I've made > 100 pre-seed investments and the #1 cause failure in the first 3 years is founders quitting because of unresolved cofounder conflict. The first time I saw an obviously valuable, fast-growing company blown up because the founders couldn't agree on a $5000 travel expense I was astounded. Now it's something I've grown to expect - just one more risk to be managed.
To try and mitigate this my #1 question each time I meet with the founders I invest in is "how's your relationship with your cofounder(s) going?". If the answer to this question is anything less "fantastic!" we have a long conversation about why, before we talk about anything else.
A low cadence of communication between founders is also correlated with higher failure rates, so another fun question is "when was the last time you spoke with your cofounder?". Again I've stopped being surprised by the amount of founders that answer with "last week/month", which again needs to spark a conversation about why.
To try and mitigate this my #1 question each time I meet with the founders I invest in is "how's your relationship with your cofounder(s) going?". If the answer to this question is anything less "fantastic!" we have a long conversation about why, before we talk about anything else.
A low cadence of communication between founders is also correlated with higher failure rates, so another fun question is "when was the last time you spoke with your cofounder?". Again I've stopped being surprised by the amount of founders that answer with "last week/month", which again needs to spark a conversation about why.