected his broader thesis that new tools can expand the design space for creators, companies, and communities without abandoning business fundamentals. Not Boring Capital and the solo-corporation model (Priority: 5/5): The newsletter’s influence created a venture investing engine, with AngelList and the audience flywheel enabling Packy to invest in startups without a traditional VC platform. Constraints and trade-offs of a one-person empire (Priority: 4/5): The episode closes by examining the limits of Packy’s model: key-person risk, scalability constraints, and the challenge of growing without diluting the core product.

Key Arguments: Packy’s success is not accidental; it is the result of a lifelong mix of curiosity, writing talent, work ethic, and a willingness to do operational grunt work. Breather was a crucial apprenticeship because it exposed him to the realities of startups: leases, cleaning, design, operations, team management, and strategic turnarounds. Not Boring grew because Packy stayed authentic, wrote in his own voice, and treated audience trust as the foundation of everything. Sponsored posts can be legitimate if they are fully disclosed, analytically rigorous, and genuinely useful to readers and founders. Traditional journalism incentives often reward cynicism and shallow gotcha coverage, while Packy’s model rewards optimism, transparency, and practical analysis. Web3/crypto should be analyzed through business and incentive structures, not hype; the point is to explain what is possible, not to dismiss or canonize it. Not Boring Capital is an emergent extension of the media business, turning audience, credibility, and insight into direct investing advantages. A one-person media/venture business can scale meaningfully only if it avoids greed and stays tightly aligned with the founder’s core strengths. The main source of defensibility is not audience size alone, but the specific alignment among content, audience quality, and investing. Packy’s model is powerful but fragile: if he stops writing or starts stretching too far beyond his core voice, the whole system could weaken.

Data Points: Acquired subscriber count at episode open: 88,460 - Ben time-stamps Acquired’s subscriber count at the start of the episode and jokes the episode is a failure if they don’t cross 100K. Packy Twitter followers (Feb. 2020): 956 - Used as a benchmark early in Not Boring’s growth. Packy Twitter followers (later in 2021): ~105,000-106,500 - Referenced as evidence of rapid compounding and audience growth. Not Boring newsletter subscribers (later in 2021): ~88,000 - Packy notes he now has more Twitter followers than subscribers. Not Boring age: About 1.5 years - Highlighted as unusually fast growth for such a young publication. Packy target annual revenue tweet: $1 million - He tweeted that he wanted Not Boring to make $1 million in 2021. Estimated 2021 revenue: ~$750,000 in Mercury account + outstanding invoices/checks - Packy says the business is likely to cross $1 million in 2021. Probability of hitting $1M in 2021 (Packy estimate): ~20% - His personal estimate of achieving the goal when he tweeted it. First newsletter audience size for ad deck: ~10,000 subscribers/followers range - He says the first sponsorship deck and advertiser outreach happened around this scale. Initial audience in Per My Last Email: ~400 people - Used to start the early community and test the Not Boring Club concept. Early Not Boring Club applicant/member cohort: ~150 people - Early community dinners and Slack groups were built around this group. Breather team size in New York: ~25 people - By the time Packy’s New York team grew, it was a major part of company revenue. Breather company size at broader scale: ~150-person team - When he became VP of Experience, he oversaw a large cross-functional organization. Breather markets: 10 markets - Packy says his New York team represented about half the company’s revenue across 10 markets. Breather margin turnaround: -25% to +25% gross margins - Packy and Ben Rollert helped turn the business around over Christmas break. Not Boring LP fund size (Fund I): $9.99 million - Packy notes the first fund was intentionally set just under $10M. Not Boring LP fund size (Fund II): $25 million - Packy says the next fund was about $25M, potentially $25M-$30M. Not Boring investments: 91 - Packy states he made 91 investments through the fund. Crypto/Discord audience reaction: Massive Twitter spike - A Discord/Web3 piece and the ensuing Discord CEO reply drove a large surge in followers. Audience sponsor demo: 25-34 age range, high income, leadership, decision makers - Packy used audience characteristics to sell sponsorships. Early sponsorship revenue aspiration: $300K-$400K - Packy initially thought the newsletter might eventually make this much from sponsorships. Baby birth date: October 4, 2020 - Packy’s son Devin was born while he was still writing Not Boring.

Pivotal Quotes: "I don't even own serious business pants." — Packy McCormick: Packy explains that his writing style is rooted in being himself rather than adopting a corporate persona. "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." — Packy McCormick: He explains why authenticity is essential to his media business and online growth. "The reason it works is because you don't put on your serious business pants." — Ben Gilbert: Ben summarizes why Packy’s tone and voice resonate with readers.

Implications: Packy’s story suggests that solo media/investing businesses can scale when they combine authentic voice, transparent monetization, and a strong audience-product fit. It also signals a future where creators can become capital allocators without losing independence.