Weinberg: VCs give bad hiring advice because executives manage them up
Winston Weinberg · Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings · Jan 19, 2026 · at 14:12
Winston Weinberg is the CEO of Harvey. He explains why venture investors excel at advising when to hire senior executives but often recommend the wrong candidates.
0:00 / 0:23exact quote · 23.2s
▶ Watch the full episode on YouTube → 720p mp4 · rendered on demand · StarZero watermark
“The thing that I think they've been wrong about is who to hire. And I think sometimes the problem that VCs have is they're managed up. Right? Like they don't actually see inside a lot of these businesses. They see the board meetings. Right? And so sometimes the person who like presents really well at all the board meetings or something like that, they think of as that's a really good executive.”
quote is from the automated transcript, cleaned for reading: filler sounds and stutters are removed, nothing is rephrased. names can be misheard (the analysis reads context, assessments check outside sources). how →
More from Winston Weinberg
Weinberg: AI won't replace junior lawyers, law firms will do more work
“I don't think so. I think we'll just get more work.”
Weinberg: Most enterprise customers do not know Sequoia or Andreessen Horowitz
“The vast majority of our customers don't know who Sequoia, A-sixteen, Z, or any of those people even are, right?”
Weinberg: EQT brand gives legal tech startups more credibility than Silicon Valley VCs
“A vast majority of VCs give you that brand, and what's actually interesting for us is, like, someone like EQT actually gives you that more than Silicon Valley because they're private equity, and, you know, a lot more lawyers know who that is, et cetera, right?”
Weinberg: Product iteration speed is the main threat to application AI
“I think just moving fast enough on product, like that, that is always, I think, the biggest existential threat for all the application layer companies. And it's not necessarily that, you know, Anthropic or OpenAI are, you know, tomorrow gonna put 50% of their …”
Weinberg: Consumer AI is plateauing because reasoning is already sufficient
“So I think that we're seeing a plateau in performance for consumer use cases. And the reason why I think this is like a misnomer or something that people actually shouldn't pay attention to is we don't need them to be better for consumer use cases. Like, I fee…”