Not Boring's Packy McCormick on VC's building brand through content creation, tech trends he's most excited about, and how writing has helped him with investing.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape. This week I’m delighted to bring you my conversation with Packy McCormick, founder of Not Boring, a biweekly newsletter that now has over 100K subscribers and covers tech, strategy, finance, economics, and everything in between.  In July 2021, Packy launched the Not Boring Capital which closed at just under $10MM and has invested in over 50 companies.  Packy also started the Not Boring Club, a social and “extracurricular” community for like-minded individuals, and he also serves as a Web3 advisor for Andreessen Horowitz. About Packy McCormickPacky McCormick started his career in Investment Banking at Bank of America/Merrill Lynch, which lead him to Breather, an on-demand network of over 80 beautiful meeting spaces in New York City. In April of 2020, he started writing Not Boring, and his analysis, insight, and wit quickly grew to be one of the most-read newsletters in the startup and web3 space. He has been a big proponent in DAOs and has recently been helping to raise awareness and orchestrate how crypto investors can help the Ukrainian cause. Packy did his undergrad at Duke University. Our sponsors: At Brex, we build financial software and services to help startups scale faster. We understand that founders need to focus on building, not banking. So we’ve reimagined traditional financial systems to enable greater speed and productivity — no matter where founders and their teams are working. We offer a smart corporate card, business account, and mobile app that are easy to use from day one. No manuals needed here. Within minutes, you can deposit funds, send free wires and ACH worldwide, separate investor funds from operating expenses, earn great rewards, automate expenses, and more.  Everything we do at Brex is to help founders spend less time managing expenses and reporting on your runway — and more time building your business. Get started at brex.com/venture Why does signing up for Robinhood take 2 minutes but investing in private funds takes hours? Meet Passthrough.  The subscription document process is a nightmare. Investors receive 100-200 question questionnaires, answer the wrong questions, miss ones they're supposed to answer, and spend hours on revisions. How can you effectively manage your raise when you don't know where your investors stand? Passthrough takes any subscription document and builds a custom workflow so that your investors only see the questions that matter to them, shrinking the time to completion to minutes instead of hours. 80% of investors don't even require revisions. Plus, you can see where your investors are and coordinate them, your law firm, and fund admin to close capital quicker. At Allocate, we have used Passthrough for our various funds, which has significantly increased the efficiency of our closings while providing our investors with a delightful user experience. Go to passthrough.com/samir to learn more about how to simplify fund closing. In this episode we discuss: 02:44 Why Packy started the Not Boring newsletter07:17 Is investing a side hustle or a full-time commitment for smaller solo-GPs?09;13 How writing helps his investing12:28 Why it’s hard to understand and underwrite to exponential growth14:34 How he creates personal scale to be able to help 50+ portfolio companies17:11 Managing top of the funnel deal-flow20:02 The non-obvious trends that get him excited in web322:17 How can firms should think about de-commoditizing themselves27:27 Sizing your firm correctly and narrowing your focus29:33 Deciding when you need to change swim lanes as an investor31:11 Not Boring’s portfolio construction theory34:03 How the market continues to evolve so dynamically, and the opportunities for solo-capitalists36:45 Why do later-stage investing as a solo capitalist41:05 The speed of growth in modern startups43:58 Packy’s view on LPs50:38 The best piece of career advice he’s received I’d love to know what you took away from this conversation with Packy. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter. Podcast Production support provided by Agent Bee Agency This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com