“Sell enough on day one to cover your actual life-changing liabilities and taxes, then let the rest ride. I've watched too many people get clever timing the market and end up with a concentrated bet they never chose to keep.”

“I would sell enough on day one to remove the risk of a single stock dominating my net worth, then keep the rest as a bet on compounding. Sequoia has long held post-IPO shares in winners because most of the value in companies like Google and LinkedIn came after the public offering, but I would not let that possibility leave my family's finances hostage to one company's next six months.”

“I'm not going to tell you a number or a rule. That's between you and your tax guy and your conscience.”

“I watched Greg Smith at Thinkific go public in 2021 and not sell a single share on the day. His VCs actually bought more. An IPO is liquidity, not an exit. If your vested shares already exceed five years of earnings, I'd sell enough on day one to lock in life-changing security and let the rest ride. Concentration is what built it; concentration is also what can take it away.”

“I would sell enough on day one to lock in real, life-changing money: pay off debt, cover taxes, and put a meaningful amount into diversified assets you can't lose if the stock craters. Keep the rest, but don't let a single company's fate decide your family's future.”

“I led Elastic through its IPO, and the mistake I saw too often was people treating their lockup shares like a scoreboard instead of money. I would sell enough on day one to cover the life-changing things: debt, a house, and a diversified nest egg you never have to think about again. Keep the rest, but only what you are genuinely willing to see cut in half the next morning.”

“I have sold after lockups and I have held. The only wrong answer is trying to time the top. Sell enough on day one that the rest is house money, then park that liquidity in QQQ and forget about it. I put 80% of my own liquidity there whenever I exit, at any price, because time in the market beats timing the market. Keep a concentrated bet only if you would still buy the company today at this valuation with cash.”

“I have been through multiple exits and the IPO lockup release, and the mistake I see repeatedly is people treating the first trading day as the decision point instead of having a plan already locked with a tax advisor and a 10b5-1.”

“I have not been through an IPO lockup myself, but I have watched founders treat a liquidity event as a scoreboard instead of a reset. I would sell enough on day one to erase any decision-making that depends on the stock staying up. For most people that means covering taxes, paying off debt, and setting aside a safety net in cash, then letting the rest ride with a clear head.”