John Cutler: evaluation

Transcript context

…I was reflecting that the newsletter, it's almost like an emo band, The Beautiful Mess, it's so angsty. It couldn't have been more... If I had a band, I did not have an emo band when I was 16, but if I did, I would've called it The Beautiful Mess. So, it's probably pretty consistent with personality to do those things. I mean, I actually really appreciated Jason pointing that out, and in fact, at the end of this year, I put this post out to people saying, "Hey, here are things I'm grappling with, like the actionability of the content that I put out there, diversity of product advice, it's important to me," and then what it's like to just be a weirdo. We all have our weird freak things to do these things. And so, what does it mean to embrace those things? So, it was really timely I thought that Jason put that out there, and so maybe I'll give a little background about the newsletter and what I was looking for that. And so, I think that the first thing that I did was four years ago, I kind of scanned the product advice landscape and I noticed three things. First, there's sort of three perspectives that pervaded, and again, I just want to make a huge caveat, this is not a judgment on any of these particular perspectives. It's more like I noticed a lot of it. And the first was that to be successful, number one, maybe success is tools, skills, mindset. So, that's kind of one group of particular things. The second that in terms of worldviews, we mentioned international worldviews too, but there was a high percentage of product advice that was kind of grounded where you think it would be grounded. So, it was grounded in this idea of meritocracy. Success is primarily about merit, very highly individualistic, and we don't realize that in the US until you do meetings with other teams, just how individualistic we can be when it comes to how we think about teams should be set up and stuff. And then I think the third thing I realized was that it was very often very context free, and I mean that actually in the nicest way. It was optimized to make sure that it could be actionable, that someone could take that away. That's what I really like about the content that you put out there, and I like about a lot of the guests on the podcast. They kind of lay it out in those particular things. And so, to kind of go through, yeah, those tools, skills, mindset, that makes sense, right? Who does not want tools to be better? In fact, a lot of the podcasts I like, we can get into that later, are like, "We're going to give you the tools and tactics that the best people do." So, I really like that kind of stuff as well. The second part of that is this idea of success be mostly about individual skills in jobs. So, this idea of great leaders, high performing teams, 10 x people, kind of go on and on. And then the product mindset stuff which is a little bit like you have it or you don't, or you develop or you don't. It's very mysterious. rs, high performing teams, 10 x people, kind of go on and on. And then the product mindset stuff which is a little bit like you have it or you don't, or you develop or you don't. It's very mysterious. So, again, I'm going to go through these things and then think about how they inspire me. Part of me was like, "Okay, there's a lot of that stuff, but maybe not as much stuff kind of unraveling the dynamics that happen behind those things." So, the meritocracy stuff and the individualism stuff, it's basically the people rise to the top, they try the hardest, they work the hardest, the best in companies employ them. There's top tier companies, there's second tier companies. So, there's this very hierarchical view, and as I started to also dig in more into the stuff in Amplitude, I was like, "Wait, there's something right and wrong about this at the same time, there's something true but not true at the same time. " So, that's something that I wanted to be able to explore in doing it. And then the context free advice was obviously I noticed more and more that people trying to put tools in play out of context sometimes had worse effects than them just not doing it at all to do that. So, anyway, I kind of thought about it as a product, like, "Okay, what's my opportunity here? There's a lot of this great advice. It's very actionable. I don't know. In the US were pretty individualistic, so the advice probably lands with people really, really well, and then also it's really actionable," and said, "Okay, well, what would be my particular angle?" So, I thought about the angle, about wanted to explore three things. I think the first one is this idea we do work in these complex adaptive systems, and so I really went deep in that particular area. So, we work in environments. There's lots of things that are interdependent on each other. We don't work in closed systems. I mean, if you're in the Bay Area, you're in this broader system called the Bay Area that's in this broader system called California that's in this broader system called the United States. Your team is in a team of many, many teams in your company. The systems are non-linear. The bird flapping its wings in Brazil creates the tornado type of stuff. And so, I wanted to make sure that we got dug into that particular stuff in The Beautiful Mess stuff. The next thing is that I'm a sucker for weird counterintuitive dynamics in companies. I don't know what it is. I absolutely love that. And so, maybe I'll give two examples. One, I'm obsessed with this idea of high work in progress, from a human level and a team level. How even though we know that if you try to do less at once, you'll be more effective, teams routinely just load themself up with work? And so, in the newsletter, I wanted to explore stuff like that, like why, when a bunch of people know irrationally that you should not load yourself up with work, why do really, really smart, capable, intelligent, passionate people in their personal lives and on their teams just load themself up with work? What are they optimizing about? So, that'd be like one example of counterintuitive stuff. The other stuff is strategy stuff. in their personal lives and on their teams just load themself up with work? What are they optimizing about? So, that'd be like one example of counterintuitive stuff. The other stuff is strategy stuff. Every company has these three pillars, and it seems really smart for the CEO to have this really clear three pillars, but then everyone walks away from the meeting and be like, "I don't know what we're with doing." That's another example of a counterintuitive thing. So, that was the second thing, the counterintuitive stuff. I love the complex stuff. And then frankly, I think the other thing is I just wanted to help people who are weird like me do those things. So, I would say I'm really, really triggered. People will say, "But it's probably triggered by Jason." He said, "Why? Bring solutions not just problems." That's my krypton, right? I like the systems thinking stuff. I like all that. So, anyway, long story short, wanted to help people like me. I like the complexity stuff. I like all these weird counterintuitive dynamics. And then I thought that there's a lot of representation for the very deterministic advice that people have. ... advice that people have.…

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