Selling · Stage 1 of 5
Deciding Whether to Sell
The questions worth answering before you start looking for a buyer at all.
A secondary sale is usually irreversible — once your shares transfer, you're out of any further upside (or downside) on the portion you sold. That's obvious in theory but easy to underweight when a buyer's offer is sitting in front of you and the cash feels concrete while the future upside doesn't.
The strongest reasons to sell tend to be about your own liquidity and diversification, not a view on the company. Needing cash for a real expense, wanting to de-risk a position that's become an outsized share of your net worth, or simply wanting to lock in a win are all legitimate — "I think the company is about to struggle" is a different, harder conversation with different disclosure implications.
Checklist for this stage
- Write down the actual reason you're considering a sale — liquidity need, diversification, or a view on the company's prospects. This shapes how much of your stake makes sense to sell (see structuring a partial sale).
- Estimate what a full sale versus a partial sale would net you after any expected discount, and whether that changes your answer.
- Check whether you're holding vested shares, unvested shares, or an unconverted SAFE/note — this determines which playbook stages and mechanics pages apply to you.
- Consider your relationship with the company and founders — a sale process, even a successful one, is visible to them and worth thinking about in that light.
Common pitfalls
- Deciding to sell reactively, right after a piece of bad or good news, rather than against your own financial plan.
- Not checking your paperwork before deciding — some agreements restrict sales for a period, or require conditions you'd want to know about before setting expectations.
- Underestimating how long the process takes (see closing and after) and needing the cash sooner than a realistic timeline allows.