The Aboard Podcast

Same as it ever was: On this week’s podcast, Paul and Rich take a spin through a 1980 issue of Omni magazine, comparing how computers were being discussed back then with how AI is talked about today. Featuring an essay by Frank Herbert (yes, of Dune), IBM’s early-80s consumer pitch, and a meditation on the question: What does “new technology” even mean?

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 Anthropic to, in Paul’s words, “Agents, agents, agents, agents, agents.” 

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, including a meditation on the humble Dipsy Doodle.

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 make sure they’re actually learning, rather than just copy/pasting? 

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, ethical concerns, and where they’ll leave users in the coming years.  

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 their skills gathering context and asking the unexpected questions would be impossible for even the most well-trained AI to match. 

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.”