Workshop: Taking Stock

Hi all,

This past week, I sorted through the boxes that had arrived from Germany. Among the books and winter clothes was a painting that had not been on a wall since maybe 2013. And that’s because, frankly, it’s a bit intense.

It is up on the wall now though and as they said in the Big Lebowski, “it really ties the room together.” It was made by an artist friend and is based on the movie American Psycho. Thankfully I am long past the point when I wanted to be the slick banker in an expensive suit. However, I still appreciate the book and movie’s message, and the closing monologue always stuck with me:

“My pain is constant and sharp, and I do not hope for a better world for anyone. In fact, I want my pain to be inflicted on others. I want no one to escape. But even after admitting this, there is no catharsis; my punishment continues to elude me, and I gain no deeper knowledge of myself. No new knowledge can be extracted from my telling. This confession has meant nothing.”

Bateman is trapped in a world of desire for money and status, a world devoid of meaning and morality. I find this pain relatable. Or perhaps it’s just the headache I have after switching from coffee to green tea.🤔

After more than a year of writing this substack, it felt like a good time to take stock and talk about what feels like a conundrum. A few months ago, I wrote that I enjoyed writing because it forced me to be honest. It is uncomfortable to admit this, but I am not yet happy at all with what I created.

On the one hand, it has been a rewarding journey. I enjoy the research and writing process and I think at least few of the scale models of people and their journeys have come out well. I am deeply grateful to all of you who subscribe. One of my favorite activities has been to engage with all of you, to answer questions, and chew on your feedback.

However, I also find myself in a stretch of no man’s land. I’ve found some traction, but not nearly enough to make a living. Yet. And it’s not obvious whether it just takes more time, whether I need better product market fit (or perhaps: personality audience fit) or whether the TAM I write for is just too small.

Advice for content creators often boils down to this formula: find a unique or authentic angle on a topic you are passionate about, be interesting or valuable (better yet: both), and publish frequently and consistently. If you offer a premium product, tell people exactly what they are getting. Make it a compelling value proposition. Lastly, spend as much time marketing as you do creating. Well, I’ve been authentic. The rest I’m not so sure about.

I’ve struggled to define what exactly this is and am still playing around with the name, working on a new logo, drafting a new about page. The snake is still shedding its skin. Sometimes it feels like a simple mission: learn from legendary investors and entrepreneurs. Curate a faculty of teachers, dead and alive. How did they do it? But is that interesting and valuable enough to a large enough group of people?

As to frequency and consistency, Ira Glass of This American Life once said:

“Nobody tells this to people who are beginners, and I really wish somebody had told this to me. All of us who do creative work, we get into it because we have good taste. But it's like there is this gap. For the first couple years that you're making stuff, what you're making isn't so good. It’s not that great. It’s trying to be good, it has ambition to be good, but it’s not that good.

But your taste, the thing that got you into the game, is still killer. And your taste is good enough that you can tell that what you're making is kind of a disappointment to you. A lot of people never get past that phase. They quit.

Everybody I know who does interesting, creative work they went through years where they had really good taste and they could tell that what they were making wasn't as good as they wanted it to be. They knew it fell short. Everybody goes through that.

And if you are just starting out or if you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline so that every week or every month you know you're going to finish one story. It is only by going through a volume of work that you're going to catch up and close that gap. And the work you're making will be as good as your ambitions.

I took longer to figure out how to do this than anyone I’ve ever met. It takes awhile. It’s gonna take you a while. It’s normal to take a while. You just have to fight your way through that.”

To date, I have resisted a consistent and more frequent publishing schedule. While I set myself deadlines, I often blow right through them. Mostly because I feel that the work is not ready, not good enough. A hard deadline would force me to be more disciplined and incentivize shorter pieces. That said, with the draining moves and heartbreak out of the way, I know that I can do better.

Which leads me to the length of my pieces. Last week, I wrote about Floyd Odlum which turned from a brief narrative into an investigation to separate fact from fiction. I unexpectedly spent days digging into a draft biography, talking to its author, and re-writing the piece. I’m glad I did it because regurgitating an incorrect story would have been a complete waste. But I came away wondering if this was a commercially viable approach.

Premium vs. free content is another tension I wonder about. Once the most interesting content disappears behind a paywall, overall growth slows down. Another option is to keep deep dives free and offer premium subscribers access to more personal writing. However, the latter provides less incentive to sign up and might be more appropriate for a lower price point. It’s a catch-22 for a smaller newsletter.

Which brings me to the final lever: pricing. I originally viewed the newsletter through as finance/investment content. But since I’m not writing actionable investment or market commentary, I wonder if I overpriced it.

All of this is a long-winded way of saying that I’m re-thinking how to “build something people want,” to use Paul Graham’s words. I want to commit to a weekly profile or story and a personal workshop note such a this one. But I worry whether I will be able to keep up the pace. Finally, I want to add more conversations, possibly in a podcast/transcript format. I might reach out to all of you current premium subscribers to give you a chance to comment.

At the end of the day, I’m still just looking for my place in the world. To do something that I’m good at, that I can be proud of, that people find valuable. Ideally, I want to follow my curiosity and write and create. But sometimes I wonder how close I am to the painting lurking behind me, silently screaming in fear that these confessions do indeed mean nothing.


The Alter Ego Effect by Todd Herman. This one is firmly in the self-help category and might not be for everyone. The author, a coach to athletes and entrepreneurs, highlights the power of finding an alter ego: a character whose qualities you can channel in challenging moments. Examples abound among entertainers and athletes. Full disclosure: I enjoyed the book but have not found an alter ego yet. I could use both a focused go-getter/hustler and a captivating, funny storyteller. Anyway, check out my thread and this podcast if you’re interested in the idea.

I’m currently reading Damsel in Distressed by Dominique Mielle, a female partner at Canyon Partners, a distressed credit hedge fund part of the Milken/Drexel diaspora. I plan on recording a conversation with Dominique to talk about distressed investing from the telecom burst to today.

Other reading

Finding an edge by pursuing markets others shy away from: Ramzi Musallam and Veritas Capital, a private equity firm focused on government-dominated markets (defense, healthcare, cybersecurity). The story also highlights a point of fragility at smaller private equity shops: when Veritas’s founder died, Musallam had to scramble and convince investors not to trigger the key man provision that allowed them to wind down the funds. As it turned out, Musallam used that crucial moment to not only rescue the firm but set the conditions to make a fortune.

Circle of Incompetence or the dangers of investing as an industry insider:

“I have been a computer programmer for 30 years now. I worked at software companies for about half of that time. I have a Ph.D. in computer science, and I teach computer science at a university. If there is one area that I have expertise in, it is software. … However, my track record of investing in software companies is absolutely terrible. …

My software background made me unreasonable confident that these products would not succeed and that, if they did, they would lose out to competition. An investor without that knowledge would have been open to the possibility that their growth could continue for years to come, which is what in fact happened.


I wrote a thread about EssilorLuxottica, the French-Italian company that has quietly grown to dominate global eyewear. It’s pretty incredible how Leonardo Del Vecchio, a a penniless Italian toolmaker, started out manufacturing parts for others and ended up with a vertically-integrated global player that squeezes its competitors and owns brands ranging from Ray Ban to Oakley and from LensCrafters to Sunglass Hut.

The story of Berkshire’s Ajit Jain:

A fateful negotiation with Steve Jobs:

Something for the eyes: