Many people in this community have investments heavily concentrated in employer or founder stock, facing the problem of diversification trade-offs: tax drag, risk vs return.
There's a number of retirement calculators out there, but I couldn't find one that helped with this, so I built a simulator to explore those trade‑offs. You plug in your position, timeline, and taxes, and it creates a monte carlo simulation of how different sell‑down schedules might have played out using historical data and gives you visualizations for outcomes at different diversification rates, an efficient frontier chart (return/risk), tax drag, etc.
It's a labor of love: private, no monetization, no BS. Just hoping it helps other folks. I had a lot of fun diving into it and trying hard to get the details right, but I'm not a PhD in financial simulation so hit me up if I got something wrong (or right!), happy to fix it or add meaningful improvements.
Many people in this community have investments heavily concentrated in employer or founder stock, facing the problem of diversification trade-offs: tax drag, risk vs return.
There's a number of retirement calculators out there, but I couldn't find one that helped with this, so I built a simulator to explore those trade‑offs. You plug in your position, timeline, and taxes, and it creates a monte carlo simulation of how different sell‑down schedules might have played out using historical data and gives you visualizations for outcomes at different diversification rates, an efficient frontier chart (return/risk), tax drag, etc.
It's a labor of love: private, no monetization, no BS. Just hoping it helps other folks. I had a lot of fun diving into it and trying hard to get the details right, but I'm not a PhD in financial simulation so hit me up if I got something wrong (or right!), happy to fix it or add meaningful improvements.