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12 Sept 2025 The Logan Bartlett Show EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners
“All of a sudden the total dressable market looks huge because the addressable market of legal advice and legal labor is actually quite large. So that's really interesting to me because I think the traditional perception of where there are addressable markets in software I think has been upended because agents aren't simply productivity enhancements for people, but actually doing a job.”
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- 12 Sept 2025
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…Thank you for doing this. Thanks for having me. I'm glad we got it on the calendar. It's a good time to do it. You guys recently announced a new round. Congratulations. Thank you. I appreciate it. It's a nice milestone on the journey. You could test them at the way you guys have built the date and where you're headed over time. Yeah, it's a milestone, but I think it's a way to put it. You know, raising financing is just, you know, adding fuel to get to the place you want to go. And I think for a entrepreneur like me and my co-founder, Clay, it's, you know, we want to create a enduring, durable company. And so it's just that, just a milestone. But it's good, good time to reflect. We're really proud. I think we're the clear leader in the space we operate, which is AI agents for customer experience, customer service. But I always talk about how similar this AI wave is to the original internet wave and altavisto is first and Google is the one who writes the history book. So we need multiple years of sustained, impeccable execution, basically from here. And that'll be happy. But I'm excited for the milestone. There's the nor Mcdonald joke that like the good guys always won in history. It's like, you get to define the terms of success in that way. I guess what do you think to that? And when you're making that comparison to internet versus AI, where do you think that parallels exist? And what do you think breaks down as you kind of think about comparing the two? One thing that I think is quite similar is there were some very obvious bets on the internet like search and e-commerce being two of the most prominent impairments. You know, you didn't need to be that savvy about the internet to think, wow, it might be useful. People could buy things, you know, digitally. And the question was who will own that market? Will Amazon and Buy.com had very different strategies, even different portfolios of products that they initially sold? Amazon clearly had a much better both strategy execution. There's a lot of details they got right. Look at the search market. You know, I mentioned altavisto in Google, but one of the more impressive technical companies that we competed against was ink to me. They had a really good engineering team and you know, I could tell you why PageRank was better, but they had a solid team, but they had a B2B business model. They're essentially licensed. They search engine to portals. And that left out the opportunity to create outwards, which turned out to be the greatest business model of all time. So there's so many details that, you know, dictate whether you're the one you turn into Google or altavista or ink to me. But going back to your question, what's interesting about the AI market is there are a few areas that are obviously going to be impacted by AI, software engineering, customer service, content marketing, visual effects industry. There's probably others, different than the legal industry. few areas that are obviously going to be impacted by AI, software engineering, customer service, content marketing, visual effects industry. There's probably others, different than the legal industry. And as a consequence, you know, it's not like, I got this great idea. Hey, if I told you, oh my gosh, AI for customer service, it's not the concept is obvious. The question is, do you have the right product? Do you have the right good market model? That's what I mentioned, the ink to me, Google thing, you B2B or you B2C. What is the packaging? What is the form factor that will become dominant? And so as a consequence, it's an intensely competitive time. Just like my recollection of the .com era is. And I think that's really interesting. So you have very clear markets with very intense competition. And that's different than other markets. You know, I think in the mobile phone came out, some of those categories like ride sharing wasn't like a self evident market. And then there was a couple great insights and created the ubers and the lifts of the world. I think right now, many of the biggest markets are already known. And as a consequence, one of our company values is actually competitive intensity, which is unusual. And it's the first line of that as we know we're not entitled to our success. And I think it's a really important part of being successful in this era. We're a bricks down. I think it's shifted the landscape of what is a software company. I love the example of Harvey is a company I really admire. I can't think of like a great legal tech company. I'm sure there are a couple. I don't mean that in a backhanded way towards any of them. But it wasn't like as you went through the top 10 enterprise software companies in public markets. There's not one in legal tech, right? There's ERP systems and CRM systems and all these others. It's just not one of the key categories. In part, because the tam for selling productivity enhancement to lawyers is not that big. But now all of a sudden with Harvey, you're actually doing the work and doing the antitrust review. All of a sudden the total dressable market looks huge because the addressable market of legal advice and legal labor is actually quite large. So that's really interesting to me because I think the traditional perception of where there are addressable markets in software I think has been upended because agents aren't simply productivity enhancements for people, but actually doing a job. As a consequence, I think how you evaluate the value of a piece of software starts to move away from traditional software productivity metrics. Think about a CIRA agent that actually makes a sale for you. The way you would value that is not really even related to AI or software. The way you'd value it is basically one of the margins on that sale. What would be the commission you'd pay a person to make that sale? And so as a consequence, I think it really has dramatically shifted the traditional view of how to value software, just as either a venture capitalist or an economist, it's really changed the markets. And I think I'm excited for that. I think it's going to be a really positive thing for w of how to value software, just as either a venture capitalist or an economist, it's really changed the markets. And I think I'm excited for that. I think it's going to be a really positive thing for industry. The other great thing is I can dub over you saying Harvey and slice and LaGoura for the totality of that. And so we don't have to give any plugs to, you know, to hearty throughout this. It's a great market. No, it's a great example too, though. I'm curious, like one of the things that I've thought about with your example, and I'd be curious what you think of this is like, this some extent, the outcome-based pricing in general is so demonstrable ROI. And it's very clear what people are willing to pay for it in some ways. And also, you're somewhat beholden to alternatives in some ways. And so I think about what value I get from Zoom. And if Zoom was the only thing that existed in the world, I don't know. We could probably get Red Point to pay $10 million for it or something, right? Just because it's like that impactful to our day to day. But they don't get to charge that because there's teams and there's Google Meet and there's there's other stuff like that. And so I guess as you think about outcome-based pricing for your business or for Harvey and LaGoura, like doing work in that way, is there any framework or like how do you think price pressure plays out in some ways when there are these alternatives that can exist? Do you think that it ends up eroding some of the the ROI pricing that you can get in the early days? I have a slightly different way of thinking about it, but I'll try to answer your question directly too. You can reject my question. No, it's like really obnoxious. That's a different question. I think part of the reason that there's price compression for tools like Zoom or Slack and Teams is in part because the value you get from a sort of horizontal productivity tool is very hard to measure. If you just think about running a 120,000-person company that's a global company, you're paying per seat for something like a Zoom or a Slack or something. It's sort of funny because you're paying the same value per seat for like the most sophisticated research and development engineer and like the new grad in your pick the least strategic department of whatever that company does. As a consequence, I think when you're thinking of horizontal software, whether it's productivity software, communication software, you end up with pricing that is somewhat commoditized and there are some rare exceptions where companies are able to charge premium. In contrast, if you look at the enterprise software market that are oriented towards departments, say service now for ITSM or Salesforce or CRM or SAP for ERP systems, the value that those companies derive per seat for their application is traditionally much larger, usually more than an order of magnitude of software like Zoom, even though many fewer people use it, but it's closer to business value. You know the value of balancing your company's ledger and auditing your financials before earnings call, you know the value of a sale. As a consequence, the business value you're selling is more…
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