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How I Think About Insurance Products

Following up on my financial directives post, here are some of my thoughts about insurance. Nearly everyone has to purchase multiple insurance policies. It’s a constant cost you’ll have your entire financial life. It’s worth spending some time optimizing. Friends and family have asked me about this multiple times, so I’ve slowly compiled my notes for them. Here they are! Don’t Prepay, Self-Insure Instead I like to think of insurance as something you most likely never have to use. If you expect to use insurance, you’ll pay for it in increased premiums and the insurance companies will come out ahead. Then, it’s not really insurance, it’s prepayment for services you are going to use…

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Financial Directives for a New Graduate

Writing creates clarity, and defining directives for various areas of your life is an interesting exercise. I first ran into this idea via Derek Sivers: "It’s just a succinct and powerful way to communicate an idea. Focus on the action." I’ve tried distilling my personal investing principles as a series of directives. My siblings and other younger people I know also ask for my financial advice. This post is partly an effort to make it easy to share my thinking with others when it comes up so I don’t need to repeat myself. Obviously, I’m not a financial advisor, lawyer, CPA, etc. I’ve simply written down my personal opinions…

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Downloading Fidelity Charitable & Cigna Health Records

Similar to my post about Amazon Photos and Wealthfront data extraction, here’s another set of scripts to download data from sites which have terrible interfaces. You can use both of these scripts by opening up the developer console and copy/pasting/executing them. Hopefully it saves someone some time! Download All Cigna Medical Claim PDFs This script will download all medical claim PDFs on Cigna over the last year. First, navigate to the claims summary page. Then set the filter to: view all, last year, for all people. Now execute this script: Here’s more explanation on why this trick works…

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Aggregating Data by Month in Google Sheets

Certain operations that are easy in SQL are hard in google sheets / excel. I ran into one of these: I had a simple problem: I had some time series data (dividend payouts from a financial institution) and I wanted to aggregate the data by month. In SQL, this is a simple GROUP BY, in sheets it’s not that easy. Create a separate sheet to aggregate data, then group Filter based on the type of transaction Look at each date and normalize it to the last day of the month =ARRAYFORMULA(EOMONTH(B:B, 0)) (this is now column E) Get a list of unique months (i.e…

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Download a CSV of Wealthfront Financial Activity

I use Wealthfront for a portion of my investments. I recently was trying to get a CSV of all my dividends, fees, etc this year and there’s not a way to do this! If you navigate to your activity (homepage > investment account > see recent activity) you can at least generate a CSV from the information on-screen (which does not include your gains/losses from the direct indexing) and copy/paste this into your web console, your browser will spit out a CSV. This is highly tied to the current (as of this writing) Wealthfront HTML structure, so you’ll probably have to ask ChatGPT to fix this in some number of months…

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Why the Right Premium Services are Always Cheaper

By nature, I’m frugal. I love getting a great deal, and getting the most of out of my purchases. When I was fifteen I got a new MacBook Pro for free by working those “get a free MacBook pro” ponzi schemes online: my obsession with a great deal started early. I’ve learned that it’s often worth paying for premium services when your time is at stake. Not only your current time, but time that a premium service could possibly save in the future. Opportunity cost is a real thing: it’s important to consider what you can’t do or time that could be possibly spent on fixing a future problem with the service or product. Here are a couple of failures from recent memory: Low Cost HSAs…

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