E14: Packy McCormick on Writing, Investing, Media and Creative Process

Episode Summary

Executive Summary: The conversation centers on Becky McCormick’s path from finance and real estate startup Breather to building NotBoring, a highly successful newsletter and venture fund. She explains why Substack fit her business, how writing changed her thinking, and why depth, strategy, and a “personal monopoly” matter. The discussion expands into venture strategy, AI skepticism, and a thesis that the next wave of companies will directly replace aging incumbents through vertical integration and operational excellence.

Main Topics: Building NotBoring on Substack (Priority: 5/5): McCormick explains why she chose Substack early, how the platform’s simplicity matched a sponsor-driven newsletter, and why the core determinant of success was always the quality of her writing rather than platform features. Writing as practice, identity, and growth engine (Priority: 5/5): She describes the writing course that gave her confidence, the habit of weekly output, and the idea of a “personal monopoly” built from her overlapping interests in tech, business, pop culture, and sports. Breather, startup strategy, and lessons from operating real estate (Priority: 4/5): McCormick reflects on working at Breather, the challenge of competing with WeWork, the importance of strategy versus execution, and how that experience shaped her views on business models and operational discipline. Strategy, moats, and uncertainty windows (Priority: 5/5): She discusses Richard Rumelt’s strategy kernel, the value of coherent actions, and Jerry Newman’s idea that startups only really possess uncertainty early on before moats emerge. Ramp, Brex, and replacing incumbents (Priority: 5/5): A major theme is why Ramp’s strategy outpaced Brex: focus on saving time and money, engineering-led culture, velocity, and a clear market wedge. She connects Ramp to a broader “replacement primes” thesis targeting old incumbents like Amex and Boeing. Media, venture, and the future of tech media business models (Priority: 4/5): McCormick evaluates the rise of newsletters, podcasts, and creator-led media as venture-adjacent businesses, contrasting durable operators like Ben Thompson, Harry Stebbings, and TBPN with opportunistic entrants. Experimentation, creative process, and long-form depth (Priority: 4/5): She talks about trying podcasts, AI news products, and long research essays, arguing that depth, curiosity, and repeated iteration matter more than chasing growth metrics or virality.

Key Arguments: Substack worked because it removed friction and let the writing itself determine growth; platform features were secondary to the quality of the content. Her newsletter is sponsored, not subscription-based, so she never needed to optimize for a paywall or pay Substack. The “personal monopoly” model works because combining niche interests can create a unique audience position that is larger than it appears from the outside. Strategy matters early; execution alone can fail if the company is running in the wrong direction. Startups’ temporary advantage is uncertainty; if they move quickly and learn before competitors can copy them, moats can emerge. Ramp’s success comes from coherent strategy: save customers time and money, build products that reinforce that mission, and keep the company fast and engineering-led. Brex and Ramp differ in ambition and positioning: Brex focused on tech-company-friendly spend products, while Ramp targeted a broader universal pain point and operational efficiency. The next wave of great companies will not merely supply incumbents; they will directly replace them using better technology, systems, and business models. AI is likely to produce major consumer surplus, but many application-layer businesses may struggle to build durable moats or defensible profit pools. Writing changes how she thinks by forcing clarity, encouraging active reading, and making her more skeptical of simple answers.

Data Points: NotBoring newsletter subscribers: 250,000+ - Audience size mentioned for the newsletter NotBoring Capital AUM: $40-50 million - Size of the venture fund discussed Time since newsletter started: About 5-6 years - She says it began in the early pandemic/2019 Initial Substack audience goal: 20 subscribers - Assignment from David Perell’s Rite of Passage course Early newsletter growth: 200 to 400 subscribers in the first year - Slow early growth before going full time Twitter followers at start: ~300 followers - Most were personal followers from sports tweeting Electric Slide essay length: 40,000 words - Her long-form essay on the electric stack Historical best piece length referenced: 40,000 words - Described as her most shared piece and a major recent essay Ramp revenue milestone: $1 billion annualized gross revenue - Used to illustrate Ramp’s scale and pace Brex revenue milestone: $700 million annualized gross revenue - Compared against Ramp’s revenue trajectory Brex timing claim: Started 2 years earlier and reached $100M ARR years before Ramp - Used in the Ramp vs. Brex comparison Breather gross margins: Negative 25% - Portfolio-level gross margins on spaces before strategic reset Underwriting accuracy at Breather: 95%-98% - Model accuracy for predicting space performance One growth milestone from X payout: 15 million views / about $200 payout - She cites a viral tweet and low monetization on X

Pivotal Quotes: "If my writing is good, the newsletter does well. When my writing is not as good, the newsletter does less well." — Becky McCormick: Explaining why she prioritized writing quality over platform optimization "If your goal is to not go out and like try to be the very best in the industry, like what are you even doing?" — Becky McCormick: Her thesis on building companies that directly beat incumbents rather than supply them "The only thing naturally available to a startup is uncertainty." — Becky McCormick: Summarizing the startup advantage before moats emerge

Implications: Listeners should expect more creator-led media, more founder-investors, and more companies built to replace old giants rather than sell into them. For founders, the message is: choose a sharp strategy, move fast, and build something worth reading or using even if growth is slow at first.