A few years back, I worked for a startup with a micromanaging CEO. 1-2 women in the office would typically be the focus of his ire. He’d nitpick their work to death, especially regarding design (logo sizing, different layout styles, backgrounds, etc). While he sometimes had a point, it was almost never an salient point. Most of these women reported to me, and he would rant about their incompetence and demand that I fire them.
(It is worth noting that this company had experiened a great deal of turnover in the years before I started, and most of departures were women).
Due to his Steve-Jobs-style criticisms, it was hard to get anything done when he was in town (vs out fundraising). He thought the women on my team were incompetent, but he didn’t think so of me (at first, anyway). However, our relationship degraded because I didn’t want to fire the members of my team at his (unreasonable, IMO) demand. I went from being calm and reasonable to increasingly angry, eventually telling him in person and via email that his behavior was directly and indirectly causing the company to fail, with phrasing that was not profane but certainly pulled no punches. In terms of my own culpability, I became too close & friendly with my team, and toward the end of my tenure would participate in unproductive venting sessions about the CEO’s behavior (which I regret; this is not proper behavior of an executive no matter how poorly the CEO behaves).
At some point his advisor, a local well-regarded & well-known female VC, agreed to do a session with the management team to resolve these issues. I thought, as did the other couple of C-level execs, that we were going to have a CEO-intervention – asking him to change his ways lest the company performance suffer. However, it turned into an intervention for *me* – his VC/advisor decided that I was the source of drama and chaos at the company, by acting “heroically” in my own mind to ostensibly defend my team against antagonism I had entirely imagined. She also (validly) called me out for having “threatened” to quit 2x (I really should have left after the first time – it was no threat and my sincere intention to leave, but I regretably let myself be talked into staying).
In the end, she encouraged me to stay but to “stop the drama.” I took it to heart – really believing that I was the problem – for a couple of weeks. However, the effect of her intervention wore off as I either 1) returned to my delusion of him being the problem or 2) returned to the clear perspective that he *was* the problem and I had never imagined it to begin with. I decided to quit and not let myself get talked out of it (though at that point, I doubt he would have tried). I sent the VC woman a note about my decision, thanked her for the session, but said “I think you will find that I was not the source of the problems, and that the drama will continue after my departure – but if anyone can help him correct course, it is you.” I left.
6-8 months later (IIRC) the CEO is removed from his leadership position. The company failed to flourish (for a few reasons, not least of which is the sheer difficulty of what it was trying to do) and will probably get parted out and sold for some minute fraction of the money invested in it.
2 years later, I am raising a round for my own startup. The first VC I talk to, a wise & awesome human (from what I can tell), ends up asking about me around town and talks to this VC/advisor woman. Through the (very direct) grapevine I learned that she has a poor opinion of me because of how I handled myself at that startup, and this lead to questions of my capabilities as a leader. I’m worried now that my “bad reputation” may be disqualifying. We have a tightknit VC community here, and plus I’m a female – and thus I suspect potential funders might be more inclined to ask her about me, more inclined to believe her words are unbiased, etc. I have prepared something to say if anyone asks me about this directly, which is essentially “I was trying to do the right thing, but I have some regrets” – because anything I express that could be construed as a grievance will not be well-received. I do sincerely have regrets – I wish I had been composed and emotionless, not angry, and had left the moment I realized that I could not change him. It was not my finest hour (though I am proud of standing up for my team at a time when it was not easy to do so).
In general, I suspect I’m getting a cold reception to the investment community. I am only in the beginning of my fundraising process, so it may turn around. But what can I do if it doesn’t turn around? Focus on VCs outside of this community, and hope that their due diligence doesn’t include contacting these people from my past?