Operator

“Hiring operators is really difficult in particular, because their networks tilt more senior.”

“When an operator approaches a mountain in his path, his immediate thought is like, how do I scale it or tunnel through it or walk around it? But the presence of the mountain is an immediate challenge that an operator's mind starts spinning on how to solve that…”

“Being a board member for somebody who's been an operator, the hardest thing to do is to realize that you're not in charge anymore.”

“I mean, I would say that this is the biggest difference between a venture capitalist and an operator. You have to figure out how to spend the most amount of time with the companies that need you least, and the least amount of time with companies that need you …”

“If you're an operator at an interesting, you know, hot tech company, it's fairly easy to become a scout for a VC fund.”

“That operators don't make good VCs. That's what I believe. I think it's really tough to have two CEOs in the boardroom. I think CEOs, when things work well for them, they're so used to repeating that, and sometimes it can work for another founder, but it's oft…”

“When you're a board member, you're asked to approve Or advise on the basis of having about 10% of the data you're used to having as an operator.”

“The other hump comes around two years in where most people after, you know, long operating careers, it's kind of a relief not to have to like drive and make decisions every day and be in that machine. But after a couple of years for a lot of people, that charm…”

“The two spots are kind of six months in and two years in. At the six month in mark, it's kind of, what am I doing exactly? Especially for a lot of people that come into venture, they show up for their first Monday or whatever, and they literally have nothing t…”

“The operator is excellent at scaling teams, driving cross-org alignment, and unblocking execution. And the operator superpower is communication. On the other hand, one of their challenges is actually original product insight.”

“It is nearly impossible for an operator to solely or mainly bring your product to product market fit. Now, it can happen, but it's extremely rare, and you should not bank on it.”

“I think the biggest mistake operators make when they give advice to founders is it's purely out of the lens of their experience in the environment and the circumstances with the tools and the capabilities that they had available to them. All those macro things…”

“I think the biggest mistake operators make when they give advice to founders is it's purely out of the lens of their experience in the environment and the circumstances with the tools and the capabilities that they had available to them. And all those macro th…”

“You're a spectacular investor of half your companies create, you know, create value, which means half your companies don't create value, and that hit rate If you're batting 500 as an operator, you're an ex-operator.”

“To be a good operator, you have to really stay on one thing with a kind of a singular focus for a prolonged period of time, and you also have to deal a lot with people, and I'm not really a people person at the end of the day.”

“And I think what's actually interesting is there's some operators that are very good at their operating job that I think would be worse founders than some bad operators. Right. And I've like found this. So let me explain that a little bit further. There are pe…”

“Pretty early on, you've got to also go and balance the board of investors with operators, because sometimes the conversation can become really very financial. It becomes very investor centric as a board conversation versus company centric. And a board is reall…”

“I think it would be better and more interesting if it were because I think that most of the advice that I've gotten the most out of is from existing founders or former founders or operators. Like they're the ones that have lived in those shoes. They're the one…”

“That's part of the reason why I think that operators are not necessarily the best investors.”

“The more important of the two for any success, like getting from zero to one is the operator. But then I think the ceiling of your possible success is a function of the conceptual thinker.”