For my first podcast of the year with the WordPress community, I joined the new Do the Woo podcast! It started with a little technical difficulty but ended up being a great conversation about WooCommerce, WordPress, and AI.
Category Archives: Podcast
Wolfram Automattica

It’s exciting to announce that Stephen Wolfram has joined as a special advisor to Automattic.
I promise this is not just because he is such an incredible blogger, using WordPress, natch.
If you don’t know about Stephen Wolfram, his about page is not a bad place to start, but far more interesting is his 2019 essay on Seeking the Productive Life, which includes a setup for hiking outdoors while typing on a laptop.
Stephen was doing the remote CEO thing decades before I imagined Automattic. He spoke at Automattic’s Grand Meetup in 2019 and one of my favorite memories was seeing him at the silent disco after-party. We also did an episode of the Distributed podcast together.
Since he started engaging more deeply earlier this year, I’ve gotten a lot of joy from seeing him interact with teams across the company, asking questions in an incisive, inquisitive way that helps break down problems. We just finished up several hours of a deep dive into our board topics with several hundred Automatticans participating.
Automattic has been blessed with amazing directors over the years. Currently, our board is Susan Decker, General Ann Dunwoody, Toni Schneider, and me.
Open Sourcing Algorithmic Choice
Jon Weeks from the Evening Standard interviewed me for their How to Be a CEO podcast about Tumblr, and as I often do we mostly talked about open source.
If you can’t listen Techcrunch’s Sarah Perez posted a really nice summary of the interview.
Whoop Podcast
Whoop is an excellent biometrics bracelet I’ve been wearing for a few months since my friend Jaime Waydo joined as their CTO. After many years of being very in the Garmin 945 camp, I now do an Apple Ultra for all the smart stuff, and Whoop for all the great sleep, HRV, and recovery information that I use to be aware of my energy levels throughout the day, complemented by the Rise sleep and energy tracker app. This has been my ideal combo.
The founder and CEO of Whoop, Will Ahmed, interviewed me for their podcast, which we covered for a more mainstream audience my passion for open source and creating an open ecosystem for a web, how I got started as an entrepreneur, how Automattic hires, growth mindset and mental clarity, working with Joe Hudson as an executive coach, and day-to-day routine (or lack thereof, sometimes).
Jack Dorsey and Running Two Companies
I had the pleasure of interviewing Jack Dorsey for the Distributed podcast, a conversation that ended up going a bit deeper and longer than previous episodes.
In preparation for the interview I kept coming across people critical about the fact that Jack is the CEO of two companies simultaneously, Twitter and Square, each having over 5,000 employees.
I think what people miss is that at that scale, running a company is not that different from running a large division of a company. No one asks Jeff Bezos how he’s CEO of both a retail company and a cloud computing one (AWS), or Tim Cook how he’s CEO of a hardware business and a services business, and of course with both of those examples the breadth of what the companies cover is much wider. Also as an added benefit, shareholders can choose to invest in Square and Twitter together or not.
All of that said, I think having a CEO-level seat at two of the most influential technology companies today does allow for accelerated learning, as organizational experiments will naturally happen at each company and then the best practice can be shared to the other. Jack wasn’t aware how much peer executives at each company meet with each other to share learnings, but that seems like an obvious win.
Readers of this blog will especially appreciate how much we talked about open source and cryptocurrencies, and his view on the three things he’s responsible for as CEO. Give it a listen and let me know what you think.
Introducing the Distributed Podcast

I’ve been meeting with some brilliant people for Distributed, my new podcast dedicated to exploring the future of work. The first episode is a conversation with Stephane Kasriel, CEO of Upwork, about how they built a distributed culture, and how flexible work will shape the future of the global economy.
Unlike Automattic, Upwork does have an office in Silicon Valley (albeit one with a remote receptionist!). It was interesting to hear how Stephane’s teams balance in-person culture with inclusiveness for all employees, no matter where they live. Read more about Stephane’s work at Distributed.blog, and subscribe at Apple Podcasts, or wherever you listen to podcasts.
I joined in for the James Altucher podcast in an episode that covered a lot of ground. One clarification was the point of the story about my Dad not making much at his old job was that companies should be thoughtful about compensation especially for the people who stay with them the longest, not that loyalty is a myth or something to be avoided. It just needs to be two-way.
I went back for a Round 2 answering follow-up questions from Tim’s readers on the Tim Ferriss podcast. About an hour long and covered a wide range of topics. One of these days I need to start podcasting more directly. In the meantime, please give it a listen! Already some great tweets and responses have started to come in.
I know a lot of people are on their way to SxSW right now, here’s a podcast I joined called The Changelog you can download and check out on the way there (or back). It’s a bit more technical than the interviews I normally do, we talk about Javascript, Calypso, the philosophy of open source and WordPress, some of the thinking behind Automattic’s acquisitions, and my favorite programming books. I hope you can check it out, Adam and Jerod did a great job on this one.
I joined an episode of the Dorm Room Tycoon podcast, which you can check out here.
Last week I did two podcasts around the Calypso news that are both now up, and show very different sides of the announcement. The first was with Brian Krogsgard of the WordPress-focused site Post Status and we talked a lot about the Calypso launch in the context of the WordPress community. The second was the always-fun video group the Gillmor Gang which ranged quite a bit but mostly focused on Calypso in the context of the wider tech world and where we’re going.
I was on VentureBeat’s podcast with Dylan Tweeney, talking a bit about how WordPress came to be and geeking out on some of the tech behind our approach.
Webmonkey Podcast
I was on the Webmonkey Podcast talking about WooCommerce and tech in general, my part starts around 26 minutes in.
Single Malt Scotch Episode
The Single Malt Scotch Episode – Episode #509. I was on Wine Library TV with the inimitable Gary Vaynerchuk talking not about wine, but scotch. Much trouble ensues. Check it out! I ended up leaving my laptop at Gary’s store and had to go back to Jersey later that day. I took a few moments to browse around and discovered an awesome cheese called Ombra.
Kindle Podcast
Matt Mullenweg Loves His Kindle, from a chat I had with Mashable. Posting from Greece, where it’s hot.
THAT Podcast
I was interviewed for the first episode of The Humanities and Technology Podcast.
Random Bits Podcast
Podcast: Charleen Mullenweg
Podcast #10 is up with my sister Charleen. We talk about the art of TV shows, covering Heroes, Battlestar Galactica, Firefly, Buffy the Vampire Slayer, Angel, Babylon 5, Veronica Mars, Stargate SG-1, Stargate Atlantis, Supernatural, Alias, Lost, Joss Whedon, and more. This is a long one, clocking in at 12:46, but the file size is only 3.9mb. Here’s Charleen’s blog. Enjoy!
Podcast: Scott Berkun on Myths of Innovation
Back to podcasting! Podcast #9 is a 13 minute interview with Scott Berkun where we discuss, amoung other things, his new book The Myths of Innovation. It’s my longest podcast ever, but definitely worth it, especially if you’re involved with a startup or want to create something new.
Podcast 8
Podcast #8, which I mistakenly call #7, includes comments on podcasting, wallets, chipping, McDonalds, and Microsoft Office 2007. Hopefully this one shouldn’t sound all chipmunk in flash players. 3:30.