Casey Winters: evaluation

Transcript context

…Part of this, you have this cool chart of just over time, the founder expertise becomes less and less relevant. I guess, is that because they just don't spend as much time with the customers because they have other stuff going on or they hire people that are smarter, and then over time, the team expertise goes up? If you're lucky enough to scale a company, there's just more and more things going on that all will reach the founder in some way, but it means more breadth and less depth on any particular issue, and the reverse is true for people you hire. They're able to get really deep into things that maybe you were really deep into two years ago but you just can't stay deep in anymore. I built this chart on, or I guess I should say table on the different phases of a startup. When you're finding product-market fit, everything goes through the founders. You cannot outsource that. Then when you start scaling the company because you found product-market fit, it's the first time that founders run into this classic problem of what got you here won't get you there. What got you to product-market fit was iterating on product and doing things that don't scale. Guess what? You found a product that works. Don't do that anymore. Make it scale. Don't come up with new products. You found the one that works. The reason I came up with this framework originally is when I was at Grubhub, we were scaling pretty nicely and fairly organically. I think Mike and Matt, the founders, had intuited these phases of building a company pretty well, but we acquired a competitor and I saw how that company we acquired operated. Even though they were largely in the same phase as us, they still operated like they were founding the company. Everything was going through the founder. Intuitively, I was like, "Oh, this is why we're acquiring you, and not the other way around." I think it's really hard for founders to get those signals organically, and I think it's up to us as employees to help. The founders can listen to the signals or not listen to those signals, but that's part of why we're here, but we should also give those signals when we're confident we really get it. Not come in day one being, "I know what your sales strategy should be. You're doing it all wrong." Because chances are, the founders weren't doing it all wrong. They knew something you don't know about yet. What is it that you think made it such that you won and they didn't? Is it because they didn't invest, they didn't shift to scaling and delegating to their employees as much as the founder just telling everyone to do it?…

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