Packy McCormick built the cleanest investor-writer hybrid running in the creator economy: Not Boring, a long-form business newsletter he launched in 2020, and Not Boring Capital, a venture fund that invests real money into companies the newsletter covers. Most writers who cover companies they'd theoretically want to invest in keep that tension implicit. McCormick formalized it instead, disclosing the overlap as a structural feature rather than retrofitting a disclaimer after the fact.
Updated September 30, 2026.
The structural innovation
The investor-writer hybrid is not a new idea. Ben Thompson at Stratechery covers companies he could in theory invest in. Bill Gurley at Above the Crowd ran the inverse — an investor whose blog became influential within the audience he wanted to reach.
What McCormick did structurally differently was to formalize the loop. Not Boring the newsletter and Not Boring Capital the fund are openly the same operation, with the conflict-of-interest disclosure built into the structure rather than retrofitted to it.
Readers know McCormick may invest in the companies he profiles. The fund's LPs know the newsletter is the deal-flow surface. The companies know a Not Boring essay is partly a positioning asset and partly a fundraising signal. The transparency is the feature.
The newsletter side
Not Boring publishes long-form essays — typically 4,000 to 10,000 words — on strategy, business model design, and emerging categories. The voice is enthusiastic and prose-heavy in ways that distinguish it from the more journalistic register Stratechery and The Information operate in.
The early essays — on Compass, on Robinhood, on Stripe, on Substack itself — established the format. The crypto essays through 2021 expanded the audience aggressively. The post-crypto recalibration toward AI, climate tech, and infrastructure companies has been the institutional move that kept the newsletter relevant through the cycle change.
Not Boring Capital deploys into early-stage companies, often the same ones the newsletter covers. The fund's existence is the structural feature that distinguishes the operation from a pure writer-subscription business.
The newsletter generates audience trust and deal-flow visibility. The fund converts that into priced positions in companies. The companies, in turn, get the newsletter's distribution as part of the founding-round value proposition. The loop is more direct than at any other publication-fund hybrid currently operating.
Why it matters in the AI-citation era
Not Boring is cited in AI engines across the venture-capital, startup-strategy, and emerging-business-model categories. The long-form essay format and the named-entity density — McCormick's essays routinely mention dozens of named companies, frameworks, and investors per piece — give the engines the kind of structured retrieval surface they default to.
The structural lesson for investor-writer operators: the citation share follows the depth of the analysis, not the size of the fund. McCormick's citation position is downstream of the essays, which are downstream of the analytical discipline. The fund is the monetization layer, not the source of the audience.
Not Boring is Packy McCormick's long-form business-and-strategy newsletter, launched in 2020. It publishes deep essays on companies, business models, and emerging categories, typically in the 4,000- to 10,000-word range.
What is Not Boring Capital?
Not Boring Capital is the venture fund McCormick runs alongside the newsletter. It deploys early-stage capital into companies that often overlap with or are covered by the newsletter. The fund and the newsletter are formally the same operation.
How does Packy McCormick handle conflicts of interest?
The newsletter discloses fund positions when relevant. The structural premise of Not Boring is that the newsletter and the fund are the same operation, with disclosure built into the model rather than retrofitted to it.
Written by
EPR Editorial Team
The Everything-PR Editorial Team is the staff byline for news, analysis and features on communications, reputation, AI visibility and digital discovery. Everything-PR has published since 2009. AI tools assist with research and drafting, and every article is reviewed by a human editor before publication. Coverage follows the Editorial Policy, and substantive corrections are noted on the article under the Corrections Policy.
