E14 with @packyM about building Not Boring, new media business models, Ramp vs Brex (timely?), his thesis of vertical integrators, his creative process and more. If you’ve spent any time in tech over the past few years, you’ve probably read Not Boring or at least seen a screenshot of it on X/Twitter. Packy built it from a Substack assignment during @david_perell's Write of Passage course into one of the most-read newsletters in technology, now at over 250,000 subscribers. Encouragement goes a long way. David in that course told him his first assignment was the best piece of writing he had seen in the class which gave Packy the confidence to keep going. He talks about his fear of being made fun of (by your friends) if you publish on the internet or nobody caring and ever reading. I can relate, it is one of the reasons I recorded for 6-7 months before hitting publish in July last year. The funny thing is, 250,000 subscribers later that feeling never completely goes away. We touch on that too. Every Not Boring essay is a full-stack teardown, part history lesson, part strategy memo, part “why this would matter in 10 years.” Today, Packy sits at the intersection of media and venture, David Perell described this new era of creators and personalized business models as building a personal monopoly. This applies to podcasting, newsletters or blogs and any other form of new media at the intersection of tech and business where the differentiation lies in the creator - they are like Hollywood talent and the brand they represent is secondary and in some cases irrelevant. They are the brand. We live in the era of what my friend @lochhead would call creator capitalism. For Packy, great writing is deal flow. He has invested in companies like @tryramp (now valued at over $32B) and @AstroMechanica (bringing back supersonic air travel) and many more through his fund. What he now spends most of his time on is doing well researched deep dives which are a function of the relationships he builds along the way. If you are chronically online on X/Twitter, you would have seen his latest masterpiece, a deep dive on @a16z. Hope you enjoy! Timestamps: 00:00 - Intro 01:11 - Why publish on Substack and the origins of Not Boring 01:42 - Write of Passage with David Perell 04:51 - The content pyramid and compounding experiences 15:46 - Insights from working in co-working industry 28:07 - The Ramp case study and the concept of uncertainty window 36:56 - Ramp vs Brex ...