
The Serial Founder Advantage, Myth-Tested Against What the Record Shows
Kenji WatanabeRepeat founders raise money more easily and hire faster — but the same experience imports habits that sink second companies.
Profiles of the people running technology companies, built around specific decisions.

Repeat founders raise money more easily and hire faster — but the same experience imports habits that sink second companies.

A SAFE is a deferred conversion instrument that turns into equity at your next priced round — and the conversion discount or cap, not the check size, decides how much of the company the investor ends up holding.

Under the SEC's Rule 506(b), a startup can raise an unlimited amount from an unlimited number of accredited investors plus up to 35 non-accredited ones, according to the agency — but only by skipping public solicitation entirely.

Co-founder conflict is a leading startup killer, and the postmortems agree it is preventable — not by avoiding disagreement, but by writing the divorce terms while everyone still likes each other.

Angels bet on you and VCs bet on the machine — the two money types differ in check size, patience, and what happens when things go wrong, and the cap table mix decides your worst day.

Joining a startup as a late co-founder or founding executive is the highest-leverage equity negotiation of a career — and the value sits in terms nobody volunteers: vesting, strike, preferences, and information rights.