Personal blog on early retirement, selling tradelines, and analytics projects. I write about what I learn as I am learning it.
This is part three of my series on rebuilding the daily fantasy lineup optimizer I started in Excel in 2012 (start here if you missed the first one). This post is about a small, clever trick I used in the spreadsheet for years to handle players who can fill more than one position — and why, when I rebuilt the tool, I deliberately threw it away.
This is the second post in my series about rebuilding the daily fantasy lineup optimizer I first wrote in Excel back in 2012 (the origin story is here). Before I get into the clever parts, I want to start with the simplest and most important idea: a fantasy lineup is just a knapsack problem wearing a baseball cap. Once you see that, everything the optimizer does makes sense.
Back in 2012 I got into daily fantasy baseball, and like a lot of people with an Operations Research degree and a little too much free time, I couldn’t just play. I had to model it. That turned into an Excel spreadsheet that picked my lineups for me, which a few years later turned into a small side business selling those spreadsheets on Fiverr, which then sat untouched in a folder for the better part of a decade. This summer I finally dragged it back out and rebuilt it as a free lineup optimizer that runs in your browser at mlb-lineup-optimizer.kindoflost.com. This is the story of how it got here, and the first post in a short series about the rebuild.
People email me a version of the same hopeful question: how do I convert my traditional IRA to a Roth without paying taxes? I get why they ask. A Roth conversion lands a tax bill in the same year, and nobody enjoys writing the IRS a check for moving their own money from one pocket to another. So let me give you the honest answer first, and then the part that actually helps — the move that gets you as close to “tax-free” as the law allows.
Continue reading “Convert a Traditional IRA to Roth Without Paying Taxes?”
I spent the last stretch building a tool that answers one question I get asked constantly in the FIRE world: how much of my traditional IRA should I convert to a Roth each year? Put another way: when does a Roth conversion make sense, and how much should you do? The tool runs a real optimization model, not a rule of thumb, and the interesting part is that once I started feeding it realistic numbers, the math kept repeating the same handful of lessons. Here they are, in plain English.
Quick disclaimer up front: I’m an operations-research guy, not your accountant. This is what the model showed me, not advice for your situation. Talk to a tax professional before you act on any of it.
Continue reading “When Does a Roth Conversion Make Sense? What the Math Says”