Lessons From 100 Moontowers

Welcome to Moontower episode 100. I also picked up 80 new subs this week pushing the total over 1500. I started this weekly letter with the Dazed and Confused namesake March 2019.

I’m going to share a few bits about this little experiment in the hope that there might be a bit of inspiration or even lessons from my experience.


2 years ago I was always blowing up friends and family chats with links and commentary on random stuff. Yinh had been a few months into her podcast so she had already “put herself out there” and suggested I collect my ideas and send them to friends once a week. Since I was already feeling bad for RIP-ing friends’ WhatsApp notifications, I figured what the hell.

So I emailed 100 friends and asked if they would be cool receiving a weekly musing. About 45 people signed up.

The writing started mostly as me drawing connections between related links. The readership grew steadily but slowly but it was never my goal to reach a bunch of people. It was really to spark conversations. And it did. One of my favorite things about the letter is how it has put me in touch with the friends I miss out on because life gets in the way.

The letter was and remains a big time commitment. I harvest links and take notes as a life habit. I would do that even if there was no letter. But the letter specific time suck is about 6-8 hours per week with a long tail for letters that have taken 15 hours. I love and hate writing the way one hates and loves working out. It’s painful and hard but there’s some reps and PRs which make it all feel worth it. When you’re done you feel good but it’s less of an endorphin and more of relief. You earned a beer and music with lyrics.

I remember my buddy Khe telling me that 95% of letters fizzle out by the 20th issue and I remember being proud when I crossed that checkpoint. I promoted the letter on Twitter where I had basically no followers but every now and then someone with a following would get a hold of the letter an take a liking, and boost it. Both my Twitter and letter following started growing together.

This was where this Moontower experiment was starting to point me in a direction.

Writing As A Catalyst

When I would write about investing or options I would get more readers. And this is despite the fact that I don’t give tips or trade ideas. It was more the  meta or theoretical aspects of trading. So within 6 months, the letter that started as links evolved into “write what you know”. I always enjoyed the teaching aspects of my day job over the years so finding many eager learners online offered a fun challenge. Can I make technical finance ideas approachable?

Within a year of starting Moontower, I had the confidence to write about technical ideas. I added Money Angle to the format as a safe space to talk about wonkier finance topics. They were well received and spread through #fintwit and even amongst investors in both Yinh and my networks. It led to so much inbound encouragement and thank you’s that it fed on itself. I’ve joked before that my love language is compliments (“words of affirmation” is the scientific term). From one angle that makes me sound insecure. That’s not without a nugget of truth. I even keep an “encouragement” label in Gmail for all the feedback I get. It’s important and meaningful to me. I respond to every email I get. But being powered by compliments means the cost of my human capital is quite low. I write because it’s useful to others and I get a better understanding of things that I spend time thinking about anyway. Win-win. Compliments are a renewable energy. In fact, I think encouragement and gratitude are some of the most underutilized sources of fuel out there. Many people would work for less money if they believed what they were doing was special to others.

So if what I’m doing is useful it’s all of you that I have to thank for pulling it out of me. You were all helping me and one another without even knowing it.


I was warned that writing in public was risky. The internet is permanent. Cancel culture. Trolls. I take these warnings respectfully. But it’s not me to worry too much about that. I give “people the benefit of the doubt” to a fault. (Except brokers — we used to have a joke on the floor…”how do you know a broker’s lying? Their lips are moving.” If you are a broker reading this we’re cool don’t worry.) I live pretty outwardly. I think the benefits of living that way outweigh the times I get burned.

I expect my outwardness is a defining aspect of this letter. I still write it like I’m writing to 40 close friends. I talk about my family, deeply personal experiences (like when Max was in the hospital or when Zak was born), and personal views (like why you can’t say ‘deserve’ around me). I do this because I like hearing others think aloud. We are all a bit voyeuristic. I subscribe to others’ letters because I want to hear them think. And if I like how they break things down then I want to hear how they break down the things that happen in their lives. I’m probably not alone in feeling that way. So I write personally because I expect you’ll appreciate it too.

Plus if it falls flat, my kids will have their old man’s writing to look back on one day.

For Other’s Interested In Getting Started

If you were on the fence about writing a newsletter, I can offer these encouragements:

  • Finding topics is easy because writing generates more ideas.

    I started with a list of about 20 topics. Well, I’ve now written 100 letters with multiple topics in each one and my outstanding queue grows faster than I can write them. Also, you start to see the world from the lens of “other people might want to know about this” so experience just drops tons of ideas into your inbox.

  • Having no audience is actually good

    Small audience means low pressure. A small audience is also going to be supportive since they will be friends and family. You don’t want to feel like you are writing to an empty auditorium forever, but you should expect it to be like that for awhile. Expectations are everything. If you have low expectations than every bit of growth will be dopamine. And you don’t want to desensitize your receptivity to it because of high expectations. Writing is hard and those drips of dopamine might just be the bits that help you push through.

  • Writing is hard

    It just is. Don’t be discouraged. It’s hard for everyone. Even Seinfeld considers it torture. It’s also more time consuming than you expect.

  • It’s never been easier to start

    Substack. Twitter has partnered with Revue. I’m using Mailchimp. Don’t waste time overthinking the tech, the title, the logo, or anything else. You don’t need to buy the perfect sneakers before you go running. Just go outside and run. Action creates information. You can blindly trust me on that. Just start.

  • Ignore me

    Finally, most of you should ignore me. The opportunity cost of a minimum of 1 hour a day is high. You could have taken a course online, started a business, gotten in killer shape or just put more time in at the office. There’s so many uses of time that will all yield amazing benefits if done for 100 consecutive weeks. But if you are not especially happy with how you are using your time, maybe too much video games or Netflix, remember writing is a form of expression that recruits so much of the self without requiring you to leave the couch.

Thank you all for giving me the privilege of sharing to an actual audience.

One last thing. This past week I was reminded of a fun story that embodied our guiding principle of outwardness. It will be especially amusing to food fans or SF’ers. Mom, you’ll want to click on this too –> thread

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