Tech Deep Dive: IPOs, Enterprise AI Agents, Creator Economy, & The AI Search War | Aug 13, 2025

0:13Welcome, everyone, to the Informations TI TV. My name is Akash Pasricha. It is Wednesday, August 13th, and it is one of those shows today where we are taking a full tour of the tech sector. We have got First Smart Capital coming on the show to talk IPOs. We're going to go deep into the world of enterprise AI with May Habib from Writer. We're also going to talk about the current state of play in the creator economy with our friends at Kajabi. And last but not least, we are talking about the fast-moving world of AI search and a big funding round that Sequoia Capital just led. Now, before we get started, I want to highlight a new story that the information just put out this morning.

0:51The information has long been known for our detailed org charts that outline who reports to who at some of the biggest and flashiest tech companies. We have Meta, OpenAI, Snowflake, SpaceX. There's over 60 org charts now. Now, today we put out an org chart of software giant SAP mapping out the top 33 executives. I asked Aaron Holmes, the reporter who published that story, what the most interesting part of his reporting was. And he said, SAP wants to show shareholders it's serious about AI and its org chart is starting to reflect that. The company promoted a bunch of executives to oversee its push into AI sales.

1:29But meanwhile, its overall headcount has slightly shrunk as the company says it's automating more back office functions like IT and HR. We will link that org chart in the show notes that just came out this morning. Be sure to check it out. Okay, we've had a couple of big IPOs this summer. There was Figma, there was Chime, there was Circle. All of these companies have very different business models, but they also share a significant consumer angle to their business. And now StubHub has re-upped its plans to go public. I want to bring on First Smart Capital's Rick Heitzman to talk about that company and also where he sees the IPO markets headed.

2:06Rick, welcome to TITV. It's great to have you. Thanks for having me. This is great. My first time on. So hopefully it'll be an exciting time. And it's an exciting time to talk about the IPO market and some of the best companies that are out there. Well, first appearance of many. We intend to have you on more and more. Well, can you tell me in five minutes? That's as much notice as we give you. Yes. So look, you were an early StepHub investor. This is decades ago, but do you still keep in touch with the company? Keep in touch with the company a little bit, but I was an investor going back 15, 20 years ago in the original incarnation with Jeff Fleur, kind of leading the company, one of the earliest marketplaces.

2:46And then we built the company and Jeff did a fantastic job. And then we sold it to eBay in kind of its first incarnation. and then but obviously like everything else you continue to follow the company you continue to be interested about what they're doing right obviously cheer for their success so uh you stub hub you know it was going to go public they kind of pulled back a bit now they're they're saying they're going in the fall what do you think is this is this the time are they going they should go i i think the ipo market is open you've clearly seen that you are obviously hit on Circle and CoreWeave and Chime.

3:21And now Figma last week, and I think you're going to see Bullish is going to price any time now. So you're going to see fundamental demand for IPOs from the public markets. And it's a great time, whether you're in healthcare tech, crypto, or consumer, to test those public markets. The thing I want to ask you about StubHub is, you know, they waited. And look, times are uncertain here. There's no right time to go public, but they waited. And And now their latest financials show that revenue growth has slowed, free cash flow margins are half of what they used to be. Do you think they made a mistake and they should have gone earlier?

3:55It's hard to pick your window. I mean, the IPO market was generally closed and was one of the worst times for IPOs between the period of 22 to 24. So they might not have had that opportunity. You know, when we advise companies, I serve on the board of several companies. is obviously FirstMark has been a proud investor in a number of IPOs, that you can pick your window. The market kind of chooses your window. And your job as a founder and a CEO is to be ready when that market opens. And I think Eric Baker, who's the current CEO of StubHub, I think was preparing for a while and now sees the market opening and I think is ready to take advantage of that market window.

4:34And so when you're advising companies on what to look for, what should they be waiting for to take their shot. Well, I think you prepare because if you think about a Figma or a circle, people were not fully, you know, people were questioning, was the IPO market open? What does that mean for pricing? And obviously they had great IPOs. So you have to be almost anticipating the market opening and preparing for that success before that success comes. And so now, now as the market is clearly open, again, as we've talked about sectors, you have to be ready to get into that market and participate in what's clearly a good IPO market and the best one we've seen in five years.

5:14I want to ask you about, you know, people talk about waiting for that avalanche of IPOs to come. You know, the avalanche that we saw a couple years ago, it hasn't quite returned. It's sort of a steady trickle. You know, my take is this avalanche may never actually happen. You know, this might be a new normal where we see fewer companies going public because of the fact that the private markets are offering so much liquidity now. Do you agree with that? That's somewhat true. I don't think there's going to be an avalanche. I think a few select companies will be able to take advantage of the private markets to provide liquidity for early investors and employees.

5:50Obviously, SpaceX and Stripe are the clear market leaders there, but Databricks, and there's probably five to 10 companies who could play like that. But I don't think that's a broad-based group of companies. And I think that in the long term, those companies will have a lower cost of capital, more reasonable liquidity options, and having daily liquidity instead of liquidity by appointment. So the public markets is the clear and obvious exit. You mentioned bullish. Bullish is going public this week. What do you make of that business? Yeah, I don't know the business incredibly well, But what we've seen, and especially with Bitcoin, where it is today, that there's tremendous appetite for crypto.

6:32And, you know, bullish has the media business. They also have a trading business. So they kind of could be viewed as kind of a different way to play crypto if you're not, you know, buying crypto by itself or, you know, you want to diversify a little bit away from Coinbase, which was the clear proxy stock for a long, long time. And so bullish is going to benefit from that. I think eToro benefited from that. Circle is benefiting from what investors say of saying, hey, I need a piece of my portfolio, not only in actually the crypto coins themselves or Bitcoin and Ethereum, but I also want to participate that through operating public companies.

7:10And I think this is the beginning of something. We have a company, Grayscale, which hopefully will go public this year, which does a crypto ETF. There's obviously Gemini is talking about going public. There's a number of other companies will be behind it as this crypto infrastructure thesis plays out in the public markets. I want to take a step back and talk about, you know, some of the bigger tech companies and the capital expenditures that they're pouring into these AI investments. You know, one of the things we've written about at The Information is just the staggering amount of money it requires and the amount of money that these big tech companies are pouring into these investments.

7:49You know, the flip side of that is if revenue growth doesn't accelerate at these companies the way that they are perhaps pitching that it should, you know, a lot of these corporations are kind of just draining their cash balances on these investments. What do you make of that? So, I think you're hitting on the right issue of, okay, there's been an amazing, amazing investment in this infrastructure, you know, similar to the massive investment in bandwidth in the late 90s. We're even going back to the railroads from over 100 years ago. and at what point are the public shareholders going to demand a return on that investment, both in terms of quantum and time?

8:25So far, especially the MAG-7 have gotten a little bit of a pass that the more they've invested, the more the stock's gone up. But I think over the next 12 months, what you're going to see is a real return on that investment. And it can be, as you alluded to, on the revenue side, but I also think you're going to see it on the cost side. And I think you're seeing more automation in our companies, both on the startup side as well as the large companies they sell into. They're beginning to see a real return on investment from AI, initially an agentic AI for things like customer service. But we're going to see that more broadly driving a huge return on investment and driving real earnings growth and enterprise value growth.

9:05So stick with me here. So a year from now, we're saying revenue growth, not only top line, but also profitability. What happens if a year from now, the big tech companies haven't shown that? What happens? Well, I think you're going to see them getting punished for accelerating capex in the public markets, right? So you're saying, hey, you bet on this thing called AI. It didn't work out. Why are you continuing to bet on a bad hand? And yeah, I think that it's never perfect, right? It's never going to be black and white. you know, Zuckerberg's not going to put out a chart saying I'm getting a 3x return on investment for every dollar I spend on AI.

9:44Same thing with all the hyperscalers. But, you know, you're going to have to say, hey, I believe I've done this. I'm hiring less people. People has been a proxy thus far for some of the companies who are saying, hey, I'm able to use Copilot. I'm able to use a coding assistant to get more out of less people, especially on the engineering side, on the agent side, on the customer service, you've already had companies like Klarna come out and say, hey, we're just using less people and less agents. So you're going to see some of those quick wins that are obvious. And then it's going to get more amorphous as that quantum grows.

10:19But the amount being spent, the public market investors are going to demand for some accounting of that over the next year or 18 months. Right. Well, great. Rick, it's great to have you here. Thank you for joining us on the show. And we will give you more than five minutes notice, we should say. No, no, no. You gave me plenty of notice. I gave you plenty of notice this time. You're going to tell me how I did in five or 10 minutes, and then we'll see when I come on next. We'll have you on again very soon. That's Rick Heitzman from FirstMark Capital. Okay. Our next guest has built a company that is looking to be a one-stop shop for businesses and all their AI needs, whether it's agents, building new software, searching through their hordes of data or also making sure their company is compliant and protected against cyber threats.

11:05May Habib is the CEO of Writer. The company was valued at$1.9 billion in a funding round last year. And I want to bring her on to talk more about where the company is headed. May, welcome to TITV. It's great to have you. Thanks, Akash. Good to be here. So look, I was on your website last night. I was trying to really crystallize how I explain what exactly Writer does. And I saw these five product categories in one of the top bars, Action Agent, AI Studio, Palmera, LLMs, Knowledge Graph, Trust and Security. And I only know what a few of those words actually mean. So very quickly, I want you to go through each of those five and tell us what each of those five products actually do.

11:47Yeah, maybe at the very top, we start with what Writer is. We are the only end-to-end agent builder platform for the enterprise. And the pillars of that end-to-end product are build, activate, and supervise. On the build side of things, what the enterprise really craves is the ability to control agentic against really specific outcomes. And so the surface areas of our build product allow the customer to really galvanize and scaffold the agents that they build across a range of autonomy and a range of structure. And so if you are a enterprise using writer to build an agentic RFP solution and you are connecting a CRM to a knowledge base, to a Slack or a Teams, to email, right, to construct these hundreds of pages of RFPs, you are doing that in a single platform that allows you to use the best of what agentic is really great at, right?

12:56Being able to build technology. So you can build these agents. Yes, exactly. And being able to make this accessible to business users who don't need engineering and coding skills and can really leverage this fundamental disruption of agentic. That is what Build is for. What about Knowledge Graph? So Knowledge Graph is the ability for us to really abstract all of the data processing that needs to happen for LLMs to have context. And so that team inside of Rider is called our retrieval team. And it's a team that works on the ability to really construct very powerful retrieval features right on top of the Palmyra LLMs to make things like, you know, finding a needle in a haystack that much easier to make it more possible for you to very easily as a business user build an RFP application that actually works.

13:59as an example. And so knowledge is, you know, everything from a SharePoint to a Google Drive to a Notion. It is multiple sources of structured and unstructured data together. And then what we're doing is actually using a separate LLM to construct a semantic layer on top of those sources of truth. And then the agents actually can call one or multiple sources of of knowledge. Got it. Customer, major investment bank, 88 ,000 knowledge graphs built on writer, one for each company that they track to follow, right? So it makes it much easier to build agents that then can call that data securely. So one of the questions I wanted to ask you here is, you know, one of the topics we've written about at The Information are what we call the corporate data wars.

14:47And, you know, it's this idea that you've got all these agents that are trying to find all the right information in all the company's data sets. You know, it's something that you are helping companies with. But then you've got these bigger tech companies where all the data is held that are sort of putting up walls and saying, you know, companies like Salesforce blocking access to Slack data, for example. Is this an issue that you guys have had to face at Brighter? So there's no question that for the enterprise, right, what they want to be able to do is leverage what these super agents can do, right?

15:22And the most powerful thing that we can bring to a customer is the ability to bring down silos between teams, between systems, you know, between and across data. I think there is absolutely a right to win for the systems of record around agentifying access to and around their products, including to their own data. I think, you know, rightfully so, folks don't want to, you know, create a subpar customer experience by having, you know, a ton of point solutions deliver like thin functionality on top of what is essentially, you know, the data that they house. And at the same time, right, customers on the enterprise side who are spending tens of millions, hundreds of millions of dollars on systems of record, you know, want to make sure that, you know, the agents that they build there and elsewhere have got access to all of the contexts that, you know, actually provide the value.

16:24value. And so, you know, the way that we come to this is by really trying to be that trusted orchestration layer that delivers very, very high impact end-to-end workflows where the to win is obvious. If I am combining call transcripts with CRM data, with deep web research, with proprietary information and databases, with business know-how and processes, right that is just so far beyond what any one system of record can do um it provides you know a ton of stickiness for us a ton of differentiation compared to what you get from you know consumer llms as well as the the systems of record right well what are the interesting comments on one of these stories about corporate data wars that we wrote you know there was somebody who commented It feels like we're moving into the gloves are off phase of AI.

17:21Do you agree with that? I want to take a step back here. We're not just talking about corporate data wars. We're talking about people poaching researchers, right? We're talking about trying to raise the most money. Does it feel like that phase of AI to you right now? I do think it's a tale of two cities right now when it comes to that. There's definitely all of those living on the very, very edge of where this market is and where the technology is going, that it feels like a knuckle fight every day while the playing field is shifting literally on a daily basis. And then you've got the vast majority of the enterprise that is still catching up to where AI was in 2023.

18:04And I think, you know, the ability of the models to do cutting edge frontier work is like really at odds with most of the enterprise's experience with like 40, 50 percent hallucination rates and inaccuracy rates that like, you know, prevent a POC from scaling and the real lack of production grade ROI. And so we're really seeing that. And we see a big role that we play is abstracting that rate of change to the enterprise, just continuously being able to deliver that innovation in a way that is very trustworthy. So enterprise AI that doesn't just talk and wow, but it actually works and functions and can scale.

18:50And that has been a big, you know, differentiator for us. But no question, you know, every day is a zero to one type of mindset at Rider, no matter how big we get, no matter how deep we get inside of the enterprise. this. Great. Well, look, May, I want to thank you for coming on the show. It was great to have you and you guys are releasing products very regularly. And so next time you release a new product or maybe a sixth category to that product suite that you have on your website, you can come back on the show and you can tell us all about it. That was May Habib, the CEO of Writer. Well, the creator economy is an interesting moment right now.

19:28In many ways, it's never been easier to build an audience, but with all the competition, it's also never been harder to build a loyal audience that you can actually monetize. Joining me now is someone whose company hopes to solve those issues. Ahad Khan is the CEO of Kajabi. It is his first time on the show. Ahad, welcome to TITV. It's great to have you. Hey, Ahad Khan. Thanks for having me. Really appreciate it. So look, when I think of Kajabi, I think of the courses that creators sell online, make people pay for them. Is that how you make most of your money right now? No, so we make money via subscription payments revenue as a platform.

20:06The way our customers make money is actually very variable depending on what kind of business they want to build. Historically, we're a courses business. We've actually managed to broaden our portfolio quite a bit. So we have courses, obviously, communities, newsletters, podcasts, coaching products. We essentially want to be the one-stop shop for people who want to be able to monetize knowledge, experience, and expertise. and as that market has evolved, we've kept up with our product portfolio to make sure they can package that knowledge, experience, and expertise in whatever way that makes more sense for their business and for their audience.

20:37So you guys, it's a straight up subscription offering. You don't take a percent of sales that the creator charges, I guess? That's exactly right. So the way we think about it is that we don't want to punish success. So the idea here is that if you pay us a subscription, if you're making a million dollars on Kajapi, which thousands of creators have, or you're just starting out, your ability to scale and the revenue you generate isn't inhibited by a platform fee. Like it's just a very different approach to the market. And we believe that's really important because as people get smarter and smarter about the right ways to build businesses, right ways to generate revenue, but most importantly, the right ways to generate profit.

21:16They think about how their revenue is being spread to themselves, the platforms, maybe other parts of their business. And when they come to a company like Kajabi, they know how much they're going to pay every month. And they have that kind of visibility and that forecasting ability to know that if my revenue goes up, my profit goes up at that same rate because my platform fee stays flat. And that's a really different approach we have to the creator. Does that impact your bottom line at all? I mean, I'm imagining a creator that, you know, is making millions of dollars on the platform, for example.

21:43Maybe they're demanding more from the platform. Maybe they need more support from Kajabi. They're still getting charged that same subscription fee. And, you know, you're not taking a percent of sales. Does that impact profitability for you guys? no we're profitable so we feel very good about our financial position and even when you think about that dynamic of like one creator makes millions again we have thousands of them we have a person who's made over a hundred million dollars on kajabi um we actually have a lot less concentration of your top one percent think about youtube other platforms where the 0.1 make all the revenue that dynamic doesn't really exist on kajabi we are really proud of powering kind of the middle class of the creator economy so the average person monetizing kajabi makes over a hundred thousand dollars a year the average customer here is like six figures in doing very well building a business around knowledge experience and expertise and has a place in kajabi where they can build all that product we talked about they can email their customers as well they can take payments they can understand what's happening on their business all within one platform and that's what we've been building for the last 15 years and it's culminated in over 10 billion dollars of free revenue being built on a platform today.

22:50Well, I want to talk about that stat because when you guys put out the$10 billion figure, this is of course$10 billion in payments that have gone to Kajabi creators. One of the things you guys said was that the average six-figure Kajabi creator has between 1 ,000 and 10 ,000 followers, email lists of 4 ,000 people, and just 309 customers paying for their digital products. Again, these are people that are making six figures. And we're talking 300 customers, 4 ,000 person email list is, you know, that doesn't strike me as a huge email list. So, and I should say that, you know, the, you guys put out a figure, I think it was$9 billion in payments to creators in February.

23:32And it was just later, I guess, what was it? A couple months later that I got to 10 billion. So like, what kind of creators are we talking about here? Are these like, you know, like woodworking enthusiasts that are - It can be. I mean, these are people, yeah, these are, it's anywhere from how to sleep train your kids, to how to forage mushrooms, to how to do a certain kind of like real estate investing. It's what we really think about it. It's like the best thing about the creator economy or digital entrepreneurship is that the world becomes your market, right? And when you have interesting ideas or knowledge or experience or expertise or frankly, a brand where people are like, oh, I want to listen to Akash talk about how to build a media business, right?

24:13That means all of a sudden that you have an audience who's interested in what you're putting out there. Ways to validate that, we talk about it as like social media platforms are fantastic places to validate that the things you're saying have a potential audience, right? If you're able to build followership. But we really believe that like social media are great places to build audiences, but bad places to build businesses. And that's where Kajabi comes in. So to your point, even modest email lists or customer accounts can translate into six figure businesses. is just give it the dynamics of I can directly build a product, sell it directly to you, price it however I'd like.

24:46And all of a sudden, I don't need millions and millions of followers to make six figures. I need a couple hundred customers paying me whatever I want to be able to charge for the value that I'm putting out there, and I'm able to build a sustainable living. And we have tens of thousands of those customers on our platform. And to your point, GMV continues to grow at a really rapid clip. GMV is creator revenue, right? And so our whole belief is that as a creator, economy gets more sophisticated, creators continue to look at themselves as more brands and business and entrepreneurs than just putting content out there, that education, that sophistication is going to lead them to think about platforms like Kajabi because you can actually build your brand and business on Kajabi in one place.

25:25I want to talk about sort of the future of the creator economy and also the future of content. We talked about some of the very niche ways that creators are making money on your website. I talked about woodworking, You know, you mentioned a couple other, I see there's public speaking, video, video effects, animation, stuff like that. So look, the creator economy has really, you know, niche has served a lot of creators really well. And I have trouble thinking about how much more niche we can get and, you know, like what the next phase of the creator economy is. What's your view on that? Yeah, I mean, I honestly, the funny thing is I think about the media business quite a bit when I think about this.

26:05And what I mean by that is, you know, I'm 44 years old. So when I grew up, there weren't that many places to go get information, right? What happened to social media is a great fragmentation. Now, all of a sudden, you can go to X, you can go to wherever, you can go to the information and find very bespoke, high-end content that's specific to what you love. And I actually think that's the future of what the creator economy enables to, which is why a niche sounds small, because that's what I think people are used to, like the synonym of niche is kind of small. But a niche doesn't mean there's not a lot of revenue to be built.

26:34It just means you got to be able to find an audience that is interested in what you're putting out there and build product that serves those customers very well. And you're able to build a business. So I actually am more bullish on fragmentation in the creator economy and the digital entrepreneurship space now than I was five, 10 years ago. Because I just think that trend is going even more like we're going from woodworking to like shelves gets one creator. Chairs gets another. Oh, for sure. I'll give a great example. like we have a company called honey flow their base thing is a family based in australia they teach a specific type of beekeeping right and so they use kajabi for their website for their email list for their digital uh courses and community but they also have a physical goods business so they sell the actual um products that they teach you how to like become a beekeeper on in one specific niche of beekeeping that's an example of like the deeper you go uh i think there's just so such a big market out there that people underestimate their ability to define their niche a lot easier than it was before.

27:35Last question for you before I let you go. I want to get your take on AI generated content. Do you think this helps or hurts creators? I think it's kind of both. So my view on it personally is that AI content and particularly digital content, it's going to be the great commoditization, right? Everything becomes really easy to build. You press a button, your website's up, your avatar's up, whatever it is that you want to be able to represent yourself using ai it's a ton i think what that's going to create is a dynamic around people wanting genuine experiences with people in brand and individuality is going to matter more in that world so again i can go to any internet site and find information but if somebody who's done something again that idea of knowledge experience and expertise somebody who's demonstrated their ability to be a fantastic media producer i'm going to go to that person and digest their content because i know that they've accomplished something and i actually think that's the way the world is going Now that creator is going to be leveraging all the AI tools at their disposal to make sure that they're as scalable as possible.