Would you invest in a founder with a 20-year track record who recently committed a felony not related to ethics or fraud?

There’s a sucker in the room. Are you sure you know who it is?

I’m morally flexible on things others might now be comfortable with. Each investor will decide where they are on the spectrum.

Most funds have fiduciary responsibility so may not be able to.

I said the other week “I’m not smart enough to be a criminal”. I meant a ‘good criminal’.

If you believe the person will kick ass, then do you really care? So long as they can attract staff, do sales to close clients, raise money etc. The goal is an exit, right?

Just think long term. Will this person be able to scale to the opportunity and can you ever trust them?

Do you know what a lot of people commit felonies casually every day (jaywalking), they just don’t get caught. So there is a cast the first stone element when judging people.

I wouldn’t invest in a murderer as frankly, I argue a lot and I’m not interested in what might happen if there was a heated argument…

I only discriminate on intelligence and trust. You need to figure out what you are comfortable with and what you think other stakeholders will be.

I had the op to take investment from a smart dude who was a criminal.

My issue was I thought he was smarter than me so I would end up the sucker. Didn’t go there.

I know a startup where VCs found out the CTO was committed for wire fraud at 16. They still invested. He wasn’t super shady, he was just smart and did stupid shizzle in his past.

Out of principle, I would never invest in a rapist. There’s just grey lines for other things.

The reason law exists is to discourage people from breaking the law due to the concequences.

If you find yourself caught and convicted of a fellony, you still have options. They’re just a bit more limited.

Most investors are pretty straight-laced, at least in public. It pays to be too.

There is a lot of money to be made investing in naughty things like porn. 400m people a month watch PornHub, but do you think they will ever IPO?

The big funds have morality clauses.

I have a friend in the Valley who worked at a big fund. He confessed he angel invested in some sex startups. Few years later he stopped as it is just too hard to get exits.