The Exchanges

Q It's been my whole adult life, as you kindly suggested about my youth. But like for you, especially, you know, you were CEO of Intercom for many years, and then making a transition to chairman today, obviously you're not as operationally involved as you are as CEO, daily, daily, grinding, 24 hours a day. Was there a challenge for you in kind of detaching your identity from individual and company?

A Of course. These identities that we build for ourselves, this armor, these images, they're our place of comfort and safety, and we latch onto them. They're everything to us. We've worked so hard because we believe that they are the Everything we need, that they are us. We believe it so strongly that we will answer questions by saying things like, oh, I'm a founder, I'm a tech guy, I am a VC, and you're not. You're so much more than that. You're Harry, and that's a big risk and a big danger just getting stuck on to and associated with these images that then become limiting. Imagine what else you could do with your life. I'm not hating on VC. I think you're going to make a wonderful venture capitalist, and I think you're going to have a lot of fun doing it. But you can also do so many more things. You are so much more than that. There have been so many VCs in the world. What else could you become? Maybe you can become truly your own thing. Maybe you can become something truly unique. But if for the rest of your life or for as long as you say, I am a VC, then that's all you're going to be. So for me, absolutely. Yes. When I thought I was a CEO, I was trapped by that. Even though I knew I had so many more things I wanted to do with my life and ways I want to invest my energy and Different missions and adventures, and I had known that for years. It was a long process to be able to s…

AI assessment note: “When I thought I was a CEO, I was trapped by that.”

Q some investors of yours. And then from our, of course, the godfather of SaaS, Jason Lemkin. So starting with one from Andy McLaughlin at SoftTech, uh, an angel in Intercom. He says you mentioned, uh, previous entrepreneurial endeavors there prior to Intercom. What were your big lessons learned from those journeys other than the extreme passion that one has to have for the endeavor that they're doing at the moment?

A Yeah, that's a good question. I mean, I think a lot of the, a lot of our deepest learnings or lessons learned came, uh, through our consulting experience. With consulting, you're, uh, like I said, exposed to so many different types of businesses, different types of people, different approaches, different markets, different go-to-market strategies. And you need these number of different perspectives to kind of, like, get a good feel for what it is the thing you're looking at is. Um, you know, if you think of how you might assess an object, think of a cube. If you have just one view of a cube, you might think it's a square. If you added another perspective, a 90 degree view, you'd see another square. If you maybe added another perspective, I don't know, a 30 degree perspective, you might get the hint that it's a cube. If you, like, you know, move up another 30, 30 degrees in the Z axis. Now you really know it's a cube, you know, so you need these few different views, different perspectives, uh, different takes on the same thing to really get a sense of holistically what it is that you're dealing with. And so in our consulting experience, cause we got to look at so many different forms of business and leaders and whatnot, I think that we ended up with a pretty wholesome set of values and principles that we could apply to all businesses and especially in including intercom. So it w…

AI assessment note: “a lot of our deepest learnings or lessons learned came, uh, through our consulting experience.”

Q And then post-funding, I'm really intrigued, kind of, there was the term sheet in the kind of onboarding for investors. Post-term sheet in the Uh, following the investment, you've now seen several rounds. What does good investors look like to you now?

A You know what? The best investors, they've very quickly switched to being partners who are very much in the trenches with you and who now own your problems. The best investors say, okay, you've got my money now. That's irreversible. Hopefully this all works out, but we know that there's a lot that's really broken. Let's, uh, all try and figure it out together. The worst investors are Try and say, Hey, you've set these expectations. There is a certain timeframe. There's a certain way that things should be done. There's a certain way that we want you to work. Here's some milestones. Here's some criteria you want to meet. Um, they're the very worst investors and all those constraints and that pressure is so incredibly damaging to creative people. Great founders are deeply creative in so many different ways. So again, The best investors are partners, and they immediately jump to the other side of the table and say, okay, we really hope this works, but let's not take it for granted. We know lots of shit's broken. We're in this together, so what do we need to do? And the worst investors say, right, patience, get to work. Here's what you need to do. So it's like a true partnership.

AI assessment note: “The best investors, they've very quickly switched to being partners who are very much in the trenches”

Q Just help me understand. I'm, I don't actually understand. Is it the existing data sources that you have which allow you to do that better?

A Yeah, it's all the existing data sources with intercom, it's your historical conversations that your human reps are also having. What's really interesting and what's key to understanding how AI is going to develop, and we can go back to your questions if I manage to remember it, is that, um, building domain-specific AI systems requires a phenomenal amount of work on top of these LLMs. Of course, yes, over a decade or two, the LLMs will get powerful enough that they will disrupt away all of these Detailed intricacies that we've built, but Finn, our AI agent, for example, is the product of over a hundred unique experiments to figure out how exactly to understand customer questions and resolve tickets. There's patented components to it. I think there are somewhere around seven different LLMs intricately connected together. There's homegrown AI and just a lot of very detailed Um, prompt engineering, massaging to make it, um, highly effective at closing tickets. When we first released our AI agent, the average resolution rate was in the high twenties to high 20%. So that's the rate at which it successfully closes tickets when it gets involved in the conversation. And now, like I said, it's approaching 50%. I think Zendesk is still high twenties. And so it just takes a long period of time and a lot of work to build all of the Um, functionality on top of the LLMs to make them really, …

AI assessment note: “Yeah, it's all the existing data sources with intercom, it's your historical conversations”

Q Do you think that we are overestimating technological advancements in AI? I mean, people are now thinking that actually with scaling laws and with, bluntly, the amount that incumbents are spending, we could actually get there so much quicker than we ever thought, and we are reaching a scale. Do you think we're not actually, and that is overhyped?

A I think that, to my previous point, The rate at which AI is going to change the whole world is a little overhyped. You know, the raw technologies will be built long before they have real impact on the world. That said, I think that the Even the technology community at large is not make, has not yet made contact with how viable AI already is. There are maybe 102 hundred, maybe there are 500 companies globally that have built AI first products that are blowing up. I saw some statistic that showed that the average time it took for Um, a SaaS company to reach thirty million in AR or, um, from a specific investor who was picking great SaaS companies was something like, was it four, four years, four or five years? And the average time for these AI companies to reach thirty million in AR or was less than two years. Um, AI application companies are currently blowing up in a way that people don't realize. They're currently delivering a lot of value.

AI assessment note: “The rate at which AI is going to change the whole world is a little overhyped.”

Q Can I ask you, what do you believe will happen in the next 10 years that currently today is considered crazy or nuts?

A I think we're going to see a giant rise of robotics, um, in many different areas. Um, I, I think that a lot of blue collar work will probably be done by robotics. The one thing that's important to say, uh, while I'm kind of celebrating this human work being done is that technology has always put humans out of work when the work has been dangerous shit. And demeaning. Like, whether it's, um, individuals on factory floors, where they lose limbs, humans dying in mines. So much of these, uh, types of work that humans fucking hated, that actually killed them, has been replaced by technology. And all the while, the population of the world has increased, GDP has increased, longevity has increased. So, We have no reason to believe that we're not still on that same trajectory, um, and that we will put people out of work and make humanity better.

AI assessment note: “I think we're going to see a giant rise of robotics”

Q Why then be pro-Trump? I'm naive. I'm a naive Brit. But talking about his impact on democracy, his ability to impact Supreme Court participation and attendance, why be pro-Trump?

A Again, I'm, I'm pro-freedom. I will vote for and support and donate to the person who promotes the most freedom and most personal liberties. I have no team, no tribe. At the moment, it's crystal clear that Trump and Vance are the people who are promoting the most personal liberties and freedoms. They're not the ones who are wanting to shut down speech or to, um, uh, shut down crypto or to try and buy an AI or do a range of other things that are just going to be straight up bad for society in the world. And they're the ones who want us out of these wars. Um, so it's, uh, really obvious, really, uh, patently clear the solution or the person that needs to get voted for. And, um, And that's why, that's why everyone I talk to, it's very few people I talk to in technology who are not voting Trump at the moment. Very, very few. There are some people who are either triggered by Trump or they're, um, they don't actually study a lot of these topics, but most people have decided that that's the side that is going to support liberty and peace the most.

AI assessment note: “Trump and Vance are the people who are promoting the most personal liberties and freedoms.”

Q infected by Europeanism, but like, I could mark a, a situation where, you know, a black person or a white person or a Muslim, you choose your race, is getting beaten in the street by 10 others, and it's completely staged because it's a joke, and guess what? I will put it in the right forums at the right time and incite a fuckton of hatred. But it's a joke.

A Then you should be shamed. You should be criticized. Um, people should stop following you. I think that that's really, really inappropriate. That's not a cool thing to do. But the powers that be, um, cannot decide what's right or wrong and what's a joke. Cause then they can just decide that various things that they don't like as a joke. Look, all freedom comes at danger. The freedom to own a knife. The freedom to drive a car, um, the freedom to say what you want comes at risk. But we are born sovereign and free, and for us to be able to live our own beautiful lives and create and love who we want, build companies, we need and deserve full freedom. And it's never been government's job to take that from us. The government works for us. They are our employees. Their job is to protect us, not shut us down and shut down our freedom.

AI assessment note: “Then you should be shamed. You should be criticized.”

Q Do you think that we are overestimating technological advancements in AI? I mean, people are now thinking that actually with scaling laws and with, bluntly, the amount that incumbents are spending, we could actually get there so much quicker than we ever thought, and we are reaching a scale. Do you think we're not actually, and that is overhyped?

A I think that, to my previous point, The rate at which AI is going to change the whole world is a little overhyped. You know, the raw technologies will be built long before they have real impact on the world. That said, I think that the Even the technology community at large is not make, has not yet made contact with how viable AI already is. There are maybe 102 hundred, maybe there are 500 companies globally that have built AI first products that are blowing up. I saw some statistic that showed that the average time it took for Um, a SaaS company to reach thirty million in AR or, um, from a specific investor who was picking great SaaS companies was something like, was it four, four years, four or five years? And the average time for these AI companies to reach thirty million in AR or was less than two years. Um, AI application companies are currently blowing up in a way that people don't realize. They're currently delivering a lot of value.

AI assessment note: “The rate at which AI is going to change the whole world is a little overhyped.”

Q You said about authenticity and leadership there. When were you inauthentic to yourself as a leader, do you think? Over the years.

A You know, maybe during the DEI days, I, I never really promoted DEI. I always thought it was a really bad idea to discriminate against people for their race or their gender or things like that. So I never was cool with DEI, but you know, publicly I didn't speak out about it. Uh, there was a point in the Bay area where, um, minority candidates were thrown around like poker chips. Like it was really gross. I would go into meetings with recruiters, and they would say, good news, we've got a minority candidate. And I'm like, that is the fucking most disgusting thing you could say about that person. You didn't care to mention what company they worked with, what their achievements are, just that they're black. The most egregiously disgusting way to treat a person. So that used to happen, but that doesn't happen anymore here. So I think we've moved on a little bit from it, thankfully. We're a lot more sober, but I think in conventional industries, and maybe in conventional cultures, and I think London and New York are a little more like that. There might be a little bit of it still, but thankfully we're waking up.

AI assessment note: “maybe during the DEI days... publicly I didn't speak out about it.”

Q It's interesting for me to hear just in terms of, we always hear about the importance of focus in our industry and how focus drives success. How do you combine focus and generalization as a CEO?

A A wonderful question. You know, I think you, another part of the job and part of the challenge of business and, uh, scaling and grow and growing and operating organizations is the, Practice of applied prioritization and resource allocation. And, uh, focus can also be described as like what you give your resources. Your resources could be time, money, other things. And so, uh, you know, you need to be proficient in a lot of different things, and that's very different from the idea that you need to like very carefully prioritize all your resources, your personal resources, like what do I put my time into, and then the resources of the company. And prioritization is more a process and practice of saying no than it is saying yes. Uh, you will always have more things than you could do than you can do. And especially successful businesses, they come across these wonderful ideas and opportunities. I mean, every other week, for example, I get an email from company, founder, or a VC saying, hey, here's a company that you could buy. You know, they're a perfect fit for intercom. They're excited about intercom. They're probably quite affordable. And it's just straight up a fucking great idea. It would be a great idea. And yet it's just not something that we could prioritize right now. So we have to say no. And that's just one example of all the little opportunities that you get. So it's a,…

AI assessment note: “you need to be proficient in a lot of different things, and that's very different”

Q Why then be pro-Trump? I'm naive. I'm a naive Brit. But talking about his impact on democracy, his ability to impact Supreme Court participation and attendance, why be pro-Trump?

A Again, I'm, I'm pro-freedom. I will vote for and support and donate to the person who promotes the most freedom and most personal liberties. I have no team, no tribe. At the moment, it's crystal clear that Trump and Vance are the people who are promoting the most personal liberties and freedoms. They're not the ones who are wanting to shut down speech or to, um, uh, shut down crypto or to try and buy an AI or do a range of other things that are just going to be straight up bad for society in the world. And they're the ones who want us out of these wars. Um, so it's, uh, really obvious, really, uh, patently clear the solution or the person that needs to get voted for. And, um, And that's why, that's why everyone I talk to, it's very few people I talk to in technology who are not voting Trump at the moment. Very, very few. There are some people who are either triggered by Trump or they're, um, they don't actually study a lot of these topics, but most people have decided that that's the side that is going to support liberty and peace the most.

AI assessment note: “Trump and Vance are the people who are promoting the most personal liberties and freedoms.”

Q Not happening, boys. When is that balance between audacious, ambitious, great, and like, well, guys, too much, too soon?

A The answer is in the outcome. Those who had the big ambitions and pulled it off, well, it turns out that they weren't thinking too big. Those that did and didn't, they were. I don't think there's any answer, but I don't think the scale of their ambition was the problem. I think it was their ability to meet that and to execute. And here's the deal. I've never come across someone who I thought they were thinking Usually people I think are thinking too big. I just don't think they're a good fit for business or for entrepreneurship or for whatever endeavor they were embarking upon. It was the wrong thing for them. They'd be brilliant at something else. But the very fact that they were unconvincing in their narrative, I think is just more indicative of the fact that they're just disconnected from reality. Does that make any sense? It's not that anyone thinks too big. It's that some people think wrong. But what I'm saying is within the spectrum and scope of people who are smart and capable and creative, And we'll make great entrepreneurs or creatives within the scope of those very fortunate, lucky people. They tend to still think too small.

AI assessment note: “The answer is in the outcome. Those who had the big ambitions and pulled it off”

Q some investors of yours. And then from our, of course, the godfather of SaaS, Jason Lemkin. So starting with one from Andy McLaughlin at SoftTech, uh, an angel in Intercom. He says you mentioned, uh, previous entrepreneurial endeavors there prior to Intercom. What were your big lessons learned from those journeys other than the extreme passion that one has to have for the endeavor that they're doing at the moment?

A Yeah, that's a good question. I mean, I think a lot of the, a lot of our deepest learnings or lessons learned came, uh, through our consulting experience. With consulting, you're, uh, like I said, exposed to so many different types of businesses, different types of people, different approaches, different markets, different go-to-market strategies. And you need these number of different perspectives to kind of, like, get a good feel for what it is the thing you're looking at is. Um, you know, if you think of how you might assess an object, think of a cube. If you have just one view of a cube, you might think it's a square. If you added another perspective, a 90 degree view, you'd see another square. If you maybe added another perspective, I don't know, a 30 degree perspective, you might get the hint that it's a cube. If you, like, you know, move up another 30, 30 degrees in the Z axis. Now you really know it's a cube, you know, so you need these few different views, different perspectives, uh, different takes on the same thing to really get a sense of holistically what it is that you're dealing with. And so in our consulting experience, cause we got to look at so many different forms of business and leaders and whatnot, I think that we ended up with a pretty wholesome set of values and principles that we could apply to all businesses and especially in including intercom. So it w…

AI assessment note: “a lot of our deepest learnings or lessons learned came, uh, through our consulting experience.”

Q You said about authenticity and leadership there. When were you inauthentic to yourself as a leader, do you think? Over the years.

A You know, maybe during the DEI days, I, I never really promoted DEI. I always thought it was a really bad idea to discriminate against people for their race or their gender or things like that. So I never was cool with DEI, but you know, publicly I didn't speak out about it. Uh, there was a point in the Bay area where, um, minority candidates were thrown around like poker chips. Like it was really gross. I would go into meetings with recruiters, and they would say, good news, we've got a minority candidate. And I'm like, that is the fucking most disgusting thing you could say about that person. You didn't care to mention what company they worked with, what their achievements are, just that they're black. The most egregiously disgusting way to treat a person. So that used to happen, but that doesn't happen anymore here. So I think we've moved on a little bit from it, thankfully. We're a lot more sober, but I think in conventional industries, and maybe in conventional cultures, and I think London and New York are a little more like that. There might be a little bit of it still, but thankfully we're waking up.

AI assessment note: “publicly I didn't speak out about it”

Q Thank you so much. Life is suddenly a little bit busier, but I do want to kick off with some context. And so for those that missed our first episode, how did you make your way from Ireland into the world of startups and come to plan one of the Valley's greats in the last decade with Intercom?

A A story like so many others. Young boy has big dreams, chip on his shoulder, sets out to prove himself. I don't know if there's a lot more to it than that. I was always passionate about building and creating and so excited about the promise of the internet for creativity and connection and commerce. And with Intercom, I saw an opportunity to help online businesses just more easily and effectively connect with their customers and have a lot more fun doing it too. So it was what Intercom was all about originally and still is today. Our mission was to make internet business personal. And we made this little messenger and then bots that let these online companies and their customers really get to know each other and get their work done.

AI assessment note: “Young boy has big dreams, chip on his shoulder, sets out to prove himself.”