The Exchanges

Q never had any direct reports. I know that's somewhat related to a piece of advice you often share, which is to lean into your strengths. And to not do things that you're not amazing yet. So, can you just talk about why this is the case? Why don't you have any reports? And, and then this, I think, this idea of just, like, strengths and the importance focusing on strengths.

A Yeah. Um, let me, I'll tell you the quick story, um, as to how this came about. Well, my co-founder and I had the kind of founding meeting for HubSpot. This is the, like the week where we've decided we're going to do this. And then we have this list of questions, uh, or topics for the kind of founders discussion. Um, one of them, uh, and I, this, I think I've published a list of these, these are the questions all co-founders should ask each other in that kind of, uh, early, early period. One of the ones it's like, okay, well, who's going to be CEO? This was an easy one, uh, because I had been CEO twice before and had figured out I'm not that good at it. I actually suck at that. Um, that's, and, and one of the reasons I suck at that is that part of the CEO role is being good at managing people. It's not just about leading and having a vision of whatever you actually have to do, uh, kind of the management as a craft. And so that part I already had in my head, I think Brian, my co-founder already had in his head that we, that, that's how this conference, that was a very quick conversation. And in the moment, as soon as I had kind of had that wind behind me, he's like, okay, well, I don't want to be CEO. Brian wanted to be CEO because he'd never done it before. Like, okay, that was easy. And then I said, oh, and by the way, um, I don't want to have any direct reports. It just, I co…

AI assessment note: “one of the reasons I suck at that is that part of the CEO role”

Q and what I should talk to you about. And he said that you're very good at zigging when other people are zagging and zagging when other people are zigging. And I think that's already come across in our conversation. I guess, is there anything else along those lines that you think might be helpful to people in terms of how you think about that or examples of that in action?

A So this comes down to kind of kind of high conviction, low consensus bets. Um, and so we had, uh, Like three things that we were zigging. And by the way, it's not just me. My co-founder and I both have that kind of zig versus zag, uh, and we can ask ourselves and we ask ourselves this to this day, right? It's like, okay, well, we understand that this is the way the kind of world moves. This is the way it's normally done. But have we considered this completely, not saying we should do it, but have we considered this alternate kind of alternate path? So I would encourage you at any stage of the company, uh, you don't necessarily have to do the zig versus zag, but you should at least know what the zig would have been and have talked it through. So that's kind of thing number one. Um, some of the best startup advice I've heard that I've ever given is startups should focus on one thing and be really, really exceptionally world-class, better than anyone else at that one thing. And one of our early zigs is we are going to do exactly the opposite of that. So from year one, HubSpot decided to build an SEO tool, web analytics, blogging tool, content management, all of it. And every one of those categories that we were building a product in, literally this is year one, had great products with great companies behind them. And so it's like, okay, well, why would you do that? And the reason …

AI assessment note: “one of our early zigs is we are going to do exactly the opposite”

Q Wow. I feel like I've just learned so much about you and how you think just from that question and how you approach this problem. On this humor piece, I'm curious, any lessons to share on how to be funny?

A So one of the kind of tricks of the trade in humor, and you learn this, um, particularly in standup comedy, but just any comedy, and I just hadn't thought of it this way, um, is that, and this is very tactical, but it works and it's a very easy thing to apply. So let's say you're looking at, and most of us in, in, uh, You know, we're not stand up comedians. We're not gonna tell jokes in a classic sense, right? And even stand up comedians don't tell jokes, right? Like they, they actually have stories and they happen to have a punch liner, a punch liner too. So that, uh, two tactical pieces of advice. One is when you're telling the story, whatever the funny bit is, those have to literally be the last words of that particular segment, right? So once you deliver it, Then you have to stop talking. And the reason you have to stop talking is the audience needs about a half a second to react. And then they want the permission to laugh. And if you're continuing to say words, it's going to make them feel awkward and it's going to be less funny. So even if like moving a phrase in the sentence that you're about to say, it's like, well, that sounds kind of weird to put those set of words at the end of the thing, do it anyway, even though it's awkward because it will actually work better. So that's kind of tip number one. Tip number two on LPM generally is that Um, have a story such that you…

AI assessment note: “two tactical pieces of advice. One is when you're telling the story”

Q Okay. And yeah, we don't have to get into the, we're getting to the real, the first principles of everything. Talk about that. What does that mean when you, and what does that look like when you're running a business?

A Okay. So in lay person's terms, um, the second law of thermodynamics, um, paraphrasing here is that over time, unless you intervene, everything goes to crap. I'm paraphrasing, right? Which is essentially the amount of disorder and randomness in a system is going to increase over time. You see this, like when you break an egg, the break of it, like molecules don't come together and form an egg, right? That doesn't happen. It's always the other way around becomes disorderly and more random. That's the second law of thermodynamics. And this happens in companies as well, right? Like it happens in code, like almost every level of abstraction, you will see, uh, some variation of this. Um, and so the way I think about this is that in the early stages of a company, you're essentially You're trying not to die, right? That's the thing. Like, okay, like Friday one, don't die. Uh, in the second phase of a company, you're trying not to stagnate, right? Like you still want to be able to drive growth and be able to do things like, okay, we managed not to die because stagnation is essentially death. So we're still trying not to die. But then, um, the third stage is you're fighting complexity. And that's the thing that you will crumble under your own weight over time, uh, absent Some external intervention. Uh, and this, you see this happen all the time, right? And it shows up and manifests in d…

AI assessment note: “And this happens in companies as well, right? Like it happens in code”

Q all these frameworks and lenses. Before we do that, you kind of hinted at this idea of how you pick what to work on. And I know you have kind of an interesting framework for how to decide what ideas are good and what ideas are worth investing in. I think both as a founder and a product leader, how do you think about deciding what is worth investing in?

A So imagine Excel spreadsheet again. So let's say you're a value and idea for a startup. For a new product, a new feature, whatever it happens to be, I think this, uh, this applies. Um, so the first thing, uh, you should look at is, and I, I measure things on a scale of zero to 10, because I like quantifiable things. I like to be able to multiply x by y. I don't like letter grades, um, pet peeve of mine. Anyway, so Put a number on it. It's like, okay, if this thing were successful, so let's say we're just picking a new startup idea. Like I'm considering starting this new business. Um, if it were successful, what could it be? What's the kind of magnitude of the outcome? However you decide, it could be impact. It could be revenue. It could be market cap. It could be portfolio, whatever it is. It doesn't matter. Um, I mean, it matters, but not relevant for this discussion. So that's the potential thing. Number two is probability of success. Okay. And now that I pause here and tell you the most common mistake people make is, um, They think through the probability first without actually forcing themselves to think through the potential. And here's what happens, is that they apply a filter that says, oh, I only have a, like, one in 10 chance to pull this off. There's only a 10% success rate or whatever. Not gonna do that. Well, if it's a one in 10%, one in 10 chance at ten billion dol…

AI assessment note: “So that's the potential thing. Number two is probability of success.”

Q uh, you tweeted that it took you many, many late nights of work. For people that want to Understand what's going on, get ahead of where things are going, build the skills to be relevant in the future. Do you have any advice? Is it just build stuff and do it? Or is there anything else you'd recommend for people that want to understand what the hell is going on?

A Yeah. So, uh, and this is very simple, um, practical advice. And it's the same thing for like, uh, engineers and software, um, as well is don't try to go learn something, uh, because you think it's like worth learning. Find an actual problem that you care about and go try to solve it with that new thing, right? Like you have something tangible that you're trying to do. So for instance, um, you know, going back to my book, back to the talk around public speaking, it's like, okay, if I had said, oh, I want to learn About humor and stand up comedy. I don't think I would have accomplished the thing, but I had a goal in mind, right? Which is like, Hey, I need to be able to get up on a stage and hold up a thing. And I have this measurable thing. So whatever it is, whatever line of business you're in, whatever you do as a professional, um, I guarantee you there are ways, uh, AI can help you even with the tools that we have out there right now. So either use the tools, build tools on top of the APIs that exist very easily accessible, um, right now, very cheap to kind of start. Um, yeah, just, just do it and iterate. And I am a big believer also in kind of learning in public as well. That's why I do it. Like, that's why the culture code is out there. It's like, okay, well, if you accept the fact that culture is a product, we're gonna learn about things much better. Like instead of just …

AI assessment note: “Find an actual problem that you care about and go try to solve it”