The Aboard Podcast
The Aboard Podcast, hosted by Rich Ziade and Paul Ford, explores how AI is transforming software development, business strategy, and everyday life. Each episode features conversations with guests who demystify AI topics, making them accessible and engaging. New episodes are released every Tuesday.
Episodes
Kate Lee: Can AI Replace Editors Like Me?
What would you do if your boss said he wanted your help to automate away your job? On this week’s episode, Paul and Rich are joined by Kate Lee, the editor in chief of the AI-related publication Every. Kate’s boss, Dan Shipper, has proposed just that: For the past few years, they’ve been building software to try to reliably automate major parts of the editorial process. At Every, writers and edito
Why Is It So Hard To Ship With AI?
AI has radically changed the way software is built—so why aren’t we seeing a glut of cool new products as a result? On this week’s episode, Paul and Rich browse recent app-related headlines and product announcements, searching for anything that isn’t AI-infrastructure related: What are people actually building on top of LLMs these days? (Spoiler: Not much.) They then attempt to diagnose what’s goi
Tricia Wang: Verification and Trust in the AI Era
“Verification cannot belong to the verified.” On this week’s episode, Paul is solo in the host chair as he sits down with longtime tech researcher Tricia Wang, the co-founder and CEO of the Advanced AI Society. Verifying AI, she explains, is far more complicated than simply dealing with hallucinations; in a world where AI is operating at a massive scale, how can we trust the outputs—or the people
Karp Carping: Decoding Palantir's Whole Deal
It might sound like he’s ranting, but the Palantir chief is zeroing in on the truth of our AI moment. On this week’s episode, Paul and Rich break down Alex Karp’s recent appearance on CNBC, in which he discussed Palantir’s position within the ever-expanding world of the AI giants. Orgs might be using OpenAI and Anthropic’s tokens, but Palantir’s position exposes, in Rich’s words, “the gap between
Father Brendan McGuire: Bringing AI to Church
How is Silicon Valley engaging with ethics and religion today—and how is the Catholic Church responding to AI? On this week’s episode, Paul and Rich welcome on Father Brendan McGuire, a former engineer and current Catholic priest who serves at St. Simon Parish in Los Altos, California, aka the heart of Silicon Valley. He discusses his long work speaking between the tech industry and the Church, as
AI Unicorns Don’t Exist
Silicon Valley “disruption” is at odds with the way software creation actually works—and that’s a problem. On this week’s podcast, Paul and Rich discuss Rich’s recent Aboard newsletter installment, “Maybe the Valley Could Listen a Little.” about how the dream of an “AI unicorn” who can use these tools to build a product all by themselves is a total fantasy. AI companies are promising revolutionary
John Herrman: The Declawing of OpenClaw
OpenClaw sprung up overnight—and seemed to fade just as quickly. What does that suggest about AI more broadly? On this week’s podcast, Paul and Rich are joined in the studio by New York Magazine tech reporter John Herrman, whose long career covering all corners of the industry has, like the rest of his peers, recently shifted to all AI, all the time. They discuss his piece for the magazine on Open
Traci Donnelly: Using AI to Make an Impact
How should nonprofits actually be using AI? On this week’s episode, Paul and Rich are joined in the studio by Traci Donnelly, the CEO of The Child Center of NY and the founder and president of Make An Impact—and a client of Aboard. After discussing these orgs’ missions, they dive into AI: Traci’s early embrace of the technology, how these tools can transform work in the sector, and the importance
LevAIthan? A Hobbesian Look at AI
Is the AI era destined to make our software lives nasty, brutish, and short? On this week’s podcast, Rich brings Paul the framing of “Hobbesian AI,” specifically from 17th century English philosopher Thomas Hobbes’s greatest work, Leviathan. Humans need some kind of order, Hobbes argued in the wake of the English Civil War, otherwise they will destroy each other. How can these lessons be applied t
Eric Ries: Lean Startup to Tech Ethicist
Is it possible to build an incorruptible company in our current system? On this week’s podcast, Paul and Rich are joined in the studio by Eric Ries, the author of the 2011 bestseller The Lean Startup, to discuss his latest book, Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great. After they discuss his tech origins and the legacy of The Lean Startup within the industry,
Challenge: Don’t Mention AI
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
Craig Mod: Vibe Coding Towards the Apocalypse
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
Kamal Menghrajani: The Limits of AI Healthcare
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 la
Why AI Makes Things Worse for Enterprise Teams
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
Andrew Marantz: What’s Wrong With Sam Altman?
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 indust
Breaking: Software Work Still Difficult
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 hig
Andrew Leland: Hacking Disability with AI
“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,
The AI Consulting Paradox
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
Hilary Mason: Product First, Then AI
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!) whi
New Words for a New Industry
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,
Evan Ratliff: Preparing for a Ridiculous Future
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 (an
Expertise Matters More Than Ever
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 ar
Erynn Petersen: Fixing Healthtech, One Bill at a Time
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 entire
Product Is More Than Prompts
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 PM
Gideon Lewis-Kraus: How Anthropic Sees Claude
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 met
Can Tech CEOs Be Thoughtful?
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 wishfu
Robot Reddit Wants Your Passwords
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 sug
Docs Heart Bots
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 whe
Yelling at Vibe Coders
“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
Are We All Developers Now?
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 a
Rafe Colburn: Building Etsy in the AI Era
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 Op
Totally Prepared for 2026
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—t
Dan Frommer: Consumers in the Age of AI
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
God, Sex, and AI
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 con
Max Read: Reporting on the Big, Bad Internet
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
(AI) Bubble Trouble
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 co
Arushi Saxena: Can We Trust AI?
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 a
Why the Software Industry Hates Your SMB
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 la
Bots Ate My Resume
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
Of Course There’s an AI Bubble
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 t
Welcome to Slopworld
AI videos from tools like OpenAI’s Sora and Meta’s Vibes are flooding our feeds. Is this the future? On the Aboard Podcast, Paul and Rich tackle a trio of AI topics. First: They look at a report from the Yale Budget Lab on which industries are adopting AI the fastest. (Spoiler: Only one is fully embracing it. Take a guess!) Then, they talk about spammy AI-generated bug reports submitted to the dev
NYC Sends AI Packing
All over the New York City subway, ads for the AI wearable “Friend” are being defaced. It seems clear that New Yorkers don’t want what Silicon Valley is selling—but will the general consumer bite? On this week’s Aboard Podcast, Paul and Rich assess the tensions between big tech and the public, in New York and beyond. After decades of having our data be packaged and sold, will anyone want to wear a
Tech’s Hard-Right Turn
The big tech CEOs are openly embracing Trump—so what do we all do now? On this week’s Aboard Podcast, Paul and Rich dig into Steven Levy’s recent cover story for WIRED’s politics issue that breaks down the industry’s hard pivot towards Trumpism. What did these leaders think they were signing up, and what are they actually getting? Plus: By way of metaphor, Rich offers up the world’s worst bundt ca
Bots, Feeds, and Kids
The Aboard Podcast is about software in the age of AI—but what non-AI things are happening in the world of software? Not much, Paul and Rich are sorry to report. In the first half of this week’s episode, they discuss how AI is sucking up all the tech oxygen in the room. Then, they pivot to talking about AI and kids: What should parents be teaching their kids about these tools? (Or should they even
The Billable Hour is Dead
Will AI put an end to management consulting? Maybe hold off on writing that McKinsey obituary for now. On the podcast, Paul and Rich break down the different kinds of consulting on a practical level, and assess what AI might mean for that work going forward. Can these companies really get away with charging the same rates if AI lets them reduce headcount or dramatically speed up the work?
Is Search Really the Future of AI?
Millions of people are using AI tools to search—so what does that mean for search engines? On this week’s podcast, Paul and Rich dive into (the questionably named) “GEO,” or Generative Engine Optimization. After an overview of Google’s classic model, they explore the ways AI is currently upending the search world, and speculate about what might emerge in the years to come. If LLMs cannibalize all
Matt Seitz: MBA…I?
How should the business leaders of the future think about AI? On this week’s podcast, Paul and Rich are joined by Matt Seitz, the Director of the AI Hub for Business at the University of Wisconsin’s School of Business. Matt discusses his journey from years at Google to his current role at UW, and he gives on-the-ground insight into the AI struggles of both leadership and employees in this moment o
AI Summer School #4: Chill Out About AGI
Aboard uses AI to help build software, but in just a few years, AI will gain sentience and take over our work, personal lives, and even brains—just kidding! Yes, the fourth and final installment of “AI Summer School” is about AGI, or “Artificial Generalized Intelligence.” What does it mean? Can anyone agree on a definition? And if no one can define it or agree on those definitions, what’s the like
AI Summer School #3: From Agents to Apps
So now that you’ve set up your AI agents, what can you build with them? In the third lesson of AI Summer School, Paul and Rich are joined by CTO Adam Pash to spin up a sample app in Aboard. How do agents work together to simulate the development process—and what’s the difference between Aboard’s structured approach and a vibe-coding tool? Plus: Introducing the Adam Pash Drinking Game, where you ta
AI Summer School #2: Call My Agents
“Agents” are a big marketing term for AI companies right now—but how do they actually work? In the second installment of AI Summer School, Paul and Rich are joined by Aboard Director of Engineering Kevin Barrett, who breaks down what “agent” actually means, and how they function within the platform. Plus: In the process of demoing Aboard’s agent capabilities, Paul becomes transfixed by the breedin
AI Summer School #1: How LLMs (Don’t) Think
Feel a little lost when it comes to AI? It’s time to go back to school—Aboard’s AI Summer School! Over the month of August, Paul, Rich, and a few special guests will break down the basics of LLMs, agents, AGI, and a host of other AI-related topics. In the first installment, they discuss how LLMs think—or rather, don’t think—and compare the major players on the AI scene right now.
Timing My Vibe Coding
Mapping the history of the universe—and the limits of current AI programming tools. On this week’s podcast, Paul walks Rich through his recent experiments trying to build timeline software via vibe coding. Spoiler: There were issues. Halfway through 2025, where do the current tools excel, and where do they fall flat? And looking over the few years at where these tools might be headed, what should
The View from the Lebanese Tech Scene
How do you build for the future amid ongoing instability? This week, Paul and Rich turn to Lebanon—literally, since that’s where Rich, who was born in the country and still has family there, is calling in from. After they discuss some Lebanese basics (Cedars! Small plates!) they turn to the Lebanese tech scene, discussing everything from investments in the Beirut Digital District to Aboard’s partn
Why We Made Aboard Human-First
AI is a great first step, but to really build software, you need humans to get the job done. On last week’s podcast, Paul and Rich talked about how Aboard works by focusing on those AI first steps; this week, they dig into the human work that gets Aboard projects over the line, from classic agency-style client management to the brand-new role of “Solution Engineer.”
Reintroducing Aboard
Paul and Rich are always talking about building software with AI—but how is Aboard actually building software with AI? This week’s podcast is a peek behind the curtain, walking through how Aboard gets you from a short prompt to real, working software in minutes. From the specific (the “Harvest Manager” app Paul creates for his pumpkin patch) to the broad (what this technology means for the softwar
A Blast From Computing Past
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?
Tech Giants Want AI to Behave
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?
Artificial Intelligence/Artificial Deadlines
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 Goes Shopping
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
AI Advice for the Confused CEO
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
Help Wanted: AI-First Companies Need Humans After All
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
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
Patrick Austin: AI’s Not There Yet
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,
A Database Will Never Love You
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
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 mo
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
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.
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
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?
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 high
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 everybo
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, us
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 s
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
Waiting for the DOGE Barbarians
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
AI as an Accelerant for Good
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
Don’t Freak About DeepSeek
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?
Brains Are Better Than Butlers
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.
Not Quite Finishing Apps
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
We Need More Software
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’
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