The Aboard Podcast

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AI Advice for the Confused CEO May 27, 2025

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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.

Help Wanted: AI-First Companies Need Humans After All May 20, 2025

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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.

School’s Out Forever May 13, 2025

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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?

Patrick Austin: AI’s Not There Yet May 06, 2025

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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.

A Database Will Never Love You Apr 29, 2025

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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.

Could We Replace the Pope With AI? (God, No) Apr 22, 2025

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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.”

AI is Part of Your Job Now Apr 15, 2025

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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.

The Big Crash Apr 08, 2025

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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.

Boring is Thrilling Apr 01, 2025

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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.

Prompts, Promptly Mar 25, 2025

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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?

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