Not Boring Top 10

The Five Most Popular Not Boring Posts So Far + Five Personal Favs

Welcome to the 186 newly Not Boring people who have joined us since Monday! If you’re reading this but haven’t subscribed, join 19,881 smart, curious folks by subscribing here!

🎧 You can listen to all but the oldest of today’s posts on Spotify.


Hi friends 👋,

Happy Thursday! 

Since turning Per My Last E-mail into Not Boring on April 2nd, I’ve sent out 54 newsletters. They’ve been viewed over 800k times. That’s wild. 

THANK YOU! It blows my mind that I get to do this as my full-time job, and it’s only because so many of you have been generous enough to give me some of your time to read, listen, share, and give feedback. Particularly big thanks to everyone who’s achieved Not Boring Verified status in the referral program, including new additions Sean McCarney, Joaquin Mencia, and Joel Montano

I haven’t counted the words in all the posts, but it’s right around a quarter million. That’s a lot. There are about to be more than 20 thousand of us here, so I wanted to look back and share the five most popular Not Boring essays plus five of my personal favorites from back in the day :) 

But first, a word from our sponsor… 


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 Now let’s get to it… 


Not Boring Top Ten

In an excellent essay on the rise of community-curated knowledge networks, my friend, long-time reader, and future collaborator Sari Azout wrote: 

Our feed-based information architecture is obsessed with the present. Substack makes this worse. How often have you gone back to read an old issue of your favorite newsletter? Why bother when you’ll have a new one soon?

It’s true. I try to write essays that relate to current events but retain their usefulness over time. A company’s founding story never changes (although the way the company tells it often does), and its narrative and drivers remain fairly consistent over time barring a major pivot. But because there’s going to be another 5,000+ words in your inbox on Monday, if you didn’t read an essay the week it came out, chances are you never will. 

Since the majority of you have joined this party in the past three months, I’m sharing the five most popular Not Boring essays and five of my personal favorites from over three months ago. One last chance to look back with the original Not Boring crew before there are more than 20,000 of us here next week 😮  

I want to try an experiment: I’ve included a link on each essay that automatically generates a tweet. Click to share your favorite, timestamp that you’re one of the first 20k here, and help our family grow. It’s a little cheesy, but I think it’ll be fun. 

Top 5 Most Popular of All-Time

Tencent, Stripe, Opendoor, and Reliance are four of the most fascinating companies out there, and despite the fact that they’re at very different stages, I think the best for all of them is yet to come. Their stories, and how software is eating the markets, are the most popular Not Boring essays of all-time.

1. Tencent: The Ultimate Outsider - August 17, 2020 🏆

Two sentence summary: Tencent is the world leader in gaming, runs the largest messaging, social networking, and mobile payments platform in China (WeChat), and owns one of the world’s most impressive portfolio of tech investments. It’s the most important company that westerners know the least about, and it might become the most valuable in the world. Tencent reported Q3 earnings this morning and beat.

Share Tencent: The Ultimate Outsider

2. Stripe: The Internet’s Most Undervalued Company - August 31, 2020

Two sentence summary: Stripe is so loved that it’s underanalyzed and deeply undervalued at its most recent $36 billion valuation. The Collisons are building one of the most impressive companies in the world, and one with all Seven Powers. 

Share Stripe

3. Knock Knock. Who’s There? Opendoor. - September 21, 2020

Two sentence summary: Opendoor, the iBuyer that Chamath is taking public via SPAC, has a chance to become the Amazon of housing… if Amazon doesn’t buy it first. Plus, it has the best company value out there: bps for breakfast.

Share Opendoor

4. Reliance’s Next Act - October 19, 2020

One sentence summary: Reliance is the most important company in India by a wide margin -- it’s the gateway to India for foreign companies and runs the country’s data and retail infrastructure -- but it should loosen its grip and invest in the next wave of Indian unicorns to maximize its potential.

Share Reliance's Next Act

5. Software is Eating the Markets - October 26, 2020

Two sentence summary: Consumer investors are shifting money from consumption to investment. They expect different things from their investments than professionals do and value assets differently as a result.

Share Software is Eating the Markets

My Five Favorite OG Essays 

Not Boring is still young, so OG is relative, but more than half of you weren’t here three months ago. Here are my five favorite early Not Boring essays. 

1. Oh Snap! - June 15, 2020

Two sentence summary: Everyone left Snap for dead, but Evan Spiegel is executing on a long-term plan that puts Snap in the driver’s seat to own the Augmented Reality layer, or Mirrorworld. Plus, a good overview of one of my favorite frameworks: the Gartner Hype Cycle. Snap is up 92% since that post 🤯

Share Oh Snap!

2. If I Ruled the Tweets - July 13, 2020 

Three sentence summary: Twitter captures less of the value it creates than any major tech company, because it thinks it’s Facebook, but it’s really LinkedIn. Four ideas for how to fix it. Twitter hasn’t done much since then, but its stock is up 22% 🤷🏻‍♂️

Share If I Ruled the Tweets

3. Schumpeter’s Gale - April 20, 2020

One sentence summary: Things looked bleak in April, with a new wave of layoffs announced daily, but in many ways, it was an act of creative destruction that freed people from bullshit jobs and allowed them to pursue better opportunities. 

Share Schumpeter's Gale

4. Shopify and the Hard Thing About Easy Things - August 10, 2020 

One sentence summary: Here’s the hard thing about easy things: if everyone can do something, there’s no advantage to doing it, but you still have to do it anyway just to keep up. 

Share Shopify

5. Earshare: The Idiot’s Guide to Investing in Spotify - March 2nd, 2020

Four sentence summary: It’s almost impossible for a regular investor to beat the market by analyzing the numbers, but we can understand the narrative around a company and whether we expect that narrative to crack. In Spotify’s case, the narrative was that it had shitty margins because of its deals with the record labels, and I thought that good news about podcasts would crack it. In May, Spotify announced a deal with Joe Rogan and the stock has been a winner since. This was the first time I wrote a deep dive on a publicly traded company, and we’re up 89% since! 

Share Earshare

Not Boring Syndicate & SkillMagic Update 

The Not Boring Syndicate has been one of the unexpected highlights of this year for me. Since Fed and I decided to write up a memo on his company, Apt, in July, we have completed three seed investments -- Composer, OZE, and Swaypay were all oversubscribed -- and are working on #4 now. 

SkillMagic, our current deal, is wrapping up soon! Since the investment memo, Jason has brought on an all-star cast of angels and after the Syndicate’s Q&A with Jason, I could not be more excited about SkillMagic’s potential to reshape remote training.  Join the syndicate to learn more, get involved, and stay in the loop on future deals.

Join the Not Boring Syndicate

Thanks for coming along on this journey so far. We have some exciting things in store when I finally start sleeping through the night and my brain starts working again, and I can’t wait. 

Thanks for reading, 

Packy