I sold about 10% total across five years, and even that smaller amount generated a large tax bill because of how much NVDA appreciated. Each time I thought about selling more, the price kept going up and I'd defer. The problem with a position that's done well is that selling feels like a mistake even when holding everything is the actual mistake.

Morgan Stanley, a spreadsheet, and a lot of watching the price. Honestly I wasn't managing them — I was observing them. Five years of quarterly vests with no real exit framework. My CA kept asking for the Schedule FA data and I kept building it manually. For a stock with this much appreciation, the INR cost basis calculations are significant.

I finally got serious about building an exit plan and I needed to understand exactly which lots had the lowest INR cost basis and which had the best LTCG profile. I couldn't do that cleanly in a spreadsheet with 20 lots at different prices. Rovia gave me the lot-level view I needed to actually make decisions.

Sell gradually over three to four years to spread the tax impact. I don't want to dump everything in one year and pay a massive LTCG bill. The plan is 25% a year, rotating proceeds into diversified index funds. I've already started — first tranche is done.

I was aggressively concentrated in NVDA by accident, not design. My actual risk tolerance is moderate. I want to build a portfolio I don't have to watch every day. The last five years taught me that a stock can go up a lot and you can still make poor decisions because you never had a plan.