Fractional & Freelance Opportunities in the Enterprise Space w/Matthew Mottola

Brett Trainor (00:02.17)
Hey Matthew, welcome to the podcast.

Matthew (00:04.578)
Thanks for having me, bud.

Brett Trainor (00:06.17)
Hey, no, it's good to have, uh, I know we've been pushing it back or I pushed you back a few times, I really appreciate the flexibility, but I think the timing is perfect to have you on to talk all things freelancing and enterprise. And I know this is your world. So three things I'd want to, I'd like to chat with you about today. One is just a little bit of background on yourself and human cloud and what you guys are doing in the freelance and enterprise space to man, any macro trends.

that we should be aware of. And then three, let's get into some best practices for folks that are thinking about freelancing in the enterprise space. And then of course, anything else that you wanna touch on, I'm open game. How's that sound?

Matthew (00:44.95)
Sounds perfect, man. And I think the theme of we waited for the right time is actually so perfectly analogous to freelance and why it's so important, because we didn't need months to produce this. We knew we needed probably a turnaround of hours. And so we waited and we said, okay, now's the right time, strike.

And freelance is the same thing, right? It's when you need the talent, not necessarily always having to have full-time FTEs. We'll talk about it later. But so just want to make sure I called that out, that it's very analogous to us waiting until the iron's hot.

Brett Trainor (01:13.894)
Yeah.

Brett Trainor (01:17.97)
That's awesome and a perfect segue man. You led me right into that. I didn't even think of that. I'm a little mad now that we didn't come up with that. But anyway, so why don't you just tell the audience a little bit about yourself and a little bit about Human Cloud. I mean, John was on the podcast six, eight weeks ago, maybe folks probably remember. But I think it would be important just to kind of set the stage why you are the expert in this space and why I think we're gonna get a lot of value from listening to you.

Matthew (01:24.798)
Sorry.

Matthew (01:47.946)
Yeah, of course. Well, first of all, thanks for having me. Yes, John is our company better half, I would say. So HumanCloud, we're an advisory firm for the industry, specifically the freelance industry. We've been in this so long that we're able to help leaders, whether it's enterprise leaders scaling a freelance workforce or the platform leaders themselves building.

building their solutions. So I like to joke, I just say purely advisory, but the reason for that is we really genuinely love the space and love the leaders pushing it forward, people like yourself, Brett. And quick on myself, because I think it'll give you context. So like I mentioned, I've been in it for 10 plus years, started as a freelancer. I was early at Gixter, one of the leading solutions, building custom software dev through freelance networks, built Microsoft's product in the space, helped scale their freelance workforce up.

built the venture back company helping freelancers themselves, sold it in 2022 and now leading Human Cloud. So it's kind of all percolated together. We also published a book called The Human Cloud in 2021, I think, with Hartford Collins. So yeah, we published it right when COVID hit. Yeah, yeah.

Brett Trainor (02:53.818)
Yeah, no, it's perfect, right? So long time listeners or even recent listeners will know I'm a huge advocate for the SME, SMB startup and nonprofit space is a good place to leverage their talents, freelance, fractional, whatever you want to call it. But I know there's a huge opportunity in the enterprise space and I'm not as well versed of that opportunity. Like, well, Matthew's the perfect person to come on and talk about it. But, you know, before we get there.

You know, we were talking a little bit offline again, should hit record before that was, you know, the corporate world's on fire right now. Right. I wrote a little something or talked about a little bit yesterday with more and more layoffs. You've got, um, the returned office mandates, which some people are saying that's quiet way of firing, but man, if you're doing that, you're going to lose the wrong people. I think so. I'm not a huge fan of that strategy, but you know, it opens up the world for, for freelance. So.

What are you guys seeing, you know, either micro or macro trends? Where, what can we look for? What are the opportunities here in the next couple of months? You know, 12 months, 18 months. What are you guys seeing?

Matthew (04:02.142)
Yes, let me first define when we say enterprise. So I think one of the myths is when we think enterprise, you think very large. So Fortune 100, Fortune 500s. That's definitely true. But I think it's more so that we're talking about scale. So we're saying instead of just, hey, hire an individual freelancer, we're talking about the scale of spending a million plus a year on freelancers, which typically is a product of spending a lot more already on external talent.

So I just want to make sure to make that clear, right? When we say enterprise, we're really just talking about scale of freelance being a strategic sourcing channel. So that's the first thing. Um, the second thing is as an industry, freelance is necessary, is not necessarily immune.

to the enterprise versus startup timeline. What I mean by that is generally startups are like five to 10 years ahead of what the enterprise is doing. So for example, if you look at cloud adoption and you look at various technologies, if it's happening in startups or it's happening in small businesses, it will happen in the enterprise but a lot slower. And so generally what we've seen in freelance is that a lot of the models, be it marketplaces, be it niche marketplaces, be it fractional, other solutions

they're gonna get to the enterprise, but they're gonna be slower and they're gonna need validation in order for the enterprise to actually adopt this because enterprises really are trying to mitigate risk. And so for a small business, it might be a little slap on the wrist. For an enterprise, it's gonna be something massive. So, you know, having that base, right? If this is what enterprise is, this is sort of the timeline of enterprise versus small business adoption. What we're generally seeing is that freelance as a space, and we use the word freelance, you know,

the definition of any of this. We know it's one external talent, two digital mediated, meaning that there is some sort of technology layer directly connecting the person that needs the talent with the talent, right? So let's apply that very broad definition. But so when we look at freelance, we know there's been 30% to 60% adoption year over year up until probably 2016. Not to get too geeky, but if you look at the industry, 2016 is when Elance and ODesk merged to create Upwork.

Matthew (06:12.334)
you start to see Upwork and Fiverr IPO. Over the past couple of years, we've just seen a massive wave of new solutions, new platforms, really just driving this industry forward. So in general, there's been a massive wave. And that massive wave has been the shift from full-time being default to more freelance and flexible models. Now, it usually gets a little sticky because people say, okay,

Are we talking about the rise of freelancers? Are we talking about the rise of freelance spend, which spend equals demand, right? Freelancers equals supply. And being in this space long enough, we usually look at demand to say where the industry is going, because the value proposition of being a freelancer fractional is just so obvious in terms of it's so obvious that someone would rather be a thriving freelancer and fractional than not. But it's tough to justify the demand.

Brett Trainor (06:41.647)
Yeah, interesting.

Brett Trainor (07:05.478)
Right.

Matthew (07:06.432)
seeing is that space as a whole is growing. There's certain waves creating that, but what's really moving the needle is going from freelance being just a transactional, hey, we need someone to plug a hole or to do something small to being strategic. So, for example, for you and I, is this CMO or this director might be

Just as good, if not better, in a fractional capacity. Fractional meaning two days a week, or fractional meaning 20 hours, or fractional meaning just owning the strategy and outcomes and running the contract as without. So, and it has a very long-winded answer, but to kind of summarize it up, enterprise is usually just lagging from what the startups and small businesses are already doing. And in our space, that's a thousand percent true. And that sort of wave is freelance being from transactional to strategic.

Brett Trainor (08:00.946)
Yeah, interesting. It's such a good point to a couple of things. One, you're right on the adoption, right? Because there's still I still hear companies arguing about sales and marketing alignment. Right. And that was pre digital transformation. So they haven't even transformed their business to be more of a digital first, let alone start. How do we build a flexible workforce to support it? Right. I'm sure there's operating units that leverage it. You know, one thing and when we were talking before, I think what I was on your podcast, we talked about

the different role, right? So when you think about the employee, you know, it's kind of command and control. The organization will tell you it's not. Then the, I think the original freelance was more of a transaction, right? Hey, I'm going to pay you to do these 10 designs or I'm going to pay you this, but what, what fractional is come to do is really more of a partnership, right? I mean, it's got to work for both sides. It's not just, I'm paying you to do one thing. I'm becoming part of the decision-making process to help you do this.

And so maybe I'm getting a little tactical, a little quick, but I'm just curious from the enterprise, are you seeing different relationships or is it more still the transactional aspect of the freelance or is it starting to open up and expand to different relationships?

Matthew (09:16.95)
So it's a really good question. And just to summarize it, sort of what is the relationship between freelancer, freelancer and employee or leader? You know, the biggest problem in our space, and I know this is gonna be a kind of answer, the biggest problem is there's no standard adoption. What I mean by that, it's not like we have one sort of ideal customer profile and an adoption plan and comparables to look at.

It's not like digital transformation, right? Or cloud adoption or cloud migration or building a website, right? There's no best practices here. Generally what happens is that you have a bunch of, I would still call them early adopters, meaning you have a bunch of leaders that are very creative, very innovative and willing to just try something that the rest of their org might not understand. And so you might have a CMO that's saying, hey, we've always gone to the same vendors. We've always gone full-time or the same vendors.

and I met this great platform, or I meet this great individual, and they wanna work as a freelancer, let's just try it out. And instead of having a plan and saying, we're gonna do step one, two, three, four, five, six, seven, eight, and this is how we're gonna do it at scale, they're generally saying, okay.

to help us, right? Help us, help us. And so what you see is this kind of unorganized adoption where you have multiple parties and the multiple parties kind of seem like islands unto themselves. And one party is gonna be the freelance marketplace. One party is gonna be the freelancer themselves. One party is gonna be the existing vendors, be it vendor management services or MSPs or the other existing external talent people.

Brett Trainor (10:31.271)
Yeah.

Matthew (10:57.086)
And it's going to be very confusing, right? But freelance, what will usually happen is that there'll be a couple really good outcomes or a couple sort of bullet points to put your hat on. And one of those bullets is going to be the cost efficiency. So this person did this in six months. It prior would have taken us two years. Wow, look at that cost efficiency. It might be the speed. For example, we were able to get these individuals building our graphics, driving the plan, helping us with PPC ads,

Brett Trainor (10:59.918)
Yeah.

Matthew (11:26.98)
such, we were able to get them in the door in two to five days. You know, and then the third is usually something related to relevant skills. So, wow, we can have, and I'm going to give you like a last year answer. We can have a blockchain expert, right? We can have a web three expert nowadays. It's we can have a generative AI expert. There's no way we would have been able to find this person to help us out with any other model, except for a freelance model.

So in terms of what's the relationship look like, I say all that just to tell you, it's still a case by case basis. I can tell you when it works well, is typically when the leader kind of defaults to allowing the freelancer slash the freelance solution to define the terms, and the terms are generally, let's work on a project basis or an outcome basis. You're the expert here, I'm not gonna tell you exactly what to do.

Brett Trainor (11:52.665)
Raise.

Matthew (12:18.698)
And what really works well, what we've seen, and this is like in the past three months, is there's an understanding that the incentives are aligned in a better way than most full-time engagements. So for example, if I'm gonna bring a fractional person, or I'm gonna have a team of freelancers,

they probably are going to deliver just in terms of their incentives. They're higher incentive to deliver in a way that exceeds my expectations because that's what gets them the next contract or that's what gets them the next retainer or whatever it is. So in general, that's where we've seen it work really, really well. And this is, I don't wanna say new, but there's higher understanding of this that.

Brett Trainor (12:51.302)
Right.

Matthew (13:02.63)
freelancers seem to have a better incentive or not seem to technically have a better incentive to exceed expectations than existing structures.

Brett Trainor (13:13.166)
Yeah, no, I think that that's a really good point. And the fourth one I would have added is risk mitigation too, right? Cause if I'm a full time, I have to hire somebody full time, that's a 12 to 18 month bet I'm making on this, this individual. It's going to deliver those roles, right? The more senior, the more technical you better get that right. Maybe you make a change in six months, but you know how slow the changeover is by the time. So, um,

And there's a good point in there. So if folks in the audience are thinking, I'm like, all right, well, I can come in. I see opportunities in the enterprise. I'm still there, right? Maybe transitioning from a full-time and I start to look for opportunities. I think the advice I'd give you is go in confident with different engagement types, right? You can meet them where the business is, but you know, as Matthew just said, they don't know. So if you can go in and say, Hey, this is how the best.

how my best engagements work or what we're starting to see in the industry is fractional. Man, it's a day, a day and a half a week focused on these core things. You know, we meet once a week, we work and just kind of outline what the best practices. I think you're going to have too often we come in, you've got a business leader in the corporate that's like, yeah, I need help, but neither one of them knows how to approach it. And it doesn't, it usually doesn't end up well. So, so be confident is how you're going in there. And

be open, right? To your point, I think there's multiple ways to structure it, where these will make sense. I think the key is to make sure it's a partnership, try to treat it like a partnership versus, again, I don't, I'm not a huge fan of the transaction and definitely not the, the commander, command and control type of a model, but that's interesting.

Matthew (14:52.426)
And here, I think this will help. So, you know, the only advice that I would give both the freelancer, but also the company.

And I think most advice out there are spaces so new that I actually always default to like, there is no advice, like do what's best for your unique scenario, right? So this, I'm gonna be a little bit of a hypocrite here, but the only advice I would give is stick to the business outcome. What I mean by that is, don't show up singing the praises of freelance, right? No one cares that you're a freelancer. Sing the praises of the business outcomes that you can deliver. And because you're serving in a fractional and freelance capacity, those business outcomes are accelerated or they're fractionalized,

going to give cost efficiencies. And so here's a super clear example. If you are coming from a place, so there's two kind of buzzwords right now that we do keep hearing. And the buzzwords aren't, they're kind of things that have been here but haven't necessarily been explicit. And the first is that work is shifting more towards a project basis. So instead of waterfall development, everyone doing the same thing, it's more so what are the projects we have in pipeline and how are they performing?

The second is skills. And so we're hearing a lot around skills-based hiring. Do we have the right skills in the org? How do we go and find the right skills?

Now, from a fractional and freelance capacity, if you want to see if a project is going to work or not work, fractional is a 10 times better way to do that. Specifically, you call out the outcomes, your incentive to if the project doesn't work, you're not going to sit there trying to justify why you shouldn't be laid off or fired. The reality is you can give the exact results knowing that, okay, this project might end or that might mean we work on the next one.

Matthew (16:38.299)
So fractional, you know, it delivers a better business outcome, especially in a project-based and skill-based world.

Brett Trainor (16:46.81)
Yeah, I like that. Because a lot of the time I'll recommend that people focus on the problem, right? Is there transitioning from corporate jobs to fractional or freelance? I'm like, pick a problem that you solve that you're really good. Maybe you've done this for 20 or 30 years. It's evolved. But I think tying that problem with the business outcome, you know, makes a ton of sense. Now you're really speaking to business. Yeah, because the business owner or the enterprise knows they have a problem. But what does the outcome look like and how do you drive it? So tie those two together if you guys out there thinking about this, which

which makes sense. And I'm too, I'm more macro, I'm assuming you're seeing more and more, I know you talked about this spend, is the spend increasing or is it the formal spend? So I guess I'm asking you a bunch of questions. So I'm gonna take that back and then I'm gonna ask the one question. So our businesses, is the opportunity at the bigger company or the companies that are spending a lot on fractional or can you still find business unit by business units spend where people are bringing in

freelancers. That question make sense?

Matthew (17:48.814)
I'm going to reframe it, ready? Is spend growing on fractional slash freelance talent? How's that for a better? Yeah.

Brett Trainor (17:57.21)
Well, let me ask you a bigger question. Is our enterprises leveraging more and more freelancers?

Matthew (18:03.098)
Okay, short answer, yes. Long answer, it depends. There has been freelance spend forever, right? There's never not been contractors.

Brett Trainor (18:07.776)
Okay.

Matthew (18:14.402)
If you were to, one of my favorite exercises, if you were to say look at the corporate card statements and search Upwork and Fiverr, I'm willing to bet you're gonna see a lot of what's called rogue spent. And I'm willing to bet out of the Fortune 100s based off the numbers that we know, over half are gonna have some employees that have profiles and are hiring freelancers on that site. It's probably more, it's probably upwards of 50 to 70%.

So the spend, yes, it is absolutely increasing. Now it's complicated. And the sort of short way to break this up, and I apologize, I'm going to sound very consulting-y, but there is two mutually exclusive things that are happening. And that is that, one, there is more spend, but spend is shifting towards strategic and decreasing in transactional. So there was a lot of models.

Brett Trainor (19:04.946)
CURSE

Matthew (19:08.594)
that were working from, let's say, 2010, 2016 to last year. And those models typically were transaction-based, marketplace-based, more on the gig side. And so for example, that was, let me use a self-service platform to go find someone. Let me have a freelancer for this transaction. That spend, for the most part, seems like it's decreased.

the spend on let's have freelance as strategic has certainly increased. And that looks more like, let's not just go to a freelancer to plug the hole, but let's go to an individual to drive a business outcome, whether that be we need this skill or we need someone that can help drive this outcome, meaning that project. So...

That's the net of the answer. In terms of how that affects the individual, what's gonna be tough for you is that there's a litany of macro forces that are pushing the companies to have to go through a platform to find you and or to work with you. And what I mean by that is, and this is purely from the enterprise side, if you're a large company, there's a lot of regulation slash government that...

is going to get in the way of that company wanting to just work with you directly. So for example, if I misclassify you as a freelancer, meaning a 1099, when you really should be a W2, I might be stepping in back tax and I might be stepping in a class action lawsuit. So not to add a third variable, but we're also seeing, which we've seen, and which is definitely not going away. And we have some experts that we've been talking to just because.

Brett Trainor (20:43.558)
which we've seen, yeah.

Matthew (20:52.366)
there is, there's basically it is kind of party driven. If Democrat then very, very pro-union, which is very not pro-freelancer, if conservative then, or the Republicans, very pro-freelancer. So it does kind of, politics unfortunately has gotten involved.

Brett Trainor (21:11.282)
Very interesting. Yeah, and maybe this is a good transition into some of the best practice because one of the notes I had was, in the SME world, there's really not a, there's no marketplaces, right? There's nobody posting jobs for fractional CMO or fractional CRM specialists. It's just not there yet. But there's ways you can go direct, right, to the companies and figure out, and if you're ambitious and a little...

outgoing, you can uncover those opportunities. But I know at the enterprise level you had mentioned, it's almost a better path to go through. So is there somewhere you can point it? I know you guys do some work with platforms or marketplaces. So if I'm new to this, where are some of the places that I should be looking to find if there is opportunities in some of them that match my skillset? What are some of the best places to start?

Matthew (22:05.874)
Yeah, it's a good question. I'm going to give.

always think about what's closest to you. So that's going to be like the high level answer, right? So if you are sitting in a company right now, go talk to your boss about this, right? Like be strategic about it, but go talk to your boss, go talk across the company, and ideally try to have a couple contracts before you leave the company. Like I just, I don't know whether it's a moral thing or what, I just, I can never give any advice saying, quit your job unless you have something else, right? So, so I'd say that's the first thing, is what's closest to you. Second layer is what's closest to you

like LinkedIn, so then go through your network. Be very explicit about, hey, I want to transition to a fractional path. How can we work together in a fractional capacity? The third thing is I would say then, OK, there are platforms that are doing a lot of the hard work for you. And so I've personally gone through a massive, like, are marketplaces good? Are marketplaces bad? Journey, just because I started as a freelancer, right? And where I've netted out after seeing everything

a very, very important purpose. Now, some platforms can lose their way and some platforms are better for you than others. But in general, platforms are there to find you work and keep you work.

because they make money when you make money. So the idea that platforms are bad, yes, some platforms do things that are really bad. But in general, they are there to find you work, they're there to get you work, they're there to make sure that your client is paying on time, they're there to make sure that your client keeps working with you. So platforms can be really, really good.

Matthew (23:46.934)
With that said, where it gets tough is that platforms are not going to just give you work on a silver platter. And so no matter the platform that you go to, you're still gonna have to hunt. You're still gonna have to quantify your outcomes in a way that a client wants you over the person next to you. That's just the sad reality. Now, when we break up that, increasingly and especially now, there are platforms that match your specific skillset. So for example, if you're a consultant, go to Catalan.

If you are a marketer, go to Growth Collective or the starters. If you're an e-commerce marketer, go to the starters. If you're really good at paid ads, go to Growth Collective. There is a platform that is probably specialized for you. Now, I'm going to give you some kind of insider secret sauce. When you go to these platforms, generally, the larger the platform, the lower the engagement, meaning the lower the percentage that you're going to be able to get a job.

Brett Trainor (24:27.846)
There is.

Matthew (24:44.438)
That's just a sad reality. The not, I don't wanna say the newer, but the smaller the network and the more niche, the more that you're gonna be able to build relationships with either the account managers that are there to get you work or the clients themselves. So my, to summarize it all up, go to which is closest to you, whether it's the people you're working with right now or your LinkedIn, and then go to the platforms.

Brett Trainor (24:46.255)
Right.

Matthew (25:10.742)
but know that the platforms are there to get you work. That's literally what they do. But unfortunately, there's way more freelancers than there is work. And so those platforms, as much as they love you, their harder challenge is getting the work. And so make their life easier and then they'll make your life easier and vice versa. So that would be my advice.

Brett Trainor (25:34.582)
Yeah, no, I love it. And we speak the same language, right? Start with your network, you know, current employer or even previous employers, right? If you've bounced around a little bit, you know, to, yep, LinkedIn and second connections are always super helpful. And then the third is, I don't want to say spray and pray because that's a good strategy, right? It's, it makes sense to be on those platforms where, cause you never know when that one opportunity is going to come through. But I think to your point is don't rely on the, the marketplace or the platforms to.

to deliver. I think this is going to just keep evolving. I'm curious from your perspective too because those tend to, and maybe over time, the more niche it won't, they tend to start driving back towards cost. Who's the lower cost of the three? Part of what the value again with my audience is Gen X. We've been in corporate for 20, 30 years. You've got a lot of experience that can apply and you don't necessarily want to be competing like the old Fiverr model of.

Well, I can do a logo design for $10 or it's $20 to 30. So yeah, I mean, it's evolving. But I do, and what I've seen is the folks that are opportunistic and ask, right? There's not a ton of people asking. So have those conversations and head it down there. So, please.

Matthew (26:54.506)
And if I could add to you, like just to add to that, when you think about a platform, they're literally just a lead channel for you, right? And that's okay. There are platforms though, that as you grow, they do become more. So for example, some platforms are gonna have a higher level of indemnification insurance or a higher level of indemnification.

Brett Trainor (27:03.779)
Okay.

Matthew (27:17.674)
to a level that you can never afford. So you're going to love the fact, meaning you should love the fact that they're taking on that much risk because they have that you can't in order to work with these large enterprises. Other platforms like, for example, Catalan is phenomenal at giving their consultants data on things that make their business better. And so what's interesting about the space is freelance, people stick on the word free. And I do love it. You know what technology does?

and it totally disrupts and it breaks the old way. But there were some good things about working for a company and working for an agency. And one of those things is that they did give you either content or data or things that made you better instead of when you were just on your own. So, I think when looking at the platforms, I would start by just looking at it as a refined lead engine. And instead of just spamming emails all across outbound, a platform is there.

having clients already looking for you. And so just think about it that way. And the last thing I say about is like, usually a marketplace will take 10 to 40%. Right? On the surface, that can sound bad. Why are they taking 10 to 40%? Well, they're doing a lot of marketing on your behalf, number one. Number two, though, there are, on most marketplaces that are good for fractional,

there is a level of brand awareness that you're going to get a bump in pay because you're on that platform. So for example, if you're saying I'm a top talent developer or a Catalan consultant, well, those networks don't allow everyone. So most likely you're going to be able to get a bump, just like how when McKinsey shows up, it's a much, much higher price. And so as the last thing I'll say about the platforms is they do generally allow you a higher premium. Now,

Brett Trainor (29:01.646)
higher paid.

Matthew (29:09.814)
This is not the low cost, large marketplaces, right? I'm talking purely about the niche hyper-focused ones.

Brett Trainor (29:17.506)
Right. Yeah, I know it makes sense. Maybe a good segue or last section I wanted to talk to you about is, and I'm getting a sense maybe there is no one industry or one type that are leveraging freelancers more than others, but are there industries that we should be looking at, type of roles that are more common? The one thing that you and I, I think it was you and I that talked about because I use it all the time.

I think it came from you is right the larger the company the more hyper specialized that they're looking for that skill set to be in the large the smaller the company the more foundational and general right they need those skill sets to be so Looking at that from the enterprise of the scale is there Anywhere you're seeing larger growth or adoption that if I'm somebody that's just starting to look that it would make sense Or are we just in a blanket?

Matthew (30:12.454)
Yeah, I would say the one of the fastest growing types of work actually, and this is specialized for your audience, is intro entry calls actually. So there's this weird gap in the market where you can go to McKinsey for a big old project, right?

Brett Trainor (30:12.714)
Uh, yeah.

Matthew (30:36.822)
You can also go to like a GLG, TGIS, alpha sites and pay 1000 to 3000 hour to talk to someone. But there's a lot of room in between, right? Where I still wanna talk to an expert. I might wanna go hire that expert, but there's a gap because GLG doesn't want you to know who that or doesn't intentionally wants you to just stay within their environment. And McKinsey's obviously your work for McKinsey. So there's something in between.

Now, within enterprises we are seeing, in terms of that something in between, they just, they're struggling to find people, right? And they're struggling to find people that have cutting edge skills. And so that's you, you know, you listeners out there. And so make it easy to start working with you, whether it be just an intro call or an expert call or something like that. And then also have a very, very clear, here's how we get started. Here's a typical proof of concept working with me.

And, Brett, you were really good when we were talking about a sales type proof of concept of here's a three to six month way that we can get started working together. And if this works, it can turn into this. But let's start small, right? Let's build a POC. It's kind of no different than if you're coming in as an agency or a consulting company or you name it. But so that's the segment we've seen. In terms of industry, I mean, tech.

Media has always been at the forefront of leveraging external talent. Media definitely has been at the forefront of exerting freelance talent. There's always been freelance writers, freelance journalists, followed probably by freelance design. A lot of marketing actually has been done by freelancers. A lot of agencies are secretly just freelancers under the hood. Rachel Renick of Weitho always has like a visual of a trench coat where it's like agency here, freelance, you know.

Brett Trainor (32:30.77)
Good.

Matthew (32:31.23)
So there's definitely industries like media and tech have been the lead in adopting this. I guess agencies we could say kind of are an industry unto themselves, right? Agencies themselves have been taking the lead in this as well. Everything can be freelancable, but I would say those three have been taking the lead.

Brett Trainor (32:49.823)
Okay. Interesting. One of the things I was thinking about and I'd love to test it and maybe some of you out there that's, that's interesting. You know, some of these companies with large layoffs, right in different areas, you'll see where they, I wonder if there's an opportunity to go back into some of those leaders and say, Hey, I know you just laid off. I mean, I can offer this skill set at a fraction, right? Cause there's going to be some gaps with these layoffs and you know, wonder if there's an opportunity to

augment or supplement or plug a few holes in the short term as they try to figure out what that business Haven't done it. I'm just as you were as I've seen the layouts. I'm hearing you You're you're talking about this. I'm just curious. What do you think? Is that? It's something worth testing you think

Matthew (33:22.509)
Yeah.

Matthew (33:31.471)
It's a good signal. We don't have enough data to say if that's a good, you know, I kind of go back to my answer of the platforms are actually best incentivized. So a lot of the platforms are already doing that for you.

Brett Trainor (33:35.495)
Yeah.

Brett Trainor (33:45.318)
That's a good point.

Matthew (33:45.87)
can't hurt, you know, and then we and I both get along very well because we started in sales and so from a sales perspective, yeah, let's two to five hours sourcing people like that to go test if it's if it's right. Theoretically, it makes sense. When you get in the weeds, it's

It's interesting because I don't know the source of a lot of these layoffs right now, if I'm being honest. We know that efficiency has been one of the guiding principles and we know that there's this weird contradiction that there's layoffs yet there still is hiring in certain ways. You know, I don't want to get too into but like if you look at like Twitter, right, they laid off. What was it 80% and arguably by the numbers Twitter is better than ever. And so.

I don't know if these layoffs are companies saying that we want to rehire. I don't know if like, there's too much uncertainty around that. Um, but it's, it's not a bad signal. And that's why I kind of jumped to it's a good signal. With that said, the platforms are also out there trying to capitalize in this as well as you, so try it. And when we, when we have data on it, we'll let you know.

Brett Trainor (34:49.966)
Or if I get anybody in the audience or you know folks in the network that do test it and we get some feedback I'll share it with you because I think maybe one last question for you because I mean time flew by here Thinking about when I am what do you want to work with an enterprise or I can set up do I need to be an LLC? I mean, I'm getting super tactical and technical now Is there certain things that I can set myself up ahead of time to make sure or is that something the platform is gonna tell me? You need X Y and Z in order to do it

Matthew (35:19.71)
Yeah, I'll use software language. It's a lag metric. So it won't be the deal breaker in terms of when you're introducing yourself, getting the door open. I've never seen an enterprise leader saying can't work with this person because they are or aren't an LLC. Um, with that said, as you scale, you're probably going to want to, like when I freelance, I'm actually under an S corp and the S corp is a flow through.

Brett Trainor (35:35.463)
God.

Brett Trainor (35:40.89)
Yeah.

Matthew (35:45.086)
It just makes sense when you're at scale. I kind of default to though, my accountant told me that. So like, it's not legal to fringe advice. Yeah, I do know, in certain enterprise accounts, like depending on the platform, they might say, like some platforms might say, hey, you have to be a W2 for this. And then you turn around and go, ooh, I don't want that. So I'd say play it on a case by case basis. If you're serious about this, most likely you're gonna end up incorporating.

Brett Trainor (35:52.024)
As I said, this is not legal or financial advice.

Brett Trainor (36:06.77)
Right.

Matthew (36:15.231)
S-Corp or LLC, talk to your accountant. There's also really good solutions out there like RubyMoney, Collective, Formations. There are plenty of solutions out there now for it.

Brett Trainor (36:26.298)
Do it. Awesome. Well, Matthew, anything else we didn't touch? Definitely want you to share a little bit about Human Cloud, how to connect to get more involved with what you guys are doing. But is there any other topics that we didn't cover today you think we should talk about?

Matthew (36:39.614)
I just want to make fun of you, Brett, and TikTok. For all you listeners, go find Brett on TikTok. I still can't believe. I mean, that is the beauty of fractional slash freelances is you're out there. And I'll just give a quick little data point. The data on upskilling significantly favors freelancers by I think a 20 to 40%, whatever you call it, standard deviation. And so...

Brett Trainor (36:56.846)
All right.

Matthew (37:02.25)
Like I think I think the number is like 40% of full-time people will upscale where 67% of freelancers. Well, numbers are on there. Don't, you know, don't quote me there.

Brett Trainor (37:10.47)
Did you?

Matthew (37:11.026)
But it's that level of that direction. And so someone like you, Brett, you're out there trying TikTok. That's incredible. If you were a full-time employee, you probably wouldn't be doing that because you'd be scared that I'm gonna get in trouble. And so someone like you is out there trying TikTok, trying new channels because you're a business owner, because you love what you're doing because you wanna provide the best service. And so like one, someone like you and the fractional person listening, lean into that, right? You guys are cutting edge.

Brett Trainor (37:25.204)
100%

Brett Trainor (37:30.383)
Thank you.

Matthew (37:41.72)
are farther than a full-time employee is. From the business side, well then, duh. Make sure you have freelancers and fractional because you need to stay ahead of the curve. And so not everyone's gonna be a freelancer or fractional. You'll still have that core team, but.

you're just missing if you don't, right? And then not to sound too simple, like a simple motto, but you're just missing out. And so that's the guiding thing I just wanna leave with your listeners and also from the client side as well. In terms of HumanCloud, yeah, humancloud.work, you can find me on LinkedIn. Would love to help. We default to people like you though, Brett. So from the freelancer side, I just can't thank you and all the great people enough for curating these communities of fractional

It's really, really exciting. The last thing I guess I'll call out is, fractional is a facet of the free, we consider it a segment of the freelance economy. I know some fractional people probably wanna punch me through the, however they're listening to it, because some don't wanna be called freelancers, but reality is under this freelance bucket, fractional is a very, very exciting segment of it. And...

Brett Trainor (38:40.772)
people.

Matthew (38:51.658)
It's just really cool to see someone that could be a director, a VP, a CEO, a CMO, you name it, realize the benefits of being fractional. So power to every single one of you listening and your listeners. And thank you, Brett, for driving the communities that leave the industry forward.

Brett Trainor (39:09.682)
That's awesome. But likewise, man, what you guys are doing, like I said, I was surprised we hadn't met, I guess it's been a few months now, but then you know, with the work that you guys are doing, I'm like, we're a vibe and how did I miss what you guys are doing? So now you guys keep it up because right, I think that's the biggest gap is getting enterprise and the business side across the board more comfortable with freelance and fractional and like you said, whatever you want to label that the future workforce, right, it's just more flexible. I think somebody called it more water or liquid.

Matthew (39:16.584)
Yeah.

Matthew (39:39.262)
Yeah. That was 2016, Brett. Accenture said that in 2016. We're gonna make a damn visual that's like, hey, this company said this and this and this and this and this, I mean, on-demand talent, right? It's all, there's gonna be a new talent every other day. I don't know what to call it. For you listeners, email me the name you think is best. Hell, find out what the name should be.

Brett Trainor (39:39.618)
you know, workforce that it can kind of fit mold around.

Brett Trainor (39:58.862)
Yeah, I mean, I'm still trying to figure that out. I mean, because at the end of the day, one, you don't necessarily want to be in a bucket. If you're fractional, it's easy. You can start to define it. That's what you want to do. But you've got the consultants, you got the freelance, you got the interims. So you, you know, it's, I joke, it's like the old high school, you know, subculture of, you know, different, all the different funds. Yeah, exactly. But the beauty is you don't have to define it, right? Depending on if you find the right business, it's, it's solving that problem and delivering the business outcome.

Matthew (40:17.363)
The jugs, yeah.

Matthew (40:22.602)
Yeah.

Brett Trainor (40:27.526)
You can kind of scope it the way you want to make it, scope it as long as the business is on board with it. So Matthew, we got to figure out, I got to get you back on a regular basis because like this world is moving super quick. So maybe on a quarterly basis, we'll have you come back in, give us an update what you're seeing. What are the new trends? What are the things that we need to be looking out for? Yeah, so folks go connect with Matthew and John and HumanCloud and it's a great resource for you. So Matthew, appreciate you spending a few minutes with us today.

Matthew (40:57.716)
Thank you so much for having me.

Brett Trainor (40:59.605)
Awesome, we'll catch up with you in this soon.