Catalyst

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.

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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.

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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.

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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.

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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.

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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.

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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?

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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.

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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.

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