Catching Bad Guys with Math

Thoughts from a retired cybersecurity AI leader.

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  • Back to School!

    Back to School!

     

    I’ve decided that I don’t want to stop learning in retirement, so I’ve assigned myself an hour each day, five days a week to go to “school”. Here “school” can be anything as long as it’s some sort of learning for me; it could be watching a documentary, taking an online course, practicing guitar, etc. Continuous learning and adding some structure to my days is, I believe, important to a successful retirement!

    For my first school term, I’ve planned out a 7-week course to learn just enough Japanese and Korean to hopefully better survive and enjoy my upcoming trip to Tokyo, Osaka and Seoul this spring.

    My plan?

    First, I’m using Pimsleur language tapes (well, they’re audio files now and not tapes, but I can’t help myself!) on most days because I like their focus on conversational speaking instead of grammar, reading, and writing. Seven weeks is a very short amount of time, so it’s going to be important to just start speaking right away, and these Pimsleur courses do exactly that. I’m going to try to listen to them while taking a walk outside — but only when the weather is reasonable! It is so cold in Canada nowadays! — so I can get in some vitamin D as well. There’s one exception to the speech-only focus: I learned that the Korean alphabet is actually designed to be learned in a single day! So I’ve added a day to the curriculum to learn Hangul!

    Second, I’m (of course) going to use AI to monitor my progress, keep me on track, and also generate quizzes and flashcards that are customized and matched to my curriculum. Interestingly, AI can also have conversations with me, listen to my pronunciation and give me feedback. It’s remarkably good at this, and that I can customize the scenarios to practice conversations in is super powerful.

    I’ll report back on my progress and share what I learn about making this retirement school routine stick, as well as my language progress!

  • Mandarin Movie Finder: Coding with AI

    Mandarin Movie Finder: Coding with AI

    My dad likes to watch movies that have a Mandarin soundtrack, but Amazon Prime Videos has no “search by language” facility. Instead, you have to search on some other term (like “Jackie Chan”), manually click on each video to pull up the detail page, and see if what’s on Prime Video has a mandarin audio track. It’s super slow and painful.
     
    So yesterday I spent 3 hours doing my first AI-assisted major coding project. I wrote a “Mandarin Movie Finder” script in Python using Claude Code that would log into Prime Video, search on a term I enter, and then go through all the hits and add any unwatched Mandarin language video to my dad’s watchlist.
     
    It worked great, but it took a long time because as good as AI coding is supposed to be, it really required me to point it in the right direction multiple times. It’s particularly bad at debugging (and many, many times kept going down ratholes that were obvious to me) and building functions (AI doesn’t need to reuse code; it can just copy/paste the same 7 lines over and over again, so factoring out code just isn’t natural for it). I’m still not sure if it was faster than if I just coded it myself manually, but I have to say it was a lot of fun. It felt like a video game, where I’m trying to teach a junior who is super eager and super fast how to write a program. It was an interesting experiment for me.
  • QBRs for Life: Optimizing My Life, One Quarter at a Time

    QBRs for Life: Optimizing My Life, One Quarter at a Time

    Introduction

    As I write this, I am nearing the completion of the first three months of my retirement, July to September 2025. In the world of business and startups, this is, of course, the end of a quarter, and it is normal to review how things went during the past quarter, examine what went wrong and what went right, and adjust the plan for the next quarter. Often, these review and planning sessions were conducted in so-called “Quarterly Business Review” meetings, commonly abbreviated as “QBRs”.

    I’ve applied that same approach to optimizing my retirement life. I have a particular set of goals and strategies for my retirement, and to achieve those goals, it’s essential to review and course-correct as necessary, just like running a startup. So this past weekend, I spent a significant amount of time (most of Saturday and Sunday) going through my data and goals. Here, I found the use of AI tools like ChatGPT and Gemini super helpful.

    As I came out of the weekend, my approach to optimizing my life was sufficiently different — a nice way to say that I know I’m a weirdo! 😀 — that this might be interesting and helpful to others.

    So I’m posting my approach here.

    Process Overview

    Data: Data is everything, and I like to have all the data organized together on the computer. By storing this information in files, you can utilize tools such as spreadsheets and AI to analyze it. These files include storing your goals and strategies (which you should be writing down anyway, for other reasons) in .txt files, which are essential if you choose to use AI tools like ChatGPT or Gemini.

    Tools: Excel for basic analysis (I’m still most comfortable in Excel, although I’m trying to get more comfortable with Google Sheets and Numbers, with limited success), Soulver for more free-form calculations, and Google Gemini for AI-assisted analysis, brainstorming and discussions (I’m in the process of migrating from OpenAI’s ChatGPT to Google’s Gemini, which I’ve found more capable for my particular use cases). I take a lot of notes (using Vim, of course!), journal high-level plans and results (using DayOne), and manage my tasks (using Things).

    My QBR Process: Once I’ve got everything gathered together, I sit down in front of the computer and go through the various areas of my life. These areas include Health, Money, and Goals, which I’ll cover at a high level below.

    Health

    I’m going to focus on my progress here, so I won’t dive into specifics about what I’m doing to optimize my health. I am heavily influenced by Peter Attia’s science-based principles for optimizing longevity and healthspan, which he has well-documented in his book, “Outlive: Longer, Stronger, Healthier.” In summary, I have health goals in the pillars of diet, exercise, sleep, and mental health.

    In terms of data and tracking progress, I have PDFs of all my blood work, ultrasounds, and other medical records. I have written out my exercise routine, my family’s health history, my prescriptions and supplements, and even my current assessment of my mental health and social support system.

    I use Excel to track high-level trends, utilizing AI to extract data from unstructured documents whenever possible. (AI is really good at pulling out tables from blood work PDFs, for example, and charting them.) I upload all the documents to Gemini within a Gem I’ve created for my health (in ChatGPT, I used to do this using a custom GPT), along with instructions that reference Peter Attia’s approach and my high-level health goals. Then, I discuss my progress with the AI to analyze both the positive and negative aspects and identify areas for improvement.

    Money

    What is the goal of money? To optimize the financial section of my life, I am influenced by Bill Perkins’ excellent book, “Die with Zero.” I really resonated with this book when I read it a few years ago. I realize that not everyone is in the same privileged position as I am. However, as a recovering workaholic, I am deeply aware that without mindful planning, the money I have worked so hard to accumulate over my years of work will not be able to do as much good as it could. And that would really be unfortunate. The goal of money is to help you provide for and care for friends and family when they need help the most, and to pay for the experiences that you can enjoy while you can. Many of my financial goals are related to helping those I care about and traveling to specific places in the world, which I can do while I’m able.

    I have banking records and so-called “wealth plans” that have resulted from my meetings with retirement planners and accountants. I have also documented my financial goals, including things I want to buy, people I want to help, my significant recurring costs, places I want to travel to (and when), and my high-level budget (which I brainstorm in Soulver and can export as a PDF).

    I upload all this data to Gemini as a custom Gem, along with instructions related to my high-level retirement and goals around money. And, just like health, I have a discussion with AI about how things look. Am I spending too much, and will I start to encroach upon my self-declared safety buffer? Equally important, am I spending too little? Should I travel more or more aggressively, while I have the health to do so?

    Goals

    I find AI really good at brainstorming and providing “second opinions”. Having a separate session focused on high-level life goals, once a quarter, is incredibly useful to round everything out. I have specific goals around happiness, family, and even how I’d like to die. Going through these heavy but essential topics with an AI that is no longer sterile but is now empathetic, creative, and engaged — well, I find that helpful and even therapeutic.

    Summary

    As I engage in these AI conversations and brainstorm sessions, I inevitably come up with ideas, changes to my strategy, and tasks that I need to take action on. As these come up, I write them down. I update strategy documents, so I’ll have them ready to go for my next quarter’s QBR. I write down actions and concrete next steps or projects in my to-do app. I document high-level shifts and their reasoning in my journal, so I remember the rationale behind them.

    I hope someone finds this useful or interesting. At the very least, it helps exemplify that the data-driven approach I applied at work is something that is actually helping me with retirement. I want to succeed at retirement. Like life, I only get one shot at this! So I’m going to use all my experience here to optimize it to the fullest.

    Have an excellent Q4, everyone!