New horizons in digital media: this week Paul and Rich talk to Anna Holmes, the founder of Jezebel and current SVP of Editorial at First Look Media, where she recently launched the visual storytelling site Topic.com. They discuss her early magazine career, the rise of online media, comment sections vs social media conversations, and what it's like to run a more reflective site in a world of reactive takes.
How does Postlight tackle security challenges? This week Paul and Rich begin the episode with takeaways from the Apple iPhone announcement (which they had not yet heard at the time of recording) before diving into a wide-ranging discussion on digital security, from personal worries to the Equifax breach to the steps they take as a company to ensure clients’ data safety. They then tell the story of the first $20 Postlight ever made—a tale about infidelity, large datasets, AshleyMadison.com, and a trio of guys who were definitely up to no good.
The challenges of product management at scale: this week Paul and Rich talk to Oren Mor, a head of product at Goldman Sachs and a former product manager at Google. They discuss his entry into the industry, making the technology behind Microsoft’s Kinect, his pivot to finance, and his return to tech at Google, where he spent years shipping ad products. They then go deep into the online advertising world, including ethical concerns around ad placements and the new taxonomies that’s creating on the web.
What makes a good meeting? This week Paul and Rich set out to break down everyone’s least-favorite part of the workday—the meeting—but they wind up breaking down complicated office management dynamics along the way. They do offer concrete tips and strategies, from how to keep your head down early in your career to keeping the agenda focused and specific to the beauty of ending a meeting early.
How design came to drive business: this week Paul and Rich talk about the evolution of the role of design in the tech industry, from Microsoft’s early dominance—privileging function over form—to Apple’s ascendency in the past decade, where user-centered design, particularly on mobile, has led to their success. Topics discussed include the McKinsey consultants, the early history of Apple, the jumble of titles and roles in the digital design world, and Rich’s perpetual hatred of Apple’s chief design officer, Jony Ive.
Understanding the fundamentals of public speaking: this week Paul and Rich talk to Bill Smartt, a coach who believes that everyone can improve their speaking skills. They break down his three big tips—speak up, slow down, and make eye contact—and discuss (and practice!) breathing exercises that can help when stagefright kicks in. They also discuss his origin story, which involves some poorly-placed dry ice at a Nashville Halloween party.
Remote working, iPhone cases, and Spotify’s UX: this week Paul and Rich tackle three very disparate reader questions. In the first, they outline Postlight’s remote working culture and the tools they use—most notably, Slack—to help everyone stay on the same page. Next, they talk about the iPhone as a design object—and our desire to immediately cover it up with a case. And finally, they go in on Spotify’s clunky user interface when asked: if Spotify was your client, how would you fix it?
Changing the podcast user experience: with Paul away, Rich is joined by Postlight’s new partner, Gina Trapani, for a conversation with developer Leah Culver. They discuss her career trajectory, from embracing computer science in college to moving Silicon Valley to founding startups Pownce and Convore to becoming an engineer at Dropbox. They then discuss her newest venture, Breaker, an “end-to-end podcast company,” and the podcast space in general, from the fractured digital spaces for podcast listeners to Apple’s recent announcement to share user data with creators.
Understanding an organization’s older technology systems: this week Paul and Rich discuss legacy software and the work cultures around them. Topics discussed include how companies put systems in place and how they become unworkable, resistance to change, clashes between engineering departments and broader company culture, and tips for dealing with the social dynamics when dealing with—and trying to change—legacy software and systems.
The history and the future of CSS: this week Paul and Rich talk to Eric Meyer, an expert on HTML and CSS for more than two decades, about web design and standards. Touching on both basic and more technical aspects of CSS, topics covered include the development of the style sheet language, the incompatibility of early web browsers, accessibility (or lack thereof) in modern web design, and, of course, what the W3C CSS working group’s after-parties are like.
The iPhone at 10: this week Paul and Rich reflect on the iPhone’s 10-year anniversary, discussing everything from Steve Jobs to Apple’s evolution to the future of smartphones to how Jony Ive uses a microwave. Then they debut a new segment where they complain about things that frustrate them; this week, they get out all their feelings about kombucha, the always-broken Google Inbox, and Adobe’s Creative Cloud.
Helping veterans enter the tech world: this week Paul and Rich talk to Jerome Hardaway, a veteran who became a programmer before founding Vets Who Code, a nonprofit that helps other veterans do the same. They discuss the challenges he faced reentering civilian life at the height of the Great Recession, how Vets Who Code was born, the specific assets vets bring to programming and the tech world, and how they overcome the challenges and stereotypes they face.
From Amazon to Russian watches: this week Paul and Rich start by trying to rationalize Amazon’s recent acquisition of Whole Foods, a conversation summed up by Paul as, “You can Occam's Razor this bad boy down.” They move on to Amazon’s strategy at large, the departure of Uber CEO Travis Kalanick, whether our individual actions can ever have any broader effect on the planet, and the harrowing saga of the time Rich tried to buy a watch from a shady Russian website.
Analog books in the digital age: this week Paul and Rich talk to Maris Kreizman, editorial director of Book of the Month Club, the 90-year-old book subscription service that shaped American literary history. Topics discussed include BOMC’s revival and current iteration, demographics and preferences in book consumption, materiality of paper books and physical bookshelves, Amazon’s relationship to the rest of the book world, and why Paul just can’t get behind mermaid fiction.
Chat, bots, privacy, and the internet of things: this week Paul and Rich embark on a wide-ranging conversation about innovation and change in tech—and its impact on our daily lives. Topics covered include connected devices, machine learning, the future of medical apps, technologies and superpowers, and whether it would be fun to go to a bar with Siri. (Spoiler: it wouldn’t.)
Understanding crowdfunding with “The Crowdsourceress”: this week Paul and Rich talk to Alex Daly, a Kickstarter expert whose company, Vann Alexandra, has managed 50 campaigns and raised more than $20 million dollars. They discuss her background and earliest introduction to crowdfunding, a number of memorable campaigns she’s run (for Neil Young, NASA, the MTA, and more), and tips and observations about building both an audience and a successful crowdfunding campaign.
Launching the employee development movement: this week Paul and Rich talk to Jen Dary, the founder of Plucky, “a consulting firm that helps companies with their people.” They discuss the value of retention over hiring, how to reframe thinking about career paths, Jen’s “employee development” approach to human resources challenges for both people and companies, and a pivotal conversation while stuck in traffic on the Verrazano Bridge.
A user’s experience in a world of endless updates: this week Paul and Rich talk about the changes tech giants and digital publishers make on our mobile apps and on the web. Topics covered include our apps’ constant stream of small updates, user-experience disconnect on major social media platforms, publications’ redesigns and the ultimate aims of publishing on the web, and the lack of—and the need for—software criticism.
Understanding advertising on the web: this week Paul and Rich talk to John Shankman, an internet advertising veteran who has worked at companies like Federated Media, Huffington Post, and The Awl Network. He currently runs Hashtag Labs, a company that helps make ad tech more manageable for independent publishers. The conversation runs through various types of advertising online, from programmatic to direct sales to premium networks, and tracks the life of a web ad for the Paul and Rich’s new school, “Ford University.”
From Uber to Mars to the New York City bus system: this week Paul and Rich talk about the highs and lows of tech industry’s relationship with transportation, where some apps dismantle industries and others knit cities together. The conversation includes Rich’s theories about tech billionaires and space travel, Paul’s paean to express busses and the MTA Bus Time API, and a segment in which Rich roleplays as Travis Kalanick—and Paul gets to tell the Uber CEO exactly how he feels.
Product management, from journalism to music to podcasts. This week Paul and Rich talk to Aaron Lammer about the three prongs of his career—as the co-founder of Longform, as a musician with Francis and the Lights, and as the host of Stoner, a new podcast about weed. They look at his career through the lens of product management and entrepreneurship—and Aaron’s tendency to downplay success, like going on tour with Chance the Rapper.
Digital innovation and collaboration: this week Paul and Rich sit down with Michael Shane, the Global Head of Digital Innovation for Bloomberg. They discuss his journey from professional clarinetist to applying for an editorial position on a whim to developing big and small ideas across platforms and divisions at Bloomberg. They then describe Bloomberg’s upcoming collaboration with Postlight Labs on a tool which integrates Bloomberg’s business context with news stories from any outlet.
Productivity at Postlight: this week, with Rich an ocean away, Paul is joined by Gina Trapani, a director of engineering at Postlight who is well-known for, amongst other things, founding the website Lifehacker. They discuss her productivity tool, TODO.txt, an open-source project now in the hands of Postlight’s team, and productivity tools at large, in a conversation ranging from the specifics of Paul’s favorite, org mode, to the way having children disrupts all your plans for organized, efficient workflows.
Geopolitical design thinking: this week Paul and Rich talk to Jeremy Pam, an international relations expert whose career has taken him from Wall Street to Iraq and Afghanistan to MIT to his current position at Columbia University’s Saltzman Institute of War and Peace Studies. The conversation ranges from sovereign debt relief to New York subcultures to working in a warzone to the Homebrew Computer Club, and they draw parallels between the tech world and geopolitics—and how to reconcile with outcomes your data models never predicted.