POLITICO Tech — “Why AI companies are cutting Trump a deal”

Date: September 4, 2025
Host: Stephen Overlea
Guest: Aaron Levy, CEO of Box

Episode Overview

This episode explores the remarkable trend of AI companies offering massive discounts—sometimes as little as $1—for their services to the federal government under the Trump administration's new OneGov program. Host Stephen Overlea speaks with Aaron Levy, CEO of Box, to unpack why these deals are happening, how business and policy incentives are aligned, what the federal government stands to gain, and what the future may look like as AI becomes more embedded in U.S. government operations.

Key Discussion Points & Insights

1. The OneGov Program and AI Procurement

• Centralized Buying for Efficiency: The Trump administration’s OneGov program is consolidating tech acquisition across agencies, enabling bulk discounts and faster modernization.
  • Aaron Levy (02:02): "There's been a kind of a procurement efficiency, cost savings orientation of this administration that I think has been fairly effective."
• A Push for Modernization: The government sees this as an opportune moment to implement AI widely, as the tech is now mature enough for deployment at scale.
  • Aaron Levy (02:50): "The AI push is sort of uniquely timed for the moment when AI is actually ready to be used really in federal agencies for the first time."

2. The $1 AI Deal and Business Incentives

• Discounts Across the Board: While some companies (like OpenAI) are offering their flagship AI tools (e.g., ChatGPT) for $1 per agency, Box provides deep discounts—65-75% off normal rates—enabling even small agencies to get enterprise-level services.
  • Aaron Levy (03:45): "It's a way of really unifying the volume pricing structure for agencies of all sizes and for any kind of use case in the government."
• Why the Deep Discounts? For AI vendors, it’s a classic “get-in-the-door” strategy. Widespread adoption today could lead to stickiness—and revenue—tomorrow as government reliance on these tools grows.
  • Aaron Levy (05:54): "The dollar thing is probably a little bit of a kind of seeding strategy to ensure that more people use the technology and can start to use these tools and build more fluency with AI."
  • Stephen Overlea (06:39): "Part of the motivation for some of these companies breaking into the government was get in the door, get people using it and then, you know, you can charge more later once it's proven its worth."
• This Isn’t Just About the Federal Government: The approach (discounts to drive mass adoption) is happening across sectors, with government being a particularly lucrative entry point due to its size and data needs.

3. Politics: Is This About Pleasing Trump?

• Not (Primarily) Political: Levy dismisses the idea that these deals are about currying favor with President Trump, emphasizing continuity across administrations and a business focus on supporting critical missions.
  • Aaron Levy (08:10): "I don't really see it as any kind of political move. This is purely—we've worked with the federal government for well over a decade now and we want to continue to support its broad mission."

4. Is the Government Ready for AI?

• Technological vs. Organizational Readiness: While AI is technically ready, “workflow readiness” and preparing employees to leverage new tools is a significant hurdle.
  • Aaron Levy (09:57): "Technology readiness, obviously kind of one factor—workflow readiness, IT readiness, employee readiness, totally different challenges there."
• Stark Example: If young, skilled workers join but can’t access modern tools, “we will have just squeezed out” their energy and productivity.
  • Aaron Levy (10:48): "Think about how much energy and productivity we will have just squeezed out of that person that we're not able to then tap into because we don't have the right technology for them to use."
• Mandates and Buy-In: Moving to “AI-first” operations may require top-down mandates to accelerate adoption.

5. Security and Legacy Concerns

• Challenge of Catching Up: The federal government can’t match the nimbleness of startups, but should strive to minimize the gap and leverage its unique data assets.
  • Aaron Levy (12:11): "That's a continuum. And I'd say actually there's many areas where the federal government is ahead of the private sector because of the vast data troves that they have access to."

6. Vision: The AI-Powered Government of the Future

• Indirect but Profound Effects: Direct public impact may be limited, but government efficiency in areas like FDA drug reviews, disaster response, and research processing will increase noticeably.
  • Aaron Levy (13:48): "It will absolutely continue to push the economy and push the country forward in all of these indirect ways. And that's, I think, the power in the first place of the federal government."
• Persistent, Bipartisan Push for Efficiency: The digital modernization drive has roots in Obama’s “cloud first” strategy and carried through to Trump’s “Doge” reform (with Elon Musk’s involvement), now extended via AI.
  • Aaron Levy (15:42): "Everybody can get around the idea that let's spend less in technology, let's get more efficient in our government technology operations, let's get more out of our data, let's drive more automation."

7. What’s Next? No Instant Utopia, But Steady Change

• Realism Over Hype: The road to a fully AI-driven government is “dynamic” and gradual. Automation will first impact repetitive workflows, with major advancements in security and defense expected.
  • Aaron Levy (17:30): "I think the road to some Techtopia is ... it has many ups and downs. The journey will be very dynamic. I'm not pitching any kind of instant panacea kind of outcome that AI will deliver."
• Government as Innovation Leader: In critical areas (security, defense), the government may actually lead the private sector, creating advances that later flow into broader commercial use.

Notable Quotes and Memorable Moments

• On AI Discounts as Seeding Strategy:

  • Aaron Levy (05:54): "The dollar thing is probably a little bit of a kind of seeding strategy to ensure that more people use the technology and can start to use these tools and build more fluency with AI."

• On Intergenerational Government Frustration:

  • Aaron Levy (10:35): "Imagine if you're a 21 year old that wants to go in and make an incredible impact on America and you join the government. And yet the tech stack looks entirely different from what you've been using for the past four years in college. And the tools aren't modern. You don't have access to AI."

• On Politics and Motives:

  • Aaron Levy (08:10): "I don't really see it as any kind of political move. This is purely—we've worked with the federal government for well over a decade now and we want to continue to support its broad mission..."

• On Realistic Expectations for AI Modernization:

  • Aaron Levy (17:30): "I think the road to some Techtopia is ... it has many ups and downs... The journey will be very dynamic."

Timestamps for Key Segments

• [01:49] — Opening of core discussion; what’s unique about the Trump administration’s deals with AI companies
• [02:02] — Two key vectors: centralized procurement and an AI modernization push
• [03:30] — Details on Box’s government pricing, structure of OneGov
• [05:48] — Why AI companies are dramatically discounting their products
• [07:41] — Are companies motivated by politics?
• [09:41] — Is the government workforce and infrastructure ready for AI?
• [13:40] — Five to ten-year vision: what an AI-empowered federal government could actually look like
• [15:09] — AI reforms linked to bipartisan, ongoing “Doge” tech efficiency agenda
• [17:13] — What’s next? Realistic incremental progress, not a tech utopia overnight

Tone & Language

Both Overlea and Levy keep the conversation practical and direct, foregrounding the economic and operational logic behind AI deals, while blending in policy and a dash of humor about politics (“I am a CEO who probably regrets not shying away from politics” – Levy, 07:48). The dialogue is optimistic, yet measured—emphasizing opportunities, acknowledging obstacles, and steering clear of hype.

For listeners seeking to understand why AI is floodgating into the federal government—and what that might mean for the future—this episode offers an inside look at the parade of “too-good-to-be-true” tech deals, why industry and government interests are aligning, and glimpses of the bureaucratic AI revolution now underway.