Lenny's Podcast: Product | Career | Growth
00:31:26 · Casey Winters
[00:31:26] S0: 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, you know, people you hire. Right? You're able to get really deep into things that maybe you were really deep into two years ago, but, you know, you just can't you can't stay deep in anymore. So I I I built this, you know, chart on... Or or I guess I should say table on the different phases of, you know, a startup. Right? And when you're finding product market fit, like, everything goes through the founders. Like, you cannot outsource that. And then, you know, when you start scaling the company because you found product market fit, it's the first time that founders run into this, like, classic problem of what got you here won't get you there. What got you to product market today 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, you know, framework, originally is when I was at Grubhub, you know, we were scaling pretty nicely and and fairly organically. I I think, Mike and Matt, the founders, had intuited these phases of, like, building a company, like, pretty well. But we acquired a competitor, and, you know, I saw how that company we acquired operated. And even though they were largely in the same phase as us, they still operated like they were founding the company. Like, everything was going through the founder. And, you know, intuitively, I was like, oh, this is why we're acquiring you and not the other way around. So 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. And, you know, the founders can listen to the signals or not listen to those signals, but that's part of why why we're here. But we should also give those signals when we're confident we really get it. Not like coming day one being, know what your sales strategy should be. You're doing it all wrong. Chances are the founders weren't doing it all wrong. They knew something you don't know about yet.
00:33:33 · Lenny Rachitsky, Casey Winters
[00:33:33] S1: 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? Correct. Right. Like, the, [00:33:45] S0: everything was, like, not moving as quickly because everything had to go through the same person to get done. So it just allowed them to not launch as many markets, to not sign up as many restaurants, to not figure out as many, you know, growth channels, yeah, as we had done. [00:33:59] S1: Got it. So they just bottlenecked themselves, and they weren't able to move as fast because the founder thought they needed to make these decisions, and they were still the ones that knew everything. Yep. That makes me think about most companies, maybe not most, but many founders just, like, believe they have the answers. Like, they are confident they know what to do. Right. And it's rare they get to a place of like, no. I actually don't. [00:34:21] S0: Well, I would say no one gets to no no one gets to it super intuitively. [00:34:26] S1: Any advice for either as a employee at a company with a founder like that or a leader of just how to push back and help the founder understand maybe you should let go and trust people to make decisions?
00:34:38 · Casey Winters
[00:34:38] S0: I think the first thing is you have to understand that it's their company, not yours, and that founders have impossible jobs. They're not going to scale perfectly with the needs of the company. Like, it's just something's gonna be off. And it may be because there's a whole lot of hubris by being the one of a thousand startups that made it, or, you know, they just have personal styles, but they can run the company any way they want. And I think it's sometimes surprising when founders actually want to run things suboptimally. Like, I think we've seen examples where founders just wanna 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. And, you know, of course, that's gonna happen, and those are some of the the worst cases. But I think, you know, 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. And 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, you know, forgiveness after you prove it worked, whatever. Like, everyone's got, like, a different thing they respond to. So you try to figure out what actually influences, you know, the CEO and build that case, whether it's through an experiment, the right customer intro, the right external adviser. And if they rebuke that as well, then you gotta 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, you know, a 100 x increase in user growth from Grubhub, and 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, you know, 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.
00:36:54 · Casey Winters, Lenny Rachitsky
And when they said all the same things I was saying, but I said that they said it, not me, that was sadly more convincing. But I didn't care because I still got what I wanted out of it, which is to, you know, do the right thing to grow the company. [00:37:09] S1: And now you're one of those people that people go to. If Casey says it, it's probably the right way to do it. [00:37:13] S0: Whether I'm correct or not, it is a role I sometimes play in the ecosystem, I will admit. [00:37:17] S1: Is there an example where you were convinced something was the right way to go and the founder at one of the companies you worked at had a different opinion, they were... They had ended up being right? [00:37:25] S0: When I was at Grubhub, one of the ideas one of the founders came up with was to build an app for delivery drivers. So at the time, you know, restaurants had their own delivery drivers. They did not work for us. And we wanted to build an app for the delivery drivers so you could see where the food was along the way. You could know if it's a five minutes away, whatever. Right? [00:37:43] S1: Mhmm.
00:37:43 · Lenny Rachitsky, Casey Winters
[00:37:43] S1: Mhmm. [00:37:43] S0: Domino's was the first to have done this at the time, and we thought that would that would make a bunch of sense. And I was just like, how am I supposed to convince the delivery driver who doesn't have a relationship with us to download this app from Grubhub to actually turn it on to create, you know, anxiety for the consumer of, like, they maybe didn't take the right turn or whatever? I was like, I don't think this makes sense. No one's gonna use it. And, you know, Mike and Matt, like, overruled me and and pushed us to do it. And in the long run, it ended up being quite necessary because of the innovations around DoorDash and Postmates and and later Uber Eats into having their own delivery network and and us needing to counter that, that's, of course, a key piece of technology that needs to lever... Have parity with those new services. So that was an area where perhaps they were thinking a little bit more longer term than I was. And, you know, I was not able to kinda get where they were going on on the longer term time horizon of of how this would be actually ultimately adopted and useful. [00:38:38] S1: This is an awesome segue to the next area. But real quick, how did they get drivers to start using this app? Was there anything really clever they did?
00:38:38 · Lenny Rachitsky, Casey Winters
[00:38:38] S1: This is an awesome segue to the next area. But real quick, how did they get drivers to start using this app? Was there anything really clever they did? [00:38:45] S0: I I think it was fairly low adoption for a while and leveraging, basically, restaurant authority. So if we were able to push on our restaurant customers effectively to say, like, hey. If you use this, it'll get you more orders. We'll get you prominence in the the UI, things like that, to then push down, you know, to their direct relationships with the drivers to get them to adopt.