The Exchanges

Q intuitive people when you think about your senior leaders in the company? That you want people that have intuition for their part of the business in the way that you have intuition? Or you think that's mainly your role as a founder and you're fine if that kind of way of being doesn't show up in team leads or, or your exec team or however you want to define it?

A I'm unclear what intuition is exactly. Is it just good judgment? If so, Then yes, I want that in all my leaders. I'm not trying to be a smart ass, but you know, absolutely. Um, you want people who look, I'll tell you about my favorite type of people, my least favorite type of people, my favorite type of people who have strong opinions. Um, it's important that they can have their minds changed, but they have strong opinions. They show up and they say, We need to do X, Y, Z with our pricing. I'm sorry, we're doing it wrong. We need to do, we have a certain approach we need to take that my co-founder Kieran does this a lot, and it's inconvenient, his statements and sentiments. That is so much more useful to me than the other type of people who are like, um, well, there's clearly multiple approaches here. Um, I looked at Zoom and Slack, and also Salesforce, and they have the three different ways. And I talked to this pricing expert, and we had them do just an initial study, and they've come back with similarly about three categories. They looked at 58 different types of companies, and when we run this analysis, we see that There's pros and cons to each. That is like the professional managerial class. That's the MBA way. And that's useless in building great companies. You need people with strong opinions in my humble opinion.

AI assessment note: “If so, Then yes, I want that in all my leaders.”

Q what did coming back to the company Teach you that you maybe had gotten wrong in the first chapter. We're going to talk a little bit about the environmental factors where you had abundant capital to more scarce capital, but are there specific things that when you came back, you would have redone differently? Or you did incorrectly that with fresh eyes, new perspective made you change your mind on?

A For me personally, it, the big lessons are all about trusting my instinct and my principles. Um, Silicon Valley as a culture and a place and a community is a, is made up of a phenomenal amount of young people doing what they do for the very first time. And more specifically, it's a bunch of raw talent with no experience. And that has very predictable results in that great things are produced in a very messy way. And for me and us, a bunch of the mess actually came from Not having the requisite experience to know that our instincts about the way we wanted to run our business and what greatness looked like and people and companies was right. A lot of this raw talent I refer to, I think is constituted by young people who, for whatever reason, their intuition about the world and what greatness looks like, great software or great companies. Is actually right. And all they have is their ego to, to, uh, deliver that to the world. And so coming back, I realized things like, hey, it turns out that the employees who would constantly complain about things not related to the company are actually not a good fit and not the type of people that we need to be really successful. It turns out that raw, intense ambition And big swings and big bets rather than careful, measured, responsible moves are what excites people. Um, turns out that putting the customer first actually Um, goes a very long w…

AI assessment note: “the big lessons are all about trusting my instinct and my principles.”

Q there is magic and benefit to that, but you're getting at it at like one of the more important points, I think, which is the art of great company building is knowing which of these things is relevant for you and which is not, and certainly because most people do X does not mean that you should do X, but like, what do you make of the, that knowledge base?

A I think it's incredible. I think it's, um, And so awesome. And it, and it's one of the richest and most beautiful aspects of this thing we call Silicon Valley, which expands beyond the geography. Um, people are extraordinarily generous. The reason I said earlier that once mileage may vary is that I typically hate giving it advice. Kind of what we're doing right now is bullshit. Um, with due respect, um, because Uh, telling someone else how to run their very unique business, um, is incompatible with the idea that, um, their goal is to build, you know, a billion dollar enterprise by virtue of the fact that it's different from everything else. Those two ideas are incompatible. The, the, the, the wrong way to tap into the great resources and assets that are the things in Salkin Valley are to carte blanche take Uh, stories and pieces of advice and direction and apply them to your own business. The right way is to, um, absorb them and to build a system of understanding about the world that you certainly will need to operate within. So I may go and meet a great CEO of a hundred billion dollar business. I've had the privilege, say, of meeting Benny off a number of times. I don't imagine that his way of running his business is directly applicable to Intercom, but if I listen carefully to what he tells me about how he runs things and then make an effort to understand why, then I can enri…

AI assessment note: “I think it's incredible. I think it's, um, And so awesome.”

Q Why for you do you like that generalist sort of orientation and the ability to work on the other parts of the business?

A I think it's because I fundamentally disagree with the idea that any area is rocket science, and that there's a right way to do things absolutely and completely, um, and that the Silicon way, Silicon Valley way is the way, and that that leader must tell the CEO what to do. Like, Most heads of HR I've met are substantially inferior when it comes to the basics of what makes a good organization run than say our CTO, Dara Curran. And Dara Curran doesn't have all, maybe all the soft skills of your typical HR leader, but he runs a great organization extremely thoughtfully. He listens to people on the ground. He's sensitive to their compensation issues. Um, he's kind of a bit more of a man of the people. And so, you know, the other model for building these companies is the professional CEO way. You bring in a super experienced chief product people officer. They tell you how things should be done. They import everything from Salesforce or wherever else they were last time. And you don't have an opinion because you don't have opinions. You're a manager. You're an operator. And that creates a soulless, lifeless, disconnected, dysfunctional shit organization, in my humble opinion. There's ways to make it work, kind of. Um, and I'd much rather have an alive living, um, org that is being built on the fly by people with real opinions who want to create something great and special. There's so…

AI assessment note: “I fundamentally disagree with the idea that any area is rocket science”

Q When you decided to come and refocus the company on customer service, how did you approach what part of the market you wanted to focus on?

A Basically, we focused on the one that we're good at, you know, early stage investors talk a lot about, you know, founder market fit, or at least that's a concept I kind of have in my mind because I think it's important, you know, when founders, very young founders in their early to mid twenties talking about building enterprise products and like, You have no idea how big companies buy. You've never worked in any company. I didn't either. Um, and so for us, we, we use the same principle. You know, we know companies are size and smaller. We're passionate about, you know, that type of scale and impact. There's a ton of money to be made in enterprise, but that's not us. We don't know how to do it. Um, we'll gladly fit in underneath the people like Salesforce would do.

AI assessment note: “we focused on the one that we're good at... we know companies are size and smaller”

Q What are some examples or an example of late?

A Can I give you a counter example? I just came across today from a young founder who I think is brilliant. I won't name, and then I'll give you the counter example of where recently we re did reinvent something. Brilliant founder, very successful startup, posted that they wanted to hire a chief of staff, a growth chief of staff, and they DM'd me to say, hey, do you know anyone? And I said, um, you know, what is it that they should or intended to do? Like, who, what is this person? And I said, hey, I don't know my two cents, but if you invent a new title like this, which might make sense for the world you're building, A lot of people, you want experienced people, that's what they said, who do this job. They're not going to find this role. It's not going to describe what they do. And I, I told them, in my humble opinion, you reinventing this title for what I think is growth marketing is going to make your life really hard. And they, they're like, yeah, you're absolutely right.

AI assessment note: “Can I give you a counter example? I just came across today”