How to Engineer Serendipity | Matt Mullenweg, Automattic

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2:12what is up how you doing man good to see you good to see you um i feel like it's been i feel like it's been a week or two since we've uh gotten on one of these so i'm glad we're back totally what uh 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 um as i'm sure everyone is well aware at this point with everything going on in in ukraine and russia and um a few things related you know on the

2:47kind of the more the business side of that that i was hoping to chat with chat through today um 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 um he 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 3 rabbit hole and i was asking him like dude why why the hell are you at mckenzie like what are you

3:20doing and he was trying to explain the rationale to me of um you know it's like a high-paying w-2 job and it made me start thinking about and like the analogy i gave him was um you as a person 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

3:54cash 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

4:22and 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

4:52like jump into building when they have no savings and they get into debt and it's actually it's quite sad um so i think like it's easy to knock on this like essentially mckinsey bro um 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 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

5:32is 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 um wait 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 like lifestyle and if you can do that automatically like it comes in the mail and i actually set up this affiliate campaign um that would provide me

6:10you 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 mailbox money is a cool concept i've talked about that with um nadam kong soo 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 like super high salary but it really only lasts for a few years and so deploying that salary into things that generate mailbox money

6:43for the rest of your life is you know a really good insulation from potential future disruption um 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 one way to do it is get a job at mckinsey high yield saving 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

7:15is like here's how to generate ten thousand dollars a passive income a month whatever the thing about past 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

7:44and 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 um totally dude we don't have a ton of time um and we've got a great guest joining us for part of the discussion so i want to dive in to um dive into our lists i know you've got a couple things i've got a couple things um you want to just jump right in yeah let's you you lead us off all right so i've got a few things on my list i want to start with um crypto and ukraine

8:14um and i don't want to wade 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 um 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 um into supporting ukraine in this in this battle against um against russia and i think the most recent numbers i saw before we were recording was like something like 60 million dollars um of crypto assets had been raised and like people had donated someone donated a crypto punk um gavin

8:54wood the founder of polka dot donated like six million dollars of crypto uh so it's this amazing um show of force from the kind of web 3 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 and

9:35everything'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 dollars going to ukraine has taught 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 to for good and i think what this is actually gonna do is it's going to uh inspire and a whole set of entrepreneurs next generation entrepreneurs who are gonna be building

10:14crypto 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 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 um there is uh polka dot founder which i mentioned uh chain ceo um deepak dapi thapliyal um 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

10:55they had raised like 40k by the time that i was um that i was checking it out there's literally like really amazing things there was a russian national actually um living in the u.s who recorded a video burning her russian passport um and was auctioning it off and donating the proceeds to the uh to the struggle in ukraine so i think it's just this amazing thing um of like you know innovation kind of coming together um with this situation where it's opening up new inroads to to supporting people i've seen people like paying for airbnbs in ukraine i mean using these different vectors to support people is is just a really

11:32interesting 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 i think vladimir putin is uh probably the highest dislike to like ratio um 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 well

12:06deservingly uh for sure i think yeah um what about what about the big tech side of this um that's like the other side that's been in the news a lot is like how tech companies have responded and how business um has responded in general and kind of pulling out of russia like you've seen you know apple um 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 um because russia claimed that there was misinformation on the platform which is

12:45which is rich um you know and you had tick tock i think just announced that they were going to shut down streaming in russia um because there was some law passed by russia that said like fake news couldn't be disseminated on the platform so tick tock shut off there's all this like you know reaction from the tech community the cynic in me says um yeah well the ruble the 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

13:15doing it economically um but the optimist in me says it's great that the you know that the kind of tech and and business community is coming together and rallying um against this um you know against a dictator to to go do this um so what do you think well first of all i saw today that um wework ceo uh is one of the companies that you know he i'm pulling up the quote wework won't exit russia where biz does quote-unquote incredibly well so you know the theme of the theme of this episode is is spectrums and i think like you're you're also seeing people go on the other side

13:55of the spectrum and they're doubling down which is uh 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 um with mcdonald's which at least as of now i think it has like 847 restaurants in russia um and i mean they 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 uh but mcdonald's is keeping them all open a lot of them are company

14:25owned as well so they actually have control over them um pretty crazy yeah and it's like it is crazy you know it's it's absolutely it's bonkers i imagine they're gonna get enough pressure from the public over the next couple of weeks if this situation continues that it's 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 um we work that's crazy i was just pulling it up it's i

15:02mean it's it's wild um so what do you what do you have on your list dude um that was that was the main stuff i wanted to talk about before we have our guest in okay so new nft project um tai lopez launches nft project did you see it who is ty lopez tyler looks like a motivational speaker right he's famous i mean i know he's famous but like yeah what's he famous for you may have just seen tai 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 and this is my house and like let me

15:38show you how like you can have this and he would okay he would sell stuff you know courses okay like that now fast forward to today is i think he he runs a company that goes it's like a pe firm basically they go and they buy uh old brands like radioshack etc and they bring them online i think he bought pier one imports i think he bought like the e-commerce business of pier one yes okay so that's you know tai lopez might might be you know vladimir putin is the most hated man in the world tai lopez might be the one of the most hated people on

16:18the internet uh really and 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 he's very very polarizing um and i don't know enough about like tai 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

16:53push back 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 um to like teach you how to do something rather than doing it there's like this broad-based perception against it right it's like grant cardone tony robbins garyvee gets [ __ ] for that kind of stuff um and but like tai lopez has a million and a half subscribers on youtube like you must be doing something right um and the thesis around buying you know dated consumer businesses modernizing their ecommerce stack and you know kind of reviving them

17:28is actually like a pretty sound fundamental thesis around business yeah i think uh yeah no comment on tai 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 gonna 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 um with tai lopez so i pull you know i'm pulling up uh a tweet that i saw it's a you know from this this guy eddie is kong's hey at tai

18:10lopez legit question why would i pay 30 to 40 000 to watch a movie with you or 80 90 000 for your whatsapp who do you think you are you def 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 blow back from the crypto community around you know why you um selling you know these very expensive nfts to go and hang out with me and faroq faroq who's an amazing follow on twitter if you're not already following him it's just apharoc

18:49um he's the founder of rugradio he's really well known in the crypto community and he um got in a fight with tai lopez on twitter um and here's the tweet um basically well basically faroq was saying like was kind of being like this is very cash grabby and then tai lopez tweeted but if you buy my nft you can come to another one of my pool parties at faroq and there's a picture in 2016 of faroek and and tai lopez um at this party um so a lot of drama in the crypto twitter space uh what do you think i have a lot of thoughts here so i i

19:32don't know tai lopez at all i think he follows me on twitter um i get you know like there's a lot of um general animosity towards like people that have made a lot of money selling courses and you know talking on the internet et cetera and i i don't know anything about tai lopez i've never watched any of his videos um that plus there is a lot of animosity in general towards cash grab nfts right like the um the nft boom um that happened in the like earlier days of nfts you know like um kind of earlier part of 2021 that precipitated a bunch of people to

20:07do these like there were cash grabs lots of cash grabs and i feel like now we're kind of into a place with the nft 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 um is more unique like at least has some edge there's some road map there's some like something interesting about it or like brands are trying to drive interesting extensions or work on things it feels more like an ideal laboratory to me now than like a cash situation

20:38where people are just trying to make money and so i think this situation is like it's a a collision of two really hot button issues like one being you know tai 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 um you know nft cash grabs and people perceiving the like collision of these two things is a very very uh you know it's a combustible situation and so i i can see why this would be a situation that would have that and i'm like you know i'm

21:12looking at some of the um 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 uh 0x underscore beans he said like he pulled up the code base from it he said hilarious the tai lopez nft immediately siphons 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 uh within the nft and crypto community broadly towards this and i think look um sorry my final thought on

21:43this is it behooves the crypto and web 3 community the like real believers who are going to be here for the next 10 20 whatever years um 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 um 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 um uh donations so any like it's it's

22:22encouraging 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 uh you know i think the gold pass it meant for between 80 and 100 each you know that's which is you know 100 and a couple hundred grand um just for access to this nft and you know i think there's that's a that's a lot and that's exactly why a lot a lot of the uh there is a lot of blowback from a lot of these projects um because you know

23:03you could buy this thing for 260 grand and then three months later tai lopez could be off to the next shiny object so um we're seeing that a lot a lot right now from um the nft community which is high mint prices um are our big faux pas so uh interesting to see we'll see you know who knows maybe tai lopez ends up making this like garyvee like like a v friends and it ends up being being an amazing collection um or maybe you know we come back in 12 months from now and it goes to zero yeah what's your guess um and you can be honest i don't i don't

23:44know i it'd be great to get tai on the show someday and and ask him these questions directly but if we don't that's fine so do give your honest take i mean if 97 of nft projects go to zero it's just more likely that this project goes to zero yeah the base rate is pretty bad that's true um 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 um the flip side is like if there are people that want to hang out with him that much that they're willing to pay

24:21that much in u.s dollars um 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 um it gets donated warren buffett does not need you know a few hundred grand or or whatever it costs but i need to pull it up i think like um i think a crypto person paid like a couple million dollars to do the lunch with him um one year uh and it regularly goes for like many hundreds of thousands or into the millions of dollars um to have lunch with warren buffett warren buffett much more [ __ ] impressive than tai lopez

24:54no offense tai lopez i just it's warren buffett like i kind of get it and warren buffett is auctioning it off um 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 tai 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

25:31have been way higher higher if he just would have taken the club cpg model crypto 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 16 12 69 eth he's adding value um that's what i would have done if i was tied to 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

26:11to have any hope of reviving this situation i feel like that's got to be the uh that's got to be the move at this point um but yeah i mean the warren buffett thing by the way i just looked it up the the last one sold for point five six seven million dollars uh justin sun the uh the crypto uh the tron guy um bought it for uh for 4.6 million dollars bought a lunch with him 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

26:42for the warren buffett charity uh charity lunch but i don't think tai lopez is quite on the same level as it um and to me it looks like uh looks like a cash grab cool you know it's like the duck test man if it uh it's like if it looks like a duck and it quacks like a duck it's probably a duck uh that's kind of how i feel about it so i'm hoping to be 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

27:14to 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 multi-family 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 dash markets dot com slash room and get a 50 bonus when

27:57you deposit at least 500 93 of your life is 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 when i moved to new york last year and got a new place one of my priorities was finding an outdoor workspace outer's products have provided me with that game changing experience i now have outdoor furniture that's durable that has modular designs it has lifeproof material that withstands the weather and the fluctuations that new york often brings they have a patented built-in outer shell cover to keep your

28:39furniture 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 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 three hundred dollars 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 and we'll we'll let him in once he gets on

29:22but i'm super excited to have this discussion because i've been wanting as you know you know one thing that's been on my list for a while to talk about like 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

29:52about matt mullenweg who i think you know um or you've met at some point in the past but matt you know he was actually the creator of of wordpress so he's like an open source og um has been around for a while is like an amazing entrepreneur and now he's the founder and ceo of automatic um and uh and the company's i don't know it's 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

30:28journal and so i just realized this is the guy we have to have on to uh to have a discussion around this yeah absolutely i'm excited to chat with him um i met him many many years ago so we'll see if he remembers me yeah he's um 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 um off of that open source foundation yeah i think what i 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

31:05a 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 i know that he's done that successfully so i'm here to learn yeah it's um 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 um you know if you're not back in the

31:42office uh you know you're dead like i saw uh keith keith reboy um the founders fund and you know amazing entrepreneur investor um tweeted out this morning uh you know in response to a tweet saying that startups so 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 uh replied back to him in his in his typical punchy fashion um that he operates on twitter so i thought that was an interesting backstory to it too yeah [Music] amazing first of all um

32:22amazing response oh what's up matt hi hey matt what's going on i'm doing pretty well thank you so much for having me today where are you uh where are you joining us from actually houston texas nice nice so you haven't hit quite the like swampy summer months yet within uh within houston no it's chilly rainy and cold oh man well thank you uh thank you so much for making a few minutes of time i know you're busy and have a ton going on and um the world is in a lot of flux right now so really appreciate it um you know this is super casual we don't

32:58consider this an interview show by any means um 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 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 um but i first came across you um in this wall street journal article that you're probably been sent a million times that was talking about your

33:30perspectives 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 um 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 um so we'd just love to get your perspectives on like where that ethos came from and and um 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

34:03automatic 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 um it was developed online from people all over the world so myself the co-founder had never met in person he was in the uk i was in houston texas where i am today and um 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 passion a community is a passion that came together from everywhere so uh although that was new for companies and we got a lot of pushback once i

34:42started 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 um you know when people point out the like evolution of the internet and everyone talks about web3 now um it's kind of like what's new is also old because you know the web one 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 um so it feels like this is kind of the natural extension of

35:15that as you talk about it matt did did you ever have a did you ever have a stint in san francisco was there ever a point where you moved the company to san francisco because i do remember a um presence a big automatic presence uh like on the bay somewhere yeah so my story i i had um gone to university of houston for two years and then a company called cnet paid me to drop

35:44out moved to san francisco in 2004. so this is about year year and a half after wordpress started but about a year before i 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 like i i actually really love san francisco so and we uh at first had like a desk in

36:21our investor's office so true ventures had a spot on pier um you know instagram was upstairs there was it was a fun spot and um and then later that expanded office next door came available so we 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 like 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

36:54year but it just felt like the best most talent in the world was not in san francisco regardless of all the smart people was meaning it felt like a very small pond efficient 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 uh 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

37:32being in a location you know and i say that in the context of san francisco because i think part of the um you know 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 went i was at stanford and i was kind of at in school during those years and you know even after when i started working going to the gym like you just run into these amazing

38:03entrepreneurs you know investors founders etc um how do you do that like where is the serendipity in this more remote or hybrid world how do we how do we find that uh 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

38:46everything and where the fun was and so now like even like i'll go to dinner in san francisco and people were talking about the essay they read online they're not talking about what you know marc andreessen said to them at the gym they're talking about the thing he posted or the new article everyone's talking about or um the latest newsletter that's that's what's uh 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 um i met you actually at a jazz show

39:24how cool so i met in sf so i i was living in montreal at the time and you were there for the jazz festival i presume yeah 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 um and actually what ended up happening is you i think you might have introduced us to someone on our team on your team we ended up doing we ran an agency and we did

40:06we 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 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

40:51all 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 so you know what advice do you have for people who want to increase serendipity um say yes go to parties go to events go to conferences go to jazz festivals you know 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

41:30city to be in so i'd always rent an apartment there for like a month in the summer um but we also you know a big part of the wordpress uh ethos is something called word camps which are community organized so that was also a reason i went to montreal so um inspired by bar camp which i was uh kind of a co-founding associate of um 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

42:05single one because i was like if someone's going to do a conference about wordpress i'm getting on a plane and go in there so i'd 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 um 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

42:36always on a plane you know 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 um uh about how to i mean i call it expanding your luck surface area or like expanding your serendipity surface area 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

43:12is 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 um 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 so in that movie there's this um scene where they're talking about that tiny little planet that was next to the black hole and how they're talking about the the lack of life on that planet and there was a concept that they talk about which is

43:48basically 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 seat 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 you know pessimists who are around you

44:22like 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 um and so it's like deliberately taking actions that expand open the aperture

44:53expand your serendipity surface area um feels like the path to going 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 at the very top of their game um 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 hendrieson 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

45:31viewed him totally wrongly as more like a an internet 1.0 guy who was like didn't really know what was going on but wait i was totally wrong um and later once he started publishing i was like wow this person is is a genius you know like what would injuries and horror words be without mark's seminal essays and ben's amazing books and essays you know like their writing is part of how they they disrupted the vc model and became injuries and horowitz which i would take for granted 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

46:08insights 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 and 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

46:42ideas with your insights with whatever you're sharing that really can attract millions you know billions of people at scale um 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 you know if it's a medium essay or something like that people just remember that was on medium they don't

47:16remember your design your name your everything so it's really nice to have a differentiated presence online yeah right before this we were talking about keith roboy had this tweet um or he was just talking about how uh what was it sahil like basically someone had tweeted you know that startups were starting to buck the trend um 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 um and so greg and i were chatting about that kind of having a debate about it like is it true

47:55that young people are going to buck the trend of remote um 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 us-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 um these are these huge opportunities aren't just as readily available to walk into these doors and apply and start working so i think

48:41writing um is such a great way just to attract um 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 um 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

49:20yourself 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 uh you know a world where everyone has kind of equality of opportunity we're you know i'm a capitalist and so i am all for um 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

49:56landscape 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 um and the customers so you should make the same pay uh guess what that's an amazing innovation actually there was a i don't know if you saw this map there was an article in the atlantic maybe like two three weeks ago that was all about tech companies trying to do the like um geographic discrimination on pay you know like someone in san francisco would move to nashville or

50:31move to boise and um the companies would cut their pay and that was like the original assumption of big tech post right when covet 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

51:01how 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 in office is the future or distributors of future anything i think it's about giving people the choice and

51:34the autonomy so at automatic you 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 you can be around that energy you can go to miami and be at the same co-working spaces keeps companies if you want like that's fine so it's just about giving

52:03that choice and that's where i think people really thrive because some people do want to be in an office environment great they can work for automatically in the office environment we allow people in the same cities to pool together so again pre-covet 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 uh it's not like some you have to choose one way or another and that you're wedded to that forever you just have to listen to your people what do they want the cool thing about a lot of this too

52:35what you pointed out is the market will decide right they're 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 uh the old way you know the kind of industrial era style of work and then they're gonna 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

53:03well 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 um 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 you know we're 2000 people now uh we hired 700 last year by the way so you can scale this quite a bit if a team wanted to be in person or get

53:32an 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 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

54:09basically create teams remote but in certain time zones so you 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 us is okay because you can still overlap for an hour to a day and that's 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

54:43asia 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 anything you know systems or anything you need responsiveness and 24 7 coverage of which every business at scale does for certain things it's 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 responsiveness of their support by hiring more folks internationally

55:21they would uh develop much bigger queues on weekends and outside of the u.s uh east coast time zones hours and so that also meant that bad guys would start to take advantage of the eastern hours you know they knew that there would be longer response times they did things in the middle of the night in new york no longer can you talk about tumbling 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 some tlc was was gonna be put to that platform so i'm just curious

56:00is there is there anything you can share around why you bought tumblr and and why 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 of blogging um it is majority so 55 uh 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 signups per day very active and um it's actually the i think the the queerest social network it's about at least a quarter

56:37lgbt plus so it's it's a really fun creative space for art and artists and um 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 tumbler a ceo um working on the product working on design working on the tech working on everything and so hopefully we can accelerate the pace of uh 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 feed so we need to make that an onboarding

57:11experience better but when you get your feed dialed in it's one of the funnest places on the internet so before we um before we let you go matt i i'm um 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 um but you're not a um loud showy you know jump up on stage pound your chest type guy it hasn't been to karaoke that's true i'd love to go to karaoke with you actually um we'll do that sometime i will come visit houston we'll do that i've actually been to a great karaoke

57:53place in houston that i'll send you but um you don't strike me as that type can you just give us um a couple of like your kind of realizations or lessons on leadership um 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 um as it comes to leadership yeah i know we're at time but the i guess the main thing is that i am not like the rah-rah running 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

58:32point 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 um you know i've especially 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 academic sometimes in my speech so yeah just look for that um and just but do do you it's a great realization so when i tried to change it wasn't as good it's a great one yeah i apologize i gotta run thank you so much

59:02yeah no i appreciate it i thank you so much thank you so much for joining us join our free community at trwih.com

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