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.
From the Transcript
Founder of Not Boring and Not Boring Capital. The venture fund is over 40, 50 million AUM now. The newsletter has over 250,000 subscribers now. Why Substack? You could have started, you know, you've made up your own website. I took a writing course. I took David Perel's write of passage. And one of the assignments was there's this new platform called Substack. Go set up Substack, get 20 subscribers and go. We had to pick a writer that we liked. And I picked Ben Thompson and David called it out in the 50 person class or whatever as being the best thing written that week. Oh, like maybe I can actually write. If my writing is good, the newsletter does well. If my writing is not as good, the newsletter does less well. At the same time, your business model is, you know, a venture fund. Since we're in an analysis model, how do you think RAM outpaced bricks? If they are saving companies 15% and saving them a bunch of time, what are you doing still using Amex? There are going to be a wave of companies built now that replace these like at least 50-year-old kind of companies, like the Boeings of the world. In Amex's case, 140 years old, you should try to actually go beat the incumbent. is to not go out and like try to be the very best in the industry. Like, what are you even doing?
Of the 80s and 90s. And like, they're pulling in supply chains from all over the world. And it wasn't even the wrong move at the time. Like, that was the era. You would have been punished relentlessly if you had been like, nope, we're saying full stack and vertically integrated and everything's built here in the US of A. Like the company wouldn't exist anymore. So they had to do a lot of these things, but they've gotten to the point where they are just beatable now. Like there's a whole host of new technologies that companies can build on. And if you're building one of these companies and your goal is not to be like the very biggest. In those industries, given the fact that you have a fresh sheet of paper, capital markets that are very friendly to the leading companies here, you know, Andorolka raises as much money as it wants, as one example. 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? That's what I love about these companies. Like, you should try to actually go beat the incumbent, as opposed to being like, we're, you know, going to be this component that sells into the incumbents. It's like, I don't know, just go if they like, they really need you so much. Like if, and if that component is so valuable, like use it to go compete with them.
Explain more about the uncertainty window. Yeah, so he goes through, and I'm going to blank on the name of this series, but this great series on kind of startup strategy and moats and goes through and talks about all these different things where startups actually can't get differentiated profits from all of these different things. The only thing naturally available to a startup is not, I think, counterpositioning. And he I might say this as well. Counterpositioning's job is to like extend the period that you have before someone can compete with you, but it's like not a permanent moat. But all of the other ones are like, you know, if you have IP, the value is actually like in the IP, and it's not like really something that like this, there's just like a bunch of different things where he like goes through and takes like all the different things that you know from Hamilton Helmer's seven powers about like how companies get power and like you don't have those in the beginning of a startup. The one thing he says that you do have is like uncertainty.
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