I was approached by a recruiter for a founding Legal Counsel role at a cool AI startup. At first glance it was a real rocket-ship: just raised a Series B, growing headcount and ARR, and allegedly profitable. But there were some glaring red flags: The JD was looking for someone with 1-3 years’ experience (and paid accordingly). They said openly that applicants should be excited to work ~70 hours per week in person. Nobody in the company seems to be over 30.
I gently pointed out to the recruiter that the experience requirement seemed out of step with the level of responsibility required for a solo counsel role (and, of course, that the hours expectation precludes people with families). The recruiter seemed genuinely confused and curious as to why I thought 1-3 years of work experience was insufficient for this role. Not surprisingly, they didn’t invite me to interview.
Don’t get me wrong. I’m in my early 40s and twice before worked under CEOs who were younger than me and founded their companies in their 20s. In both cases, they had the good sense to surround themselves with remarkable professionals of all ages, and weren’t intimidated by hiring people with a longer career track record than them. I would never judge a founder as being too your or too old (or any other silly and irrelevant trait). But I have very little faith in founders who only hire people in their own image.
When founders hire employees in their own image.
I was approached by a recruiter for a founding Legal Counsel role at a cool AI startup. At first glance it was a real rocket-ship: just raised a Series B,…


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