The Aboard Podcast

As the legacy tech giants weave AI functionality through their existing systems, is it all over for AI-first companies like OpenAI and Anthropic? In the wake of this year’s WWDC, Paul and Rich analyze Apple’s AI plans, and contextualize them within broader industry shifts. What’s Apple’s AI endgame—and where can we expect to see a player like OpenAI a few years from now?

When is something “done”—and why is it so hard to define “done” when it comes to AI? On this week’s podcast, Paul and Rich talk about the challenges of the last mile of software development, and why the industry needs a whole new set of processes to actually use AI to ship product. Plus: Paul reveals one neat trick that will make you finish writing something.

OpenAI’s $6.5 billion acquisition of Jony Ive’s startup might be grabbing the headlines, but the real shifts in AI right now are a lot less flashy—and point towards more long-term stability in the industry. On this week’s podcast, Paul walks Rich through some recent Big AI news and they pull out some key trends and takeaways, from the announcements at Google’s I/O 2025 to new capabilities at Anthr...

The CEO comes into the office and says, “What are we doing about AI?” What’s wrong with this picture? On the podcast, Paul and Rich offer advice to the CEO whose instinct is to ask that very question. How should business leaders be thinking about these technologies? And when it comes to getting AI into your organization, what’s a better question to ask? Plus: A whole lot of snack-chip talk, includ...

Last year, the fintech company Klarna announced they were going AI-first—but now, they’re hiring humans again. Is this a sign that the AI pendulum is swinging back in tech? On this week’s podcast, Paul and Rich look back at Klarna CEO Sebastian Siemiatkowski’s initial pivot, why that strategy probably didn’t get the job done, and what this move signals for the industry on a whole.   

Today’s young people are growing up with generative AI at their fingertips. Should we be worried? On this week’s podcast, Paul (father of 13-year-old twins) and Rich (father of a 12 year old and a 10 year old) discuss the technology world in which their children are coming of age, particularly when it comes to education. If students are bound to turn to these tools no matter the rules, how can we...

From your inbox to the podcast studio: Paul and Rich are joined by Patrick Lucas Austin, longtime tech journalist and founding editor of IT Brew, to talk about how he views AI in his work covering the enterprise sector. While Paul and Rich consider themselves “AI centrists,” Patrick takes an arguably more critical view of these technologies, and they go back and forth on the capabilities, outputs,...

Are product managers’ jobs safe in our new AI-development reality? Paul and Rich discuss the news that OpenAI is looking to acquire the coding assistant Windsurf, asking the question: If AI is excellent at coding, why would OpenAI need to integrate a coding assistant into its products? This leads them to the role of humans in AI-aided software development—especially the product manager, and how th...

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 mo...

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...

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.

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...

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?

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 high...

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 everybo...

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, us...

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 s...

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...

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 burea...

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 exa...

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?

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. 

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...

Does the world actually need more software? In the first Reqless of 2025, Paul and Rich skip the “AI predictions for the coming year” and instead look at the tech landscape for smaller organizations. Do they really have the tools they need to get their work done? Featuring extensive corporate roleplay—including Paul’s very believable turn as a big-firm consultant—and a meditation on New York City’...

Farewell 2024—a boring year in which nothing really happened! On this week’s Reqless, Paul and Rich reflect on our current moment of widespread instability, from the cultural to the political to the technological, and discuss some of the ways they try to manage it (waffles!) (also building software). And because this is an AI podcast, they look back over a year of rapid change in the space, and ma...