“I spent every July rebuilding cost basis from scratch. Not anymore.”
Yes — a few lots over the years, mostly for big expenses. A car, a family trip, one lot to help with a property down payment. Never a large chunk at once. My general approach has been to hold as long as I can and sell only when there's a specific reason.
Morgan Stanley at Work for the actual shares, and a spreadsheet I built myself for the India side. Every July I'd manually look up the SBI TT rate for each of my 24 vest dates on the RBI website — 24 rows, 24 calculations. By year four I'd gotten it down to one Saturday. It still felt like a second job.
My CA sent a bill with a ₹15,000 line item — "complex foreign asset reconciliation." Two of my SBI TT rates were from the wrong dates. I'd used the notification date, not the actual settlement date. That's ₹15,000 to fix my own clerical errors. That was enough.
Hold most of it. I believe in the company, I'm still growing at Google, and the lots I have are accumulating LTCG eligibility. I'll probably sell selectively when something specific comes up — real estate eventually. I'm not in a hurry.
Moderate, honestly. I'm comfortable being concentrated in GOOGL because I understand the business — I work there. But I know that's not a great reason to hold 100% in one stock. I've been slowly thinking about diversifying after the LTCG window opens on older lots. I just haven't gotten there yet.