A few weeks ago, I spent 45 minutes with a Venture Capitalist I’d never met before. The meeting started with the usual feeling-each-other-out type of chatter: shared contacts…recent travels…the weather. With the effortlessness only possible of “meeting professionals” we transitioned to business. First, an overview of their fund strategy (fin tech), investment stage (seed/A) and capital structure (a few funds, $100M); then, seamlessly, to my current venture. We talked high-level thesis. I demo’d our product. There was a rhythm to our conversation. We had chemistry. We were warm and comfortable; jamming. Then he leaned forward, arms crossed on the table. He paused and peered out over his glasses — and dropped this gem: “Want to know the trouble with this industry? All venture capitalists are dicks. We have the money and strong opinions. But know what’s even worse than that? All entrepreneurs. They suck.” His accent was thick, and it took me a moment to process. In writing it seems obvious. But in person I was more reflective of the tear-down of the occupations than the clear association of the insults. He had already moved on, but realizing maybe I hadn’t connected the dots, he backtracked and took it for a second spin: “Seriously, we’re all dicks. But entrepreneurs… then, the pause…for emphasis… They suck,” The rest of the meeting was as you’d expect. We continued our discussion on the business and their fund, and whether there was an opportunity to create value together. But all that was a blur. It was all irrelevant to the crushing weight of that brief interaction: In an era of # , was a line crossed, and if so which one? a dick-sucking joke between two guys in a closed meeting. No women involved or mentioned. But…where 5 years ago this might have been shrugged off as harmless locker-room talk between bros, it is now heavy with meaning. Has my brain been rewired? Are my eyes now more fully opened? metoo Exhibit 1: In a somewhat associated vein, the VC-to-Entrepreneur power dynamic continues to be woefully imbalanced. We may have made some strides within gender boundaries (I’m pretty sure this particular VC would not have made that joke to a female ), but not so much as it relates to the golden rule (you know: those with the gold…rule). More pointedly, if I’d made an attempt at that statement, the results would likely have been, well…career-limiting. entrepreneur I left the meeting with a handshake and a smile and equal promises that we’ll continue the dialogue. I tried to forget it ever happened. It was, after all, just words in a private room. But, weeks later, I still find myself recounting the story to others. It turns out it was one of the most remarkable moments in a trip full of remarkable moments. I’m left wondering exactly how I should feel. If anything at all.