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.
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.
Paul and Rich discuss the evolving role of AI in software development, with Paul sharing his experience working on a data migration project using AI tools. They explore the idea that AI is becoming more 'boring,' meaning it's more comprehensible and integrated into existing workflows. They also debate the future potential and limitations of AI in creating fully automated solutions, emphasizing the continued importance of human expertise and iteration.
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 higher in the future, and building Korey, Shortcut’s forthcoming AI tool.
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 everybody’s favorite agrochemical conglomerate, Monsanto (well…not exactly).
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, using AI to better trade crypto, which leaves Rich uttering the phrase, “What’s the market cap of Fart...
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 state of the news. (Five minutes? Ten?)
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 then digs into the reasons why widespread student adoption of AI is worrying the faculty—and the st...
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 bureaucracy, is there an ethical way to swing the hammer? (Eh…)
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 examples of how AI is being used right now, from healthcare settings in India to the wildfires in Los A...
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 it close?
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’s venerable commercial waste-removal industry.
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 make predictions for what’s to come in 2025.
Executives are all-in on AI, but many workers are not: A recent survey of white-collar employees conducted by Slack shows workplace AI adoption has slowed, even stalled, in recent months. On this week’s Reqless, Paul and Rich explore the various reasons Slack’s respondents gave for their reticence and what they suggest about the current moment in tech. Is the issue the tools? Or is it how they’re being asked to use them—or if they’re being asked to use them at all.
This week the robots bring the pink slip…for Aboard’s CEO, Rich Ziade! On the latest episode of Reqless, Paul observes that much of Rich’s job at their old agency—listening to the client, reframing their needs, outlining a solution and a path to build it—could now be done, at least in part, by AI. What value can Rich—and other skilled software “translators”—bring to a project in a world of AI-accelerated development?
On this week’s Reqless, Paul and Rich receive a letter from a different Rich—a UX researcher interested in helping NGOs make the most of new AI tech. What should a UX researcher learn right now so they’re ready for what’s next? They discuss the things AI is particularly good at right now (translating artifacts!), and give concrete suggestions for things a UX researcher—or any technologist—can do to understand the breadth and scope of these tools.
AI is on the verge of utterly transforming the software industry, but how quickly will that change come? While Paul has been betting on a shorter timeline, Rich had thought the pace of institutional change would slow things down significantly. But on this week’s Reqless, Rich explains why his thinking has shifted—and how he’s coming around to Paul’s speedier timeline.
In the wake of the 2024 U.S. presidential election, Paul and Rich look towards the future with an AI lens—especially with the incoming Trump administration unlikely to put any regulatory guardrails on this rapidly evolving technology. What can AI do for people in our deeply fractured state? Are we doomed to poison the information environment forever, or could we use it to start building things that help people make sense of the world?
Non-profits often have tight budgets and specialized needs—and wind up having to pay a whole lot of money for consultants and imperfect, out-of-the-box software solutions. As generative AI promises to drastically reduce the cost of development, how will that affect the non-profit and NGO landscape? On this week’s Reqless, Paul and Rich assess this question, and offer up both immediate and longer-term advice for organizations struggling with software right now.
The Biden administration recently put out their first-ever National Security Memorandum on Artificial Intelligence, so on this week’s Reqless, Paul and Rich unpack the memo and discuss what it might mean for the U.S. government’s future attitudes towards AI. Plus: They talk about recent developments with Anthropic’s Claude that allow you to control all the computers in the world.
How has public perception of AI changed over the past two years? On this week’s Reqless, Paul and Rich welcome on writer and editor Josh Tyrangiel, who’s been the Washington Post ’s “AI tourist” columnist since early 2023. They discuss what he’s encountered in various industries experimenting with AI, and the overall sentiments he’s observed as ordinary people grapple with this technology. Plus: He discusses his recent collaboration with Oprah Winfrey on an AI special for ABC News—and the remark...
Reqless tends to take a measured yet optimistic stance on AI, but a lot of people out there hate it—for reasons including the environmental impact, the dubious origins of LLM training data, and, of course, the looming threat of AGI, A.K.A. our future robot overlords. On this week’s episode, Paul and Rich discuss some of those critiques, as well as zoom out to look at the longer arc of the technology industry and its impact on the world, asking the question, “In five years, is the world in a bett...
You’re a business stakeholder trying to evaluate AI tools for your organization. How should you assess them—and how should you measure the value of their outputs? On this week’s Reqless, Paul pitches Rich an acronym for this very task: TRACE. Transparent, Repeatable, Actionable, Clear, Efficient. How can these metrics help someone understand these tools before letting them into their org, and help them calculate the potential return on investment? Plus: Paul and Rich discuss a rec...
These days, it can take longer to plan the software launch party than to spin up the software itself—which is exactly what happened with Aboard Climate, a new integration Paul, Rich, and the Aboard team debuted last week. Hangovers nursed and moderately rested, Paul and Rich discuss the event and the feature itself—which lets you incorporate real-time data from the climate-change literacy organization Probable Futures directly in Aboard—before talking about how the building process reflects toda...
Does AI mean the end of software development jobs—or is this the start of a brand-new boom? Tech industry narratives are painting a gloomy future for coders, but on this week’s Reqless, Paul and Rich take the opposite tack. AI will shift who has access to software creation and the way things get built—so how should technologists position themselves for the coming decade?
Is the SaaS era coming to an end? On this week’s Reqless, Paul and Rich discuss recent comments from Klarna CEO Sebastian Siemiatkowski, who says that generative AI has allowed them to build internal tools that let them dispose of products like Salesforce and Workday. With the cost of building software on the brink of dropping precipitously, what does that mean for the SaaS giants going forward?
If AI is about to fundamentally change software development, what should current students be learning about code? On this week’s Reqless, Paul anoints Rich as head of a fictional programming department and asks him to lay out his syllabus—before hijacking the exercise and laying out his own syllabus. You need just enough knowledge to really use these tools to program, so what exactly should students learn?
