Matthew Mottola | What AI Can't Replace

Timothy Allen: I saw you talking to a friend of mine, so I came over and I butted in, because he’s normally got interesting friends.

Matthew Mottola: Very interesting friends.

Timothy Allen: Yeah, right. So you better tell me who you are.

Matthew Mottola: Yeah, so Matthew Mottola, CEO of Human Cloud. We are a platform for flexible talent solutions. You think about the kind of OG freelance world, which was like a couple of platforms, right? Upwork, Fiverr, Freelancer, you name it.

Timothy Allen: Wow, you call that OG. Dude, I’m 54. That ain’t OG. But anyway, go on.

Matthew Mottola: Technically, it goes back to 97. Elance, Odesk. There’s now a thousand-plus of these solutions. And when we look at the world, we say, hey, it’s going to become more flexible. What does that mean? Usually independent contractors, usually talent-platform led. But there’s thousands of these things. It’s fragmented. Most of them aren’t even here. And so we aggregate that so companies can go more flex – not agency, not staffing, something in the middle.

Timothy Allen: So an aggregator of platforms that offer work to freelancers.

Matthew Mottola: Yes, exactly. And the reason it matters – because why, who cares, right? Why have this middle layer? The scoping is where these platforms shine. So if I tell you, hey man, we want to do a Super Bowl ad, you think, okay, just a video. No, no, no. We’re talking shooting. We’re talking script. Potentially five-plus vendors, 100-plus contractors. Our platforms are really good at doing that scoping.

Timothy Allen: I’m thinking, strictly speaking, I’ve been a freelancer my whole life. Even when I used to work as a news photographer at a newspaper in my twenties, I was a freelancer there. I never actually got a job.

Matthew Mottola: That was OG.

Timothy Allen: Yeah, it was. It was word of mouth. We got all our gigs by phoning someone up – a picture editor, you would have called them at the time. You phoned them up on the desk and said, hi, my name’s Tim Allen, can I show you my portfolio? And you go in and you have a meeting and they say yes. And then they talk to their mate and their mate. That was crazy. But you’re talking about things like Fiverr, Upwork.

Matthew Mottola: Next level. So Fiverr, Upwork are good for, let’s say, task-based, quick, and typically a hundred bucks to a thousand bucks, right? You’re not going to give them $10 million.

Timothy Allen: Oh, right. So there is a layer of freelancers that – what’s that layer called? The rich freelancer?

Matthew Mottola: Think about it as professional service, right? So if you want to spend 500 to 5 million, you go to Deloitte. If you want to have an ad campaign, you go to an ad agency. If you want software development, you go to Accenture. It’s the layer before that, that says, hey, this is definitely a multi-freelancer or multi-individual thing. This is not a quick task. This is not a quick landing page. This is a big engagement.

Timothy Allen: And you used the example earlier of a Super Bowl ad. Is a lot of it media stuff then?

Matthew Mottola: Yes. So at Microsoft – which is my background, I was Gigster, Microsoft, now Human Cloud – around 79% of it was creative. It’s because it’s easy to scope and be outcome-based.

Timothy Allen: Is it like Fiverr where you sort of put your “I want this” on the site and then a bunch of freelancers reply to it?

Matthew Mottola: No, no, no. Not for that kind of money. Think about it in the middle. Staffing firm is Fiverr if you replicate that. So staffing firm goes, oh, you want Super Bowl campaign? Here’s a thousand resumes. And you as the CMO or marketing manager – I don’t want that. I don’t care. Agency or professional services firm is the opposite. Okay, you have a problem, want to get a Super Bowl campaign done, we’ll do all of it for you. Problem is they’ll do it for maybe $30 million. The thing they sell you, they don’t have the people who actually did it on the project. In the middle is where we sit. So you have these flexible talent solutions that have the exact people who did the exact project beforehand. So you don’t have to worry about a bunch of fluff, scope creep, agency creep, but we’re also not going to get that staffing experience.

Timothy Allen: But who is on the platform? Is it someone who’s in charge of a team of people? Say someone who’s already done an ad, say they did an Uber ad. So why aren’t they working at agencies? That’s what I don’t understand.

Matthew Mottola: Yes, there’s the inevitable question, because the agencies are actually hiring freelancers. They just don’t tell you. If you look at what an agency works like, someone wins it, someone does the work. And if you look at the agency structure, it was typically full-time-led, but increasingly full-time employees are not the ones who are the best at X skill – X being say something like digital growth campaigns, video production, you, right? You are not going to go work at an agency. I need to access you. And so these flexible talent solutions are really good at leveraging digital networks rather than having to have a bunch of full-times on their book.

Timothy Allen: And do you find that agencies are growing up on your site, so to speak?

Matthew Mottola: Yes. In a perfect world, we’re all full-time employees or we’re all agencies, right? That would make life so much easier. The best freelance platforms are like 20 to 50 full-time employees per every 1,000 to 5,000 freelancers. So it’s not an absolute. It’s not all full-time employees, not all agencies, but it’s rebalancing that equation where for only, let’s say, one full-time employee, you have 100 contractors. They’re just resetting that equation.

Timothy Allen: Right. So they are companies on there. They’re not individuals. Like, this is how it used to work when I was young. Because I worked in the ad world as well. I had an agent, used to get me jobs, really well paid. And I, as the director, used to pull in my favourite people, basically. Now if I was to go on your platform, I’d do it exactly the same way. I’d go in on your platform as me. I might invent a name for my company, even though it’s just me. And if I was pitching for one of your Super Bowl ads, I would show you my resume and it would be because I know all these people that want to work for me. Is that kind of how it works?

Matthew Mottola: Kind of. So what you’d see is you would say, okay, Super Bowl campaign, let’s get it done. What we would say is, let’s focus on the capabilities. To me, a capability is an agent, a skill set, or an outcome. So the skill set is something like, well, we need a JavaScript developer, we need a Descript, meaning like a video automation platform. An agent is “give us this agent.” And so what you would do is you’d come to us, and we would say, okay, there’s five solutions that seem to fit your goal. This solution, which is a talent platform, would say, okay, we want to get a Super Bowl campaign done. Let’s talk about you at the most hyper-specialised level, and let’s place the exact people. So your book, right? These flexible talent solutions, they’re just better at leveraging that book. So they would say, you know, your first name was Dave. They would say, hey, this is Dave. Dave’s done these 500 projects with companies just like you, and we’re going to place Dave on your project, but we’ll also help scope it out so that you don’t have to worry about all the milestones and SOW creation.

Timothy Allen: Right. So the bits I wasn’t an expert in. My cameraman, I could still pick. But the guy that did the graphics or wrote the code for something we need. Okay, I understand. Can we broaden the topic then. I mean, the essence of what you’re talking about is remote work as well, isn’t it?

Matthew Mottola: There’s no such thing. It is pure remote work. I break it down. I call it the transition. And what I mean by this is there’s a transition happening and there’s a flip. The transition, I would argue, is from full-time default to flexible default. And it doesn’t mean everything to freelance or everything to remote. It simply means work is becoming more flexible because technology is making it easier to be efficient. So the transition is, hey, I have 100 full-time employees. Let’s lay off 40. Right now, we’re seeing across most large companies, let’s lay off 40%.

Timothy Allen: Really? Is that happening?

Matthew Mottola: Yeah, 10 to 40% easily. I heard someone on stage recently, like this morning, saying we’re not laying anyone off. I thought she was lying as well.

Timothy Allen: You reckon 40%?

Matthew Mottola: Yeah, minimum. Well, I wouldn’t say minimum. I’m going to say for full-time employees that spend over a billion on talent, I’m saying there’s going to be 40% layoffs. And they might say only 10%, but in reality, they’re recalibrating easily up to 40.

Timothy Allen: All right. Going back to what you were saying – were you saying a company would restructure itself by knocking off the 40% and then appearing on your platforms as a company with 40% less people?

Matthew Mottola: Yes.

Timothy Allen: And then the people that they’re missing, you fill in the gaps.

Matthew Mottola: Yes. And what we’re seeing, especially in the past two months – it was Disney, there was one other company, direct marketing layoffs. And we were seeing this spike on our site, marketing-related inquiries was up like 140%. At the same time, we were seeing layoffs happen across the industry directly in marketing departments.

Timothy Allen: Wow, 40%. It’s funny, I’m having mixed conversations about AI. You’re number seven today. I’d say it was pretty 50-50, doom and the opposite of doom. What’s the opposite of doom? Gloom. No, gloom is – that’s doom and gloom. Never mind. Happy.

Matthew Mottola: Happy. Yeah. 50% good, 50% bad. I’m saying it from a place of happy, but realising that there’s definitely some recalibration. So what I mean by this too – if you look at a team, LinkedIn said it best, or Satya said it best about LinkedIn. The five jobs that used to mean front-end, back-end, PM, designer, and something else have now been scrunched into one called a builder. That means that now for every five roles, that’s now just one role. Likewise, there was another one I heard last week with Block – teams of 14 are now teams of six. So the reason I say 40% is, it’s really simple. You need less to do more. And of that, when you build up, you’d rather have it be specialised, outcome-based and elastic rather than having a bunch of full-time employees.

Timothy Allen: How much of that 40% of people are going to find other work, do you think?

Matthew Mottola: I don’t know. Don’t ask me.

Timothy Allen: Oh, shit. But this is what a lot of people are saying. I take that as meaning they’re not.

Matthew Mottola: I wouldn’t say that, but keep going.

Timothy Allen: Well, because it does seem quite serious. Look, I’m 54, right? In my experience of life, when people get dramatic and frantic, it’s normally the time to stay calm because it’s not going to happen. That’s been my experience over the last 54 years. When people are screaming and shouting that the world’s about to collapse, it never does. So you don’t need to worry. But with this, I’m starting to doubt my own thesis because some people keep saying what you’re saying. I don’t know. Normally people are quite happy to put their opinion out there and say, yeah, probably. But it’s really – I don’t know.

Matthew Mottola: And I don’t know either. I’ve talked to a lot of people and I don’t know. I’ve had more Waymos than I’ve had human-driven cars since I’ve been in Austin. So I can conclude people who drive cars are probably going to go out of business slowly but surely.

Timothy Allen: Right. So what can we say about –

Matthew Mottola: Let me pitch the happy. Actually, I’ll give you the real doom, but then I’ll give a happy spin. I’m actually going to use you as the perfect example. So let me start with the doom. At Human Cloud, we were spending between five and ten a month on production. Podcast, newsletter, media, all that. When we dug in, we automated 98% of it using Claude, but then integrating with different tools.

Timothy Allen: Wait a minute. Because I know about producing media. Where did you streamline that much? Because you still have to produce the media, right?

Matthew Mottola: The only thing that wasn’t automated was this right here. A little bit of the scheduling at first, but now actually that’s even getting replaced.

Timothy Allen: As in getting the guests in? You had an AI doing that?

Matthew Mottola: We’re starting to. And we’re lucky because we have most of it – it’s all warm guests, so we’re not having to go prospect. But I’ll tell you exactly what. So you and I record this right now, right? It kicks over to something like Riverside. Riverside does magic editing and then creates five to ten highlight videos. Now, here’s the funny part. We still have yet to figure out how to get Claude to talk to Riverside. So a human goes in and manually downloads. But then Claude, the skills we’ve built, comes in, goes to the download folder on the local machine, creates all the highlight videos, creates the actual podcast ready for production in Megaphone. And then I still have to click schedule, but all of it’s been created. Now it also creates an article. It also creates the emails to the guest, three of them saying, hey, I had a great time, and then week-before. It also creates five to fifteen of the highlight videos that Riverside had created. It puts them onto YouTube. It fills out the title, the description. So when you play this out, this – meeting in person – is invaluable. This will never get replaced, but all that other stuff is within reach. Now here’s the happy side, because that’s really bad.

Timothy Allen: That isn’t bad. Not for me, isn’t it?

Matthew Mottola: No, for you it isn’t.

Timothy Allen: What you’ve just described, sorry to butt in, but you’ve described my workflow, except there’s a few more times in mine where I have to put my hand in. There’s lots of that I haven’t automated. Editing, automated. Show notes, articles, automated. But I’m still uploading articles, I’m still uploading the YouTube video, I’m still sending that email by hand. And actually, personally, I’m not ready to give that up yet because AI is so sloppy. I hate getting AI emails and I hate looking at AI summaries of stuff already. And it’s not been that long. So I’ve started stopping that and writing bits myself and making it very obvious that it was me actually doing it.

Matthew Mottola: Now I’ll make that really scary. We actually have a slash-human command, and it’s then implemented into our audit command that it now is trained to not look like an AI. And every two weeks, it’s doing new research to figure out what an AI would do.

Timothy Allen: Terrifying.

Matthew Mottola: But here’s the happy picture. So I’ll give you a Claude. We don’t care if our podcast is as good as yours. We care that it’s consistent, the guests are good. So we have a lot of leeway on stuff we can automate. What I just described to you, agencies and full-time employees are billing out 10 to 25k a month to do what we now do. And it’s 98% automated. So that’s the doom.

Timothy Allen: Before you go on. For example, clips, right? My podcast has clips. We have two a day across social media. I have to check every single one of them by hand for spelling mistakes, for just not getting the point, for all this kind of stuff. So that I’m not even prepared to give to an AI yet. The AI creates it – I use Opus, it creates all the things. I go into every one. I correct the spelling mistakes because it’s bad with proper nouns. It says “gonna” instead of “going to”, and I can’t seem to tell it not to. It’s so badly done. So I agree you can automate all this stuff, but how good do you want your –

Matthew Mottola: Yes. So we gave the doom, which is, holy crap, 98% of a $20,000-a-month job just got automated by us. And I didn’t bring up how it’s integrated into our newsletter and other things. So even our newsletters are now automatically generated as well. Beautiful flywheel. But here’s the happy picture. When we were just spending, say, $20,000 a month, in absolute terms, that means nothing. In relative terms – if your level of podcast delivers X number of customers, or we can tie it to something – it’s infinitely more valuable than it was prior. And another analogy I’ll use is, it used to be only one podcast episode a week. We now can have up to three. We probably could have one a day, to be honest, because it’s just computation power. But in my view, the talent equation – the ARR per employee is the highest it’s ever been. That’s terrifying for employees that aren’t used to having an ARR associated with them. It’s incredible for those that are okay with being tied to their impact, to their outcomes, to the actual end result of their ARR.

Timothy Allen: Interesting, because I’m going to push back on that. Not to say what you’re saying is wrong, but in my world that may not work long-term as a strategy. For example, I have one episode a week. In order to go up to two episodes a week, because I do everything in person – I’ve chosen to do every episode in person, which is, as you know, a massive expense, a massive ball-ache, I have to travel around the world. But I come from the world of filmmaking. I think this is important. And my long-term strategy is, it should be this. I suspect in the future this will show up as a rare quality of a podcast. So I agree, you can put out three a week, you can put out one a day. But I’m already sick of AI. I’m already sick of products and content and stuff. I suspect the curated, good, high-end bit of content might win out in the long run. I don’t know what you think about that. What I’ve realised with the foundation I work with, Free Cities Foundation – they basically can repurpose all of this stuff into so much content. Every conversation I have can be a news article.

Matthew Mottola: Or two or five.

Timothy Allen: We choose something you said. And this is great because, what is the rare part of what’s going on here? It’s this. This is the one part that AI isn’t doing. And it probably won’t ever do, because why would it? Why would it go out there looking to meet real people in real life when there’s a guy or a girl that can actually do that? But it does seem to be the source of all this stuff. And I’m concerned about my own product that I don’t want to dilute it too much with AI. That’s my gut feeling. But then again, I’m old school. I come from the world of newspapers and magazines and nonsense like that from the past.

Matthew Mottola: I hear you. I’m going to use an analogy of underwear versus a t-shirt. Underwear, I don’t care. Can look however it wants. I just want the cheapest underwear bought on Amazon. T-shirt, until you meet a lady in a club and then you –

Timothy Allen: So it’s not a great analogy when you have to sort of strip in front of someone.

Matthew Mottola: That is true. Well, I don’t know what you’re going to say yet. I was going to say, as you know, my wife has yet to push back, and so until she does, I’m okay with the Amazon.

Timothy Allen: You don’t know what she’s thinking secretly.

Matthew Mottola: And this is what happens in business. There’s going to be stuff that we’re okay with being just maximally optimised, and then there’s going to be stuff that we want to be curated. I’ll use even the analogy of a car. Horses are now more valuable than they ever were. But with that said, I don’t ride around on a horse. I use a car. I think that’s similar to what’s going to happen. I use the podcast analogy. It’s good enough for what we need it. It’s not good enough for being really, really, really, really good. But for what we need it for, it’s good.

Timothy Allen: What do you think then? Which parts of the podcast workflow – and by that I mean all these articles and Substacks, reels, short clips, everything – which part of that stack do you think people don’t mind seeing an AI version?

Matthew Mottola: Phenomenal question. And I’ll actually show you. The intention or the core value prop that our podcast delivers for is trust. It’s not the article. It’s not even the presentation, because we do it virtually, intentionally. For us, it’s trust. Our listeners and our customers trust that if you’re on our podcast, we’ve done the vetting, and you’re not – can I swear a little bit?

Timothy Allen: You can.

Matthew Mottola: So our guests are not full of shit. And we don’t have prepared questions. So that’s the part that is intangible, will never, ever, ever be replaced. If you want questions and to be full of shit, go to CNN or some sort of major media. So that’s intangible. As of now, everything else is all secondary to that. The fact that we use a 98% automated production – you still trust the guest because it’s the guest that’s important and the trust that we vetted you, not everything else.

Timothy Allen: But when I go on your Substack and I see the hallmarks of ChatGPT and it pisses me off and I’m like, I’m not reading this shit. That’s already happening to me. Like I was telling someone earlier today, I have had Claude do some of my show notes. And recently I’ve just been scrapping them because the way it writes it, it’s just like, oh my God, that’s such an AI way of explaining what this episode is about. And I’m now going against it. So I’m using it for structure sometimes. I used it the other day because I was re-interviewing a guest after four years. I thought, I wonder what we said last time. I don’t have to listen to the podcast. I just said, AI, what did we talk about, what should we talk about this time? Things like that. But I hardly ever come in with notes. What I’m trying to say is, the backlash in me – it might be because I’m an old fart and I’m 54 and I’m not young and AI-native. I don’t know. What do you think?

Matthew Mottola: With us, you’ll see the em-dash. Well, no, you won’t, because we have the human agent. So you won’t see the em-dash. But what you care about is this, the conversation. You’re going to be listening to our podcast while you’re at the gym, while you’re commuting. You’re not going to be caring about em-dashes. The second thing you’re going to care about is the actual data we’re talking about. So you’re going to care about the fact that our founders who come on our podcast will be talking about their margins. We’ll be talking about the business cases. The em-dashes, they don’t care about. The comparable for us is Deloitte billing 500K or an expert network charging $2,000 an hour. So for us, it’s just a different value prop.

Timothy Allen: What is your podcast, by the way? I haven’t even asked you.

Matthew Mottola: Human Cloud. And this is the thing. It’s all tied. And this is where I think – companies are having to have founder-led marketing. There’s more channels than ever before. So that founder is going to hop on a podcast, going to do a good newsletter, whatever it is. So there’s more channels, but the core value prop has never been more important. For us, our core value prop is getting to the most efficient, flexible talent resource to transition your company to be less full-time and more flexible. Everything else is secondary. So our podcast is getting you the data to transition from fixed to flexible.

Timothy Allen: Something we discovered on this podcast – because originally it was purely funded by the Free Cities Foundation, and it was basically to spread ideas of free cities and independent jurisdictions. What we actually discovered in the beginning, which probably is exactly what you’re talking about, was that it was a brilliant networking tool. We basically met everyone really quickly. And even people you probably couldn’t get a meeting with were quite happy to sit down for longer on a podcast. So if I was starting a company now, one of my big hires would be a professional worker who can do the podcast really well. Because I see it now, it can be the source of so much marketing and anything you want, basically. But you need someone good to do it. Because a lot of people just can’t do it. So did you start your podcast for that same reason?

Matthew Mottola: Yes, but it was an extension. I’ll give you the evolution. So Gigster early, we’re doing 100% custom software through the cloud, all remote networks, fall in love with that. Microsoft – let’s get enterprises to fully embrace these freelance workforces. Exact opposite. Every enterprise is saying, hell no, we don’t want to do that. So then I go and I publish a book – because no one knows what freelance is – called The Human Cloud, published with HarperCollins, went through the traditional channels. Then as part of getting that book out, we met all these incredible people. Then what I learned was – have you used like GLG, AlphaSites, Tegus, these expert networks? They’ll charge you a thousand to five thousand bucks an hour to talk to someone like me, to have a conversation over the phone where I just tell you what we did at Microsoft or what we see from clients. So we published this book, which is telling the stories to show that the world’s going flexible. We then meet these people who GLG would charge a thousand to three thousand bucks an hour to get access to.

Timothy Allen: What are they, an agency, GLG?

Matthew Mottola: An expert network.

Timothy Allen: An expert network. Is that a thing?

Matthew Mottola: It’s a thing.

Timothy Allen: Right. I’m so old-fashioned.

Matthew Mottola: So then our podcast turned into all about transparency, which the core of our platform is about transparency. It’s about getting data into the hands of people that Deloitte used to bill 500K to get that data for.

Timothy Allen: But this is once after you’d started Human Cloud. So the podcast has only ever been –

Matthew Mottola: Right. The podcast was first. And then the company started.

Timothy Allen: That’s what’s happening to me, funnily enough. It’s interesting.

Matthew Mottola: And then the podcast we’ve had to navigate, which you probably have – you get 200 episodes and you go, oh, we’ve had every guest possible under the sun. What do we do now? Do we bring on the same guests? Do we expand? So for us, the podcast has kind of become this source of truth. In some ways, it’s founder brand, in terms of it’s quirky in some ways. But then it’s also just a way to extend everything we’re already doing. On our platform, we see who the best solutions are, we meet with the best solutions every quarter, and the podcast is more about highlighting the best on the platform because we have the data from the platform. So it’s all connected.

Timothy Allen: I don’t have the problem of returning guests too much. I’m on episode – we’re nearly 200 now. I do have returning guests though, because I think it’s important to have them come on every now and then. There are news updates that need to happen. I think the most I’ve ever had anyone on is three times. We’ve been going four years. Once a year, we all meet at conferences or whatever, and it’s actually quite important to find out what’s happening. Because I don’t know about your industry, but my industry is moving incredibly quickly and evolving very fast. So it’s important. I even started doing news episodes recently. Every now and then if something happens that’s obviously affecting the world I revolve in, we turn it into a little bit of a news segment. But what I’m grappling with currently is knowing what to do next. Because I haven’t got enough time. I’m at that funny point where I haven’t got enough time to do too much more myself, but I haven’t got the inclination possibly to pay someone to come on and do it. If you see what I mean.

Matthew Mottola: I know exactly what you mean. It’s a funny situation. Because we did the opposite. We paid too much for the podcast to then gut it and put the money towards the platform. But it all comes back. So if you need a solution on our platform, I’ll pitch you after. But for us, it’s all connected to the greater vision, which is the transition to a flexible workforce. We actually don’t want to be a podcast and a media brand, but our industry is still so early that it needs those stories. Think about Salesforce before the cloud was even trusted. Salesforce had to be category creation. So they spent two years doing the craziest marketing stunts to get executives to just sign off on having CRM in the cloud. Our industry, at least, is still in that maturity.

Timothy Allen: Can I ask, at Human Cloud, do you spend any money on marketing other than the podcast?

Matthew Mottola: Yes. We used to spend 80% of our money on marketing. We now spend around 60% of our money on marketing. Mostly in-person has the best ROI.

Timothy Allen: Really? Like meeting someone at a conference?

Matthew Mottola: Yes, absolutely. Travel. In-person QBRs are by far the best investment.

Timothy Allen: What’s a QBR?

Matthew Mottola: Quarterly business results. So you have a meeting, everyone comes, you tell them about blah, blah, blah. Tell them how great they’ve done or how bad they’ve done, tell them where they can improve, but it’s in person. So you have that experience. The biggest thing we didn’t expect with AI is our developer costs have not had to majority go into that. So typically as a founder, when you go raise, your last deck says, hey, we need this amount of money to do these three things. And one through three is usually technical or developer-led. It’s now mostly distribution costs. So for us, we haven’t had to invest in a large developer team, which is new. This is new as in the last six months. We majority spend on marketing and on buyers, getting companies to understand what this industry is, why they need it.

Timothy Allen: But what does the podcast come under? Because I would call it marketing.

Matthew Mottola: I’d call it growth.

Timothy Allen: Okay.

Matthew Mottola: Because it’s kind of sales, right? And this is where the core functions of a company are changing so much. Is it marketing? Is it sales? I personally get queasy about marketing. To me, marketing means you’re going to sound good, but there’s no tieable ROI to it.

Timothy Allen: That’s just a word. For example, you and me talking now is marketing your company. But you don’t have to tell me about your company. I don’t care about that side of it. I’m interested to find out who you are. But obviously by finding out who you are, I find out what you do. So in a way I’m not cynical about it like that.

Matthew Mottola: No, I hear you. I would say if your company’s good, then it gets marketed. And I would say if you have a podcast where you interview everyone from your industry and it’s called the same name as your company, I would say that’s brilliant marketing. And I would say that’s the best marketing, because you’re basically getting to sit down at the table with anyone you want in your industry.

Timothy Allen: And we were talking earlier off camera – the kind of remote work world, the kind of flexible work world doesn’t really have an outlet, a media outlet. I’ve gone through this process with the Free Cities movement that I’m in. I’m that now. So I have become that. And I didn’t think about it much at the start, but in the last year it’s become really obvious. And that’s made me want to grow it. It gave me a kick up, made me think, oh yeah, someone’s got to do this. And I feel in a slightly privileged point, because sooner or later someone else is going to do it as the industry grows. Why the hell has the remote work space not got one? Because it’s a really big business, right?

Matthew Mottola: Yeah. I don’t exactly know, but I can confirm what you’re saying. For me, it’s been as early as 2012 I’ve been in the space. I’ll speak from the freelance side. Freelance had a moment. We’ve had about three moments. We had a moment in the Elance-Odesk merger, which created Upwork. We had a moment 2018, 2019, Upwork went public, Fiverr went public. We then had the COVID moment where both remote and freelance did. Now, last year, I can say that it was a terrible year for a lot of the freelance-related companies. And right now, the term freelance is more associated with an individual who’s working for themselves. It’s more of a lifestyle thing, not embedded corporate infrastructure. For us, I think the reason is – when you go into a mid-to-large enterprise, you don’t have a chief freelance officer. Because of that, you don’t have a dedicated budget. Because of that, you don’t have things funding a media channel or something of that nature. To me, the core reason is, remote work and freelance, they’re not the core technology. They’re simply accelerants to what’s already going to happen because of other technologies. What is freelance? What the hell is it? And who cares about it? It’s literally just a contract that says I choose to work as an independent contractor. And in hopes that means the government’s not going to sue you, the employer, for not paying my benefits and taxes. Now, you can’t have an industry called the independent contractor industry because it’s boring. Freelance sounds sexy, and it did sound sexy for a while, but it’s still not the core driver, which is, individuals want to work for themselves and companies want to hire people for their outcomes, not in a perpetual full-time employment contract. So that’s why I think it is. There’s not that embedded institutional structure that then has downstream effects of what creates a typical industry. Look at Salesforce, they have Dreamforce – because they had a company that was so successful that they could rent out a whole city to have a conference related to it. HubSpot, another one, they have their HubSpot conference in Boston. Hell of a time. There’s been no company that’s been large enough to foot the bill for a Dreamforce or something of that nature. Upwork and Fiverr have been successful. They’re not renting out a whole city to create a conference.

Timothy Allen: I was just about to say, I think if your industry has a conference, you should have a media group or conglomerate as well. Running Remote is a remote work, freelance work, digital nomad type conference. So it should have. I’m surprised. We cover it – I probably do, I don’t know, 10% of my episodes are about this kind of stuff, because it’s relevant. A lot of our listeners are thinking about moving jurisdictions, about being in different places, who treats you best, where do you pay less tax, where can I optimise my life. But yeah, maybe I should move into that a little bit more.

Matthew Mottola: Will there be a Free Cities conference?

Timothy Allen: Yes.

Matthew Mottola: When, where, and can I come?

Timothy Allen: Of course you can. It’s in Honduras on the 3rd to the 6th of September this year.

Matthew Mottola: Great plug.

Timothy Allen: It’s our fifth conference – actually, is it the sixth? The first two were a bit private-only. But then we’ve had four at least in Prague. And this year, for the first time, we’re going to an actual free city. Próspera. You know about Próspera?

Matthew Mottola: Oh, tell me more.

Timothy Allen: Próspera is an actual free city in Honduras. It got regulatory autonomy from a change in the Honduras constitution a number of years ago. So lots of biotech firms are going there. Fringe industries are moving there. You can live there. You get all the tax benefits of living there. You can start your company there. I’ve just lived there for a month. I came from there to here. Gonzalo is living there. You know Gonzalo. He’s living there at the moment. So yes, we’re having a conference. But going back to what I was saying about this space, it seems like there should be something a little bit more substantial to cover the space, to be the media outlet. I’m wondering whether what you do is – or are you not specific enough? Who do you interview on your pod?

Matthew Mottola: It’s a really good question. We interview the best executives for talent platforms. There’s thousands of them, and we interview the executives.

Timothy Allen: So talent platforms – that would be very separate from say the world of digital nomads. They’re not on talent platforms.

Matthew Mottola: And the answer I have – this is me being too transparent as a founder – there’s not enough money on the individuals. My prior company was actually an operating system for freelancers to run their business, build their business. And to put it blunt, there’s just not that much money in that industry. There’s enough for taxes – there’s Collective and others that do solopreneur taxes and finances. But in terms of as a group, the individual freelancer segment is massive, but – I don’t know if we want to get too geeky – the actual GDP discretionary income is not that high. Whereas there’s over 140,000 staffing firms predominantly making between 10 and 30 million a year. And there’s five that are really, really huge. So the staffing industry is huge. The solution layer is huge. We specialise in getting the better solutions. So you come to Human Cloud to find the best solutions, not to find the best freelancers, individuals, because our belief is the scoping is so damn hard. You’re going to need these solutions. Now back to your question related to the media. Here’s the contradiction we have. When we do best – and I’m speaking for the industry – when the flexible talent industry does best, nobody knows who we are. It’s missed. Nobody knows that we’re even there. And that’s the point. The goal is not everyone to know about freelance flexible work. The goal is for the CMO to create the most amount of pipeline or views they’ve ever created because flexible talent enabled them to build out the campaigns, the Super Bowl ads that enabled that to happen. So we have an inherent contradiction in that we succeed when nobody knows about us, which from a media perspective creates a nightmare because the best leaders don’t want to talk about it. They simply want to be the best CTO, CMO, COO, CPO, whatever it is.

Timothy Allen: Is that true? I thought – Diary of a CEO, things like that – CEOs love blowing their own trumpet.

Matthew Mottola: They do, but they don’t want to talk about our world. They want to talk about their own company. They don’t want to say, hey, how’d you create the best podcast in the world? Well, other people did the work. How’d you create the best operating system? Oh, actually, we had the best freelancers. It’s a secondary point. It’s not the core driver of what the best companies want to talk about.

Timothy Allen: But you are speaking to your client base. If you are in a world of freelancers, I would say they’re not a disparate – well, they are quite a disparate bunch, actually. They’re not connected necessarily.

Matthew Mottola: This is a core problem. I’ve learned in entrepreneurship, it’s easier to identify what you need and tell you what you need in your language, rather than to try to define to you what I think you need and have you believe my world. I don’t want to do that. I want to identify your problem and I want to give you a solution that you don’t have to even learn. It just solves it for you. Freelance is very inherent to what most leaders want. Most leaders want a loyal bunch of strong outcomes and a workforce that when they say, is it done? The answer is yes. Freelance, historically – and there’s been some books that kind of ruined this – they brag about being on a beach, working four hours a week. No executive wants to hear that. Executive wants to hear that it was the best ever campaign done on time, on budget. Now the best freelancers are the ones that are on time, on budget, and usually not talking about it. So there’s the contradiction there. The last thing I’ll bring up, and this is very related to you – if you can figure out a way to make independent contracting work free, fair, and predictable in that governments aren’t going to sue me, then we would have a much easier world. The reality is, if I go hire let’s say a thousand freelancers and I pay them over a hundred million dollars, most governments are going to come back to me as a company and try to make sure I paid my taxes and get me for misclassification. So there’s also a lot of legal risk that is so boring that also exposes companies, and companies don’t want to talk about it. Kind of like – they don’t let you know that they actually are staffed by over half contractors. Like Google doesn’t show off their 60% contractors. They don’t have ads talking about that.

Timothy Allen: I suppose the interest I have in it is in the freedom aspect. This is why I’ve always been a freelancer. I’ve never had a job, so to speak. I’ve always worked for myself. And that doesn’t mean I necessarily dropped everything at the drop of a hat. I don’t think I ever did that. I was a very loyal freelancer, so to speak. Never as an employee, but as a freelancer. So that’s my interest in it – the outcomes that help show that’s a good outcome, that’s what I’m interested in. Same with digital nomads. I like digital nomadism because it allows people to find the best place to get the best life and hopefully still do what they want to do. I like freelancers for similar reasons. It gives them the flexibility to say yes or no if they want. It gives them that freedom. So that would be my take on it.

Matthew Mottola: And I agree with you. So I match both worlds, because I started freelancing, I fell in love with this concept of it. And what is best for the company and the individual – you are so good that you’re willing to work based off your outcomes, and you’re willing to allow that employer to fire you whenever they want, rather than having to worry about severance and all the things that can get them in trouble. So you are so good that you’re willing to put your employment on the line to not take what I just call is a perpetuity contract or a permanent contract. And that’s because you’re so good. Now there’s a lot of connotations. If we’re talking about freelance because I get to work whenever I want with who I want, true. But the reality is, it’s also because you’re so good that you’ll commit to the outcomes.

Timothy Allen: Yes, I do agree with that. Not that I’m saying I’m so good, but that it’s a free market of work. And I like that because I feel competitive. If I didn’t feel competitive, I would probably want to get a job where I could lock it in forever. But I wouldn’t want to employ someone on those terms necessarily anyway.

Matthew Mottola: Exactly. It’s one of the flaws in the system. But it’s been easier to do that, right? It’s been easier to say, hey, I would rather have a team of 100 people that I can just go, did you do this? And I know they’ll do what I say, even though they’ll only do 10% of what I say, rather than having to go, okay, I need to get something done, let me fish out in the free market and have to worry about this person who’s going to say yes or no. Now, it’s not that difficult. You and I know that’s not the case. And one of the biggest myths is – freelancers, people believe they work with new clients all the time. You probably work with the same clients over and over and over. And that’s just something most people don’t know. So tying to the beginning of the episode, we tell the stories that shatter the myths that get in the way of companies hiring freelancers and hiring flexible work. And that’s one of the biggest myths. If I could take magic and put it into a company’s brain, it would be that myth of, hey, that freelancer is probably going to work with you longer than any other tenured employee you have.

Timothy Allen: Do you know what though? Just to put a little spanner in that works. When I was younger I was a freelance photographer. I ascended very high up in the ranks of photography. And what I noticed was, I was a very loyal freelancer. So I had my magazines that I used to work for, and they would always call you up. And you didn’t know what you were going to do from week to week, but your weeks were always full because you had a roster of people that always wanted to employ you. And suddenly I noticed in a couple of the places I worked, some younger editors came in. And all of a sudden, why isn’t the phone ringing? You phone them up, they’ve got their person in. And I remember it shocked me the first time. It was an age thing. It was moving to another generation. I said to one of them, why did you decide to pick someone else? And they said, oh, I just thought we should have some fresh talent, have a change. And it was almost like, I know it was for the sake of it. It was for the sake of having fresh talent in, because they were getting a killer product from me and other freelancers I knew. And it was exactly what all the staff wanted. But they were new people in the job and they thought, I know, let’s do this. And they were younger. And they certainly didn’t understand the unwritten agreement that was the nuts and bolts of all the relationships I’ve ever had. I don’t think I’ve ever signed a freelance contract, to be honest. Honestly, I worked at a national newspaper in the UK for seven years. I never signed a single thing.

Matthew Mottola: Let me ask you this question. If the company now, today, right, 2026, you are running Microsoft and you had over a billion dollars of that, what would happen to you?

Timothy Allen: I’d go straight to the Seychelles and just live out my days there. No, I have no idea.

Matthew Mottola: You’d have a group of lawyers getting ready to have this classification lawsuit and you would owe 30% of that.

Timothy Allen: It wasn’t that long ago that we were living like this. This is like late 90s in London, working at newspapers, literally not signing anything for years. I didn’t care. I didn’t want to sign anything. I just knew that I was going to call every morning from a picture editor and say, go here and shoot this. And that could happen seven days a week if I wanted.

Matthew Mottola: Now, here’s where I’d say it’s different – when you have a developer, it’s more static, in terms of you might have worked 40 hours a week for five years, and it’s easier to prove this person’s not working on a gig freelance fractional basis.

Timothy Allen: Oh, okay. I’m not going anywhere with it. I’m just pointing out the fact that I come from a world of just gentlemen’s agreements. And often you didn’t even shake on stuff. You just, yeah, sure. Like, you come and work for me and I’ll pay you at the end of the month kind of thing.

Matthew Mottola: Do you know what shook the industry? When I started at Microsoft – so when early employees were determining their compensation package, they were offered two directions. This way, higher cash, no equity. This way, lower cash, equity. Now, they knew what they were getting into. It was not like they didn’t trick them or anything. Microsoft goes public. And there’s the employees who took option number two, which was high cash, no equity. And who shows up? The lawyers. And what do the lawyers say? Oh, you got mistreated by Microsoft. Your friends now have mansions and Lamborghinis and you’re stuck with your Honda and single house. And the employees go, yeah, you’re right, they did wrong me. Okay. Misclassification lawsuit, $99 million, massive brand hit. And that’s what kind of drew out a little bit of this industry. So that’s where, if you can make free cities work, then a lot of this industry will not be that much of a problem. And it could be a cooler, sexier industry.

Timothy Allen: Well, okay. Free cities, fortunately, are actually currently working. In Honduras, it’s happening. That’s a whole other podcast. I’m going to finish. I just got one last question, because I’ve asked everyone this. Simple question, not a simple answer. What is the future of work?

Matthew Mottola: Oh, that’s a deep question. I mean, I hear it a lot here. I was looking at who’s speaking and it’s like, who is this person? Oh, he’s into the future of work. I’m like, wow, what’s that, flying around in spaceships? I’ve been asked this question since 2012.

Timothy Allen: Okay, come on. Hold on a minute. When you answered in 2012, what did you say about 2026, and did it happen?

Matthew Mottola: I would say until 2023, actually 2024, I would have said the world’s going to look a lot more freelance. That’s what I would have said. I have a different answer now, but it’s directionally similar. I would say the world’s going to look a lot more freelance. At the time, my freelance looked like what you’re used to – I’m working on a project basis based off my outcomes with the clients that I choose. Now, what’s happened is that word, I think, has been a little bit too ambiguous, so it’s not as specific. To me, I do think the world’s going to become more agentic. I did not think this six months ago.

Timothy Allen: Hold on a minute. Agentic. I keep hearing that word. As in AI agents doing things. Is that what it means?

Matthew Mottola: I define agentic as job descriptions. What I mean by that is they are simply simple, stupid processes that anyone can build, but they still require oversight and ownership and iteration. So I call them job reqs, just because they are no different than bringing on an employee. That was the purpose of a job req – hey, I’m over capacity, we need to do something, let’s get a job req. So I think it’ll become agentic. I wouldn’t have said this six months ago. And I was early in 2016 when you’re making money on Bitcoin and crypto – I was dealing with deep learning, neural networks, machine learning. This was pre-pre-generative AI. Working in this way, I don’t see it ever going back. It’s such a game changer. So I see the world becoming agentic. I see it becoming specialised, meaning you can’t just show up and say, hey, I’m a salesperson. You better be the best at whatever it is that you love. Best in something like automotive in North America, energy in Malaysia. Highly, highly specialised. And the third is outcome-driven. So it’s not enough to show up, say, hey, I need 150K a year for a marketing job. No, no, no. You need to be agentic, meaning you have to bring your agents. You have to be specialised. I’m not just marketing. I’m actually the best in this industry, in this region. And you better have your outcomes ready. So rather than just pay me 150 because I’m too lazy to figure out the exact outcomes, it might be, hey, we’ll do a month engagement, and I believe these are the metrics I’ll hit. If hit, we keep going. If not, we move on. So those are the three things I see.

Timothy Allen: That’s interesting. Advise my three children who are still too young, but eldest is 14. I’ve just had a conversation with my daughter actually back home, my eldest, she’s 14. I said to her, look, Alice – because I’ve been speaking to her for about a year and a half about university. I used to be, yeah, maybe you don’t need to go to university, but I went and it was good fun and blah, blah, blah. And I’ve just been on the phone to her this time. And I said, look, Alice, I’m going to tell you now, because I’m in the thick of it here, I’m talking to people that know about this stuff. You do not need to go to university. This is what I’m going to advise you. You’re going to take a year out at 18, and I’m going to set you up with some fun things to do. I’ve got friends, you can go work in Austin or whatever. And then after that year, you’re going to decide whether you want to go back. I don’t want to force her or tell her, no, you’re not going to university. But it does seem like this shit is really changing massively fast. And the way you’ve just described it there, I’m thinking, how do you get into the market now? Well, you choose your market and you go out and you make some shit in your backyard, at home, in your home office. You design some apps, you create some stuff, you start an Instagram account, you get 20,000 followers. That’s what you take into your job interview now.

Matthew Mottola: Let me bring up university. What pisses me off so much, the people who used to say you don’t need university, ask them, where’d you go? Most of them went to Stanford or Harvard or you name it. Then the ones that would say, oh, I didn’t go to university. Oh, really? Wait, where’d you start? Oh yeah, I dropped out of Stanford, Harvard. So that part pisses me off. There’s always like a, you don’t need to go to university. Oh, really? Where’d you go? Now, this is where I do think it’s changing. I think the idea of university is, you have intentional time to fuck around. Now, fuck around, I think, used to mean you would have the most impressive professors to really harden what you believed in and basically just teach you stuff that you wouldn’t know if you were self-directed. So I went to a school called Babson College, and I think it still kind of follows this principle. Our professors were not giving us generic knowledge. They were saying, go solve massive problems. And we were the best in the world at our businesses. So my professors were not like generic professors. They were ex-CEOs, they were ex-VPs. Different world than, hey, I’m going to go to a school to major in something everybody else next to me is doing and get a 99 on what everybody else is doing. So I think universities are flawed in that way. With that said, I think what will always be true – one part’s generic, one part’s I think against the grain. Do hard things. So don’t just sit on your couch and eat potato chips. If you love rock climbing, go nuts at rock climbing. If you love nature, figure out every plant possible. If you love to code, figure out the science of coding. Go nuts on being and doing really, really hard things. The second is, don’t discount affiliation. And what I mean by that is, we do love brands. As much as we act like, oh, it didn’t matter where you went to school, it didn’t matter where you work. When I tell people I worked at Microsoft versus I tell people I had a startup that nobody knows about, Microsoft speaks. I don’t think that’s going to go away. And so my two things are, do really hard things, but then still look for affiliation. Don’t be totally on your own. I don’t think most people are saying that. And I may be wrong with it, but I think we’re always going to be brand snobs, even if the world is insanely democratised, decentralised, you name it. What do you think?

Timothy Allen: No, I appreciate it. For example, the UK university situation is slightly different to here, but in the same sense, I’ve always said to my kids, look, don’t bother going to university unless you get into Oxford or Cambridge.

Matthew Mottola: What I’m talking about. Affiliation. Do hard things. If you’re going to university, go to the best. Don’t mess around.

Timothy Allen: And there’s two reasons for that. Number one, in Oxford or Cambridge, or maybe Edinburgh or one of the other ones, you will rub shoulders with people who will end up running the country. That’s kind of what happens, rightly or wrongly. There’s nothing wrong with putting yourself in a room full of those people. Number two, if you’re in Austin and someone says, where do you go to uni? And you say Oxford, they’ll go, oh, I know that. But they won’t know Birmingham University or Leeds University. They don’t care. So I don’t think that’s worth it. I don’t think doing business studies at Leeds University is worth it. I do think doing anything at Oxford or Cambridge, Harvard, is worth it.

Matthew Mottola: And here’s another thing. Listen, I don’t have kids yet, but it’s something we always talk about. My wife and I are polar opposites. I’m very entrepreneurial. I’m okay jumping into something knowing nothing and having to figure it out. My wife is the exact opposite. Who would I rather employ? My wife, 10 times out of 10. She’s a dentist. All her families are doctors. They did really hard things in studying dentistry, totally different path. So I do worry when – I remember I heard this, it was a founder in the space and he’s like, well, in the future, everyone’s going to be entrepreneurs. And I cringed and I was like, why am I cringing? If everyone was entrepreneurs, we wouldn’t have Bell Labs, Xerox PARC. A lot of great things were developed by scientists who never thought to themselves, how do I sell this? They fucking loved what it was they were doing. So that’s my only other contrarian point. If you want to be a doctor, unfortunately, you’re going to have to go to school and study, but you’re going to have to get into Oxford and Cambridge.

Timothy Allen: Well, not necessarily with doctor. But this same daughter originally wanted to be a vet, because she rides horses. But I wonder whether that whole world isn’t getting competed away. Talk about AI taking over. If we’re getting driven around in driverless cars, then people are going to do medicine without humans as well. Especially stuff where they cut you open. Of course, a robot’s going to do that. I’ve watched the way the Waymos are driving. It drives better than me. It takes what I think is a risk, but it’s not. We were going to pull out this morning coming down here. There’s a freeway. We’re about to pull out onto it. And I looked at the gap and I thought, I wouldn’t do that. And it did it. Of course it did, because it knew exactly what was going to happen. I don’t, you know. And the same will be true if I got operated on by a surgeon. I think the AI robot arm is going to do a better job of the surgeon, probably.

Matthew Mottola: Let me throw a question at you related to free cities that you’re going to have to answer. And the answer might be, your question is stupid and it doesn’t matter.

Timothy Allen: Go for it.

Matthew Mottola: My question for anything related to automation, driverless cars, getting rid of doctors – well, it’s a really boring question. Who do I sue? And that question unfortunately drives a lot of the world we see. Because why did driverless cars take, what, 15 years to hit the road? Not because it couldn’t do it. Mostly because we didn’t figure out who’s it going to sue. So that’s my cynical brain. If you figure it out in free cities, then there’s the answer.

Timothy Allen: Well, in free cities, you basically create the free city with such legal solidity that you don’t actually have this problem. And this is just played out in Honduras. The famous Honduran free cities, of which Próspera is one, have basically tried to be shut down by socialist governments, and they had such robust legal networks set up to protect them, including bilateral international agreements and everything, that the socialist government failed. And that’s a big deal. That’s a massive deal. They actually wanted to shut them down and they’re ideologically opposed. So that would be the thing. And Próspera and most of the ZEDEs were literally set up by lawyers. That’s really how it works. They changed the constitution of Honduras. It was a lot of lawyers getting together saying, how do we create a place where we’re not going to have problems? And in their answer, for example, if you want to go live in Próspera, you sign a contract to live there. Here are the rules. You do a service provider. You deal with the service provider. It’s like, you can do this, you can’t do that. And that’s it. It’s zero.

Matthew Mottola: So let me tell you an experience that might be an episode for later. For me, I grew up in a small town. Grew up my whole life there. Had zero problems. Never had house keys. Knew my neighbour. Loved it. And I would argue it was the perfect utopian city in that way. Got older. Went to San Francisco. It was kind of a shithole. Homeless people. Not exactly run well. Moved to Singapore. Have you been to Singapore?

Timothy Allen: Of course. Many times.

Matthew Mottola: Now talk about a mental mind twist. In some ways, it’s the socialist utopia. In other ways, it’s the capitalist utopia. And there was one example to me that kind of says, this is the way the world should go, but I don’t know if this is the case. The incentives for healthcare. I could twist all my conservative friends and liberal friends about this. You’d go to the gym, you’d see a QR code. You scan the QR code. What does that mean? If you go five times a week, you’re going to have cheaper health insurance. Singapore had aligned incentives in a way that was best for the society. And I would argue it was great.

Timothy Allen: Of course. It’s a trade-off. You can get put in prison for crossing the street in the wrong place, probably. Or dropping chewing gum. It’s an incentive. Dubai has the same so-called problem. Dubai is incredibly safe. Well, what’s happening now is slightly different, but if you go Dubai pre-Iran war, incredibly safe. A lot of people love it there.

Matthew Mottola: But no, you lose free speech. That’s what my friends say about Singapore.

Timothy Allen: Right. But it’s a trade-off. I don’t mind that providing it’s voluntary. That’s the whole thing for me. It’s voluntary.

Matthew Mottola: Is it voluntary? Explicit and voluntary.

Timothy Allen: Yeah. And hence, in the case of free cities as well, you would add on top of that a way to independently adjudicate things that you need to adjudicate. In a free city, instead of having a government, you have a service provider who provides the governance. But in Singapore, if you want to sue the government, you can’t, right? In a free city, you can, and you go to international arbitration. So if you have a problem – if your contract says you can build this high and they’re saying you can’t, then you can now go to an independent adjudicator who will look at that, and it will go with the truth rather than having a relationship with the government. So that’s the difference. But to be honest, for me at least, they’re all degrees of sovereignty. They’re all degrees of incentives. What I want is, you to be able to choose. A bit like the federal system here. You didn’t like San Francisco? Heck, you can move to Austin. You can do a lot of stuff in Austin that you can’t do over there, and vice versa. You don’t like the way it’s governed in Austin? Maybe you move somewhere else.

Matthew Mottola: I got a question for you about that though. So I love San Francisco in this way – well, let me copy it, not in this way, because if you clip it I’ll sound like a monster. So you walk down the street and you see somebody passed out. You see someone doing open-air drugs. It has gotten better, I will say, in the last year. But that’s the way it was. Now in the same realm, you have this crazy, innovative, creative streak that, if the rules were explicit like a Singapore, I don’t know if you’d be able to have that level of innovation. So part of what I loved about SF was, you’re so creative and just thinking about how to change the world, you don’t even look down to see that there is someone passed out on the ground and then someone doing open-air drugs. It could be –

Timothy Allen: That’s fine. What you want is a lot of those places all competing with each other. You want a free market of governance. You want badly run places and good run places. And like you say, for all intents and purposes, in that sense San Francisco isn’t badly run, because it allows the space for intense creativity and innovation. So yeah, I don’t mind at all. What I want to see are lots of competing places. That’s why I like the federal system. You’ve got a lot of states all competing with each other, and we’re seeing it actually work. People are coming here, they’re leaving other places. So for me, yeah, more and more of that. What I don’t like is where you don’t get that option. And obviously opt-in, opt-out. It goes without saying. You can’t be forced to stay somewhere. So opt-in, opt-out.

Matthew Mottola: So it ties to the beginning, because to me, freelance equals the most – I would say least – layers of abstraction to choose the impact and outcomes that you want to do. And in return the employer gets to choose the impact and outcomes that they want. That’s all it should be.

Timothy Allen: Hopefully, exactly. A free market agreement between you and them.

Matthew Mottola: With a contract. And it gets a little complicated. Because a full-time contract to me is the riskiest but laziest thing we have. We don’t look at you as an individual. We look at you as a pay band. We look at you as a comparable to what you would charge if the company next to me. And it’s lazy just in terms of it’s not exact. Software is exact. So to me, there’s so much room in employment to get rid of this abstraction, get rid of this just laziness. And we’ve got a lot of work ahead of us.

Timothy Allen: We have, indeed. Matthew. And you got me. I’ve got too many names written down here. I’ve spoken to seven people today already, mate. Tired. Intense. I’ve got a bad neck. Thanks for chatting. That was really interesting.

Matthew Mottola: Thank you. It was fun.

Timothy Allen: Really interesting. I like your perspective. Obviously, it’s relevant because – how do I consider myself? A freelancer? I suppose I am. I haven’t said that word for so long.

Matthew Mottola: You’re self-employed. You’re not working on a full-time perpetual contract.

Timothy Allen: I think these days I would call myself an entrepreneur, I think. Because previously, I do create things that are nothing now. Whereas before, I used to look for a market and then go and freelance myself. The original word comes from lances for hire, doesn’t it?

Matthew Mottola: It’s a great way to describe it.

Timothy Allen: When I was a photographer, I had my equipment and I would go and say, I’m for sale, I’m for rent, who wants me? I’ll fight for you. I’ll fight for your team. That’s basically what it’s like. Whereas now, entrepreneur seems a better idea, because I didn’t go to anyone and say, do you want to hire me? You make something and then it’s in the market. Or you even create the market sometimes.

Matthew Mottola: To your employer, you are the best podcast. They don’t care what you call yourself. It’s the impact that you make to them. Hopefully this world to – agentic, specialised, outcome-driven – for some, it’s incredible. I think in the free city movement, it’s aligned.

Timothy Allen: Bravo. Well, thanks a lot for chatting. It looks like we’re getting to the end of the day as well, which is great.

Matthew Mottola: Let’s get some coffee.

Timothy Allen: Yeah, let’s go and get some coffee. Nice one. Nice to speak to you.

Matthew Mottola: Of course.

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Notes:

Speaker labels were reconstructed from context because the Matthew/Tim source transcript had timestamps but no speaker names.

Timestamps, repeated fillers, obvious false starts and ASR line breaks were removed for readability.

I preserved the meaning, voice, swearing and main order of the conversation, but unclear names or phrases from the raw ASR should be checked against the audio before publication.

The Veritas Villages sponsor read at ~13:14 of the audio was omitted from the conversation transcript.

No external fact-checking has been applied to factual claims made by either speaker.