Kind-of-Lost

From Daily Fantasy to Fiverr to a Free Lineup Optimizer

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.

Timeline from 2012 daily fantasy to 2016 Fiverr tools to a 2026 free lineup optimizer

Convert a Traditional IRA to Roth Without Paying Taxes?

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?”

When Does a Roth Conversion Make Sense? What the Math Says

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.

Building a Roth Conversion Optimizer: Lessons Learned

This is the third model I’ve pulled out of a spreadsheet and rebuilt as a web app, after the staff scheduler and the vehicle router. Going in, I assumed the optimization would be the hard part. It wasn’t. The solver finished in under a second every single time. The hard part was trusting what it told me — and the lessons that came out of that are the ones I keep coming back to.

Here’s what building a Roth conversion optimizer actually taught me. Not about Roth conversions — that’s a separate post — but about the craft of turning a twenty-year-old model into something other people can trust.

Free Roth Conversion Software (Coming Soon)

This is the part of the series I’m most excited about: turning my spreadsheet into free, online Roth conversion software — really an optimizer — that you can run on your own numbers, without owning Excel or knowing what a solver is.