The Exchanges

Q I'm honored as well, so thanks for joining me again. I have a lot of stuff that I want to chat about, but first of all, I'm just curious, what are you up to these days? I know you left Eventbrite as CPO. I know you're doing a few advisorships with startups, but how are you spending your days, and what do you think is next for, for Casey Winters?

A So I'm still, still spending some time with whatnot and Eventbrite as, as advisors. You know, I stepped back from the, the CPO of Eventbrite in October, but still working on some Long-term marketplace strategy stuff, some growth strategy stuff. Uh, I'm on the board of a company called Beek, which is like Netflix for audio in Latin America. And I'm doing some angel investing and in marketplaces and what I call tech debt as a service, which is, you know, what are startups that are building out things that were hard for my teams in the past to like build or maintain inside previous companies. The other thing I'm working on is revamping the product strategy program. For Reforge. So I got some things keeping me busy, but, but definitely not as busy as I was last year.

AI assessment note: “I'm still, still spending some time with whatnot and Eventbrite as, as advisors.”

Q top-down? Here's what we should be doing, versus the team kind of bottom-up figuring out what to build. And so I'd love to spend a little time here. So maybe just to start broadly, what is this? You kind of came up with a framework of how to think about when founder intuition should overrule say team expertise and how that changes over time. So maybe just talk about that.

A Yeah. If founders are lucky slash good enough to find product market fit, they've usually built up all this intuition about their customers, about their product and their business that are really hard to explain to others and may even be like subconscious. So when they start to hire people, you know, these people will come in with a lot of, you know, excitement, ideas, maybe even really relevant experience, especially, you know, senior leaders. And I've seen some founders are like, cool, I need to let these experts start to own these areas and get out of the details. And I think that's actually the opposite of what you want, because none of these people know the business as well as you get. You actually need to direct them until they show you they've really got it and are making better decisions than you would. So this is not a founder example, but I remember when I hired Erica Warren to build out our loyalty program at GrubUp. She now leads growth at change.org. And after a month or so, she was like, dude, you're in all my meetings. I got this. And you know, that let me know she was in a different part. Uh, the situational leadership framework than I had put her in. So I backed away and, you know, she crushed it from there. Founders will put a lot of new leaders in that delegate bucket too quickly. It's like, ah, it's theirs. They got it. They know more than me. When founders …

AI assessment note: “You actually need to direct them until they show you they've really got it”

Q On that topic, when should companies focus on growth? And as a second question, when do you think they should hire a head of growth or someone full-time focused on growth?

A Like I mentioned, uh, well, you don't wanna focus on growth before product market fit. You want to be thinking about how your product can grow scalably, you know, pretty early on. So, you know, early growth definitely needs to be done by the founders. I tend to separate growth into two phases. I call the first phase Kindle strategies. These are those non-scalable hacks to get your early users. And I think those are generally done by founders, maybe some early team members. Fire strategies are the ones that drive scale. That's, you know, what you're mentioning, content loops, sales loops, viral loops, paid acquisition. And to me, the goal of your Kindle strategies, these like non scalable hacks, they only exist to unlock the fire strategies, to unlock the things that could take you to millions of users. And it's once you unlock a fire strategy, that's when I think you think about hiring someone full-time on growth to fully harness that new growth loop you've built. That could be a salesperson. If it's sales, it could be, you know, growth PM, if it's viral or you just see content, or it could be a performance marketer if it's ads, but it's once it's like, okay, we've sequenced to a growth strategy that actually scales. Let's go find someone who's awesome at that, who can make it, you know, 10 X better. That's how I think about it.

AI assessment note: “once you unlock a fire strategy, that's when I think you think about hiring someone”

Q my answer is just like money was so freely available at that point that they were able to, like a lot of this was spend that so much money raised. You said they're raising a hundred million dollars every six months. Like, is it even possible in today's climate where you can't actually raise that much money to have any sort of chance to eat at DoorDash or an Uber?

A Yeah. I mean, clearly they took advantage of the zero interest rate environments that we talked about earlier. That is not a replicable strategy in. So any approach to compete with them has to be competing on a very different angle, um, because yeah, they can spend you into the dust. So, you know, we'll see if anyone's able to build a way that creates new supply and market. I think you and I've seen a couple of earlier stage examples of that. We'll see if any of them scale or something that feels Cheaper or more fun on the demand side. That would be like another way to potentially disrupt things. I think another thing that was working pretty well before the pandemic in building disruptors was focusing on the pickup use case, which, you know, DoorDash cannot do as easily. Like they've tried, right? But like their whole value prop is the delivery network, which you don't need for pickup. Uh, but of course the pandemic put a lot of those startups grinding to a halt as well. So, you know, there's always angles, but you're gonna need to be incredibly clever because Just attacking with a war chest is not really gonna work.

AI assessment note: “any approach to compete with them has to be competing on a very different angle”

Q There's probably PMs listening to this wondering, shoot, am I one of these? Am I just like following a bunch of frameworks? What's your advice for someone that may fear that, oh shoot, this is maybe who I am and I don't want to necessarily be this and what could they maybe do?

A I always advise going to companies where you can, you know, learn quickly and, and try things. Right. And I think, you know, it's certainly okay to like learn a bunch of frameworks. There's a reason I've invested a ton of time in Reforge because I think it actually really does help people. To see how other people have built things in a way that they can, you know, scale to their other companies. But you have to understand that the job is not to follow the process. The job is not to learn every framework possible. The job is to figure out how to add value to customers that translates into value to the business. And, you know, just reorient your North Star if you've gotten away from that. When I joined Eventbrite, you know, there was this team that Didn't ship anything in a quarter. And, you know, I went to the designer who I knew and, uh, You know, I know that he, you know, likes to, likes to get stuff out there and likes to get feedback. And I was like, dude, you didn't ship anything. Like, how could you have gone the entire quarter, not shipped any of your designs and felt that that was okay? And if you didn't feel it was okay, why just censor yourself? Come to me, tell me why this team is not letting you ship. There's just no way you can get better as a designer. There's no way you can have impact on the company. There's no way you can have impact on our, on our users. So, um…

AI assessment note: “The job is to figure out how to add value to customers that translates into value”

Q such important advice that I think a lot of PMs don't recognize how important it is to prepare for important meetings like this. Just to give folks context, maybe that aren't doing this sort of thing when they're working at a larger company, how much time do you spend or, or an ICPM should spend on preparing for these things just to set a little bit of a reference point?

A Well, you know, it's an interesting question because I think different people have different styles on how they want to handle this. I'd say the way my brain works in these situations with it, which I think is a little bit atypical. Is I'm actually a little bit better if I am free forming a lot of elements and just speaking from confidence in areas I know versus specifically trying to lay out every exact bullet point I want to hit. I'm going to show up as more comfortable. I'm going to show up as more dynamic and I'm going to be able to engage in a more thoughtful conversation. So for me. My approach to these sorts of things is I write a lot. I write a lot of notes. I write a lot of documents. And then in general, for any of these types of communications, I am just pulling from things I know deeply because I've written them down. I've thought, I've thought a lot about them. For a lot of other people, they really just need to spend a lot of time on prep to make sure they nail the communication they want, they want to nail. And I found it requires a different amount of investment for different people on my team. So the, the point is not as much how much time you spend. It's how well do you really know the material and how well do you really know what your audience is going to care about with that material so that you are prepared for every question you might get. So I'll, I'll gi…

AI assessment note: “the point is not as much how much time you spend. It's how well”