The Startup Ideas Podcast - How to Engineer Serendipity (with Matt Mullenweg)

Episode Date: March 24, 2022

Can a billion-dollar business be built remotely? You don't need to guess if it can happen. For more than 15 years -- long before coronavirus forced work from home for just about everyone -- Matt Mullenweg (@photomatt) was trailblazing the remote work movement as the founding developer at WordPress. Today, the platform powers approximately 30 percent of the entire internet, and its businesses employ more than 1100 people across 60 countries. In this episode of Where It Happens, Matt discusses the future of work, why a distributed workforce is the most effective way to build a company (if you do it right), how you can manifest serendipity and influence better outcomes.Want more community? Learn more here: http://trwih.comTHIS EPISODEMatt Mullenweg: https://twitter.com/photomattSahil Bloom: https://twitter.com/SahilBloomGreg Isenberg: https://twitter.com/gregisenbergProduction & Marketing Team: https://penname.co/FIND US ON SOCIALTwitter: https://twitter.com/_trwihInstagram: https://www.instagram.com/_trwihTikTok: https://www.tiktok.com/@_trwihWeb: https://trwih.comSpotify: https://open.spotify.com/show/6aB0v6amo3a8hgTCjlTlvhApple: https://podcasts.apple.com/us/podcast/where-it-happens/id1593424985SPECIAL THANKS TO OUR SPONSORS🌟 This episode is brought to you by LEX. We’re always looking for breakthrough businesses. And, our audience has repeatedly asked how they can invest in commercial real estate. Lex is the easy answer. LEX turns individual buildings into public stocks via IPO, so you can invest, trade, and manage your own portfolio of high-quality commercial real estate. It’s so simple to get started today.Sign up for free at https://www.lex-markets.com/room and get a $50 bonus exclusively for our audience when you deposit at least $500. It’s a no-brainer.🌟 This episode is also brought to you by Outer. Spring is in the air in both NYC and Miami, and we can’t get enough of our Outer outdoor furniture. Their furniture looks incredible and is durable. Personally, we love the Outdoor Loveseat.Right now for our audience exclusively they are offering $300 off any product + free shipping until May 1. This is one of the most generous offers of any sponsor we’ve had. Did we mention they have a 2-week free trial? Go to https://www.liveouter.com/room to get the deal.

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They have a patented built-in outer shell cover to keep your furniture dry from rain and dew. It's the How Did No One Think of this Before product for me on the outdoor furniture front. I've absolutely loved it, and I know you will too. See the difference at liveouter.com slash room. And now through May 1st, you'll get $300 off plus free shipping. Again, that's live outer o-u-t-e-r.com slash room and get $300 off plus free shipping, only available to our podcast listeners. You're going to absolutely love it. Interested in investing in commercial real estate, but not sure where to start?

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and an upcoming IPO in Seattle. sign up for free at lex dash markets.com slash room and get a $50 bonus when you deposit at least $500. What is up? How you doing, man? Good to see you. Good to see you. I feel like it's been, I feel like it's been a week or two since we've gotten on one of these. So I'm glad we're back. Totally.

I've got a list. Yeah, you got a list? I've got a list, man. I mean, well, first off, since we last recorded, the world has. exploded, you know, in a lot of ways, in a lot of tragic ways, as I'm sure everyone is well aware at this point with everything going on in Ukraine and Russia. A few things related, you know, on the kind of more of the business side of that that I was hoping to chat through today. But I had an interesting conversation last night that I want to start with because I just thought

it was like, I don't know, it's kind of random, but it was pretty interesting. I have this close friend who he worked. works right now at McKinsey. And he's really like an entrepreneurial guy. And he, you know, previously founded a business. He probably wants to found another business. He's like deep down the crypto web three rabbit hole. And I was asking him like, dude, why the hell are you at McKinsey? Like, what are you doing? And he was trying to explain the rationale to me of, you know, it's like a high paying W2 job. And it made me start thinking about. And like the analogy I gave him was you as a person. And I'm curious for your perspectives on this.

It's like you as a human being, imagine yourself as like a pile of cash, like a million dollars of cash. You're just a pile of cash. And it's not always that you find the like perfect thing to invest that cash in, like to invest your resources in. And so sometimes you need to find the like high yield savings account to store that cash in while you're waiting to find the big opportunity. And so I presented that to him as like, that's what you're doing.

McKinsey in this case in your life right now is like the high yield savings account. Like you're getting a return on your money. You're getting your W2 income. You're getting this like prestige. It looks great on your resume. But as soon as that thing comes along that you know is like a 10x like opportunity on that cash, the cash that is your life, you're going to like take it out of the high yield savings, wire it into whatever that opportunity is and let it rip and run.

And I thought it was such an interesting analogy when I put it together because I was like, it's really how I think about a lot of different opportunities in life. Like you need your kind of like storage place where you know you're getting yield and you know you're getting a baseline return so that you can wait and have the luxury of waiting for what those big opportunities are so that you're not just like constantly running between, you know, things that you think might be runaway opportunities. What do you think? Well, I think people romanticize entrepreneurship in general. So, and I think I see a lot of people who like jump into building when they have no savings and they get into debt. And it's actually, it's quite sad.

So I think like it's easy to knock on this like essentially McKinsey bro. But I think it makes sense. As long as he's spending his nights and weekends and he's actually like building stuff, launching stuff, nothing wrong with a paying, a high paying job. Yeah. It's sort of like find your, find your version of that high yield savings account. I mean, it's like, it's great. It's a great insulation sometimes in life.

And you can park your. cash like you as an asset there while you wait for what that thing is that grabs your curiosity and gets you so excited to jump into the next thing. It was just something I was thinking about, you know, like in real time last night when I talked to him. So I wanted to, I wanted to bat it around. But let's jump into the list. Yeah, yeah. It reminded me of like this concept of mailbox money. You know that concept? It's like making money that, you know, basically pays your bills, your lifestyle. And if you can do that automatically, like it comes in the mail.

And I actually set up this affiliate campaign that would provide me, you know, a few thousand dollars every month. And it's been going live for years. And it's actually the thing, the high yield savings account, basically, that allowed me to actually go and build a lot of the products I wanted to go build. So mailbox money is a cool concept. I've talked about that with Ndama Kong Su, who we have coming on the show soon, actually. He talks about it a lot in the context of athletes and how mailbox money is so important

because they're making this super high salary, but it really only lasts for a few years. And so deploying that salary into things that generate mailbox money for the rest of your life is a really good insulation from potential future disruption. I completely agree. It's like, you know, it gives you the flexibility to go pursue those high upside opportunities because you're not worried about the downside. Yeah, so there's one way to do it is get a job at McKinsey, high yield savings account.

Other way to do it is build some sort of passive income or mostly passive income product that just pays you. Yeah. The one thing about passive income that a lot of people don't talk about, like passive income has become this meme where like, you know, everyone on TikTok is like, here's how to generate $10,000 of passive income a month or whatever. The thing about passive income that I've found is like it's never quite as passive as you think.

there are very few things that are truly passive every now and then you know maybe you come across something or you've been very elegant in designing something but most income if you want to keep it going there's like more time involved than you think and so the other thing I would just caution people against is like the idea of passive income is almost like a misnomer in and of itself there's going to be some time and some at least like headspace allocation that you have to that you have to put towards it so be mindful of it as you continue to build totally dude we don't have a ton of time. And we've got a great guest joining us for part of the discussion. So I want to dive into our lists. I know you've got a couple things. I've got a couple things. You want to just jump

right in? Yeah. You lead us off. All right. So I've got a few things on my list. I want to start with crypto and Ukraine. And I don't want to wait into the territory of people trying to opine on military strategy or, you know, anything that's happening from a geopolitical context. But the crypto side of this is fascinating to me. And really what I'm referring to is the fact that crypto donations have been accepted by Ukraine and are flowing in and insane amounts into supporting Ukraine in this in this battle against Russia. And I think the most recent numbers I saw before we were recording was like something like $60 million of crypto assets, been raised. And like people had donated, someone donated it a crypto punk. Gavin Wood, the founder of

Pocodot, donated like $6 million of crypto. So it's this amazing show of force from the kind of Web3 and crypto community and coming together and supporting this. And it's so counter to the broader narrative of like crypto is for fraudsters, scammers, criminals, you know, degenerates, etc. So I'm curious for your thoughts on it. Well, I think, and it actually goes back to what we were talking about around passive income and active income, which is people just like to bucket things into one category. It's either active income or it's passive income. It's either for criminals or it's not for criminals. Everything's black and white.

Everything is black and white. And the reality is that everything lives on a spectrum. So what, you know, what I think the $50 plus million going to Ukraine has taught, you know, you know, mainstream, a mainstream audience is that the spectrum is now enlarged in a lot of people's brains. Now a lot of people are like, okay, like I, you know, yes, you can use crypto for bad, but you can also use crypto for good. And I think what this is actually going to do is it's going to inspire a whole set of entrepreneurs, next generation entrepreneurs who are going to be building crypto products or crypto companies that are social cause-based. So I'm pretty excited about that.

Yeah, it's really interesting. It's a great point you make. I mean, some of the stuff that's happening is just pretty inspiring, like broadly, just from the outside looking in, like, you know, even not being someone that's super involved in the community. I mean, you had, there is a Pocodot founder, which I mentioned, chain CEO, Deepak Thapti, Thapli. donated like 300k. There's this gaming company, like a Ukrainian gaming company called Holy Water that launched an NFT gallery from all Ukrainian artists. And I think they had raised like 40K by the time that I was checking it out.

There's literally like really amazing things. There was a Russian national actually living in the U.S. who recorded a video burning her Russian passport and was auctioning it off and donating the proceeds to the struggle in Ukraine. So I think it's just this amazing thing of like, you know, innovation kind of coming together with this situation where it's opening up new inroads to supporting people. I've seen people like paying for Airbnbs in Ukraine. I mean, using these different vectors to support people is just a really interesting thing that's happening.

I also just think, and I texted you this or texted our group chat this earlier, how crazy it is that I think Vladimir Putin is. probably the highest dislike to like ratio in human history. Like if you were to go, you know, there's seven billion people in the world or whatever the number is, if you were to go ask people like, do you dislike or like him? I think he probably has the highest ratio of dislikes to likes in history, which is like being the most unpopular human being in history is kind of wild. Yeah, it is wild.

I mean, well deservingly, for sure, I think. Yeah. What about what about the big tech? side of this. That's like the other side that's been in the news a lot is like how tech companies have responded and how business has responded in general and kind of pulling out of Russia. Like you've seen, you know, Apple announced they were closing operations within, within Russia. They don't have any Apple stores there, but they were shutting down, you know, sales through any kind of third parties. I think Google was stopping ads. Facebook actually got shut off by Russia because Russia.

claimed that there was misinformation on the platform, which is rich. You know, and you had TikTok, I think, just announced that they were going to shut down streaming in Russia because there were some law passed by Russia that said, like, fake news couldn't be disseminated on the platform. So TikTok shut off. There's all this, like, you know, reaction from the tech community. The cynic in me says, yeah, well, the ruble, you know, Russian currency is basically going to be worthless.

And so doing business there actually doesn't make sense. And so you can take the PR win of like, hey, we're not doing business. in Russia when the reality is you didn't really want to be doing it economically. But the optimist in me says it's great that the, you know, that the kind of tech and business community is coming together and rallying against this, you know, against a dictator to go do this. So what do you think? Well, first of all, I saw today that we work CEO is one of the companies that, you know,

he, I'm pulling up the quote, we work won't exit Russia where biz does quote unquote incredibly well. So, you know, theme of this episode is spectrum. And I think like you're also seeing people go on the other side of the spectrum and they're doubling down, which is, you know. I hadn't seen that, but I'm pulling it up now. That is crazy.

Do you know how many look? I want to look up how many locations they have because the same thing happened with, with McDonald's, which at least as of now, I think it has like 800. 47 restaurants in Russia. And I mean, they're refusing to close them. And I think, like, that would be a big show, right? I think it's like one of the most popular fast food chains in Russia. But McDonald's is keeping them all open.

A lot of them are company-owned as well. So they actually have control over them. Pretty crazy. Yeah. And it's like, it is crazy, you know? It's absolutely, it's bonkers. I imagine they're going to get enough pressure from the public over the next couple of weeks. if this situation continues, that it's going to be a lot more difficult for them to justify that.

I mean, we work. It's like, man, what are you doing? Like, with McDonald's, I'm, like, almost more sympathetic to it. But I still think they should shut them down and kind of, you know, continue to gather momentum around all of this. But we work. That's crazy. I was just pulling it up. It's, I mean, it's wild. So what do you have on your list, dude? That was the main stuff I wanted to talk about before we have our guest in. Okay, so new NFT project, Ty Lopez launches NFT project.

Did you see it? Who is Ty Lopez? He's like a motivational speaker, right? He's famous. I mean, I know he's famous, but like, what's he famous for? You may have just seen Ty Lopez because he used to, like, he basically had these ads on YouTube where he would be like, this is my garage and this is my Ferrari and this is my house.

And like, let me show you how like you can have this. And he would sell stuff, you know, courses. Okay. Okay. Now, fast forward to today is I think he, he runs a company that goes, it's like a P firm, basically. They go and they buy old brands like Radio Shack, et cetera, and they bring them online. I think he bought Pier 1 imports. I think he bought like the e-commerce business of Pier 1.

Yes. Okay. So that's, you know, Ty Lopez might be, you know, Vladimir Putin is the most hated man in the world. Tai Lopez might be one of the most hated people on the internet. Really? He's also really loved. Like he also has this like massive fan base of people that are obsessed with him, right? He's just polarizing.

He's polarizing. He's definitely very, very polarizing. And I don't know enough about like Ty Lopez. if you're listening to this, like, and I know you follow me on Twitter. So like, um, you know, nothing, you know, I don't know enough about the situation to be like, you're a bad guy or a good guy. But there is that perception around that he's kind of like a schemer. Well, that's like, dude, I mean, I don't know. I have a pushback to this because I think that is a broad perception that has been created around like online courses, online sales, you know,

anyone that's like marketing their skills to like teach you how to do something rather than doing it. There's like this broad-based perception against it. It's like Grant Cardone, Tony Robbins, Gary V gets shit for that kind of stuff. But like Ty Lopez has a million and a half subscribers on YouTube. Like you must be doing something right. And the thesis around buying, you know, dated consumer businesses, modernizing their e-commerce stack and, you know, kind of reviving them is actually like a pretty sound fundamental thesis around. business. Yeah, I think, yeah, no comment on Ty Lopez, good guy or bad guy.

What I wanted to comment about is his new NFT project. So did you see it? No, I haven't seen it. Tell me about it. I'm going to pull it up while you're talking. So it basically, it's called Original Garage. And basically what it is is you buy an NFT and you get to do things with Ty Lopez. So I pull, you know, I'm pulling up a tweet that I saw.

It's a, you know, from this guy, Eddie is Kongs. Hey, at Ty Lopez, legit question. Why would I pay 30 to 40,000 to watch a movie with you? Or 80,000 to 90,000 for your WhatsApp. Who do you think you are? You deaf have a shady reputation. And doing this only adds more fuel to the fire. I respect anyone wanting to add value to NFTs, but this is just not the way.

So he got a huge blowback from the crypto community. community around, you know, why you, um, selling, you know, these very expensive NFTs to go and hang out with me. And Faroak, Faroak, who's an amazing follow on Twitter, if you're not already following him, it's just Afrook. He's the founder of Rug Radio. He's really well known in the crypto community. And he, um, got in a fight with Ty Lopez on Twitter. And here's the tweet. Basically, well, basically Faroque was saying like, was kind of being like, this is very cash grabby. And then Ty Lopez tweeted, but if you buy my NFT, you can come to another one of my pool parties at Faroak.

And there's a picture in 2016 of Faroque and Ty Lopez at this party. So a lot of drama in the crypto, Twitter space. What do you think? I have a lot of thoughts here. So I don't know Ty Lopez at all. I think he follows me on Twitter. I get, you know, like there's a lot of general animosity towards like people that have made a lot of money selling courses and, you know, talking on the internet, etc.

I don't know anything about Tai Lopez. I've never watched any of his videos. That plus there is a lot of animosity in general towards cash grab NFTs, right? Like the, the NFT boom that happened. in the like earlier days of NFTs you know like kind of earlier part of 2021 that precipitated a bunch of people to do these like there were cash grabs lots of cash grabs and I feel like now we're kind of into a place with that nfti landscape where at least for me I don't see as many things that I'm like wow there's nothing to this most of the NFT stuff that at least I'm hearing about or

that's like generating buzz it feels to me is more unique like at least has some edge there's some road map there's something interesting about it or like brands or trying to drive interesting extensions or work on things. It feels more like an idea laboratory to me now than like a cash situation where people are just trying to make money. And so I think this situation is like it's a collision of two really hot button issues. Like one being, you know, Ty Lopez's perspective, reputation, you know, around like how he's made money and what he's done, which already people have animosity towards, as you pointed out. And then the other being, you know, NFT cash grabs and people perceiving the like collision of these two things is a very, very, you know, it's a combustible situation. And so I can see why this would be a situation that would have that. And I'm like, you know, I'm looking at some of the, some of the kind of tweets that have come out against it. Like there's ox beans. I don't know if you follow him. Zero X underscore beans. He said like he pulled up the code base from it. He said hilarious. The Thai Lopez NFT immediately cyphithe. offens out the funds into their team's wallet when you mint, just so they can scam your eth just a little bit faster. So it seems pretty clear that there was like a lot of pushback

and blowback within the, within the NFT and crypto community broadly towards this. And I think, look, sorry, my final thought on this is it behooves the crypto and Web3 community, the like real believers who are going to be here for the next 10, 20, whatever years to police this kind of stuff. internally if they perceive there to be, you know, rug pulls, scams, any bad behavior, because anything that you can do to weed out that behavior and police it is helpful towards building a reputation of, you know, more legitimacy around this over time. And everyone knows there's still this negative reputation around crypto Web 3, as we talked about in the context of the Ukraine and Russia donations.

So any, like, it's encouraging to me to see the crypto and Web 3 community policing things that they perceive to be below bar. Yeah, and I'm happy you said that. I think, like, you know, one of the things in this, in this NFT collection is, you know, I think the gold pass mince for between 80 and 100, you know, that's, which is, you know, a couple hundred grand, just for access to this NFT. And, you know, I think there's, that's a lot. And that's exactly why a lot of the, there is a lot of blowback from a lot of these projects.

Because, you know, you could buy this thing for 260 grand. And then three months later, Ty Lopez could be off to the next shiny object. So we're seeing that a lot a lot right now from the NFT community, which is high mint prices are big faux pa. So interesting to see. we'll see, you know, who knows? Maybe Ty Lopez ends up making this like Gary VU, like a V friends, and it ends up being an amazing collection. Or maybe, you know, we come back in 12 months from now and it goes to zero.

Yeah. What's your guess? And you can be honest. I don't know. It'd be great to get Ty on the show someday and ask him these questions directly. But if we don't, that's fine. So give your honest take. I mean, if 97% of NFT projects go,

go to zero, it's just more likely that this project goes to zero. Yeah, the base rate is pretty bad. That's true. I don't even have a percent. Like, I have no perspective on whether it goes to zero, whether it's valuable. But looking at it, it certainly feels sort of absurd. The flip side is like, if there are people that want to hang out with him that much, that they're willing to pay that much in U.S. dollars, it's kind of the same thing. I just don't, I mean, like, Warren Buffett auctions off a lunch with Warren Buffett every year. It gets donated.

Warren Buffett does not need, you know, a few hundred grand or whatever it costs, but I need to pull it up. I think like, I think a crypto person paid like a couple million dollars to do the lunch with him one year. And it regularly goes for like many hundreds of thousands or into the millions of dollars to have lunch with Warren Buffett. Warren Buffett, much more fucking impressive than Ty Lopez. No offense, Ty Lopez, I just, it's Warren Buffett. Like, I kind of get it. And Warren Buffett is auctioning it off. But this type of thing generally exists where people, you know,

auction off time with themselves in order to go do something. I just think it's typically someone that's like made a ton of money and they're donating the proceeds to charity versus putting it in their pocket. If I was, if I was Ty Lopez, I wouldn't have created such a big collection. I think it's like 8,600 or something like that. and I would have just focused on like 300 people. Like his odds of success would have been way higher if he just would have taken the club CPG model,

crypto packaged goods by our buddy Chris Cantino, which basically he minted 300 of them. He created a telegram group at, you know, he's in there 8, 10, 12, 14 hours a day. He's like the community leader. He's doing all the right things. And now the floor price is like 12. 1269 E, he's adding value. That's what I would have done if I was tied.

I just started 300 and then added as time went on. Yeah, and if I were, I'd probably flip it and just have all proceeds donated to Ukraine at this point. Like if he wants to have any hope of reviving this situation, I feel like that's got to be the, that's got to be the move at this point. But yeah, I mean, the Warren Buffett thing, by the way, I just looked it up. The last one sold for $4.567 million. Justin's son, the crypto, the Tron guy, bought it for $4.6 million. I think he wasn't actually able to attend it.

In the end, there was some whole thing. But the year before that, it went for like $3.3 million. So there's definitely a massive market for the Warren Buffett charity lunch. But I don't think Tai Lopez is quite on the same level as it. And to me, it looks like a cash grab. Cool. You know, it's like the duck test, man. If it looks like a duck and it quacks like a duck, it's probably a duck.

That's kind of how I feel about it. So I'm open to being proven wrong, but I don't think I am. Interested in investing in commercial real estate, but not sure where to start. Me too. Well, Lex has created a new way for you to invest in real estate. Lex turns individual buildings into public stocks via IPO so you can invest, trade, and manage your own portfolio of high-quality commercial real estate. Any U.S. investor can open a Lex account, browse opportunities in various asset classes

such as multifamily and office buildings, and buy shares of these individual buildings. Lex opens up direct and tax advantage ownership in an asset class that has previously been inaccessible to most investors. Get started today and explore Lex's live assets in New York City and an upcoming IPO in Seattle. Sign up for free at Lex-Markets.com slash room and get a $50 bonus when you deposit at least $500. 93% of your life has spent indoors, but so many of our best moments are outdoors. That's why I'm so excited to share with you Outer. Outer makes the world's most beautiful, comfortable, and durable outdoor furniture.

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See the difference at liveouter.com slash room. And now through May 1st, you'll get $300 off plus free shipping. Again, that's live outer, o-u-t-e-r dot com slash room, and get $300 off plus free shipping, only available to our podcast listeners. You're going to absolutely love it. I think we have a guest coming up, don't we? Yeah, so we have, and we'll let him in once he gets on. But I'm super excited to have this discussion because I've been wanting, as you know,

and one thing that's been on my list for a while, to talk about future of work, talk about the return to the office, return to work, how different companies are managing it, you know, how the market is going to decide whether fully remote or fully in person or hybrid is the right model and what works best for startups, for big businesses, etc. and I couldn't really figure out who the right person was to have the discussion. And then it came to me when I read this Wall Street Journal article about Matt Mullenweg, who I think you know or you've met at some point in the past. But Matt, you know, he was actually the creator of WordPress.

So he's like an open source OG, has been around for a while as like an amazing entrepreneur. And now he's the founder and CEO of Automatic. And the companies, I don't know, it's why. What, like a multi-billion dollar company today has grown incredibly, but I recently saw this article that was entitled, this CEO lets his employees work whenever they want from wherever they want. And it was like the future of everything section in the Wall Street Journal. And so I just realized this is the guy we have to have on to have a discussion around this. Yeah, absolutely. I'm excited to chat with him. I met him many, many years ago. So we'll see if he

remembers me. Yeah. He's, I mean, he has an incredible. incredible background. I actually, looking it up, automatic is actually the company behind WordPress. So it's not like some new iteration.

He's continued building off of that open source foundation. Yeah, I think what I'd love to learn from him is, you know, he's been doing remote since before remote was cool. And I know that he's got a lot of like processes in place for meetings and just running a smooth,

you know, operation. So I think a lot of us listening, you know, and I run a remote company and I'm always trying to figure out how can I make it, you know, as as fun as possible and is, and yeah, and I know that he's done that successfully. So I'm here to learn. Yeah, it's, it's such a hot button issue right now, too. They'll return to work and how people are thinking about it. Like there's, it definitely feels like this black and white camp of, you know, if you're not back in the office, you know, you're dead. Like I saw Keith, Keith Rabeoy, you know, Founders Fund and, you know, amazing entrepreneur investor tweeted out this morning, you know, in response to a tweet saying that startups, someone tweeted startups that buck the trend and commit to in person are more likely to hire great young talent.

I'm seeing talented young engineers say they are, quote, done with remote. And Keith responded true, replied back to it in his typical punchy fashion that he operates on Twitter. So I thought that that was an interesting backstory to it too. Yeah, amazing, first of all. Amazing response. Oh, what's up, Matt? Hey, Matt. What's going on? I'm doing pretty well. Thank you so much for having me today. Where are you joining us from? Actually, Houston, Texas. Nice. Nice. So you haven't hit quite the like swampy summer months yet within Houston. No, it's chilly, rainy, and cold. Oh, man. Well, thank you so much for making a few minutes of time. I know you're busy and have a ton going on. And the world is in a lot of flux right now. So really appreciate it. You know, this is super casual. We don't consider this an interview show by any means. We really just like to have amazing people like yourself come on and join us to jam on interesting things. And so one of the things we've been talking about a lot has been the future of work, right? Like what happens?

upon this like reopening of the world that it feels like we've been talking about now for two years, by the way. And finally, maybe now we're starting to get to it. But I first came across you in this Wall Street Journal article that you're probably been sent a million times that was talking about your perspectives on where the world is going. And it was talking about how you let your employees work asynchronously from wherever they are in the world. Can you just start maybe by giving us like a little bit of background on where that ethos came from. Like Greg pointed it out, you've been doing remote since, you know, way before remote was cool and in vogue. So we'd just love to get your perspectives on like where that ethos came from and, you know, and how it's

kind of played through the automatic story. Yeah, sure. So the company I'm a CEO of is called Automatic. But we were born, Automatic was born out of an open source project called WordPress. That lives at WordPress.org. It's all volunteers. And like, many open source projects, it was developed online from people all over the world. So myself and the co-founder had never met in person. He was in the UK. I was in Houston, Texas, where I am today. And that was actually not new for open source. If you look at the Linux kernel or Mozilla or all these sorts of things, they were typically a passion, a community is a passion that came together from everywhere. So although that was new for companies, and we got a lot of questions.

back once I started a company in 2005, 2003, when WordPress started, open source had been doing this for 15, 20 years. So it felt very natural. Yeah, it's sort of like the, you know, when people point out the like evolution of the internet and everyone talks about Web3 now, it's kind of like what's new is also old because, you know, the Web 1 ethos of all the open source protocols that were developed is very much the ethos of what we're talking about today. It's just there's new, you know, adaptations of it in this in this new world. So it feels like this is kind of the natural extension of that as you talk about it. I think so.

Matt, did you ever have a, did you ever have a stint in San Francisco? Was there ever a point where you moved the company in San Francisco? Because I do remember a presence, a big automatic presence, like on the bay somewhere. Yeah. So my story, I had gone to University of Houston. for two years and then a company called CNET paid me to drop out, move to San Francisco in 2004. So this is about a year, year and a half after WordPress started, but about a year before I had found the company. And definitely, you know, part of founding the company was going out there.

It was amazing for me to meet people and be influenced. And like, San Francisco is definitely where my tribe was, you know, people who are passionate about building the web, passion about technology. So I still love San Francisco. I think I'm the last one. Like I spend time there. My mom's out there right now. I actually really love San Francisco. So and we at first had like a desk in our investor's office. So true ventures had a spot on Pier 38. You know, Instagram was upstairs. There was a fun spot. And and then later that expanded office next door came available. So we had it. But it was always like a lounge. Like we've never actually ever done permanent desk or places, but we did want a place for people to get together and to host community events and do WordPress meetups. And so,

I'm a big believer in in person and physical space. A big part of automatic culture is actually meetups where we bring either the whole company or teams together a few times a year. But it just felt like the best, most talent in the world was not in San Francisco, regardless of all the smart people was meeting. It felt like a very small pond efficient. So we were trying to compete. So we were trying to compete with the Googles and Facebooks of the world. Like we had to fish in the ocean, not the same pond they were fishing in. So by redefining the game, particularly in hiring talents, it allowed us to flourish, even though we had much less funding and, you know, typically made a lot less money than

these other companies, especially in the early days. How do you think about scaling the kind of serendipity that comes from being in a location? And I say that in the context of San Francisco because I think part of the glory days of San Francisco, if you will, there was this amazing vibe of serendipity where you could walk out on the street and you'd run into the person that you ended up co-founding your next business with because there was just this like incredible entrepreneurial vibe energy. I was at Stanford and I was kind of at in school during those years. And even after when I started working, going to the gym, like you just run into these amazing. entrepreneurs, you know, investors, founders, et cetera. How do you do that? Like, where is the serendipity in this more remote or hybrid world?

How do we find that? Twitter? You know, like, you know, the exchange of ideas. Now, there is something to be said for, like, your kids going to school with someone else. Or like, that is cool. But I think for the, like, exchange and debate of ideas, that moved online. 10, 15 years ago, you know, because through blogging at first and then micro blogging with Twitter and, like, all these other things, like, that was where the ideas were

shared and debated and everything and where the fun was. And so now, like, even, like, I'll go to dinner in San Francisco, and people are talking about the essay they read online. They're not talking about what, you know, Mark Andreessen said to them at the gym. They're talking about the thing he posted or the new article everyone's talking about. The latest newsletter. That's what's, I think, pretty exciting about it. The latest podcast, like we're on right now, you know, that you don't have to be in San Francisco to listen to this. I do have a confession to make.

So many years ago, I met you actually at a jazz show. Oh, cool. So I met you. In SF? So I was living in Montreal at the time, and you were there for the jazz festival. I presume. And I met you and it was like the first time what you were one of the first people that I, you were like I was, you know, I live in San Francisco.

I work on this thing called WordPress. I knew about it. And that serendipity actually happened. And actually what ended up happening is you, I think you might have introduced us to someone on your team. We ended up doing, we ran an agency. And we did, we helped some companies actually move from their custom CMSs at the time to WordPress. Awesome.

And one of the projects was TechCrunch redesign. I don't know if you remember that project. And we worked on it. And that actually is what put our agency on the map, which helped put me on the map, helped like steamroll my whole life. Awesome. So that. What a cool thing.

Yeah. So, well, like, so I believe in the serendipity of the internet and I also believe in the serendipity of like in person. Like what are the odds, you know, it's all about, I think and, and, you know, I'd love your reaction to this. It's all about like increasing your probability of, you know, these encounters to happen and these encounters can happen in San Francisco today or a jazz show in Montreal, but could also happen on the internet. internet. So, you know, what advice do you have for people who want to increase serendipity? Say yes. Go to parties. Go to events. Go to conferences. Go to jazz festivals. I actually used to spend every summer in Montreal because it was an amazing city. It still is, I think. And they had the jazz festival just for laughs. The something Foley, I think there was like a French festival. It was just an amazing city to be in. So I'd always rent an apartment there for like a month in the summer. But we also, you know, a big part of the WordPress ethos is something called WordCamps,

which are community organized. So that was also a reason I went to Montreal. So inspired by Barcamp, which I was kind of a co-founding associate of. We said, hey, here's a template for running an event. Do it wherever you want. Just follow these rules, make it free or cheap. And there's been hundreds and hundreds of these in cities around the world. And I actually, early on, I used to go to every single one because I was like, if someone's going to do a conference about WordPress, I'm getting on a plan and go in there. So I fly hundreds of thousands of miles per year, go to every single one. And that was part of bootstrapping our community. So that's, I think you can, you know, like fortune favors the prepared, serendipity favors folks who are out there and meeting folks outside of your normal circle.

You just have to balance that, I think, also with, you know, deepening the relationships with the people you care most about. And that was probably what I didn't do as well in my 20s in particular is because I was always on a plane. And so when I go back to San Francisco, my friends would be like, oh, you're in town? Sorry, we didn't know. I write about this a lot. I actually recently wrote a piece about how to, I mean, I call it expanding your luck surface area or like expanding your serendipity surface area. I love that. Like you can actually, I kind of think.

there's two types of luck. There's like the very pure and raw form of luck, which is things you truly cannot control, you know, where you're born, who you're born to, the kind of like baseline level of circumstances that you are given, which is totally out of your control. And then there's this more like amorphous, fluid, impure form of luck, which is really the result of these like thousands of daily micro actions that result in this macro thing that we call luck. And I think about it in the context of, have you ever seen Interstellar? Yeah. Have you guys seen that movie, the Matthew McConaughey movie?

And so in that movie, there's this scene where they're talking about that tiny little planet that was next to the black hole and how they're talking about the lack of life on that planet. And there was a concept that they talk about, which is basically that it's very low likelihood that a planet right next to a black hole can have life. And it's because the black hole sucks up all of the lucky events. that could have struck the planet and been the seeds of life, like the random collisions, the chaos theory,

the asteroid that has a seed of life on it, etc. The black hole just sucks all that up. And I think about that a lot in the context of my own life because so much to me of getting lucky is just getting rid of the black holes that are in your life, like negative people or pessimists who are around you, like all of those black holes that are kind of the anti-luck. And then also just expanding your own surface area,

like opening up your aperture so that all of those lucky things can strike. And to your point, Matt, like saying yes to things, saying yes to everything in your 20s, is a great way to do that. You can't get lucky watching Netflix on the couch at home. You can if you go out and you meet people or even if you're in a discord and you're engaging with people in good faith, you can get lucky doing that. And so it's like deliberately taking actions that expand, open the aperture, expand your serendipity surface area, feels like the path to going in.

and kind of making your own luck, as it were. I love that. I'll have to check out that essay. And how cool that that's an essay. And I think even of people that we now think of the very top of their game, use online to connect with others. You know, like, it's kind of funny. When I first moved to San Francisco,

I was introduced to Mark Kendrescent to invest in automatic. But at the time, this was before he had written his amazing blog post. He hadn't really, like, had his blog. And so I viewed him totally wrongly as more like an Internet 1.0 guy who was like, didn't really know what was going on. But wait, I was totally wrong. And later, once he started publishing, I was like, wow, this person is a genius, you know, like, what would Andreessen Horowitz be without Mark's seminal essays and Ben's amazing books and essays?

You know, like their writing is part of how they disrupted the VC model and became Andreessen Horowitz, which now would take for a minute. Remember that they were like newcomers to the scene. It is a great point. You know, writing in public, sharing in public, sharing your ideas and insights is such a powerful way to go, you know, attract growth and luck in these opportunities. Because if I'm sitting, like I'm sitting here recording this from my house in New York, in the New York area, I kind of like, my reach physically is very small. It's like this room, right? But with the internet, my reach is literally global. And if I put ideas out there, even when I, you know, when I started sharing on the internet,

I had zero followers and I just started sharing and you kind of develop it consistently. It starts growing. You're like casting this net of magnets out into the world that, you know, with your ideas, with your insights, with whatever you're sharing that really can attract millions, you know, billions of people at scale who can come and find your ideas, be attracted to them, maybe be repelled by them and push the other way. but you're really casting out into the universe in a much more kind of vigorous and broad way than was ever possible in history. The best hours I have spent in my entire career are those writing and publishing.

And I'll pitch WordPress here too. Have your own site. Yeah. You know, if it's a medium essay or something like that, people just remember that was on medium. They don't remember your design, your name, your everything. So it's really nice to have a differentiated presence online. line. Yeah, right before this, we were talking about Keith Rabei had this tweet, or he was just talking about how, what was it, Sahel, like, basically someone had tweeted, you know, that

startups were starting to buck the trend and commit to more in person and that there were like a lot of talented young engineers who were saying they were done with remote. And Keith responded saying he thought that was true. And so Greg and I were chatting about that, kind of having a debate about it. Like, is it true that young people are going to buck the trend of remote, you know, and why? Like, is that going to happen or not? And, and my, my pushback to that whole, like, energy is, it, the core assumption there is that it's very, first of all, it's a very U.S.-centric point of view. So not everyone has the ability to apply for a job, move to San Francisco, go work in Miami.

You know, we have a lot of listeners in India and Nigeria and Kenya. These huge opportunities aren't just as readily available to walk into these doors and apply and start working. So I think writing is such a great way just to attract opportunity. And just building, right? I mean, for engineers, your code is your code. and it's a universal language. And if you're building and developing amazing things, you will find amazing opportunities in this era.

I think it's fundamentally changed, right? It used to be very much the case that talent was evenly distributed, but opportunity was not. I think we're slowly moving towards a world, and we're not there by any means, but we're slowly moving towards a world where opportunity is evenly distributed and that if you're a kid born on the street in India,

but you have the internet, and you teach yourself to code or to develop or write, you'll have as many opportunities as a kid, you know, born in Greenwich, Connecticut that goes to private school and gets into Harvard. And I think that's a noble mission that we should all, you know, be in favor of, you know, a world where everyone has kind of equality of opportunity. You know, I'm a capitalist. And so I am all for unequal outcomes because I think that, you know, performance and doing well, like you should be rewarded for outsized performance. But equal opportunity with unequal outcomes.

And I think companies need to evolve to take advantage of that new global landscape. So something we didn't do when we started, but we switched in like 2012, 2013, was paying the same salaries regardless of geography, right? It's the same work. It's the same job. You're creating the same value for the company and the customers. So you should make the same pay. Guess what?

That's an amazing innovation, actually. I don't know if you saw this, Matt. There was an article in the Atlantic, maybe like two, three weeks ago that was all about, tech companies trying to do the like geographic discrimination on pay you know like someone in san Francisco would move to Nashville or move to Boise and the companies would cut their pay and that was like the original assumption of big tech post right when COVID happened and then I think a lot of them got a ton of pushback to it now they're adapting to it by saying like you're not going to get the same pay increases so you're not going to get cut down but you're going to have less opportunity to accelerate and

grow because there's going to be like pay bans based on where you live. And I agree with you. I just feel like it's a very myopic view of the world and of kind of how we're developing as a society. Great. I hope they do that so we can hire more people. But also think about it that if you're like let's say you're hiring out of India as an example. If you're going to pay the global rate, you're going to get the very best people, the most connected, et cetera, in that country. Maybe if Keith company, Keith's company is not, he's not going to get the best person out of those countries. And I think in the War for Talent, it's not about in office as the future or distributors the future or anything. I think it's about giving people the choice and the autonomy.

So at automatic, you can work wherever you want in the world or you can work in San Francisco too. If you love that environment, go. Great. By all means, move to San Francisco. If you want to work from home, great. If you want to go to an office, guess what? We have a co-working stipend. we'll give you $250 per person per month to go to a we work or a coffee shop or wherever you want to go. So you can be around that energy. You can go to Miami and be at the same co-working space as these companies if you want. That's fine. So it's just about giving that choice.

That's where I think people really thrive because some people do want to be in an office environment. They can work for automatic and make an office environment. We allow people in the same cities to pool together. So, again, pre-COVID, people in the same city. would often like get together once a week or something, have lunch. That's all things the company can support. It's not like, it's not like some, you have to choose one way or another and that you're waited to that forever. You just have to listen to your people. What do they want? The cool thing about a lot of this too, what you pointed out is the market will decide, right?

There are going to be companies that do this. There are going to be companies that say, no, you have to be back in the office five days a week and work, you know, synchronously and the old way, you know, the kind of industrial era style of work. and then there are going to be companies that, like, automatic, you know, take a much more forward-thinking perspective on it, and the market will decide, you know, that the best talent will flow to the places where they want to work, where the environment is what they want to work in. And the companies will either do really well or they won't. And we'll know, you know, in the next five, 10, 15, 20 years, we'll know what the future of work looks like because the market will determine it in a lot of ways. You know, talent can vote with their feet, as it were, which is a really cool thing, I think. By the way, we're talking about companies like their monoliths,

but it could also be within teams or divisions within a company. We're 2,000 people now. We heard 700 last year, by the way, so you can scale this quite a bit. If a team wanted to be in person or get an office, I'm fine with that. That's an experiment we could run. And maybe it could sort out. Maybe there's already 10 people living in a city and they want to go into an office every day. Sure, they can try that.

That's what they want to do. I'm not like religious about these things. It's about getting the work done and serving customers. It's not about how we got it done. How do you think about time zones and time zone working? A lot of people have teams where they'll have, you know, some people in Europe, some people in East Coast, West Coast. I know some companies like Shopify will basically create teams remote but in certain time zones. So, you know, only EST, PST, but they don't care where you live.

how do you think about time zones and synchronous versus async? I think for teams, it's good to be in a range. I'm actually okay with a range of up to seven or eight hours. So like Europe and U.S. is okay. Because you can still overlap for an hour or two a day, and that's usually plenty. If you need a lot more, you're probably having too many meetings. But we did make the mistake and no longer put teams that are spread across, you know, kind of like Asia-Pacific, Americas, and,

European time zones because that's just bad for everyone. But I think it's great for a company to have that. Because by the way, that makes 24-7 coverage way easier for things like support or systems or anything you need responsiveness in 24-7 coverage of, which every business at scale does for certain things. It's fantastic to be international. It's been actually, for example, we acquired a company called Tumblr that was primarily in the New York and actually Richmond region.

And a big thing we've been doing is trying to increase the reverse. responsiveness of their support by hiring more folks internationally. They would develop much bigger cues on weekends and outside of the U.S. East Coast time zones hours. And so that also meant that bad guys would start to take advantage of the eastern hours. They knew that there would be longer response times. They did things in the middle of the night in New York. Can you talk about Tumblr?

Can you talk about Tumblr for a second? I was like a Tumblr kid. So when I, you know, I saw that you all bought, bought them. I was just excited to see that, you know, some TLC was going to be put to that platform. So I'm just curious. Is there anything you can share around why you bought Tumblr and why you, and maybe some plans of where you're taking it? Well, one Tumblr is really cool.

It's social blogging done right. So it's got the best of a social network and the best. to blogging. It is majority, so 55% under 24 and under. So it's a young blogging network, which is neat. It's different than WordPress's demographics. It's primarily mobile, 85% on mobile. It's still doing tens of thousands of sign-ups per day, very active. And it's actually the, I think, the queerist social network. It's about at least a quarter, LGBT plus. So it's a really fun creative space for art and artists. And we took it to turn. it around. And actually, you know, some news as of February 1st, I'm running it personally. So I'm day-to-day,

running Tumblr as CEO, working on the product, working on the design, working on the tech, working on everything. And so hopefully we can accelerate the pace of iteration and be something. If you haven't used it in a while, I strongly encourage you to check it out, reinstall it, and try it out again. It still has a purely chronological feat. So we need to make that an onboarding experience better. But when you get your feed dialed in, it's one of the funest places on the internet. So before we let you go, Matt, I'm curious to just get your perspective. You know, the CEO of a massive, you know, multi-billion dollar company now, which you've grown super fast from a team perspective. But you're not a loud, showy, you know, jump up on stage,

pound your chest type guy. You haven't been to karaoke with me. That's true. I'd love to go to karaoke with you, actually. We'll do that sometime. I will come visit Houston. We'll do that. I've actually been to a great karaoke place in Houston that I'll send you.

But you don't strike me as that type. Can you just give us a couple of like your kind of realizations or lessons on leadership that have allowed you, you think, to be successful or what you've learned along the way, maybe that you've changed your mind on? as it comes to leadership. Yeah, I know we're at time. But I guess the main thing is that I am not like the rah-rah run around on stage CEO. And I used to really try to change myself to be.

And it just didn't feel natural, didn't feel authentic. But that's the whole point of an executive team is you can hire people who are great at the things that you're not. So as you grow your team, your company, you know, I've had specifically looked for folks who are maybe a bit more. outgoing in that way or a bit more like certain in how they talk about things where I might be like a little more soft-spoken or nuanced or academics sometimes in my speech so yeah just look for that and just but do you it's a great realization so when I tried to change it wasn't as good it's a great one I apologize I got to run thank you so much I'm a meeting yeah no I appreciate it I thank you so much for joining us join our free community at t rw iH dot com

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