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SPEAKER_02
How you doing, man? Good to see you, good to see you. 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.
SPEAKER_01
Totally, what? I've got a list.
SPEAKER_02
Yeah, you got a list? I've got a list, man. I mean, well, first off, since we last recorded, the world has exploded 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. And a few things related, kind of the more the business side of that, that I was hoping to chat through today.
But I had an interesting conversation last night that I wanna 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 works right now at McKinsey. And he's really like an entrepreneurial guy and he 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, 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 10 X like opportunity on that cash, the cash that is your life, you're gonna 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, cause 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.
SPEAKER_01
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 high paying job.
SPEAKER_02
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.
SPEAKER_01
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 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.
SPEAKER_02
So there's mailbox money is a cool concept. I've talked about that with the Dama Kong Sue 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 for the rest of your life is, you know, 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.
SPEAKER_01
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.
SPEAKER_02
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, 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've 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 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 of things.
I've got a couple of things. You want to just jump right in? Yeah, let's, 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 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 in insane amounts into supporting Ukraine in this battle against Russia.
And I think the most recent numbers I saw before we were recording was something like $60 million of crypto assets had been raised. And people had donated, someone donated a crypto punk. Gavin Wood, the founder of Polkadot, donated $6 million of crypto.
So it's this amazing show of force from the kind of Web3 and crypto community in coming together and supporting this. And it's so counter to the broader narrative of like, crypto is for fraudsters, scammers, criminals, degenerates, et cetera. So I'm curious for your thoughts on it.
SPEAKER_01
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 I think the $50 plus million going to Ukraine has taught mainstream audience is that the spectrum is now enlarged in a lot of people's brains. Now a lot of people are like, OK, like, 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.
SPEAKER_02
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, broadly, just from the outside looking in, even not being someone that's super involved in the community.
I mean, you had there is a Polkadot founder, which I mentioned, chain CEO, Deepak Thapliyal 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 such like really amazing things. There was a Russian national actually living in the US 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 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, there's 7 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.
SPEAKER_01
Yeah, it is wild. I mean, well deservingly, for sure, I think. Yeah.
SPEAKER_02
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 Apple announced they were closing operations within Russia. They don't have any Apple stores there, but they were shutting down 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. 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 reaction from the tech community. The cynic in me says, yeah, well, the ruble, 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 kind of tech and business community is coming together and rallying against the dictator to go do this.
SPEAKER_01
So what do you think? Well, first of all, I saw today that we work, CEO, is one of the companies that he, I'm pulling up the quote, we work, won't exit Russia where biz does quote unquote, incredibly well. So theme of this episode is spectrums. And I think like you're also seeing people go on the other side of the spectrum and they're doubling down, which is.
SPEAKER_02
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 McDonald's, which at least as of now, I think it has like 847 restaurants in Russia.
And I mean, they're refusing to close them. And I think 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.
SPEAKER_01
Yeah, and it's like, it is crazy. It's absolutely, it's bonkers.
SPEAKER_02
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. 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 guests in.
SPEAKER_01
OK, so a new NFT project. Tai Lopez launches NFT project. Did you see it?
SPEAKER_02
Who is Tai Lopez? Tai 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?
SPEAKER_01
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 this is my house. And like, let me show you how, like, you can have this. And he would sell stuff, you know, courses, that.
Now, fast forward to today is I think 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.
SPEAKER_02
I think he bought Pier 1 imports. I think he bought, like, the e-commerce business of Pier 1. Yes.
SPEAKER_01
OK. So that's, you know, Tai 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?
SPEAKER_02
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.
SPEAKER_01
He's polarizing. He's definitely, he's very, very polarizing. And I don't know enough about, like, Tai Lopez, if you're listening to this.
And I know you follow me on Twitter. So, like, 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.
SPEAKER_02
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, right? It's like Grant Cardone, Tony Robbins, Gary V gets shit for that kind of stuff.
And, but, like, Tai Lopez has a million and a half subscribers on YouTube. Like, he 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.
SPEAKER_01
Yeah, I think, 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?
SPEAKER_02
No, I haven't seen it. Tell me about it. I'm going to pull it up while you're talking.
SPEAKER_01
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, with Tai Lopez. So I pull, you know, I'm pulling up a tweet that I saw.
It's a, you know, from this, this guy, Eddie is Kong's. Hey, at Tai Lopez, legit question. Why would I pay 30,000 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 definitely 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 around, you know, why you 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 Af Faroq.
He's the founder of Rock Radio. He's really well known in the crypto community. And he got in a fight with Tai Lopez on Twitter.
And here's the tweet. 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 Faroq and Tai Lopez. And I'm like, well, I'm going to be on Twitter at this party. So a lot of drama in the crypto Twitter space.
SPEAKER_02
What do you think? I have a lot of thoughts here. So I don't know Tai 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, et cetera. I don't know anything about Tai Lopez. There is a lot of animosity in general towards cash grab NFTs, right? Like 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 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 is more unique.
Like at least has some edge. There's some roadmap. 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 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, Ilobez'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 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, 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 web three 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 three, as we talked about in the context of the Ukraine and Russia donations.
So any, like it's, it's encouraging to me to see the crypto and web three community policing things that they perceive to be below bar.
SPEAKER_01
Yeah, 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, it mints for between 80 and 100 ETH, you know, that's, which is, you know, 100, 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, Tai 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, are big faux pas.
So interesting to see, we'll see, you know, who knows, maybe Tai Lopez ends up making this like Gary V, like a V friends, and it ends up being, being an amazing collection. Or maybe, you know, we come back in 12 months from now and it goes to zero.
SPEAKER_02
Yeah. What's your guess?
SPEAKER_01
Um, and you can be honest.
SPEAKER_02
I don't know. 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 give, give your honest take.
SPEAKER_01
I mean, if 97% of NFT projects go to zero, it's just more likely that this project goes to zero.
SPEAKER_02
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 that much in us 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 fucking impressive than Tai Lopez.
No 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, what 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.
SPEAKER_01
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 have been way 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 a 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, 6, 12, 69 E. He's adding value.
That's what I would have done if I was tired, just started 300 and then added as time went on. Yeah.
SPEAKER_02
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 dollars. Justin Sun, the crypto, the Tron guy bought it for, 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 for the Warren Buffett charity, charity lunch, but I don't think Ty Lopes is quite on the same level as it. And to me, it looks like a, looks like a cash grab.
Cool. It's like the duck test, man. If it, it's like, 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 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.
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SPEAKER_01
I think we have a guest coming up, don't we?
SPEAKER_02
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, one of the things 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, 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, et cetera. 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, and the companies, 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 and the Wall Street Journal. And so I just realized this is the guy we have to have on to have a discussion around this.
SPEAKER_01
Yeah, absolutely. I'm excited to chat with him. I met him many, many years ago.
So we'll see if he remembers me.
SPEAKER_02
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.
SPEAKER_01
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 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 fun as possible and is, and yeah, and I know that he's, he's done that successfully.
So I'm here to learn.
SPEAKER_02
Yeah, it's, it's such a hot button issue right now to the 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 Raboy, the 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 bucked 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 him in his, in his typical punchy fashion that he operates on Twitter. So I thought that was an interesting backstory to it too.
SPEAKER_01
Yeah, amazing. First of all, amazing response. Oh, what's up, Matt? Hey, Matt.
SPEAKER_00
What's going on? I'm doing pretty well. Thank you so much for having me today.
SPEAKER_02
Where are you? Where are you joining us from? Actually, Houston, Texas. Nice. Nice. So you haven't hit quite the like swampy summer months yet within, within Houston.
SPEAKER_00
No, it's chilly, rainy and cold.
SPEAKER_02
Oh, man. Well, thank you. 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 and you know, and how it's kind of played through the automatic story.
SPEAKER_00
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, 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 passion or communities of passion that came together from everywhere. So although that was new for companies and we got a lot of pushback 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.
SPEAKER_02
Yeah, it's sort of like the, you know, when people point out the like evolution of the internet and everyone talks about Web three now. 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.
So it feels like this is kind of the natural extension of that as you talk about it.
SPEAKER_01
I think 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.
SPEAKER_00
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, 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, passionate 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 actually really loves San Francisco.
So, and we at first had like a desk in our investors office so true ventures had a spot on peer 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 host community events and do WordPress meetups and so I got my big believer in in person in physical space. A big part of automatic culture is actually meetups where we bring out of 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 felt like a very small pond of fish in so we were trying to compete with the Google's and Facebook's of the world like we had a fish in the world.
We had a 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.
SPEAKER_02
How do you think about scaling the kind of serendipity that comes from being in a location, you know, and I say that in the context of San Francisco because I think part of the, 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 entrepreneurs, you know investors, founders, etc. 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.
SPEAKER_00
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 1015 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, or the latest newsletter. That's 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.
SPEAKER_01
I do have a confession to make so many years ago. I met you actually at a jazz show. 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 our team on your team.
We ended up doing we ran an agency, and we did. We helped some companies actually move from their custom CMS is 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.
SPEAKER_02
What a cool thing.
SPEAKER_01
Yeah. So, while I 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 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.
So, you know, what advice do you have for people who want to increase serendipity?
SPEAKER_00
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 wrench 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 word camps, which are community organized. And that was also a reason I went to Montreal.
So inspired by bar camp, 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 plane and going there.
And I would go by 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 twenties 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.
SPEAKER_02
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. 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, 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, you know, 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 it 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 kind of making your own luck as it were.
SPEAKER_00
I love that. I'll have to check out the 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 Andreessen 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 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 horror would be without Mark Siminal 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 Andreessen Horowitz, which now we take for granted.
Remember that they were like newcomers to the scene.
SPEAKER_02
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 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 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.
SPEAKER_00
The best hours I have spent in my entire career are those writing and publishing. And I'll pitch wordpress here to 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 remember your design, your name, your everything. So it's really nice to have a differentiated presence online.
SPEAKER_01
Yeah, right before this, we were talking about Keith Reboy had this tweet, or he was just talking about how, what was it, Sahil?
SPEAKER_02
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?
SPEAKER_01
And my pushback to that whole like energy is 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.
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.
SPEAKER_02
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 be in favor of, you know, a world where everyone has kind of equality of opportunity. I'm a capitalist and so I am all for unequal outcomes because I think that performance and doing well, like you should be rewarded for outsized performance, but equal opportunity with unequal outcomes.
SPEAKER_00
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, same job, you're creating the same value for the company and the, and the customers, so you should make the same pay.
SPEAKER_02
Yeah, 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 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.
SPEAKER_00
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, etc.
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 is the future or distributors the future or anything.
I think it's about giving people the choice and the 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 wherever you want to go.
So you can be around that energy. You can go to Miami and be at the same co-working spaces Keith's companies if you want like that's fine. So it's just about giving that 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 automatic and we can office environment. We allow people in the same cities to pull 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 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?
SPEAKER_02
The cool thing about a lot of this to 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 will know you know in the next five, 10, 15, 20 years will 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.
SPEAKER_00
We're talking about companies like their monoliths, but it could also be within teams or divisions within a company. We're 2000 people now. We had 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 it'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.
SPEAKER_01
How do you think about time zones and time zone working? A lot of people have teams where they'll have 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?
SPEAKER_00
I think for teams it's good to be in a range. I'm actually okay with a range of up to 7 or 8 hours. So like Europe and US is okay.
Because you can still overlap for an hour to 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 Asia Pacific, America's 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 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. They would develop much bigger queues on weekends and outside of US 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.
SPEAKER_01
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 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?
SPEAKER_00
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.
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 signups per day, very active. And it's actually the, I think the, the crearest social network, it's about at least a quarter LGBT plus.
So it's, 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 feed, so we need to make that an onboarding experience better.
But when you get your feed out in, it's one of the funnest places on the internet.
SPEAKER_02
So before we, before we let you go, Matt, I'm, 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?
SPEAKER_00
Yeah, I know we're at time, but the, I guess the main thing is that I am not like the raw, raw, 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 greater than things that you're not. So as you grow, your team, your company, 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.
And just, but do you do great realization.
SPEAKER_02
So when I tried to change it wasn't as good. It's a great one. And I apologize.
I got to run.
SPEAKER_00
Thank you so much. I'm a meeting. Yeah, no, I appreciate it.
SPEAKER_02
Thank you so much. Thank you so much for joining us. Join our free community at trwh.
com.