The Aboard Podcast

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Kurt Schrader: Shipping AI at Shortcut Mar 18, 2025

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As AI transforms the way engineers build software, how is it changing the software that’s built for engineers? On this week’s Reqless, Paul and Rich welcome Kurt Schrader, the CEO and co-founder of the engineering-management platform Shortcut. Topics discussed include what it’s like to integrate AI into engineering-team workflows, why he thinks AI will actually force the engineering skill bar higher in the future, and building Korey, Shortcut’s forthcoming AI tool.

The AI Centrist Mar 11, 2025

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Some people hate AI and think it’ll destroy everything. Others love it and want to press their feet on the AI gas pedal. What happens if you’re stuck in the middle? On this week’s Reqless, Paul lays out his “AI centrist” approach to thinking about these technologies—how to continue to experiment with these tools, while being open to all arguments about them. Plus: Rich sings the praises of everybody’s favorite agrochemical conglomerate, Monsanto (well…not exactly).

Sara Chipps: How AI Changes Coding Mar 04, 2025

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What should developers be doing right now to adapt to AI? On this week’s Reqless, Paul and Rich get an on-the-ground perspective from longtime software engineer Sara Chipps, who’s been going deep with AI-assisted coding tools in recent months. They discuss what AI means for the work of everyone from recent CS grads to senior engineering managers, before they shift topics to Sara’s true passion, using AI to better trade crypto, which leaves Rich uttering the phrase, “What’s the market cap of Fartboy?”

AI Regulation (and Disregulation) Feb 25, 2025

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Is it too late to regulate AI? On this week’s Reqless, Paul and Rich assess what “regulating AI” could even mean, from controlling training data sources to moderating its ability to spread information—and disinformation. They then zero in on the question in the context of the new American administration, and Paul muses about just how long he’d like to hold his breath underwater given the current state of the news. (Five minutes? Ten?)

Clay Shirky: AI for Higher Education Feb 18, 2025

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How is generative AI transforming the university? On this week’s Reqless, Paul and Rich sit down with someone on the front lines of AI in higher ed: Clay Shirky, a longtime educator and technologist who’s currently the Vice Provost of Educational Technologies at New York University. Clay outlines how the university’s approach to AI has shifted from semester to semester over the past few years, and then digs into the reasons why widespread student adoption of AI is worrying the faculty—and the students themselves.

Waiting for the DOGE Barbarians Feb 11, 2025

Show notes

Government by Grok? On this week’s Reqless, Paul opens with a poetry reading (stay with us) and then he and Rich discuss the poem’s relationship to Elon Musk’s DOGE effort, currently ransacking the U.S. Treasury. The DOGE strategy seems to be “destroy without oversight, replace with AI,” which leads to two questions: Could this work? (No.) And if you are going to take a sledgehammer to bureaucracy, is there an ethical way to swing the hammer? (Eh…)

AI as an Accelerant for Good Feb 04, 2025

Show notes

How is AI transforming the social sector? Flying solo in the Reqless hosting chair, Paul sits down with Perry Hewitt, Chief Marketing and Product Officer for Data.org, to talk about how AI tools are enhancing the projects they support. Topics discussed include what data collection can entail in the world of global nonprofits, the impact of constraints on technological problem solving, and real examples of how AI is being used right now, from healthcare settings in India to the wildfires in Los Angeles.

Don’t Freak About DeepSeek Jan 28, 2025

Show notes

As Chinese LLM company DeepSeek makes headlines for wreaking havoc on the stock prices of the American tech sector, Paul and Rich sit down and answer the important questions: What is DeepSeek? Why does Paul feel like it’s Christmas? What does this mean for both AI and the broader industry? What does Rich think Microsoft should do with Three Mile Island now?

Brains Are Better Than Butlers Jan 21, 2025

Show notes

AI tools are often positioned as agents, assistants, or butlers—but their potential is so much greater than that. On this week’s Reqless, Rich explains to Paul why the “agent” model gets AI all wrong. Plus: A discussion about CTOs, and the spectrum from those who are resisting the change that’s coming to those who are embracing it.

Not Quite Finishing Apps Jan 14, 2025

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Can you actually build an app with AI right now? Fresh off a holiday break where he attempted to do just that (rather than talking to his family), Paul tells Rich what worked and what didn’t work in his experimentation: Where AI failed, where Paul got impatient, and how that mapped onto human programmers’ strengths and weaknesses. Building an entire app with AI might not be quite there yet—but is it close?

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