# Internal politics determine how far enterprise AI projects go

Markdown copy of https://realalpha.app/s/internal-politics-determine-how-far-enterprise-ai-projects/ on Real Alpha, the best minutes from long interviews with the people building AI. Cite and link the page, not this copy.

- Speaker: [May Habib](https://realalpha.app/builders/may-habib/) · May Habib is cofounder and CEO of Writer. · Co-founded and leads Writer, an enterprise agentic AI platform serving Accenture, Mars, Uber and hundreds more.
- Host: [Alex Konrad](https://realalpha.app/people/alex-konrad/) · Founder & editor, Upstarts Media · Ran Forbes' Midas List for ten years and co-created its Cloud 100 list; founded Upstarts in 2025.
- Show: Upstarts
- Episode: [Writer's May Habib: Building The Enterprise AI That Anthropic And OpenAI Sell — Then ‘Leave’ Behind](https://realalpha.app/v/wQGIp0KouWY/), Jun 25, 2026
- Moment: 9:16 to 11:54 of the episode (3 min), playing on https://realalpha.app/s/internal-politics-determine-how-far-enterprise-ai-projects/; the episode from there: https://realalpha.app/v/wQGIp0KouWY/?t=556

## Quote

> “And so much of the home-built stuff is **accumulating tech debt** as soon as it is launched.”
> — [May Habib](https://realalpha.app/builders/may-habib/) at [10:11](https://realalpha.app/v/wQGIp0KouWY/?t=611) · Upstarts

## Takeaways

1. Executives can be pulled between strategy and past AI spending.
2. Habib says home-built tools can accumulate technical debt at launch.
3. Aligned teams can expand plans beyond their initial ambitions.

## About this segment

May Habib says sunk costs and CIO-CMO-CEO tensions can keep companies tied to home-built GPT tools that add technical debt. In aligned organizations, teams can aim beyond an initial plan.

From “Writer's May Habib: Building The Enterprise AI That Anthropic And OpenAI Sell — Then ‘Leave’ Behind”, Jun 25, 2026. [Watch the full episode](https://realalpha.app/v/wQGIp0KouWY/)

## Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

[9:28](https://realalpha.app/v/wQGIp0KouWY/?t=568) What is the temperature in the room with these big companies that you're meeting with? Are they feeling coming from a place of negativity that they haven't realized the results that they want and you're kind of cheering them up? Are they still excited? Give us that heat check right off the top. It's such a good question because I think it's also what helps really distinguish our team as folks who will partner with these executives to get results versus folks who are speaking at them or trying to sell them something. And the answer depends on the level of politics. Like, We have been in situations where a CIO, a CMO, and a CEO are literally trying to like split the baby, right, on strategy or the sunk costs fallacy of I've already spent 20, 30, 40.

[10:12](https://realalpha.app/v/wQGIp0KouWY/?t=612) 40 mil on some internal company GPT that I feel so much allegiance to and everything I buy needs to fit into that. Well, it's not working. And so much of the home-built stuff is accumulating tech debt as soon as it is launched. And folks who are really struggling with the politics of that haven't built the kind of trust that says, look, we need to move on to the next thing and get people to move along with us. So much of the temperature really depends on, you know, is this a political organization? Has politics entered the chat, so to speak? Or is it a very collaborative organization where the executives have all worked together for a long time, they've made mistakes together, but are working in a highly iterative experimental way to do things? And depending on that, our ambition level scales with that. And so, with some of our most ambitious organizations

[11:10](https://realalpha.app/v/wQGIp0KouWY/?t=670) and Edward Jones, a Vanguard, a Northwestern Mutual, we can dream along with them. And, you know, the number of times executives or folks in the middle of the organization at those companies have said, oh, my God, like, we were going to go to level two of our plan. Thanks to you guys, we get to go to level 10 of our plan. And so, you really co-create together when there's incredible organizational health, I would say. When it's more political, it's just you get in a corner with somebody and you help make their patch as bright and beautiful as possible and