“Convince Me” said the Investor. “No” said the Founder.

It’s in a founder’s natural disposition to want to convince people of their point of view. And while engaging substantively with those who disagree is often an excellent way to both stress test your assumptions and increase your ability to tell your story, figuring out when to stop and disengage is critical for your productivity and sanity. Especially during fundraising.

Earlier this summer an engaging and forward-thinking founder told me a story from her in-process seed fundraise. Operating in a technology market that most would consider nascent, she had encountered a variety of responses to her pitch. Spoiler alert, more than enough were positive and she soon closed an oversubscribed round, but of course she also encountered rejection. We talked a bit about what she’d learned from those conversations and then the founder confided her most useless investor meeting to me.

“We sat down to discuss my company and he basically said, ‘I don’t think your market is going to exist. Convince me.’” Her response? “I told him I didn’t want to work that hard, and wrapped up the meeting.”

You know what? She was right. With some additional context, it was clear this wasn’t going to be the right investor for her company. He had no experience or basis for his assertion, just wanted to test her and/or establish a position of power in the discussion. This wasn’t a thesis defense. This wasn’t 15 minutes she’d finally finagled with a respected CEO in her industry. This was a man who, despite agreeing to take the meeting, established within the first few minutes of their conversation that he wasn’t someone who was likely to end up on her cap table and even more importantly, probably someone she didn’t want there. And she respectfully but firmly made a judgment call to not throw good time, and good energy, away.

So maybe pause this afternoon and think about one employee, one customer, one investor who is not critical and the source of disproportionate stress for you. And say Bye Bye Bye….

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