Can two people who host a podcast subtitled “software in the age of AI” go half an hour without bringing up the term? On this week’s episode, Paul and Rich attempt to talk about something—anything—tech-related that isn’t AI. Topics discussed include the new Ferrari, the rise of sports gambling apps, youthful rebellions past and present, and the wonder that is the Virtual OS Museum. Do they make it through without mentioning LLMs? You’ll have to listen.
Jun 02, 2026•31 min•Season 2Ep. 209
Sure, AI might bring on the end times—but you can use it to build your own tax software! On this week’s podcast, Paul and Rich are joined in the studio by Craig Mod, a writer, photographer, and self-described “software supertaster” who recently took to Claude to build a version of Quicken that suited his complicated tax-filing needs. First, they discuss the project and assess how likely it is that a non-technologist would be able to create something similar with the current tools. Then, the conv...
May 26, 2026•48 min•Season 2Ep. 208
Doctors might be using AI to cut down on paperwork, but can these tools really be employed in clinical settings? On this week’s podcast, Paul and Rich sit down in the studio with Dr. Kamal Menghrajani, a practicing oncologist and lecturer at Harvard Medical School who was previously a member of the Biden White House’s “Cancer Moonshot” team. After she explains how AI is helping in her work, she lays out its real limitations—and discusses how these technologies can distract from more systemic app...
May 19, 2026•41 min•Season 2Ep. 207
Why are so few engineering teams reaping the benefits of AI? On this week’s episode, Paul presents Rich with the findings from a recent report from CircleCI and Thoughtworks on the productivity of enterprise teams using LLMs. While there’s been a dramatic increase in throughput—the amount of code produced—across the board, just 5% of orgs are seeing real gains from these tools, while the majority struggle with errors, bugs, and lower productivity than before AI was introduced. As Paul puts it: “...
May 12, 2026•27 min•Season 2Ep. 206
What’s wrong with Sam Altman? Ask the guy who spent 18 months reporting on him. On this week’s podcast, Paul and Rich are joined by New Yorker staff writer Andrew Marantz, who recently put out a lengthy article on the OpenAI chief that he co-reported with Ronan Farrow. After they dive into some of the specific details of the piece, they discuss the broader questions Altman’s position in the industry raises. If AI really is as powerful as he claims it will someday be, why are we allowing one pers...
May 05, 2026•48 min•Season 2Ep. 205
What does it take to make a really good product with AI tools? On this week’s podcast, Paul walks Rich through his recent adventures building a robust aggregated newsletter tool—first to track the AI industry, then generalized and customizable for any industry. Vibe-coding platforms continue to evolve, but you still need a lot of technical knowledge to make something that really works. Is that high bar likely to lower in the coming months and years?
Apr 28, 2026•38 min•Season 2Ep. 204
“The blind vibe-coding revolution is upon us.” On this week’s podcast, Paul and Rich are joined by Andrew Leland, the author of the Pulitzer-finalist The Country of the Blind: A Memoir at the End of Sight , to discuss how blind and low-vision people are using AI tools to create and adapt software to suit their accessibility needs. With limits to what any out-of-the-box software or device might do, is AI the way to give disabled people technological solutions that really work? Plus: Rich bravely ...
Apr 21, 2026•47 min•Season 2Ep. 203
Employees at the big consulting firms are being told to use AI. Are they going to automate themselves out of a job? On this week’s podcast, Paul and Rich discuss a recent set of directives from the CEO of PricewaterhouseCoopers about AI adoption and consider what they frame as the “AI consulting paradox”: To show value, consultants need to introduce AI into their client relationships, potentially cutting their own value as a result. How will consulting manage this transition in the short or long...
Apr 14, 2026•35 min•Season 2Ep. 202
Sure, you can build “stuff” with AI, but is anyone paying attention to product these days? On this week’s episode, Paul and Rich sit down with someone who is: Hilary Mason, CEO of the immersive online roleplaying game company Hidden Door. After discussing Hilary’s background in data science and machine learning, Paul takes a spin through a game scenario (Brooklyn vampires in a fantasy tavern!) while Hilary outlines the product decisions around Hidden Door’s game mechanics, AI-related or otherwis...
Apr 07, 2026•43 min•Season 2Ep. 201
AI is blurring—and even destroying—the distinctions between disciplines. Do we need a new way to talk about work? On this week’s episode, Paul tests out a few of his AI-era neologisms on a skeptical Rich: Perhaps you are a “custolient,” looking to purchase the services of a “praygency” for your next project? (Yes, Paul insists the “y” in “praygency” is vital.) Are these new blended terms helpful, or just a way of talking around a very uncertain landscape?
Mar 31, 2026•30 min•Season 2Ep. 200
Is the future of work sitting back and watching your company of bots plan their offsite? On this week’s episode, Paul is joined in the studio by journalist Evan Ratliff, the host and creator of the wildly popular Shell Game podcast, which is about, per the show’s description, “how Evan tried to build a real startup, run by fake people.” Evan’s AI agents were an exercise in immersive journalism (and yes, they did in fact go wild planning their offsite), but would he ever consider running a compan...
Mar 24, 2026•46 min•Season 2Ep. 199
With AI drastically cutting delivery times in tech and beyond, how should practitioners price their time? On this week’s podcast, Paul tells Rich about a recent experience with a potential client, where he skipped steps and rapidly vibe-coded through the prototyping process and they….didn’t really know what to make of the result. If things that used to take months can now be done in hours, what are clients actually paying for?
Mar 17, 2026•33 min•Season 2Ep. 198
Can AI help heal our broken healthcare system? On this week’s podcast, Paul and Rich are joined in the studio by Erynn Petersen, a longtime technologist and the current CEO of Emme, a healthtech startup that works to lower medical costs for both providers and patients. First, she lays out some of the systemic problems that saddle Americans with huge bills (or lead them to avoid seeking care entirely). Then, she discusses how AI tools might revolutionize the industry—as well as the ways the techn...
Mar 10, 2026•44 min•Season 2Ep. 197
People are constantly talking about how AI is transforming engineers’ work, but where does that leave the product manager? On this week’s podcast, Paul (who has hired many PMs) and Rich (who is also a PM himself) tilt the AI-and-code lens away from the engineers and onto the role they describe as the diplomat of software creation, liaising between business, design, and engineering needs. Should PMs feel threatened by LLMs, or empowered by them? How can they use these tools to add value to the or...
Mar 03, 2026•26 min•Season 2Ep. 196
Public opinion on LLMs like Claude varies widely—but how do the people who actually work at Anthropic think about it? On this week’s podcast, Paul and Rich are joined in the studio by New Yorker staff writer Gideon Lewis-Kraus to discuss his recent feature, which he reported from within Anthropic HQ. They discuss the piece, and then they hash out the real questions: What’s the correct literary metaphor for an LLM? Does an AI company really need psychologists for its chatbots? And, perhaps most i...
Feb 24, 2026•41 min•Season 2Ep. 195
Anthropic founder Dario Amodei wants AI to be regulated. Will anyone listen? On this week’s podcast, Paul and Rich dive into Amodei’s recent (lengthy) essay, “The Adolescence of Technology,” which argues for social responsibility both from within and around the AI industry. Amodei might have the best intentions, but with less mindful competitors in the space, are his ideas nothing more than wishful thinking?
Feb 17, 2026•37 min•Season 2Ep. 194
Is Moltbook—aka “Reddit for Robots”—merely a novelty, or does it contain bigger ideas about the future of tech? On this week’s podcast, Paul and Rich start by discussing the autonomous agents of OpenClaw before they move on to Moltbook, the social network where said agents can hang out. (No humans allowed!) How do these LLM developments fit into the broader history of the web, and what do they suggest about where AI might be headed?
Feb 10, 2026•36 min•Season 2Ep. 193
AI is poised to transform the healthcare sector—but what does that mean in practice? Fresh off hosting a healthtech event in Aboard’s Manhattan offices, Paul and Rich talk through the ways AI is reshaping this massive segment of the American economy. AI might lead to breakthroughs for researchers and diagnosticians alike, but is its real superpower…cutting down on paperwork? Plus: What happens when every patient arrives at their appointment armed with a diagnosis from Dr. ChatGPT?
Feb 03, 2026•35 min•Season 2Ep. 192
“I built it in six hours. Let’s deploy it to production!” On this week’s podcast, Paul and Rich engage in one of their favorite pastimes: Corporate roleplay. Taking on the personas of Doug, a vibe-coding engineer, and (Mr.) Jeremy, his skeptical boss, they act out a scenario that’s surely unfolding at organizations large and small right now. Doug might be too hasty when he declares his vibe-coded software ready for client use, but is Jeremy actually being too cautious?
Jan 27, 2026•24 min•Season 2Ep. 191
Claude Code has emerged as a true development tool—but will non-tech people actually use it? This week on the podcast about “software in the age of AI,” Paul and Rich discuss, well, software in the age of AI: Specifically, what the rise of Claude Code means for the world of software on a whole. Are we really at a point where a layperson could create the software they need via a prompt? And if we are, what are the barriers stopping people from doing so today?
Jan 20, 2026•30 min•Season 2Ep. 190
How is one of the internet’s biggest spaces for human creativity adapting in the AI era? On this week’s podcast, Paul and Rich are joined in the studio by Rafe Colburn, the Chief Product and Technology Officer at Etsy. After discussing Rafe’s long history at the company, they tackle the AI topic two ways: First, how the Etsy engineering org is using AI tools, and second, Etsy’s recent deal with OpenAI to display their products directly in ChatGPT searches. Plus: Rafe and Paul teach Rich the prop...
Jan 13, 2026•36 min•Season 2Ep. 189
What will the AI story be in 2026: Society-wide transformation or incremental change? On the first podcast of the new year, Paul and Rich (gently) argue over what they expect to see in the AI space over the coming months. These tools might allow people to build software far faster than before, but how much will that disrupt the industry itself? Plus—perfect for a podcast full of tech predictions—they discuss why humans are terrible at predicting the future of tech.
Jan 06, 2026•29 min•Season 2Ep. 188
AI is transforming what we buy—and how we buy it. On the final podcast of the year, Paul and Rich are joined by Dan Frommer, founder of The New Consumer , to talk through his brand-new Consumer Trends Report for 2026. First, they discuss shifting consumer dynamics over the past few decades, from the rise of digital-native direct-to-consumer brands to the omnipresence of the TikTok Shop. Then, they dig into New Consumer survey results around our current moment in AI, particularly the generational...
Dec 16, 2025•40 min•Season 2Ep. 187
Is there space for everyone in LLM world? On this week’s podcast, Paul and Rich traverse the always-changing AI landscape from one end of the spectrum to the other. First, the Christian LLM company Gloo, currently headed by former Intel CEO Patrick Gelsinger, which is building technologies for the “faith ecosystem.” Then, Sam Altman’s recent announcement that OpenAI will begin producing erotic content for verified users. In one version of our AI future, there’s room for lots of smaller companies...
Dec 09, 2025•25 min•Season 2Ep. 186
AI is reshaping the media, the internet, and the culture at large—and Max Read is writing about it. On this week’s podcast, the longtime journalist and author of the popular “Read Max” newsletter comes into the studio to talk about the intersections of tech and culture in our current AI moment. Topics discussed include Max’s journey from a general-interest journalist to covering tech platforms and internet culture, the ways he uses AI tools in his own work, and whether he thinks the slop floodin...
Dec 02, 2025•34 min•Season 2Ep. 185
The AI industry teeters on the edge of the bubble, but AI tools are better than ever. What does this mean for the future of the technology? On this week’s podcast, Paul and Rich talk through Paul’s recent experiments with—you guessed it!—synths to illustrate just how good AI-assisted coding tools have gotten, especially for those with programming expertise. But we’re a long way from the average consumer being able to get what they want with the push of a button. What do these two divergent paths...
Nov 18, 2025•26 min•Season 2Ep. 184
As people feed their whole lives into LLMs, how can they protect themselves? On this week’s Aboard Podcast, Paul and Rich are joined by Arushi Saxena, a trust and safety expert who’s worked everywhere from big tech to startups to the U.S. government. What does trust and safety mean in the AI age, both for individuals and for companies working with LLMs? Arushi also gives an overview of the trust and safety world, but sorry, folks: What happens at TrustCon stays at TrustCon.
Nov 11, 2025•38 min•Season 2Ep. 183
Big tech doesn’t care about medium-sized businesses—but is AI really the solution? On this week’s podcast, Paul is fresh off the plane from Phoenix, Arizona, where he was speaking to business owners at the Inc. 5000 Conference. As he gives Rich a full report, they discuss the specific needs of the “SMB”—small-to-medium-sized business—and how little interest the software industry has in the very large middle of the business spectrum. Can AI help these orgs get the software they actually need?...
Nov 04, 2025•26 min•Season 2Ep. 182
AI is making job hunting near-impossible on both sides of the hiring equation. Is there a way out of this automated mess? On this week’s podcast, Paul and Rich look at AI’s effect on an already unpredictable job market. Hirers are getting spammed with AI-generated applications, while sincere job seekers are getting swiftly rejected via AI hiring tools. As AI ushers in a hyper-transactional era of diminished trust between strangers, how can applicants and hiring managers actually connect with eac...
Oct 28, 2025•29 min•Season 2Ep. 181
Traffic to vibe-coding tools is plummeting. Financial analysts are invoking 1929. Is the big AI crash inevitable? On the latest Aboard Podcast, Paul and Rich assess our current moment in AI and its (over)valuation in the global economy. Will the bubble pop—and if it does, how big will that pop be? And as they evaluate the problems with our lopsided AI landscape, they speculate about what AI as a technology—rather than an investment vehicle—could look like in the future.
Oct 21, 2025•31 min•Season 2Ep. 180
