Shows
Undigital PodcastAirbnb CEO Brian Chesky on 'Founder Mode'In this episode, Airbnb CEO Brian Chesky discusses the company’s latest innovations, including the introduction of the co-hosting network and new guest experience updates. He reflects on the impact of “Airbnb Categories” and how the platform is evolving to provide more personalized travel experiences. Chesky also shares his leadership philosophy, emphasizing the importance of staying present in the details and redefining micromanagement as a form of partnership rather than control. He offers insights into “Founder Mode,” explaining why great leaders should balance trust and involvement to effectively guide their teams. Chesky’s vision for Airbnb’s future is one of continu...
2024-10-1635 minUndigital PodcastFeel Good Productivity with Ali AbdaalMedical Doctor-turned-YouTuber, Ali Abdaal, joins me to talk about his new book Feel Good Productivity: How to Do More of What Matters to You Find Ali: youtube.com/aliabdaal Find Ali's book: feelgoodproductivity.com Get it on Amazon
2023-12-2641 minUndigital PodcastInterview with SurveyMonkey CEO Eric JohnsonEric Johnson joins me for a conversation about how SurveyMonkey is getting back to its roots and rethinking the way it serves its customers. We also talked about the company's newest product, as well as why AI isn't just a marketing term if you are thoughtful and intentional about using it to add value to users. Thoughts from Our CEO (SurveyMonkey Blog)
2023-10-0530 min
Undigital PodcastInterview with Superhuman CEO Rahul VohraJason and Rahul talk about the problem of email, as well as how Superhuman says it saves its users as much as 3 hours a day. Plus, they walk through the brand new release of Superhuman on Android. Superhuman in the iOS App Store Superhuman in the Google Play Store Superhuman launches on Android
2023-07-2939 minUndigital PodcastAn Interview with Notion's CEO Ivan ZhaoNotion is launching its AI features to the public, and Jason has questions. What does it mean for how we work? What about my data--will it be used to train language models? In this conversation, Jason talks with Notion's CEO, Ivan Zhao, about what the new AI features mean, and how they might just fundamentally change the way we work.
2023-02-2226 minUndigital Podcast"I Like Sound" (The New HomePod Reviews)Jason is joined by guest Stephen Robles to talk about movies, drinking water, and podcasts. Mostly, we talk all about the brand new (but also very much the same) 2nd-generation HomePod. Stephen did an in-depth review of how it compares to various other (more expensive) sound setups and we talk about why Apple brought it back after discontinuing the OG HomePod in 2021. Jason's HomePod Review Movies on the Side Episode 168: Dune Stephen's Review on YouTube Stephen on Twitter: @stephenrobles Follow us on Twitter: @jasonaten @undigitalfm
2023-02-091h 02Undigital PodcastChatGPT: The Robots are Having a MomentJason and Jess talk about ChatGPT, the ai-text generator that has more than a million users. Microsoft recently announced it was investing $10 billion in OpenAI, the creator of ChatGPT. What does that mean for Microsoft? How about Google Search? We talk about it all--including the controversy around CNET, a tech publication that was using AI-generated text to publish articles. ChatGPT + Microsoft CNET Controversy What does it mean for information on the internet? https://www.cbsnews.com/news/chatgpt-chat-ai-jobs-most-likely-to-be-replaced/ Will ChatGPT make people use Bing?
2023-02-0252 minUndigital PodcastEverything Is a Mess (Twitter Edition)Jason and Jess have thoughts about the Twitter mess, because of course everyone has thoughts now that the richest man on earth is messing with, well, everything. More importantly, however, we try to settle once-and-for-all whether you should be using Safari or Chrome (or something else like Brave). Is Safari good enough to use on a regular basis? Is Chrome really stealing all of your personal information? Those are important questions and we're going to try to answer them. Finally, Jess got a new toy for her office, and Jason got a new office--literally.
2022-11-1058 minUndigital PodcastiPhone Home ScreensJason and Jess reveal what's on their iPhone home screens and lock screens. We also talk about why we include certain apps and widgets and cover some best practices for keeping all the apps on your iPhone organized. **Sorry for the delay in publishing due to Jason's Portuguese travel adventure** Links from this episode: Making the most of Lock Screens and Home Screens Jason's Interview with David Smith of Widgetsmith Organizing the apps on your Home Screen (Inc.com) Jess' Home Screen + Lock Screen Jason's Hom...
2022-11-071h 00Undigital PodcastSo Many iPadsJason and Jess talk about Apple's newest iPads, as well as what an iPad is even for. Should you buy one? If so, which is the best one based on your needs? We get into it and even talk about a couple of the best non-iPad tablets available. Links from the show: Level Lock+ Jason talked about the new iPads on the AppleInsider Podcast Jason's Review of the new iPads (Inc.com) The Mighty iPad Mini If you really want to know about Stage Manager on the i...
2022-10-2850 minUndigital PodcastA Very Smart HomeJason and Jess talk about their smart home setups and whether Google, Amazon, or Apple have the best smart home ecosystems. We also cover our favorite smart devices, and what you should know about Matter. Off topic, we discuss the best travel apps, and Jess has a gadget that she's very excited about. Links from the episode: Alexa vs Google Assistant vs Siri What's the Matter? (via MacRumors) Google's smart home product page Amazon's smart home product page Flighty Jess' favorite "gadget" Find us on T...
2022-10-211h 00Undigital Podcast036 - There's So Much ChangeIn this reboot episode, we talk about what has changed over the past year, and what is changing moving forward. That includes a brand new name for the Podcast starting next week (you don't have to do anything, it'll just appear here as usual). Starting next week, the show will be called UnDigital and it will continue to appear right here, with a focus on having practical conversations about tech and what actually matters to your life. We also talk about when and why people should start thinking about updating their smartphone, and whether the iPhone 14 is...
2022-10-1357 minUndigital Podcast035 - An Interview with Airbnb CEO Brian CheskyJason talks to Airbnb CEO Brian Chesky about why hybrid work doesn't work, how the company made it through a pandemic when no one was traveling, and how he's thinking about the future of work. Chesky also gives an overview of what he says is Airbnb's biggest change yet, making it far easier to find your next travel destination.
2022-05-1125 minUndigital Podcast034 - We're Not MissingJason and Jess are returning with new episodes every other week, starting March 2nd.
2022-02-2401 minUndigital Podcast033 - Interview With Evernote's CEO Ian SmallJason talked with Evernote's CEO, Ian Small about how the company is reinventing its app by going back to its roots. Anyone who has used productivity software is likely familiar with Evernote. Over the past few years, however, many people moved on as it seemed like Evernote "lost its way." After rebuilding the entire thing from the ground up, the company is adding features like task management and calendar integrations in the hopes that it might again become "an extension of your brain." Jason and Ian talked about how Evernote got here, where the company an...
2021-07-2139 minUndigital Podcast030 - Who would do that?Jason and Jess talk through Apple's recent announcements, including the purple iPhone, AppleCard Family, the new iPad Pro, and the colorful new iMac. They also touched on the controversy at Basecamp, including the problem with taking sides. That's a lot for one episode, but I think we made it through.
2021-04-3045 minUndigital Podcast029 - Interview with Slack's Chief Product Officer, Tamar YehoshuaJason talks with Tamar Yehoshua, who is the head of product for Slack. Everyone knows what Slack is, especially if you work remotely. In this conversation, Jason and Tamar talk about how Slack handled its own shift to being fully remote this past year, as well as how it has adapted to help its customers do the same. Plus, Tamar shares a few super helpful power-user tips for using Slack to be productive. One of those ways is Slack Connect DMs, allowing you to DM anyone, even if they're outside of your organization. S...
2021-03-2422 minUndigital Podcast028 - Interview with Donald MillerJason interviewed author and Entrepreneur Donald Miller about his new book, Business Made Simple, as well as what it was like to completely transition his company and team of 40 to working remotely. Also, be sure to check out my review of the book for Inc.com (Apologies for the Zoom-meeting quality audio) You can find Donald Miller on Instagram, or check out the book on Amazon.
2021-03-2319 minUndigital Podcast026 - What Comes NextJason and Jess get caught up after taking a week off. They also talk about what comes next--you know, after the world gets back to "normal," whatever that means. Specifically, what will working remotely look like when people start heading back to the office. https://www.computerworld.com/article/3599140/the-work-from-home-employee-s-bill-of-rights.html https://www.businessinsider.com/lifestyle-overhauls-take-full-advantage-remote-work-2021-2 https://www.usatoday.com/story/money/2021/01/05/jobs-home-29-professionals-would-quit-if-forced-go-back-office/4142830001/ https://www.forbes.com/sites/maurathomas/2021/02/03/more-ways-to-succeed-at-remote-work-in-2021-and-beyond/
2021-02-1236 minUndigital Podcast025 - Show Your WorkYes, we skipped last week. Life happens. To make up for it, this week, we've got a piece of Jason's interview with David Smith, the developer behind Widgetsmith, which was the top free app in the iOS App Store for weeks last year. You'll have to forgive the audio difference, we recorded the interview for a piece I wrote, but there some great stuff and David was kind enough to give permission to use it in this episode. That said, we didn't record it with all the high tech gear you'd normally use for a podcast. ...
2021-01-2849 minUndigital Podcast022 - It's Finally overJason and Jess talk about the holidays, along with a few of their favorite gifts this year. Then, looking ahead, they get into some of the tools and tips that can help everyone start 2021 productively. Graeter’s Ice Cream Skyline Chili Ember Mug Grovemade Desk Pad AeroPress Fantastical Things Trello Basecamp Notion Episode 008 - Interview with Shawn Blanc The Best iPhone app is Siri + Reminders AppleInsider Year-in-Review Episode Jason on Twitter...
2020-12-311h 11Undigital Podcast021 - Looking Back and ForwardJason and Jess talk about the things they learned this year, especially about working remotely, as well as personally. Maybe more important, they talk about what they look forward to in the coming year. There's also plenty of conversation about Christmas cookies, because, well, decorating Christmas cookies on Zoom is the most 2020 thing we can think of. Also, Jason talks a bit about his experience using the AirPods Max. Jason's Christmas cookies Jason on Twitter Jess on Twitter
2020-12-1750 minUndigital Podcast020 - Best Tips for Working From HomeYeah, it's episode 20 of 2020! Jason and Jess talk about tips for being productive and avoiding burnout while working from home, especially considering a lot of people are going to be doing just that for a while. Of course, they also had to talk about how much Jess likes her new MacBook Air, and the recent announcement of Apple’s AirPods Max, which are $550 headphones. Does anyone need $550 headphones? Anker 8 in 2 USB-C Hub Tips for Working Remotely Light therapy lamp HappyFeed app Facebook Is Getting Sued by the FT...
2020-12-1057 minUndigital Podcast019 - You're Doing It All WrongMostly, Jason and Jess talk about how we're all doing pretty much everything wrong. Sure, we made it through Thanksgiving, but it was a lot different than in the past. That includes shopping for gifts on Black Friday/Cyber Monday, but doesn't stop there. We also talked about Salesforce buying Slack and what that means for people working remotely. Oh, and Microsoft introduced a "tool" that was really a way to monitor what their teams are doing. It's creepy and we talked about what it means, as well as Microsoft's updated response to the pushback. Fi...
2020-12-0356 minUndigital Podcast018 - A New Holiday TraditionHappy Thanksgiving. Jason and Jess talk a little about her new M1 MacBook Air, but mostly about the things we're looking forward to about the holidays. Of course, that includes our favorite traditions and Christmas movies. No, it's not too early for Christmas movies. For that matter, Jason already has two Christmas trees up already. Jason's M1 MacBook Air Review iOS apps on the Mac are, well, bad. Thoughts about the HomePod mini Comcast is about to make it more expensive to work from home. Salesforce is buying Slack...
2020-11-2656 minUndigital Podcast017 - It's SuperFasterBetterJason and Jess talk about Apple's new HomePod mini, as well as the new M1 Macs, whether they're worth it, and who should consider buying one. I Flew Delta During the Pandemic. It Wasn't Scary at All. M1 Mac Benchmarks MacBook Air Configuration Thoughts about using the MacBook Air MacBook Air Battery Life Thread
2020-11-2047 minUndigital Podcast016 - The M1 Macs Are RidiculousJason and Jess talk about Apple's Event announcing the new M1 Macs, especially the MacBook Air. More importantly, they talk about why they actually matter. Things also get deep as they talk about the importance of having a job that fits the type of life you really want to live. Apple's M1 Mac Event "One More Thing" Apple's New MacBook Air Is Really Just Showing Off Tell us what you think on Twitter Jason Jess
2020-11-1347 minUndigital Podcast015 - You can't pay the bills with a bylineThere’s a lot going on this week as we continue to wait to find out the results of the election. So, we’re going to talk about other stuff. Like, for example, why the gig economy is going to be so important in the future, and why Proposition 22 is a good thing. Jason and Jess also talk about their own experience freelancing, and describe some practical steps you can use to get started. We also talk about Apple’s announcement that it’s holding an event next week to launch new laptops powered by Apple Silicon. We’ve kno...
2020-11-061h 01Undigital Podcast014 - Exactly What 2020 NeededTechnical difficulties meant that this episode is late, which just means you're going to get to listen to us twice this week! Also, Jess had a birthday, and we're not asking how old she is. And Jason was in New York to see a car. It was a very nice car. On to the show notes. Jason and Jess talk about the iPhone 12, and whether or not it's worth it for the cameras and the 5G (definitely not the latter). They also talk about why Ted Lasso is such a hit, as well...
2020-11-031h 02
Undigital Podcast013 - Interview with Jeff and Erin YoungrenJason interviews Jeff and Erin Youngren, photographers and entrepreneurs in San Diego, CA. The Youngrens run a large photography business that includes weddings, commercial photography, and corporate events. In their conversation, they talk about what it's been like managing a team during the pandemic, at a time when in-person events aren't a thing. They also go in-depth describe how they manage their time and get things done while running a business and raising a family. One of the highlights is the way the Youngrens and their team use time blocking to be more intentional and effective at...
2020-10-2650 minUndigital Podcast012 - Say Goodbye to Quibi and Hello to the Best Thing on StreamingJason and Jess talk about the recent iPhone 12/12 Pro review, and why it might be worth upgrading for the cameras alone if your current device is more than a few years old. They also talk streaming services, including the news that Quibi announced it was shutting down. On the other hand, Ted Lasso is not shutting down and is currently the best thing in streaming. It wasn't difficult, but Jason manages to get Jess completely hooked. You should definitely watch it too. On a more practical note, they discuss how to manage time and actually...
2020-10-2252 min
Undigital Podcast011 - Interview with Michael McFall, Co-CEO of Biggby CoffeeJason interviews Michael McFall, the Co-CEO of the third-largest coffee franchise in the U.S., Biggby Coffee. In addition to talking about what it's like leading a company with hundreds of franchisees, Jason and Michael talk about how Biggby has adapted and met the challenges of the last 8 months. In addition, they talk about what it means to help your team develop a life they love, both inside and outside of work. Michael's book, Grind, has some great insight for any entrepreneur, and Jason asks about how leaders can continue to help their teams expect and pursue p...
2020-10-1931 minUndigital Podcast010 - Grab Some Snacks, The iPhone 12 Is HereWell, we made it ten episodes. Jason and Jess talk about the iPhone Event, and all four of the new iPhone 12 models. First, however, there are important things to cover like whether the “holiday” shaped Resse’s are better than the standard “cups.” (They are.) They also talk about the HomePod Mini, why it's so important to Apple, and whether anyone is going to actually buy a $99 smart speaker when you can get an Echo Dot for $19. Twitter conversation about Reese’s and M&M’s These Strawberry Nut M&Ms are garbage (referred to as...
2020-10-151h 09
Undigital Podcast009 - Interview with Aaron Levie, CEO of BoxJason talks with Aaron Levie, the co-founder and CEO of Box. In addition to some honest conversation about how coping with a pandemic is just hard, they talk about how companies can thrive even in disruptive--and difficult--circumstances. The conversation includes how Box is helping its team deal with working remotely, and what the company is doing to continue taking care of its customers at a time when they need it the most. Finally, Aaron shares some great insights into what other entrepreneurs should be doing right now to take care of their people, their customers, and their c...
2020-10-1226 min
Undigital Podcast008 - The Best Coffee In Northwest Arkansas + Special Guest Shawn Blanc from The Sweet SetupJess and Jason talk about the most important thing about working remotely--how to make the perfect cup of coffee. We also talked about how technology can both help us be more productivity, but all that productivity is starting to lead to burnout for a lot of people. Plus, Jason talks with Shawn Blanc from The Sweet Setup about how he researches and figures out the best apps and tools for staying focused and productive. Shawn also talks about combating "dual focus," and why it matters. It was a great conversation and Shawn has a ton of really he...
2020-10-081h 33
Undigital Podcast007 - Interview with Andy Puddicombe, Co-Founder of HeadspaceIn this special interview episode, Jason talks with Andy Puddicombe, who is the co-founder of Headspace. They talk about Headspace and its unique partnership with Microsoft, as well as how we can all use mindfulness to fight against the burnout and distraction that comes with trying to be productive in this very challenging time. Be sure to check out The Headspace app
2020-10-0523 min
Undigital Podcast006 - The Remote Life of a Corporate YouTuberWe gave Jess the week off (don't worry, she'll be back next week!) so Jason interviewed Andy Owen, who is a video producer and corporate YouTuber (it's a thing, really) for TechSmith. You may be familiar with a few of TechSmith's products like Camtasia and Snagit, and if you are, Andy's a part of the reason why. We talk about what it's like going from working for yourself (remotely) to working in an office, and back to working remotely. That includes setting up your space, managing your time, and a few of the tools you can use t...
2020-10-0133 min
Undigital Podcast005 - Interview: Stephen Robles, AppleInsider Podcast HostJason talks with AppleInsider Podcast co-host, Stephen Robles about the latest Apple gadgets, including the new iPad Air and whether it's a worthy replacement for your laptop or desktop. Also, what does the iPad Air mean for the future of the iPad Pro. We also had some conversation about the Apple Watch. We actually recorded this just after Stephen received his Series 6, and before Jason received his so this episode exists in a bit of a time warp. Be sure to listen to Stephen’s review of the Series 6 on the AppleInsider Podcast. You can fin...
2020-09-2842 min
Undigital Podcast003. All About ScreensJason and Jess talk about some of the latest efforts by tech companies to make gadgets that are supposed to make us more productive. They also ponder whether anyone really needs a dual screen device like the Microsoft Surface Duo, or a foldable like the Samsung Z Fold 2. Oh, and of course, there’s some follow up on the Apple Watch Series 6, since we apparently can’t have an episode without talking about the Apple Watch. We wrap up the conversation talking about iOS 14, some of its best productivity features—especially widgets. Mostly we can’t decide if they’...
2020-09-2457 min
Undigital PodcastInterview with Brian Halligan from HubSpotIn this special interview episode, Jason talks with HubSpot's CEO and Co-Founder, Brian Halligan about how working remotely has affected HubSpot's team as they launch a new product, and stage a major virtual conference. Inbound is one of the most popular marketing events, drawing more than 25,000 people last year to Boston. This year, the event is taking place entirely online, and Jason and Brian talk about what it was like to pull off such a large-scale event, how work is different right now, and what it might look like when we get past the pandemic.
2020-09-2222 min
Undigital Podcast002 - Is the Series 6 Worth It?Jason and Jess talk about the September Apple Event, and whether the Series 6 is worth the upgrade. Jess talks about whether or not she has buyer’s remorse, or if she’ll just give that rose gold Series 3 to her son. There’s also conversation about the new iPad Air, and whether an iPad can replace your laptop if you’re working remotely. Plus, as a bonus, we cover some of our favorite productivity apps and how we use them to stay organized, but mostly Jess’ interesting choice of folder names on her iPhone home screen. Also, Jess has w...
2020-09-1758 min
Undigital Podcast001-Apple Watch InsanityIn light of the news that we're likely to see a new Apple Watch next week, Jason and Jess talk about buying a new Apple watch--well, four actually. Plus, we talk about why the Apple Watch is such a great productivity tool for working from home. We also talk about why everyone who works from home needs a door, or--at a minimum--a good pair of headphones. A few of the things mentioned in the episode: These 3 Features Make the Apple Watch a Remote Worker's Best Friend Apple Watches on Woot (not a s...
2020-09-1038 min