OpenAI & Anthropic Execs Leading the Pentagon AI Showdown, Amazon Explores AI Chabot Ads

3 Mar 2026 · 45 min · 26 chapters

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The Information's TITV Episode Summary

Episode Title OpenAI & Anthropic Execs Leading the Pentagon AI Showdown, Amazon Explores AI Chatbot Ads

Episode Description In this episode, AI Reporter Stephanie Palazzolo discusses OpenAI's recent deal with the Pentagon, Anthropic's position, and the competition for AI talent in Washington. The episode also features insights on Amazon's plans for AI chatbot advertisements and a look into Basis CEO Matt Harpe’s successful funding round. Additionally, Tom Schmidt from Dragonfly Capital shares details about their new crypto fund amidst the ongoing cryptocurrency downturn, followed by an analysis of MongoDB's stock drop and AI guidance by Macquarie’s Steve Koenig.

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Key Discussions

OpenAI and Pentagon Agreement

  • OpenAI's Deal: OpenAI updated its agreement with the Pentagon to prevent the use of its AI models for domestic surveillance.
  • Concerns: Backlash over OpenAI's perceived willingness to accept terms that Anthropic rejected has led to employee discontent and user backlash, with a reported spike in uninstalls of the ChatGPT app.
  • Key Figures:
  • Emile Michael: Undersecretary of War for Research and Engineering, instrumental in negotiations with tech companies.
  • Tarun Chhabra: Anthropic's head of national security policy, with previous experience influencing AI diffusion rules in the Biden administration.
  • Joe Larson and Katrina Mulligan: OpenAI’s key personnel involved in governmental negotiations, with backgrounds in defense contracting and public policy.

Amazon's AI Chatbot Advertising Initiative

  • Ad Strategy: Amazon is exploring the sale of software that enables chatbot companies to integrate advertisements, expanding their advertising reach.
  • Market Dynamics: As AI chatbots gain traction, Amazon aims to position itself as a primary ad tech provider, alongside competitors like Google, leveraging their existing advertising capabilities.

MongoDB Stock Performance

  • Quarterly Results: MongoDB's share price dropped over 25% following disappointing quarterly results and the departure of the Chief Revenue Officer (CRO).
  • Market Response: Concerns about the future trajectory of revenue and alignment issues between leadership contributed to investor anxiety.

Basis's Funding Success

  • Funding Round: Basis, an AI accounting firm, raised $100 million at a $1.15 billion valuation, highlighting investor interest in AI applications within accounting.
  • Operational Overview: Basis utilizes AI agents to automate accounting tasks, significantly enhancing efficiency for its clients.

Dragonfly Capital and Crypto Investments

  • New Fund: Dragonfly Capital raised $650 million for investment in crypto ventures, despite a challenging market.
  • Investment Focus: The fund will target companies that leverage stablecoins and innovative payment solutions.
  • Market Sentiment: Despite downturns, the firm manages to attract interest from institutional investors who see potential in long-term crypto development.

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Key Takeaways

  • The episode illustrates the evolving relationship between tech companies like OpenAI and government entities, with significant implications for privacy and surveillance.
  • Amazon's venture into chatbot advertising marks a strategic move to tap into emerging markets, positioning itself as a major player in the ad tech space.
  • MongoDB's performance highlights the volatility of tech stocks amid broader market fears, emphasizing the need for strategic leadership alignment.
  • Basis's funding success emphasizes the growing interest in AI-driven solutions within traditional industries like accounting.
  • Dragonfly Capital’s ability to raise funds in a crypto winter reflects investor confidence in the long-term potential of blockchain and decentralized finance solutions.

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Articles Discussed

  1. [Amazon Explores Helping Apps Sell Chatbot Ads](https://www.theinformation.com/articles/amazon-explores-helping-apps-sell-chatbot-ads)
  2. [OpenAI & Anthropic Execs Center Pentagon Action](https://www.theinformation.com/newsletters/ai-agenda/openai-anthropic-execs-center-pentagon-action)
  3. [Anthropic Stands to Gain from Pentagon Stance](https://www.theinformation.com/newsletters/the-briefing/anthropic-stands-gain-pentagon-stance)

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*This summary captures the key discussions and takeaways from the podcast episode, providing a structured overview of the topics covered.*

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

AI Showdown Overview

0:46 to 1:19

Discussion on the ongoing dynamics between OpenAI, Anthropic, and the Pentagon.

“and we will end the show with a conversation with Dragonfly Capital about how they raised a crypto VC fund in the depths of the crypto winter.”

OpenAI's Updated Agreement

1:20 to 2:28

Details on OpenAI's newly amended agreement with the Pentagon regarding surveillance concerns.

“Okay, so what are the latest updates in the drama here?”

Public Reactions and Impact

2:29 to 3:17

Exploration of user reactions to OpenAI's agreement and its impact on app usage.

“sharing their thoughts about what's going on and some of their concerns about, you know, this agreement that OpenAI had signed with the government.”

Key Figures in Negotiations

3:18 to 4:06

Introduction to the important players in the negotiations between OpenAI, Anthropic, and the Pentagon.

“I think this is definitely a step in the right direction.”

Emile Michael's Role

4:07 to 6:10

In-depth look at Emile Michael's influence in the negotiations and his background.

“Now, you wrote a really interesting newsletter today in AI Agenda, your daily column that comes out, and you wrote about the key characters that are at the center of these negotiations.”

Tarun Chhabra's Background

6:11 to 7:30

Overview of Tarun Chhabra's previous experience and role at Anthropic.

“But he's actually been involved in policy and the government for quite a while.”

Joe Larson and Katrina Mulligan's Experience

7:31 to 9:13

Discussion on the backgrounds of Joe Larson and Katrina Mulligan at OpenAI.

“So Joe Larson is OpenAI's head of government.”

Hiring Strategies in AI

9:14 to 11:10

The competitive landscape for hiring talent with government experience in AI.

“We talk a lot about the talent war with researchers and with engineers and with technical talent.”

Negotiation Dynamics

11:11 to 11:50

Exploration of how political affiliations affect negotiations in the AI space.

“You know, some people are speculating, for instance, that it might have helped that, you know, Sam has been seen at a lot of these kind of like White House dinners with Trump.”

Amazon's New Advertising Strategy

11:51 to 12:19

Insights into Amazon's plans to integrate ads into chatbots, expanding its ad business.

“That is Stephanie Palazzolo, our AI reporter here at The Information.”
Show all 26 chapters

Rationale Behind Amazon's Moves

12:20 to 14:00

Analysis of Amazon's motivations for venturing into chatbot advertising.

“Okay, so just to remind people, we know we have Amazon, okay?”

Emerging Chatbot Advertising Market

14:00 to 15:47

Explore the new landscape of chatbot advertising and its implications for major companies.

“Companies like Yahoo and Time have also released chatbots.”

Challenges for Established Ad Tech Giants

15:47 to 17:55

Examine whether traditional ad tech giants can maintain dominance or if startups will thrive.

“I know last week, Koa came on the show to talk about a fundraising round, and they would be another company competing in this space, providing the sort of the technical layer for powering ads and chatbots.”

OpenAI's Advertising Partnerships

17:55 to 19:15

Discuss OpenAI's advertising strategies and partnerships amidst industry dynamics.

“I know that I interviewed the main investor in Coa for this article, and he was saying that, you know, it's going to need new targeting, new ad formats.”

MongoDB's Quarterly Performance Analysis

19:44 to 20:54

Delve into MongoDB's quarterly results and investor concerns following the CRO's departure.

“What did you make of the results last night?”

Impact of CRO Departure on MongoDB's Future

20:54 to 22:04

Investigate the potential implications of the Chief Revenue Officer's exit on MongoDB.

“The AI fears are out there and they're going to stay out there for a while.”

CEO's Candid Comments on Adoption Rates

22:04 to 24:49

Evaluate MongoDB CEO's frank remarks regarding enterprise adoption of AI technologies.

“I mean, I was looking at the results, and I mean, the company did seem to be accelerating a bit this year.”

Understanding MongoDB's Core Product Offering

24:49 to 26:33

Clarify the key functionalities and applications of MongoDB's database software.

“But keep in mind, like, there's not a whole lot of traction yet from what we can see with their AI products in the enterprise.”

MongoDB's Position in the AI Era

26:33 to 27:26

Discuss MongoDB's strategy and prospects in the evolving AI landscape.

“So that's really what they're all about.”

The Role of AI in Accounting

28:00 to 30:28

Learn how AI agents are transforming accounting practices and addressing inefficiencies.

“So we have long-running agents that are able to actually do real work for accounting teams that allows them to automate a substantial portion of the manual work that's involved in doing this accounting work.”

Fundraising Strategies and Experiences

30:28 to 33:00

Discover insights on attracting investors and navigating the fundraising process for startups.

“Now it leads me to my next question, which is that, how did you get all of these investors participating in year round?”

Managing Compute Costs in AI

33:00 to 34:45

Understand the challenges and strategies for managing compute costs in AI development.

“But, I mean, what's the advice that all these advisors are giving you about how to manage those compute costs, which, you know, they're kind of slow to come down?”

Lessons from OpenClaw and Internal Efficiency

34:45 to 36:20

Explore how companies can leverage internal systems to enhance operational efficiency.

“And very quickly, are you using OpenClaw at all?”

Navigating the Crypto Venture Landscape

36:55 to 42:00

Gain insights into the current crypto fundraising environment and investment opportunities.

“Okay, can you talk about how difficult it was to raise this fund?”

The Collision of AI and Crypto Talent

42:00 to 43:19

Explore the competitive landscape for talent between AI startups and the crypto sector.

“multiple different Apple Silicon devices on your network.”

Future of Commerce and Agentic Payments

43:20 to 44:22

Discuss the emerging trends in payments technology and the future of commerce.

“It's people implementing X402, which is this new standard for doing payments over the internet, Stripe's adopting it, Coinbase is adopting it.”
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Transcript

Automatic transcript. May contain errors.

0:13Stephanie Palazzolo:Welcome, everyone, to The Information's TI-TV. My name is Akash Pasricha. It is Tuesday, March 3rd. Today on the show, we have the latest updates on the OpenAI, Anthropic, and Pentagon showdown. We'll bring on our AI reporter shortly. We then have some exclusive reporting on how Amazon is looking to take advantage of the AI chatbot advertising game that is heating up. We're also getting into MongoDB's big stock drop this morning after its quarterly results last night. We'll then bring on an AI founder whose accounting startup has attracted a who's who of Silicon Valley investors. and we will end the show with a conversation with Dragonfly Capital about how they raised a crypto VC fund in the depths of the crypto winter.

0:57Stephanie Palazzolo:It's going to be a busy show, so let's get right on into it. The showdown between OpenAI, Anthropic, and the Department of Defense has had more developments this week, not the least of which was an amendment in the deal that OpenAI made with the Pentagon. I want to bring on Stephanie Palazzolo, our AI reporter, who wrote about these dynamics today in her AI Agenda newsletter. Stephanie, welcome back to the show. It's great to have you here.

1:21Akash Pasricha:Thanks. Great to be here.

1:23Stephanie Palazzolo:Okay, so what are the latest updates in the drama here?

1:29Akash Pasricha:Yeah, so yesterday was a big day for the ongoing drama between the Pentagon, OpenAI, and Anthropic. So the really big news is that late yesterday, OpenAI basically came out and said that it had updated its agreement with the Pentagon to put stronger protections against the Pentagon using OpenAI's AI models for domestic surveillance via commercially obtained data. And CEO Sam Allman also came out and said on X that the Pentagon had affirmed that they won't be using OpenAI's models for Department of War intelligence agencies, so things like the NSA. And so all of this really comes after a weekend of, you know, backlash and just general commentary around the fact that Open AI seemed willing to sign an agreement with the Pentagon that seemed to say that Open AI was accepting some of the terms that Anthropic had turned down in its earlier talks with the Pentagon.

2:27Akash Pasricha:So we saw a lot of, you know, current and former Open AI employees coming out on social media, sharing their thoughts about what's going on and some of their concerns about, you know, this agreement that OpenAI had signed with the government. And then, you know, we also saw strong reactions from consumers. So there were reports over the weekend that there was a big spike in people basically uninstalling the ChatGPT app from their phones, and also a very big spike in people switching over to the Claude chatbot and app from Anthropic, which I think as of yesterday was number one on the App Store.

3:02Stephanie Palazzolo:Do you think that these changes will be enough to satisfy the concerns that employees have been expressing and ultimately maybe even have people reinstall ChatGPT? I mean, does this feel like it's enough to you or do people expect that maybe OpenAI will have to make even more amendments?

3:23Akash Pasricha:I mean, we'll have to see. I think this is definitely a step in the right direction. But as my colleague Aaron Wu wrote about earlier this week, the language in the agreement between OpenAI and the Pentagon is a bit vague. And there is a lot of wiggle room in terms of the Pentagon being able to use OpenAI models for things that, you know, employees might not be super thrilled about. But, you know, as we know, like the news cycle moves quickly, people have short memories with these sorts of things. But as I've written about, OpenAI cares a lot about continuing the growth of Chat2BT, and they have had a bit of a slowdown since last fall.

4:02Akash Pasricha:So I think they're definitely paying attention to Chat2BT usage numbers and will be pretty quick to respond to any dips in usage or people leaving the app in favor of other ones like Claude.

4:14Stephanie Palazzolo:Now, you wrote a really interesting newsletter today in AI Agenda, your daily column that comes out, and you wrote about the key characters that are at the center of these negotiations. And look, we know the names that we've heard a lot about, Sam Altman, Dario, and Pete Hegseth on the government side. So let's put those names aside. Tell me a little bit about some of the other characters here that we should be paying attention to. The person I want to start with is Emile Michael. Tell us about him.

4:47Akash Pasricha:Yeah. So while there's been a lot of focus on, you know, tweets from the secretary of war, Emile is really the one that's kind of the boots on the ground. He's the one that's in the room really, you know, kind of working out the details of these different agreements. So he's the undersecretary of war for research and engineering and is, again, the person in the room that's really working out these deals with the Pentagon and OpenAI and Anthropik. What's really interesting about Emil is that he actually has pretty deep ties to the tech industry. So he used to be Uber's chief business officer. And I think one kind of infamous fun fact, I guess, about him is that he's also well known for basically making comments during a dinner that he thought was off the record that Uber should hire researchers to dig up dirt on journalists that were critical of the company.

5:39Akash Pasricha:So this is a guy with very strong feelings, not afraid to say them. And we've seen him really play hardball with Anthropic. in these talks over the last few days.

5:51Stephanie Palazzolo:And so let's go to both the Anthropic and the OpenAI sides now. Underneath Dario Amadei, Anthropic has somebody by the name of Tarun Chhabra. Who is he?

6:06Akash Pasricha:Yeah, so Tarun has been at Anthropic for a little bit now as its head of national security policy. But he's actually been involved in policy and the government for quite a while. So most recently, he worked in the Biden administration, where he basically was kind of the figure that drove a lot of the work behind Biden's AI diffusion rules, which, as a quick refresher, were these rules that, you know, the Biden administration came out with shortly before he left office that put a lot of restrictions on the sales of, you know, AI-related tech and chips around the world. So he was a really big figure that spearhead a lot of the work around, you know, expert controls with China, for instance.

6:49Akash Pasricha:But it's important to note that the Trump administration actually got rid of those AI diffusion rules whenever, you know, Trump took office because they said that those rules were burdensome and would kind of stifle American innovation. And so that can kind of give us a little hint into how the Trump administration might feel about Tarun and some of the things that he did while in the previous administration.

7:14Stephanie Palazzolo:Well, and it sounds like he has always been very much on the more careful side of AI safety and putting those guardrails in place. On the OpenAI side, we have Joe Larson and Katrina Mulligan. Who are the two of them? Yeah.

7:31Akash Pasricha:So Joe Larson is OpenAI's head of government. He previously worked at Anderil and really was a person that came up with his playbook on how it wanted to sell to the government. So OpenAI essentially brought him on last summer to kind of re-implement that same playbook at OpenAI as they figure out, you know, what their relationship is like with the government and how they want to sell to the government. This also really isn't his first rodeo when it comes to these, you know, these controversies that arise surrounding contracts that tech companies are signing with the government. So he was actually a founding member of Project Maven, which was a Pentagon initiative with Google that was a couple years back that basically wanted to use Google's AI to improve drone strike, to improve the targeting of drone strike technology.

8:21Akash Pasricha:So then in 2018, there was actually a huge backlash from Google employees about Google's contract with the Pentagon here. And eventually Google actually ended up canceling that contract in response to, you know, a lot of the protests and concerns of employees. So that's Joe with Katrina. She's actually been at OpenAI for more than two years, which kind of makes her like a relative vet at the company, just because it's kind of policy and government hires have tended to be more recent. And so she was actually previously the chief of staff to the Army Secretary in the Biden administration. And, you know, fun fact about her is that she actually led the Obama administration's media and public policy response to the Edward Snowden whistleblower disclosures, including about the NSA's surveillance of Americans.

9:13Akash Pasricha:So she's someone that has a lot of experience with these sorts of matters of national security, and she's also a vet with these sorts of issues as well.

9:23Stephanie Palazzolo:So it is kind of interesting to me. We talk a lot about the talent war with researchers and with engineers and with technical talent. And here, I mean, look, we don't know how much they're getting paid. We don't know how it compares to the researchers and if they are nine-figure-dollar compensation packages. But I imagine that these former government officials, people who have experience navigating all different layers of government, I imagine there is a very much a tug of war to get the best talent as these contracts become more important. So it is.

9:56Akash Pasricha:Yeah, it's also not even only the best talent, but it's also the people that will appeal the most to the current administration. So you can imagine that, you know, hiring a ton of, like, you know, government folks that are related that are connected to the Democrat Party or to the Biden administration might not bode super well with the current Trump administration, even if they're, you know, very well respected people. So it's a very yes, I think it's definitely comparable to the AI talent war in some ways.

10:23Stephanie Palazzolo:And that's actually what I found kind of interesting because it sounds like on both the open AI and the anthropic side, the top negotiators are actually people who were in the Biden and the Obama administration on both sides. I'm just looking, I'm like, I guess, is Joe Larson maybe the exception there? Or was he also in the Biden administration?

10:47Akash Pasricha:Yeah, so I think that's a really good point. I think we've written about how both OpenAI and Anthropic have hired a lot of folks from the Biden administration and have only kind of in recent months really started to ramp up hiring for more, you know, conservative or, you know, folks associated with the Trump administration. But there's also kind of more going on here, I think, beyond just these individual figures that are like in the war room, so to say. You know, some people are speculating, for instance, that it might have helped that, you know, Sam has been seen at a lot of these kind of like White House dinners with Trump.

11:28Akash Pasricha:Obviously, co-founder, President Greg Brockman and his wife donated$25 million to a Trump super PAC. I think, you know, we're careful not to kind of say that there is a direct connection here. But these are just things that people are thinking about whenever they're trying to understand. And why is it that the government seems more willing to work with a company like OpenAI than Anthropic?

11:49Stephanie Palazzolo:Great. Well, Stephanie, I want to thank you for coming on. That is Stephanie Palazzolo, our AI reporter here at The Information. Amazon is considering selling software to chatbot companies that would help them install ads into their own chatbots. That is according to a new exclusive story published by my colleague Catherine Perloff. It is the latest way in which the different stakeholders in the advertising economy are gearing up for the wave of ads that are inevitably on their way for AI chatbots of all kinds. I want to bring on Catherine to tell us more about what she has learned. Catherine, welcome back to the show.

12:23Stephanie Palazzolo:It's great to have you here.

12:25Steve Koenig:Hey, Akash.

12:26Stephanie Palazzolo:Okay, so just to remind people, we know we have Amazon, okay? Amazon sells ads on their platform, on the marketplace. We've probably seen them. Amazon also sells software and tools for advertisers to use to place their ads in other advertising websites like Pinterest, for example. And so what you have found today and what I want to unpack is that they are looking at some kind of a suite of tools, perhaps, that will help advertisers put ads in chatbot companies, which is kind of a new layer to all this. Help us unpack what it is that you found, why Amazon is even doing this.

13:03Steve Koenig:Yes, no, it can get a little confusing. So yeah, Amazon, part of Amazon's ad business is helping other websites with their ad businesses. So providing the technology for other websites to sell ads. And this helps Amazon offer more different places to its advertisers to put their ads. And yeah, they are exploring offering chatbots as a new surface for advertising. They already do have ads on Rufus, or I think I've been testing those. But this would be helping chatbots on other websites. For example, one company they've thought about for this experiment is Pinterest. Helping these other websites power ads on their chatbots.

13:53Steve Koenig:So helping creating the technology that would put ads in other companies' chatbots, you know, that could be, as we've said, Pinterest. Companies like Yahoo and Time have also released chatbots. There are a bunch of new consumer AI startups that might want to offset the high cost of developing AI with advertising. So that's sort of the market we're looking at, but it is pretty new.

14:17Stephanie Palazzolo:So, and let's get into the core reasons here for Amazon doing this. I mean, I always think about if whether or not these plays are offensive or defensive in terms of have we seen any investor concern about Amazon's ad revenue falling or maybe their ad tech products falling out of favor with the search businesses. I mean, why do you think they're doing this?

14:43Steve Koenig:I think it's pretty offensive. Amazon has in the past, especially a year or so, though maybe a little longer, kind of become more of a force in advertising technology. You see that against the backdrop of Google facing a lot of antitrust scrutiny for their advertising technology business. And Amazon, you know, I wrote about this a bit last year, but, you know, they only have so many places to show ads on their own website. And if they can offer their advertisers more places to advertise, especially in a growing segment of the market like chatbots, that's great. And, you know, the kind of chatbot advertising market is very new.

15:22Steve Koenig:So I think being an early player here bodes well for them and kind of adds a bit of a feather in their cap to this idea that they are a new ad tech powerhouse that will compete with Google and a host of other smaller firms. I will say that Google actually last year, Bloomberg reported, was also kind of experimenting with helping third-party apps with chatbot advertising. But it's all pretty new.

15:46Stephanie Palazzolo:And so Google, Amazon, are there any other big players that are doing this that we should be aware of?

15:52Steve Koenig:I don't think any on that scale. there are some startups. I know last week, Koa came on the show to talk about a fundraising round, and they would be another company competing in this space, providing the sort of the technical layer for powering ads and chatbots. But yeah, I mean, I do think this is all pretty advantageous for Amazon. Advertising is actually their fastest growing business last year on an annual revenue basis. So they're trying to sort of stay in the money.

16:19Stephanie Palazzolo:Now, you mentioned Koa, and one of the questions that I've been thinking about is to what extent the old ad tech giants will end up prevailing in this new advertising economy with chatbots, or if there actually is room for these startups and lesser known companies to really become the dominant player. I wonder advertisers that you talk to, I mean, they're probably all used to dealing with these giant tech companies. do they kind of feel like they're going to sort of go back to whoever they trust with these types of products?

16:54Steve Koenig:I think that's really a question of like technical innovation. So like if we find that chatbots require new ad formats and new targeting and other startups are faster at developing these techniques, I think advertisers will go there. You know, we kind of look at the history. Like first there was web advertising, then there was mobile. A whole new wave of ad tech companies, including Applova and maybe being the best well-known, kind of came up because they were able to offer new technology that, you know, was novel for how to advertise in this new format. Now, the next big kind of wave was streaming television.

17:32Steve Koenig:And a lot of the same, there were some maybe newer players, but a lot of the same kind of advertising technology companies that have been kind of known for web advertising were able to still become big players in streaming television. And so I think it just depends on whether chatbot advertising kind of requires innovation that a startup can provide. I know that I interviewed the main investor in Coa for this article, and he was saying that, you know, it's going to need new targeting, new ad formats. A startup will provide that. I mean, he would say that, of course. But, you know, I think that, yeah, we have to wait and see.

18:14Stephanie Palazzolo:Now, last question here. Do we have any sense of the work that's happening with OpenAI, given that Amazon has invested all this money into OpenAI? I mean, they are obviously introducing ads themselves. Are they going to end up using these products?

18:27Steve Koenig:It's a good question. You know, we don't know. And that release about the OpenAI Amazon deal did not mention advertising. But actually, like yesterday, OpenAI announced a partnership with an advertising technology company, Criteo. So that shows that OpenAI might be open to partnering with other advertising technology companies. And, you know, why not use Amazon? They might not want to because that would give Amazon more access into their data and their audience.

Read the full transcript

18:59Stephanie Palazzolo:They already have so much access as it is.

19:02Steve Koenig:Yeah, and they might want to say, hey, we have a unique audience that maybe not all of them are using Amazon. I don't know if that's true, but maybe that's true. and we want to keep that to ourselves or we don't want Amazon to know how our audience is shopping on ChatGPT. And that would be fair, but we'll see. Great.

19:18Stephanie Palazzolo:Well, Catherine, I want to thank you for coming on. That is Catherine Perloff, our Amazon reporter here at The Information. MongoDB reported its quarterly results last night. Shares were trading more than 25 % lower this morning. The company said its chief revenue officer was leaving the company to understand what is going on. I want to bring on Steve Koenig, U.S. Head of Software and Services Research at Macquarie. Steve, welcome to the show. It's great to have you here. Thank you, Akash. Thanks for having me. What did you make of the results last night?

19:50Tom Schmidt:Well, the results were okay. You had Atlas, their cloud database, decelerated by one point, but still growing at 29%. Apart from the departure of the CRO, the other big negative was in the minds of investors was the guide, the initial guide for fiscal 27. The revenue guide skewed down from consensus. You know, the low end, I think, fell something like 40 million below consensus. So that was taken as a negative. And then, you know, the departure of the CRO with no replacement, you know, that was also a concern, you know, for investors too. So that, you know, hence the big down move in the stock today, we see some big, pretty big outside moves in this space especially lately do you think that this is a mongo db story today the stock shop or a sas apocalypse story today well mongo db is trading trading down a lot more than everyone else you know uh but but yeah we're seeing you know i think i think software is um you know software's certainly multiples have gotten compressed uh significantly in the last couple of months, but today's price action looks to be more kind of geopolitically driven across the board than some kind of like major resurgence of AI fears.

21:17Tom Schmidt:The AI fears are out there and they're going to stay out there for a while.

21:20Stephanie Palazzolo:And more what I meant was, let's say maybe two months ago when the SaaSpocalypse was not so much in the conversation, let's say you have the CRO leaving, I mean, do you think the stock drops 27 % or do you think that that is very much amplified today by the SaaS apocalypse fears?

21:39Tom Schmidt:Yeah. Well, I think it's both. I think that's fair. But I think you've got a big part of the price action here is it's unsystematic risk. It's negative alpha associated with the events going on at Mongo, the guys and the CRO leaving. So I think it's both, but mostly it's company-specific stuff going on here.

22:04Stephanie Palazzolo:And do we have any rationale or reason as to why the CRO might be leaving? I mean, I was looking at the results, and I mean, the company did seem to be accelerating a bit this year. Then the guide is kind of what's dipping it lower. It's a bit of a boomerang. What do we know about why they might be leaving? Yeah.

22:21Tom Schmidt:Yeah. You know, we don't have the inside scoop, you know. I'm not sure, you know, and I'm not sure, you know, that the info is out there in the public markets. If I had to guess, you know, I'd say, you know, the new CEO, CJ Desai, he's an operator, you know, and he gets out in the field, he talks to customers, and he sets the tone on, you know, what happens in the sales organization, no matter who the head of sales is. And so, you know, my sense is there's probably some degree of, if not outright friction, just lack of alignment between those sales leaders. The head of field ops also left. So lack of alignment between the CEO and the sales leaders and whether they got pushed out or whether they decided to leave, it's unclear.

23:08Tom Schmidt:But I'd probably most likely chalk it up to kind of alignment with the CEO. Yeah.

23:15Stephanie Palazzolo:Now you talked about CJ being out in the field. We actually, we had him on our show a couple months ago and he said he was spending a lot of time talking to customers. And one of the points that he made on the call last night was in those conversations with customers, something that has come up is that these agentic workloads or basically the agentic products that everyone is waiting for enterprises to adopt. He said, it's really not happening in the ways that investors might hope. And I was struck by the comments because it was some of the most candid comments that we've heard from CEOs talking about this.

23:50Stephanie Palazzolo:And I wonder what you made of that. I mean, look, I'm not going to say that the stock drop was because of those comments, but MongoDB, this is an infrastructure company that I would have thought would have at least had a little bit of a tailwind from people adopting AI.

24:05Tom Schmidt:Yeah. Yeah. Well, Kash, I think you hit the nail on the head there. You're spot on. And I was struck by the same comment as well. And I think the surprising thing to me about the comment isn't the content of the comment. It's the forthrightness of that commentary, which echoes a lot of our checks in the field. Certainly indicate that over the course of the last 12 months, adoption of a Gentic has been slower than what people initially thought maybe a year ago. So, you know, that's fairly clear. And there's a whole host of factors. But I think Mongo, you know, the CEO coming out with that was maybe surprising.

24:50Tom Schmidt:But keep in mind, like, there's not a whole lot of traction yet from what we can see with their AI products in the enterprise. They're just starting to get some traction marketing it to the AI native privates, you know, which Mia Culpa, they made a Mia Culpa, said they should have done that. a year ago or two years ago. So they want to probably some motivation to explain why there's not more traction with enterprises. But I think his comments about the backdrop are largely true.

25:23Stephanie Palazzolo:Great. And last question for you, Steve. I always try to get a little bit clearer on what the actual products are that these companies are. Can you try to explain to us, as if you were talking to the smartest person you know outside of tech, What is the actual database software that MongoDB actually sells?

25:40Tom Schmidt:Yeah, Mongo sells a really differentiated database product. So, you know, this is data management and it helps companies persist data. And Mongo's database, their key product, Atlas, runs in the cloud. And it's designed to power operational workloads. So what that means is when companies have transactional applications, you know, whether it's e-commerce or supply chain applications where people are reading and writing data to manage business operations as opposed to like analytic or data warehouse applications. That's what Mongo is really used for. And then over the last couple of years, they've supplemented that product with acquisitions and internal development to help it be useful in really agentic use cases where you're going going to also put AI against those operational data stores.

26:33Tom Schmidt:So that's really what they're all about.

26:35Stephanie Palazzolo:And do you think that Mongo is going to be a winner in the AI era here? Or are you thinking that today's stock drop is actually reflective of what's to come?

26:44Tom Schmidt:Yeah. Well, I think the AI strategy, it's still nascent. There's more products, you know, products they need to develop. They want to become part of the reference architecture for people, for enterprises. that are implementing agentic AI and for the AI natives that are developing, you know, frameworks and LLMs, right? And that's, it's still really early days for Mongo to be relevant there. And I'm going to plead agnostic on that. I think the verdict is still out there. And, you know, I think investors are going to need a lot more proof that there's actual traction here in terms of monetization, you know, either with the AI natives and or with enterprises.

27:25Tom Schmidt:Great.

27:26Stephanie Palazzolo:Well, Steve, I want to thank you for coming on. That is Steve Koenig from Macquarie here on TI TV. The big AI funding rounds are not showing any signs of stopping. Basis, an AI agent's accounting company, recently raised$100 million led by Excel at a$1.15 billion valuation. I want to bring on Matt Harp, CEO and co-founder of the company, to talk to us about what he is building. Matt, welcome to the show. It's great to have you here. Thank you, Akash. It's great to be here.

27:55Matt Harpe:Tell us about what you're building at Basis. Yeah, so we build an AI platform for accounting teams. So we have long-running agents that are able to actually do real work for accounting teams that allows them to automate a substantial portion of the manual work that's involved in doing this accounting work. We currently serve about 30 % of the top 25 firms in the country and 20 % of the top 150. and we're essentially allowing those firms to take on a bunch more accounting work on the back of these AI agents.

28:27Stephanie Palazzolo:And how did you get into accounting here? What do you have accountants in the family? Were you an accountant in a past life? How did you get so passionate about this space?

28:35Matt Harpe:Great question. Well, I personally have no background in accounting. Mitch, who I started the company with, has a background in accounting and was working at an accounting technology company. My route to accounting is slightly circuitous, but maybe potentially interesting. I was focused on machine learning projects in healthcare, was working with a bunch of healthcare organizations. And I had a kind of crazy realization in that process of working with healthcare organizations, which is if you go to any hospital in the US and just ask a very simple question, which is how much does it cost us as the hospital to provide a procedure to a patient?

29:06Matt Harpe:Let's say, Akash, you're going to go get an x-ray or an MRI or something like this at a hospital system. There's really no hospital in America that can actually answer that question for themselves. And this is just a ridiculous proposition because if you're a hospital, you should probably have at least two goals. One is to increase the quality of care for people and the other is to reduce the cost of care for people. And if you can actually measure the cost to serve in the first place, you really don't know whether you're getting better or worse at that second objective over any given period of time.

29:34Matt Harpe:You don't really know how the decisions you're making as an organization are affecting one of the core outcomes of your organization. And so our view is that that is one of the core jobs of accounting. that fundamentally accounting is about structuring and systematizing all the economic activity that happens in and around an organization so that people can understand it there are certain compliance things that accountants have to do like doing the appropriate structuring and systematizing for preparing a tax return or you know other filings for preparing for an audit where there's all this other accounting work that simply doesn't get done um right could do we probably should do and so this kind of realization got me quite interested in the importance of accounting in the functioning of our market economy and led us to start thinking about what we could build.

30:12Matt Harpe:And then as we started thinking about, okay, how can we leverage the emerging abilities of these large models to sort of change the way that we work? It became very clear there was a significant opportunity to do this in accounting. And then we started building and we're fortunate to find a lot of excitement among the initial set of firms that we started working with.

30:28Stephanie Palazzolo:Okay. So that's a great story. Now it leads me to my next question, which is that, how did you get all of these investors participating in year round? Because I'm just going to read some of the names here and it's not a small list i mean excel led the round but then i mean you have coastal ventures on board then you've got lloyd blankfiend nat freeman daniel ghost aaron levy jack altman kyle vote adam d 'angelo i mean how do you get all these people on board man well we're yeah we appreciate the question and we're very fortunate to have

30:56Matt Harpe:a great group of folks uh around the table i think one of the things that uh we think is is really important is as you're trying to build a company there's so many important questions that uh come up. Oftentimes, we like to try to think about them from first principles, but there's so much scar tissue that other people have that they have experiences that they have that are useful to us as we think through these decisions. So having folks around the table that we can loop in and who have some context on the company when we come across these various items is super helpful. Right.

31:24Stephanie Palazzolo:But how did you get such an all-star roster? What did you learn about fundraising? It's a big valuation. It's a lot of money. I mean, what surprised you about the funding process? What did you learn through it? I mean, there are people watching the show that are going to be doing fundraising themselves too. How do you get these executives on board?

31:45Matt Harpe:I think I've come to realize over time that the most important thing about fundraising is just to build a great business, to have a clear vision of where you want to go, to state that vision very clearly, and then to exudicate against that vision at each sort of stage of the company, we put together a memo where we just write out, this is what we're going to do as a company. And then when we get to the next stage, we look back and say, did we accomplish those things? And what are we going to do going forward? And I think being extremely clear about what you're trying to do and then delivering against those results is a clear recipe for success.

32:18Matt Harpe:I think if you do those things, a lot of the other aspects in terms from a fundraising perspective, take care of themselves. People want to be involved in the company because they think there's something interesting going on. And so you're able to bring a great group together. So really it's as simple as that. And we've just been fortunate that a lot of folks who have great experiences in various areas have participated in the company and been great advocates for us.

32:41Stephanie Palazzolo:So you're building agents and outside of talent. What's the biggest cost for you right now? I imagine compute is pretty significant. Absolutely. For us, they're clear too.

32:52Matt Harpe:Number one is talent. Number two. Yeah.

32:55Stephanie Palazzolo:So how do you manage compute costs? I mean, I know you're early and, you know, margins are still something that you probably may want to worry about second after you develop the product. But, I mean, what's the advice that all these advisors are giving you about how to manage those compute costs, which, you know, they're kind of slow to come down?

33:14Matt Harpe:Yeah, I think there are two things to think about. The first is how do you manage compute costs today and what's the impact of that on margins going forward? I actually think there are two totally different questions. Our view, at least internally, is that the cost per unit of intelligence has dropped precipitously over the last couple of years, and we expect that to continue. I think if you believe that trying to calculate the margin profile today is useful as a point of reference, but it doesn't actually tell you that much about the margin profile going forward. The other factor, of course, is that as the abilities of these models continue to improve, the types of things that you can do continue to expand, that you can provide more value to your customers, you can take on more complex workflows.

33:56Matt Harpe:And so you're constantly doing more things as the margin profile changes. So I think it's very difficult to forecast those things. We're quite confident that if you just drive significant value, if you're able to essentially end-to-end complete a lot of these workflows, that the margin profile makes a lot of sense. And so then today, the question in terms of managing compute costs is making sure that you have good visibility into what the agents are doing, how much inference they're using for various tasks, and to make sure that you're sort of operating in the best possible way. And so we just have a system that essentially monitors that with a fair amount of granularity across all the various things that the AI is able to do.

34:32Matt Harpe:We keep an eye on that and make sure that it's in check with sort of the expectations that we have. And if it's not, then we take a look. And there are usually ways to optimize it if it's not. So that's our approach to it. I think that the question of monitoring today and thinking about long-term margins are actually largely independent, at least in terms of how we look at it.

34:46Stephanie Palazzolo:And very quickly, are you using OpenClaw at all? You're in the agent's world. Are you using it?

34:53Matt Harpe:We certainly don't use it for any of the work that we do in terms of building agents for customers. I think there are lessons.

35:02Stephanie Palazzolo:But personally, I mean, could you see a roadmap at all, you know, in which your personal use of it maybe could start to come into play with the program?

35:12Matt Harpe:That's a great question. I think there are lessons from OpenClaw about giving agents autonomy using as much intelligence as possible that probably are pervasive elsewhere and that you can learn from. We actually have a bit of a different approach, which is that we have a team internally called Atlas whose only job is to make everyone at the company 10x more efficient. And that includes me and includes everyone else at the company. A large part of what they do is they figure out what's the internal infrastructure we need to build as a company so that we can essentially let agents loose to complete all sorts of various workflows in the most secure way possible.

35:45Matt Harpe:And of course, OpenClaw, I think, has all sorts of security challenges. It has all sorts of challenges in terms of collaborating across companies. And so a lot of the internal infrastructure that we build essentially allows us to put similar, very capable, long-running agents to go work on various tasks, but in a very safe and contained way. And so I think you might call that a version of OpenClaw in some sense. It's giving it wide-ranging access to various things and sort of empowering it to take on large tasks, but doing it with core company infrastructure. And so that's part of what we've been building for almost a year at this point internally, which gets you, I think, a lot of the benefits that people have started to realize with OpenClaw.

36:20Stephanie Palazzolo:Great. Well, Matt, I want to thank you for coming on. That is Matt Harp, the CEO and co-founder of Basis here on TITV. Crypto venture capital company Dragonfly Capital last week raised$650 million in its latest venture capital fund. It is not every day that we hear nowadays crypto venture firms raising new money, especially amidst this latest crypto winter. Bitcoin is down nearly 40 % over the past six months. I want to bring on Tom Schmidt, a partner at Dragonfly Capital, to talk a little bit about what he is investing in in this moment. Tom, welcome back to the show. It's great to have you here.

36:56Stephanie Palazzolo:Thanks for having me. Okay, can you talk about how difficult it was to raise this fund? Because I mean, let's just stack the odds here, okay, for a second. And I think you know where this is going. But we've got crypto bear market, we've got VC fundraising bear market, we've got, I don't know, crypto VC fund bear market. Yes.

37:20Catherine Perloff:We like to play on hard mode. How did you do it? I think this is a little bit of a misconception or misnomer in that, yes, obviously VC fundraising has been going down. Crypto fundraising has been going down. But in practice, it's really just consolidating into the best performing funds that are winning both across crypto venture and more traditional venture. To your point, LPs are very pro-cyclical. And when you're looking at the public market, when you're looking at something like Bitcoin, Centemic tends to kind of track that. But when we look at crypto, I think really like the aperture of what we invest into with our Fund 3 and increasingly our Fund 4 is broad.

38:02Catherine Perloff:I think people are maybe over-indexing on this kind of NFT creator economy story that was in vogue a couple of years ago. But in practice, when you look at the up and coming new crypto companies, it's stuff like Polymarket, which is running on stable coins, is running on Rails, or it's stuff like Rain, which is a new company we just backed that allows you to spend stable coins with a debit card instead of going to have to have to have to off ramp through traditional banking infrastructure. And so if you look at overall investments, I mean, YC just put out a bunch of RFSs for stablecoin based startups.

38:36Catherine Perloff:It's more about, hey, crypto being this sort of underlying financial plumbing, this new sort of substrate that you're all doing all these more interesting businesses on top of versus like crypto just existing for the sake of existing.

38:48Stephanie Palazzolo:I want to get to the to the startups in a second here. But with the fund itself and the fundraising, was it mostly returning investors? Did you get new investors?

38:58Catherine Perloff:pretty much every existing LP re-upped and we got a couple new LPs as well. We're pretty institutional these days. And I think people who have a long-term time horizon, if any, see this as a great opportunity to be deploying in the space. I think crypto has died, you know, four or five times at this point. I think I've lost count. And it's kind of found a way to reinvent itself after every cycle. And it always looks a little bit different. And I think that's also why LPs like working with a fund manager who is spending day in, day out, looking at what's actually happening on the ground, finding new companies and trying to spot those new trends, which is, I think, what we've had a good track record of doing here.

39:33Stephanie Palazzolo:Now, you talked about prediction markets and stable coins as two areas that you're looking at with this new fund. Are there any intersections with AI? And I don't mean to bring everything back to AI because that's not what we try to do here. But I have been hearing that these agentic protocols that are coming up, I mean, you know, one possible way to navigate the payments issue here is with blockchain. And look, I don't know if it's the same group of people that were working in crypto that have now come to AI that are saying this or if there's actually potential here. But have you seen startups that are working on this?

40:09Stephanie Palazzolo:Is there a real intersection?

40:11Catherine Perloff:Yeah, I think in many ways they're very complementary technologies. You know, I think if you look back at the intersection, we haven't really done any investments. They've been things that have been focused on, you know, decentralized compute, decentralized inference, decentralized training. I think for a variety of reasons, those don't really make sense. You have this sort of inherent cost to decentralized compute that just adds to the already enormous cost of training a new model or, you know, running inference on an existing model. But kind of the interesting things that we're seeing now, or to your point, more around agentic payments where, hey, if you want, you know, I think Stripe recently put out a post saying that they, you know, imagine a future payment system that's going to require a billion transactions per second.

40:55Catherine Perloff:When you have all these agents making micropayments, you know, buying a fraction of an API or doing cross-border payments, it makes sense they would maybe want something that is global and programmable and 24-7. You're seeing things like Hyperliquid and LiDAR, which are two perp-dexes, really leading the market. I mean, even this weekend with the news in Iran, people are trading commodities pre-open on these decentralized futures platforms. And so you can get a sense of what the market sentiment is going to be before the futures open on Sunday. And I think, you know, interestingly, there's also this overlap of personnel between crypto and AI.

41:28Catherine Perloff:People forget, you know, Sam Altman was also a co-founder of WorldCoin, which is a, you know, decentralized humanity verification startup. And recently, I think there was a leak or a post, I think maybe the information picked it up actually, that they're looking at doing some collaboration with OpenAI to create a human-only social network. And so it seems like there is going to be things that's kind of overlap between the two. I think people are also just excited about distributed compute. So for us, we're an investor in Exo, which is a company that allows you to basically shard inference across multiple different Apple Silicon devices on your network.

42:02Catherine Perloff:So if you want to run, you know, an open source model that's kind of beefy, you don't have to go and buy like a really, you know, beefy, you know, GPU or like a, you know, H200 or something. You can just run this on, you know, not to meme too much, but a Mac mini or a couple Mac studios that are running on your network. And, you know, that allows you to really take advantage of edge compute. So I think the two will continue to collide, you know, naturally in a world where there's insane abundance and insane just flooding of content and things coming out of AI. Crypto is sort of this natural scarcity function, this natural sort of gating function.

42:35Catherine Perloff:And we're looking for ways that there's going to continue to collide in front of war.

42:39Stephanie Palazzolo:On the talent piece, how much harder is it to get the smartest people to come work at these crypto startups now, given that now there's this other shiny thing that wasn't really in vogue three, four years ago?

42:52Catherine Perloff:The talent wars are very real. And we do see, again, talent going back and forth between the two. I would say sort of mainstream crypto these days is actually competing more with traditional finance and financial services and pulling people out of those. So when we see people, you know, leaving JP Morgan or American Express or Visa and going into crypto, that's really more where the industry is going. It's kind of building this new sort of financial substrate. And so, I mean, you're right that, you know, hey, talent is scarce. And, you know, I think people see those multimillion dollar comp packages coming out of open AI.

43:25Stephanie Palazzolo:but um well even for payment i mean i'm just thinking about payments here you know somebody is working at jp morgan let's say or a big bank they have an option to go work at a crypto company or they could go work in this thing agentic commerce agentic payments you know open ai's building i i don't know i just feel i i feel like um it's it's hard yeah i i think the two are are

43:49Catherine Perloff:you know really again you know one of the same if you look at what's leading the road uh or leading the way in agentic payments. It's people implementing X402, which is this new standard for doing payments over the internet, Stripe's adopting it, Coinbase is adopting it. And so, if you think about, hey, where is the future of commerce going to go? It's probably going to want something programmable, something definite, something global, something you can custody. And already, I think we're seeing a lot of companies coming out of accelerators, coming out of seed, focused on this part of the market.

44:19Catherine Perloff:So, who knows? Maybe the future is also you get one dude in a garage vibe coding, some sort of thing. I think that's maybe more likely than not.

44:31Stephanie Palazzolo:Right. Great. Well, Tom, congrats on the fun. I want to thank you for coming on. That is Tom Schmidt, a partner at Dragonfly Capital here on TI-TV. That does it for today's show. A reminder, we are on this stream Monday through Friday at 10 a.m. Pacific, 1 p.m. Eastern. I want to thank you all for tuning in. We really do appreciate your viewership. Make sure to subscribe to the information on YouTube and follow us on x instagram and tiktok check us out wherever you get your podcasts i'm already excited for our next show tomorrow have a great rest of your tuesday bye-bye for now

From the publisher

AI Reporter Stephanie Palazzolo talks with TITV Host Akash Pasricha about OpenAI’s Pentagon deal, Anthropic’s stance and the AI talent war in Washington. We also talk with Catherine Perloff about Amazon’s plan to power ads inside AI chatbots and Basis CEO Matt Harpe about building AI agents for accounting and raising $100 million. Then we speak with Tom Schmidt about Dragonfly Capital’s new crypto fund and how AI and crypto intersect. Lastly, we get into MongoDB’s stock plunge, AI guidance and “agentic” workloads with Macquarie’s Steve Koenig.


Articles discussed on this episode: 

https://www.theinformation.com/articles/amazon-explores-helping-apps-sell-chatbot-ads

https://www.theinformation.com/newsletters/ai-agenda/openai-anthropic-execs-center-pentagon-action

https://www.theinformation.com/newsletters/the-briefing/anthropic-stands-gain-pentagon-stance


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