Drew Houston: belief

Transcript context

…Awesome. The way you described it to me, which has really stuck with me, is as a founder, as you said, you're in there leaning in, doing, on top of everything, micromanaging. Then you lead out, and hire execs that you think are smarter than you, and delegate more. Then it's like, "Oh, things aren't going great," and come right back into it. Yeah. Specifically, it's often well-intended or it's often even not conscious, but as you hire these execs, and then you also build up an HR function, you get coaches, and things like that, and then the things are not going well, one thing that can happen is you start collecting all this feedback. People are like, "Wait, if I can give Drew some negative feedback, then maybe I can displace some of the ..." It's sort of easy to get into a situation where you're sort of being my to-do list of problems, just weaknesses, and flaws I needed to work on was super long, way longer than anyone else's. On the one hand I'm like, "Yes, I am wholly accountable, and responsible for everything in the company as its CEO." That's not wrong. But you can end up just carrying too much of the water, so a lot of it ended up having to be this pushing back a bit. Be like, "All right, yes, there are things I need to work on, but that can't be an excuse for my execs to somehow evade accountability." There's these sorts of systemic things that can creep in for sure. Then you get this feedback, and you're like, "Now, I'm doing all this behavior," or, "Now, I'm behaving in ways that I don't think are really right." Or I'm like, "Everything is just negotiated compromise with everyone on the roadmap or on how we behave or strategy. " At some point you end up blowing that up as a founder, and that was certainly my experience. This episode is brought to you by Vanta. When it comes to ensuring your company as top-notch security practices, things get complicated fast. Now, you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more. With a single platform, Vanta. Vanta's market leading trust management platform helps you continuously monitor compliance alongside reporting, and tracking risks. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's V-A-N-T-A.com/lenny. I think this is a great segue to get into chapter three. Basically, what I understand from what you're going through right now is you're rebooting the team, you're rebooting the core business, you're rebooting the product. I think it might be good to start with the team. You talked a few times about just how you feel like you got to a point where the team wasn't shipping as much as you thought you would, as much as you think they should. Talk about maybe that part of it, of just realizing, "Hey, this part of the business needs to change. Then we can talk about the product, and the direction you've discovered."…

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