Turning Content into Competitive Advantage with Packy McCormick | Founding the Fund 3

In this bonus episode of The Room Podcast, we speak with Packy McCormick, founder of Not Boring and Not Boring Capital, an investment firm focused on backing ambitious technology companies tackling large, complex industries. Through his writing, investing, and storytelling, Packy has built one of the most influential platforms in venture capital, helping founders explain difficult technical businesses to customers, talent, and investors.

Not Boring began as a newsletter during the early months of the pandemic and has since grown into a media platform reaching hundreds of thousands of readers, alongside an early-stage venture fund investing in companies across energy, aerospace, infrastructure, AI, and enterprise software. Rather than chasing trends, Packy focuses on founders building category-defining businesses that require deep conviction and long-term thinking.

In this conversation, Packy shares how storytelling became his competitive edge as an investor, why the best founders think several moves ahead of everyone else, and how developing a unique perspective can create opportunities that traditional venture firms often overlook.

Learn more about Packy on LinkedIn: https://www.linkedin.com/in/packymccormick/
Explore Not Boring at https://www.notboring.co/

(04:11) Packy's upbringing and entrepreneurial family
(05:01) Did Packy always think he would become a founder?
(05:50) Early career in finance and startups
(09:16) Starting Not Boring during the pandemic
(12:48) The first article that proved Not Boring was working
(14:04) Growing the newsletter and launching Not Boring Capital
(15:57) The thesis behind Not Boring Capital
(17:23) The first investor to back Not Boring Capital
(17:48) What Packy looks for in exceptional founders
(21:57) Building a venture firm around a personal platform
(23:56) The future of venture capital
(26:36) How storytelling creates an investing advantage
(28:45) Investing in complex businesses
(31:08) An investment that didn't go as planned
(33:19) How AI is changing writing and investing
(35:23) Advice for building an audience today
(37:05) What's next for Not Boring
(38:20) A woman who had a profound impact on Packy's life and career

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