Welcome To Stew's Letter

For those who haven't subscribed yet, I recently launched Stew's Letter - a weekly email where I send out my best stuff. This was the introduction to the first email. Enjoy!

So, it turns out that sitting down to write an email for a bunch of smart people is pretty terrifying.

It didn’t take long to go from “I am a genius with many great ideas” to “all of my ideas are either obvious or wrong and sending out a newsletter will only confirm people’s suspicion that I am actually just an idiot.”

But, I’m going to fake some confidence and hit publish anyways.

This all started last year after an amazing, but intense and stressful, few years working on a startup. I was completely burned out and decided to take a months-long sabbatical to figure out what the hell to do next.

The goal was to get up to speed on all of the insane things happening in the tech industry and to start working on something in the most promising field. That goal was mostly accomplished, but it blows my mind how much time I wasted and how many dead ends I went down.

My “sabbatical” was really just an extended period of unemployment, filled with the same temptations to waste time and lose whatever momentum I had in a past life. It didn’t take long for the typical day to start looking like this:

  • 7:02 AM: Start pot of coffee
  • 7:03 AM: Habitually refresh email even though nobody is actually trying to email me because I do not have a job
  • 7:07 AM: Write
  • 7:45 AM: Decide that today is the day I’ll figure out what Bitcoin is
  • 8:01 AM: Read highly-biased article claiming Bitcoin will cripple world governments
  • 8:45 AM: Buy Bitcoin
  • 9:01 AM: Read article claiming Bitcoin is a Ponzi Scheme
  • 9:32 AM: Sell Bitcoin
  • 10:01 AM: Realize that neither author actually knew what Bitcoin was
  • 10:11 AM: Realize that, also, I forgot about that pot of coffee
  • 10:14 AM: Start second pot of coffee
  • 10:18 AM: Try to find writers who actually understand Bitcoin
  • 10:19 AM: Forget about second pot of coffee
  • 3:06 PM: Realize that I was not able to actually convert coffee grounds into something drinkable today and it’s like 3 PM so I’m not going to do it now
  • 3:07 PM: Give up on Bitcoin research
  • 3:56 PM: Write code
  • 8:45 PM: Ask girlfriend where those THC mints are
  • 9:23 PM: Start reading an amazing book
  • 9:44 PM: Realize that this isn’t a book, it’s the mint container. Remember how strong these mints are. Pledge to never eat them again.
  • 10:12 PM: Enter a deep slumber

That probably doesn’t sound terribly productive, but, amazingly, I managed to do more reading, reflecting, and writing than any other time in my entire life.

When I reviewed a bunch of what I wrote, it struck me that it might actually be useful - or even just entertaining - for other people too. You all don’t need to spend a few months pacing around your apartment like an insane person. I’ve done that on your behalf and put the results in this email.

This will be a collection of the types of things I’ve written over the past few months, which mostly consist of tech commentary, trivial observations, speculation about the future, nuggets of wisdom, and literally just uninformed, unfiltered rants.

Thank you for taking a risk on this and I hope you love it.

Haters, the “unsubscribe” link is at the bottom.

To everybody else, welcome to Stew’s Letter.

Interesting Factoid That Recently Expanded My Worldview

Quantity = Quality

Scott Dikkers (founder of The Onion) wrote that the best ideas in the writers' room tended to come from generating the most ideas. The average quality of the ideas didn't matter, it was all about generating more and more ideas in general.

That's backed up by some fascinating research (summarized by Marc Andreessen here) that found ultra-successful people tended to produce their best work during the periods in which they produced their most work.

"The periods of Beethoven's career that had the most hits also had the most misses -- works that you never hear."

Keep producing. Keep moving.

Thing I Definitely Should Have Known Earlier In Life

I recently found out that a pickle and a cucumber are the same thing. I had no idea. Yeah, laugh it up. Real fucking funny. Thankfully, I didn't have a strong opinion that pickles were definitely not cucumbers, so it wasn't hard for me to change my mind on this whole cucumber-pickle thing.

There's probably a life lesson here ("Look at how quickly you learn when you don't have strong opinions!"), but it's more likely that I should have just known what a pickle was.

Strong Opinion That I Am Unlikely To Change

Stay Out Of My DM's, Haters

Can I please say what we’ve all been thinking?

Most wedding speeches are unforgivably bad. 

In general, people are horrible at saying interesting or insightful things about other people in public.

I think many people assume that because they love somebody, they'll have something worthwhile to say about them. Unfortunately, some combination of the following is usually what happens:

  • They say something horribly generic, like “[bride] is the nicest person I know” or “[groom] is a great guy”

  • They tell a you-kind-of-had-to-be-there story that elicits nothing but nervous laughter, or silence

When you say generic things about a person, it makes me think that one of two things is true: a) you actually don't appreciate the person or b) the person actually is as generic and boring as your speech.

Clearly, though, nobody is going to give people feedback on wedding speeches ("hey man, here are seven things I didn't like about your toast...") so they probably never realize how bad they actually bombed.

For the love of (non-existent) God, if you're planning on speaking at a wedding in the next few decades, please actually have something to say and practice, practice, practice.

Genius Is Only Obvious In Hindsight


I don’t consume cannabis very often, but when I do I usually end up watching documentaries about Thomas Edison.

Which, as I write that, makes me think I should smoke weed more often.

Anyways, a historian in one documentary said something that was deceptively profound.

“Edison decided he was going to be about inventing. He was going to invent full-time.”

That was a new concept in Edison’s day? That blew my mind. Today, one of our most popular TV shows revolves around people pitching their inventions in the hopes of turning it into a successful business.

Obviously, people invented stuff in Edison’s day, but apparently he was one of the first people to do it as his main hustle, exclusively inventing and commercializing brand new technologies.

At the time, there wasn’t even really a mental model of what a “successful” inventor looked like. Edison had to figure that out.

Tragically, humans hate this sort of ambiguity.

When we think about our careers and the contributions we want to make to the world, we often lack Edison’s courage and prefer to just do the things we’ve seen work before. It’s easier to cut and paste from a few compelling role models, proven professions, or tried-and-true paths.

Sometimes, following the crowd works (the now-conventional wisdom “learn to code” probably isn’t bad advice in general). Sometimes, though, it’s tragic (are people still getting accounting majors?!).

Even if pursuing a “traditional” path works out financially, it’s not hard to accidentally sacrifice what is uniquely valuable about your perspective or personality in the process.

“The people who make Vice President at this bank are soulless, miserable creatures who frequently fill their comically-large penthouses with people they, deep down, despise. Therefore, it is imperative that I kill my personality and sense of humor as soon as possible. Because, money.”

That outcome feels as tragic as picking a dying career path. They both cost the world a unique contribution.

At some point, every compelling role model had to ignore the prevailing wisdom of their time and be the first person to do something.

They had to suck it up and deal with the uncertainty.

Their genius is only obvious in hindsight.

Our “normal” is just the world a few weirdos championed 50 years earlier.