Jake sees letting go as a way to avoid CEO bottlenecks

Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

1. 1:03:29

   Where have you had to grow as a CEO over the last couple of years? Yeah, I think I think like letting go is like a good one where you just like slowly letting go of like more and more things, right? Like letting go of, you know, like sections of the business to allow people to kind of like own them more deeply. Because like if I'm just like holding over engineering, like, you know, it's like nobody can kind of grow and then make those most mistakes. So like I've always just like try to figure out how much I can kind of like let go and just various different, you know, things. Right.

2. 1:03:56

   And so just letting go is like going from engineer to operator to like business person, you know, all of those other things. And so just like letting go of all those those toys and especially the ones that are fun that I really enjoy like working on, like from an engineering perspective and all that other stuff. Like sometimes I just I'm like, wow, damn, that's that's a really fun problem. And this problem that I'm working on today, it just sucks.

3. 1:04:19

   It's just not a fun problem, you know, but you have to go in and do those things sometimes. And so it's just a lot on like letting go and just doing the one thing that will move the business forward for that week and just do that 52 times a year. Are there aspects that you recognize today where you were bad as a CEO a year ago that you're good at now? Oh, I think I think like the classic one for like founders is just like you don't realize how fucking bad of a manager you are until like you get better at being a manager. And I still think that that's the journey that I'm on and like learning and like, you know, now that we have our first kind of like group of like leaders internally forming, etc. You know, like learning to manage managers is different than learning to be a manager oneself. Right. And so you just have to consistently put yourself in a spot where you are just like bad at something. Right.

4. 1:05:02

   Can you give a tactical example on this? Like, this is a fast, I think every founder CEO is going through this journey at some level. Like, what were you bad at managing? Was it communication? Was it holding people accountable? Like, give us a tactical example. Sometimes it's communication. Sometimes it's feedback. Sometimes you're like too direct. Sometimes you're not direct enough, right? Like, you know, we use the concept of like right internally, right?

5. 1:05:25

   Like it's like right trust, right? Precision, right? Clarity, right? Whatever, right? Because, you know, depending on the scenario, there's just a different amount that you can go in and apply, right? Like, you know, I've been working with a bunch of designers recently, right? And designers are like wonderful, wonderful people. They see everything. And we have this concept internally called progress picks.

6. 1:05:45

   And so it's just, you're working on something and you go and you share it, right? You're just like sharing it, right? And like engineers, like they will, they're very precise, but they miss things once in a while, right? And designers are very different, right? And so having to go and learn those lessons to be like, oh no, like designers have like an enormous sound of perception. Like they just, they pull in so much input from all this thing because they don't miss any of that, right?

7. 1:06:05

   Okay, cool. We should do like design crit, which is like a standard thing where it's just like, hey, you bring all the designs together and you say like, hey, like let's talk about these things, right? Let's give really, really clear feedback versus you share it and you get feedback from various different people, which works really, really well for engineers because they can just be like, hey, I'm not going to listen to 80% of that shit.

8. 1:06:21

   I'm just going to go in and do this, right? So yeah, I think that those are just things that you go in and learn. And even in that statement that I just uttered, there's probably designers like listening to be like, I don't even know if he knows what he's talking about or whatever. And it's like, they're probably they're probably right. Right. And so you just have to have that like learned mindset of you. You will consistently be the first person on the dance floor. You will consistently be the person that like, you know, has to figure out some sort of new problem. And you have to surround yourself with people who are going to go in and be able to go in and do those things that you're just like bad or weak or whatever at and like either don't want to or just don't have the time to like get exceedingly, exceedingly good at. Right.

9. 1:06:56

   And I think like, you know, that's why you have to let go of the things you're really good at, because you will just like convince yourself that like, that's totally fine. And like, it's, it's totally good to just like leave that thing there. Right. But you will end up, you will blink. And in retrospect, you will realize you were bottlenecking the company, right? You'll bottleneck the company just by doing that. Right. And if you want people to be successful, if you want your investors to be successful, the people that you're working with, if you want them to be the best, best, best version of themselves, you need to figure out how to get out of those bottlenecks, like as soon as possible, you know?

10. 1:07:25

    Is there something that you're working on right now on making yourself better as a leader, as a CEO?