Kyle Wiggs / Writing / Leadership

Leadership

The co-founder conversation everyone postpones

Four questions, all uncomfortable early and all catastrophic late. The discomfort does not decrease with time. The cost does increase.

Why they get postponed

Because at the start everyone is aligned, the work is exciting, and raising these feels like distrust.

That is exactly backwards. Raising them while everyone is aligned is the only time they can be discussed without a specific situation attached.

What happens if someone leaves

The most important and least discussed. Does their equity vest, over what period, what happens if they go at eighteen months.

Without vesting, a founder who leaves early keeps a share the remaining people spend the next decade earning for them. It is the most common serious founder dispute and it is entirely preventable.

Vesting is not distrust. It is the mechanism that lets you trust each other without betting the company on it.

Who decides what

Not job titles. Which decisions each person makes alone, which are joint, and what happens on genuine disagreement.

Consensus works until the first decision where consensus is impossible, and that is a bad moment to discover there is no mechanism.

What each of you wants from this

A large outcome in seven years, a durable business to run for twenty, or a job that is better than the alternative. All legitimate, all incompatible in important ways.

Founders assume alignment here more than anywhere else and are wrong more often than anywhere else.

What happens if it does not work

How you would wind it down, who owns what, and how you would want to treat each other.

Discussed at the start it is hypothetical. Discussed at the end it is a negotiation.

Write it down

With a lawyer. A conversation everyone remembers differently is worth roughly nothing when it matters.