20VC: Why Most AI Investments Will Do Worse than the S&P 500 | Why Early Stage VC is F******* | The Danger of Kamala Harris and Why Trump and Vance are Best | Freedom of Speech, Censorship and Government Control with Eoghan McCabe @ Intercom

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. 10 Questions with One of the Largest Private Company CEO’s: AI Investing: Why will most AI investments not do better than the S&P 500? Building SaaS Tools with AI: Why is it crazy for companies to follow Klarna and use AI to build their own tools? 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? Early-Stage is F*******: Why is the early-stage venture ecosystem as an asset class f******? Founder Mode: Why does Eoghan believe all of the best founders are unbalanced? What is the difference between Founder vs Manager mode? Political Voice: Why did Eoghan decide he had to voice his political opinions now? The Danger of Harris: Why does Eoghan believe a Harris administration would rob the US of immense freedom, democracy and civil liberty? Why Vote Trump: Why does Eoghan believe that Trump will regain immense freedom for the sovereign individual? Freedom of Speech: How does Eoghan determine right vs wrong when freedom of speech leads to harm and injustice? 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?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

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

• 0:41Harry Stebbings?

  I mean, this show has more peri peri sauce than a Nando's extra hot chicken. This is one of the spiciest shows we've done in a while. Also, such range of discussion for a short show, AI, politics, freedom of speech. Owen McCabe, co-founder at Intercom, is incredible here. If you want to watch the full episode, you can find it on YouTube by searching for 20VC. That's two zero VC. Before we begin, I want to share something interesting about the private market. There are many ways to buy and sell private stock today, but Hive is the only platform that provides a one-stop liquidity solution for private companies and their shareholders. It not only provides access to a deep pool of investors, but also allows companies and boards to control key elements

• 1:23Harry Stebbings?

  like buyer approvals, seller eligibility, and even pricing, offering liquidity on their own terms. What's more, Hive's comprehensive transaction execution service and centralized transaction tracking allows companies to stay on top of all past, pending, and upcoming transfer requests so easily and at no cost. Visit hive.com, that's H I I V E with two I's, and see why they're the fastest growing liquidity platform in the world. Hive Markets Limited is a broker dealer and member of FINRA, SIPC. Investments in private stock are risky. Only accredited investors may buy through Hive. And just like Hive transforms liquidity, Tegus transforms how we gather insights for investing.

• 2:08Harry Stebbings?

  When I invest in software A day, I think software is valuable when it saves time and makes something easier. But when it enables the user to do something they simply could not do without it. Then it's insanely powerful and valuable. That's the case with Tegus. I literally could not live without them. When I'm investing in a company, Tegus lets me see the most incredible reference calls with experts in a space who work at a competitive company or incumbents. These calls and data provide the most incredible insight that really shapes my opinions and thoughts and investment decisions. And I can then share snippets from calls with team members. This is a tool that will change how you work. Honestly, you cannot imagine life without it. Once you've experienced how powerful it is. And you can check them out today by heading over to tegus.com.

• 2:52Harry Stebbings?

  You have now arrived at your destination. 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.

• 3:02Speaker 00

  Thank you for having me back.

• 3:03Harry Stebbings?

  Not at all, but we always start with the context. And you've been asked 10,000 fucking times how many times you founded Intercom. And so we're just gonna skip it. I wanna dive right in. We are 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? Said with love.

• 3:29Speaker 00

  I appreciate that. I mean, everyone's fucked by AI in the fullness of time. I mean.

• 3:33Harry Stebbings?

  No, that's just the title for the show, is it not? That's the intro, that's the segment.

• 3:38Speaker 00

  Unfortunately, unfortunately, I regret that already. Yeah, in the fullness of time, increasingly powerful and abstract AI will do away with all of the work we need to do today to deliver software experiences. That has always been the case with technology. There is no new technology that won't be obsolete in some period of time. And I wouldn't be working my ass off in 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, two decades.

• 4:03Harry Stebbings?

  So the conventional wisdom kind of in AI circles 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?

• 4:20Speaker 00

  You know, the reality is that adoption of new technology takes far longer than we all always imagine. 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 bitch, we now have the highest performing AI customer service 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%.

• 4:48Harry Stebbings?

  How is that, Owen? You leverage OpenAI and alternative models to drive that efficiency?

• 4:55Speaker 00

  Yeah.

• 4:55Harry Stebbings?

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

• 5:01Speaker 00

  Yeah, it's all the existing data sources with intercom. It's your historical conversations that your human reps are also having. But 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, is that 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

• 5:41Speaker 00

  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 prompt engineering massaging to make it highly effective at closing tickets. When we first released our AI agent, the average resolution rate was in the high twenties. 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 twenties. And so it just takes a long period of time and a lot of work to build all of the 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 going to win. That's why they're going to become so big,

• 6:26Speaker 00

  because I don't think, at least in the next five, 10 years, that any of the AI labs are going to build all the domain-specific stuff.

• 6:32Harry Stebbings?

  I interviewed Ethan Mollick, who's the head of ML or AI at Wharton, and he said, you cannot believe in AGI and also be a SaaS investor.

• 6:44Speaker 00

  Right.

• 6:44Harry Stebbings?

  Because if you believe in AGI, then every SaaS product will be killed, straight off.

• 6:49Speaker 00

  Yeah, I think that's right, in the fullness of time. And again, if you held on to 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 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.

• 7:16Harry Stebbings?

  Well, I asked a question, which is like, why are you not fucked by AI?

• 7:19Speaker 00

  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 pick up these technologies. And the question you asked.

• 7:29Harry Stebbings?

  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, do you think we're not actually, and that is overhyped?

• 7:45Speaker 00

  There's various aspects of it. 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 in the world. That said, even the technology community at large has not yet made contact with how valuable AI already is. There are 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 a SaaS company to reach 30 million in ARR from a specific investor who was

• 8:26Speaker 00

  picking great SaaS companies was something like four, five years. And the average time for these AI companies to reach 30 million in ARR was less than two years. AI application companies are currently blowing up in a way that people don't realize. They're currently delivering a lot of value.

• 8:41Harry Stebbings?

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

• 8:54Speaker 00

  Yeah.

• 8:54Harry Stebbings?

  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.

• 9:03Speaker 00

  Sure.

• 9:03Harry Stebbings?

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

• 9:06Speaker 00

  Of course, when anything new happens, any new trend, there's going to be so much noise. And 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 going to support a lot of excitement around AI and actually not do better than the S and P 500.

• 9:26Harry Stebbings?

  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.

• 9:33Speaker 00

  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 totally flame out. I stand by 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 the product and they're not going anywhere. They've forever changed.

• 10:06Harry Stebbings?

  Klarna announced that they were stopping their customer contracts with their work data and with service with Salesforce. 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?

• 10:23Speaker 00

  Well, I have no choice but to say that that's a terrible fucking idea. And just like Intercom is eventually fucked by AGI, we'd also be fucked by companies building their own AI systems. The reality is, hand on heart, independent of my association with Intercom. I think that building your own AI agent platforms is going to be as smart as in the previous generation, building your own SaaS workflow tools. These things are super deep. Like I said, with Finn, our AI agent, it's the product of over 100 different experiments, many patented parts. We've got 30 ML engineers and counting, 100 other engineers working on all the application components. You're just not going to build a highly performant, rich AI agent on the side. Not going to be done.

• 11:07Speaker 00

  And I think any attempt to do so may yield some short term excitement. But even Klarna, long term, I'm pretty sure will move on to a professional purpose. System.

• 11:17Harry Stebbings?

  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.

• 11:23Speaker 00

  Makes no sense.

• 11:24Harry Stebbings?

  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 three hundred X while I'm Canva, love those guys. 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?

• 11:50Speaker 00

  Technology is deflationary. Technology gets cheaper and cheaper and cheaper over time. But look at these statistics where they show the real prices of various products and goods. And even as currency inflates, the price of, say, TVs, flat screen TVs goes down. And so these AI agents will be way cheaper than humans while they're also better. That said, what you're going to see people do is augment their 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 going to start to find that if, for example, in our e-commerce story,

• 12:35Speaker 00

  these companies can generate substantially better sales through providing these epic AI assistants. They'll happily spend more money for them. But when those themselves become commodities, then it'll get cheaper over time, too.

• 12:47Harry Stebbings?

  Do you buy the reduction in team sizing that AI has? I think if you look back to the seventies, 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?

• 13:04Speaker 00

  Valuable businesses have got smaller with technology. You know, the size of Google or Facebook, when they were worth a hundred billion dollars in employee size was substantially smaller than General Electric or Ford. The long arc of technology and automation requires less humans. So it'll perpetuate that arc. You're not going to see mass layoffs at Intercom, for example. We've been using our this AI agent Finn for nearly two years and we've not let anyone go, but we've stopped growing the size of our support team. I think any future growth is going to 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.

• 13:46Speaker 00

  Now, when we hire for customer service, we're hiring a more talented, experienced person who can do the creative things that the AI agents can't. Eventually, as these teams get smaller and through attrition, the AI will be doing more and more of them and there just will be less humans in the mix.

• 14:02Harry Stebbings?

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

• 14:10Speaker 00

  If they could do it, capitalism dictates that they should.

• 14:13Harry Stebbings?

  But if they can do it, why can't you do it? Like, why can't everyone do it? There must be some loss.

• 14:19Speaker 00

  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 eighty percent, three types of questions that cover eighty percent 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.

• 14:50Harry Stebbings?

  What extent do you think foundation model layer companies, your OpenAI, your Anthropics, subsume the core application layer companies? Customer service maybe being one of them, language translation maybe being one of them. To what extent do you think that's a reality?

• 15:06Speaker 00

  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 business people. 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 going to crush all of software, they're not actual business people, 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.

• 15:44Harry Stebbings?

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

• 15:51Speaker 00

  I think we're going to see a giant rise of robotics in many different areas. A lot of blue collar work will probably be done by robotics. The one thing that's important to say while I'm 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. Whether it's individuals on factory floors where they lose limbs, humans dying in mines. So much of these 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.

• 16:34Speaker 00

  We have no reason to believe that we're not still on that same trajectory.

• 16:38Harry Stebbings?

  How do you feel about the photographer who's going to have their spend cut in half? Because we can do AI backgrounds so much easier. We can reduce spend on a photo. I literally just came from a photo shoot and I was like, dude, this is going to be mostly AI in three years. And he was like, I know.

• 16:54Speaker 00

  They'll learn new things over time. When I got into the technology industry, I was making crappy websites, writing HTML by hand. Now we have so many different ways to generate websites. You certainly have seen so much web designer work disrupted by Wix and Squarespace and Shopify and all of these tools and technologies and frameworks. 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. It's going to continue to be the case.

• 17:29Harry Stebbings?

  Something I find really challenging, Owen, is like, you know, you look at the latest YC batch. All the companies are relatively interesting AI consumer application led companies in large part. And actually, when you dig deeper, a lot of them is kind of 11 labs tagged to an OpenAI model. And it's really just bringing together different foundation model companies. And the core thing comes back to, well, there's not really that much defensibility. It's just kind of architecture stuck together. How do you feel about defensibility install ups? I know you've invested too in them.

• 17:58Speaker 00

  There is no such thing. 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 and adopt it, always been the case. And so talking about modes 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, 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

• 18:41Speaker 00

  other than the fact that they can build better and faster than anyone else. And that's okay.

• 18:45Harry Stebbings?

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

• 18:48Speaker 00

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

• 18:51Harry Stebbings?

  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 and think about it when you read it?

• 19:03Speaker 00

  I think it was really acute and fun branding for a thing that anyone who's built a company has deployed since the start of companies. 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. But business is very much an art, particularly starting a business from scratch is a deeply creative endeavor. 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 lowest common denominator and something that satisfies everyone. And so highly agentic individuals and acting on their own intuition, I think is how greatness has always been made.

• 19:46Harry Stebbings?

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

• 19:50Speaker 00

  It's in the hundreds of millions. So we'd be one of the larger private software companies.

• 19:55Harry Stebbings?

  Why don't you go public? I always hear Gurley and Brad and Altimeter and they're like, more companies need to go public when they're in this range. Yeah, the valuation will take a hit.

• 20:04Speaker 00

  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 time horizon and who actually need to operate the businesses, unlike Gurley, have different priorities. My goal is to build a giant, highly impactful, really fucking cool technology company. It means absolutely nothing to me whether or not my stock is traded on the public market or the private market.

• 20:32Harry Stebbings?

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

• 20:39Speaker 00

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

• 21:19Harry Stebbings?

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

• 21:20Speaker 00

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

• 21:32Harry Stebbings?

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

• 21:36Speaker 00

  The right investors want value long term and they know that in these moments of great change, that the best value will be created behind closed doors. 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.

• 21:54Harry Stebbings?

  I am an investor though. Like, we need liquidity. And M and A, what you're going to do with Dylan and go through 18 months of hell and then get blocked? No, you're probably going to 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?

• 22:13Speaker 00

  There will be IPOs, there will be liquidity, maybe on private markets, M and A will warm up again. There's a lot of money in PE. It'll have to unstick itself, 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? And we are by far not the only company of that tenure. So the game has changed.

• 22:42Harry Stebbings?

  Do you think the VC model still works?

• 22:45Speaker 00

  The amount of capital at an early stage available today suggests to me that that's got to be a crappy end of the market for VCs. It's just a raw commodity now, early stage VC. I don't know how you make a return there.

• 22:59Harry Stebbings?

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

• 23:10Speaker 00

  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. That was a really, really, really, really big mistake. Our total customer count started to shrink. That's one example. Others were we're pricing, we got greedy, we wanted people to sign big contracts upfront rather than allow them to expand into them. So it was just going against all our intuition, bad commercialization. That was the main thing. Do we want to talk about the internal changes at Intercom, about restarting the startup and the culture? Companies are this deeply interconnected system.

• 23:52Speaker 00

  You know, you can't change one thing without changing another. You can't pick and choose. It's not an à la carte menu. It's a deeply interconnected system. We needed to totally change our values, make clear that hard work and a focus on our mission was key, was crucial. I gave permission to people to act in quick and scrappy and messy ways. I rolled up my sleeves and gone involved myself. I set this project called Project 52, where I gave us 52 weeks to reinvent the company. 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

• 24:32Speaker 00

  fit with the new values I wrote and the values were things like hard work and resilience and a focus on our mission were respectfully moved out.

• 24:38Harry Stebbings?

  I always struggle with this, like the values of like hard work and resilience. I mean it in the nicest way. No one disagrees with them. One of our values is unreasonably hard work. I expect you to cancel your friend's dinner to continue working when you have a project. 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.

• 25:00Speaker 00

  Sure.

• 25:00Harry Stebbings?

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

• 25:04Speaker 00

  Is that true?

• 25:05Harry Stebbings?

  Yeah.

• 25:06Speaker 00

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

• 25:07Harry Stebbings?

  I I think so.

• 25:08Speaker 00

  Many, many employees are against truly hard work. Don't you think so? Have you not met lazy people? Why do you have your value?

• 25:17Harry Stebbings?

  Oh, no, no, there are people who don't work very hard, but it doesn't mean that they're like, I disagree with it. They know they're lazy.

• 25:25Speaker 00

  There was kind of a meme that started 10 years ago where people would say work smart and not hard. Started to promote ideas like work, life balance. And I think that that's great. There's no objectively right or wrong way to live your life. But if you're trying to do something insanely difficult, it will just require a lot of energy and focus. There are people out there who think that there are smarter ways to work, that maybe four days a week is better than five. Or maybe some version of work, life balance is more productive. I think that that's false. Really fucking hard work cannot be beat.

• 26:01Harry Stebbings?

  Did people push back on that?

• 26:02Speaker 00

  Yeah, and on all the things, of course they did, yeah. But they were wrong for the company and that's totally okay. I guess they pushed back on some of the tops down way of working, you know? I would dictate values, I would dictate policies. The way a professional CEO runs an organization is by consensus. So imagine they want to feel out an opportunity to bring people back to the office. They'll go and they'll poll leaders and staff on their opinions. And if it's not popular, they won't do it. And so they're stuck in stasis and mediocrity. The way a highly agentic, enabled founder who will not apologize does that is simply tell people, we're going to be two days in the office. This is for a good reason. If you're not into it, God bless. Certain people are allergic to that way of working.

• 26:44Speaker 00

  They want to be part of the communist consensus approach. And that's not where greatness comes from.

• 26:51Harry Stebbings?

  How many days a week are you in the office?

• 26:53Speaker 00

  We only mandate two days a week. I think on average it's something like three. If I started all again, I would definitely do five days a week. I think just being a person is just far superior, so much more fun.

• 27:04Harry Stebbings?

  It's a divisive topic. Another divisive topic is politics. And you have leaned in to political commentary on social support. To start off, why did you decide to lean in on expressing your political views?

• 27:19Speaker 00

  Because it's important for humanity. I'm a big believer in individual liberty and peace. We're in a time where both of those are being threatened. Western establishments, Western governments are impinging upon a lot of individual liberties, whether it's freedom of speech, freedom to 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 between nuclear powers. And I think that that's 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. I have always been deeply apathetic about political games, but this time is different.

• 27:57Harry Stebbings?

  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?

• 28:10Speaker 00

  Yeah, like I'm pro-freedom. I will vote for and support and donate to the person who promotes the most freedom. I have no team, no tribe. At the moment, it's crystal clear that Trump and fans are the people who are promoting the most personal liberties and freedoms. They are not the ones who are wanting to shut down speech or to shut down crypto or to try and ban 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. Really obvious, patently clear the solution or the person that needs to get voted for. Very few people I talk to in technology who are not voting Trump at the moment, very, very few.

• 28:54Speaker 00

  There are some people who are either triggered by Trump, but most people have decided that that's the side that is going to support liberty and peace.

• 29:01Harry Stebbings?

  Do they admit it publicly?

• 29:03Speaker 00

  Of course not. Why would they be so foolish? It's totally okay. I am not going to judge people for making decisions about what they want to 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 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 protect humanity and peace in the world.

• 29:27Harry Stebbings?

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

• 29:33Speaker 00

  It's an effective, practical solution. I introduced that years ago also, and we do not talk about politics in Intercom, and I never do that within the company either. For me, it's also important that 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 important that I demonstrate these principles in those moments. I will defend them. And it's important, I think, that the CEO exercises and demonstrates their alignment with these policies. And so similarly, I'm going to be myself. I'm going to represent the things I believe in.

• 30:14Speaker 00

  Again, particularly when they're aligned with things that are designed to better humanity and peace in the world.

• 30:20Harry Stebbings?

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

• 30:24Speaker 00

  No, I'm a really, really big believer in authenticity. 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 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 going to work with me because you're not willing to accept my individual beliefs and support my efforts to better humanity and find peace in the world, then we're not a good fit for each other. I've heard of no problems with customers. I've heard nothing from the board or investors.

• 31:03Speaker 00

  If you stay close to the moral high ground, 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'll find that the masses will be very supportive, and really I've had no problems whatsoever by my openness.

• 31:20Harry Stebbings?

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

• 31:25Speaker 00

  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, things like that. So I never was cool with DEI, but you know, publicly, I didn't speak out about it. There was a point in the Bay Area where 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

• 32:09Speaker 00

  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.

• 32:22Harry Stebbings?

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

• 32:25Speaker 00

  I think it's totally fucked that we try and censor people. The institutions and the big tech companies are still censoring people. It's evil, really, really evil.

• 32:37Harry Stebbings?

  Evil or rational? Just put, I always like to do a short, a different case, which is like, "Okay, everyone has a boss, okay? I have a boss as an investor, they're 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."

• 32:54Speaker 00

  Yeah, I think companies are very different from like the wider world and the public forums. 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.

• 33:11Harry Stebbings?

  What happens when freedom of speech is fake news?

• 33:13Speaker 00

  Um, who gets to decide what fake news is?

• 33:16Harry Stebbings?

  Elon Musk posting a picture about Vinod Khosla's beach with-

• 33:20Speaker 00

  People make mistakes.

• 33:21Harry Stebbings?

  With no plebs allowed. He knew it wasn't fucking no plebs allowed. Of course he did.

• 33:25Speaker 00

  Jokes are, jokes are protected by freedom of speech. And if Elon repeatedly does that, his reputation should take a hit. No greater power 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, 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.

• 33:50Harry Stebbings?

  Jokes are protected by freedom of speech. So if I say a joke and it's egregiously false misinformation has massively

• 33:59Speaker 00

  Absolutely. 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 because it's fucking true.

• 34:13Harry Stebbings?

  No, then I could just blast anything out as a fucking joke.

• 34:17Speaker 00

  Yeah. 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 mistake. It's very purposeful massaging of truth for various certain interests.

• 34:35Harry Stebbings?

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

• 34:41Speaker 00

  The kind of hard and fast rule in the United States is you can't yell fire in a crowded theater. 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 threshold there. That's no longer speech. That's kind of conspiracy to cause harm and inflict damage on a person. So I don't think you could say that that should be protected.

• 35:09Harry Stebbings?

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

• 35:13Speaker 00

  Absolutely. Are you crazy? You 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.

• 35:34Harry Stebbings?

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

• 35:37Speaker 00

  Who makes the rules, my friend?

• 35:38Harry Stebbings?

  Maybe I'm just getting so infected by Europeanism, but like I could

• 35:42Speaker 00

  You are.

• 35:43Harry Stebbings?

  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 fuck ton of hatred, but it's a joke.

• 36:03Speaker 00

  Then you should be shamed, you should be criticized, 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 cannot decide what's right or wrong or 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, the freedom to say what you want comes at risks. 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.

• 36:47Speaker 00

  The government works for us. They are our employees. Their job is to protect us, not shut us down and shut down our freedom.

• 36:55Harry Stebbings?

  The truth is, I don't think I've ever felt like I had freedom.

• 36:58Speaker 00

  I think that this part of a UK thing, I think when there's a monarch. And I think when you live under generational experiences of being a serf and people of a kingdom, then you do tend to feel less freedom. The people who came to the new world in 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.

• 37:24Harry Stebbings?

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

• 37:31Speaker 00

  That's a problem and that's because of the institutions, the culture, big tech. You're saying, you're speaking to a problem that is happening today. And it would be made far worse if we let governments shut down things like jokes.

• 37:43Harry Stebbings?

  Do you think Trump will win or do you accept that Kamala has now?

• 37:46Speaker 00

  No fucking clue, no clue.

• 37:48Harry Stebbings?

  Who do you think won the election or won the stage last night, JD or Tim Walz?

• 37:52Speaker 00

  Vance did an outstanding job. I think he was like, he did a good job of being calm, collected, smart, empathetic, thoughtful communicator.

• 38:02Harry Stebbings?

  In the refounding of Intercom, how have you most significantly changed as a CEO? It kind of feels like you've found yourself.

• 38:09Speaker 00

  It's true, you know, when I left, I left chiefly because I was sick. Also because revenue started to slow, also because I was attacked in the press. And I was like spiritually crushed, physically crushed, psychologically crushed. That process, you know.

• 38:24Harry Stebbings?

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

• 38:28Speaker 00

  Not good things, versions of like, am I a fucking loser? Like, I fucked up. And in doing so, when you go through a process like that, your ego is eviscerated. Your identity as whatever perfect little image that your ego wanted to create for yourself is by necessity 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. All these ideas of perfection can't possibly be held to be true anymore because they've been proven otherwise. So when I came back to Entercom, yeah, I felt so much more myself. That's just helped me speak my mind, be authentic and real with people, create and curate the culture and environment that I believe will be successful and do so making

• 39:11Speaker 00

  no apologies and being okay with people being upset by it.

• 39:14Harry Stebbings?

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

• 39:20Speaker 00

  I have a lot to prove still. I'm still just a boy who was bullied in school and is trying to find love and validation. 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, deeply at one with the universe, who then says, I think I'll start a technology company. That doesn't exactly happen. Most people that start companies, they have so much to prove, big chips on their shoulder. To get to your question, if there's anything I'm ashamed of, it's that, I'm still trying to prove myself. That's what tends to give us our edge and that's what creates artists. And I think the secret is not in fighting that, but learning to love that. And I've learned to love that.

• 40:01Harry Stebbings?

  Final one before we do a quick fire. SF is known for its productivity, benefits your career. You've got the new club.

• 40:09Speaker 00

  Yeah.

• 40:10Harry Stebbings?

  Why you did it? Let's start there.

• 40:12Speaker 00

  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. It can be incredibly boring. Everywhere shuts at 10 or 11, people go to bed on time. Really great place to be productive, great place to balance your nervous system in these stressful endeavors, getting out to nature. 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.

• 40:52Speaker 00

  These American and Western values are under threat, but they're actually supported by the vast majority of people. 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 who love freedom and all these other values. We got 3.7 thousand people on the waitlists.

• 41:36Speaker 00

  We invited 600 people. It's really apparent that the vast majority of people want fun and they want freedom.

• 41:42Harry Stebbings?

  I I saw the pictures online. They're fucking awesome. So well done for that, dude.

• 41:46Speaker 00

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

• 41:50Harry Stebbings?

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

• 41:56Speaker 00

  Sounds wonderful.

• 41:57Harry Stebbings?

  What do you believe that most around you disbelieve, Owen?

• 41:59Speaker 00

  That nuclear holocaust is super possible.

• 42:02Harry Stebbings?

  Well, I'm not just gonna move on post that one, am I? Like, can you unpack that for me?

• 42:06Speaker 00

  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.

• 42:27Harry Stebbings?

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

• 42:29Speaker 00

  No idea. Looks bad.

• 42:31Harry Stebbings?

  What book written before 1965 would you most recommend?

• 42:35Speaker 00

  The only one that comes to mind is 1984. There's a theme in this whole conversation, forgive me.

• 42:39Harry Stebbings?

  Do you like freedom, Owen? Side of thing for you. Tell me, what blog post written post 2000 is your favorite?

• 42:45Speaker 00

  I listen to interviews by smart people. I just want to listen to conversations by as many smart people as possible. That's why I love podcasts.

• 42:53Harry Stebbings?

  Who, when you see their name, are you like, ooh, I want to listen?

• 42:57Speaker 00

  Wow, it's great. Because we're talking about, you know, national security and whatnot, I think Eric Prince is fascinating. He's the former Blackwater guy, Eric Prince.

• 43:06Harry Stebbings?

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

• 43:09Speaker 00

  The LLMs are gonna eat software. I don't think that's gonna happen anytime soon.

• 43:15Harry Stebbings?

  Who's your favorite VC?

• 43:16Speaker 00

  Apart from Harry Stebbings.

• 43:18Harry Stebbings?

  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?

• 43:25Speaker 00

  If I was raising a series A or B, I really like Ilya Fushman at Kleiner Perkins. I think he's just got good intuition and he's just chill. 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. Maybe it'd be Ilya.

• 43:40Harry Stebbings?

  Mamoun's one of my favorites, one of the best of the best. Okay, final one for you. What question are you not often asked that you think you should be asked more?

• 43:50Speaker 00

  What is great leadership? And it's only because I have a firm and a hard, if not a cheesy answer, and that's by being truly yourself. 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.

• 44:09Harry Stebbings?

  Dude, I love having you on because you actually get honesty and you don't get the veneer of corporate. I so appreciate this. As always, you've been wonderful to have on.

• 44:19Speaker 00

  I appreciate it too. Thank you for having me, Harry. Really appreciate it.

• 44:23Harry Stebbings?

  My word, that was so much fun, Stu. I love it when it's a natural discussion. You can watch the full interview by searching for 20VC on YouTube. That's two zero V C, where you'll be able to find it easily to see the full discussion in video. Now, before I leave you, let me share one more exciting development from Hive. It's called Hive 50, and it's like the first live index of large-cap private securities generated directly by customer orders and transactions on the platform. Over 70% of US-based Decacorns have traded on Hive, and the Hive 50 ranks the 50 most liquid securities in its marketplace, based on transaction volume and liquidity. And even better, the index is equally weighted to the top 50 stocks, effectively acting as a barometer for the market's direction.

• 45:07Harry Stebbings?

  And momentum in private tech company investments. Go check it out at hive.com/hive50. That's hive with two I's dot com slash hive50. To see how they're shaping the future of private market investing. Hive Markets Limited is a broker dealer and member of FINRA SIPC. Investments in private stocks are risky. Only accredited investors may buy through Hive. And just like Hive transforms liquidity, Tegus transforms how we gather insights for investing. When I invest in software today, I think software is valuable when it saves time and makes something easier. But when it enables the user to do something they simply could not do without it. Then it's insanely powerful and valuable. That's the case with Tegus. I literally could not live without them.

• 45:52Harry Stebbings?

  When I'm investing in a company, Tegus lets me see the most incredible reference calls with experts in a space who work at a competitive company or incumbents. These calls and data provide the most incredible insight that really shapes my opinions and thoughts and investment decisions. And I can then share snippets from calls with team members. This is a tool that will change how you work. Honestly, you cannot imagine life without it. Once you've experienced how powerful it is. And you can check them out today by heading over to tegus.com. As always, I so appreciate all your support and stay tuned for one of the best 20 VC venture investor episodes we've ever done, coming on Monday with the one and only David Frankel at Founder Collective.