What are things to be aware of with a co-founder who has sold a company before and has money?
At least in SaaS, it cuts two ways:
- Second time founders are delusional about how hard it is to achieve product-market fit. It isn’t >any< easier the second time. They think it is. It isn’t, just because you’ve done it before. This is the “no fail” mentality you are touching on. It’s common. And it’s wrong.
- Second-time founders scale much more rapidly once they have product-market fit. They know the VPs to hire — and they get it done. They hire them in advance, not in arrears. They know how to raise the capital. They know how to manage customers and prospects. They scale much more effectively, if not efficiently. Because they don’t waste 1–3 years hiring VPs one after another, and struggling to raise enough money. They skip past all that. They run the whole playbook, in parallel. Yes, and because of that, they sometimes run the company into the ground if they overspend. But they their build the team far, far faster and effectively (and expensively).
So you are taking more of a leap of faith here pre-product market fit with a second time founder, in some ways.
But really, both types of founders do very well.
Pick the environment that inspires you more.