Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Will Systems of Record Become Valueless Databases in an Agentic World | Will LLMs Own the Value in the Application Layer with Eran Zinman About this episode Monday has been hit harder than almost any other public SaaS company. With $1.3BN in ARR, the company is valued at just $3.8BN; a more than 60% fall since IPO. Today, Eran Zinman, Monday's CEO joins Harry Stebbings in the hotseat to walkthrough six of the biggest threats to Monday's business; what is real, what is not and what are the unknowns. AGENDA: 05:47 Six Threats Monday Faces Today 07:04 Threat #1: Vibe Coding: Will Companies Vibe Code Everything 11:24 Threat #2: Will OpenAI and Anthropic Own the Application Layer 13:52 Threat #3: Will Agents Turn Monday and Salesforce into a Database 18:43 Why is Monday Adding 15% Headcount When Everyone is Cutting? 21:40 How Monday is Using AI to be More Efficient 27:49 What Happens to Seat Pricing? What Comes Next? 34:17 What No One Sees About Enterprise AI Adoption 37:13 How Google AI Overview Smashed 10% of our Customer Acquisition 38:49 If Bullish on Monday, Why Has Eran Not Bought More Stock… 40:38 How to Manage Internal Morale When Stock is Down 60% 44:08 Do Private Companies Have Advantages Public Companies Do Not Have 47:28 With $1.5BN in Cash, Why is Eran Not Buying More Companies… 53:30 What is the Most Offensive Bet Eran Would Like to Take? 57:13 Quickfire: Marriage, Biggest Short, Mentors
Transcript 13,569 words · 2 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 Some days I feel like I was ran over by a truck, hit by a plane and barbecued and it's just 11 a.m. What the market is saying to me is the company is worth zero. Okay, fine, now I need to build, you know, screw it, I'm gonna go all in. I'm gonna go all in is the biggest pivot moment for us in the history of the company. Nobody will want to buy software than not doing the majority of the work for them. We're changing everything, basically. The TAM of software, how much companies are going to spend on software is going to be 100x for what it is today.
0:35 Harry Stebbings? The SaaS apocalypse is real and no one has felt it more than Monday.com. With close to 1.3 billion in revenue, they're valued today at just 3.9 billion dollars in the public markets. One of the hardest hit. Today, we sit down with Aaron Zinman to answer one question. In a world of agents, will Monday become Valueless database? Or does it have a future in an agent economy? But before we dive into the show today, as an investor, I'm always on the lookout for tools that really transform how I work. Tools that don't just save time, but fundamentally change how I uncover insights. That's exactly what AlphaSense does. With the acquisition of Tegus, AlphaSense is now the ultimate research platform built for professionals who need insights they can trust, fast.
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4:20 Speaker 00 You have now arrived at your destination.
4:23 Harry Stebbings? Aran, it is so good to have you on the show, dude. I have been wanting to do this one for a while. So thank you so much for joining me.
4:29 Speaker 00 Thanks for having me, Harry. It's great to be here again.
4:31 Harry Stebbings? And by the way, if anyone is listening, you should be watching because Aran looks younger than he did last time. It's extraordinary, the volume that your hair has today, dude. But I wanted to start. You're like, this is not how I expected the show to go. Clearly, we are lacking incredible discipline in our research. I wanted to start on communication, actually, because we see stock price respectfully in the dumps, but actual kind of fundamentals maybe are different. So what is the stock market not seeing that you think they should be seeing?
5:05 Speaker 00 Yeah, so first of all, I want to acknowledge it's a kind of a crazy period. I think for all of us, especially us founders going through this, you know, massive change in the market. So it's definitely not easy. It feels like a roller coaster almost every day, you know? Some days are extremely difficult, but it's definitely quite a journey. I think fundamentally, we need to distinguish between what happens in businesses, which is one thing, and the sentiment change that happened, I would say, in the last year and a half, but more precisely in the last six months, which from my perspective feels, you know, very aggressive, very powerful. You know, on one hand, like if you look at the earning calls and how businesses operate, everything is kind of normal.
5:47 Speaker 00 Some companies are even exceeded expectations and businesses are working great. But at the same time, the sentiment has shifted drastically like I've never seen before, at least from my perspective. And the negativity that now it's been attached to software companies and it seems like every day there's a new doomsday scenario, a new tweet. So the sentiment definitely changed. By the way, there's a lot of truth to that and a lot of things I do understand from the investor perspective, so I'm not dismissing it. But definitely, we need to distinguish between the operation of businesses and the sentiment change that happened in the market.
6:21 Harry Stebbings? I think a realization that the public markets and a lot of people are having is, wow, if we see a gente evolution in the way that we think it will happen and proliferate, then there are core systems, potentially like a Monday, like a Salesforce, which bluntly are never used again and just turn into databases, if anything, which agents crawl on top of. Why does Monday not become a layer that gets abstracted away?
6:47 Speaker 00 Yeah, so first of all, I think there's like five doomsday scenarios I'm familiar with. So that's one of them. You know, I'll just take you back a little bit in time. But first of all, it was everything about people will vibe code their own apps. That was one of them. Another option for doomsday scenario was that some players like, you know, Anthropic or OpenAI or Gemini will capture all the value from enterprise software. I think that's another scenario people are talking about. And the third one is maybe what you referred to as a platform becoming essentially system of records and then other companies capturing the entire value that those companies offer. So I don't mind going through each one of them if you want. I can address each one of them.
7:29 Harry Stebbings? I love the way I suggested one of them and you're like, well, actually here's three more.
7:34 Speaker 00 Well, I can come up with additional three ones if you want.
7:38 Harry Stebbings? No, dude, I would love to. Let's start on the one that's actually, you know, you mentioned at the beginning, vibe coding. It was a journalist, actually. I can't remember what American channel it was, CNN, CNBC, or one of the acronyms that, you know, American has, where she vibe coded her own Monday in a couple of hours or whatever. Why will people not vibe code their own Monday?
7:58 Speaker 00 So first of all, from my personal perspective, I was after a long day of work. I was about to go to sleep. Suddenly I got a lot of messages on my phone saying that we were broadcasted live on CNBC. And, you know, from all the software in the world, that journalist picked Monday to show that you can vibe code a software. Obviously, she could pick any software on the planet. But initially I said, you know, it's a compliment. Monday is beautiful software. So I felt it was a compliment. She's done it to Monday. You know, she could have done it for Salesforce or ServiceNow or she could even create like a search engine. Or a social network at the same time. So so again, like it's a matter of perspective, I guess. Going back to the vibe coding theory in general. Look, first of all, I have to say vibe coding is amazing.
8:42 Speaker 00 I've been coding all my life since I was a kid and seeing this amazing technology become real is unbelievable. But I think there's a big difference between vibe coding, a user interface, and building an actual software that works across the organization with all the depth and functionality that built into that. There's a big difference. I've been coding all my life and I know how relatively easy it is to create an interface and how hard it is to build the software. So I think there's a big difference and I think some people might get confused by that.
9:12 Harry Stebbings? I completely understand that on the enterprise end, but on the consumer and SMB end, for that journalist, for an investor and a fund, does it not just cannibalize your consumer and SMB business?
9:25 Speaker 00 Yeah, look, I've said each one of those theories, I think it has some truth to that, but I think it's marginal. I think it's a very small impact, if any. Going back to the topic itself, I think people underestimate how hard it is to maintain software over time. I think it's it's very easy to create the first increment of a software, but to change it, adapt it over time, it takes a lot of effort and a lot of dedication to do that. And at the end of the day, from my perspective, businesses have a core business operation they need to focus on. If you think about a software today is a very small expense for most companies. Having a dedicated person or a team of vibe coding some apps is a huge cost.
10:04 Speaker 00 So I think in the end of the day, vibe coding is amazing technology, but I don't think it's going to disrupt software companies. I'll give you another point of data, which I think is relevant. You can see amazing VCs like yourself and other people in the industry and amazing founders building companies. If you could vibe code, you know, any company in any startup, no company will have value, not in history and not today. And still people invest billions into new companies, new startups, entrepreneurs build new startups. You know, I've read amazing news about Ramp raising a 30 billion, Harvey, Legora, companies you talked about. You know, you can argue you can vibe. Code them as well, but still the smartest people.
10:44 Harry Stebbings? But you couldn't actually. And so when you actually look at like a Lagor or a Harvey, they are trained on a huge amount of legal data, which they have gained in the last two years from doing what they do. And so you couldn't vibe code with the same quality output that you could if you would have vibe code Monday as a consumer.
11:03 Speaker 00 Actually, I don't think so, because at the end of the day, those companies, it's true that over time they accumulate data and information, but I can argue you can probably get the vast majority of the value even without that specific training. So I think at the end of the day, you could argue you can vibe code any company. What I'm trying to say basically is that as much as I think the technology is awesome, we have our own vibe coding capability within the product. From all the theories of how software is going to be disrupted, this is my least favorite one. I don't think it's going to happen. And I think, you know, most investors that I speak with and people within the industry don't think that's what's actually behind what's impacting stocks and software companies today. Again, it can marginally have some impact, but I don't think that's the majority of what we've seen in the market.
11:48 Harry Stebbings? I completely agree with you on enterprise. The idea that enterprises will is a wonderful. Sadly, enterprises don't work like that. Otherwise, I would be much richer if their buying decisions were so much quicker. The second one you mentioned was that we're going to see OpenAI, Anthropic, Gemini, kind of the model companies move into the application layer. We've seen Anthropic do cowork. We've seen Anthropic do legal. Fuck Dario. He just killed my crowd strike over the weekend. Thanks, Dario. Cheers. Why are they not going to move into the application layer so much more aggressively?
12:22 Speaker 00 Yeah. So again, I think there's obviously some truth to that, and they might capture some of the value, but people overestimate how much they're going to capture. I want to take you back in history, you know, I'm old enough to remember when Amazon built AWS. And everybody back then said that Amazon is going to capture all enterprise software value. Because before that, the hardest part about building a company was actually getting the servers up and running, the website working, storage, having. Like 24/7 availability. That was the hard part. That was the heavy lifting. I remember how people got excited when you got a website online. And when AWS came out and was so easy now to build a website, everybody said, Amazon is going to capture all the enterprise value
13:06 Speaker 00 because it's just so close to the value they offer. What really happened is the exact opposite. We saw a boom of companies building on top of Amazon and software was growing exponentially. Because at the end of the day, I'm not saying Anthropic or OpenAI are not capable of building enterprise software. I'm saying the opportunity they have as being the infrastructure of, you know, the LLMs of the future is so massive. And going after enterprise offering is a whole different business to build. Because at the end of the day, when you sell to companies, it's a different sales process. It's a different mechanism. Nobody's going to buy software for the entire organization based on purely PLG play. The way they're going to adopt, they want to be handheld, especially if you want to use the software across the organization.
13:51 Speaker 00 So I'm not saying people will not use Anthropic and OpenAI for sure they will. But I don't think they're going to capture all the enterprise value because they have a much bigger opportunity ahead of them. And it's not their focus. And no company on earth, with a hour without, can do everything. I don't believe in one player being the one software to run everything in the organization or at all. So I don't see this plays out.
14:13 Harry Stebbings? I think that's probably the weakest one. I totally agree with you. When you look at OpenAI, oh, sorry, Anthropic moving into security, it's a very weak argument to suggest that replaces CrowdStrike or Palo Alto Networks. I completely align with you on that, actually. The third one is a tough one, I think. Which is like how you embrace an energetic future and does it make you a database and not an interaction platform as well? How do you take that one?
14:38 Speaker 00 So it's a tough one because it's true. That's why it's tough. I believe with that with all my heart. Basically, the way I look at it is that if you think about it very broadly, software, as we know, it haven't changed for 25 years. Even before the web, I was building software for DOS, you know, without interface, same thing. You would build a database, you will create dashboards and analytics on top of it. You might have some automations and workflows, but essentially the value, same from day one. And it's true that interfaces have changed. People initially built for desktop application on Windows. It moved to the cloud. So there was a major benefit because it became real time. Everybody was seeing the same thing at the same time. Mobile came into our life, but if you judge by value,
15:23 Speaker 00 basically the same for 25 years. And if you think about it, it doesn't matter if you built a CRM software, IT software, work management software. 90% of the work was done outside of the tool. So if you're a salesperson, you would make the call outside of the CRM. You build the deck outside the CRM. You will prepare for the call outside the CRM. Eventually, yes, you will track the data into a CRM. And your VP of Sales will be able to see what's going on. Same goes for IT, same goes for Monday. You would track your workflows and projects, and you will do everything within Monday, but the work itself was done outside of the tool. So if you think about it, software was extremely beneficial. I cannot imagine the world before software because we take so many things for granted,
16:08 Speaker 00 like everything is centralized, real time, one place, everything is tracked. So we might take it for granted, but it was a major step. Going back to your question, AI changed everything. Because now with AI, I think we flipped the equation. I think AI can potentially do 70, 80% of the work and not 10, 20% like it used to be before AI was brought into our lives. And I think that changes everything in what companies need to do for their customers, what customers expect from software. It will only grow over time. Nobody will want to buy software than not doing the majority of the work for them because otherwise you're just buying legacy software.
16:49 Harry Stebbings? If it's true, and then it does become a database, where is the value in that?
16:54 Speaker 00 Well, I think this is, in my opinion, where investors and the public market get it wrong. You know, if you judge by what software is doing today, you're right. You know, if we don't change, eventually we'll become a database. And nobody will buy Monday to track their work because you will buy software from other vendors that fulfill that promise. But that's not the way it's going to play it out. We're changing everything, basically. You know, going back to what I've said, that I think some of the investors or the public market, you know, I totally understand the way it's reacted because I think what the public market is saying essentially, we understand that the value is changing and software will be different going forward, but we don't know who will be able to change.
17:39 Speaker 00 And I get it because it's hard. Change is extremely hard, especially for an existing company. And the public market is saying, we don't know which company will be able to change. There's so many parameters to that. And we're out until we get that confidence. But if I take a step back, I think that, you know, software going forward, the TAM of software, how much companies are going to spend on software is going to be 100x for what it is today. Software going forward will be much more valuable going forward. Software TAM is going to grow exponentially. And if you combine this with the fact that companies are going to change and going to capture this value, I think the opportunity in the software market today is like we've never seen before in our lives.
18:22 Harry Stebbings? We see enterprise spend on technology at 8% to 12%. It's a varying range on a number of different verticals and kind of variables. What do you think that will be in 2030?
18:32 Speaker 00 Look, I can give you an example from Monday. You know, I've checked it myself. So I think a company like Monday, let's say we have like 1 billion in expenses. A company like Monday will probably spend 60, 70% of the budget on headcount and then 7, 8% on software. But if we can flip the equation and scale businesses not on headcount going forward, you know, every CEO will be gladly increasing the expense on software because it's going to be marginal compared to the headcount growth that you plan for your business going forward. Forward, and I think this will play out more and more into the future. As AI become more dominant, companies will spend much more on software and much less on headcount going forward. Because they'll just become more efficient and they'll gladly spend that.
19:17 Harry Stebbings? Can I, can I ask you there, your Analyst Day presentation showed 20% year-on-year headcount growth in 26.
19:25 Speaker 00 Yeah.
19:25 Harry Stebbings? Is that not completely paradoxical to what you just said about more spend on technology, agentic usage in organization efficiency? When we're increasing headcount by 20%.
19:35 Speaker 00 Yeah, no, I agree. And I think we need to differentiate between the transition and where we're going. So for us, actually, we brought it down a little bit. In the last earnings call, we said it's going to be mid teens. And I think there's also potential, you know, we might even take it lower. I don't know, we'll see. But I don't want to, you know, press the brakes violently. I think we need to do this responsibly because there's a transition period. But if you look at the horizon, you know.
20:00 Harry Stebbings? Can I, can I push you? Why, why not? I mean it in a nice way, dude. The stock's in the dumps. I just had Seb from Klarna on. We said we'd be honest. You're Israeli, I'm British and old.
20:12 Harry Stebbings? Yeah, it's fine. I just had Seb on from Klarna. I mean, dude, he's in the dumps too, poor chap. I love Seb. But he's like, we were at 7,000, we're now at 3,000. By 2030, we're going to be at 2,000. I mean, I think in a couple of years, there's only going to be Seb at Klarna. Why are we not being more aggressive? Fuck it. Now's the time.
20:31 Speaker 00 Look, first of all, you know, it's discussions we have in the leadership team and maybe we'll make other decisions, but I don't think that's the point. I don't think that, you know, if, if we reduce headcount dramatically, it will change, you know, investor perception about Monday. I just don't think that's the essence of what we're seeing in the market. Going back to what I've said, I think investors don't know which company is going to change. And, you know, we just had the earnings call two weeks ago, you know, a lot of fun, you know, obviously I'm being sarcastic. You know, going back to investors and I've talked with, you know, all of our major investors, everybody's saying the same thing. Eventually what they want to see is businesses revenue accelerate. And I totally get it because I think.
21:14 Speaker 00 What people are saying is this, there's huge demand for AI products and people want to buy AI. And we're going to have a few years now that companies are going to look for AI solutions. Given that we're going to see infinite demand for AI products, there shouldn't be a demand problem. So you need to show us or prove to us that you can supply that demand to your customers and new customers. And because of that, we want to see acceleration of revenue going forward. And they're right. I think that's the best way to prove it because if there's infinite demand and you're able to capture that, no reason for your business next to accelerate. And I think that's our role. This is exactly what we need to do and prove to ourselves and to our investors going forward
21:57 Speaker 00 that we are able to accelerate the business and we are able to capture that AI demand that exists now in the market. And this is, you know, Roy and I's responsibility going forward.
22:06 Harry Stebbings? I get you, but like everyone is cutting headcount. To still increase it by mid teens is still a lot. Is it just like you need the people? I still don't understand.
22:15 Speaker 00 Yeah, so the way I look at this is this, I'm not arguing that companies need to become more efficient. So I'm not dismissing it and we will become more efficient. I'll give you some examples of things we're already doing. First of all, we had a team of about a hundred SDRs and we now doing it with agents. A hundred percent is being done with agents. We moved those SDRs to do outbound. All of our support is being done with AI. All of our developers is using plot code and cursor. I don't think there's any company that's pushing AI efficiency more than we do. We want to be at the forefront of that and we're pushing that with all cylinders and we are becoming more efficient.
22:53 Harry Stebbings? I just want to drill down on that because that's super interesting for me, nerdily. When we look at the sales team utilization of AI, when you say we've replaced SDRs, but then you said they're moving to outbound, how are you using AI specifically in the sales team to make the sales team more efficient?
23:06 Speaker 00 So basically, a customer today that goes into Monday when they leave their details on the website, let's say they leave a contact sales form. The way we used to do it before AI was that we had a team that will call back those customers to qualify them, to check the opportunity, and basically qualify them and help them schedule a meeting with the account executive on our team. So this is all done by AI today. So I'll give you some stats. It used to take, on average, 24 hours to get back to a customer. Now it takes three minutes. We used to miss a lot of the calls. People would not answer the calls. Now everything went up. Conversion rate went up. People answering the call went up. Opportunity to book went up. So all parameters went up.
23:50 Speaker 00 AI speaks all languages, available 24/7. So quite an amazing transition.
23:56 Harry Stebbings? You said support also impacted. I'm really intrigued. Do you use an external provider for customer support? Or have you built your own? I interviewed Ariel Kern from Nirvan, Jack from Alwalex, and they built their own. How did you think about that?
24:10 Speaker 00 So when it comes to the SDR part, we've done it our own. We built our own solution. And support, we use some third party, but a lot we do our own as well. I think you still need to highly customize tools today in order to properly enjoy them. Things are moving so fast that we just felt building our own is probably the right path to take at this point.
24:29 Harry Stebbings? Have you seen a shift in the Ange team building with Kasa to Claude Code?
24:34 Speaker 00 I've seen some of it. I think right now it's a sense of flavor. But essentially, we're in a transition period and definitely we see increasing output for engineers. I think part of it is that you find new bottlenecks that are not attached to writing code. I think there's a, on one hand, we see increasing personal productivity. But again, this new bottlenecks you find each time you increase one of those productivities. And we're on a journey to increase more and more the output of our R and D team.
25:02 Harry Stebbings? Sabakana said 3,000 today, and they would be 2,000 by 2030. How many do you have today? And how many people do you think you'll have in 2030?
25:10 Speaker 00 So today we have about three thousand people and and gonna be when?
25:15 Harry Stebbings? Twenty thirty.
25:16 Speaker 00 Twenty thirty, wow. My gut feeling is is probably we're not gonna grow substantially. But look, I think efficiency is important, but I think what's even more important is the opportunity that we have. I think this is where people are missing the point from my perspective. Because it's true that we can focus a hundred percent on efficiency, reduce headcount, reduce expenses. But going back to my point, this is the biggest opportunity in software ever in our lifetime. The biggest opportunity that we ever had as a company and as an industry, okay? This is it's like the beginning of the most amazing journey for all of us. So what I want to do is to capture as much as I can out of this opportunity because it's out there and we can do it.
26:00 Speaker 00 And I think this is where people are getting it wrong. Like, you know, on one hand, I see people excited about private companies because they build tools in the AI era. They're gonna capture the what I've referred to as doing the work. But I'll tell you a secret, public companies will do it as well. We're gonna do it. We are already doing that.
26:19 Harry Stebbings? The challenge I have is like bolt on AI strategies, which I'm not delineating between public or private. I'm delineating between scale companies and a non-scale companies or AI native companies. And I think the bolt on AI strategy, sorry I'm being blunt, could be a you, it could be an air table. It could be a you name that ilk era of company versus an AI native built from the ground up with AI. It's just very different in how you build, integrate and adopt or approach AI as a kind of fundamental platform, no?
26:51 Speaker 00 A hundred percent, and we were the victims of this as well. I'll share a little bit of our journey. So going back a year and a half ago, or even two years, you know, when Sam Altman wrote that famous tweet. This is chat GPT, you can play with it. I remember that tweet, you know, I'll I'll give you the kind of the relationship that we had with AI. So initially, you know, I was excited. I'm I'm excited about every new technology. I'm I'm also a person who like to try things in my own hands and we played with it and it was amazing. But we didn't get it, to be honest. Like, I think most of us didn't get it, maybe some of us got it. And, you know, initially also the investors, they didn't know what it means. And we heard from investors, you know, it's cool, there's hype around it, but we don't know. But something changed about, I would say, a year ago.
27:36 Speaker 00 I don't know what it was, to be honest. Like, it's not like one tweet that I've seen or one product. I feel it was, you know, combining many data points. But I think it was a collective understanding that things are changing and things are changing forever. And this is where you started to see the change in the market sentiment. And like, I felt like a lightbulb moment at that point. And before that, we've done a lot of things, like, it's not that we didn't do things, but we built some AI features. But like you said, I call it a sprinkle some AI dust on top of our product. So essentially, we didn't know what to build. So we built a way for people to build formulas using AI.
28:16 Speaker 00 We built AI blocks, AI columns, but essentially, it was a sugar coating our product because the value haven't changed.
28:24 Harry Stebbings? How do we solve the problem of seats, Aaron? Like, you know, we've lived and, you know, I'm showing my age, obviously, but we've lived in a seat-based SaaS economy where we sell seats. And that's fantastic when headcount scales, as they always have done, and people renew. But in a world where headcount is reducing, where efficiency is increasing, and we're moving away from seats, what do we do when our core pricing dynamic goes away?
28:47 Speaker 00 So, look, going back to the transition, like I said, initially, it was the AI dust that we sprinkle in the product. But then we realized, you know, what I've said is that the value we need to give to our customers, not just us, every sufferer, is completely different. So what we've done internally is to rethink what we are doing as a company. What's the value we try to provide to our customers with Monday Work Management Platform and also with CRM and Service? And rethink our whole product. Part of it is pricing, like you said, that's going to change dramatically. Our go-to-market is going to change, our homepage is going to change, the ads are going to change. The most important part, what our product is giving to, the value it gives to our customers, is now going through the biggest transformation since we launched the company back in 2013.
29:31 Speaker 00 It's the biggest pivot moment for us in the history of the company.
29:34 Harry Stebbings? Can I push you on the pricing? It's going to change. What does it change to?
29:38 Speaker 00 Well, eventually, I think it's going to be more consumption and then entirely consumption going forward. So I think this also be a transition, but now it's going to be hybrid and eventually it's going to be 100% consumption.
29:49 Harry Stebbings? How do you feel navigating that transition?
29:52 Speaker 00 First of all, maybe I'll just explain the transition that we're doing, just to make it more concrete. So basically, companies want to adopt AI and they're going to adopt vertical tools to do that, like the, you know, the SDR example I gave you, maybe another example for support. For legal, there's a lot of vertical solutions people are going to adopt. But I think this is a big room for horizontal plays. And this is exactly what we're going to do with Monday. So basically, we want to be a place that orchestrate between agents and humans, because at the end of the day, you know, maybe in the far future, agents will do 100% of the work. I don't think it's going to happen, but maybe it will happen to some extent. But we're going to have a huge transition period where humans and agents need to work together. And we want to make Monday the default place for
30:37 Speaker 00 people to build agents and to collaborate between agents and people. So essentially, you build agents at the top of Monday, those agents will output tables, docs, files. People will go over it to build their own agents. And essentially, we want to become the default place to do horizontal agents across the company.
30:55 Harry Stebbings? Do you think you're best placed to do that, though? Everyone wants to do that. Anthropic want to do that, ChatGPT want to do that, going back to that one, actually. They do want to do that, and that's right in their wheelhouse. Why are we best placed to do it?
31:08 Speaker 00 So first of all, I don't think that ChatGPT or Gemini or Anthropic are going to do it, because going back to my, the second theory that we discussed, of course, people are buying a Tropic, Claude, they're buying ChatGPT, but it's not a tool where you work with another thousand people and share information. It's a personal tool that people use. There's a big difference between selling a tool that can be used personally and building a tool for people to collaborate with agents. It's a very different product.
31:36 Harry Stebbings? But if you look at OpenClaw and what Peter's done and what he's doing, joining the team at OpenAI, and then you look at their movement into enterprise and Anthropic's focus on enterprise, again, critics would push back and say that's just not true.
31:49 Speaker 00 Yeah, I'll explain again. I think, you know, a company today that wanna adopt AI, they have no idea what they need to do, no idea. It's a new technology. You know, I think we live in an echo chamber of tech, but the world out there is very different. And I think essentially, companies will wanna buy AI. They will do whatever they need in order to buy AI capability, because it's gonna be a competitive market. And if they won't do it, they won't survive. But.
32:13 Harry Stebbings? Do you not think that's where ChatGPT's brand wins? Fundamentally, the brand of ChatGPT is so strong that they are signing enterprise contracts with a velocity we haven't seen before because of that brand. Anthropic are too. But again, I go back. And as a Monday holder, do we not need to jack the shit out of our enterprise brand? Because otherwise, they are gonna eat the momentum on the enterprise side.
32:36 Speaker 00 So I think we need to differentiate what enterprise contract means, okay? So the fact that ChatGPT or Gemini or Anthropic are selling a contract that a thousand people, let's say within Monday, can use Anthropic, it's great. But that's not the product I'm talking about. It's like comparing Microsoft Office with Monday. It's not the same thing. There's tools that people use individually, which is great. Personal productivity tools, building agents, but then there's the actual work. It's like claiming that there's no need for SDR software because you bought Anthropic. It's a different problem to solve. So I think the problem solving how people and agents are working together in one workspace is a very different product, is a very different problem.
33:21 Speaker 00 I think companies will want guidance on how to do that. They're gonna need help setting up agents, figuring out what they can automate with agents and what they can replace in terms of headcount. And this is not by buying off-the-shelf product that is a generic product. You will need a product that can help you collaborate between humans and agents if it's a very different product compared to just buying a license to LLM. And I think eventually, if you look at Anthropic, OpenAI and Gemini, they have a much bigger opportunity they wanna chase. They wanna be the backbone of the LLM industry. They wanna capture as much as they can in terms of that market share. And I get it, it's a U. Opportunity. Again, going back to my AWS comparison, they are the infrastructure,
34:05 Speaker 00 but there's going to be a lot of products built on top of that. I think if anything, we're going to see an excess of software being built on top of the LLMs, not less, exponentially more, because the opportunity is so massive and the TAM is so huge. And going back to Monday, we're going all in for that. We're changing the product, the value proposition, how people use the product, how people onboard, and what people should expect from the product. If you haven't built an agent on Monday, you're not using the product properly. And that's a major shift. The boards, the dashboards are going to be more in the background, and the agents more in the forefront. And it's a huge change, it's a scary change, but I believe in that with all my heart, because I think the opportunity is massive.
34:47 Speaker 00 We're at 0.001% done of where the world is going.
34:51 Harry Stebbings? Do you think we overestimate the speed of adoption for enterprise AI usage? Or do you think actually we're at a tipping point and it will tip much faster than we think?
35:00 Speaker 00 I think technology is moving fast. I think organization is going to take more time. You know, what is AI adoption? There's so much nuance to that. There's so many things. Look, at the end of the day, I think what people are confusing is, you know, AI can get super smart, and we've seen it grown exponentially. But no matter how smart you are, if you don't have context, you cannot perform your job. You know, even the most intelligent person on earth cannot do their job if they are not aware of the context. And if you think about any company, even Monday itself, 90% of the context is not documented anywhere. Nobody knows it, you know, it's something that kind of floats in the air. You know, what's the idea? What's the strategy? Who's doing what? What's next month? What's next year? How are we going to do it?
35:44 Speaker 00 Why are we doing what we're doing? What's the thought process behind it? So I think we're going to see a transition period before all that information and knowledge and intelligence is going to be documented, which might happen in the future. I think we have a huge transition period of people working with agents. I think you can see some small companies and, you know, I've been following Jason Lampkin and what he's doing on his own team. You know, I'm a big fan of Jason.
36:09 Harry Stebbings? Do you know the joke I say with Jason is the best venture fund of the last decade was Jason Lampkin's unresponded inbox? Because every great founder sent him an email being like, please invest, and he just didn't get back to them.
36:24 Speaker 00 I always joke with Jason that we have like a one sided relationship where I listen to every word he says and he's my mentor, but he's not aware of it.
36:34 Harry Stebbings? So it's like. I do a show with him every week and he is my mentor and he is aware of it. He's such a good dude. He is so rad, he is so into it, it's insane.
36:45 Speaker 00 I know, but look, at the end of the day, you know, a small team like Jason's team, and Jason is very forward leaning, can replace everything they do with AI. But for an existing company in business, it's going to be more of a transition over many years. And we need to remember that most economy, you know, 95% of economy is not software companies, it's actual businesses. So going back to my point, we're going to see a transition period of companies adopting AI, AI working with humans, humans collaborate with agents. It's a massive opportunity and I don't think OpenAI, Anthropic or Gemini are going to go for that because it's such a different sales process, enterprise sales, top down, different tool use.
37:30 Speaker 00 And we're going to go all in for that opportunity because our advantage is that we are the best platform for people to working together across the organization. So we're going to take that part of business and add the agents on top of it and change the value in what people do with the product. And I believe it's going to be massive going forward.
37:47 Harry Stebbings? If we shift a little from enterprise down to kind of, it can still be, but more SMB and consumer. One thing that Monday has done unbelievably well, and we spoke about it last time, was the customer acquisition machine you've built on SEO, content, YouTube. It's been phenomenally successful. How do you think about critics who say that customer acquisition engine is completely changing in a world of GEO or LLM discovery in a changing content world? How does customer acquisition channels, funnels change?
38:16 Speaker 00 I think going back to my original opening where I said that there's the sentiment change, but businesses are unaffected. So we were affected by one thing, which is Google introducing AI mode in the search results. So Google used to be a significant acquisition channel for us, and definitely it took a hit in terms of people clicking on sponsored links because people see the AI answers. So definitely.
38:40 Harry Stebbings? When you said to get, how much of it, I'm sorry, I'm really naive here, like a 10%, a 30%, 50% broad strokes?
38:48 Speaker 00 It was about 10% of our acquisition in terms of new ARR. But again, Google is very transactional. So people usually, when they're searching for something, they're willing to buy at this point because the intent is very high. So we lost some of the more transactional deals, more SMB oriented, and we shifted that budget to other channels, but they're kind of longer sales cycles. So we definitely took a hit because of that. But apart from that, we have 70 other channels that we acquire customers from, and we didn't see any impact on other channels. So it was a significant impact, but from my perspective, it's isolated to that.
39:23 Harry Stebbings? Can I ask a hard one? If we are the work platform between agents and humans, and we have this grand fusion, this most exciting time ever, why have you not bought any of your own shares back?
39:34 Speaker 00 Well, we are. We announced a buyback program of 870 million, and we said we're going to spend it over the next two, three years. We've already done some buyback in Q4. If we're going to see opportunities, we're going to buy back our shares. And definitely there's opportunities right now. So we are looking into that, and we do have a buyback program.
39:55 Harry Stebbings? What about you personally, dude? We saw ServiceNow CEO spend 3 million bucks, and that was revealed to be less than his car collection, which was a rather annoying title for an article, I have to admit. I saw it and I felt sorry for him. I was also really intrigued to see the cars, which they didn't show. Why not buy it back personally?
40:13 Speaker 00 Yeah, so first of all, I'm on a 10b5 program. So basically, I have to six months in advance, make a six months' plan ahead. So I'm not saying I won't. When the plans open up, I might buy more shares personally. Again, it's something I need to decide with my wife. You know, it's not a personal decision for me, but definitely it's opportunity. But I can share another thing is that not myself or my partner Roy or the rest of the leadership team is selling shares. In my 10b5, I have a number. I'm not willing to go below in terms of selling shares. And I can say the price now is much, much lower than that number. So I'm not selling any shares personally. You know, since the IPO, I still hold probably eighty something percent of my shares.
40:56 Speaker 00 So I sold less than forty percent fourteen years in this journey. So I don't think I need to prove more that I have like all my skin is in the game. You know, I'm a hundred percent in. I believe in the future of the company. You know, as I said, it's one of the biggest opportunities that we ever had as a company.
41:12 Harry Stebbings? Can I ask you from a like personal perspective or leadership perspective? When you have a challenging period like this, what do you know now about how to galvanize a team when a stock price is so impacted? And of course, people look at it every day and look at their net worths.
41:31 Speaker 00 Look, it's been a roller coaster. It's been hard, you know, emotionally, everything in the last few months. I can share that, you know, it's still fresh, but you know, the last earnings call, the stock went down to seventy dollars. You know, obviously, when the stock is going down and I've seen all the earnings calls before Monday and after Monday, I felt like no matter what companies are going to announce, the stock is going to go down twenty percent. So I was not optimistic. I was not sure what's pricing and what's not, but it is what it is. I get it. The sentiment is so negative.
42:03 Harry Stebbings? How do you feel going in when you know that you're going to get pummeled? Are you like, fuck it, you know what, there's nothing I can do? Are you like, oh, God, I'm dreading this. Oh, no.
42:12 Speaker 00 Look, I didn't know what to expect and overall I'm trying not to make the stock price to manage my decision-making process, but I look at it, you cannot ignore it. It has a psychological impact for sure. And definitely it's not easy or fun when you go up and talk with analysts and investors and nobody's happy. Again, I don't think we're unique because ServiceNow is down 50%, Salesforce is down 60%. It's not helpful. So I understand there's things I can control, there's things I cannot control. I cannot control the negative sentiment in the market. What I can control is what can we do about it? So I'm trying to focus on the things I can control.
42:52 Speaker 00 Going back to the earning call on Monday, the stock went down, obviously lost some sleep over it. I woke up 3 a.m. thinking about it. Tuesday, woke up 2 a.m., didn't fall back asleep. But when I woke up Wednesday and the stock was 70, I had a feeling of relief, to be honest, because I said, okay, 70 represent, let's say, 3.7 market cap. We had like, I don't remember the exact number, but roughly, let's say, 1.5 billion in the bank, cash, no debt, so the enterprise value is 2 billion. We have like, again, I don't want to disclose a specific number, let's say over 1.3 billion of ARR. So it's like 1.5 multiple.
43:36 Speaker 00 So I felt like, okay, what the market is saying to me is like, again, air quotes, like the company is worth zero. Okay, fine, now I need to build, I need to prove. And suddenly I felt relieved because I'll do everything needed in order to make the company successful. It can't get any worse. Yeah, the stock can go down, but I feel this is like the lowest sentiment that software companies ever had. So yeah, it can get lower, but to be honest, it's pretty low right now.
44:06 Harry Stebbings? I love you. Again, the financial analyst goes, you know, because I obviously am a Monday holder. He's like, dude, the thing about Monday, I thought there was a flaw. I was wrong.
44:17 Speaker 00 I'm not saying it cannot go down. Obviously, every day there's a new tweet and all the stock is going down 70%. I cannot control it, but what I feel now, you know, screw it. I'm gonna go all in. I'm gonna go all in both for myself and a management team. This is the biggest opportunity. There's only upside to where we're at. We're gonna take the risks. We're gonna go all in and do whatever is necessary to win. I'm extremely motivated for that.
44:42 Harry Stebbings? Do you think private competitors have an advantage on you that you don't have because you're public? If you look at Stripe and Adyen, I think Stripe have an inherent advantage in being private that Adyen don't have because they're public in what they can do, how aggressive they can be, how they approach products, you name it. Do you think that's the case here?
45:04 Speaker 00 I think the opposite, the opposite. If you kind of relate to what I've said. I feel like I was kicked in the head so many times by now that, okay, I get it. And I feel when you're private, you know, you can try and ignore what's going on and even say, you know, everything is okay. But for me, I get it. And I don't blame the investors. I think investors are super sophisticated. It's an amazing market. What the investors are saying, I got the message. I got the message and they're right. They don't know who's gonna be successful. But I think this is where they get it wrong because basically I think what I'm trying to say, Harry, throughout our conversation is, are you playing defense or are you playing offense? And I think every, every day I go on Twitter and I read what people are saying.
45:48 Speaker 00 And everybody is publishing an article, you know, this company has more robust system records. This company has a moat. This company is enterprise. Who cares? Who cares? What are you arguing? Who's gonna change last? Who have more time? I'm saying the opposite. This is the biggest opportunity. Everybody have to change. Everybody have to change. The faster you change, the better. And I think some, some kind of companies will not be able to change because, I don't know, the founders are not there because it's hard, because the DNA is not there, because it's a hundred thousand people company, because they're not sure where they're going, because they don't have a culture of execution. My confidence come from the culture we built, the fact we always were great execution.
46:33 Speaker 00 The fact that once we make a decision, we're gonna go all in. We have everything needed. We have the cash. We have the talent. We have the execution. We know what we need to build. That gives me a lot of confidence, the people in the company and our mission. So, you know, if you're playing defense, good for you. I feel for us, it's an opportunity to play offense and do whatever we need in order to win. And this gives me a lot of confidence because I'm building the future.
46:58 Harry Stebbings? Can I ask you, you said there you have a billion and a half and it's, you know, 3.7 or whatever it was. There comes a time when actually it's just too low, it's mispriced. And at that point, again, I have many public market friends now. They are going, I want to take it private. This makes no sense anymore. It is strategically wrong. Would you like to take it private?
47:18 Speaker 00 No, I don't see a reason. No. Look, I think at the end of the day, you can be private, you can be public. The question is, do you need to raise more money? And we don't. We generate 27% of free cash flow. We don't need to raise more money. We have everything we need going forward. If anything, we'll become more efficient. I see the retention rate highest ever, gross retention highest ever. We're still acquiring a lot of customers. So I'm very confident about the business. And I think this is where people don't understand that the businesses are working good. And things might change, but you know, nothing is more sticky than a SaaS product. So I definitely, I'm not worried about, you know, operationally. And we are changing, you know, as we speak. So we don't need to raise more money and no need reason to go private and we can stay public.
48:02 Harry Stebbings? You said about a billion and a half in cash. What a wonderful luxury that is also that not many have. What would you like to buy that you haven't bought? From an M and A perspective, why are we not being more aggressive?
48:14 Speaker 00 Yeah, so look, we are looking into companies and we also met a few that we were close to acquiring. But look, at the end of the day, this is not how we're gonna win. If I need to bet the whole company future on an acquisition of a startup, I'm not doing my job as a CEO. The problem now with private companies is that we have the opposite valuation between private and public. If money is valued at 3.7, every startup in the private market with 5 million of ARR is now being valued. Two billion. So yeah, I can buy it with partially cash, but I'll need to use my stock as well. So I don't have a lot of opportunity buying, you know, a few billions worth of of a private company. It's not gonna play out. And again, like, I feel we have everything we need in order to execute.
48:58 Speaker 00 So I think, you know, it's a cycle. It's a cycle for public companies. It's also gonna be a cycle for private companies. Now there's a lot of money in the private companies, in private investors, but you know, it's a cycle. At some point, the investor is gonna see the same company twenty times a month and LPs is is not gonna pour a lot of money. And I get it. I've I've been in cycles before.
49:18 Harry Stebbings? Are you in CEO groups, WhatsApp groups?
49:21 Speaker 00 Not WhatsApp group, but I have a few CEOs I consult with, yeah.
49:25 Harry Stebbings? What do they say? Are you guys all just going, what the fuck, together?
49:30 Speaker 00 Not really. You know, the the problem with other CEOs is people don't expose their emotions too much. I'll say that. But I think people feel resilient. I think we give each other confidence. I think some CEOs are, I wouldn't say ignoring the problem, but don't understand the magnitude of what needs to change. And I think some are more kind of advanced in how they think about it and understand the magnitude of what needs to be changed. Again, my confidence is is coming from doing and changing. So that gives me a lot of confidence going forward. So I don't need anybody to kind of pat my back. And I got Roy, my partner, and the rest of the leadership team. And we feel very confident on where we're going.
50:09 Harry Stebbings? From like a a marriage and from a personal perspective, it is fucking hard what you're going through. I don't think a lot of people like quite realize the emotional and personal toll that it takes. Getting on a show like this with me even, after everything that you go through, is intense. And I remember Seb from Klarna saying, he does shows, interviews, and he did one that was so hard. And they just shit on him, shit on him, shit on him. And he got in his car and he played Queen under pressure. And he just like sang full pitch under pressure. And like, he always thinks to that moment. Like, from a personal perspective, what are the things that get you through the really hard times?
50:48 Speaker 00 So first of all, I want to acknowledge it's it's hard. It's hard. And, you know, I told somebody, someone the the other day that some days I feel like I was ran over by a truck, hit by a plane and barbecued. And it's it's just eleven AM, you know?
51:06 Speaker 00 So definitely, there's days like that. But I want to say that I feel very good now. And I feel we're doing the right things. I'll tell you, I'll give you, I'll say two things that really helped me. So one is the people in the company. That's something that's very significant to me because, you know, once we tell them what we're doing and focus on doing and execution, I could see in their eyes, like although it's scary and we're changing a lot of things and we're taking big bets, I can tell in their eyes that they're excited. They appreciate we don't ignore the problems, that we don't say everything is okay. We are changing, we are adapting for the future. And people are working incredibly hard. They're dedicated from the bottom of their hearts. And that gives me a lot of confidence.
51:49 Speaker 00 And the second thing, and I don't want to get too emotional, is my family. My wife and my kids, super significant. I feel I have like a network of support. At the end of the day, what I really care about, you asked me about my personal wealth. I don't care. I just want the company to be successful. I feel immense sense of responsibility for the future of the company, for the employees, for the investors, for everybody that's part of that ride. And I want to do whatever it takes to capture this opportunity. And I want to play offense. I think that's the point. At the end of the day, I think there's so much noise. Just listening to the noise is the wrong thing to do as a leader and as a CEO. Noise is Twitter and other article, even public market.
52:34 Speaker 00 I want to focus on the essence. For me, the essence is very simple. It's the biggest opportunity of our lifetime in terms of software. We need to change and we are changing. And because of that, I'm confident we're doing the right things. This is what in my control. I will do whatever is necessary. So this is the essence and this is what we're doing. And that gives me a lot of confidence going forward.
52:55 Harry Stebbings? There's a kind of content creator, influencer, whatever. I'm quite into these kind of inspirational speakers. It's got Alex Hormozi. And he says, you know, whenever I'm going through a hard time, I think, you know, the harder the challenge, the greater the story that comes out of it. And this is the story that you will one day tell your kids.
53:11 Speaker 00 Yeah, I'll tell you how I look at it. I got the front seat in probably the one of the most exciting period in human history, the birth of intelligence. And I can navigate this ship and it's amazing. It's such a great opportunity. I think everything in his life is a glass half full or half empty. I can look at it and say, oh, you know, like I was on a path and everything was great and we built this great company and so on. But the way I look at this today is maybe this is our biggest opportunity as a company. Maybe we waited for that moment. And if we do the right things, we can reaccelerate the company and even grow much larger than what we could have become as a company. So I hold into that and that gives me a lot of confidence. And if you ask me today how I feel, I feel
53:54 Speaker 00 great because as I told you, we hit the bottom or maybe close to the bottom. And from here we can only grow and focus on execution. This is exactly what we do.
54:04 Harry Stebbings? You said about kind of this is a time for offensive. Before we do a quick fire, if I would ask you like, what's your most batshit crazy offensive move that I'm sure is totally unrealistic, but you would like to do. So like for me, I look at it as a load of companies like you, Duo, and a load of others where I'm like crazily mispriced assets. Let's roll up and buy in a really aggressive, I want to raise a hundred billion dollars and do this. It's a batshit crazy offensive idea. What would you say is yours?
54:33 Speaker 00 So basically, our strategy is twofold. One, in terms of our horizontal platform, we're going all in agents and humans working together. We're shifting the product 100% the pricing to go to market the product. We have two vertical offerings, the CRM and service. For that, we're building those products from scratch, being 100% agentic. So basically going full in on that opportunity. The way I look at this today, service dominated by ServiceNow, CRM dominated by Salesforce, it's open market today. I believe in their ability to change, but they need to prove it. I want to go all in. I think we made this choice to go for CRM and service back in the days where we have crazy competition. Now I feel
55:14 Speaker 00 the playfield is leveled and there's opportunity. We have one big horizontal bet, two vertical bets with service. And we're going all in on all three. I'm very confident about that. So I think it's a big bet and we'll do whatever is necessary to capture that opportunity.
55:30 Harry Stebbings? Who's a harder competitor, HubSpot or Salesforce?
55:33 Speaker 00 Again, the question is who's who's going to be able to change? That's the most important factor for me because at the end of the day, it's not what they built, but how can they change? Going back to my point about public market, I think this is where companies are mispriced. Everybody is priced now on the downside. Again, it's because of lack of information, not because not because the market is not sophisticated enough. Because you don't know, you don't know who's going to be able to change. But I'm confident we will change. There's a lot of questions, how, and there's a lot of risks to it, but we're going to change. And the question is who else is going to change and who else is going to change successfully and responsibly?
56:10 Harry Stebbings? Who do you think will change more effectively, HubSpot or Salesforce?
56:13 Speaker 00 Being a bigger company is harder because it's hard to move humans. That's the hardest part. I think people think enterprise is a benefit, maybe SMBs is better because SMBs are more open to adopting new technologies. When you play defense, some of those things might look as disadvantages, someone to SMBs or being a small companies. If you play offense, those disadvantages might become advantage. Because those customers might be sooner to adopt technology and will buy those products before enterprise will buy. So I don't know, to be honest, and it's for them to prove. You know, I will never underestimate each one of those companies because they've built incredible things. I think in general, I think investors underestimate incumbents' ability to change.
56:58 Speaker 00 Their willingness to change, the motivation to change. You know, private companies are great, but you know, those companies reach where they're reached because of multiple things. And they're very successful companies. And I think the cycle is going to shift once, you know, like fungus off the drain. You're going to see another public company change and accelerate, another one accelerate. And investors are going to say, hmm, it happens. So let's rethink who else is going to change over time and valuations will go up.
57:24 Harry Stebbings? What do you people say that the babies are being thrown out with the bathwater? Very strange analogy, but it's kind of what they say for the public market today. Other than Monday, what is the biggest baby being thrown out with the bathwater?
57:36 Speaker 00 I don't know. I think I think most of them.
57:39 Speaker 00 It's not like, again, I'm not an investor, so I don't have my own list. I think it's been a bloodbath. So it's really hard to change.
57:46 Harry Stebbings? It totally has been. Listen, I want to do a quick fire round, dude. So I say a short statement, you give me your immediate thoughts. What have you changed your mind on in the last 12 months? What did you think that you maybe don't, or what didn't you that you now do? What's been the biggest mindset change?
58:00 Speaker 00 Well, obviously AI, like, you know, a year ago, I'll be honest, I didn't understand. I don't think I was the only one, but I didn't understand the magnitude of the change. But today I understand that software is fundamentally changed forever. So that's something I didn't understand, but now I totally get it. It's obvious to me that the future is going to be very different for software.
58:20 Harry Stebbings? What criticism about you stings because it's partly true?
58:24 Speaker 00 About myself?
58:25 Harry Stebbings? Yeah.
58:25 Speaker 00 I think one thing that I think we can do better is to tell a story in a better way. I think Roy, myself, we're not, even though we do great marketing for our product, I don't think we tell the story good enough for the company. And definitely that's something that I feel we can improve. Because I often feel like, you know, if people knew what I knew, they will be much more confident in Monday and where we're going. And I feel it's my responsibility to do a better job telling our story and our strategy.
58:55 Harry Stebbings? OpenAI at 500 or Anthropic at 380, which one would you rather be an investor in?
59:02 Speaker 00 First of all, I think we all need a little bit of humility. What I've heard in the last year is this, Microsoft is the most amazing companies. Microsoft is finished. Google is finished. Google is the best company on earth. OpenAI is the most amazing company. OpenAI is finished by Anthropic. And this is like three months cycles. So I feel it's like 1998 and we say, you know, Yahoo and Netscape gonna suck all the value from the internet revolution and we know nothing. So I feel we're in the beginning of an exponent. It's really hard to say who's gonna win, who's gonna lose. It's a horse race. I think we're probably missing 90% of the picture of how it's gonna play out. So I'm not an investor. I'm not, I'm making bets on Monday.
59:45 Speaker 00 Monday, not the other companies. Definitely, I feel Entropic have a little bit more momentum right now. They can change and it will change, I'm sure.
59:53 Harry Stebbings? The the trouble is when you don't know, we don't know, and no one knows.
59:57 Speaker 00 Yeah.
59:57 Harry Stebbings? And what the trouble then is, it's a flight to safety and a flight to cash. And that's the problem that I think we're gonna see now, which is like, no one fucking knows, and so no one wants to play the game. I've had enough of casino roulette in the public markets. Like, I'm selling and I'm just going to cash. And that is what you're seeing everyone do, a movement to cash.
1:00:16 Speaker 00 Yeah.
1:00:17 Harry Stebbings? Warren did it brilliantly with Berkshire six months ago. That's a problem for us, though, because we need that cash in Monday.
1:00:24 Speaker 00 Yeah, but but look, it's a cycle. What happens in the cycle is that over time, you see consistency and you're getting confidence. And then you see companies accelerate, you gain confidence. Nothing I will say will change perception. Time and execution will change perception. And this is our responsibility as CEOs, and this is what I'm planning to do. Over time, it will change, it's a cycle. I I've been through so many cycles so far, like.
1:00:49 Harry Stebbings? Is this the hottest one, or is this like every other one?
1:00:52 Speaker 00 Look, everybody enjoyed that twenty twenty one cycle with Covid, right? But it was also also a cycle. I remember when um our stock went up to four hundred after we IPOed. One of our investors told me something, Ken Fox from from Stripes. He told me something which was brilliant. He told me, isn't it great that the stock is going up without the revenue going up? And I said, what? What are you talking about? And he said, yeah, everything you gained is through sentiment change, nothing you've done. And it really resonated with me. I said, OK, I need to distinguish between what we do as a company and our growth and the market sentiment. And if you don't praise yourself when the stock is high, you won't be impacted because when the stock is down.
1:01:34 Speaker 00 If you don't attach your personal success and personal ability to lead a company with the sentiment, and you need to focus on the business performance, that that that was his point. And it really resonated. And I didn't celebrate when it went up to four hundred, because I knew it was temporary at the end of the day, it's a cycle. So everybody enjoys when the cycle is up, but also now when the cycle is down, I need to focus on the business metrics, the revenue, the retention, the things we are doing. That's the important part, not be carried away by the cycle itself.
1:02:04 Harry Stebbings? Totally agree with you and a hundred percent very difficult to do. And that's where I like the experienced CEO that you are in terms of having seen many before. I think it's actually where younger CEOs struggle, where it's the first cycle and the depths are so low and the highs are so high when it's the first time you've done it. But ultimate one, which other CEO do you most respect and admire? When you look across the board at your counterparts, which one do you like them?
1:02:28 Speaker 00 Yeah, so of course, and again, it's a personal friendship, but I really love Avish iPhone Wix and Nir. You know, we're close friends, so obviously I ask them a lot of questions. But we also have other CEOs that I talk with. And again, it's hard for me to pick like a name because I don't know them personally. So, you know, when you pick somebody, you take their entire personality with it. So it's really hard for me to pick. But look, the amount of information that I acquire through podcasts, blog posts, videos, I probably acquire like five, six hours of content a day. You know, I walk to work, I walk back, I do the dishes. I have, you know, my kids are saying, why do you have the AirPods in your ear all the time? Because I just feel we need to learn like crazy.
1:03:13 Speaker 00 I try to gather as much information as I can. And I think I learn a lot from different people's perspective. Also, I love the show you guys are doing, the four of you, the three of you, sorry. So I listen to that. You know, I think now you need to be learning as much as you can. So that's the mode I operate in.
1:03:33 Harry Stebbings? I'm out of here in a penultimate one. What's your biggest marriage advice? When you go through a really tough time as well, it's very difficult for you. It puts a strain on Matt. What's the biggest marriage advice? Like advise me.
1:03:44 Speaker 00 Well, first of all, I've been with my wife for 23 years now. So we basically grew up together, but I'll tell you one thing. So my wife has been nothing but amazing throughout this journey. And specifically, I would say the last six, eight months. It's not like she doesn't care. She know what I'm going through, but the amount of support I get is unbelievable. So one advice I would say, and this is actually from my therapist. So she gave it to me because I told her what I told you now about my wife. So she told me, say it to her. When you meet her this evening, say to her what you said to me. I said, right. I mean, I have to because I feel it, but I haven't said it to her. So, you know, communication, sharing how you feel, the good, the bad, talking about it.
1:04:29 Speaker 00 It's the best advice I can give with my wife and also with partners at work. So I feel the more you open, the more vulnerable you are, the more you share, the more intimacy you create and the better relationship you create with other people.
1:04:43 Harry Stebbings? Very un-English of you. We tend to not share much.
1:04:47 Speaker 00 I know, I know.
1:04:48 Harry Stebbings? Yeah, we're very uncomfortable. We normally call each other kind of Mr. And then surname is like Mr. and Mrs. Stebbings. Yeah. Final one, dude. What are you most excited for in the next 10 years? Like, my mother's got AMAS. I'm super fricking excited for advancements in AMAS treatment because of AI and everything that we're seeing with longevity. What are you most excited for?
1:05:07 Speaker 00 This is probably the biggest change since the invention of computers. I'm lucky to be part of that. And I'm excited to see how this plays out, you know, it's, I think if you ignore the negativity that attached to that, it's pretty exciting. I mean, it's quite a period to be alive. It's pretty amazing.
1:05:25 Harry Stebbings? Dude, when you think about like a civilization and how actually for 1800 years, it really remained relatively flat, feudal systems, farming-based economies. When you look at the last 200 years, I know it's a large amount of years now, but proportionally, it's not at all, actually. God, I'm so grateful we're living in this time. How fricking epic is this? Like, amazing.
1:05:47 Speaker 00 Humans didn't shower in hot water like 80 years ago. And now, if you don't have hot water in your bath when you're, before you go to sleep, it's like, it's ruining your day. So it's like, we get used to good things so easily. I think, you know, specifically with AI, we're gonna get used to getting the best treatment, best doctors, everything's gonna be instant. We got, each one of us is gonna have the most amazing personal assistant. Our life is gonna be amazing. And of course, we're gonna complain. Of course, we're gonna look at the things that don't work. But I think going forward, probably the value and the quality of life is significantly gonna go up going forward.
1:06:24 Harry Stebbings? Dude, as I said, I so appreciate you taking the time. I so appreciate you putting up with the harder questions. You've been fantastic. So thank you so much, man.
1:06:32 Speaker 00 Thank you, Harry. Thanks for having me.
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Previous 20VC: Why Cursor is Dead | An AI Tsunami is Coming & You Need to Prepare | Systems of Record Become Valueless Databases with Agents | Is This The End of Tech Private Equity with Jerry Murdock, Co-Founder of Insight Partners Next 20VC: Anthropic vs The Pentagon: Who Wins | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR | Block's 40% Headcount Reduction: AI or Overhiring Page updated October 26, 2026 · transcript and summary are machine-generated