Strategy kernel and uncertainty window

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 Christopher Lochhead🏴‍☠️ would call creator capitalism.

For Packy, great writing is deal flow. He has invested in companies like Ramp (now valued at over $32B) and Astro Mechanica (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 and if you’re not chronically online, here is the link:

We have a wide ranging conversation including about his prior life in coworking industry and takeaways from being in that business, we talk about starting on Substack vs other platforms, business models in new media, his thesis for vertical integrators and more. 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

41:32 - Vertical integrators thesis

51:45 - Media, venture, and the future of tech media

00:00:55 - Twitter vs Substack for creators

1:10:19 - Advice to We The Builders

1:12:59 - Growing the team, getting better, and hiring

1:21:57 - Playing the long game, measuring success over decades

1:33:32 - Wrapping up — favorite shows and books

1:40:53 - Signing off

Watch on YouTube:

- Suffiyan Malik

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