In short
The CMO Podcast: Episode Summary
Episode Title
- Expedia × Profound | Competing in an AI-Driven Search World
- Guests: James Cadwallader (Co-Founder and CEO of Profound) and Daniel Shin Un Kang (Head of Organic and Agentic Search at Expedia)
Episode Overview In this episode, Jim Stengel hosts a discussion with James Cadwallader and Daniel Shin Un Kang about the transformative shift from traditional content creation to AI-driven search. They explore the implications of this shift on marketing strategies and how brands can navigate the new landscape dominated by AI answer engines.
Key Themes and Discussions
The Shift in Content Creation
- From Humans to Machines: There is a significant transition from content designed for human consumption to content that caters to AI and machine algorithms. This change redefines how brands must create and distribute their content.
Insights from the Guests
- James Cadwallader:
- Founded Profound to assist brands in navigating the complexities of AI-driven discovery.
- Emphasizes the importance of understanding how brands appear in AI systems like ChatGPT and Gemini.
- Daniel Shin Un Kang:
- Leads organic search at Expedia and focuses on redefining search in an AI context.
- Highlights the challenges in measuring AI visibility and traffic.
The New Era of Search
- AI Search: The evolution of search mechanics is driven by AI, making traditional SEO metrics insufficient. Brands must adapt their strategies to maintain visibility and relevance in this new environment.
- Engagement through AI: With AI answering user queries directly, the way brands engage with consumers has shifted. Brands need to rethink how they present their information to be effectively surfaced by AI.
Challenges in Implementation
- Data and Methodology:
- The complexity of obtaining accurate data for AI search is emphasized, with numerous methodologies existing to measure visibility.
- The discussion reflects on the need for brands to choose the right vendor capable of providing meaningful insights into AI interactions.
Practical Advice for CMOs
- Invest in SEO Talent: CMOs should recognize the evolving role of SEO teams and empower them to adapt to the new landscape of AI-driven marketing.
- Focus on Continuous Learning: It’s crucial for marketing leaders to place emphasis on understanding AI technology and its implications on their business strategy.
Future of Advertising
- Generative Ads: The potential for AI-generated advertisements to personalize marketing efforts significantly is discussed, predicting a transformative impact on how brands interact with consumers.
Takeaways
- Understand the Shift: CMOs must educate themselves on the challenges and opportunities presented by AI in search and marketing.
- Empower Teams: Create dedicated roles within marketing teams to focus on AI and emerging technologies, ensuring the organization remains competitive.
- Continuous Adaptation: Recognize that marketing for machines is an ongoing process requiring flexibility and innovation.
Conclusion This episode serves as a vital resource for CMOs and marketing leaders to grasp the current landscape of AI in marketing, urging them to adapt their strategies in light of this transformative shift. The insights shared by James and Daniel, combined with Jim’s guiding questions, provide a compelling narrative on the future of marketing in an AI-driven world.
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This summary encapsulates the essential discussions from the podcast, highlighting the pivotal topics that CMOs and marketing professionals should consider as they navigate the evolving digital landscape.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOBrand Impact Memories
0:55 to 2:18
Guests James and Daniel discuss impactful brands from their childhood.
“It's the first brand you remember making an impact on you as a young boy.”
Super Bowl Ads Discussion
3:40 to 4:48
The hosts discuss whether their companies will have ads during the Super Bowl.
“This episode will really make you think.”
Meeting Origins of James and Daniel
4:48 to 6:04
Daniel shares how he and James first met through professional networks.
“So I knew of James far before James knew about me.”
Challenges in AI Search Metrics
6:04 to 6:52
Daniel explains the complexities of measuring success in AI search.
“And it's actually quite complex for a couple of reasons.”
James on Daniel and Expedia's Approach
6:52 to 9:41
James praises Daniel and shares insights about Expedia's marketing sophistication.
“And that's why we got started with them.”
Daniel's Perspective on Founders
9:41 to 11:41
Daniel reflects on his experiences with founders and the respect they earn.
“But that's my impression of Expedia and Daniel.”
Founding Profound: Insights and Origins
14:02 to 18:36
Discover the inception and foundational insights behind Profound and its relevance in the AI landscape.
“It was founded in August, 2024, not that long ago, but could you take us back to then?”
The Journey of the Last 18 Months
18:37 to 21:46
James reflects on the significant personal and professional developments over the past 18 months at Profound.
“I mean, you had to say, well, no one's talking about this.”
Daniel's Transition to Expedia
21:47 to 24:15
Daniel shares his recent experiences and the lessons learned from launching a startup to joining Expedia.
“My fiance always laughs that, you know, if I'm relaxing on a Sunday afternoon, We work pretty hard here.”
Collaboration Between Profound and Expedia
24:16 to 27:44
Explore how Profound and Expedia are partnering to navigate the evolving search landscape.
“So I started my company in mid-late 2021.”
Show all 25 chapters
Understanding AEO Visibility Challenges
28:00 to 29:50
Explore the complexities of achieving visibility in AI-driven search platforms.
“When it comes to AEO visibility, it's important for everybody to understand again where you are and what metrics are going after.”
Navigating AI Search Inputs and Outputs
29:50 to 32:55
Learn about the four key inputs affecting brand visibility in AI search.
“And where we're working together very, very actively is the synthetic prompting and the vendor methodology.”
The Shift from Human to Machine-Centric Content
33:34 to 36:30
Understand the implications of creating content for AI user agents rather than humans.
“Learn more about the CMO program at cmo.deloitte.com.”
Strategies for Content Scale and Quality
36:30 to 39:52
Explore how brands like Expedia manage large volumes of content successfully.
“And you need great technology to understand how that content is performing at scale in these new AI surfaces.”
Collaboration Between Profound and Expedia
39:52 to 41:44
Learn how data insights from Profound support Expedia's marketing efforts.
“it's not necessarily going to be aimed at humans, but yeah, that's where we see things going.”
Assessing Brand Visibility in AI Search
41:44 to 42:00
Discover tools for brands to evaluate their presence in AI-driven search environments.
“Do you think we'll ever get to a point where there will be a way for us to assess how we show up as a brand in the AI search world.”
Understanding User Agent Data in Marketing
42:00 to 45:30
Learn how user agent data can transform marketing insights and strategies.
“And I want to have an idea to, am I behind, ahead?”
Vive by Vayner: Empowering C-Suite Growth
45:31 to 46:20
Discover how Vive's program helps C-suiters grow their businesses and personal development.
“I'm Andrea Sullivan, the CEO of Vive, and we have produced the CMO podcast with Jim Stengel for many years.”
Counsel for CMOs in an AI-Driven World
46:21 to 49:21
Gain insights on how CMOs should adapt their strategies amidst AI advancements.
“We're living through the biggest change in the internet since we've known it, right?”
The Evolving Role of SEO in Modern Marketing
49:22 to 50:39
Explore the transformation of SEO into a crucial component of digital marketing.
“There's an ongoing debate around, you know, SEO versus AEO, GEO.”
The Future of Advertising and AI Integration
51:11 to 56:00
Understand how AI is reshaping advertising and the challenges it presents.
“I mean, that seems to me to be a very significant change.”
Academic Journeys and Survival Strategies
56:00 to 57:39
Learn about the academic backgrounds and survival strategies of the guests.
“I think Stanford is, I think it's a very exciting place.”
Influential Brands from Childhood
57:40 to 59:18
Explore how childhood brands shaped the guests' aspirations and identities.
“You know, this question is coming if you listen to our show.”
AI in Marketing: Tools and Experiences
59:19 to 1:01:08
Discover the AI tools the guests use and how they enhance their work.
“And there's specific software that is just better on the Mac and sound and plugins that are just better.”
Strategic Recommendations for CMOs
1:01:09 to 1:02:38
Understand the strategic recommendations for CMOs in the evolving marketing landscape.
“It's a build into everything I do, right?”
Transcript
Automatic transcript. May contain errors.0:00Hey, everyone. Jim here, and I've got some exciting news. The CMO Podcast is now on YouTube. You can now watch our conversations, not just listen. See the expressions, the energy, and the insights that happen when we sit down with the world's top marketing leaders. Head over to YouTube and subscribe to our channel, The CMO Podcast, so you never miss an episode and be part of the community. So please check it out, subscribe, and join the conversation. What if the smartest marketing play is not to move forward, but to zoom out? Deloitte believes the most powerful move a CMO can make is to look beyond the next step and see the broader perspective.
0:37That's what the Deloitte CMO program is for, a place to gain fresh perspective and connect with leaders who've stood where you stand. Together, Deloitte will help you see the bigger picture so your next move isn't just fast, but right. Learn more about the CMO program at cmo.deloitte.com. It's the first brand you remember making an impact on you as a young boy. James, start with you. I was big into soccer or football, as we would call it. Correct me. I agree with that. They're these David Beckham Adidas football boots. I can just remember it being so visceral and needed to own that pair of football boots.
1:15So Daniel, how about yourself? I think the biggest brand is probably Apple. Growing up, like in the middle of the farm, middle of nowhere, like getting exited stuff hard. But then when I first came across like an iPhone and I said, wow, that's pretty incredible. I wonder what it can do. And it's had a thing for me since I was a kid. And I'm finally able to use some Apple products. I'm very happy. Hi, I'm Jim Stengel. I've helped hundreds of major brands discover and activate their purpose. Because when a brand's purpose is clear, compelling, and authentic, profit naturally follows. Each week, I welcome the CMOs, the chief marketing officers of your favorite brands, to speak to how their job is so much more than marketing.
1:52These leaders share their inspiration and challenges along with how they try to build a full, healthy, and happy life in and out of the office. And it's that energy that reaches everyone they touch. And we're glad you're here to feel that energy and to learn from these remarkable leaders. So here we go. This is an especially important show today. We're living through the largest change in the Internet since its existence. the shift from building content for people to building content for machines on behalf of people. In short, the rise of AI search, the shift in how we retrieve information about everything.
2:29My guests today are at the leading edge of that shift, and we will explore a case study on how to operate in this changing world with its implications for CMOs and frankly, all players in the marketing ecosystem. First, we have James Kotwalader, the co-founder and CEO of Profound, a fast-growing new company helping brands understand how they show up and compete in AI-driven discovery. James works with companies like U.S. Bank, Chime, Expedia, and DocuSign in navigating the shift from traditional search to a world of answer engines, agents, and AI-led experiences. James founded Profound in 2024, has already raised about$60 million.
3:06His company has been recognized by Redpoint Ventures as one of the most promising private AI companies shaping the future of applied artificial intelligence. Joining James will be Daniel Shin-ong Kong, head of organic and agentic search at Expedia, one of the world's largest travel platforms, serving millions of travelers globally and generating more than$12 billion in annual revenue. Daniel leads teams working at the intersection of search, AI, and customer experience inside a large, complex, performance-driven organization. Together, James and Daniel bring two powerful perspectives. This episode will really make you think.
3:42Let's get into it. A conversation about search, AI, and indeed, the future of marketing. Well, James and Daniel, welcome to the CMO Podcast. I am super looking forward to this. We're recording this right before the Super Bowl. Now, Daniel, I know you're not super into sports, but I do have to say, will either one of you two have an ad in the Super Bowl this year? I believe Expedia will have an ad, but let me correct, make sure I'm not lying to the audience. Okay. He's looking it up. That's good. I suspect you will as well. I see Verbo everywhere in sports. So how about you, James? Profound Super Bowl ad this year, maybe next year?
4:20Yeah. Despite being a well-funded startup, I don't think we are at Super Bowl territory yet, especially considering we are predominantly B2B. So yeah, no Super Bowl ad this year. It's a matter of time, right, James? A matter of time, yeah. Inevitable, but just not this year. Okay, guys, let's move from the Super Bowl and let's start with how you two met. I mean, we're going to talk an awful lot about this case study today of Expedia and Profound, but how long have you known each other? So I knew of James far before James knew about me. So he's part of a community in San Francisco called South Park Commons.
4:56And when I joined, I think summer or so, we were talking about who are some of the top performers in this community and James's name, of course, profound came up a couple of times. So he was on my radar for quite some time. But my story is I had joined Expedia originally as an entrepreneur in residence and then a few months after became a P &L owner for the organic and agentic search. And as we were going through that as a practitioner, one of the obvious problems that comes up is how are we doing? And that's a surprisingly hard question to answer in terms of AI traffic and AI visibility. And of course, out of the 15, 20 companies that are working on the space, I talked to a lot of them and James was already in conversation with Expedia at the time and Profound is obviously the category winner.
5:40That's how we got to meet for the first time. I think our first real call was around contracting terms. And then after that, we had a couple of other sessions. Fun call. So Daniel, I'm going to ask you a really stupid, naive question. Why was that important for you? How are you doing Expedia in AI search? Yeah, it sounds like an obvious question, but you have to know where you are in order to help get the bearings of where you want to go. And it's actually quite complex for a couple of reasons. The first is unlike traditional search with a mature ecosystem of data and players, you don't actually get a lot of data services or ground truth.
6:16So I don't think anyone knows exactly what queries users are typing in when they're searching for brands like Expedia and otherwise. So what the industry has done, for the most part, is create synthetic prompts of what do we think users are going to ask these large LLM search engines and scrape sort of the data and then get a proxy of where the industry is going. This is a really, really hard problem to do this at scale. You can imagine doing this dozens of times on a single platform. Now multiply that by 10, 12 different models that are out there and thousands of prompts becomes a nightmare. And this is why I think players like Profound exist.
6:53And that's why we got started with them. Now, I want you to talk about your first meeting was about a contract and then you moved on to more fun stuff. So our audience is getting to know both of you. So I'd like you to talk a bit about each other and maybe James, you start, talk about Daniel a bit. What inspires you about him? What strikes you as a person, as a leader about Daniel? I mean, I think, well, I can speak to Expedia as a whole. So Expedia as an org are one of the most sophisticated teams in this category right now. I guess as quick, fast background, I'm James, co-founder, CEO of Profound.
7:28Yeah, we launched the business about 18 months ago in August of 2024. It's been a rip-roaring journey of, yeah, it's been exciting and fun and mayhem, all things together all at once. But on this journey, what's ended up happening is we now work with, I mean, and it's a true luxury, it's a true honor, we work with the biggest brands in the world, like quite literally, I think it's dozens of Fortune 500 companies. And you get very good exposure and start to understand which marketing teams are super sophisticated. Now, unfortunately, it makes it sound like I'm just sucking up to Daniel, because I can only really talk about Expedia on this call, because Fortune 500 companies don't want me sharing their, you know, who's doing what, but I can say that there's probably half a dozen that really spring to mind.
8:15And within that half a dozen, I'd say Expedia is probably in the top one or two in terms of their, how much the team is leaned into this category, how sophisticated they are. I went over to the Expedia HQ in Seattle and sat with the team as they spoke about AI search as a category and left blown away by the level of sophistication. The level of granularity, the amount of content that is created and hosted on Expedia is once you really pay witness to it, you're like, whoa, this is a really big operation. And you can see a business that has been built on an incredible approach to marketing, one that I've never seen before.
8:55And now Daniel within that, I think is unique in that he comes from a tech background. So Daniel comes from, you know, he doesn't really come from, you know, your traditional marketing background, but he really has a kind of like hacker mindset and a very tech forward mindset. I mean, that speaks to his time at South Park Commons, which for anyone who's not familiar is like a SF based accelerator incubator program that was set up by two of the founding engineers of Facebook. It's pretty hard to get into. I mean, I say that as someone that was accepted, so it sounds a bit self-congratulating, but it's pretty hard to get into.
9:29And I think once I pulled two and two together and I was like, oh, wow, that's Daniel from SPC. That's crazy. You're now Expedia. That is a very unique offering and it all kind of marries together and makes a ton of sense. So, yeah, long answer. But that's my impression of Expedia and Daniel. So, Daniel, you knew about James before he knew about you. So now that you're working with him and you're getting to see the real thing, you know, does he inspire you as much as he did before you knew him? there's only one there's only one answer to that question i don't know about that only one correct yes that's right i i think for sure so i'll talk a little bit about my background and it matters in this context of how i perceive james so my background is i used to be a venture growth investor at softbank vision fund so i invested in top growth equity companies for about two years sat on boards and sort of helped them with their pre-ipo to ipo sort of phrase and And then I said, maybe I could build one of those companies like any delusional founder.
10:25So I left that job, started my own company with a different accelerator called Y Combinator and sort of scale that company to some time. The reason I mentioned this is before you dive into even as an investor looking inwards to founders, I don't think every investor quite understand what it's like to be a founder until you're a founder yourself. And having been in that seat, I have first tremendous amount of respect for founders who are actually building in this frontier technologies. They saw something that are non-obvious to other people at that time and then actually executed. So I think that's really, really big.
10:58And I think Profound and James with his co-founders, actually one of the very first who was to really pioneer this industry. So I think that speaks to a lot. SPC, again, a little bit of a sycophatic thing. But yes, I think it's a great program as well. But the way that James responds to problems, like in the early days, a founder is heavily focused on building what customers want. And the rate of response, how quickly he responds and how thoughtful he is with all of these is just a testament. The fact that he actually flew over to Seattle, spent, I think, what was it, James? Like eight, nine hours, something crazy like this, where he was locked in a room.
11:36just how much it cares about customers. And I would be very bullish on this company. I appreciate that. I mean, one thing I'd add a bit of color to that, which was quite interesting. So you go to Seattle, it's myself and Kendall from my team who's worked super closely with the Expedia team. I don't know. I mean, maybe I was missing some context, but we were working with Alistair from your team, Daniel. And Alistair, he's a super smart guy, but like very nonchalant, like kind of brings us into the lobby, gives us a tour. And he's like, oh yeah, we're going to go into the meeting room. But I thought it was going to be like a few, you know, a few folks sat around like drinking a coffee or something.
12:09I'm just like super casually. We go walking around this corner and I walk into this room. No word of warning. No, like just Alistair. I'm just following Alistair around the corner into this room. And I kid you not, there's about 25 people. It looked like one of those, you know, like a president's briefing or something. It was like this giant horseshoe shaped table arrangement with about 25 people all sat waiting for us to walk into the room. So it was a bit of a shock to the system that day. But yeah, it was about eight or nine hours in that room going through the details. Yeah. Well, I know from my homework on you, James, you don't have a lot of hobbies.
12:45You love business. You love work. So this is all fitting together.
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14:02So, listen, we're already kind of going here, but I think as context for the discussion about how you two are working together in this little case study of Profound and Expedia, we need to have more context on your company, James, and you're sort of already going there. It was founded in August, 2024, not that long ago, but could you take us back to then? What was the insight? What was the problem you're trying to solve? Why the name you chose as Profound? Walk us through the garden of the history of your company a bit to give us context for what we're going to talk about in the work you're doing with Expedia.
14:36Yeah, for sure. It's interesting. I think, I mean, particularly over the last six months, I've actually had a few people say to me in reference to the, you know, the inception of profound, like, you know, wasn't it, it was a very obvious idea or people will introduce, you know, people enter a conversation saying, you know, it's a very obvious idea. But back in at the beginning of 2024, it was so non-obvious. It was a very, very peculiar paradigm because it was myself and my co-founder, Dylan, who was a software engineer at Uber working on geospatial products. So lots of map building and building the rider app experience.
15:14And we were exploring lots of ideas. I was very interested in search, generally speaking. Somewhat on the consumer side, I was interested just in information retrieval and what I think really perplexity was pioneering in information retrieval was becoming more and more interesting. And really our business was kind of thinking of a second order effect where once you start to, I mean, if you've read books like The Search or, you know, Into the Plex or, you know, even Chaos Monkeys to an extent, and you've studied the origins of search or the origins of Google, which is kind of synonymous with search, the thing you begin to understand is that search or search engines, i.e.
15:59Google search, is the biggest outcome really in the history of capitalism. And that outcome is predicated on this idea of we will give you links and you will click them and then we will pepper in some paid links and you might click those as well. And now we have this platform shift with the birth of chat gpt and generative ai which counter positions entirely against that idea where you no longer have to click anything you can just talk to the internet and it talks back to you so in that new world what happens to the click like it undermines the entire business model of blue link search which really is the biggest outcome in the history of capitalism so once you start to realize that Like it was this like, I mean, it sounds a bit dramatic, but dare I say sublime kind of like, it was almost overwhelming at the time to realize it was like, wait, surely not.
16:59This can't be real. Do you know that movie, The Big Short? Sure. Do you know that feeling they capture so well where they're like rubbing their eyes? They're like, surely not. This can't be real. Why is no one else talking about this? That was the feeling as we were, because you know how obvious this is now, this space As you said, there's a new AEO tool that pops up every week and YC is back to like 10 in the space. And it's a very highly spoken about, extremely obvious category now. Imagine it being that obvious just to one person at the beginning when no one else was talking about it. So there's this like big short moment in the very early days.
17:38And you really had to resist the urge to just, you had to resist the urge to second guess yourself. because it just felt like we had to be right. Surely not, because this is the biggest outcome in the history of capitalism. Surely not. And why is no one talking about this? But we just went all in. And our idea is that in a world where you can talk to the internet and it talks back to you, or when AI answers your question, the only thing that will matter to marketers is how AI talks about your brand, how AI talks about your product or services. And AI has to get that information from somewhere.
18:10It doesn't rely on the pre-training. It can't rely on the pre-training. So it has to pull from the open web information on the open web. So now how you distribute content, ideas, information to bots on the internet that are crawling on behalf of AI systems like ChatGPT or Gemini or Grok or Meta becomes the most important priority in the history of marketing. So yeah, that was kind of a meandering, I don't know, glimpse into maybe how we were thinking back at the time. So there's that provocative thought, insight, rubbing your eyes. But then what did you do? I mean, you had to say, well, no one's talking about this.
18:46We should. This is a massive problem for every brand, right? So what role can we play in helping brands solve the problem? How'd you make the next leap? I mean, then we went to war. It felt like, you know, it was almost like you spend some time in the, you know, that with everything prior to this point in the story had been like more, you know, the exploring the blue ocean thinking, the what if. But once we crossed a certain threshold of conviction in the idea, it's like an entirely different mindset. You essentially put on your helmet, you grab your rifle and you go into the trenches. It's left foot, right foot, left foot, right foot.
19:29And it's just quick reps. It's okay, let's go and speak to some of the marketers that I know. Johnny Bentwood at Golan got introduced to him before we had anything. We had a PDF and he was super supportive. And there's all these kind of miracles, these mini miraculous moments along the journey, like as you had a hope and expect. Like, you know, we met Johnny Bentwood at Golan who didn't know us particularly well. I just got introduced to him through someone else that I worked with. But instantly he was like, that's a great idea. That's a great idea. We'll give you a$15 ,000 LOI, which to us at the time when it was just a PDF was like Like that was a crazy opportunity.
20:05We were like, wow, there's someone willing to pay 15 grand immediately. And then it's like, okay, well, Johnny, what do you want? And he's like, oh, I want it to look like this. And I want it to do that. And you just rep and rep and rep and rep. And my co-founder, luckily for me, I think Dylan is one of the best product engineers on the planet. He's very talented at what our type of business is. He's not, you know, he is not a scientist working a deep mind on neural nets, but he is incredibly good at building product. And he likes building product. He thinks products fun. So once we started repping, it was, you know, then we found Charles, our founding engineer, who again, in a miracle moment, he had written a dissertation essentially on this exact topic and then gone to Omnicom, which is where he was working at Omnicom and he was bored out of his brain there.
20:49And one of the biggest holding companies in the world in communications just for our audience. Yeah. I would say Omnicom is not known as a hub for the best engineers in the world. Put it that way. I know that. Yeah, for sure. it's it's not like hiring someone from deep mind where it's kind of figured out and obvious but charles our founding engineer was at a funeral of a mutual friend with one of our mutual friends and they were like they were talking about our business he was like so i'm literally thinking about that right now so then three days later he jumped on a plane from chicago and came down to new york and the rest is history there's all these mini miracles on the journey yeah so good so So Daniel, I'm going to bring you in in a minute, but I want you, James, just for a moment to reflect on the last 18 months in your life.
21:33I mean, this has got to be the most important thing you've ever worked on, maybe that you will ever work on. Yes. Tell us a little bit about what these 18 months have been like for you as a human being, an individual, a person, a guy who loves business. Yeah. I mean, I definitely identify as like a disciple of business. I find it interesting. My fiance always laughs that, you know, if I'm relaxing on a Sunday afternoon, We work pretty hard here. I'm in office six days a week. And then Sundays, even when I'm at home, I'm quite often on my phone or doing stuff anyway. But my relaxation would be watching a podcast like yours, Jim, or maybe reading a great book on...
22:11I don't know. I'm trying to think like some of the aforementioned, listening to the Acquired series on Google. So I'm a disciple of business. And yeah, I think this is the most fun I've ever had. I don't want it to stop. And I, yeah, work. It's like the universe has given us this gift and the only way to reciprocate and pay it back is just to give it everything you've got. So yeah, I think, yeah, and you're right. I don't think I'm going to get another opportunity like this. I want to work on this until I die. So Daniel, react to all that that James just said. What's buzzing around in your mind as he goes through that?
22:50I think you call it a gift. I think it's a humble way to put it. To your point very early on, James, it was obvious to you. And I think that's the benefit of being around a community that's forward-looking, where non-obvious things become obvious. But there are very few people who actually act on that. So I don't know what path you took to arrive on that conviction. But once you got into conviction, you said now it's war, right? And And very few people are able to execute on that level of conviction because you literally bet your life on it when you had nothing and your first win was a 15K LOI.
23:19And like, let's be honest, 15K LOIs, not even a real contract. It's not a recognizable ARR metric. It's a document, right? But the fact that you're able to put left foot, right foot forward and just progress is fantastic. And yeah, I'm and it goes back to, you know, the side story of like how responsive James, he's a co-founder, right? of this large org, but he's still yet extremely responsive because he's working. He cares about customers. He's looking to see where can we go next. And I think there's tons of products in the pipeline, James, I'm sure that you have that reflect a lot of the needs of the customers.
23:52So I'm again, very, very happy to have met a founder who is in this pioneer of this category and glad that we get to partner. Well, Daniel, your last 18 to 24 months has been also interesting, right? Right. You did a book, you launched a book, The Super Upside Factor. You joined Expedia in 2025, head of organic and agentic search. So talk a bit about your life the last 18 to 24 months. How's it been? Yeah, it's been a little bit of a whirlwind and a lot of learning experiences, I would say. So I started my company in mid-late 2021. And it was a company that wanted to allow financial services and access to as many people as possible, starting with freelancers and creators.
24:33And we were on a great trajectory and working on it for quite some time. But three or four years into the journey, I had one, gotten very tired. And two, there are many macro shocks into the business where we came to a decision that it is not in the best interest of us, the investors, or the customers to continue this company. And we still had, it was a really hard decision because Because we still had over$2 million left in the bank. We're at the biggest platform shift we've seen forever. I think everybody agrees this is probably one of the best times ever to do a startup. So walking away from that was quite hard.
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25:07But we didn't think the motivations of not wanting to look like a failure or continuing just because we can was actually a very good decision for anyone involved in the party. So we made the decision to shut it down, return the capital, and I took some time off. And as that was happening, my book was released, which was really, really tough because on the face of it, I had to show, hey, I'm doing really well. It's successful. The book actually talks about applying venture math to careers. So the crux of the book is there's a trillion dollar industry that's paid to be wrong. So venture capitalists lose money about half the deals they make, and they miss the mark 90 % of the time.
25:45But if in the few times that they win, it's a 5 ,000x return, as we've seen with, you know, Masa's investment in Alibaba or Index's investment in Figma. I think Figma was a 6 ,000x return or something like this. You can still win dramatically, even if you're wrong most of the time. And how do you sort of apply that into your career? And, you know, got to talk about this in the stages of TEDx Stanford. But internally, as you can imagine, was I had just killed my baby of a startup and going through that. And I said, maybe I need to take a break from entrepreneurship for a little bit. but oddly enough, joined Expedia as an entrepreneur in residence and also got into the future of search a little bit more.
26:22Where is search evolving? So AEO was a big topic even when I got there and not formally involved. But I was thinking, all right, where's this thing going? What about the ads? What about the agent of commerce? What about all of these things? And I thought deeply about what I call probable future states. So rather than what will happen, what are the ranges of futures that would happen? and how would we, as Expedia or anybody else, position ourselves to these probable future states so that we're in an advantage. So as I was thinking through that, an opportunity came up where they said, hey, well, we really like your work.
26:54We think this is interesting. Can you go and actually run this P &L? So I think it's been, what, three and a half months now since I've been running this. So everything is very, very new. I'm getting tons of help. I'm learning a ton from, again, practitioners and operators at this frontier like James and like others who are building. Now, let's get into what you are working on together, what your companies are working on together. So, and I would love this as much as you can be transparent about it and open to be a bit of a case study on James, what your company does to help brands and Daniel and what your company does to work with a team like Profound to understand what's going on in our ecosystem, especially around things like AI and AEO or answer engine optimization and leverage it to build your brands and grow your share and make earnings and have a great future for your company.
27:45So I think we should start with what are you doing? What's the scope of your relationship right now? What's the scope of the work you're doing? I'll kick off and set a little bit of the context of what visibility means and where we're going and where we're working together and where we want to, or I'll speak for myself, or I want to continue to work together. When it comes to AEO visibility, it's important for everybody to understand again where you are and what metrics are going after. It's actually a surprisingly hard thing to crack. And I'll talk about at least three major complications. The first is, again, to set context, no ground truth.
28:18You have to synthetically prompts to get a proxy of what consumers are seeing on their screen and then try to get in front of them. So on the visibility front, there's a couple of hard problems you have to solve. The first is getting to the right set of prompts. How do you know that this thing is actually reflective of what consumers are searching? So how do you do that? The second is actually choosing a vendor and understanding their methodology. So Profound is one of them. There's like 15, 20 plus companies that are doing this with different methodologies. An example of this is even in the prompting stage, some companies prompt using a headless browser, others use an API, and some have like some memory enabled.
28:55These small methodologies actually creates a large variance in the actual outcome that we see on the outside. So how do we resolve that? And what is the best methodology that best reflects what happens in the real world? And then the last thing you sort of have to think about is once you get this raw output, and by the way, this is like another technical hard thing you have to do. But once you get that raw output, you then need to derive a visibility metrics. When people say visibility, what does that even mean? Is that like a rate? Is that a share of voice? Like, what does that mean? And when you say visibility, it's your brands, right?
29:25That's correct. And how is this actually correlated with AI traffic, right? Because at the end of the day, yes, brand exposure is important. All of these is important. But for a consumer brand like ours, getting that revenue and getting that transaction and making sure it correlates is important. Otherwise, you're optimizing with the wrong variable. So there are like three really hard problems to solve. And I think, you know, internally, we've done a great job of this with the help of our partners. And where we're working together very, very actively is the synthetic prompting and the vendor methodology.
29:55I think Profound has done a good job of understanding the trade-offs and coming up with the methodologies and also giving guidance on how to think about even the prompting and scraping of the information. I'll give you one very concrete example. When prompting, some vendors choose to prompt via the API. And there's a lot of business benefits to that. It's cheaper. It's scalable. It often breaks less. You probably need less stuff to scrape the data. but I don't think it's as reflective of what consumers actually go through. So despite the fact that it's more expensive, that there's a lot more operational overhead, you know, Profound has chosen to take this methodology for that accuracy, right?
30:35So these are like the snippets of examples of why, you know, working with a partner like Profound is helpful. For a non-technical person, what is the exact business problem that you are trying to solve? And you say it's visibility of your brands, but take that a step further. Okay, so basically you want to maximize in a new platform shift to maybe relate to James's view. Google used to show a bunch of links and route people to different pieces of information. AI search engines ingest information and then share the most relevant. How do you show up as a part of that? And whether it's in brand mentions or links.
31:11So you want to know how much where you are showing up when you're not showing up. and then constantly optimize your stuff to be able to go do that. And I can expand a little bit further of how AEO is a simple but a hard path to success. Essentially, you want to get into one of four inputs. The first input is the training data. And that alone isn't enough, but you do want to be included in somehow. The second is a retrieval process. So when a user types in the queries, it looks at the model, but sometimes it gets snippets of information from the web and then surfaces it. The third is outside your direct control, but you want customers to actively query your brand into their queries and then you show up in your context window.
31:54And the last thing is, as these things compound, whether users mention your brand in their query or the output contains your brand, this gets consolidated into your user memory and will be referred to. And if you can maximize that, you get a compounding effect of your brand increasing. So you want to be included in one of those four inputs. The way you do that is through two things. The first is technical enhancement. So is our content even discoverable is like a big one. And then the second is worthiness. Is your content worthy of showing to our end customer? So when you look at those two things, there's a ton that you could do everything from file types like markdowns to make sure that bots are able to access your stuff.
32:33And it turns out different bots react differently to different file types, right? Or do you even recognize what bots are crawling on your website? All this technical stuff. And then the content is, of course, is it relevant? Is it trustworthy? Is it actually useful to the end user? So it's simple in a sense that there's four inputs and you have two levers to get there, but getting there is actually pretty hard. And visibility, of course, helps you understand where you're missing, what is working and what isn't working, right? When you're trying to optimize these two levers.
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33:41James, I want you to talk a bit about how you're helping with those business problems, but I love the quote that as I was looking at video of you, James, before we started, and this relates to what Daniel just said, we're not building content anymore for human beings, right? We're building content for user agents on behalf of consumers or human beings. That's such a profound shift. And Daniel, I think everything you talked about was about that shift. And at the end of the day, you have to have things that are built for the bots, but that people really need and want. And that must be very, very tricky to manage.
34:15So James, could you talk a bit about your company in terms of how you're helping Daniel solve that very enormous opportunity slash problem? Yeah, I think the point you make is a good one in that it's just true that you are creating, I said marketing to machines, really, that's the idea, right? Because if I asked ChatGPT a question about where's a good place to go on vacation for my honeymoon in the Bahamas you know where does chat GPT go to to answer that question does it use the pre-training that Daniel mentioned or does it trigger a web crawl because it hey it said you know I said give me the latest hotels or find me something very specific that the pre-training doesn't feel you know the classifier would say the pre-training probably can't answer this so then okay well does it it's going to run a bunch of web searches and it will surface likely some Expedia results, then how does that content get pulled through?
35:08Because the content, a lot of the content was designed for humans. Now, I won't overshare out of turn, Daniel, just in case I'm making you nervous on the other side of the screen. I won't share any secrets. You guys have a lot of sophistication around what you do. But I mean, I think one thing that is kind of obvious about Expedia is they just have huge volume. Daniel, can you speak to any of the volume that you have in terms of web Because that was one of the most fascinating things that I discovered through our partnership is just the sheer volume of content these guys have is just hard to wrap your head around sometimes.
35:41Exactly. And picking a partner that's able to work at that scale was hard. We're talking hundreds of millions of assets, right? So try optimizing that. You'll talk to this, but you're going to need a machine to be able to do this. Yeah. I mean, so it's enormous quantities of content. And I think for what it's worth, there's two ways to interpret that. You could just interpret it as the, you know, Expedia is N of one and content is their business. So you'd expect them to have hundreds of millions of pieces of content. I also think there's, and it sounds like sycophancy, but I think there's an argument just to say that they're a very sophisticated team and that they are pioneering the future of content marketing.
36:20And actually most businesses will catch up, maybe not to that same order of magnitude. But I think businesses are going to create a lot more content. Put it that way. And you need great technology to understand how that content is performing at scale in these new AI surfaces. So if we ask, you know, 100 ,000 or a million questions about vacations in the Bahamas, how does Expedia get pulled through both as a brand and as it's mentioned, but also does it get cited? Is it going, you know, are the models using Expedia.com or, you know, jimsvacationblog.com to answer these questions. And that varies from platform to platform.
37:01So really giving the team visibility into not just how they show up, but also the why. You know, why do you show up here? Why don't you show up here? And then a place that I think we, I mean, candidly without, you know, I don't think this is super confidential or anything, but I think a place that we're excited to lean in more with the Expedia team is on sentiment as well, which is kind of like a new vector. Sentiment didn't really exist in the world of traditional search because as we've spoken about, Google search was just surfacing links. There's no sentiment attributed to a link. But think about it like this.
37:36If I ask ChatGPT, what are the best marketing podcasts in the world? It will say something about the CMO podcast, but it will give an opinion as well. It will say, Jim always gives hot takes about XYZ, XYZ, but sometimes it misses the mark on this and this. So you're getting an opinion for free. And that opinion varies and evolves over time. When you're running hundreds of thousands of prompts every day, you start to see the drift of that sentiment starts to change over time. And then you can attribute why that sentiment is changing. So it's a new surface area. I think really what this comes down to over time though, which is going to be, when I was watching, I was actually watching a fantastic podcast with Winston, who's the founder of Harvey AI, a completely different category of business to ours.
38:26But he was with Brian Halligan, who's the founder of HubSpot as a new podcast. And Winston was on that pod. And he had this amazing quote where he said, you have to re-earn your right to play in the category every six months. That's like the new world of building software. And so the next six months for us are going to see a huge focus on profound winning content orchestration as well. Because what we see is that, you know, as Daniel mentioned, all right, cool, you want to update 200 ,000 pages. But now because of generative AI, we can and we can do it thoughtfully. We doesn't have to just be I think the headwind here or the the controversy is that, oh, that means AI slop.
39:12I don't think that's true. Slop is a function of context. If you give models tons of context, the output's amazing. Slop is a consequence of if I just said to chat GPT right now, create 10 ,000 blog posts for Expedia.com, it would happily do it, but it would suck. But if I give it tons of context and raw data and interesting inputs and unique insights, it does a very good job, or at least it can get it 90 % of the way. So yeah, I think Profound will become this workbench that different teams at Expedia use to orchestrate and automate production of quality content. It will start off as quite low lift, kind of, you know, the simple content, it's not necessarily going to be aimed at humans, but yeah, that's where we see things going.
40:00Daniel, what's James's team helping you do that you could not do yourselves? I think there's a central point of we oversimplify it by saying, hey, synthetic prompting. I think just get us the data. Here's the queries. And from a buyer's perspective, it seems like a simple ask. If you try to build it yourself, I'm sure it's technically very, very challenging to do, especially QA, making sure all the data pulls through, making everything and making sure everything's accurate. And to James's point, also do then start doing pattern recognition, right? of every search engine actually rewards different things, whether it's AI mode or Gemini or Chachapiti, Claude, they value different things.
40:39The sentiment on it is going to be different. All of these things are something that is, I think, probably very distracting to a company that is doing something else. In our case, meeting travelers where they are. We don't want to spend all of our time doing this. This is something we need to help diagnose the problem and start optimizing our content and our technicalities. And this is where Profound is helping. And to James's point, I think, as we go forward and we integrate further, it would be great to sort of, how do we think about content production and QA? Of course, we have our own engines, but I think there are different areas where we can play together.
41:13I think there's a heuristic to that as well. And it is a heuristic, but I think you could also just take the simple point that we've got close to 50 engineers or folks working in engineering product design data now, working full-time on this. And by full-time, I mean mostly six days a week, long days, long nights, and have been working on this for a year and a half, day in, day out, day in, day out. And the product that we give to Expedia is the output of all that work. Do you think we'll ever get to a point where there will be a way for us to assess how we show up as a brand in the AI search world.
41:52You talk about sentiment, we're starting to understand that. But if I'm one of Expedia's brands, if I'm Coca-Cola, if I'm Toyota, I want to show up right. And I want to have an idea to, am I behind, ahead? Where do you think that's going to go? Yeah. I mean, we essentially, that's what we do today, honestly. We work with the biggest brands in the world to help them understand how they show up on an eval-based approach. But also we have a very sophisticated suite of CDN integrations. So we can actually plug in as well to, you know, if it's Akamai or Cloudflare or AWS or wherever the site is hosted, and then we're able to even see when ChatGPT is visiting that page to cite the content.
42:38So we can actually give you that. That's first-party data, but most marketers aren't using that data because it's, you know, it sits with IT or, you know, web services, but we expose those user agent visits to marketers. And essentially that's the new click. When a user agent visits, you know, the CMO podcast.com, that's the replacement for a human being because it's crawling on my behalf. So yeah, I mean, essentially long, long way to say I genuinely believe we can give you a good, at least a good direction of understanding there today. And I 100 % agree with that. And I think what we're doing is, it sounds a little cringe, but it is world class in terms of the industry standard.
43:22But I'll talk about some of the limitations there. But things like, hey, understanding user agent string, like who even visited you. And then working through, again, the attributions and what the data actually means. So a simple example might be like, hey, out of all of the results, like where did you rank in results? As in when they say, hey, top three destinations, were we, you know, on the second one or the third one? All of these things. And you can start fine tuning to your point, Jim, like where do you show up and what does that mean? But I think what we have is, you know, extremely helpful for setting a direction of how we're doing and where we're going.
43:57Of course, I think there are some industry problems to be solved. I think James and I talk about this from time to time. and Profile Art is a great solution for it, building towards this, but user memory is going to be a problem. So as we think about how the construct works, which is we are prompting search engines as if users were doing them, looking at the output and then using that as a proxy. But as more and more users use AI search engines, their memory and personalization will come into effect and impact what the end outcome will look like. So if you think about the RAG process, retrieval augmentation and generative, you know, more and more the personalization, the context window and memory is going to impact it.
44:38So how, as this scales over time, what is the accuracy of this proxy? And I think that's an industry problem to be solved. And James, I think you're already working on a few solutions, right? Yeah, we have persona-based prompting, so we can build personas. So we could build a persona of people between the ages of 30 to 35 who are based in Dallas with an interest in horseback riding and Mexican food. We can then send prompts through that persona. And I think, you know, I definitely, I'm always the first to kind of like nod my hat to Daniel's point. It's not surefire. It's not perfect. But it starts to, you definitely see once you append that persona to a thousand prompts and you send the prompt through that persona, you see a difference in the results.
45:19So it's definitely true that you can start to see that difference.
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46:29We're living through the biggest change in the internet since we've known it, right? And you talked about that, James, about a half hour ago. And Daniel, you've been talking about this. What's your counsel, both of you? Because you're deeply into this. You're doing super fascinating work. We have a lot of CMOs in our audience who are scratching their head right now saying, uh, am I doing enough? What should I be doing? Am I preparing myself? What are we doing that's needed to win in this new world? So what's your counsel to someone who's watching or listening, who feels an urgency to get going?
47:00What should they do tomorrow? I'll zoom in a couple of things. I'll make two points. The first is we talked a lot about AEO today, and it's certainly really, really important. and for most companies it's going to be the vast majority of your AI traffic. But I think thinking of AEO in silo with the rest of Agentic Search is a mistake. So AI ads is coming. Agentic Commerce is already here. The Google launch, their UCP, the Universal Commerce Protocol. OpenAI has their ACP. These are all words, but like the idea of finding product market fit in each of these services and platforms is going to be extraordinarily important for every consumer brand that's out there.
47:31I think if you can't get AEO, like good luck getting everything else. But it's, you have to think of it as a portfolio. And the search engines will also think of them as a portfolio of where to send the users on a query basis as they compete with other search engines to retain user attention. So I think that's point number one. Point number two is a little bit more theoretical and zooming out a little bit more. Every major tech company, I think, is playing AI bingo. And what I mean by that is they're not solving for a single future. They're solving for many futures. And I talked about these probable future states.
48:03For example, Meta acquired Manus late last year. Right now, it manages a general purpose agent that allows web rails to compete tasks on behalf of people. OpenAI launched Atlas to compete with Comet. All of these things are not isolated products, but I think a coverage play. So I'll give you a very quick mental model to think about it. Imagine on one axis, you've got the human interaction point where humans interact with agents. And then another axis, you've got agent rails, how agents communicate with one another. So right now, on the human side, there's a lot of assumption that the primary interface is apps like ChatGPT and Cloud and Perplexity.
48:40But it's possible that it happens at the browser level. It's possible it happens at the OS level, like your phone and your computer and your hardware level. And then on how agents communicate, there's MCPs, which seems to be the primary driver today. But there's UCPs and ACPs, and also a host of payment regulation problems that need to be solved for agentic commerce to scale. So if you think of this and you see what tech companies are doing, they are precisely playing some version of bingo. And I think at any tech company or any CMO, you should, yes, weigh in on what's happening today. But what will happen and will be the dominant form of where consumers interact with AI in the future and make sure that you're positioned at an advantage for whatever future that is.
49:22So that's my two cents. James? Yeah, my counsel to any CMO right now would be to go and find whoever was running your SEO, give them a pay rise and give them a pay rise and realize that what was formerly considered the kind of black sheep of the marketing stack could well now become the most important priority across the entire business. There's an ongoing debate around, you know, SEO versus AEO, GEO. All I'm saying is those folks that have been used to building content for algorithms are very well positioned to thinking about this new problem space of building content that's designed to be consumed by bots.
50:04And I think they are best positioned with this kind of they have all the tool sets of kind of a technical know-how, technical ability combined with it does still involve some creativity. So I think that SEO function could become mega sexy, is basically my view. And if you have a good SEO team in place, both internal and agency, I would lean in. Maybe to match Daniel's double point, the second thing, it's not a kind of one and done, big red button. This is a function of marketing. How you show up on these new surfaces, you don't solve it. It's an ongoing endeavor. and you need to give, if you empower that team, you need to give them the space and the encouragement and the, you know, the necessary resources to be able to build that strategy.
50:54We work with incredible marketing teams, but it's folks like Daniel or like the team at Ramp who are just super empowered and they are able to chip and iterate and learn with lots of agencies. So yeah, that'd be my two cents. Before we jump into the creative brief, let's talk about advertising for a minute. What do you think is going to be the biggest change in how we create place ads in this world of creating content for machines on behalf of people? I mean, that seems to me to be a very significant change. What's your counsel on that? My personal take is that generative ads will be the biggest unlock in marketing history.
51:30You know, if you think about the progression of advertising, beginning with newspapers, going to radio, television, social, it's essentially been a, I mean, search on the curve of intent, being able to measure intent, being able to understand what the user wants. You essentially, back in the days of newspapers, you were confined to just, okay, well, they bought the Financial Times, they probably work in finance. That was the best stab in the dark. Google search gave us a bit more. Social gave us interesting new signals because you could see what videos and comments, etc. Generative chat, multi-turn conversational interface.
52:06You understand such rich context and intent. Advertising is going to be so wonderful. And LLMs are perfectly suited to be able to synthesize a perfectly tweaked, tailored advertising moment exactly to that part of the conversation when Jim was asking about the Bahamas and just mentioned that, oh yeah, your partner loves paddleboarding. What if you booked this spot around the corner while you were there? Personalization in a way that we could not imagine three years ago. I'll share my speculation on sort of the AI ad space a little bit. I'm a little bit torn because there's a lot of problems to be solved precisely because of, I think, what James mentioned.
52:48I think it's the curse of context. The amount of noise in conversations to find out what the true intent is, is going to be extraordinarily challenging. And then the bar for recommendations would be really high because you expect to be so personalized. So that's going to be a really hard problem for these companies to think about solving. How do you take a slob of text over the last three to five minutes of just text with disjointed ideas and get to the intent such that the correct ad is sort of placed? And I think there's going to be a balance in terms of how these search engines also think about placing ads compared to organic, compared to actually having an agent complete a task through Agenda Commerce.
53:28Right. And it's going to be an interesting one because they're all fighting for the users. And right now, it's going to be an interesting one for these new players to actually take dominance. I'll take one other example of this. We know that AI search engines stole queries from Google. A lot of the queries are informational in nature, not commercial in an intent. And it's because they can't service commercial. So it will take time for these AI search engines to catch up. But once they do, it'll be an interesting battle to see how the ads play out. What a lot of startups are doing right now is there are now third-party AI ad services that are being launched.
54:07And there are publishers in AI search and chat beyond the majors like Claude and ChatGPT that are actually sizable in their user base. It'll be interesting to see how this ecosystem develops instead of having a couple of big players competing. Maybe there'll be this fat long tail that are competing alongside them. So it's an interesting one from a marketer's perspective. I think it'll be great to have a diversified sort of set of paid ads platforms, certainly. And then if there's obviously this long tail, even better for being specific on consumers. So very optimistic you both are about the future of advertising.
54:43Yes. They're probably biased. Okay. Okay. Listen, let's flip into a very quick creative brief. You guys are both two amazing young men. And what I think is interesting is, Daniel, you are super educated, right? degrees, McGill, Oxford, others, you're an international pilot. James, you have no formal education. So I'd like you to both speak to that. Why was that the right choice for you? I mean, who's doing better? I think James is crushing it. I remember at SPC, when someone said, this is SPC, that incubator, accelerator, that I spoke through. They start you off in a cohort. So you're in a big group.
55:19And I remember I walked in one day One of them was, oh yeah, you're the uneducated one. I was like, damn, that's a brutal way to put it. But this was a good choice for you, James. Why? I started my first business when I was 18 and just never looked back. So there was always, I mean, not now, but I think when I was 18, the idea was that I would start a business and then I was going to go back and do university. And then that didn't happen. Then I started a second business after that. And it just, it would be disingenuous of me to sort of make it sound like a Machiavellian strategy that was in place.
55:51I think I love learning quite often. I especially, you know, for all the stick that it gets, I think the U.S. education system is actually pretty cool. I think Stanford is, I think it's a very exciting place. Same probably for Harvard or, you know, Oxford, I think, in the U.K., where Daniel was. And, yeah, sometimes I fantasize about, you know, what it would have been like to have had a formal education, but I didn't. And here I am at war with my helmet on and my bayonet, and that's that. Daniel, how about yourself? Quite an interesting academic and successful academic record. Why was this right for you?
56:26I think to, similar to James, I don't think there's this grand plan, but I think it had to do with my survival strategy. So I grew up in a low-income immigrant family in the middle of nowhere in Canada. So opportunities were hard to get by. And if I didn't make it, the downside was pretty catastrophic. So what are some ways to hedge my risk and elevate my base case every time I go somewhere? So when I trained to be a pilot, I couldn't go ahead for a number of reasons, and then I pivoted to college. So college set a baseline of, I could probably get a minimum wage job, hopefully. And then Oxford did the same thing.
56:59And my career throughout, whether it's SoftBank or starting my own company, did that same thing. I think what I'm coming to realize is I've elevated my base to a level that I'm comfortable. And in the same way that maybe James fantasized about the counterfactuals of what it would have been like, I think starting early and doing what pulls you gives you a higher chance of finding and arriving your life's work, right? Like, what do you want to dedicate? James, you said you're going to work on this for the rest of your life. Like that's life's work. And I think that's incredible that you found it.
57:31And it's something that I will be looking forward to and continuing to iterate and seeing I've built this space for myself. What can I go do with it and bet my life on it? You know, this question is coming if you listen to our show. What's the first brand you remember making an impact on you as a young boy? James, start with you. I was big into soccer or football. We would call it correctly. I agree with that. There were, I mean, there's some controversy right now. I think with his son, Brooklyn, going around on my, my fiance, showing me it last night on social media, but these David Beckham Adidas football boots were just like, had to have them.
58:09Yeah. I mean, the only commentary I'd add is that I can just remember it being so visceral. Like I, it wasn't, it was a needed to own that pair of football. Nothing else mattered in my world at the time. And I think it's interesting when I think we, I shouldn't say who we work with and who we don't, but we may or may not work with the aforementioned brand in some way at this point in time. And, uh, it definitely leaves a lasting impact. Yeah, sure does. I'm older than you guys by a lot, but I remember when Adidas first came into the U S basketball shoes and it was that and they were triple the price of what I was wearing but I had to have them and I really did feel like I could jump higher move faster perform better with them on I'm sure you did I'm sure you know that's 90 % of it right yeah so Daniel how about yourself I think the biggest brand is probably Apple I think growing up like in the middle of the farm middle of nowhere like getting exited stuff hard but then when I when I first came across like an iPhone and I said wow that's that's pretty incredible I wonder what it can do and it took some time before I got my first set of Apple stuff.
59:10Now everything's Apple in my desktop here, but I like that there are technologies and software specific to Apple that enables you. Like I do pop music, right songwriting is my hobby. And there's specific software that is just better on the Mac and sound and plugins that are just better. So it's had a thing for me since I was a kid. And I'm finally able to use some Apple products. I'm very happy. Jim, can I ask you a question? What AI model are you using most right now? I'm using ChatGPT Pro. I'm using Gemini. I want to start using Claude. I think Anthropics is an amazing organization. So I want to lean in, but I haven't done it yet.
59:51But I mean, for my needs, you know, which are more research oriented. I mean, I was being honored at a big thing in New York in April. And I just said, you know, what should I wear? I had the most amazing response. I mean, options, they talked about my personality, the place I'm going, what it's like. And I asked it the other day, what I could learn from a choir to be a better show. Amazing response. You know, so a thought partner and a challenger. And I would say a standard elevator in addition to the normal stuff, you know. But yeah, it's a different, like, I can't search and get that. So no, it's a game change.
1:00:29But I think I have a personal goal to expand and try some other models and just keep exploring. What do you recommend for what I do? Why do you use ChatGPT and Gemini? Gemini, I'm a Google shop, right? We do everything on Google. So it's just obviously easy. And ChatGPT, I guess, was the first that came across and I just signed up right away. Yeah, it's been life changing. I mean, I was ChatGPT peeled to the max. Like I was an early adopter. And I think being an entrepreneur, you kind of root for the underdog like David and Goliath. Yep. I hate to say it, but more and more frequently as of late, I've been using Gemini because the responses are really good.
1:01:09So that's kind of... No, they are good. And it's easy. It's a build into everything I do, right? Yeah. It's a lot for grabs still. Yeah. No, for sure. For sure. So, okay, guys, I think we have to end with this question. What should... I think you've kind of answered it, but I want you to put a punctuation mark on it. What should CMOs, senior marketing leaders do after they stop watching and listening to the show? I was at www.tryprofound.com. I think you'll get a few of those. I think they should pay attention to the category. I think you should understand that this is a very big platform shift.
1:01:47This isn't search with a new UI. You are building marketing for machines. This is the biggest platform shift in the history of marketing. And you should think about it and, you know, consider it and invest accordingly, is my opinion. Yep. Daniel, anything to add to that? Just from a practical point of view, as a CMO, this is one portfolio of many. You're probably juggling paid loyalty, like everything on the stack. Realistically, keep open a radar, but get someone on your team, Empower someone on your team to go deep on this stuff and coordinate for you and bring the results back. Like you will not be coordinating with all of the page channels and the marketing channels and the corp dev and everybody internally within your company to go and execute, whether you build a product internally or work with a vendor.
1:02:33Like you will not have the bandwidth. Go empower your team to go do that and just let them run. Amen. Love it. Guys, thank you. Did you enjoy this? I loved it. Yeah, it was great. Let me add one thing to Daniel said. I was watching the college football finals this week, you know, Indiana against Miami. Apple, I think, released for the first time an ad about students and why they're right for students of all kinds. It is a gorgeous, beautiful, thought-provoking ad. So if you haven't seen it, it's a long one. It was like 60 or 90 seconds. Lovely. Absolutely lovely. Yeah, we'll take a look. James, thanks for thinking of being with the podcast.
1:03:10Jim, thanks for hosting me. This was great. Yeah, really appreciate you having us on, Jim. It's truly, I'm not saying this to be polite, truly an honor and a privilege to be on with you. Thank you. That was my conversation with James and Daniel. Listen, I normally do three takeaways for a business brand and life on this one, but this discussion was so interesting. I think there is really just one takeaway for you, our viewers and listeners, And that is learn about this profound shift in the internet and the implications on marketing. I think James said it well, go to the people who run search for you and get to know how you're going to show up in this new world of AI and creating content for machines on behalf of people.
1:03:52So go learn about it. Talk about it with your team. Elevate this on your priorities. This is really, really powerful. the implications for your brand and this industry are really deep. That's it for this week's episode of the CMO Podcast. As always, I would be grateful if you shared our show with your friends, along with subscribing and leaving a review on Apple Podcasts, Spotify, or wherever you listen. The CMO Podcast is a Vive original production. The views and opinions expressed by podcast speakers and guests are solely their own and do not reflect the opinions of our sponsors or its personnel, nor do our sponsors advocate or endorse any individuals or entities featured on the episodes.
From the publisher
We’re living through one of the biggest shifts in the internet since it began: a move from building content for people to building content for machines, on behalf of people. On this week’s episode, Jim Stengel is joined by James Cadwallader, Co-Founder and CEO of Profound, and Daniel Shin Un Kang, Head of Organic and Agentic Search at Expedia, for a thoughtful, practical conversation about AI search, answer engines, and what this shift means for the future of marketing.
James founded Profound in 2024, raising $60 million and earning recognition from Redpoint Ventures as one of the most promising private AI companies shaping applied artificial intelligence. Today, Profound works with brands like US Bank, Chime, Expedia, and DocuSign to help them navigate the transition from traditional search to a world of answer engines, agents, and AI-led experiences.
After building companies and investing in high-growth technology businesses, Daniel moved from the venture world into operating at global scale. He now leads Organic and Agentic Search at Expedia, where he’s helping redefine how one of the world’s largest travel platforms shows up in AI-powered search and discovery.
Together, James and Daniel unpack how brands actually appear inside AI systems like ChatGPT and Gemini, why traditional SEO metrics no longer tell the whole story, and how CMOs should rethink visibility, content, and measurement in an AI-driven world.
This episode offers a rare look at AI search from both sides of the table: the platform builder shaping the category and the operator putting it to work inside a performance-driven global brand. If you’re a CMO wondering what to focus on now, this conversation is a strong place to start.
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This week's episode is brought to you by Deloitte and the IAB.
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