Packy McCormick built Not Boring from a side newsletter into a media business and venture fund (Not Boring Capital) by following his curiosity, writing weekly essays, and investing in hard-tech companies he covers; the conversation traces his path from finance and Breather through a pandemic-era leap, the writing habits that sustain him, and the philosophical optimism that now drives both his writing and investing.
Leaving Breather and the “Not Boring Club” that never launched
After six years at Breather (a workspace startup), Packy quit in late 2019 planning a “Soho House for nerds” called the Not Boring Club, complete with a debate-club test run and lease negotiations.
COVID hit before he signed anything, saving him from a business model that would have required constant hosting — a poor fit for someone who prefers writing alone.
He realized he had become one-dimensional (work only) during finance and Breather; a conversation with his mom and her partner about “what do you do for fun?” sparked the debate-club idea as a way to reclaim hobbies.
Weekly coaching calls with his mom kept him accountable during the transition
On garden leave (Oct–Feb), he did weekly business-coaching calls with his mom, an organizational-development consultant.
The format mirrored his paid Breather coach: he talked through decisions, she asked hard questions, he talked himself into answers.
She suggested renaming the newsletter from “Per My Last Email” to “Not Boring” when it became his main focus — a pivotal branding move.
Right of Passage writing course provided the reps and the “personal monopoly” concept
Packy took David Perell’s cohort-based course in early 2020 (≈200 Twitter followers at the time) after an exec meeting where colleagues didn’t know the word “innumerate.”
The course’s main value: forced weekly output + small-group accountability; almost no one dropped out.
Key takeaway: “personal monopoly” — overlap niche interests (business + Philly sports + pop culture) so you’re the only one writing that intersection, avoiding audience capture by chasing market demand.
Passing on investing in his friend Evan Beard (now a $1B robotics founder)
Evan Beard, a college friend and early startup colleague (Shoeboxed), now runs Standard Bots — most-deployed U.S. robotics company, recently valued at $1B.
Packy didn’t invest early because they’d lost touch during his finance years; by the time he reconnected, the round was priced up.
Lesson reinforced: “always invest in your friends” — even if the specific deal misses, the relationship compounds and you support people you trust.
The “nobody gives a shit” moment freed him from audience capture
After meteoric growth in 2021–22, growth flatlined in 2023; the pressure to perform evaporated.
He realized his job (investing in exciting companies, learning from founders, writing what he learns) is secure regardless of any single essay’s performance.
Now writes deep dives and pieces like “Riding the Leopard” (meaning of life) because he enjoys both; the fund side removes pressure to optimize every post for growth.
”Riding the Leopard”: meaning of life = the universe experiencing itself through unique shards
Inspired by The Telepathy Tapes podcast (non-verbal autistic kids showing telepathy, past-life knowledge, shared visions) and Joseph Campbell’s idea of “riding the leopard” — the universe/God shards itself into limited beings to have experiences it couldn’t have as an all-knowing whole.
Cross-cultural mystical traditions (Christianity, Buddhism, Daoism, perennial philosophy) all converge on atman is Brahman; the kids were describing the same thing experientially.
Technology expands the potential for new experiences (wings, brain-computer interfaces, longevity); our role is to go have them — experience-maximizing is the point.
Optimism as a self-fulfilling choice, not blind faith
Packy’s optimism stems from a lucky life (setbacks reversed on second tries) and long-arc data (GDP per capita, health, energy).
Finds Anthropic-style pessimism “wearing” — if you assume failure, you don’t start; optimism attracts builders and becomes self-fulfilling.
Believes optimism can be practiced: his “Weekly Dose of Optimism” newsletter reframes stories (e.g., data-center water use → cooling innovation) and readers report mindset shifts.
Retired the explicit “make the world more optimistic” mission because the cultural tide has turned; current mission: “translate complex but important things so people resonate with them” — whether companies, esoteric ideas, or philosophy.
Writing process: deep-focus sprints, deadline-driven, curiosity-led research
Typical day: up ~6 AM, creatine + breakfast with daughter, in office by 8:30, mornings blocked for reading/writing (today: 4-hour uninterrupted sprint on a deep dive).
No fixed research quota; starts with founder conversations, follows gaps, uses ChatGPT for synthesis, reads case studies.
Switched sponsorship model (bulk spots placed post-hoc) to remove calendar pressure, but found the deadline itself is the forcing function that produces volume → quality (clay-pot experiment: group making many pots beats group perfecting one).
Judges pieces by input effort (research depth, clarity, capturing a company’s moment); audience reaction sometimes diverges.
Sourcing deals: inbound from writing, network compounding, attraction over funnel
No tight funnel; each top company came via a different channel (Twitter DM, founder referral, LP intro, cold inbound after a category essay).
Newsletter acts as a filter: repels misaligned founders, attracts those who resonate with his lens.
Narrowed top-of-funnel over time; now focuses on companies where his writing + audience trust is the highest-leverage value-add.
Memory, strengths, and personal-life disclosure
Admits poor episodic memory (faces, names, details) but strong conceptual recall for companies he’s studied; writing acts as external brain.
Philosophy: double down on strengths unless a weakness is life-blocking; hasn’t found memory training worth the time.
Intentionally blends personal anecdotes (kids, creatine gummies, basement writing) with serious analysis to keep voice human and AI-resistant; avoids “me show” but rejects faceless corporate tone.
Recent optimism fuel: hard tech breaking out of software-only era
Nuclear: Antares (micro reactors) raised $470M; four advanced-reactor startups went critical before July 4th — first new nuclear in 40 years.
