Undigital Podcast

Airbnb CEO Brian Chesky on 'Founder Mode' Oct 16, 2024

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 continuous innovation and deeper engagement with both hosts and guests.

Airbnb's Winter Release
My previous interview with Brian

Feel Good Productivity with Ali Abdaal Dec 26, 2023

Medical 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

Interview with SurveyMonkey CEO Eric Johnson Oct 05, 2023

Eric 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)

Interview with Superhuman CEO Rahul Vohra Jul 29, 2023

Jason 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

An Interview with Notion's CEO Ivan Zhao Feb 22, 2023

Notion 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.

"I Like Sound" (The New HomePod Reviews) Feb 09, 2023

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

Get the Undigital Newsletter

ChatGPT: The Robots are Having a Moment Feb 02, 2023

Jason 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?

Everything Is a Mess (Twitter Edition) Nov 10, 2022

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.

iPhone Home Screens Nov 07, 2022

Jason 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 Home Screens

So Many iPads Oct 28, 2022

Jason 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 iPad

The Google Pixel Tablet Find Jason on Twitter: @jasonaten

Find Jess on Twitter: @pingitup

Send us a message on Twitter: @undigitalfm

A Very Smart Home Oct 21, 2022

Jason 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 Twitter:

@undigitalfm

@jasonaten

@pingitup

036 - There's So Much Change Oct 13, 2022

In 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 worth it. Then, we chat about the new Apple Watch Ultra and Series 8. Finally, we explore why the best snack foods only exist in other places. Links from this episode:

This is the iPhone 14 you should buy

It's all big phones from here on out.

The Apple Watch Ultra's orange button

The Verge Amazon Event Liveblog

Salted Carmel Popcorn KitKat New York Style Cheeseburger Pringles

035 - An Interview with Airbnb CEO Brian Chesky May 11, 2022

Jason 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.

034 - We're Not Missing Feb 24, 2022

Jason and Jess are returning with new episodes every other week, starting March 2nd.

033 - Interview With Evernote's CEO Ian Small Jul 21, 2021

Jason 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 and app are headed next, and why the whole thing just might work.

030 - Who would do that? Apr 30, 2021

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.

029 - Interview with Slack's Chief Product Officer, Tamar Yehoshua Mar 24, 2021

Jason 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.

Slack Connect

About Tamar

028 - Interview with Donald Miller Mar 22, 2021

Jason 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.

026 - What Comes Next Feb 12, 2021

Jason 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/

025 - Show Your Work Jan 28, 2021

Yes, 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.

Widgetsmith

Pedometer++

David Smith

With More Than 50 Million Downloads, Widgetsmith Became an Overnight Success 12 Years in the Making

To be more productive in the morning, do these 2 things at night.

Jason on Twitter

Jess on Twitter

022 - It's Finally over Dec 31, 2020

Jason 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.

Episode 008 - Interview with Shawn Blanc

The Best iPhone app is Siri + Reminders

AppleInsider Year-in-Review Episode

Jason on Twitter

Jess on Twitter

021 - Looking Back and Forward Dec 17, 2020

Jason 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

020 - Best Tips for Working From Home Dec 10, 2020

Yeah, 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 FTC and a lot of states.

019 - You're Doing It All Wrong Dec 03, 2020

Mostly, 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.

Finally, we talked about how most people aren't willing to put in the extra effort when it comes to sending messages on LinkedIn. I think we agree it's a useful tool, especially for freelancers or people looking for work, but only if you do it right--which most people aren't.

Best Gadgets Gifts for techies.

Microsoft's Productivity Score is Creepy

Fortunately, they made some changes

Salesforce Spent $27.7 Billion on Slack.

Honestly, that's a steal for Salesforce.

Stop doing this on LinkedIn - it's hurting your brand.

018 - A New Holiday Tradition Nov 26, 2020

Happy 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, maybe.

017 - It's SuperFasterBetter Nov 20, 2020

Jason 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

016 - The M1 Macs Are Ridiculous Nov 13, 2020

Jason 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

015 - You can't pay the bills with a byline Nov 06, 2020

There’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 known these were coming, but now we get to see if Apple can actually pull off what we all expect - a fast, lightweight, powerful laptop with all-day battery life. We’ll know soon.

Uber’s win over California is a big win for the gig economy.

MuckRack

10 Best iOS 14 Apps for the iPhone 12

Apple Event “One more thing.”

014 - Exactly What 2020 Needed Nov 03, 2020

Technical 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 as favorite TV shows in general. It's official, Ted Lasso is exactly what 2020 (and Apple TV+) needed.

On more substantive topics they talk about the best iPhone apps for staying organized and getting stuff done and how to improve workplace culture when you can't all be together.

013 - Interview with Jeff and Erin Youngren Oct 26, 2020

Jason 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 how they prioritize work and fit everything into a very busy life.

Creative Rising Podcast (be sure to listen to episode 401)

The Youngrens on Instagram

The Youngrens (website)

Asana

Jeff's Egg Timer

012 - Say Goodbye to Quibi and Hello to the Best Thing on Streaming Oct 22, 2020

Jason 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 get things done when you don't work in an office and have someone looking over your shoulder all the time.

Which iPhone 12 you should buy.

Quibi didn't fail because of the pandemic. (It was just bad)

Ted Lasso is the best thing on streaming.

011 - Interview with Michael McFall, Co-CEO of Biggby Coffee Oct 19, 2020

Jason 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 perfection, even though everything else seems like chaos.

Biggby Coffee

Grind (Michael's book)

Life You Love Laboratory

Michael McFall on LinkedIn

010 - Grab Some Snacks, The iPhone 12 Is Here Oct 15, 2020

Well, 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 PB&J during the episode)

Send us your tweets about your favorite snack

Jason on twitter (@jasonaten)

Jess on twitter (@pingitup)

Nature Valley Bag of Granola (Cinnamon)

Apple Event Keynote on YouTube

HomePod Mini at Apple.com

Jason's take on the HomePod Mini

iPhone 12 at Apple.com

The iPhone 12 is Getting MagSafe

Why 5G Isn’t Really a Thing Yet

Nomad Base Station Pro

Totallee Case

Send us your thoughts on twitter or to podcast@29steps.fm about whether or not you should be putting ice in your coffee, or even worse, your wine.

009 - Interview with Aaron Levie, CEO of Box Oct 12, 2020

Jason 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 community.

Aaron on Twitter

008 - The Best Coffee In Northwest Arkansas + Special Guest Shawn Blanc from The Sweet Setup Oct 08, 2020

Jess 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 helpful insight into how to get the most out of the technology we use to stay organized and get work done.

Shawn Blanc on Twitter

The Sweet Setup

Onyx Coffee, the best coffee in Northwest Arkansas (according to Jess)

Snappy

Ember Coffee Mug at the Apple Store

Contigo Travel Coffee Mug

Bodum French Press

Microsoft is trying to bring back the virtual commute

Jason’s interview with Headspace co-founder Andy Puddicombe

G Suite is now Google Workspace

(A few other great email options that Jason recommends)

Brave Browser

Apple’s Refurbish Store

Will Apple Silicon mean the perfect laptop for remote working?

007 - Interview with Andy Puddicombe, Co-Founder of Headspace Oct 05, 2020

In 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

006 - The Remote Life of a Corporate YouTuber Oct 01, 2020

We 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 to stay productive.

Be sure to check out Andy's insightful LinkedIn posts by visiting his profile.

Andy also mentioned the Self Control app

Camtasia (TechSmith's video editor)

TechSmith YouTube channel

005 - Interview: Stephen Robles, AppleInsider Podcast Host Sep 28, 2020

Jason 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 find Stephen on Twitter @stephenrobles

Subscribe to the AppleInsider Podcast on Apple Podcasts

Stephen's super-fast podcast editing workflow on the iPad Pro uses Ferritte.

003. All About Screens Sep 24, 2020

Jason 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’re awesome, or if the whole idea is just something nice to look at that hasn’t quite realized its own potential.

Blue Aluminum Apple Watch Series 6:

The 5 Best New Productivity Features in iOS 14

5 Things Coming to iOS 14 that You Should Know

You've Been Wearing Your Apple Watch Wrong

Widgetsmith Things Spark

Interview with Brian Halligan from HubSpot Sep 22, 2020

In 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.

002 - Is the Series 6 Worth It? Sep 17, 2020

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 way too many unread emails.

Finally, a few self-care tips, including why naps are good, and how Jason and Jess are very different.

As a bonus, if you listen carefully, you can hear what it’s like to try and record a podcast with 4 elementary and middle school-age children in the background. This is real life friends.

Apple Watch Comparison Pomodoro Technique Trello Things Spark Email

How Using an iPad Pro for Work for 6 Months Has Changed Everything The Complete Guide to Remote Work

Everything You Need to Know About Using an iPad Pro as Your Primary Work Device

001-Apple Watch Insanity Sep 10, 2020

In 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 sponsor link)

Get a Series 3 from Apple (also not a sponsor link)

3 Unexpectedly Simple Reasons the Apple Watch Is the Ultimate Productivity Tool

Amazon Echo Show (affiliate link)

My recommendations for the best headphones.

And, here's why you really need a good pair if you work remotely.