[hellcow]

This is what’s typically done for founders—it’s called reverse vesting where the company gradually loses the right to repurchase them over time. Generally this is done when the company is new, pre-409a.

There’s nice tax advantages to this approach if you make an 83b election since the shares start counting toward long-term capital gains immediately.

[lbotos]

Thanks! That does make a lot of sense for founders, but OP mentioned "the company sold him shares" which leads me to some sort of weird pseudo options thing. Hoping they can clear that up so I can understand more.

Reverse vesting seems way more straightforward: you sign, you get equity immediately, company can take back any at agreed upon price at whatever intervals defined in the contract.

[ska]

Right, and it avoids some tax issues later as you have owned and held them since you started (jurisdiction dependent).

Reverse vesting is pretty common for founding employees, or near then, also, ime. The only problem is if the share value isn’t justifiable very low, it can be too expensive.

The moment you raise any significant amount , the implied valuation may make this impractical.