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Eoghan McCabe, CEO @Intercom: Freedom of Speech, Censorship and Government Control | E1213

Eoghan McCabe is the Co-Founder and CEO @ Intercom, one of the largest private software companies in the valley with hundreds of millions in revenue and thousands of customers. To date, Eoghan has raised over $238M from Index, Kleiner Perkins, ICONIQ, GV, Bessemer and more incredible firms. Intercom’s goal is to reinvent customer service with AI agents replacing human agents over the next 10 years. ----------------------------------------------- Timestamps: (00:00) Intro (02:09) AI in Customer Support: Intercom's Role in the Emerging Landscape (05:59) Overestimating AI (09:07) SaaS Future: Companies Building Their Own Tools? (10:35) AI Costs: Rising Prices or Falling Expenses? (17:19) AI Startups: True Innovation or Just Thin Layers on Models (21:02) Why Intercom Doesn’t Go Public (24:16) Does the VC Model Still Work? (25:43) Shifting from SMB to Mid-Market (26:48) Hard Work vs. Work-Life Balance (30:10) Why Eoghan Expresses His Political Views Publicly? (35:32) Reflecting on Leadership (37:43) Freedom of Speech vs. Fake News (43:11) How Eoghan Has Changed as CEO (45:33) Launching San Francisco Freedom Club (47:48) Quick-Fire Round ----------------------------------------------- 10 Questions with One of the Largest Private Company CEO’s: 1. AI Investing: Why will most AI investments not do better than the S&P 500? 2. Building SaaS Tools with AI: Why is it crazy for companies to follow Klarna and use AI to build their own tools? 3. Going Public: Why is Bill Gurley wrong that more later stage companies should go public? Why did Intercom shelve plans to go public in 2022? 4. Early-Stage is F****:** Why is the early-stage venture ecosystem as an asset class f******? 5. Founder Mode: Why does Eoghan believe all of the best founders are unbalanced? What is the difference between Founder vs Manager mode? 6. Political Voice: Why did Eoghan decide he had to voice his political opinions now? 7. The Danger of Harris: Why does Eoghan believe a Harris administration would rob the US of immense freedom, democracy and civil liberty? 8. Why Vote Trump: Why does Eoghan believe that Trump will regain immense freedom for the sovereign individual? 9. Freedom of Speech: How does Eoghan determine right vs wrong when freedom of speech leads to harm and injustice? 10. Middle East and Nuclear War: Why does Eoghan believe that nuclear war is much closer than we think? Will we see the Middle East descend into war? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Eoghan McCabe on Twitter: https://twitter.com/eoghan Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #eoghanmccabe #intercom #ai #remotework #venturecapital #founder #ceo #trump

Eoghan McCabeguestHarry Stebbingshost
Oct 11, 202450mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:09

    Intro

    1. EM

      Most VC money is gonna support a lot of excitement around AI and actually not do better than the S&P 500. I think that building your own AI agent platforms is gonna be as smart as, in a previous generation, building your own SaaS workflow tools. That's a terrible fucking idea. I'm a big believer in individual liberty and peace, and we're in a time where both of those are being threatened. It's crystal clear that Trump and Vance are the people who are promoting the most personal liberties and freedoms. And I think it's deeply evil to decide what can or cannot be spoken about. Governments become insanely and dangerously powerful when their citizens cannot say what they believe is true or not.

    2. HS

      Ready to go? Owen, I am so excited for this, dude. I always remember our last show. It's one of my favorites that we've done. So, thank you so much for joining me today, man.

    3. EM

      Thank you for having me back.

    4. HS

      Not at all. But we always start with the context, and you've been asked it 10,000 fucking times how many times you founded Intercom (laughs) .

    5. EM

      (laughs)

    6. HS

      And so, we're just gonna skip it. I wanna dive right in.

    7. EM

      Please.

    8. HS

      We are, bluntly, in a very interesting time of AI and a lot of people are saying that customer service is the most impacted and will be removed. With Intercom's position, why are you not fucked by AI? (laughs) Said with love.

    9. EM

      Yeah. I appreciate that. I mean, um, e- everyone's fucked by AI in the fullness of time, right?

    10. HS

      (laughs)

    11. EM

      I mean, you know, as, as a, as a... Go on.

    12. HS

      No, that's just the title for the show, is it not? (laughs) I think that's the intro, that's the segment.

    13. EM

      Un- unfortunately. Unfortunately.

    14. HS

      (laughs)

    15. EM

      I regret that already. Yeah, in the fullness of time, increasingly powerful and abstract AI will do away with, you know, all of the work we need to do today to deliver softer experiences. That has always been the case with technology. There's no new technology that won't be obsolete in some period of time, and I wouldn't be working my ass off at Intercom if I thought that it was about to die and be crushed by AI in a year or two. So, I think we've got a decade,

  2. 2:09 – 5:59

    AI in Customer Support: Intercom's Role in the Emerging Landscape

    1. EM

      two decades.

    2. HS

      So, the conventional wisdom, kind of, in AI cycles now is that, actually, customer service and customer support is the low-hanging fruit, and that's gonna be picked off in the next year or two. What position does Intercom play in that landscape moving forwards? Or do you disagree, that is not the timeframe and it will be a decade plus?

    3. EM

      You know, the reality is that adoption of new technology takes far longer than we all- always imagine. You know, we built... We were the first to come out with an AI agent that would do customer support for you, like actual conversations with customers and closing tickets. We now have... Forgive the fucking pitch. We now have the highest performing AI customer service, uh, bot. You look at everything that's on the market, they can't resolve tickets at the rate we can. The average resolution rate of our bot is now approaching 50%.

    4. HS

      Can you just help me understand that? How, how, how is that, Owen? Y- you leverage OpenAI and alternative models to drive-

    5. EM

      Yeah.

    6. HS

      ... that efficiency?

    7. EM

      Yeah.

    8. HS

      What... 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?

    9. EM

      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 (sighs) how the AI is gonna develop, and we can come 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 100 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 and 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 20s, high of 20%. So, that's the rate at which it successfully closes tickets when it gets involved in a conversation. And now, like I said, it's approaching 50%. I think Zendesk is still high 20s. 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, really great at these domain-specific things. That's why these AI application companies are gonna win. That's why they're gonna become so big, because I don't think, at least in the next five, 10 years, that any of the AI labs are gonna build all the domain s- specific stuff.

    10. HS

      I interviewed Ethan Mollick, who's the head of ML or AI-

    11. EM

      Hmm.

    12. HS

      ... at, um, Wharton, and he said, "You cannot believe in AGI and also be a SaaS investor."

    13. EM

      Right. That's right.

    14. HS

      Because if you do, if you believe in AGI, eh, then ev- every SaaS product will be killed. Straight off.

    15. EM

      Yeah. I think that's right, in the fullness of time. Um, and again, you know, if you held onto your stock in fax companies, you'd be crushed. But for the first 10 years, you would have made a fucking fortune. So, in technology it's all about timing, and it's all about, you know, um, waving successive growth cycles and riding the trends in that moment in time. And then you must reinvent yourself and kill yourself. You asked an interesting question at the start, and we've already forgotten what it is.

    16. HS

      Well, I- I asked a question-

    17. EM

      Um-

    18. HS

      ... which is like, why are you not fucked by AI?

    19. EM

      Yeah. Yeah, exactly. And, and that's the answer. It's because, sure, AGI crushes all of software in the fullness of time, but it takes a really long period of time to, um, pick up these technologies.

  3. 5:59 – 9:07

    Overestimating AI

    1. EM

    2. HS

      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 esca- re- reaching a sc-... Do you think we're not, actually, and that is over-hyped?

    3. EM

      I think that, to my previous point...... the rate at which AI is gonna 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 valuable AI already is. There are maybe 100, 200, 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 30 million in ARR, 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 30 million in ARR 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.

    4. HS

      This is my hardest thing as an investor though, which is like, you know, determining sugar high revenues versus actually long, enduring, sustainable revenues. 'Cause you're absolutely right. I invest for a living day-to-day. I see 10 million ARR the whole freaking time from AI companies.

    5. EM

      Yeah.

    6. HS

      Before that would, in 18 months, have been the gold standard. My challenge is the quality of revenue is much lower. Often their POCs are pilots, if they're enterprise at all.

    7. EM

      Sure.

    8. HS

      It's the most exciting time to be investing and it's also the most challenging.

    9. EM

      Yeah. Uh, of course when anything new happens, um, any new trend, there's gonna be so much noise. And, um, it's your job to be one of the few investors who can spot the signal in the noise and beat the market. Most VC money is gonna support a lot of excitement around AI and actually not do better than the S&P 500.

    10. HS

      There's a brilliant stat which is, like, in the two years following the founding of Netscape, only 1% of internet enterprise value was created.

    11. EM

      Hmm. Yeah. Now, they were the very early days and still this has to be the very early days of AI. And there will be a lot of AI companies that f- totally flame out. But, uh, I stand by the f- the, the assertion that there are AI companies delivering really tangible value. And the things you pointed to are exactly right. Usage and retention is how you spot the difference. So there is definitely a lot of revenue that's driven by just excitement, people kicking tires. But there are AI businesses out there where they retain customers, those customers have totally changed the way they've worked, they're expanding on their product, um, they're not going anywhere. They've forever changed.

  4. 9:07 – 10:35

    SaaS Future: Companies Building Their Own Tools?

    1. EM

    2. HS

      Klarna announced that they were stopping their partnerships or, you know, customer, yeah, contracts with, uh, Workday and with Service, with Salesforce, um, and it led to this wave of, "Wow, this is the future. Companies will build their own SaaS tools." I'm interested, how do you feel about that and how do you respond to that question and concern?

    3. EM

      I have no choice but to say that that's a terrible fucking idea. Uh, just like Intercom is eventually fucked by AGI, we'd also be fucked by companies building their own AI systems. The reality is, uh, hand on heart, independent of my association with Intercom, um, I think that building your own AI agent platforms is gonna be as smart as, in a previous generation, building your own SaaS workflow tools. These things are super deep. Like I said, with Fin, our AI agent, it's the product of over 100 different experiments, many patented parts. We've got 30 ML engineers and counting, you know, 100 other engineers working on all the application components. Um, you're just not gonna build a highly performant, rich AI agent on the side. Not gonna be done. And I think any attempt to do so may yield some short-term excitement, but, uh, even Klarna long term, I'm pretty sure it will move on to a professional purpose-built system.

    4. HS

      I, I completely agree. I think it's one of the most ridiculous misnomers in the valley right now that everyone will build their own individual tools.

  5. 10:35 – 17:19

    AI Costs: Rising Prices or Falling Expenses?

    1. HS

    2. EM

      Makes some sense.

    3. HS

      Um, there's two worlds. One whereby it continues to cost a lot of money to provide such great high quality AI products and you do a Canva and increase pricing by 300X.

    4. EM

      (laughs)

    5. HS

      Um, well done Canva. Love those guys.

    6. EM

      Yeah.

    7. HS

      Uh, or, actually, we see costs go way down as they have done so far, and actually pricing remains relatively stable, but it's the cost that really reduces. What world do you think is more likely and why?

    8. EM

      Technology is deflationary. Technology gets cheaper and cheaper and cheaper over time. You look at, look at these statistics where they show the real prices of various products and goods, and even as, um, uh, currency inflates, uh, the price of, say, TVs, flat screen TVs goes down. Um, and so, um, these AI agents will be way cheaper than humans while they're also better. That said, what you're gonna see people do is augment their, uh, the savings they make in their budgets or use the savings they make in their human budgets to spend on as much AI as they can until they're now totally over-serving their customer. I think people are gonna start to find that if, for example, in our e-commerce, um, uh, story, uh, these companies can generate substantially better sales through providing these epic AI assistants, they'll happily spend mo- more money for them. But when those themselves become commodities, then it'll get cheaper over time too.

    9. HS

      Do you buy the reduction in team sizing that AI has? I think if you look back to the '70s people would say, "God, if we had computers that did all these things we wouldn't need anyone here." Yet there are still companies with hundreds of thousands of people. How do you feel about the reductive nature of AI on team size?

    10. EM

      Viable businesses have got smaller with technology. You know, the size of Google or Facebook when they were worth $100 billion in employee size was, was substantially smaller than, um, you know, General Ele- Electric or Ford. So, the, the long arc of technology and, um, automation requires less humans, so it'll perpetuate that arc. You're not gonna see mass layoffs. At Intercom, for example, we've been using our, this AI agent, Fin, for nearly two years and we've not let anyone go, but we've stopped growing the size of our support team.

    11. HS

      Mm-hmm.

    12. EM

      And so I think any future growth is gonna be catered to by the AI agents. The AI agents will first do a lot of low-level and simpler work, and the humans will do the higher level work. Now when we hire for customer service, we're hiring a more talented experienced person who can do the creative things that the, the AI agents can't. Eventually, as these teams get smaller and through attrition, um, the AI will be doing more and more of them and there just will be less humans in the mix.

    13. HS

      I am asking a spicy one here. Is Seb wrong then to fire 700 people in Klarna's customer service team?

    14. EM

      If they could do it, um, you know, capitalism dictates that they should-

    15. HS

      But if they can do it-

    16. EM

      ... serve their shareholders.

    17. HS

      ... why can't you do it? Like, why can't-

    18. EM

      I-

    19. HS

      ... everyone do it? There must be-

    20. EM

      I think s-

    21. HS

      ... some loss.

    22. EM

      Certain use cases where the distribution of the types of questions is really tight, rather than this big, long normal distribution of so many different types of questions, will be able to create these tight custom experiences. If you're a Klarna, for example, you might only get three questions that cover 80%, three types of questions that cover 80% of your inbound. And therefore, you can actually create AI or AI-ish experiences to do big swaths of your customer service. Most businesses are not like that.

    23. HS

      To what extent do you think foundation model layer companies; your OpenaIs, your Anthropics-

    24. EM

      Oh.

    25. HS

      ... subsume the core application layer companies, customer service maybe being one of them, uh, language translation maybe being one of them, to what extent do you think that's a reality?

    26. EM

      Again, in the fullness of time, if they manage to become ever closer to something we call AGI, they will. Storytellers and visionaries are very different from builders and businesspeople. These are just different types of disciplines and different individuals, and so the people that tell these big visionary stories about how LLM companies or AGI is gonna crush all of software, they're not actual businesspeople, they're not actual builders, and they don't realize that businesses, consumers have real practical problems that need solving, and it takes them a really, really long time to adopt these technologies.

    27. HS

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

    28. EM

      I think we're gonna 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-

    29. HS

      How, how do you feel about photo-

    30. EM

      ... put people out of work and make humanity better.

  6. 17:19 – 21:02

    AI Startups: True Innovation or Just Thin Layers on Models

    1. EM

      But actually these people were never put out of work. The demand, the greater demand that these people could not serve was catered to, and those people got more specialized. That's gonna continue to be the case.

    2. HS

      Something I find really challenging, Eoghan, is like, you know, you look at the latest YC batch and all the companies are relatively interesting AI consumer application layer companies in large part. And actually when you dig deeper a lot of them is kind of ElevenLabs tagged to an OpenAI model and it's really just bringing together different foundation model companies, and, uh, the core thing comes back to, "Well, there's not really that much defensibility, it's just kind of-"

    3. EM

      Yeah.

    4. HS

      "... architecture stuck together." To what extent is that a moot point and that's how great companies are built in the start? And to what extent is it, no, these are very, very thin layers and you should actually be concerned about that?

    5. EM

      I think that what's important is the people involved. You're absolutely right. Great things have small beginnings.Um, and if you looked at Intercom back in the day, how was that defensible? It was like a little crappy crud app. It had a database of users and you could send some messages to someone's website. Anyone could build it. Um, but the people involved were particularly talented, um, I'm talking about my teammates and not me, but I wasn't terrible either. And, you know, one thing-

    6. HS

      Who was your favorite teammate? (laughs)

    7. EM

      ... led to another. I have to say Des, I have to say Des, but they're all wonderful. They're all wonderful.

    8. HS

      (laughs) No, I, I, I totally get you. How do you feel about defensibility in startups? I know you've invested too

    9. NA

      Yeah.

    10. EM

      There is no such thing. Yeah, there's no such thing. Even Apple don't have it. Apple very famously championed their patented iPhone technologies, and yet Samsung came and actually beat them on many different criteria. Technology is a cat and mouse game. It's about who builds it first and brings it to market, helps customers understand it and adopt it. It's always been the case. And so talking about moats is kind of silly. Now that said, some of the greatest technology companies of our generation then go on to build networks and other things that do become defensible, whether it's Apple's iMessages, or their ecosystem, um, whether it's Google's data, whether it's Facebook's network. At some point, you can build some degree of defensibility, but software companies and technology companies in particular, they don't tend to have any defensibility other than the fact that they can build better and faster than anyone else, and that's okay.

    11. HS

      Is speed the single most important thing in going from zero to one?

    12. EM

      It's one of them. Working your ass off, working very hard.

    13. HS

      Can I ask you, if we think about Silicon Valley central casting, PG's essay on Founder Mode went incredibly viral, obviously in the last month. How did you feel a- and think about it when you read it?

    14. EM

      I think it, it was really, like, a cute and fun branding for a, uh, a thing that anyone who's built a company has deployed since the start of companies. Um, that, you know, there's nothing new about it. There's countless books about Steve Jobs and how he operated. Maybe it gives permission now to founders to trust their gut and instinct, which I think is a really, really good thing. Um, but business is very much an art, particularly starting a business from scratch, um, is a deeply creative endeavor. And, uh, the worst type of art is art produced by committee. I would say it's just not art if you're trying to find the c- lowest common denominator and something that satisfies everyone. And so, um, highly agentic, um, uh, individuals, and acting on their own intuition, I think is how greatness has always been made.

    15. HS

      Can I ask you, how, how m- I don't know if it's public, but, like, how much do you guys do in revenue today?

    16. EM

      It's in the hundreds of millions.

    17. HS

      In the hundreds of millions?

    18. EM

      Yeah. Yeah. So we'd be one of the larger private software companies.

  7. 21:02 – 24:16

    Why Intercom Doesn’t Go Public

    1. EM

    2. HS

      Why don't you go public? I was with Gurley and, you know, Brad at Altimeter, and they're like, "More companies need to go public when they're in this range. Yeah, the valuation will take a hit."

    3. EM

      Yeah. I mean, of course a VC would say go public. You know, these VCs need liquidity. Founders who have a different mission and a longer, uh, uh, uh, time horizon, and who actually need to operate the businesses, unlike Gurley, um, have different priorities. My goal is to build a giant, highly impactful, really fucking cool, um, technology company. It means absolutely nothing to me whether or not my stock is traded on the public market or the private market. And the reality is today-

    4. HS

      And you don't think it would be better for you in terms of, uh, rigor, accountability, all the reasons that they say?

    5. EM

      They're the things that the analysts want. They're the things that the investors want. I want a shit ton of customers, a shit ton of revenue. I want a really impactful organization. I wanna have a really, really, uh, big, um, amount of influence on technology at large. I don't need all of the regulatory compliance to do any of that. All the regul- regulatory compliance gets in the way of that. But the reason that people take public companies private during crazy moments like this, post-COVID and now post-AI, is so that they can make really big swings and big bets, uh, without all of the rigmarole of being public. We nearly went public in 2022, and I'm so grateful that we did not.

    6. HS

      Talk to me about that. I didn't know that.

    7. EM

      Yeah. 2022, I think it was, uh, June 15, we had a stock ticker that I hated, but nothing cool was available. We had written our S1, and the markets collapsed. We were not the only ones.

    8. HS

      How did people respond? Investors get excited, liquidity coming.

    9. EM

      The right investors want value long term and they know that in these moments of great change that the best value will be created, um, behind closed doors. And so, you know, we can talk about it if we want, want to, but, um, all the big swings and changes I made at Intercom that has dramatically accelerated our revenue growth, I don't think I could have made that if I was a public company CEO.

    10. HS

      I am an investor though. Like, we need liquidity-

    11. EM

      Sure.

    12. HS

      ... and M&A, what you're gonna do a Dylan and go through 18 months of hell and then get blocked. No, you're probably gonna do a Whiz and just say, "No thanks," at the start. And then IPOs, I'm with you on everything you just said. So what happens then? We just have this extended private window?

    13. EM

      There will be, there will be IPOs. There will be liquidity, maybe in private markets. M&A will warm up again. There's a lot of money in PE. It'll have to unstick itself. Um, but admittedly, we're currently in an awkward patch where a lot of people are asking themselves, "Does this VC model even make sense?" I mean, Intercom is a 13-year-old company. When people were investing in Intercom, they thought maybe they'd get liquidity in, what, eight years? So, and we are by far not the only company of, of, of, of that tenure. So, uh, the game has changed.

  8. 24:16 – 25:43

    Does the VC Model Still Work?

    1. EM

    2. HS

      Do you think the VC model still works?

    3. EM

      I'm not a VC, so I can't fonda- I can't really comment on that. One thing I will say is the amount of...... capital at a early stage, uh, available today suggests to me that, um, that's gotta be a crappy end of the market for VCs. I mean, it's just a raw commodity now, early-stage VC. I don't know how you make a return there.

    4. HS

      You mentioned the revenue there and kind of the, the seismic shifts that you've d- made to kind of cause the changes. Why did revenue plateau, growth plateau? What happened?

    5. EM

      We forced more and more customers to talk to sales. It certainly increased ACVs, but it actually cut out a phenomenal amount of growth in SMBs and small customers, and those small customers were actually the lifeblood for our sales customers. They just needed some time to grow. Um, and so, um, that was a really, really, really, really big mistake. Our total customer count started to shrink. It's now growing very rapidly again after the changes I made, but it started to shrink. That's one example. Others were our pricing. We got greedy. We wanted people to sign big contracts up front rather than allow them to expand into them. So, it was just going against all our intuition. Bad commercialization, that was the main thing.

    6. HS

      What percent is SMB versus enterprise today?

    7. EM

      Uh, uh, we don't do a lot of enterprise. SMB is a large part, but we're increasingly moving into mid-market.

  9. 25:43 – 26:48

    Shifting from SMB to Mid-Market

    1. EM

    2. HS

      What was the hardest thing about making the shift?

    3. EM

      It, it was a lot of internal change. Do, do we wanna talk about the internal changes at Intercom, about restarting the startup and-

    4. HS

      Yeah.

    5. EM

      ... the culture?

    6. HS

      Yeah.

    7. EM

      I mean, companies are this deeply interconnected system. We needed to totally change our values and, uh, make clear that hard work and a focus on our mission was key, was crucial. I picked a lane rather than doing all the things. These big companies just started to d- started, start to do all the things, and I said, "No, we're doing customer service." Um, I gave permission to people to act in quick and scrappy and messy ways. Uh, I rolled up my sleeves and got involved myself. I set this project called Project 52 where I gave us 52 weeks to reinvent the company. I spoke to the company every single week. I just created this very high degree of intensity. I rolled out these new performance management processes where people who didn't fit with the new values I wrote, and the values were things like hard work and resilience and a focus on our mission,

  10. 26:48 – 30:10

    Hard Work vs. Work-Life Balance

    1. EM

      were respectfully moved out, and the people who were aligned with them were promoted, given big salary increases. So it was just a-

    2. HS

      Can I, can I, can I-

    3. EM

      Yeah.

    4. HS

      Owen-

    5. EM

      Yeah.

    6. HS

      ... I always struggle-

    7. EM

      Yeah.

    8. HS

      ... with this. Like, the values of, like, hard work and resilience. I mean-

    9. EM

      Yeah.

    10. HS

      ... it in the nicest way. No one disagrees with them. So, like, you know, uh, one of our values is unreasonably hard work.

    11. EM

      Yeah.

    12. HS

      I expect you to cancel your friend's dinner to continue working when you have a project.

    13. EM

      Uh-huh.

    14. HS

      People will say, "No, that's wrong and you should have that balance." I say, "That's fine. You should have another job somewhere else."

    15. EM

      Sure.

    16. HS

      But you should be for or against them. No one's against, like, hard work and resilience.

    17. EM

      Is that true?

    18. HS

      Yeah.

    19. EM

      Is that true that no one's against hard work?

    20. HS

      I, I, I think so.

    21. EM

      Many, many employees are against truly hard work.

    22. HS

      (laughs)

    23. EM

      Don't you think so? Have you not met lazy people? Like, why do you have your value?

    24. HS

      Oh, no, no. There, there are, there are people who don't work very hard.

    25. EM

      That's right.

    26. HS

      But it doesn't mean that they're like, "I disagree with it."

    27. EM

      Uh, I, I think that's not true-

    28. HS

      But they know they're lazy.

    29. EM

      ... actually.

    30. HS

      They know they're lazy. They know they're undisciplined-

  11. 30:10 – 35:32

    Why Eoghan Expresses His Political Views Publicly?

    1. EM

    2. HS

      It's a divisive topic. Another divisive topic is politics (laughs) , Owen.

    3. EM

      Sure.

    4. HS

      And you have leaned in to political kind of commentary on social support. Just start off-Why did you decide to lean in on expressing your political views?

    5. EM

      Um, just because it's important for humanity. Uh, you know, I'm, I'm, I'm a big believer in individual liberty and peace, and we're in a time where both of those are being threatened. Um, you know, Western establishments, Western governments are impinging upon a lot of indi- individual liberties, whether it's freedom of speech, start and run certain types of businesses. They don't like crypto, they don't like AI, and they're starting a lot of wars, um, between nuclear powers, and I think that that's, uh, just really, really, really, really, really fucking dangerous. That's the only reason I'm in any way involved. I hate politics. I tend to dislike politicians. Um, I have always been deeply apathetic about political games, but this time is different.

    6. HS

      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?

    7. EM

      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 ban AI, or do a range of other things that are just gonna 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 gonna support liberty and peace the most.

    8. HS

      Do they admit it publicly?

    9. EM

      Of course not. Why would they be so foolish? It's totally okay, um... I, I, I'm not gonna judge people for making decisions about, uh, what they wanna involve themselves in. I just think it's really important that people speak publicly. If it's a thing that we're afraid to speak about, then, uh, everything gets worse. I think it's inappropriate to hate on people and criticize them for choices they make, particularly when the choices are designed to, um, protect humanity and peace in the world.

    10. HS

      So, how do you feel about Bryan Armstrong's, you know, famous piece about politics not having a place in the workspace?

    11. EM

      I think it's a, it's a effective, practical solution. I introduced that years ago, also. And we do not talk about politics in Intercom, and, uh, I never do that, uh, wi- uh, within the company, either. For me, it's also important that, um, Intercom never tells employees what to do in their personal lives. I'll never tell employees what they can or cannot say, and if any employee is ever attacked for their political positions online, especially and particularly if they're positions that I disagree with, it's im- it's important that I, um, demonstrate the, these principles in those moments. Um, I, I will de- I will defend them, um, and, uh, it's important, I think, that the CEO, uh, exercises and demonstrates, um, uh, their alignment with these policies. And so similarly, I'm gonna be myself. I'm gonna represent the things I believe in, again, particularly when they're aligned with, you know, things that are designed to better humanity and peace in the world.

    12. HS

      Did you worry about turning off potential talent from applying or joining?

    13. EM

      No. I'm a really, really big believer in, um, authenticity. I think great leadership is all about being who you truly are. If you're completely open, honest, and vulnerable, then people can opt in and out accordingly. Because of the values I instituted and the performance management processes I followed, um, to curate a certain set of people in the company, we're now really resilient. There was literally one person who left, and if you're not gonna work with me because you're not willing to, um, accept my individual beliefs and, um, uh, support my efforts to better humanity and find peace in the world, then we're not a good fit for each other. Um, but I've heard of no problems with customers. I've heard nothing from the board or investors. If you stay close to the moral high ground and you communicate the reasons you do what you do, and you stay strong, don't apologize or flinch when the tiny minority of people come after you, you also, you'll find that the masses will be very supportive. And really, I've had no problems whatsoever by my, uh,

  12. 35:32 – 37:43

    Reflecting on Leadership

    1. EM

      openness.

    2. HS

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

    3. EM

      You know, maybe during the DEI days. I, I never really promoted DEI. I always thought it was a really bad idea to, uh, discriminate against people for their race or their gender, 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.... who are 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.

    4. HS

      What have we not moved on from that is totally fucked?

    5. EM

      I think it's totally fucked that we try and censor people. Um, the institutions and the big tech, uh, companies are still censoring people. Um, it's evil, really, really evil. Um, you know, um, but-

    6. HS

      Evil or rational? Just, just put, um ... I always like to see a sure, uh- uh, different case, which is like, okay, everyone has a boss, okay? I have a boss as an investor, then my LPs. No. If you are in my companies, you cannot say what you want because it could offend one of our LPs, and they pay your rent.

    7. EM

      Yeah, I think companies are very different from, like, the wi- the wider world and the public forums. Um, I think it's deeply evil to decide what can or cannot be spoken about. It's really dangerous. It's the hallmark of totalitarianism, and it has always signaled far worse things.

  13. 37:43 – 43:11

    Freedom of Speech vs. Fake News

    1. EM

    2. HS

      What happens when freedom of speech is fake news?

    3. EM

      Who gets to decide what fake news is?

    4. HS

      Elon Musk posting a picture about Vinod Khosla's beach with, "No plebs-"

    5. EM

      People make mistakes.

    6. HS

      ... with, "No plebs allowed." He knew it wasn't fucking no plebs allowed. Of course he didn't. He knew, isn't it?

    7. EM

      Jokes are, jokes are protected by freedom of speech. And if Elon repeatedly does that, his reputation should take a hit. Um, but no greater power, um, should ever be trusted, and it's proven that they can't be trusted, for example, during the COVID times, to decide what is or is not fake news or right or wrong or appropriate. That's very dangerous. And there's a v- ... And I know you're playing devil's advocate right now, but there's very, very few people that agree that that's a good idea.

    8. HS

      Jokes are protected by freedom of speech.

    9. EM

      Fuck yeah, they are.

    10. HS

      So if I say a joke, and it's egregiously false misinformation that has massively-

    11. EM

      Abso-fucking-lutely.

    12. HS

      That shit's fucked.

    13. EM

      'Cause who gets to decide? During COVID, it turned out that these gene therapies were really bad for you and that these traditional treatments were really, really helpful. Don't slap your face like I shouldn't have said that 'cause it's fucking true. But that-

    14. HS

      (laughs) No, dude. It's just like, uh, then I can just blast, uh, anything out as a fucking joke.

    15. EM

      Yeah, yeah, but ... Yes, you can and you should, and that's the power and magic and beauty of freedom of speech. No one gets to decide what is or isn't appropriate or true. And people frequently make mistakes, and often it's worse than a mistake. It's, um, very purposeful massaging of truth for various certain interests.

    16. HS

      What if a joke has massively damaging consequences to people, physically, mentally?

    17. EM

      Hard and fast rule in the United States is you can't yell fire in a crowded theater. And if your quote unquote joke causes egregious harm to someone, maybe your joke, I don't know, it doxes someone and it tells people, "Go and attack a certain person at a certain address," you've passed the, um, the threshold there. That's no longer speech. That's kinda conspiracy to cause harm and, and inflict damage on a person. So, I don't think you could, um, say that that should be protected.

    18. HS

      I'm so fascinated. So basically, we should be able just to say anything?

    19. EM

      Abso-fucking-lutely. Are you crazy? You'd think that a higher power should tell you, the sovereign individual, the beautiful human that is Harry, what opinions you can and cannot have. Governments become insanely and dangerously powerful when their citizens cannot say what they believe is true or not.

    20. HS

      No, but I think we should actually have rules. Again, God, and maybe I'm just getting st-

    21. EM

      Who makes the rules, my friend?

    22. HS

      Wa- Uh, and maybe I'm just getting so infected by Europeanism, but like-

    23. EM

      You are. (laughs)

    24. HS

      ... I could mock a, uh, a situation where, you know, a w- 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 'cause it's a joke. And guess what? I will put it in the right forums at the right time and incite a fuck-ton of hatred, but it's a joke.

    25. EM

      Then you should be shamed. You should be criticized. Um, and 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 is 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 risks. But we are born sovereign and free. And for us to be a- 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.

    26. HS

      The truth is, I don't think I've ever felt like I've had freedom. That's why this feels so alien to me. Like, I think-

    27. EM

      I think that there's part of a UK thing. I think when there's a monarch, and I think when you live under generational experiences of being, um, um, you know, a serf and, uh, a people of a kingdom, then you do tend to feel less freedom. But people who came-

    28. HS

      But-

    29. EM

      ... to the New World and the United States, by definition, are people who decided that they didn't want that and they separated themselves from it. So Europeans, people in the UK and Ireland, they don't feel that same level of freedom.

    30. HS

      But everything from DEI to them being afraid to say about Trump, like, I, I don't feel any freedom to say anything around that.

  14. 43:11 – 45:33

    How Eoghan Has Changed as CEO

    1. EM

    2. HS

      In the re-founding of Intercom, how have you most significantly changed as a CEO? It kinda feels like you've found yourself.

    3. EM

      Yeah. It's, it, it, it's true, you know. I, um, when I left, I left chiefly because I was sick, also because revenue started to slow, always, also because I was attacked in the press, and I was like spiritually crushed, physically crushed, um, psychologically crushed. That process, you know, kind of-

    4. HS

      What did you tell yourself when you had all of that shit happening?

    5. EM

      Not good things. V- Versions of like, "Am I a fucking loser?" Like, "I fucked up." In doing so, when you go through a process like that, your ego is eviscerated. Your identity as whatever, um, perfect little image that your ego wanted to create for yourself is, by necessity, you know, uh, burned. And so when you go through these processes but then manage to survive it, what comes out the other side is a far more authentic person. You know, all these ideas of perfection can't possibly be held to be true anymore, 'cause they've been proven otherwise. So when I came back to Intercom, yeah, I felt s- so much more myself. That's just helped me speak my mind, uh, be authentic and real with people, create and curate the culture and environment that I believe will be successful, and do so making no apologies and being okay with people being upset by it.

    6. HS

      What trait do you have that you're slightly ashamed of, but you think has contributed to your success?

    7. EM

      T- You know, I have a lot to prove still, you know. I, um, I'm still just a boy who was bullied in school and is trying to find love and validation. Um, you know, tends to be the case for all founders. I've never met a founder that's really well-balanced. You can't possibly imagine someone who is grounded and centered, part of a loving community, um, deeply at one with the universe who then says, "I think I'll start a technology company." Most people that start companies, they have so much to prove, big chips on their shoulder. And so, to get to your question, if there's anything I'm ashamed of, it's that. I'm still trying to prove myself. Um, but, you know, that's what tends to give us our edge and that's what creates artists and, you know, I think the secret is not in fighting that but learning to love that, and I've learned to love that.

  15. 45:33 – 47:48

    Launching San Francisco Freedom Club

    1. HS

      Final one before we do a quick fire.

    2. EM

      Yeah.

    3. HS

      SF is known for its productivity, for-

    4. EM

      Yeah.

    5. HS

      ... its, uh, benefits to your career. Um, how, uh, uh ... You've got the new club.

    6. EM

      Yeah.

    7. HS

      Talk to me about that, why you did it, thoughts around it.

    8. EM

      Yeah. Well, I'll start with the SF commentary and where you framed it. SF is just a really, really, really, really fucking great place to get work done, and it can be incredibly boring. Everywhere shuts at 10:00 or 11:00. Um, people go to bed on time. Um, again, really great place to be productive, great place to balance your nervous system and the stressful endeavors, getting out to nature. But it's, it's not a place for sensuality and sexuality and excitement and connection. And so, in part, I wanted to change that a little bit. But I wanted to do so under the guise of my mission to promote freedom and individual liberties, and things like merit and capitalism and growth and humanity. These American or Western values are under threat, but they're actually supported by the vast majority of people. Um, people are so afraid to speak publicly about their support for such things. They're afraid that they'll be looked at as being the bad ones, that there's something wrong with them, that they're not cool, that they're not sexy. I believed that was untrue, and so I felt like if I could get the masses wanting to be involved in a very fucking sexy, popular, fun thing, I could prove that these things were exactly those things. The San Francisco Freedom Club is designed to hold only epic parties four times a year for people to love freedom and all these other values. We got 3.7 thousand people on the waitlists. We invited 600 people. 500 showed up. Um, it's really apparent that the vast majority of people want fun and they want freedom.

    9. HS

      I saw the pictures online. Uh, they're fucking awesome, so well done for that, dude. Uh-

    10. EM

      Please, please come to the next one. It's in December. If we could get you there, that'd be outstanding.

    11. HS

      That

  16. 47:48 – 50:40

    Quick-Fire Round

    1. HS

      would be fun. But listen, I wanna do a quick fire. So, I say a short statement, you give me your immediate thoughts. Does that sound okay?

    2. EM

      Sounds wonderful.

    3. HS

      Okay. What do you believe that most around you disbelieve, Eoghan?

    4. EM

      That nuclear holocaust is super possible.

    5. HS

      Well, I'm not just gonna move on post that one, am I? Like ... (laughs) what, can you unpack that for me? Like-

    6. EM

      Yeah. I mean, the United States and Russia have many thousands of nukes pointed at each other, ready to go, and the United States is fighting a proxy war with Russia. It's super easy for these things to tumble into nuclear war. And if nuclear war happens, five billion people on the planet die. Read Nuclear War Scenario, brand new book, harrowing book.

    7. HS

      Do you think we'll see the Middle East erupt into a ...

    8. EM

      No idea.

    9. HS

      Mm.

    10. EM

      Looks bad.

    11. HS

      Mm. What book written before 1965 would you most recommend?

    12. EM

      The only one that comes to mind is Nineteen Eighty-Four. There's a theme in this whole conversation. Forgive me.

    13. HS

      Tell me, what blog post written post-2000 is your favorite?

    14. EM

      I listen to interviews by smart people. I just wanna listen to conversations by as many smart people as possible.

    15. HS

      Mm-hmm.

    16. EM

      That's why I love podcasts.

    17. HS

      Who, when you see their name, are you like, "Ooh, I wanna listen"?

    18. EM

      Uh, I mean, because we're talking about, you know, national security and whatnot, I think Erik Prince is fascinating.

    19. HS

      Huh.

    20. EM

      He's the former Black, uh, Blackwater guy, Erik Prince.

    21. HS

      Tell me, what have you changed your mind on most in the last 12 months?

    22. EM

      That LLMs are gonna, you know, eat software. I don't think that's gonna happen anytime soon.

    23. HS

      Who's your favorite VC?

    24. EM

      Apart from Harry Stabing ...

    25. HS

      If you were starting a new company, this is a different question, if you were starting a new company today, who would you take your first check from?

    26. EM

      Eoghan McCabe. But if I was raising a Series A or B, you know, I really like Ilya Fleshman at, um, Kleiner Perkins. I think he's just got, you know, good, good intuition, and he's just chill. And he, he, he doesn't, um, he's, he's ju- he's just a natural. I really love Mamoun, who he works with also. Me and Mamoun have history. He invested in our Series A.

    27. HS

      Mamoun's one of my favorites.

    28. EM

      Yeah.

    29. HS

      One of the best of the best. Uh, okay, final one for you. What question are you not often asked that you think you should be asked more?

    30. EM

      What is great leadership? And, and it's only because I have a, uh, a firm and a hard, if not a cheesy answer, and that's by being truly yourself. I, I know very few leaders, even the most celebrated leaders today, that are truly authentic. But the closer you can get to being yourself, the more powerful leader you'll be.

Episode duration: 50:50

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