Stock Vesting: Why Founders Should Vest Their Own Shares
Founders often skip vesting because "we own the company." Big mistake. Vesting protects you from co-founder departures, prepares you for fundraising, and is expected by investors. Here's how it works.
Standard Vesting Structure
- 4-year vesting: Shares vest over 4 years
- 1-year cliff: First 25% vests after 1 year
- Monthly after cliff: Remaining shares vest monthly
- Unvested shares: Return to company if you leave
Why Founders Should Vest
1. Co-founder Protection
What happens if your co-founder quits after 6 months? Without vesting, they keep all their shares. With vesting, they keep nothing (cliff not reached). The company can reissue those shares to a replacement.
2. Investor Expectations
Investors require founder vesting. If you don't have it, they'll impose it at funding—and the clock starts fresh. Better to start vesting at incorporation.
3. Negotiating Leverage
If you're already vested 2 years when raising, you have more leverage than starting from zero.
The 83(b) Election
When you receive restricted stock (vesting), you can elect under Section 83(b) to pay taxes NOW on the current value rather than when shares vest. For founders at incorporation, current value = almost nothing.
Without 83(b):
You pay income tax on share value at each vesting date. Company grows, shares become valuable, you owe income tax on the full value.
With 83(b):
You pay income tax on share value at grant (near zero). Later, you only pay capital gains on the increase. Much cheaper.
Acceleration
Some vesting includes acceleration provisions:
- Single-trigger: Accelerates on company sale
- Double-trigger: Accelerates on sale + termination
- Partial acceleration: Usually 6-12 months
Common Mistakes
- Not vesting founder shares (leaves you exposed)
- Missing 83(b) deadline (30 days, no exceptions)
- Not documenting vesting properly
- Starting fresh vesting at each funding round
We Set This Up Correctly
Proper vesting from day one saves headaches later. We handle the paperwork, 83(b) filings, and cap table setup.