What isn’t going well

One of my favorite questions to ask founders is: “What isn’t going well at the moment?”

Whenever I meet with founders, they always love talking about the good stuff: The milestones they’re going to hit, the new customers they’ve signed, and the accomplishments of their team. But, they won’t spend too much time talking about what isn’t working… Not unless you ask them.

If a founder trusts you, they’ll freely share the good, the bad, and the ugly. But, it takes time and work to build that trust. Investing is as much a game of relationships as it is a game of capital deployment.

My advice to investors: The more transparent you are with a founder, the more transparent they are with you.

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