A Burned-Out Castle

John Bonini
4 min readJan 20, 2025

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My Gmail inboxes reach zero a few times every year.

I am not yet at that point, but a federal holiday plus snowfall in NYC helps.

The benefit of subscribing to content with a long shelf life is that I don’t deal with emails from retailers or daily digests that quickly become obsolete or stale.

One newsletter directed me to a link from an old post from Nat Eliason, who wrote “40 Lessons from 30 Years” back in March 2023:

Beware of shadow careers. This idea comes from Steven Pressfield: “Sometimes, when we’re terrified of embracing our true calling, we’ll pursue a shadow calling instead. The shadow career is a metaphor for our real career. Its shape is similar, its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us.” See also: When The Money’s Just Too Damn Good.

The above is only one of the forty lessons, but I agree with most.

I mention this because I listened to Jim O’Shaughnessy’s Infinite Loops podcast episode with Sahil Bloom today.

They talk about work and life since Sahil has a new book coming out on February 4th (my mom’s birthday!):

In The 5 Types of Wealth, Sahil Bloom offers a transformative guide for redesigning your life around five types of wealth — Time Wealth, Social Wealth, Mental Wealth, Physical Wealth, and Financial Wealth — that will lead to a durable satisfaction and happiness you can build and maintain across the seasons of your life.

Whether you are a recent college graduate, mid-life warrior, or a retiree, this playbook will unlock new levels of freedom and fulfillment:

• Control over how you spend your time
• Depth of connection with those around you
• Clarity of purpose, presence, and decision making
• Improved health and vitality
• Simple pathways to financial independence

Part of the discussion mentioned a quote from Nikos Kazantzakis’s novel Zorba the Greek: “Leave nothing for death but a burned-out castle,” which I borrowed for the title of this post.

I am getting ready to read Sahil’s book next month, and one day earlier, I will also read Jim O’Shaughnessy’s new book, Two Thoughts.

I met Jim at a D.C. FinTech event a few years ago, and he was smart, funny, and gracious with a crowd that follows and loves him on Twitter (I won’t call it “X”).

For a long time, Jim would share two thoughts (memorable quotes) every day on Twitter, which were always inspiring or insightful.

Jim’s publisher, Infinite Books, shared a good David Foster Wallace quote last week:

If you spend enough time reading or writing, you find a voice, but you also find certain tastes. You find certain writers who when they write, it makes your own brain voice like a tuning fork, and you just resonate with them. And when that happens, reading those writers — not all of whom are modern… I mean, if you are willing to make allowances for the way English has changed, you can go way, way back with this — becomes a source of unbelievable joy. It’s like eating candy for the soul.

And I sometimes have a hard time understanding how people who don’t have that in their lives make it through the day.

Not every person who randomly posts on Reddit ($RDDT) has the mind of David Foster Wallace. Still, I spend more time on that platform than on most other apps, but not for financial and investing advice.

I initially scoffed at the Reddit IPO last March and thought its public trading life might be comparable to Twitter’s. But I was very wrong — so far.

More than tripling its stock price in less than a year is a good sign.

Reddit’s $30 billion valuation won’t soon approach Meta’s $1.5 trillion, but Reddit has accumulated valuable historical user data over almost twenty years.

From Reddit CEO Steve Huffman’s chat with Motley Fool Money in September:

The main difference in value to us between a logged in user and a logged out user is time spent of the logged in accounts. They just have more inventory. But we monetize logged out users as well. Now, there’s broadly two ways that we’ll target an ad. One is based on your explicitly express interests on Reddit. If you join the skiing sub Reddit, you’re likely to see outdoor ads, things like that. Then the other is the context of what you’re looking at. If you’re on a comments page, we call them post detail pages now. If you’re on one of those specific pages, that page is likely mentioning a company or companies by name and often specific products, and so we can target an ad based on the context as well. Big picture, we think targeting based on your explicit interests or the context of what you’re looking at, are I think healthy and explainable and not creepy ways of targeting ads. What we don’t do is we don’t target ads based on your personal information, your Internet browsing habits, anything like that. It’s really, what are you subscribed to? What are you into? What are you doing on Reddit, and what are you looking at right now? The math behind that targeting is much simpler than maybe what’s required elsewhere. That’s been working for us as well.

I may not immediately buy Reddit shares tomorrow, but I may be an owner by next month.

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