The Big Web Show

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The Big Web Show is a podcast hosted by Jeffrey Zeldman. Originally created at 5by5 Studios and co-hosted by 5by5 founder Dan Benjamin, the podcast moved to Mule Radio Syndicate on September 16, 2013 with Episode 96.[1] The Big Web Show features special guests and topics like web publishing, art direction, content strategy, typography, web technology, as well as current events.

The first show, on Web Fonts premiered on April 29, 2010 with guests Ethan Dunham and Jeffrey Veen. Notable guests include Jason Snell, Matt Mullenweg, Mike Essl, Jason Santa Maria and Marissa Christina.

The Big Web Show won several awards during its two years of production, including “Video podcast of the year” in 2010 [2] and “Podcast of the year” in 2011 from .net Awards.[3]


Title Summary Guests Show date
Web Fonts Jeffrey Zeldman and Dan Benjamin grill Ethan Dunham of Fontspring and Font Squirrel and Jeffrey Veen of Typekit (and other sites too numerous to name) about one of your favorite subjects, “real fonts on your website” in this, our inaugural episode. Ethan Dunham, Jeffrey Veen 2010-04-29
HTML5 with Jeremy Keith Dan and Jeffrey talk with Jeremy Keith, designer, writer, speaker, and author of HTML5 for Web Designers, a new book coming out in June 2010. They discuss the goals and inspiration behind the book, as well as what HTML5 means for both web creators and those who consume the web, covering topics that range from structure to accessibility and implementation. Jeremy Keith 2010-05-07
Re-invent Yourself Melissa Pierce’s film, Life in Perpetual Beta asks the question, “is the planned life worth living?” and sketches an answer via interviews with the likes of Baratunde Thurston, Irina Slutsky, and Biz Stone. Watch us turn the tables on the interviewer (now our interviewee) to find out how a homemaker with no filmmaking experience became the darling of the Chicago Independent Film Festival. Melissa Pierce 2010-05-17
Content Strategy Dan and Jeffrey talk in-depth about content strategy on the web with Kristina Halvorson, CEO, Brain Traffic and author, Content Strategy for the Web (New Riders, 2010), and Erin Kissane, content strategist with Happy Cog, and author of Erin Kissane and Kristina Halvorson 2010-05-20
Web Education Dan and Jeffrey talk with special guest Liz Danzico (@bobulate), author of Bobulate, columnist for Interactions Magazine, former editor of Boxes and Arrows, former director of experience strategy for AIGA, former IA director at Barnes & Noble, and chairperson of the MFA in Interaction Design program at New York’s School of Visual Arts. They discuss web and interaction design education, user experience design, how to structure a program and teach a class, acquiring and editing content, and much more. Liz Danzico 2010-05-28
Mobile First Dan and Jeffrey chat with leading interaction designer Luke Wroblewski about designing for the mobile space, and learn why the mobile experience for a web application or site should be designed before the PC version. Luke Wroblewski 2010-06-04
Usability Testing Dan and Jeffrey talk with special guest Jared Spool about usability testing in the real world, with practical advice for designers, UI engineers, and developers alike. Jared Spool 2010-06-11
User Experience Design Dan and Jeffrey talk with Whitney Hess about social networking, getting clients, and user experience design—from research to wireframes to testing and beyond. Whitney Hess 2010-06-17
Responsive Web Design Dan and Jeffrey talk with guest Ethan Marcotte. Topics include designing and coding for the likes of the Sundance Film Festival and New York Magazine, and the joys of responsive web design, working remotely, and more. Ethan Marcotte 2010-06-24
Less Is Always an Option Dan Benjamin and Jeffrey Zeldman talk with Jason Fried, CEO and co-founder of 37 Signals about changing an industry, collaborating, reducing distractions and interruptions, design, logos, usability, real and virtual offices, co-working, designing in the open, and more. Jason Fried 2010-07-01
Nicole Sullivan on CSS How do you scale CSS for millions of visitors or thousands of pages? Nicole Sullivan knows, and shares her insight, experience, and expertise in this in-depth discussion with Dan and Jeffrey. Nicole Sullivan 2010-07-08
Web Conferences Dan Benjamin and Jeffrey Zeldman talk with Andy McMillan, founder of Build, an annual “hand-crafted web design conference” located in Belfast, Northern Ireland, and CSS godfather Eric Meyer, co-founder of An Event Apart, the design conference for people who make websites. Eric Meyer and Andy McMillan 2010-07-15
Voices that Matter Jeffrey Zeldman and Dan Benjamin talk with Michael Nolan, a senior editor for Pearson’s New Riders Press and Peachpit imprints, focusing on web design and development. In this special hour of insights, we discuss how publishing really works, where it’s going, and how it will survive, plus plenty of stories about your favorite authors and designers, and tips on how to identify talent for those who are hiring, and how present yourself as a talented and desirable catch for those who are trying to boost their visibility and career prospects. Michael Nolan 2010-07-24
Design Apps for Fun and Profit Jeffrey and Dan talk with Gowalla CEO Josh Williams about social media, being an entrepreneur, developer applications for the web and mobile, marketing a new business, and more. Josh Williams 2010-07-29
Social Media, Social Capital Tara Hunt, social media entrepreneur, author of The Whuffie Factor, cofounder of Citizen Agency, and one of Fast Company’s “women in tech — nine thought leaders who are changing our ideas about technology” talks with Jeffrey Zeldman and Dan Benjamin about social media and much more. Tara Hunt 2010-08-05
Serious Doodles Jeffrey and Dan talk with Sunni Brown, noted information designer, about visual communication and debunk the myth that doodling is a distraction. Sunni Brown 2010-08-12
Web Meritocracy Jeffrey Zeldman and Dan Benamin talk with Tracy Osborn about the ins and outs of networking when you’re not well known; where ideas and inspiration come from; how to recognize and develop your best ideas and persuade others to believe in them; and more. Tracy Osborn 2010-08-26
Roger Black on Web Type and Templates Jeffrey and Dan talk with the legendary Roger Black about web type, design templates, screen resolution, web publishing, responsive design, and more. Roger Black 2010-09-02
Beyond Usability with Aarron Walter Jeffrey Zeldman and Dan Benjamin talk with Aarron Walter, lead user experience designer for MailChimp, about white-hat SEO strategies, user intent and content, usability, and more. Aarron Walter 2010-09-09
Creating Readability Jeffrey Zeldman and Dan Benjamin talk with Rich Ziade about how Arc90 manages the balance between product development and client services, and how to build a reputation when your client services agreements prevent you from having a public portfolio. Richard Ziade 2010-09-24
Just the Two of Us We’re mixing it up for today’s episode of The Big Web Show. Instead of interviewing one or more amazing web innovators per our standard practice, Dan Benjamin and Jeffrey Zeldman interview each other. N/A 2010-09-30
Dan Cederholm Dan Cederholm joins Jeffrey Zeldman and Dan Benjamin to discuss Dribbble, a vibrant design community for sharing screenshots of your work, Cork’d, the first social network for wine aficionados, his design style, inspiration, and more. A world-renowned web designer, author, speaker, and a giant in the field of CSS-based design, Dan is the founding principal of SimpleBits, a tiny creative studio (“We make websites and products”) based in Salem, Massachusetts. Dan Cederholm 2010-10-07
Paul Ford Paul Ford joins Jeffrey Zeldman and Dan Benjamin to discuss the web, the future of publishing, microsites, branding, community, and more. Paul Ford 2010-10-14
Todd Dominey Todd Dominey, creator of SlideShowPro, joins Jeffrey Zeldman and Dan Benjamin to discuss making the transition from indy designer to employee to business owner, his pioneering blog What Do I Know, Flash, HTML5, and more. Todd Dominey 2010-10-21
Karen McGrane Karen McGrane joins Jeffrey Zeldman and Dan Benjamin to discuss putting publications online, the state of content management, careers in web design, running a design business, teaching UX and design, and more. Karen McGrane 2010-10-28
Gary Vaynerchuk - Effort is Underrated Gary Vaynerchuk joins Jeffrey Zeldman and Dan Benjamin to talk about humanizing business, his upcoming book The Thank You Economy, success and guilt, his new radio show, and his biggest mistake. Gary Vaynerchuk 2010-11-04
Andy Clarke - It's Hardboiled Andy Clarke joins Jeffrey Zeldman and Dan Benjamin to talk about his new book, Hardboiled Web Design, the evolution of the web, and the right way to design with HTML5 and CSS3. Andy Clarke 2010-11-11
Finding Your People Jeffrey Zeldman and Dan Benjamin talk about what they’re thankful for, awards, visibility and public speaking (and why you should do it), Pub Standards, meetups (and why you should start or join one), and how to make a change. N/A 2010-11-25
Matt Mullenweg Matt Mullenweg joins Jeffrey Zeldman and Dan Benjamin to discuss the creation and evolution of WordPress, the growth of Automattic, making money with open source, and more. Matt Mullenweg 2010-12-02
Jason Santa Maria Jeffrey Zeldman and Dan Benjamin are joined by Jason Santa Maria and discuss mitigating the isolation of working in your underwear by reaching out to the community, avenues for creativity, struggling with the line between good enough and perfection, focus, why speaking and teaching are important, and why sometimes the distraction of working with other people is worth it. Jason Santa Maria 2010-12-09
Jim Coudal Jeffrey Zeldman and Dan Benjamin are joined by Jim Coudal to discuss the phenomenon that is Layer Tennis, his presentation “secrets,” and firing clients to work for yourself. Jim Coudal 2010-12-16
Mandy Brown Mandy Brown joins Jeffrey Zeldman and Dan Benjamin to discuss the value of support, the future of type on the web, font choice on reader platforms, what print publishers can learn from web publishers, why you’ve got to write, and why the future belongs to editors. Mandy Brown 2010-12-23
Dana Chisnell Dana Chisnell joins Jeffrey Zeldman and Dan Benjamin to talk about UX, testing, leveraging your expertise, New York City voting booth user experience design, and more. Dana Chisnell 2011-01-06
Craig Mod Craig Mod joins Jeffrey Zeldman and Dan Benjamin to discuss the decision to jump from freelance work to startup work, Craig’s experience traveling and writing the GF1 Fieldtest, how travel affects the work you do, and the multifaceted challenges and future of web publishing. Craig Mod 2011-01-13
Jen Simmons Jen Simmons joins Jeffrey Zeldman and Dan Benjamin to discuss Drupal, the Drupal community, content management systems, design, and the future of publishing. Jen Simmons 2011-01-20
Mike Essl Pities the Fool Jeffrey Zeldman and Dan Benjamin are joined by Mike Essl to discuss Mr. T, combining print and digital content, being Comic Book Guy in the age of eBooks, the past and future of proprietary platforms in publishing, and Mike’s fully wearable shirt empire. Mike Essl 2011-01-27
John Nack Jeffrey Zeldman and Dan Benjamin are joined by John Nack to discuss Photoshop and web design, crash reports, how pain points are opportunities, the Mac App Store, and the opportunity for mobile creative apps. John Nack 2011-02-03
Jason Snell Jeffrey Zeldman and Dan Benjamin are joined by Jason Snell of Macworld to discuss transitioning a print-focused publication into a web-focused publication, mixed models and “trying stuff,” ads and advertisers in multiple media, publishing a website, an App, and a Magazine, and why future of publishing means leaving things behind. Jason Snell 2011-02-10
Brian Alvey Jeffrey Zeldman and Dan Benjamin are joined by Brian Alvey to discuss the early days of the web, balancing products and services, taking big meetings, what’s coming next for Content Management Systems, being a small publisher, and moving toward bigger platforms. Brian Alvey 2011-02-17
Andy Rutledge Designer Andy Rutledge joins Jeffrey Zeldman and Dan Benjamin to discuss choosing clients, running a small company, and more. Andy Rutledge 2011-03-03
Best Web Show Jeffrey is en route to his appearance at SXSW Interactive this week, so we took this opportunity to dig into the Big Web Show archives to assemble a taste test of some of the best guests and topics. Enjoy! N/A 2011-03-10
Treesaver Jeffrey Zeldman and Dan Benjamin are joined by Filipe Fortes and Scott Kellum, the creators of Treesaver to talk a little about working on closed platforms at Microsoft, how working on a dynamic open publishing platform based on web technologies is a little like building a train while you’re riding it, weighing hand-crafted layouts and algorithmic layouts, and combating template explosion. N/A 2011-03-17
Krista Stevens Krista Stevens of Automattic joins Jeffrey Zeldman and Dan Benjamin to discuss great customer experiences and much more. Krista Stevens 2011-03-24
Sarah Parmenter Sarah Parmenter joins Dan and Jeffrey to discuss putting yourself online and living in public, creepy stalkers, being star struck, accents and idioms, distinguishing your work and brand through simplifying, her iOS Workshops, and sexism and discrimination in the web business. Sarah Parmenter 2011-04-07
Tim Murtaugh Dan Benjamin and Jeffrey Zeldman are joined by Tim Murtaugh to talk about design, and the fallacy of developing for the “mobile” platform. Tim Murtaugh 2011-04-14
Richard Rutter Dan Benjamin and Jeffrey Zeldman are joined by Richard Rutter, co-founder of Fontdeck and Clearleft, to discuss typography on the web and more. Richard Rutter 2011-04-21
Alexa Andrzejewski Alexa Andrzejewski joins Jeffrey Zeldman and Dan Benjamin to talk about Foodspotting and the path from user-centered design to the idea of seeing where Anthony Bourdain ate to a shipping product and the decision to take investment money on the way. Alexa Andrzejewski 2011-04-28
Pennies Shining Each Other Jeffrey Zeldman and Dan Benjamin discuss the state of the web, the evolution of Web Standards, the recent Boston AEA conference, and more. N/A 2011-05-05
Popularity Dan Benjamin and Jeffrey Zeldman discuss the intersection of community and popularity on the web and in terms of podcasts and social media. N/A 2011-05-27
Jen Robbins O’Reilly author, interviewer of rock stars, and longtime web and UX designer Jen Robbins joins Jeffrey Zeldman and Dan Benjamin to discuss the web of present and past, book writing, print design, method, style, process, and more. Jen Robbins 2011-06-02
At The Movies Dan and Jeffrey discuss speaking, offices, distributed working, movies, scorpions, New York, a new AEAlocation announcement, and more. N/A 2011-06-23
Greg Hoy Happy Cog president Greg Hoy joins Dan and Jeffrey to discuss business, design, and more. Greg Hoy 2011-06-30
Raising Rates Jeffrey Zeldman and Dan Benamin discuss the business of Web development. N/A 2011-07-07
Source Of All Knowledge Dan and Jeffrey talk about freelancing, project managers, setting up a new computer, and much more. N/A 2011-07-14
Marissa Christina Marissa Christina joins Jeffrey Zeldman and Dan Benjamin to discuss her path as a web designer diagnosed with a debilitating vestibular disorder, and her blog, documenting living with a hidden disability. Marissa Christina 2011-09-01
Faruk Ates Faruk Ates joins Jeffrey Zeldman and Dan Benjamin to discuss Modernizr, web and mobile design, Apple, and more. Faruk Ates 2011-09-08
Scott Jehl Scott Jehl joins Jeffrey Zeldman and Dan Benjamin to discuss the recent responsive resign of the Boston Globe, jQuery, the jQuery Mobile project, writing and speaking about web design, and his new book, Designing with Progressive Enhancement. Scott Jehl 2011-09-22
Double Release Jeffrey Zeldman and Dan Benjamin talk about lost offices, working from home, A Space Apart, A Book Apart’s new books: Designing for Emotion and Mobile First, future friendly, police sirens, Steve Buscemi, and more. N/A 2011-10-20
Mike Monteiro Jeffrey Zeldman talks with Mike Monteiro of Mule Design. Mike Monteiro 2011-12-02
Josh Williams Jeffrey speaks with Josh Williams, co-founder of Gowalla. Josh Williams 2011-12-19
Khoi Vinh Jeffrey Zeldman speaks with Mixel co-creator Khoi Vinh. Khoi Vinh 2011-12-21
Kristofer Layon Jeffrey Zeldman is joined by Kristofer Layon to discuss his book, Mobilizing Web Sites: Strategies for Mobile Web Implementation, and more. Kristofer Layon 2012-02-10
Michael Surtees Jeffrey Zeldman interviews Michael Surtees, founding partner and creative director at Gesture Theory, co-creator of Deckpub ("the future of publishing on iPad"), and author of Design notes. Michael Surtees 2012-02-17
Jenn Lukas Jeffrey Zeldman interviews front-end developer Jenn Lukas about how to tell if you're a designer or coder. Jenn Lukas 2012-02-24
Tim Brown Jeffrey Zeldman interviews Tim Brown of Typekit and Nice Web Type. Tim Brown 2012-03-02
David Sleight In Big Web Show Episode No. 66, Jeffrey Zeldman interviews veteran web designer and publishing creative director David Sleight. David Sleight 2012-03-08
Special Message for Big Web Show Video Subscribers Special Message for Big Web Show Video Subscribers Special Message for Big Web Show Video Subscribers 2012-04-02
Tantek Çelik Jeffrey Zeldman speaks with Tantek Çelik, web standards lead at Mozilla. Tantek Çelik 2012-04-26
Chris Cashdollar In Episode No. 69 of The Big Web Show, Happy Cog creative director Chris Cashdollar (@ccashdollar) and Jeffrey Zeldman (@zeldman) discuss the joys and challenges of redesigning typography mega-site, among other things. Chris Cashdollar 2012-05-03
Dan Benjamin Jeffrey Zeldman speaks with Dan Benjamin about his career and life journey leading up to the creation of 5by5. Dan Benjamin 2012-05-18
Richard Ziade In this episode, Jeffrey speaks with founding partner and CEO of Readability, Richard Ziade. Richard Ziade 2012-06-13


  1. ^ Just The Two Of Us: Monteiro & Me on Big Web Show No. 96
  2. ^ “Video podcast of the year” in the same awards show the previous year:
  3. ^ Podcast of the year 2011, .net Awards