Lenny's Podcast: Product | Career | Growth
00:34:39 · Brian Halligan
[00:34:39] S0: One of my... It was actually Winston from Harvey, said this a year ago, and I was like, that's bullshit, but I actually think he was right. He, he's like, "You can just do a lot more." You've got AI agents doing stuff, everyone's more productive, the software developers are more productive. Something that used to take you a year takes two months now. And so, the amount of projects and the amount of stuff you can do is much, much more, I think he's right. I think that's a little dangerous. Let's say you found your beachhead market, and that beachhead market is really good, and it's very deep, there's a lot of work to do, I think what's dangerous for companies is they hop to that second act too quickly, and they lose focus on that first act. And this isn't a completely perfect analogy, but you think of OpenAI and ChatGPT, and its consumer app is doing incredible, and they're doing lots and lots and lots and lots of other things, and then Gemini comes out and they've kind of focused back on the core. I think there's a lot of competition, everything is moving fast. I do think people get more done, and I think that impacts everything. The planning cycles used to be a year, I think the planning cycles now are three months long. Yeah, that's a big change. I think it puts pressure on the CEOs to be faster and better decision makers. I just think of times in HubSpot when things slowed down and there was churn, it was usually my fault. It was because there were some hard one-way door type decisions on my desk, and maybe every year I would sit down and I'd open that one-way door or close it, and it just freed everyone up and we just started moving so much faster. I think people need to be making those decisions and walking through those doors much more quickly than they used to. I think that's new and different. I was someone who always valued optionality, I think there's a massive tax in optionality when you can move this fast and try a lot of things. So, I do think the job's changing a lot.
00:36:45 · Lenny Rachitsky, Brian Halligan
[00:36:45] S1: Yeah. And there's so many reasons this is happening. One is just technology is just every week there's a new shift in what is possible. [00:36:53] S0: Yeah. [00:36:54] S1: So, if you're spending all these months thinking and planning, just what a waste of time it ends up being because so much is changing. [00:36:59] S0: I know. Yeah, it's hard to keep up.
00:37:03 · Lenny Rachitsky
[00:37:03] S1: [inaudible 00:37:04]. Luckily we got some sweet podcasts to check out, to keep up to date with what's happening. We'll link to yours, of course. Here's a puzzle for you. What do OpenAI, Cursor, Perplexity, Vercel, Plaid, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, SCIM, RBAC, audited logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs, with a modern developer platform built specifically for B2B SaaS. Whether you're a seed-stage startup trying to land your first enterprise customer, or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unlocking growth. They're essentially Stripe for enterprise features. Visit WorkOS.com to get started, or just hit up their Slack support, where they have real engineers in there who answer your questions super fast. WorkOS allows you to build like the best, with delightful APIs, comprehensive docs, and a smooth developer experience. Go to WorkOS.com to make your app enterprise-ready today. Let's talk Halliganisms. Essentially these are nuggets of wisdom and advice that you find yourself sharing often, you've written about a bunch of these online, and so let me just go through them and then just share the synopsis of the advice and the lesson around this Halliganism. The first is, "When you have to eat a shit sandwich, don't nibble."
00:38:30 · Brian Halligan
[00:38:30] S0: Okay. Completely stole this from Ruth Porat, the CFO of Google. I saw her quote somewhere, I'm like, that's it, she's put a perfect thing on it. And I'll give you an example where I think this will play out over the next couple of years. I think within the next couple of years there'll be a real retrenchment in valuations, and some will live up to valuations a lot [inaudible 00:38:54]. Like, if I look at the public markets, they're very tight right now, it's like the anti-bubble. And I look at private valuations, it's like a real bubble. I think there's a reckoning somewhere down the road. And a lot of companies are going to have to do layoffs. A lot. It's never fun, it's usually the worst thing in the history of your life, and the temptation is to do, well, just do a little one now and we'll grow into it, and then they do another one in six months, and then another one. I think with everything, including this type of thing, it's just rip the darn Band-Aid off, tell everyone the bad news, they're adults, they can handle it, and get it done. And I think people avoid that. I think that's good advice Ruth Porat is giving. Because you're going to have bad news to deliver, bad shit is going to happen to your company, even though it looks like it's going amazing right now, weird stuff's going to happen. And you're going to have to deal with it. And we had a lot of weird stuff happen at HubSpot. There's a basketball coach named Mike Krzyzewski, he's Duke's basketball coach. All time winningest college basketball coach ever. If you go to a Duke basketball game, you can hear him yelling from the sidelines, "Let's play, let's play." And what's going on there is when a college basketball player is playing in the game and takes a shot and clanks it off the rim and misses it, they have a strong tendency to go play overly aggressively on defense in the back court, and many times compound their error by making a foul or something like that. And what he wants to do is people to make their error, forget about it, and move back down the other side of the court and run the play. And so, actually there were times in HubSpot's history where we had the Mike Krzyzewski's face on a huge slide in front of the company meeting, saying, "Next play," because there was an unforced error, and we need to deal with it and move on.
00:40:54 · Lenny Rachitsky, Brian Halligan
[00:40:54] S1: Is there a story of that that comes to mind that is interesting and worth getting into? [00:40:58] S0: There was a lot of them. But I remember in 2000, it was the last day of March in 2019, and we had a really bad outage all day. And we never really had one of those, and it was bad. Customers were unhappy, a lot of customers canceled. I had a lot of customers yelling at me. And I remember that company meeting, I cried in front of the whole company, they couldn't believe it happened to us. And I remember using the Next Play slide on that one. Yeah, we made a lot of mistakes at HubSpot, a lot of bad things happen to companies, and most of them are self-inflicted. And a lot of them are the old saw-like, companies are far more likely to die of overeating than indigestion. Usually it was when we were trying to do too much. [00:41:54] S1: I haven't heard that version, I've always heard most companies die have suicide versus homicide. Though indigestion- [00:41:59] S0: That's true too, by the way. [00:42:02] S1: Oh man. Okay, so next Halliganism, "Never waste a good crisis." That's something that people hear, I'm curious just what's the lesson here, and then is there an example of this where you learned this lesson?
00:42:02 · Lenny Rachitsky, Brian Halligan
[00:42:02] S1: Oh man. Okay, so next Halliganism, "Never waste a good crisis." That's something that people hear, I'm curious just what's the lesson here, and then is there an example of this where you learned this lesson? [00:42:16] S0: I'll just follow on to, most of the good things that happened in HubSpot came out of a crisis because we would take pretty drastic measures to fix it and make sure we didn't do the same thing again. And so, in this particular case, we really rethought how we deployed software, how we thought about making software in a way that was incredibly healthy. And we haven't had a serious outage since. The quality is much better. And kind of an interesting thing with HubSpot is we started as a marketing software company, and we pivoted, had Salesforce came into our market, we pivoted into CRM. And one thing that... If your marketing software goes down, if your workflow, if there's a bug in the workflows or something like that, it's bad, but you survive it, you wait a little bit. If your CRM goes down, particularly on the last day of the quarter, you're really impacting your customer's ability to do business. So, that was a mindset shift that we hadn't quite come to terms with of how important we were to our customers. And so, we made a lot of changes based on that crisis. Usually very good things came out of crises. [00:43:26] S1: So, there's the lesson there, something's going wrong, is it just like over-correct? Use this as a way to- [00:43:31] S0: Yes. We always over-corrected. Yeah, we almost, we purposely swung the pendulum hard the other way.