
Reqless: Software in the Age of AI
AI is changing how we build software—for the better, for the worse, and in ways to be determined. In this podcast, two surprisingly entertaining software veterans go piece by piece, exploring how change is coming: for industries, for individuals, and always with a focus on how to put things into perspective, then put them into action to move your career along. Say goodbye to the endless requirements phase, say hello to building software as-needed—it’s time to get REQLESS.
Latest episodes

Apr 22, 2025 • 28min
Could We Replace the Pope With AI? (God, No)
Does AI have a place in religion—or in our moral decision-making more broadly? Recorded shortly after the death of Pope Francis was announced, Paul and Rich reflect on the pontiff’s legacy and then segue to theology and tech, assessing ChatGPT’s output to moral queries “from a Catholic perspective.” Could these tools ever be a substitute for the real (human) thing? Featuring what’s possibly the most upsetting sentence ever uttered on the podcast: “I wanna see Peter Thiel wash some feet.”

Apr 15, 2025 • 30min
AI is Part of Your Job Now
Shopify CEO Tobi Lütke recently told his employees that AI use is now mandatory—and on this week’s Reqless, Paul and Rich talk about why they think this is a good directive for every worker. After they discuss the substance of Lütke’s “leaked” memo and contextualize it within the broader industry trends, they count down five concrete tips for anyone who wants to incorporate AI into their work and isn’t sure where to start.

Apr 8, 2025 • 28min
The Big Crash
As Trump’s tariffs become reality and global markets plummet, Paul and Rich take stock of the situation and ask: How are the founders of an AI startup thinking about the months ahead, and how can AI help businesses weather the storm? Plus: As they look back at the early-2000s dot-com crash, they discuss how tech innovation can blossom in times of economic uncertainty.

Apr 1, 2025 • 27min
Boring is Thrilling
When Rich asks Paul for a report from the AI-coding trenches, Paul brings news: AI is boring now! And that’s a good thing. As the novelty of the technology wears off and the pace of advancement stabilizes, it’s getting easier and easier to actually get work done. Plus: Paul gets nerdy (well, even nerdier than normal) and walks through the specifics of the data-migration project he’s working on to show how AI’s boring turn is affecting real-word software work.

Mar 25, 2025 • 26min
Prompts, Promptly
On this week’s Reqless, Paul and Rich consider the prompt: What it represents within generative AI tools, how they think about it as users, and what it means for Aboard as a product. Is the prompt the end state of engaging with AI, or will the way we interact with these tools continue to evolve?

Mar 18, 2025 • 32min
Kurt Schrader: Shipping AI at Shortcut
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.

Mar 11, 2025 • 21min
The AI Centrist
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).

Mar 4, 2025 • 36min
Sara Chipps: How AI Changes Coding
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?”

Feb 25, 2025 • 34min
AI Regulation (and Disregulation)
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?)

Feb 18, 2025 • 37min
Clay Shirky: AI for Higher Education
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.
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