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Tim @ 5:52

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Hello boys and girls, lemurs and squirrels. This is Tim Ferriss and welcome to another episode of the Tim Ferriss Show where it is my job to deconstruct world-class performers and tease out the habits, routines, morning meditation practices, favorite books, whatever it might be that you can use and test in your own life.

One of my most popular episodes to date was with Matt Mullenweg, who is best known or thought of as the lead developer for WordPress, which now powers more than 25% of the entire web. He is CEO of Automattic, which is a multi-billion dollar startup, fully distributed. He loves tea. He loves tequila. He loves Chicken McNuggets. He is an incredible guy. Very good at using a keyboard layout known as Dvorak as well. We had a very, very long conversation. You’ve all been asking for a round 2.

So in this episode, he answers your most popular questions, which were upvoted online. You can say hello to him online on Twitter: @photomatt. So please enjoy round 2 with Matt Mullenweg.

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Matt @ 7:09

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Alrighty. Hello, hello, everybody. This is Matt Mullenweg, coming back to the amazing Tim Ferriss Podcast. It’s been actually not that long since I was last on here, but lots has changed for me and the company. When I was last coming to y’all through that conversation with Tim filled with much tequila, WordPress was about 23% of the internet and we have gone up to about 26.5% of the internet, which I am really happy about. My company, Automattic has changed a lot in that time, too. We were about 300 people when I last spoke to Tim and we actually just this week passed 500. So things have grown a lot.

But I am excited to be checking out some of these questions you’ve sent. Tim had them compiled. So I guess let’s go ahead and dive in. Let’s start from…

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Steve Rebel @ 8:08

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What’s the hard part about running a company with a distributed workforce, one that others perhaps don’t fully consider when trying the same?

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Matt @ 8:17

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Hmm. You know a lot of the how-to and technical sort of logistics, the tactics of running a distributed company, I think are getting better and better. We use Zoom for video conferencing and Slack for chat and P2s on WordPress instead of email and Google Apps are really good… So, a lot of the basic tools are out there and they are getting better every day. In terms of being able to communicate, certainly with one person, you can do that extremely high fidelity, almost instantly, from wherever you are in the world, with an internet connection.

I think there are still challenges in terms of getting a group of people on the same page. However, I don’t perceive those challenges to be that much different from what people who work in the same office have. I talk to friends with startups of a similar size to Automattic– 4 or 5 hundred people. They are typically spread across a couple of floors in a building or a campus. They talk about how they have to repeat themselves a lot and, sort of, really honing messages and do town halls, and all these sort of things that get everyone in the company on the same page. So, I think that just might be something difficult with groups or scaling an organization. As soon as it goes above what can be in one or a couple of people’s heads, there is a drift that happens between how different people imagine what the goal is.

The thing that I found best for that, even though it wasn’t your question, is to have some sort of prototypes or mockups or this Amazon thing where when they are starting a new project they write the press release for it. Or I would call it write the blog post for it. Write what the announcement will look like when you tell the world about this.

Technics and that, you know low fidelity mockups, can really help make sure everyone is thinking about the same thing, when you use the same words, which is surprisingly difficult.

Finally, the thing that I will say is hard about distributed, that is not talked about, that I think I uniquely appreciate right now because once a year the entire company of Automattic comes together. We call it our Grand Meetup as opposed to the normal meetups, which teams do individually and are usually like 5-10 people. The Grand Meetup we bring the whole company. This year it was in Whistler, British Columbia, up in Canada. We had about 460 people out of 500 there.

It was incredible. It is pretty much like my favorite week of the year. People are so different. Everyone is weird in their own ways and unique and has crazy hobbies. A couple of days before I actually did Overlanding with 2 colleagues from Calgary to Whistler so we were off-road and doing crazy things in jeeps. There was a band where people played together. Everyone gives flash talks so like miniature, little 5-minute talks about a topic that they are interested in.

The aftermath of that is that I think the thing about being distributed is that it can be a little lonely. Like, I really love my colleagues. I love spending time with them while I learning about them. I love talking to them. It is true that in person is still the best way to connect with someone. Virtual has gotten better, but there are so many more senses that are engaged and ways that you can read people and you can share a drink, or break bread, or share food. When you are in person, we just don’t have a virtual equivalence for that yet.

I think that is one of the hardest things. Assuming that you like your colleagues, you miss them and it can be a bit lonely. So, one thing that I always encourage, especially for younger folks maybe just out of college joining Automattic, is to make sure that you have a good social life outside of work because sometime we default to getting that human connection and that engagement from our colleagues.

That is not a bad thing at all. I am a little jealous of the folks that go to an office every day with awesome people who get to do that. But when you don’t have that, it is important to develop that social network outside of it. It is one of the reasons that I love hanging with Tim or other friends in San Francisco when I am there. When I am in Houston, it is a lot of my friends from high school and family. Making sure that you have that social layer to support you and keep you connected to the world so you don’t become a weird hermit. [Laughs]

Alright next question…

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Jeffrey McCloud @ 13:06

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Now that you have many hours of travel and work under your belt, what used to be an annoying experience with working on the road that you have adapted to or overcome?

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Matt @ 13:17

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Hmm… So travel wise I would say that two of the coolest things you can do as a traveller, especially if you are a US citizen, is get Precheck. It is a total game changer. And, I think this is related, there is a program called Global Entry that lets you bypass all the custom lines when you are re-entering the US, not all the the custom lines, the immigration lines, and just go straight to this machine that scans your fingerprints and you just breeze on through. You feel like you are in the future. It is amazing. So that definitely… whenever I go through the Precheck line or the Global Entry line, I just feel amazing. [Laughs] Which, I don’t know if it is totally rational, but it feels really good.

The thing that has probably changed the most over the last few years is just connectivity. You can have LTE connection in the US pretty much everywhere. But when I’m international, I use Google Fi, which is a cell phone service from Google that works in 100 countries. It’s 10 buck a gigabit. Or, if I am going to be in a country for a longer period of time, sometimes it is cheaper to just buy a local SIM Card. But, once you have that LTE connection, you don’t have to worry about WiFi anymore because you can tether to your computer. You don’t have to worry about things like if the coffee shop I am in offers this, or does my hotel.

Hotels are the worst for WiFi. The more expensive the hotel, the worse it is too. You could stay at like a Motel 6 and they have like fast and free WiFi. And then stay at like a Ritz Carlton and they want to charge me $15 or $20 a day for it and it’s so slow.

Just that mobile connectivity, I think has changed because any place that I have my backpack and an internet connection, I can be fully productive. I can have my keyboards, my mice, my headphones, everything. I can work just as if I am at my desk at home and connect with other Automatticians and just do my job I have to do as CEO. That is the thing that has definitely helped me the most.

I also am constantly updating sort of the kit of what’s in my backpack. That is kind of my superhero bag, everything that I have. I do a blog post on this once a year. If you just search for, Matt Mullenweg what’s in my bag you’ll see them. I am sure Tim can like in the notes as well. So that changes every year. Yeah, check it out. Check out that blog post.

Another from…

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Jeffrey @ 15:48

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If you start from scratch with what you know now, what part growth, personal, professional would you have admitted or asked for more of?

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Matt @ 15:57

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I think on the professional end I just emphasized that hiring and being thoughtful about hiring is the best way to scale an organization. I feel that is one of the things that… Tim usually has that question of, “what is your super power?” I don’t actually remember what I said last talk, but if I were to answer it today I would say it is hiring. I have done it now enough and have looked at enough resumes and everything. We have a process at Automattic which tries to remove a lot of the bias from things. You know, you get the right people around the table and it makes all the difference in the world.

What I would tell my younger self to avoid professionally would probably… This one is a little tricky… Oh, that is one thing I forgot. After the podcast with Tim, and before now, Automattic doing another round of funding. We raised about 160 million dollars. Maybe that was before. I don’t recall exactly. That funding has really transformed the areas that we are able to move into, the things we are able to work on. I think that at previous points in Automattic’s history we were capital constrained. That held back our growth, the growth of Automattic, the growth of WordPress a bit.

The other thing that I’ve really been learning a lot that I would tell my younger self is the thing about marketing… [Laughs] I’ve always been kind of like an “if you build it, they will come.” To be honest, for most of my career, that worked.

I’m now starting to appreciate more and more how marketing and getting your message out there is the right way. It wasn’t that WordPress didn’t do it before. It was that we did a lot of it and didn’t really think about it. We kind of lucked our way into it. I think being systematic and approaching that with as much care as you would, you know, the pixels of a design or how an interface works or how the architecture of the code is is really crucial to a great product. It is one of fundamental tenants and basis of a product that resonates with a lot of people.

On the personal life, I would probably tell myself to start meditating more. Yeah, all the basic stuff: meditate, exercise, eat well. Boring stuff that I am sure you’ve heard on every single podcast Tim has done. More on the personal side, I would say that learning to be vulnerable was something that, especially when I was younger, I was just like, “Go out into the world, show no weakness.” Because I was young and I was often operating with people who were decades older than me or getting investment. I thought that I had to be invincible or put on this air of invincibility. Of course, no one is invincible.

As a leader, and actually through meditation, I’ve become a lot more empathetic. Part of that isn’t just understanding and feeling other people’s emotions, but really being willing to show your own weaknesses and emotions and be vulnerable. I think it is Brene Brown’s book, Daring Greatly, talks about this really well or Krista Tippett’s Becoming Wise, another great book. These things… I will just leave it at that. [Laughs] Those are some good areas for listeners of the podcast who have maybe done all the stuff from 4 Hour Body or 4 Hour Workweek and are thinking about growing their soul more, it might be some avenues to investigate.

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James Clomitt @ 19:36

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What’s the most important skill set for an entrepreneur to develop? What characteristics do you look for when you are recruiting new employees?

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Matt @ 19:44

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Another question that I think is a little related to this…

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Theo Harriss Dmarhost @ 19:49

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What are some skills that you look for in non-technical people?

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Matt @ 19:56

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I am going to tie that into the recruiting question. So, important skills for an entrepreneur to develop: resilience, a balance, where you can maintain your health, both mental and physical while working really, really, really hard. Exactly what I just talked about, having empathy. Actually just yesterday I saw an amazing presentation from Julia Hartz, who is CEO of Eventbrite, where she really spoke about this as a lesson that she has learned over the past 2 years. Being vulnerable and showing empathy is one of the things that has helped her most as a CEO, which is so counterintuitive. I would say that those skills are very important.

Also just the basics. If you are an entrepreneur, learn about term sheets, learn about preferences, learn about all the mechanics of your business. Know enough accounting that you can talk to your accountant. Know enough development that you can talk to your developers. Know enough marketing that you can talk to your marketers. You have to know at least a bit about really every part of your business because that will allow you to hire and recruit people that really understand it. Of course, you want them to understand it way, way better than you, but by having even just a common vocabulary that you can converse with that person, you’ll be able to operate with them at a much higher level than if you were just a complete novice in their given area of expertise.

By the way, you can also have them teach you. It is an amazing way to grow these skills. I rely on our ops team at Automattic very, very heavily. I think that has been one of the things that we have been really lucky about. Everything with HR and finance and legal and everything, they are just super top notch. I both learn a ton from them and don’t have to worry about that, which has been amazing.

So, “the characteristics that you look for in recruiting new employees” and the “what do you look for in non-technical people” question… Really here… There was a saying by a basketball coach, “you can’t coach tall.” The qualities that I look for are the things that you can’t really teach. That’s work ethic, taste, integrity, and curiosity. If you think about all of those, if someone has those four things: work ethic, taste, integrity, and curiosity. I believe you can learn pretty much anything in the world.

If you look at any expert… This is something that I think is good to remember. If you look at Elon Musk on space rockets or Tim on health and fitness– well, all the things that Tim is an expert on– any of these different areas, remember that at one point that person knew nothing about it. We are all born, we all learn. I really do truly believe that you can become an expert in any field if you put in the hours and the work and the practice and everything. If someone has those four things, I know that they will be able to rise to whatever the job and role requires of them. Of course, we look for experience and such in order to shortcut that process a bit. But I also know that for every person I hire at Automattic that what we are doing today and what they are hired for is likely not what we’re doing five or ten, and certainly not twenty or thirty, years from now.

When we hire, I do it with the expectation that someone is going to be at the company for decades to come. It is not just a short stint. It’s something that is really a long term relationship. It is like getting married. I think about not just where they are today, but how will they adopt when the company changes and when the world changes and when we are all in the singularity. Those sort of intrinsic and hard to teach things become more and more important.

Next question…

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Rockum Fard @ 24:02

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If WordPress is the platform of writing and Shopify is of commerce, what other similar platforms do you think are worth developing?

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Matt @ 24:10

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That is a good question. There are a few areas that I think that are sort of like fundamentals for interaction on the web that there aren’t great open source tools for yet or, in some cases, good tools in general. One area that is getting a ton of investment now that even though there aren’t perfect open source things, I think that we are in a pretty good place is just messaging. Between Slack and Facebook Messenger, Telegram, Whatsapp, messaging built into platforms like Instagram and all this. I feel like that the communication side of things is being pretty well invested in.

But then when you think about how communication happens online, there is still so much to do there. So, for example, we actually have something we’re reviving a bit called Bliki, which is a combination of a blog and a wiki. The basic idea is that wikis are pretty cool, but you lose when you have everybody being able to edit everything. You lose some of the elements of moderation or curation that make many websites great. So a Bliki is essentially something in between. It is a moderated wiki so anyone can edit it, but the edits go through a moderation queue much like the comments on WordPress go through a moderation queue that can be accepted or denied. So you can get kind of the best of both worlds of community participation and the curation and editorial direction that comes from great websites and blogs. So I think wikis are an area that needs some innovation.

Forums as well. You know, forums are so much fun. I’ve learned a lot about what I’ve done and had a lot of great conversations on forums. I know Tim has as well. It is kind of one of these things that forums aren’t really sexy so no one talks about them or looks at them. We have a product called bbPress there that we use for the support forums on Worpress.org, Wordpress.com, and it is used by some other folks. That is definitely an area that I would like to invest more into. I think there needs to be better platforms for it.

You mentioned commerce and Shopify. Shopify is an incredible tool. Commerce is actually an area that we have moved into. We did an acquisition of a platform called WooCommerce, which is built on top of WordPress. I think that commerce… For many ways, commerce is where blogging was in 2007-2008, where there are some great hosted tools and some great open source tools like WooCommerce, but if you want to use WooCommerce you’ll probably need to be a little more tech savvy or have a developer. We’re entering the area much like where WordPress was in 2008, where we are starting to make it so anyone can use the software. So you kind of get the best of the ease of use of one of the other platforms, but the flexibility of having complete control over your domain, the code, everything. You can customize it. I think that is a winning combination. I hope that over the next couple of years WooCommerce can live up to its fantastic competitors in the marketplace, including Shopify, Ecwid, BigCommerce, etc.

Finally, I would say… You said that we are the platform of writing and I am very flattered there, but still with blogging and especially with comments, I think that there is still so much more to do. You just got me really excited to get back to work. [Laughs] I almost want to stop the podcast and go talk to some teams around WordPress and Automattic. That was a good question. It got me pretty… You know the toughest thing that I deal with day to day is a lot of the stuff I just talked about. Outside of Woo, which we making huge investments in, our ideas we had sometimes even 5 or 10 years ago that because of opportunities with our main business lines, which are WordPress, JetPack, and WooCommerce, are so huge that we have to focus in on them. There were years… And maybe this goes back to something I would tell my earlier self professionally.

In the early years of Automattic, we diluted ourselves, we spread ourselves too thin. So we really had to say “no” to a lot. There is that famous Steve Jobs or Johnny Ives line: “A great product is saying no to a thousand things.” I used to think that was like a thousand buttons and you say no to 999 of them. I think now it resonates with me more saying, in addition to these things that we are focused on, there are like 999 other things I would love to be working on and areas that I would love to tackle. It is really saying no not to even just a feature of the product, but to working on other products entirely. It’s one of the things that makes me excited about scaling Automattic from 500 people today to 5000 people in the future is that we can do our core areas really, really well and make sure that those continue to be the best in the world, but also expand the breath of what we work on.

Next question. This is from Jocko Timinin. I apologise for everyone’s’ names. I am doing my best to pronounce them. Send me a tweet or something afterwards if I could do it better. This actually relates to saying “no” to the 999 other things.

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Jocko Timinin @ 29:45

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What has been the most important default setting in you that you have later questioned and removed? By default setting, I mean a value or behavior that’s been hardwired by parents, environment, education, or society.

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Matt @ 30:01

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You know I think it’s almost just more than just a specific default setting, which I probably have some things that I do differently like I type a Dvorak layout instead of a Qwerty layout or, you know, living distributed versus living in a home or being in one place, building companies in a different way. It’s just the fact that you’re constantly looking at default settings. So I would say, Jocko, by this question, you’re probably thinking about it the right way because my default settings and the way I grew up in society and all that is going to be different from yours so the things that need to change will be different since our situations are different. So what you should think about is just asking yourselft that question at various intervals. And this is why I love that Christmas/New Years time because it forces you to take a step back and kind of look from the 10,000 feet view.

But I try to do this… It is actually something that happens a lot when I try to mediate and I can’t quiet my mind and I am thinking about lots of things. Some times I will just take a pause and be like, “OK, I’m just going to not meditate, but also not do anything– not look at my phone, not do anything.” I’ll have a piece of paper and just see everything that is caught up in my mind. Where do I think that is going? How do I think… sort of unwind my mind in terms of what’s stuck in there and what are the things that I am thinking about. It often leads me to take that step back from the day-to-day and look at things from a broader sense. Is my life heading in the right direction? Our my relationships in the right place? Who are the people that I love and care about, but maybe haven’t spoken to in a few weeks or a few months or maybe even a whole year? So, those sort of steps back I think cause you to look at your own operating system. I actually think that mediation is something great for that as almost like an interupt.

I read a cool book called Search Inside Yourself. It is by a fellow at Google that started a– I think it is even called Search Within Yourself– meditation and mindfullness program. I believe his name was Chade-Meng Tan. He has an engineering background and Googler so I think the book is pretty cool for leaders of companies because it talks about the business benefits of mindfulness from an engineering point of view. How mindfulness and meditation is almost like a background process that runs and then whenever your operating system throws up an interrupt, like a reaction or emotion to things, it can kind of catch that. So before you immediately react and do the thing that is sort of your first intuition or reaction to an emotion or thought, it says, “Hey, what a second.” That is essentially the muscle you are developing when you meditate. When I started to think of it that way, I was like, “Wow, OK.” Just like I might do a plank or pushups or something, like I need to work this muscle everyday if I can.

I think that is impossible to do and not think about your default settings or go back to the first principles of why you do things. The reason that you got into what you do in the first place. Are you truly happy? These are tough questions, but ones that you can honestly, with the distractions of day-to-day life with our phones and our blogs, social media…. It is so easy to just be lost minute-to-minute and to be busy all day and not really bring yourself closer to the mountain that you want to climb.

I would say if you are listening right now maybe even pause and just take 10 minutes, whether you are driving in the car or whatever you are doing, just pause the podcast and do nothing, have zero inputs, and just think about that. Alright, I guess we are back now.

Next question…

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Matthew A. @ 34:18

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Hard work in and of itself does not seem to guarantee success. There are plenty of truly hard working entrepreneurs whose businesses will fail. To what other factors besides hard work, do you attribute your massive success in business? Luck, good mentors, timing?

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Matt @ 34:38

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Alright, Matthew, which is an awesome name. Thank you for that question.

I think it’s funny that people call me successful. I don’t think of myself as that way. I think part of that, even though that I know objectively by many measures I have been… I have been extraordinarily fortunate and lucky and everything. But part of it is because I fail so often. I don’t think that, you know, yes, if 10 businesses were started today, 9 of them would fail. By the way, including if I did them. So it is not how many times you fall, it is how many times you get back up is really key. People talk about resilience and all these things. That is true. Even think of business icons like the greatest companies of our time. Facebook has products that fail all the time. They launched Poke like a Snapchat ripoff. Amazon, which I am a huge admirer of Jeff Bezos, do you remember the Kindle Phone that was just last year. That was a huge failure. And not just a huge failure, but one that they must have spent the better part of a billion dollars on. So we don’t stop failing. It is just you want to hopefully design your systems to assume failure and have some backup plans– a Plan B, a Plan C, a Plan D, all the way to a Plan Z– so you will be able to get up and fight another day… just whatever that drives you to do it. I think that having a higher motivation beyond the extrinsic things that might come from success, something more than money, something more than material goods that motivates you is really key.

Yeah, so that is kind of the thing that I would attribute it to. Especially in business press, we just see when people hit the home runs. We don’t see all there at bats. Very rarely do we even know about all the at bats they had. Just remember that. No matter how bad of a day you think you are having, there is probably someone you admire who is probably having a bad day right this second. You are not alone.

Next up…

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Julian B. @ 37:04

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You have 30 minutes before the end of the world. You find yourself in a very well stocked bar next to an amazing varied delicatessen. Which choice of food and drink did you enjoy?

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Matt @ 37:16

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I like this question a lot because, well, I love food and drink. I am actually on a quest right now to go to all the 50 top restaurants in the world. There is a list that gets published I think by Pellegrino or sponsored by Pellegrino. I’ve been to 9 of the top 10. I think about 40-45% of the top 50.

These experiences from these chefs… It’s a whole out of this world thing. But I love food and drink. Now usually when I am drinking… Part of why I like this question is, you know, 30 minutes before the end of world and generally when I engage in libations, I try to stick to the same alcohol all night. This is just something I’ve learned from trial and error, mostly error. When I mix different types of alcohols, I feel kind of terrible. I heard a saying once: “Drinking is borrowing happiness from tomorrow.” [Laughs] That is true to an extent, especially if you mix. But if I stay with one, you know, if I stay with the great Casa Dragones all night or wine all night or whiskey all night– I would say those are my 3 favorites– of course, to a reasonable degree. If you have too much of anything, it is bad for you. I am typically pretty okay the next day.

But the truth is that I love all sorts of different drinks. There are great drinks made from gin and rum and other things that I would love to have, but I typically avoid because I am like, “I don’t want to drink gin all night.” So for the drinking part of things, I would basically have like a bunch of everything at the bar. [Laughs] And just enjoy it. Preferably some great cocktails. In terms of a wine, I would have a great… I actually love California Wines like an Alpha Omega… just some of the classics.

Basically the last thing… I am going to assume that this delicatessen has a Foie gras. I know this is so bourgeois I can’t believe I am even saying this, but there is this experience where like foie melts on your tongue and then you wash it down with like a great Sauternes like a Chateau d’Yquem or just the best one that the bar has. It is a party in your mouth. It is almost impossible to describe the sensation of what goes on there with those two tastes interacting. That would be like 29 minutes and 45 seconds.

Otherwise, from the delicatessen, I would probably just go for a couple of good sandwiches. Definitely like eggs and cheese and bacon on a croissant is a go-to that always brings me joy. It is funny. We are coming up on Thanksgiving and every Thanksgiving I am like, man, turkey is so good. Why don’t I eat more turkey? Especially, those day after turkey sandwiches, where you have the pulled turkey, like the dark meat, then you can get some mayonnaise, cranberry, and horseradish, just kind of mix up the sandwich a lot… pickles, lots of pickles… maybe even try to mix in some sauerkraut or some kimchi, like something fermented in there. That would probably be my go-to, super good deli sandwich.

Julian, thank you because this question was super fun for me to think about. [Laughs] Because I really went a lot of different directions. There are some mixed cocktails, some good wine, and then ending it out with a great Sauternes.

Alright, next question…

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Alexander F. @ 41:04

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Matt, what are your thoughts on artificial intelligence web developer/designer tools, such as the Grid or Wix ADI? Will Wordpress use some sort of AI developer or designer feature in the future? Or just an AI?

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Matt @ 41:21

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Umm… This is kind of funny. I don’t like to talk bad about competitors so I won’t mention any specifically, but I do think that right now there is kind of almost like a completely vastus, marketing hype cycle around AI that has nothing to do with artificial intelligence at all. So people are just slapping AI on everything. Maybe before they slapped “cloud” on stuff. That just isn’t AI at all. [Laughs] I think it really is just marketing. Nothing I have seen in the marketplace so far is much more than vaporware and a good demo. I do think that… essentially what they come down to is kind of wizards. It is not that much different than a clippy would do in Microsoft Word in the 90s. I think there are much better approaches to that problem.

Now, embedded in that is the question of do I think there are changes we can make to WordPress to make it easier for folks to get going or get started? The thing I think about, what is really our biggest challenge and the thing I think about everyday, which is how do you connect/bridge that gap between what someone imagines and what they are able to create. So, absolutely and that is what we work on everyday. Big parts of Automattic work on how do we make it easier, more intuitive, to have that effortless flow as you are building things. That is at the core of what we do.

In terms of AI and sort of that impacting the business, I think that we are still many years away from that being more useful than a well designed, traditional interface. There is actually a really great essay about this. We’ll find the link for the show notes. But essentially there is a fellow who looked at all the chat bots, which are sort of an area of AI right now– for Messenger for Telegram, there are these bots. You can say, “Hey, I want a pizza.” They are like, “What kind of pizza do you want?” You are like, “How about some pepperoni?” Or maybe it is smart so it says, “Hey, you usually get pepperoni. Do you want some pepperoni?” You are like, “Yeah, let me have some pepperoni. But, oh darn, it is not my cheat day so deliver it on Saturday instead.” You sort of have this conversational interface, which sometimes people call AI, with this product or service that you consume or buy or interact with. Basically, what this essay does is compares that model to what a lot of folks in the US are trying to copy, which is the success of platforms like WeChat in China.

It shows that how these days WeChat actually… It’s not that you’re purely chatting with someone and asking them, which sounds to me like the inconvenience of calling a restaurant to get a reservation versus using a Reserve or an OpenTable to get one. WeChat really embeds these interfaces. He talks about the number of taps it takes to chat with a bot to get something versus the taps it takes– I think he may even use the pizza example– to order a pizza in China on WeChat through this mega-conversational platform.

I think that is one of the areas where a great interface can surpass a chat. One thing that we’re doing. I’ll give y’all a preview of something we are working on for WordPress.com… We actually are working on a new chat interface. For paying customers, we provide live chat support. It’s a great experience. You are connected with a real, live human being and they will help you through whatever you are having trouble with. So it is basically like real intelligence. It is much better than artificial intelligence. They can help you with anything. There are some disadvantages to this though in terms of it is difficult to scale, in terms of we are hiring people as fast as we can. We are happy with the happiness engineers at Automattic, but we want to create tools that enable them to reach more people.

So we are working on this new chat system. The two big things it changes are: 1) it abstracts out who you are talking to because right now… And, by the way, I do live chat support sometimes too. So if you are chatting and you have maybe 3 or 4 chats going on simultaneously; you are helping people. It is a little bit difficult both to wrap those up, like let’s say you want to go to lunch, but even things like using the restroom. You don’t want to leave the people you are chatting with hanging because they are waiting for you. By abstracting it out, you would basically be chatting with like an agent or cartoon character– whatever it is that we decide– instead of a specific person. We can allow transferring of chats between people way easier behind the scenes. You can have a I’m going to the bathroom button or the my dog just started chewing on the couch button. The chats could be transferred to someone who gets all the transcripts and everything, and could just pick it up instantly and keep the chat going invisibly to the person they are chatting with. 2) Is that we are looking at… and this is an area I like where more than artificial intelligence, which is machine learning. We now have all of the chats, at this point probably close to a million interactions or way more than a million–emails, chats, everything. So we can apply and I am going to say a buzz ward, “deep learning,” which I am going to say is not totally hyped because there has been some amazing open source tools released by Google like TensorFlow… All the technology is pretty useful here to learn from those and essentially augment the happiness engineers– people doing support– by when we get something like looks a lot like what we have seen before, we can suggest essentially like a pre-reply, like an answer for them that saves them from having to type out or do everything. Then they can customize that or use that to augment their ability to chat with folks. This has been a pretty cool project in an area where I think AI could actually have a real impact versus just being marketing hype.

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Hymet F. @ 47:54

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If you hadn’t accomplished what you’ve accomplished and started over with nothing, what would the next 6 months of your life look like?

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Matt @ 48:01

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This is a pretty tricky question because there’s a lot of ways to think about it. I think the first way I thought about it was if I just lost all of my… like I lost everything. I had to declare bankruptcy and no assets or anything. The obvious thing is that I have lots of friends and family so that is sort of my safety net so I would probably maybe move back in at home and start to rebuild from there.

But that is probably not how you intended it. [Laughs] Hopefully… Unless the question is you don’t have friends and family that you think would take you in if you were having a hard time then develop some deeper relationships, you never know what is going to happen. By the way, that means that you will take them in if they are having a hard time; it is totally reciprocal.

There is a version of this question that I have seen before: like what if you knew everything you know, but you are homeless one day so you lose everything and you don’t have any friends or family you can sort of fall back on. So you are kind of alone in the world, but you have all your knowledge, what would you do? My answer there, again this assumes, you know, the privilege of being in the United States and things like that is that I would probably go to the external version of friends and family, which is maybe a church or a YMCA or one of the non-profits that tries to help out people with nothing, and sort of use that as a home base to then develop.

The other version of this that I thought of was well what if instead of all that you have your house, etc.; you don’t need to worry about surviving, but you are starting something brand new. The thing that I would first here if I know everything that I know now. I would use my craft– engineering or music– to essentially get a job. So I think I would probably look for the most interesting company I could get access to and just do my best to be hired there. Create a really great application. Really learn a lot about their business and go into the interview knowing a lot about it. Try to stand out. If they say “no,” keep trying to be hired. Just try to get around a great group and have a great job where I know I’ll learn and start to save and develop the net for which I could something more entrepreneurial in the future if I wanted to, which I think is what you are getting at with the question. There was a saying when I was a musician: “You never want to be the best musician in the band.” Ideally, you are the worst musician in the band because that means you are learning from every single person around you. So I would try to find a company or group or some place where I could be the worst musician in the band, where just every single person was so much better than me. I still made the cut to make it in, but then I would just be learning from everyone around me every day.

If I was just trying to start something new and it couldn’t be related to anything that I had done before so it couldn’t be content management or e-commerce or any of the areas that WordPress kind of plays in, I think what I would try to do is figure out the Zeitgeist. You know, I would buy a copy of the New Yorker and New York Magazine and The Economist and Wired and Fast Company and I would just read them cover-to-cover, maybe for a month or two, maybe get some back issues. And try to figure out what area is like in the good part of the hype cycle. Something like VR or AI is probably in the bad part of the hype cycle, where the expectations that people have for it are so out of line and we are just too early in terms of the impact that the technology can have. So I would try to look for an area that is no longer… Maybe I would go back like 3 or 4 years in those magazines and look for something that was hot then, but no one is talking about it now. That is probably where the biggest opportunities are. So, the thing that everyone was excited about 5, 6, 7 years ago. It got a ton of over investment and companies have started and failed, and now it is at the point in the cycle where the real stuff is happening. Like kind of the carpet baggers and the folks that were just in it for money have all come and gone, and it is just the people who really want to make a difference in the world are still there and working. In some ways I think content management is in this area right now, where a lot of the hype was 4 or 5 or 6 years ago, but now we are actually reaching scale and having an impact on hundreds of millions of peoples’ lives. That is where the big opportunity is.

It might be outside of the web– areas like CRISPR or gene editing. Some of the bio stuff I think is getting pretty interesting. We are approaching times when the devices… Some mobile stuff is probably in this area right now, where, you know, we have more than a billion mobile devices. No one is really thinking, “Ah, I am going to start an app,” but that is kind of when it is most interesting to start an app.

When WordPress started, the biggest criticism was that there were too many blogging systems in the world, we didn’t need another one. That would be what I would try to find: What does the world say we don’t need another one of because there are plenty of it? And try it out.

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Carlos R. @ 53:28

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Where do you see the future of the internet in terms of user behaviors given that 20 years ago people started to use and visit websites and now most people just use their phones? And when VR becomes useful, it is likely that we will all live on a VR platform and the phone will fall like the desktop.

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Matt @ 53:44

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Hmm… My hope is that phones don’t fall like the desktop because even in a world where the VR is super amazing and we will all be plugged into the matrix, I still really hope that I can go on a hike with Tim or like get out into the world and see some of the beautiful things all around us in nature and in cities…. and instruments live and concerts and things like that. So when I am mobile something like a phone hopefully will be on me… and I hope that is still there.

In terms of the internets, I think that the behavior that is changing the most is still just this mega-trend that we are still riding where there are 6 billion people still coming online. So everything that we think is amazing and huge and big now is going to 6X or more likely 10 or 100X where it is in terms of user interaction, in terms of posts per day, in terms of number of people tweeting like all of this is going to be so, so much bigger than even the already amazing levels it has reached. As people become more comfortable being native online, the same cycles that people listening to this podcast might remember about 15 years ago where you were like nervous to put your credit card online or things like that. Folks coming online for the first time are going to have those same nervousness and go through those same, hopefully accelerated, learning process of like what it is like to truly live digitally and live online. So I think that will be adopted faster. I also hope that payments will be an area where we can have a lot of innovation on because the friction of payments I think puts us in business models like advertising right now which aren’t the best. You know, how cool would it be that everyone listening to this could give instead of Tim having advertising or doing whatever he needs to do, everyone listening to this could just put in a dollar or maybe even not a dollar, maybe put in like 2 pennies– some sort of micro-payments that could support creators all over the world. Right now the payment systems that we have just aren’t setup for that, but I could imagine something like that being really cool in the future.

The thing that I think is going to have to change user behavior wise is we need to develop more antibodies, more immunity, because the technology is going to get better and better and better at engaging us. Machine learning, and in the future 20 years from now where we do have something more approaching artificial intelligence, could entertain us perfectly and keep us always connected and engaged with whatever companies want us to be engaged with because, you know, a lot of this will be commercially driven. That worries me a little bit. It is a little more Brave New World than 1984. Reminds me of that great intro to I think Brave New World… No, no, no, it is Neal Postman and I think he wrote a book called Amusing Ourselves to Death and there was an intro, which we will put in the show notes, that someone made into a comic that was pretty amazing in terms of what 1984 predicted would be our oppressors like Big Brother, and what actually is our oppressors, which looks more like Brave New World. We are kind of, just like the title of the book, amusing ourselves to death. We are so caught up in distractions and pleasure and entertainment that we might be missing out on the bigger things. So just like it took the world 100 years to develop antibodies to an addictive technology like tobacco and cigarettes, I think the world needs to develop antibodies to technology addition and the addiction of really engaging experiences.

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Nathan E. @ 57:41

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With all these web development bootcamps opening up, is our future demand for web developers still high or stagnating?

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Matt @ 57:47

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I actually have been really impressed with some of the bootcamps, especially in contrast to how prepared people coming out of these bootcamps are compared to people coming out of 4-year universities or colleges. So I think that universities and colleges need to really up their game and update if they are going to still be something that people still think is a good investment.

Just a tip for people that are going through or thinking about going through one of those hack camps: the thing that I still see… I have actually reviewed 22,000 applications and resumes to Automattic in the past 3 years so I look at a lot of these. All the web development bootcamp ones seem to follow a little bit of a template so see if you can break out of that a little bit, but also even if you do projects as part of that the thing missing is often just a little more experience. You say, “Well, I don’t have a job yet. How do I get experience?” Open source. Contribute to open source. Get involved with an open source project. That is something that I think would… because you are competing with folks who maybe have 3 or 4 years at Google or Facebook. Things like that. You might be just as good from a development point of view, but you need to get some of that experience in.

So the hack. The cool shortcut there is to get involved with an open source project or start one. And show sort of real world users, real world collaboration with other people. I don’t I talked about that earlier in the things I look for. The most brilliant person in the world, the most greatest developer, the most greatest anything, that can’t work with other people is basically not ever going to have an impact and honestly someone who I would let go at Automattic. It doesn’t matter how great you are if you are not going to be able to work in the context of a team. It is not someone who I want to work with personally. Being able to show that in your application, I think is really key.

The growth for web developers I think is going to grow hugely, but it will also become more sophisticated. Even think about in the 90’s, before something like WordPress, you might need to call your web developer any time you want to change your website. Now tools like WordPress make it easy for you to do that all day long without talking to anyone. So the basics are going to get easier and easier because the software will enable people to do that. So what they need developers for is to become more sophisticated.

I talked about earlier that WordPress you can start and make a great site. If you are willing to use WooCommerce, you can definitely get started with it, but maybe to customize it how you want you need a developer. So that is where the demand for developers is going to be. So you need to become more and more sophisticated as the general world becomes more and more sophisticated.

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Tom T. @ 1:00:44

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Considering the heights that you have reached, how do you motivate yourself on a daily basis over the course of any projects?

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Matt @ 1:00:52

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You know, I am actually really lucky. I just got 2 awards in the past few weeks. One was a Fortune 40 Under 40, which I guess is a recognition not an award. The other one was the Heinz Award, which is I am really super honored by. It is kind of the MAcArthur Genius Grant or something. They pick 5 people by year in different areas. It comes with $250,000 grant. It is a huge honor. I am even blown away that I was considered for it. So to win it was very humbling. When these things happen. When the recognition comes in, or like you put it, “the heights that you’ve reached.” This is a new height that I have reached. This is a new height that I have reached. If anything it makes me work harder because I am like I don’t want to let down the people who chose this; expectations are that much higher for what I need to do. I just want to… If the world has given me something, I want to give it back 10 times that. I would say that success can actually be very motivating to not let the world down in terms of like you been lucky, it has blessed you. How do you give it back? How do you pay it forward? And it is not just being more successful, it also just like literally how do you give it back. How do you put goodness into the world? How do you give it away? That is really, really key to balance that importance.

I will just give a little tip: When I have a grind. I have reviewed 22,000 applications. There are about 600 waiting in the queue right now I need to look at. If it is something that is a long task– I know it is going to take more than a few hours in order to get through– I often break it up using the Pomodoro Technique. Sometimes I do 25 minutes on/5 minutes off. Sometimes I actually do a longer version where I do 50-55 minutes on then like 10 minutes off because I find that I can really stay in the flow for a longer period of time if I have the right music on and everything like that. So that is something that I use to get through a grind when maybe i don’t have that motivation. Because let’s be honest, no one, including myself, wakes up every morning of every single day being like, “Oh great!” Sometimes you wake up those mornings– maybe you’ve mixed your alcohols like I talked about earlier– and you just don’t want to do anything. [Laughs] But something like a Pomodoro Technique or forcing yourself to stare at the blank page and start typing, just gibberish or whatever it is, just to get kind of the engine started can help on those days when you have no motivation, which happens more frequently than any of us would care to admit.

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Bryan K. @ 1:03:42

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What has been the biggest technical problem you’ve had to overcome and how did you end up solving it?

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Matt @ 1:03:46

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This is an interesting one because as I thought about it all the technical problems that I have faced in my career, in terms of a really difficult bit of code or an upgrade path or bringing in a WYSIWYG to WordPress or any of these sort of things, are fundamentally tractable, meaning that you can essentially chip away at it enough that they are solvable, or you get the right people involved or whatever it is. There have certainly been fun ones. I think back to…

There is a great presentation by a WordPress contributor, Andrew Nacin. He talks about when we added emoji support into WordPress. It was actually kind of a behind the scenes… essentially, we had found a really key security problem in our underlying database which is MySQL, which affected not just us, but everyone out there. The way that we dealt multi-byte characters. This is kind of technical, but normal ASCII text is represented by a single byte and Unicode, which is the system that allows representing every language in the world and also things like emoji, are multi-byte so they might be 2 or 4 bytes long. There was just a really obscure bug that allowed you to essentially do some security exploits by changing how multi-byte characters were truncated. Anyway, honestly it was a ton of fun, really cool. But because the vulnerability was so widespread, including not just WordPress, we wanted to give people an chance to upgrade before that so what we framed as emoji support was actually this Unicode fix essentially, which is funny because we got a lot of criticism. People were like: “Why are you putting emoji in when there are bigger things to work on.” Little did they know. If you are a super geek and into that… If I anything I have just said made sense or seemed interesting, check out Nasin’s presentation there. You will enjoy it.

When I think of biggest problems, it is always the people. You know I talked about WYSIWYG earlier. When we brought in the WYSIWYG editing to WordPress, which now seems like a very non-controversial feature, at the time it was very controversial. And the people side of it was way more difficult than navigating the technical side. The fact that I studied political science in college I think has been way more useful to me than if I had done computer science because fundamentally anything is about people working together. So learning how to manage, learning how to communicate, all of those skills are the things… To kind of go to some earlier questions: What would you take with you? What would you tell your earlier self? Or if you were doing something else? That is the skill that I think I am going to use the rest of my life and continue to grow and develop the rest of my life. It is not any language that I know today or any field knowledge expertise or domain expertise. It is just that working with other human beings and becoming better at it which is the thing I probably, especially as a CEO, think about and try to work on everyday. It is kind of the fun part. Because think about it, most of all fun activities involve at least one other person so if you can interact better with other humans life gets better.

And the final question as we end up about one hour into this…

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Cisari R. @ 1:07:23

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What is your evening routine (if you have one)?

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Matt @ 1:07:27

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This is a cool one. I like, Casari, that you put in the “if you have one,” because this is where I will just be open and honest and vulnerable. I would like to say that I have a cool evening routine. The reality is that, for whatever reason, the way that I currently work right now and live is that I kind of go until the gas tank is empty. [Laughs]– whether that is working, whether that is with friends, whatever. With in a short period of time, run out of gas and I just fall asleep. [Laughs]

I have been very fortunate that I have never had trouble sleeping. My head hits the pillows and people I have dated etc. laugh at this… They are like literally your head hits the pillow, 20 seconds later you are asleep, maybe snoring, I don’t know. It was like what just happened? You were talking just seconds ago. This literally happened last night. I had 4 or 5 friends over. The conversation was going great. I didn’t want to stop them so I said, “Hey, keep going…” But yesterday I had to wake up at like 4 AM to catch an early flight and get some work in and some meetings and things so I was just done even though it was just 10 or 11. So I said, “Hey, keep going. I am going to peace out.” [Laughs] If it had been a big party, I would have done the Irish goodbye where you just kind of leave without talking to anyone. It was just four of us so I said, “Hey, keep going.” I feel asleep and they were still having a great time and I kind of hit the end of the road. So that is my evening routine is passing out. [Laughs] I don’t know if that is super useful.

But I have thought a lot about morning routine. This is the latest iteration, which I think I talked about before, but this is the latest. I still use coach.me, which is the app where you can check things off every day. It is like a daily today list. The things that I try to do every single morning are:

  1. I try to do reading in the morning… at least 30 minutes of reading. I find that is the time in the day where I kind of have the most engagement.
  2. After that I take my vitamins and pills so that is Elysium. I take some of the Nootrobox ones so like Rise and Kado and just some other stuff– whatever Tim has me taking at that time. So like some Ubiquinol, Ginseng, whatever it is. Honestly, I didn’t used to care about this stuff as much. Now that I am in my 30s, I figure it can’t hurt and might help. I’ll do whatever Tim saying most recently.
  3. I try to do a little bit of exercise. Right now it is plank…. I do a plank first then I do squats then I do pushups then I do some Sun Salutations to kind of stretch things out. Again, I am not super into yoga, but I do a few Sun Salutations every single day. It is amazing.
  4. Finally, I meditate for at least 10 minutes. I use an app for that called Calm.
  5. Then I look at my computer. I try to do a blog post at least 4 or 5 days out of the week. So essentially you could translate this into writing.

That I would say is my perfect morning. Now how many mornings do I hit all 3, 6, 8 of those things. Not all of them. [Laughs] Fewer than I would care to admit, but for me that has been the current recipe for a thing that just works best.

So, on that note I will leave all the amazing Tim podcast listeners. You are all a super cool group. I am excited and honored. Thank you to Tim for allowing me to connect with y’all again. And I can’t wait to see the comments and tweets and everything that come out of this. I am happy to engage with y’all. Again, I am Matt Mullenweg. My Twitter is @photomatt. You can see me blogging at matt.blog or at ma.tt and I am on Facebook as well.

End @ 1:10:10