I did a secondary sale when Stripe offered a tender opportunity before the listing. It was my first experience selling equity and the tax treatment was different from what I expected — the timeline and cost basis were not straightforward for that kind of transaction. I've held everything since.

The first two years the equity was on Carta — private company share tracking. When the listing happened, everything moved to Morgan Stanley. The transition created a lot history with two different platforms, different cost basis calculations, and a Schedule FA that my CA said was one of the most complex he'd seen that year.

My CA's honest assessment after the first post-listing ITR: "You need a proper system for this." He walked me through what Rovia does and why it would solve the specific problems in my situation — the multi-platform history, the INR cost basis at pre-listing grant prices, the LTCG window tracking on lots with unusual acquisition dates.

Hold for now. I joined Stripe because I believe in where it's going. I'm not selling to diversify yet — I want to see how the next two to three years play out. When I do start selling, I want to do it systematically with full visibility on the tax implications of each lot.

Aggressive. I joined a pre-IPO company and concentrated my compensation in it for four years. That tells you something about my risk tolerance. I'm comfortable with uncertainty. What I'm not comfortable with is administrative chaos — I want the compliance side handled precisely even when the investment side involves real risk.