Selling startup shares

Stuck with startup shares you can't sell? Here's what you can actually do

You left a startup after years, you're holding a chunk of shares, you're worried the company might not make it — and no investor seems interested. It feels stuck. It's usually less stuck than it looks. Here's the playbook.

This is one of the most common — and most stressful — positions a shareholder can be in: you've moved on, your equity is illiquid, and you can see risk on the horizon. The instinct is to feel trapped. In reality there's a clear sequence of moves, and most people simply haven't worked through it.

Step 1 — Know exactly what you hold and what the paperwork allows

Confirm whether you own shares outright or still hold options to exercise, how much is vested, and — critically — what your shareholder or operating agreement says about transfers: any right of first refusal (ROFR), board approval, or restrictions on who can buy. This defines the path everything else has to follow.

Step 2 — Offer to the obvious buyers first

Go to the company and the existing shareholders before anyone else. They may buy to consolidate — and because a ROFR usually means you have to offer them first anyway. If cash is tight, propose flexible terms: a sale paid in instalments with interest can work where a lump sum won't.

Step 3 — Use an upcoming funding round as your window (and your leverage)

If a raise is coming, that's your best opening. Tell the founders early that you intend to sell your vested shares and you're open to a sensible discount — framed as the easiest path for everyone. If they decline, you can (politely) approach the incoming investor: a departing shareholder willing to sell at a discount is often attractive, and founder-friendly investors will nudge the founders to sort it out rather than let it complicate the round. A seller setting a low price right before a raise is exactly what founders want to avoid — which is why this works.

Step 4 — If insiders pass, find a private buyer

When the company, the shareholders and the round all pass, the remaining route is a private individual investor who wants access — reached through a discreet introduction rather than a public listing. This is precisely the situation we're built for.

Two honest realities

• Expect a discount, and disclose. A struggling company means a steeper discount, and you must be honest about material problems — a hidden risk that surfaces later is far worse than a lower price now.
• Know when to stop. If you'd have to pay a large sum to exercise options in a company you no longer believe in, think hard before doing it. Sometimes the right move is to sell what you can, or to ask the founders to cover the exercise cost as part of your exit — and then move on.

Read next

• Who buys private startup shares — and how to actually sell yours
• Can an ex-employee sell startup shares?
• What discount is fair when you sell startup shares?

Further reading

General, independent references on how private-company shares and options work. We're not affiliated with any of them.

• Carta — cap tables, secondaries and valuation explainers
• Cooley GO — startup legal explainers, including rights of first refusal
• Forge Global and EquityZen — secondary marketplaces (larger, later-stage deals)
• Ledgy and Index Ventures OptionPlan — European equity & ESOP references

General information only — not financial, tax or legal advice. Every situation is different; check your own share and option agreements and take professional advice before selling. PrivateTechShares makes introductions only: it is not a broker, does not hold funds, and does not execute or advise on transactions.