Sunday Snapshots: 2nd anniversary edition

In which I reflect on the state of newsletters and share some lessons I have learned from writing this one for 2 years

Hey everyone,
Greetings from Washington, D.C.!

This is the 104th issue of Sunday Snapshots which means we are officially at the 2 year mark! Thank you supporting me throughout the good weeks and the bad — it's been quite a ride. I was a very different person back on 26th May, 2019. And while not all of the changes have been because of the newsletter, many have been. Certainly when it comes to being exposed to new ideas and ways of thinking, my readers and fellow newsletter writers have been my customer number one. I am grateful for your generosity and kindness every day.

Today, I wanted to skip the usual run down of books and tech analysis to zoom out and a take a look at the state of newsletters and how they interact with our culture. Then, I will share some tactical lessons that I have learned over the 2 years of writing this newsletter.

The State of Newsletters

To start out, we were quite early on the Substack train and the proliferation of newsletters as a way to build an engaged audience.

Now, it seems like everyone has one. Many have created full-time gigs out of it. It's certainly appealing in a world where the Overton window continues to shrink — for better or for worse. The written word remains ever powerful and it's somehow easier to take something on its face value when it's in text form compared to a TikTok. Writing something out gives it a sense of legitimacy. And through this legitimacy, fringe ideas can become powerful. In the age of television, society had a common narrative around what truth was.

In the internet age, there are truths. There is no culture anymore, there are cultures.

Newsletter culture has many subcultures. There is still the largely innocuous tech analysis, financial news, and curation-centered newsletters crowd of which I am a proud member of. But there are more perverse ones as well and plenty of money to support these perverse ones. You are no longer influenced by what your neighbors think. Instead, you are influenced by the person you pay $10/month to read. If a social scientist had to set up an experiment to test for confirmation bias, I doubt they could do a better job.

There is plenty of punditry on whether these changes are good or bad by people much smarter than me. My view is that these are just tradeoffs. You want to increase independence of individuals? It's inevitable that on the scale of the internet, some independent individuals might not say things that you agree with. We should certainly continue to think of sensible ways to cap the downsides (regulation like COPA is a good example), but if you want to eliminate all of the downsides you should be okay with eliminating all of the upside. My experience talking to folks in the media and on Capitol Hill tells me that these arguments are not being made in the hallowed halls of Congress and they are certainly not being made in the general public discourse.

All this was fun and games until we hit some unknown tipping point at some point in the last 10 years. The real world is now increasingly effected by the digital world. Narratives have always driven reality, but now you could drive reality anonymously from the comfort of your parent's basement in your pajamas sipping your first cup of coffee. Newsletters are a part of this trend to the extent that text is seen as the most legitimate of mediums.

Lessons learned

Over the last two years, I have been a very small (and increasingly smaller as the overall pie increases) part of this trend. As an individual writer (or any type of creator), you have to take the landscape as it is and if you see a demand wave incoming, you have decide whether you want to ride it or not. It's perfectly okay to say "no" to waves and keep doing what you're doing — you do not have to write about Bitcoin! But when you find the right wave, you have to commit.

The right wave comes with a whole host of benefits. Access to people you have no business having access to. Deep and meaningful relationships with people from all over the world. Job offers. Distraction from the daily vagaries of life. Something to anchor your week to in the middle of a global pandemic. The sense of having created something. Something to obsess over. Something where you are the creator, the preserver, and the destroyer. Something where you have full control on the gap between promises and practices.

I have also learned some more tactical things that I would like to share with other aspiring creators. While these lessons get internalized over time, it's helpful to have an eye on them:

  • Observations > Analysis: Let's say I am writing about an interesting business. I have no illusions about my ability to read a 10-K better than the hoards of investment professionals  of Wall Street. After all, understanding companies is something that we as a civilization care about and put a lot of effort into. But few, if any, analysts will have had the same life experience as me or you. That lived experience is the most valuable thing you have. The rare good pieces of writing I have done have all come when they started out with an observation. Why did the Starbucks app change its payment flow to incentivize you to pre-load a card? Why does Apple care so much privacy that it's blocking the ability of other apps to track user behavior? Why do people love Readwise so much? Why is Public blanketing my Twitter feed? How does this company that handles returns for Patagonia work? The observations are all I have to separate me from other writers and therefore are the starting point for anything I am writing about. 

  • Stay in the game: I've seen many writers come and go, but I have not yet met a single writer who has stayed in the game for more than 12 months and not seen tangible benefits from it. The initial momentum is hard to get — I encourage you to lean on others who are in a similar boat as you and keep each other accountable. But there is a certain level of discipline you need to have. I think about this newsletter in 3 month increments. Every 3 months, I ask myself, "Do I still want to be doing this?" So far, the answer has been yes. But that kind of time-boxing prevents the mentality of "I have to do this for years" and allows you to get started and stay in the game without the weekly angst of deciding whether or not you want to continue writing.

  • The need for level ups: After the initial rush of being the master of your domain, there will come a plateau where your skills start to atrophy. Your sentences will be stale and your point of views will be static. Like a video game, you'll need some level ups. For me, these levels ups have been collaborations with other writers. Over the last year, I have co-written articles on Mario Gabriele's S-1 club on Korean e-commerce giant Coupang, with Packy McCormick on how the world of HBO's hit show Succession and streaming services are the same, with Nathan Baschez on how companies evolve into complex use cases over time and the creation of opportunities for new entrants, with Jake Singer on how Lululemon appeals to everyone from 20-something females to 50-something dads, with Brett Bivens on why and how Spotify should and could get into the hardware business, and countless more through edits, messages, and Facetimes. They are incredibly fun! Writing is largely a solo sport and sometimes it's good to have a partner. There has been no single force greater than these collaborations in shaping my thinking about how companies run and how I can write about the major forces shaping the modern economy. I will continue to seek these level ups.

  • Let your personality shine through: Here's the uncomfortable truth. Most of your readers are not reading your work for the story. They are reading it for the way that you are telling that story. You have to let your personality shine through. Make sure you include that inside joke in that only long-time readers will get. Have a favorite book? Reference it whenever you can — true passion shows! Build on something you have written before and show how things have changed or stayed the same. At the end of the day, this is your playground and you make the rules. Let your work reflect that. Again, not only will this attract like-minded people, but it's just more fun than the alternative of succumbing to a particular format or trend. 

  • Keep engaging with your readers: There is no better fuel for me to continue to write the newsletter than reader comments, rebuttals, and conversations. I try to reply to every comment (even if it's sometimes not as prompt as I would like to be). It's also the right way to act with people who give you the world's only truly non-renewable resource — their time. Paradoxically, I have noticed that the bigger someone's audience is, the more engaged they are with their audience. That's not a coincidence. 

This has been a very, very fulfilling journey so far and I deeply believe that the best is yet to come. I am excited to get to know more of you and if you're ever in the D.C. area, please let me know — coffee is on me!

Until next Sunday,