Casey Winters: recommendation

Transcript context

…Any advice for either as a employee at a company with a founder like that or leader, of just how to push back and help the founder understand, "Maybe you should let go and trust people to make decisions"? I think the first thing is you have to understand that it's their company, not yours, and the founders have impossible jobs. They're not going to scale perfectly with the needs of the company. It's just something's going to be off. It may be because there's a whole lot of hubris by being the one of a thousand startups that made it, or they just have personal styles, but they can run the company any way they want. I think it's sometimes surprising when founders actually want to run things suboptimally. I think we've seen examples where founders just want to build cool shit versus focusing on what customers want, or they're too obsessed with the design. They're always rebranding, redesigning things in ways that confuse customers. Of course, that's going to happen and those are some of the worst cases. I think if you do state your point, you've actually built up the expertise, you're confident and you are refuted for whatever reasons, you have to find ways to be contrarian and prove you're right. Different founders have different forms of feedback they listen to. It might be talking to other CEOs, or other operators, or trusted advisors, certain customers. Some might be very data-oriented, so you just run the experiment and ask for forgiveness after you proved it works, whatever. Everyone's got a different thing they respond to. You try to figure out what actually influences the CEO and build that case, whether it's through an experiment, the right customer intro, the right external advisor. If they rebuke that as well, then you got to disagree and commit, or find a new company to join, or start your own. Like I said, it's their company. They can make the call. I remember when I joined Pinterest, I was just coming off 100X increase in user growth from Grubhub. I was ready to drive the same sort of impact at Pinterest, but no one knew who I was. I didn't come from Facebook or Google like most of the other people, or Pinterest. No one gave a shit about Chicago startups at the time, so when they didn't trust my proposals, I just went and talked to the heads of growth at all the startups they did respect. I talked to Dropbox, I talked to Facebook. When they said all the same things I was saying but I said that they said it, not me, that was, sadly, more convincing. I didn't care because I still got what I wanted out of it, which is to do the right thing to grow the company. Now you're one of those people that people go to. If Casey says it, it's probably the right way to do it.…

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